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Structure type: oligomer
Trivial name: acteoside, verbascoside, acteoside, verbascoside, trans-verbascoside, verbascoside, acteoside
Compound class: saponin glycoside, glycoside, phenolic glycoside, phenylethanoid glycoside, phenylpropanoid glycoside, iridoid glycoside, lignan glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_189517,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 9197
  Kobayashi H, Oguchi H, Takizawa N, Miyase T, Ueno A, Usmanghani K, Ahmad M "New phenylethanoid glycosides from Cistanche tubulosa (Schrenk) Hook. f. I." - Chemical and Pharmaceutical Bulletin 35(8) (1987) 3309-3314
  

  Four new phenylethanoid glycosides, tubulosides A (II), B (VI), C (VII) and D (VIII), have been isolated from Cistanche tubulosa (Schrenk) Hook. f. (Orobanchaceae), together with four known phenylethanoid glycosides, echinacoside (I), acteoside (III), acteoside isomer (IV) and 2'-acetylacteoside (V). The structures of II, VI, VII and VIII were established on the basis of chemical evidence and spectral data. Compounds VII and VIII possess a triacetylrhamnosyl moiety as the terminal sugar.

  Cistanche tubulosa, Orobanchaceae, parasitic plant, phenylethanoid glycoside, tubuloside A, tubuloside B, tubuloside C, tubuloside D

  Publication DOI: 10.1248/cpb.35.3309
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Central Research Laboratories, Yomeishu Seizo Co., Ltd., Minowa, Japan, Shizuoka College of Pharmacy, Shizuoka, Japan, Department of Pharmacognosy, Faculty of Pharmacy, University of Karachi, Karachi, Pakistan
  Methods: 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GC, methanolysis, HPLC, UV, extraction, optical rotation measurement, acetylation, CC, melting point determination
  
   
  
  Cistanche tubulosa
  CSDB ID 50493 (all data & tools)
• Article ID: 9208
  Xiong Q, Kadota S, Tani T, Namba T "Antioxidative effects of phenylethanoids from Cistanche deserticola" - Biological and Pharmaceutical Bulletin 19(12) (1996) 1580-1585
  

  The acetone-H2O (9:1) extract from the stem of Cistanche deserticola showed a strong free radical scavenging activity. Nine major phenylethanoid compounds were isolated from this extract. They were identified by NMR as acteoside, isoacteoside, 2'-acetylacteoside, tubuloside B, echinacoside, tubuloside A, syringalide A 3'-α-rhamnopyranoside, cistanoside A and cistanoside F. All of these compounds showed stronger free radical scavenging activities than α-tocopherol on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and xanthine/xanthine oxidase (XOD) generated superoxide anion radical (O2-.). Among the nine compounds, isoacteoside and tubuloside B, whose caffeoyl moiety is at 6'-position of the glucose, showed an inhibitory effect on XOD. We further studied the effects of these phenylethanoids on the lipid peroxidation in rat liver microsomes induced by enzymatic and non-enzymatic methods. As expected, each of them exhibited significant inhibition on both ascorbic acid/Fe2+ and ADP/NADPH/Fe3+ induced lipid peroxidation in rat liver microsomes, which were more potent than α-tocopherol of caffeic acid. The antioxidative effect was found to be potentiated by an increase in the number of phenolic hydroxyl groups in the molecule.

  glycosides, Cistanche deserticola, antiodixant activity

  NCBI PubMed ID: 8996643
  Publication DOI: 10.1248/bpb.19.1580
  Journal NLM ID: 9311984
  Publisher: Pharmaceutical Society of Japan
  Institutions: Research Institute for Wakan-Yaku (Traditional Sino-Japanese Medicines), Toyama Medical and Pharmaceutical University, Toyama, Japan, Research Laboratories for High Quality of Life, Sumitomo Metal Industries Ltd., Kyoto, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, biological assays, UV, extraction, CC, antioxidant activities, inhibitory studies
  
   
  
  Cistanche deserticola
  CSDB ID 50558 (all data & tools)
• Article ID: 11136
  Damtoft S, Franzyk H, Jensen SR "Iridoid glucosides from Picconia excelsa" - Phytochemistry 45(4) (1997) 743-750
  

  An investigation of the iridoids of Picconia excelsa from Tenerife provided 17 iridoid glucosides together with verbascoside. Major constituents (> 0.5%) were loganin, ketologanin, oleoacteoside and the new picconioside 1-a bisiridoid consisting of loganin esterified with deoxyloganin. Minor constituents were secoxyloganin, 8-epi-kingiside, 8-epi-kingisidic, oleoside 11-methyl ester, excelsioside, ligstroside and loganic acid together with the new compounds ketologanic acid, 6β-hydroxy-7-epi-loganin and picconiosides II-V, the latter four being esters of loganin and menthiafolic, foliamenthic, 6-(Z)-foliamenthic or 6,7-dihydrofoliamenthic acid. The structures were mainly elucidated by NMR spectroscopy.

  II, iridoid glucosides, Oleaceae, verbascoside, secoiridoid glucosides, Picconia excelsa, picconiosides I, III, IV, and V, loganic acid, loganin, 7-ketologanic acid, 7-ketologanin, 6β-hydroxy-7-epi-loganin, 8-epi-kingisidic acid, 8-epi-kingiside, secoxyloganin, oleosid, 11 -methyl ester, ligstroside, excelsioside, oleoacteoside

  Publication DOI: 10.1016/S0031-9422(97)00023-X
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Organic Chemistry, The Technical University of Denmark, DK-2800 Lyngby, Denmark
  Methods: 13C NMR, 1H NMR, sugar analysis, TLC, chemical methods, alkaline hydrolysis, UV, extraction, acetylation, HPLC-RP
  
   
  
  Picconia excelsa
  CSDB ID 60298 (all data & tools)
• Article ID: 11315
  Franzyk H, Husum TL, Jensen SR "A caffeoyl phenylethanoid glycoside from Plantago myosuros" - Phytochemistry 47(6) (1998) 1161-1162
  

  From Plantago myosuros, the iridoid glucoside, aucubin was isolated, together with the caffeoyl phenylethanoid glycosides, plantalloside and verbascoside. Plantalloside is a new verbascoside analogue with a beta-allopyranosyl moiety. The structure was elucidated by NMR spectroscopy.

  verbascoside, Plantago myosuros, Plantaginaceae, aucubin, plantalloside, alloside

  Publication DOI: 10.1016/S0031-9422(97)00527-X
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Organic Chemistry, The Technical University of Denmark, Lyngby, Denmark
  Methods: 13C NMR, 1H NMR, extraction, optical rotation measurement, reversed-phase chromatography
  
   
  
  Plantago myosuros
  CSDB ID 61161 (all data & tools)
• Article ID: 11327
  Kernan MR, Amarquaye A, Chen JL, Chan J, Sesin DF, Parkinson N, Ye ZJ, Barrett M, Bales C, Stoddart CA, Blanc P, Sloan B, Limbach C, Mrisho S, Rozhon EJ "Antiviral phenylpropanoid glycosides from the medicinal plant Markhamia lutea" - Journal of Natural Products 61(5) (1998) 564-570
  

  Three new phenylpropanoid glycosides, named luteoside A (3), luteoside B (4), and luteoside C (5), were isolated together with the known compounds verbascoside (1) and isoverbascoside (2) from the roots of the medicinal plant Markhamia lutea. The structures of the new compounds were determined to be 1-O-(3, 4-dihydroxyphenyl)ethyl beta-D-apiofuranosyl(1-->2)-alpha-l-rhamnopyranosyl(1-->3)-4-O- caffeo yl-6-acetyl-beta-d-glucopyranoside, 1-O-(3,4-dihydroxyphenyl)ethyl beta-d-apiofuranosyl(1-->2)-alpha-l-rhamnopyranosyl(1-->3)-6-O- caffeo yl-beta-d-glucopyranoside, and 1-O-(3,4-dihydroxyphenyl)ethyl beta-D-apiofuranosyl(1-->2)-alpha-l-rhamnopyranosyl(1-->3)-6-O- ferulo yl-beta-d-glucopyranoside, respectively, on the basis of chemical and spectroscopic data. All five phenylpropanoid glycosides exhibited potent in vitro activity against respiratory syncytial virus.

  glycosides, Plants, luteoside, Markhamia lutea

  NCBI PubMed ID: 9599250
  Publication DOI: 10.1021/np9703914
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Kernan MR
  Institutions: Shaman Pharmaceuticals, San Francisco, California, Tanga AIDS Working Group (c/o David Scheinman), Rural Development Association, Tanzania, East Africa
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, HPLC, UV, optical rotation measurement, acetylation, hydrolysis, reversed-phase chromatography, biological assay, HMBC, centrifugal partition chromatography, HMQC, COSY, HR-FAB-MS, extraciton, HMQC-TOCSY, antiviral assays, cytotoxicity assays
  
   
  
  Markhamia lutea
  CSDB ID 61222 (all data & tools)
• Article ID: 11445
  Chen JL, Blanc P, Stoddart CA, Bogan M, Rozhon EJ, Parkinson N, Ye ZJ, Cooper R, Balick M, Nanakorn W, Kernan MR "New iridoids from the medicinal plant Barleria prionitis with potent activity against respiratory syncytial virus" - Phytochemistry 61(10) (1998) 1295-1297
  

  Two new iridoid glycosides (1 and 2), together with the known compounds barlerin (3) and verbascoside (4), were isolated from Barleria prionitis. The new iridoid glycosides were determined to be 6-O-trans-p-coumaroyl-8-O-acetylshanzhiside methyl ester (1) and its cis isomer (2) by using spectroscopic, especially 2D NMR, data, A 3:1 mixture of 1 and 2 was shown to have potent in vitro activity against respiratory syncytial virus (EC50 2.46 mu g/mL, IC50 42.2 mu g/mL).

  glycosides, Iridoids, Barleria prionitis, respiratory virus

  NCBI PubMed ID: 9784173
  Publication DOI: 10.1021/np980086y
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: Kernan MR
  Institutions: Shaman Pharmaceuticals, Inc., San Francisco, US, Institute of Economic Botany, New York Botanical Garden, New York, US, The Botanical Garden Organization, Chiang Mai, Thailand
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, HPLC, UV, extraction, optical rotation measurement, HMBC, HR-FAB-MS, antiviral assay, antiviral activity
  
   
  
  Passiflora edulis
  CSDB ID 61778 (all data & tools)
• Article ID: 11455
  Giner RM, Villalba ML, Recio MDC, Manez S, Gray AI, Rio JL "New iridoid from Scrophularia auriculata ssp. pseudoauriculata" - Journal of Natural Products 61(9) (1998) 1162-1163
  

  A new iridoid glycoside, scrovalentinoside (1), was isolated from the MeOH extract of the aerial parts of Scrophularia auriculata L. ssp. pseudoauriculata. The structure of the new compound 1 was elucidated as 6-O-(2", 3"-di-O-acetyl-4"-O-p-methoxy-cinnamoyl)-alpha-L-rhamnopyranosyl catalpol by spectroscopic methods. The known iridoid glycoside, scropolioside A; two saponins, verbascosaponin A and verbascosaponin; and the phenylethanoid glycoside, verbascoside, were also isolated.

  leaves, Premna japonica, scorodonia, ilwensis

  NCBI PubMed ID: 9748391
  Publication DOI: 10.1021/np980067o
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Rio JL
  Institutions: Departament de Farmacologia, Facultat de Farmàcia, Universitat de València, Valencia, Spain, Department of Pharmaceutical Sciences, University of Strathclyde, Glasgow, Scotland, UK
  Methods: 13C NMR, 1H NMR, FAB-MS, extraction, CC, HMBC, HMQC, COSY, NOESY
  
   
  
  Scrophularia auriculata ssp. pseudoauriculata
  CSDB ID 61820 (all data & tools)
• Article ID: 11504
  Yamamoto H, Yoshida K, Kondo Y, Inoue K "Production of cornoside in Abeliophyllum distichum cell suspension cultures" - Phytochemistry 48(2) (1998) 273-277
  

  The production of phenylethanoid derivatives in callus and cell suspension cultures of four oleaceous plants, Abeliophyllum distichum, Forsythia suspensa, F. viridissima, and F. koreana was investigated. Of two types of A. distichum cultured cells, the friable fine cells produced only the 4-hydroxyphenylethanoid-type glucoside, cornoside, whereas the small cell aggregates produced the 3,4-dihydroxyphenylethanoid-type glycosides (i.e. verbascoside) predominantly. In the cultured cells of F. suspensa and F. viridissima, the latter-type glycosides were produced predominantly and from those of F. koreana, lignan glucosides with 3,4-dioxygenated phenyl groups were isolated.

  production, Forsythia suspensa, Oleaceae, cornoside, Abeliophyllum distichum, benzoquinolethanoid glucoside, cell suspension cultures, F. koreana, F. viridissima, phenylethanoid glycosides

  Publication DOI: 10.1016/S0031-9422(97)01134-5
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Pharmacognosy, Gifu Pharmaceutical University, Gifu, Japan
  Methods: extraction, CC, RP-HPLC
  
   
  
  Abeliophyllum distichum, Forsythia viridissima
  CSDB ID 62012 (all data & tools)
• Article ID: 11670
  Xiong Q, Hase K, Tezuka Y, Namba T, Kadota S "Acteoside inhibits apoptosis in D-galactosamine and lipopolysaccharide-induced liver injury" - Life Sciences 65(4) (1999) 421-430
  

  We assessed the effect of acteoside, a naturally occurring antioxidative phenylethanoid, on hepatic apoptosis and the subsequent liver failure induced by D-Galactosamine (D-GalN) and lipopolysaccharide (LPS). A co-administration of D-GalN (700 mg/kg) and LPS (35 μg/kg) to mice evoked typical hepatic apoptosis characterized by DNA fragmentation and apoptotic body formation, resulting in fulminant hepatitis and lethality of mice. Pre-administration of acteoside at 10 or 50 mg/kg subcutaneously at 12 and 1 h prior to D-GalN/LPS intoxication significantly inhibited hepatic apoptosis, hepatitis and lethality. Tumor necrosis factor-α (TNF-α) secreted from LPS-stimulated macrophages is an important mediator of apoptosis in this model. Acteoside showed no apparent effect on the marked elevation of serum TNF-α, but it partially prevented in vitro TNF-α (100 ng/ml)-induced cell death in D-GalN (0.5 mM)-sensitized hepatocytes at the concentrations of 50, 100 and 200 μM. These results indicated that D-GalN/LPS-induced hepatic apoptosis can be blocked by an exogenous antioxidant, suggesting the involvement of reactive oxygen intermediates (ROIs) in TNF-α-dependent hepatic apoptosis.

  Lipopolysaccharide, apoptosis, necrosis, acteoside, tumor necrosis factor-α, reactive oxygen intermediates, D-galactosamine

  NCBI PubMed ID: 10421428
  Publication DOI: 10.1016/S0024-3205(99)00263-5
  Journal NLM ID: 0375521
  Publisher: Amsterdam: Elsevier
  Institutions: Research Institute for Wakan-Yaku (Traditional Sino-Japanese Medicines), Toyama Medical and Pharmaceutical University, 2630-Sugitani, Toyama 930-0194, Japan
  Methods: NMR, DNA techniques, statistical analysis, TNF-α assay, antioxidant activities, histological analysis, apoptosis assay, hepatoprotective activity assay
  
   
  
  Cistanche deserticola
  CSDB ID 62461 (all data & tools)
• Article ID: 11726
  Takeda Y, Kinugawa M, Masuda T, Honda G, Otsuka H, Sezik E, Yesilada E "Phlomisethanoside, a phenylethanoid glycoside from Phlomis grandiflora var. grandiflora" - Phytochemistry 51(2) (1999) 323-325
  

  From the aerial parts of Phlomis grandiflora var. grandiflora, a new phenylethanoid glycoside, phlomisethanoside, was isolated together with the known compounds, verbascoside, phlomoside A, 8-epiloganin, citroside and benzyl alcohol β-D-glucoside. The structure of the new compound was elucidated by spectral analyses.

  phenylethanoid glycoside, Labiatae, Phlomis grandiflora var. grandiflora, phlomisethanoside

  Publication DOI: 10.1016/S0031-9422(98)00734-1
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Faculty of Pharmacy, Gazi University, Ankara 06330, Turkey, Faculty of Integrated Arts and Sciences, The University of Tokushima, Tokushima 770-8502, Japan, Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan, Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Minami-ku, Hiroshima 734-8551, Japan
  Methods: 13C NMR, 1H NMR, HPLC, UV, optical rotation measurement, HR-FAB-MS
  
   
  
  Phlomis grandiflora var. grandiflora
  CSDB ID 62677 (all data & tools)
• Article ID: 11732
  Kisiel W, Piozzi F "Phenylethanoid glycosides from Prostanthera melissifolia" - Phytochemistry 51(8) (1999) 1083-1085
  

  Six phenylethanoid glycosides were isolated from aerial parts of Prostanthera melissifolia, together with apigenin and ursolic acid. The glycosides were characterized by spectral methods as martynoside, isomartynoside, verbascoside, isoverbascoside, betonyoside F and isobetonyoside F, the latter being a new natural product.

  Lamiaceae, phenylethanoid glycosides, Prostanthera melissifolia, isobetonyoside F

  Publication DOI: 10.1016/S0031-9422(99)00167-3
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Phytochemistry, Institute of Pharmacology, Polish Academy of Sciences, PL-31-343 Kraków, Poland, Department of Organic Chemistry, University of Palermo, 90-123 Palermo, Italy
  Methods: 1H NMR, TLC, ESI-MS, UV
  
   
  
  Prostanthera melissifolia
  CSDB ID 62702 (all data & tools)
• Article ID: 11761
  Didry N, Seidel V, Dubreuil L, Tillequin F, Bailleul F "Isolation and antibacterial activity of phenylpropanoid derivatives from Ballota nigra" - Journal of Ethnopharmacology 67(2) (1999) 197-202
  

  In addition to the previously isolated phenylpropanoid glycosides verbascoside 1, forsythoside B 2, arenarioside 3 and ballotetroside 4, another four compounds were isolated from generative aerial parts of Ballota nigra: three phenylpropanoid glycosides, alyssonoside 5, lavandulifolioside 6 and angoroside A 7 and a non-glycosidic derivative (+)-(E)-caffeoyl-L-malic acid 8. The antibacterial activity of the five major compounds (1-4 and 8) was tested against Gram-positive and Gram-negative bacteria. Three of them (1-3) exhibited a moderate antimicrobial activity against Proteus mirabilis and Staphylococcus aureus including one methicillin-resistant strain.

  antimicrobial activity, Ballota nigra, phenylpropanoid non-glycosidic ester, phenylpropanoid glycosidic esters

  NCBI PubMed ID: 10619384
  Publication DOI: 10.1016/S0378-8741(99)00019-7
  Journal NLM ID: 7903310
  Publisher: Limerick: Elsevier Sequoia
  Institutions: Laboratoire de Pharmacognosie, Faculté des Sciences Pharmaceutiques et Biologiques, B.P. 83, 59006 Lille Cedex, France, Laboratoire de Bactériologie, Faculté des Sciences Pharmaceutiques et Biologiques, B.P. 83, 59006 Lille Cedex, France, Laboratoire de Pharmacognosie, Faculté des Sciences Pharmaceutiques et Biologiques, U.R.A. au C.N.R.S. no. 1310, 4, Avenue de l’Observatoire, 75006 Paris, France
  Methods: 13C NMR, 1H NMR, TLC, colorimetry, optical rotation measurement, acetylation, antibacterial assay, COSY, HETCOR, COLOC
  
   
  
  Ballota nigra
  CSDB ID 62800 (all data & tools)
• Article ID: 11792
  Iossifova T, Vogler B, Klaiber I, Kostova I, Kraus W "Caffeic acid esters of phenylethanoid glycosides from Fraxinus ornus bark" - Phytochemistry 50(2) (1999) 297-301
  

  A new phenylethanoid glucoside, 2-(3,4-dihydroxyphenyl)-ethyl-O-β-D-glucopyranosyl-(1→6)-3-O-trans-caffeoyl-β-D-glucopyranoside, named isolugrandoside, was isolated from Fraxinus ornus bark, together with the five known phenylethanoid glycosides 2-(4-hydroxyphenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside, calceolarioside B, verbascoside, isoacteoside and lugrandoside. Isomerization of lugrandoside to isolugrandoside was not found under the employed conditions of isolation and purification.

  Oleaceae, calceolarioside B, verbascoside, phenylethanoid glycosides, Fraxinus ornus L, 2-(4-hydroxyphenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside, isoacteoside, lugrandoside, isolugrandoside

  Publication DOI: 10.1016/S0031-9422(98)00538-X
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia 1113, Bulgaria, Department of Chemistry, University of Hohenheim, Stuttgart 70593, Germany
  Methods: 13C NMR, 1H NMR, IR, TLC, HPLC, UV, optical rotation measurement, TOCSY, HMBC, DEPT, COSY, NOESY, HSQC, HR-FAB-MS, TFA hydrolysis
  
   
  
  Fraxinus ornus
  CSDB ID 62974 (all data & tools)
• Article ID: 11800
  Kong LD, Wolfender JL, Cheng CHK, Hostettmann K, Tan RX "Xanthine oxidase inhibitors from Brandisia hancei" - Planta Medica 65(8) (1999) 744-746
  

  Xanthine oxidase is a key enzyme associated with the incidence of hyperuricemia-related disorders. Repeated chromatography of the enzyme inhibitory part of the water extract of the twigs and leaves of Brandisia hancei (Scrophulariaceae) gave a flavone luteolin, an iridoid glycoside mussaenoside, two β-sitosterol glycosides daucosterol and β-sitosterol gentiobioside, and five phenylethanoids arenarioside, brandioside, acteoside, 2'-O-acetylacteoside and isoacteoside. Luteolin and isoacteoside inhibited the xanthine oxidase (XO, EC 1.2.3.2) with the IC50 values at 7.83 and 45.48 μM, respectively. Isoacteoside was found to be the first phenylethanoid that decreased substantially the formation of uric acid by inhibiting competitively xanthine oxidase (K(i) value: 10.08 μM). Furthermore, the study suggested that the caffeoylation of the 6'-hydroxyl group of the phenylethanoids was essential for the enzyme inhibitory action.

  inhibitor, Brandisia hancei, xanthine oxidase

  NCBI PubMed ID: 10630118
  Publication DOI: 10.1055/s-2006-960854
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: Tan RX
  Institutions: Department of Biochemistry, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong, China, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Science, Nanjing University, Nanjing, China, Institute of Pharmacognosy & Phytochemistry, School of Pharmacy, University of Lausanne, BEP, Lausanne-Dorigny, Switzerland
  Methods: 13C NMR, 1H NMR, FAB-MS, inhibition studies, TLC, MS, HPLC, UV, optical rotation measurement, HMBC, HMQC, DEPT, COSY, LC-UV
  
   
  
  Brandisia hancei
  CSDB ID 63022 (all data & tools)
• Article ID: 11801
  Cuendet M, Potterat O, Hostettmann K "Iridoid glucosides, phenylpropanoid derivatives and flavonoids from Bartsia alpina" - Pharmaceutical Biology 37(4) (1999) 318-320
  

  Three iridoid glucosides, two phenylpropanoid derivatives and one flavonoid have been isolated from the methanolic whole plant extract of Bartsia alpina L. (Scrophulariaceae). Their structures were established by spectrometric (UV, D/CI and FAB mass spectrometry, 1H and 13C NMR) and chemical methods. Some of these compounds have radical scavenging activity against DPPH or antioxidant activity against beta-carotene on TLC bioassay.

  flavonoid, Antioxidant activity, radical scavenging activity, Scrophulariaceae, Iridoids, phenylpropanoid derivatives, Bartsia alpina

  Publication DOI: 10.1076/phbi.37.4.318.5808
  Journal NLM ID: 9812552
  Publisher: Lisse, the Netherlands: Swets & Zeitlinger
  Correspondence: Hostettmann K
  Institutions: Institut de Pharmacognosie et Phytochimie, Université de Lausanne, BEP, CH-1015 Lausanne, Switzerland
  Methods: 13C NMR, 1H NMR, TLC, UV, antioxidant activities, MPLC, HPLC-UV
  
   
  
  Bartsia alpina
  CSDB ID 63034 (all data & tools)
• Article ID: 11802
  Akcoş Y, Ezer N, Calis I, Demirdamar R, Tel BC "Polyphenolic compounds of Sideritis lycia and their anti-inflammatory activity" - Pharmaceutical Biology 37(2) (1999) 118-122
  

  Four phenylpropanoid glycosides lavandulifolioside 1, martynoside 2, verbascoside (= acteoside) 3 and leucosceptoside A 4, were isolated from aerial parts of Sideritis lycia Boiss. et Heldr. (Lamiaceae). Their structures were determined by chromatographic and spectroscopic methods (UV, IR, 1H-NMR, 13C-NMR, FAB-MS). These compounds and flavonoid glycosides isolated from the same plant in our previously study were screened for their anti-inflammatory activity using the carrageenan-induced mouse paw edema test. The active compounds were investigated for their effect on gastric ulceration. Although flavonoid glycosides showed higher activity than the phenylpropanoid glycosides, the gastric ulceration effect of phenylpropanoid glycosides was less than flavonoid glycosides.

  anti-inflammatory activity, flavonoid glycosides, phenylpropanoid glycosides, Lamiaceae, Sideritis lycia, gastric ulceration

  Publication DOI: 10.1076/phbi.37.2.118.6081
  Journal NLM ID: 9812552
  Publisher: Lisse, the Netherlands: Swets & Zeitlinger
  Institutions: Departament of Pharmacognosy, Faculty of Pharmacy, University of Hacettepe, Turkey, Departament of Pharmaceutical Botany, Faculty of Pharmacy, University of Hacettepe, Turkey, Departament of Pharmacology, Faculty of Pharmacy, University of Hacettepe, Turkey
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, UV, statistical analysis, MPLC, anti-inflammatory assays
  
   
  
  Sideritis lycia
  CSDB ID 63038 (all data & tools)
• Article ID: 11809
  Su B, Zhu Q, Gao K, Yuan C, Jia Z "Lignan and phenylpropanoid glycosides from Lancea tibetica and their antitumor activity" - Planta Medica 65(6) (1999) 558-561
  

  A new lignan glucoside, the first 7,9'-monoepoxytetrahydrofuran type lignan with the cis-relationship of H-7 and H-8, named tibeticoside (1), as well as ten known compounds have been isolated from the medicinal plant (roots, stems and leaves) Lancea tibetica. The structure of tibeticoside (1) has been elucidated on the basis of chemical and spectral evidence, especially by 2D-NMR (1H-1H COSY, HMQC, HMBC, NOESY). In addition, sylvatesmin (6) exhibited effective antitumor activity on B16 cells.

  antitumor activity, Scrophulariaceae, phenylpropanoid glycosides, Lancea tibetica, lignan glucoside, tibeticoside

  NCBI PubMed ID: 10483379
  Publication DOI: 10.1055/s-1999-14026
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: Jia Z
  Institutions: Department of Chemistry, National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, China
  Methods: 13C NMR, 1H NMR, IR, UV, optical rotation measurement, acetylation, PC, HMBC, antitumor activity assay, HMQC, DEPT, COSY, NOESY, HCl hydrolysis
  
   
  
  Lancea tibetica
  CSDB ID 63067 (all data & tools)
• Article ID: 11857
  Skrzypek z, Wysokińska H, Świątek L, Wróblewski AE "Phenylpropanoid glycosides from Penstemon serrulatus" - Journal of Natural Products 62(1) (1999) 127-129
  

  Two new phenylpropanoid glycosides named cis-martynoside (1) and cis-leucosceptoside A (3) were recognized in cell suspension cultures of Penstemon serrulatus Menz. The structures of these compounds were determined on the basis of 1H NMR spectral data.

  phenylpropanoid glycoside, cis-martynoside, cis-leucosceptoside A, Penstemon serrulatus

  NCBI PubMed ID: 9917298
  Publication DOI: 10.1021/np970465b
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Institutions: Laboratory of Botany and Laboratory of Organic Chemistry, Faculty of Pharmacy, Muszyńskiego 1, 90-151 Łódź, Poland
  Methods: 1H NMR, TLC, HPLC, LSI-MS, alkaline hydrolysis, UV, optical rotation measurement, HCl hydrolysis, isomerization
  
   
  
  Penstemon serrulatus
  CSDB ID 63267 (all data & tools)
• Article ID: 11872
  Calis I, Kirmizibekmez H, Ruegger H, Sticher O "Phenylethanoid glycosides from Globularia trichosantha" - Journal of Natural Products 62(8) (1999) 1165-1168
  

  Five phenylethanoid glycosides, crenatoside (= oraposide) (1), verbascoside (= acteoside) (2), trichosanthoside A (3), rossicaside A (4), and trichosanthoside B (5), were isolated from the aerial parts of Globularia trichosantha. Compounds 3 and 5 are new natural compounds, and their structures were established as 3,4-dihydroxy-β-phenylethoxy-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl(1-→3)-4-O-caffeoyl-β-D-glucopyranoside and 3,4-dihydroxy-β-phenylethoxy-O-[β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl(I→3)]-[β-D-xylopyranosyl-(1→6)]-4-O-caffeoyl-β-D-glucopyranoside, respectively. The structures of all compounds were established by spectral evidence. Compounds 1-5 also demonstrated scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl radical in TLC autographic assays.

  phenylethanoid glycoside, verbascoside, acteoside, Globularia trichosantha, crenatoside, oraposide, trichosanthoside A, rossicaside A, trichosanthoside B

  NCBI PubMed ID: 10479329
  Publication DOI: 10.1021/np9900526
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Çalis I
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Department of Pharmacy, Swiss Federal Institute of Technology (ETH) Zurich, CH-8057 Zürich, Switzerland, Laboratory for Inorganic Chemistry, ETH Zurich, CH-8092 Zürich, Switzerland
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, ESI-MS, UV, optical rotation measurement, TOCSY, antioxidant activities, HMBC, HMQC, COSY, MPLC
  
   
  
  Globularia trichosantha
  CSDB ID 63310 (all data & tools)
• Article ID: 11895
  Takeda T, Narukawa Y, Hada N "Studies on the constituents of Leonotis nepetaefolia" - Chemical and Pharmaceutical Bulletin 47(2) (1999) 284-286
  

  Three antioxidative phenylethanoid glycosides and two new iridoid glycosides, along with three known iridoids were isolated from the African medicinal plant, Leonotis nepetaefolia R. BR. (Labiatae). The new iridoid glycosides were established as 10-O-(trans-3,4-dimethoxycinnamoyl)geniposidic acid and 10-O-(p-hydroxybenzoyl)geniposidic acid. Antioxidative activities of the compounds were measured by α,α-diphenyl-β-picrylhydrazyl (DPPH) method, and the three known phenylethanoid glycosides, acteoside, martynoside and lavandulifolioside showed strong antioxidative activity.

  antioxidative activity, phenylethanoid glycoside, Labiatae, Leonotis nepetaefolia, acylated geniposidic acid

  Publication DOI: 10.1248/cpb.47.284
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Kyoritsu College of Pharmacy, Tokyo, Japan
  Methods: 13C NMR, 1H NMR, FAB-MS, TLC, HPLC, alkaline hydrolysis, UV, optical rotation measurement, antioxidant activities, HMBC, HR-FAB-MS
  
   
  
  Leonotis nepetifolia
  CSDB ID 63400 (all data & tools)
• Article ID: 11962
  Abdel-Kader MS, Stermitz FR "Iridoid and other glycosides from Penstemon species" - Phytochemistry 34(5) (1993) 1367-1371
  

  Five new iridoid glucosides and three new monoterpenoid glucosides were identified from Penstemon albidus, P. cyathophorus and P. virens. Notable among these isolates were conjugates of the monoterpenoids 5,8-dihydroxy-2,6-dimethyloctadienoic acid and 8-oxo-2,6_dimethyloctadienoic acid.

  iridoid glucosides, Penstemon, monoterpenoid glucosides

  Publication DOI: 10.1016/0031-9422(91)80031-U
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Chemistry, Colorado State University, Fort Collins, USA
  Methods: 13C NMR, 1H NMR, alkaline hydrolysis, extraction, optical rotation measurement, acetylation, CC, melting point determination, evaporation, VLC
  
   
  
  Penstemon albidus, Penstemon cyathophorus, Penstemon virens
  CSDB ID 64516 (all data & tools)
• Article ID: 11996
  Andary C, Wylde R, Maury L, Heitz A, Dubourg A, Nishibe S "X-ray analysis and extended NMR study of oraposide" - Phytochemistry 37(3) (1994) 855-857
  

  An X-ray analysis of oraposide, previously reported as orobanchoside and isolated from Orobanche rapum-genistae confirms the originality of an unusual cyclic structure formed by an ether linkage between a glucose molecule and a 3,4-dihydroxyphenylglycol.

  Orobanchaceae, X-ray analysis, oraposide, Orobanche rapum-genistae, orobanchoside

  Publication DOI: 10.1016/S0031-9422(00)90370-4
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Laboratoire de Botanique, Phytochimie et Mycologie, Faculté de Pharmacie, Montpellier, France, EP 51, CNRS, Faculté de Pharmacie, Montpellier, France, Laboratoire de Physique Moléculaire et Structurale, Faculté de Pharmacie, Montpellier, France, UMR 9955 INSERM-CNRS, Faculté de Pharmacie, Montpellier cedex, France, URA 1111, CNRS, Faculté de Pharmacie, Montpellier, France, Faculty of Pharmaceutical Sciences, Higashi-Nippon-Gakuen University, Tobetsu, Japan
  Methods: 13C NMR, 1H NMR, X-ray, extraction, CC
  
   
  
  (plant)
  CSDB ID 64704 (all data & tools)
• Article ID: 12048
  Calvo MI, Crespo A, Fernández M "Seasonal variations of the iridoids, flavonoids and verbascoside content from Verbena officinalis L" - Acta Horticulture 516(516) (2000) 169-176
  

  The aim of this work is the quantitative determinations of iridoids, flavonoids and verbascoside by HPLC in leaves of Verbena officinalis during three vegetative periods. The effects of plant age, date of harvest, type of soil, climate, as well as a comparision between two different locations, Ilundain and Lezaun, are been investigated in order to evaluate the development and content of major compounds in Verbena leaves, verbenalin mainly, because it is the active principle. The highest amount of iridoids and flavonoids was found in the leaves during the pre-flowering period. After flowering the total compound content in the leaves decreases, whereas verbascoside content increases. The amount of iridoids and phenolic components are increasing by the years. Verbenalin content is greater in Lezaun than in Ilundain every vegetative cycle.

  HPLC, flavonoids, Verbenaceae, verbascoside, Iridoids, Verbena officinalis, experimental field, verbenalin

  Publication DOI: 10.17660/ActaHortic.2000.516.20
  Institutions: Institut de pharmacognosie et phytochimie, Ecole de Pharmacie, Université de Lausanne, Lausanne, Switzerland, Dpto. Farmacia y Tecnologiá Farmaceútica (Farmacognosia), Facultad de Farmacia, Universidad de Navarra, Pamplona, Spain
  Methods: HPLC, UV, extraction, derivatization, evaporation
  
   
  
  Verbena officinalis
  CSDB ID 64987 (all data & tools)
• Article ID: 12079
  Wei X-M, Zhu Q-X, Chen J-C, Cheng D-L "Two new iridoid glucosides from Clerodenrum serratum" - Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao = Chemical Journal of Chinese Universities [Chinese] 21(11) (2000) 1675-1678
  

  Four compounds were obtained from the leaves of Clerodendrum serratum. By means of spectroscopic techniques(such as IR, UV, MS, 1H NMR , 13C NMR and 2D-NMR) and chemical evidences, their structures were elucidated as 7-O-p-coumaroyloxyugandoside(1), 7-O-cinnamoyloxyugandoside(2), acteoside(3) and martynoside(4) respectively. Compounds 1 and 2 were new iridoid glucosides, compunds 3 and 4 were phenylpropanoid glycosides which were obtained for the first time from this plant.

  2D-NMR, phenylpropanoid glycoside, Verbenaceae, iridoid glucoside, Clerodendrum serratum, Clerodenrum

  Journal NLM ID: 101279494
  WWW link: http://www.cjcu.jlu.edu.cn/EN/Y2000/V21/I11/1675
  Publisher: Changchun, China
  Institutions: Department of Chemistry, National Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, China
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, IR, UV, CC, melting point determination
  
   
  
  Clerodenrum serratum
  CSDB ID 65116 (all data & tools)
• Article ID: 12104
  Daels-Rakotoarison DA, Seidel V, Gressier B, Brunet C, Tillequin F, Bailleul F, Luyckx M, Dine T, Cazin M, Cazin JC "Neurosedative and antioxidant activities of phenylpropanoids from Ballota nigra" - Arzneimittel-Forschung 50(1) (2000) 16-23
  

  Ballota nigra is a European plant known for its neurosedative properties. In this study, the ability of five phenylpropanoids (verbascoside, forsythoside B, arenarioside, ballotetroside, and caffeoyl malic acid) isolated from a hydroalcoholic extract, to bind to benzodiazepine, dopaminergic, and morphinic receptors was investigated. To carry out these studies, affinity tests with rat striata, entire brains and receptor rich preparations were employed. In addition, the phenolic aspect of these five phenylpropanoid esters led to investigate antioxidant activities using cell-free experiments and cellular experiments including isolated polymorphonuclear neutrophils (PMN). Effects of phenylpropanoid esters against reactive oxygen species as superoxide anion, peroxide hydrogen, hypochlorous acid and hydroxyl radical were tested. These molecules are liberated by PMN during inflammatory disorders, so that reproduction of this process in vitro stimulating PMN by chemical stimulants was undertaken. Results show that four of the five compounds are able to bind to the studied receptors. Inhibitory concentrations at 50% were determined and vary from 0.4 to 4.7 mg/ml. This may be in relation with the Ballota nigra known neurosedative activities. Results concerning antioxidant investigations evidence an ability to scavenge reactive oxygen species. Inhibitory concentrations at 50% obtained are comparable to those of known antioxidant drugs (mesna or N-acetyl cysteine). Moreover, the use of different stimuli having various pathways of action on PMN oxidative metabolism permits to establish that each phenylpropanoid ester has its own particular way of action by using proteine kinase C or phospholipase C pathways.

  reactive oxygen species, Antioxidant activity, phenylpropanoids, Ballota nigra, neurosedative activity

  NCBI PubMed ID: 10683711
  Publication DOI: 10.1055/s-0031-1300158
  Journal NLM ID: 0372660
  Publisher: Aulendorf, Editio Cantor
  Institutions: Laboratoire de Pharmacologie et Pharmacie Clinique, Faculté des Sciences Pharmaceutiques et Biologiques, Lille, France, Laboratoire de Pharmacognosie, Faculté des Sciences Pharmaceutiques et Biologiques, Lille, France, Laboratoire de Pharmacognosie, Unité de Recherche Associée (URA) au Centre National de Recherches Scientifiques (CNRS) 1310, Université de Paris Vc, Paris, France
  Methods: 13C NMR, 1H NMR, MS, extraction, CC, enzymatic assay, antioxidant activities, cytotoxicity assay, spectrophotometry, derivatization, evaporation, affinity assay
  
   
  
  Ballota nigra
  CSDB ID 65201 (all data & tools)
• Article ID: 12117
  Deepak M, Handa SS "Quantitative determination of the major constituents of Verbena officinalis using high performance thin layer chromatography and high pressure liquid chromatography" - Phytochemical Analysis 11(6) (2000) 351-355
  

  A pentacyclic triterpenoid, ursolic acid (1), two iridoid glucosides, verbenalin (2) and hastatoside (3), and a phenylpropanoid glycoside, verbascoside (4), were isolated from Verbena officinalis Linn. (Verbenaceae), a plant listed in the Chinese Pharmacopoeia and the British Herbal Pharmacopoeia. A procedure for the optimised extraction of these constituents for quantitative estimations has been established. An HPTLC method was employed for the determination of 1 using Liebermann Burchard reagent. A reversed-phase HPLC system with photodiode array detector was used to resolve compounds 2, 3 and 4 in the methanol extracts of different parts of the plant. Tender parts of the plant were rich in all of these constituents (0.24–0.34%, w/w) while the roots, which are not official in the Pharmacopoeias, contained a maximum amount (0.32%, w/w) of the bioactive verbascoside (4). The assay methods described are simple, rapid and accurate, and may form part of future drug authentication protocols.

  anti-inflammatory, ursolic acid, Verbenaceae, verbascoside, high pressure liquid chromatography, Verbena officinalis, verbenalin, high performance thin layer chromatography, hastatoside

  Publication DOI: 10.1002/1099-1565(200011/12)11:6<351::AID-PCA544>3.0.CO;2-S
  Journal NLM ID: 9200492
  Publisher: Chichester, Sussex, UK: Wiley
  Correspondence: Handa SS
  Institutions: Regional Research Laboratory (C.S.I.R.), Jammu, India
  Methods: IR, NMR, MS, HPLC, UV, extraction, HPTLC, CC, precipitation, evaporation, PTLC
  
   
  
  Verbena officinalis
  CSDB ID 65263 (all data & tools)
• Article ID: 12118
  Deepak M, Handa SS "Antiinflammatory activity and chemical composition of extracts of Verbena officinalis" - Phytotherapy Research 14(6) (2000) 463-465
  

  n an attempt to locate the biologically active fraction(s) of the plant Verbena officinalis Linn. (Verbenaceae), a preliminary screening of successive petroleum ether, chloroform and methanol extracts of aerial parts for antiinflammatory activity using carrageenan paw oedema model was carried out. All three extracts were found to exhibit antiinflammatory activity with the chloroform extract being the most active. Chemical investigations of petroleum ether and chloroform extracts led to the isolation of β-sitosterol, ursolic acid, oleanolic acid, 3-epiursolic acid, 3-epioleanolic acid, and minor triterpenoids of derivatives of ursolic acid and oleanolic acids. Chromatographic purification of the methanol extract yielded two iridoid glucosides, verbenalin and hastatoside, a phenylpropanoid glycoside, verbascoside and β-sitosterol-D-glucoside.

  β-sitosterol, ursolic acid, oleanolic acid, Verbenaceae, verbascoside, Verbena officinalis, verbenalin, hastatoside, antiinflammatory, oedema inhibition, 3-epiursolic acid, 3-epioleanolic acid, β-sitosterol-D-glucoside

  NCBI PubMed ID: 10960904
  Publication DOI: 10.1002/1099-1573(200009)14:6<463::aid-ptr611>3.0.co;2-g
  Journal NLM ID: 8904486
  Publisher: Chichester: Wiley
  Correspondence: Handa SS
  Institutions: Regional Research Laboratory (C.S.I.R.), Jammu, India
  Methods: 13C NMR, 1H NMR, biological assays, MS, HPLC, extraction, HPTLC, CC, evaporation, anti-inflammatory assays
  
   
  
  Verbena officinalis
  CSDB ID 65267 (all data & tools)
• Article ID: 12161
  Ersöz T, Berkman MZ, Tasdemir D, Ireland CM, Calis I "An iridoid glucoside from Euphrasia pectinata" - Journal of Natural Products 63(10) (2000) 1449-1450
  

  A new iridoid glucoside, 5β,6β-dihydroxyboschnaloside (1), was isolated from the aerial parts of Euphrasia pectinata. Five known iridoid glucosides, 6β-hydroxyboschnaloside (2), aucubin, euphroside, plantarenaloside, and geniposidic acid, and two known phenylethanoid glycosides, verbascoside (= acteoside) and leucosceptoside A, were also obtained and characterized. The structure of compound 1 was established by spectroscopic evidence.

  spectroscopy, iridoid glycoside, aerial parts, Euphrasia pectinata

  NCBI PubMed ID: 11076577
  Publication DOI: 10.1021/np000185n
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: tersoz@domi.com.tr
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Department of Medicinal Chemistry, College of Pharmacy, University of Utah, Salt Lake City, USA
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, ESI-MS, extraction, optical rotation measurement, CC, evaporation, MPLC, HR-FAB-MS, VLC
  
   
  
  Euphrasia pectinata
  CSDB ID 65418 (all data & tools)
• Article ID: 12178
  Franzyk H, Jensen SR, Olsen CE, Quiroga JM "A 9-hydroxyiridoid isolated from Junellia seriphioides (Verbenaceae)" - Organic Letters 2(5) (2000) 699-700
  

  An unusual iridoid glucoside, namely 9-hydroxy-8-epihastatoside (1), was isolated from Junellia seriphioides (Verbenaceae), together with the known compounds auroside (2), pulchelloside I (3), and 8-epihastatoside (4) as well as verbascoside.

  glucoside, iridoid, Junellia seriphioides, 9-hydroxy-8-epihastatoside

  NCBI PubMed ID: 10814413
  Publication DOI: 10.1021/ol0055521
  Journal NLM ID: 100890393
  Publisher: American Chemical Society
  Correspondence: Jensen SR
  Institutions: Department of Organic Chemistry, The Technical University of Denmark, Lyngby, Denmark, Department of Chemistry, The Royal Danish Agricultural and Veterinary University, Frederiksberg, Denmark, Centro Nacional Patagónico, CONICET, Chubut, Argentina
  Methods: 13C NMR, 1H NMR, FAB-MS, extraction, optical rotation measurement
  
   
  
  Junellia seriphioides
  CSDB ID 65499 (all data & tools)
• Article ID: 12188
  De Santos Galindez J, Diaz-Lanza AM, Matellano LF, Sánchez AR "A new phenylpropanoid glycoside isolated from Scrophularia scorodonia L." - Magnetic Resonance in Chemistry 38(8) (2000) 688-691
  

  A new phenylpropanoid glycoside, angoroside D, was isolated from the roots of Scrophularia scorodonia. Its structure was elucidated on the basis of spectral data as 3,4-dihydroxy-β-phenylethoxy-O-α-L-arabinopyranosyl-(1→6)-α-L-rhamnopyranosyl-(1→3)-4-O-feruloyl-β-D-glucopyranoside. Additionally, three known glycosides, angoroside A, verbascoside and isoacteoside, were isolated and identified.

  NMR, 13C NMR, 1H NMR, Scrophularia scorodonia, angoroside D

  Publication DOI: 10.1002/1097-458X(200008)38:8<688::AID-MRC714>3.0.CO;2-5
  Journal NLM ID: 9882600
  Publisher: Wiley Heyden
  Correspondence: tfamdl@farma.alcala.es
  Institutions: Laboratorio de Farmacognosia, Departamento de Farmacología, Facultad de Farmacia, Universidad de Alcalá de Henares, Alcalá de Henares, Spain, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Madrid, Spain
  Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, LSI-MS, extraction, optical rotation measurement, evaporation, MPLC, flash chromatography
  
   
  
  Scrophularia scorodonia
  CSDB ID 65553 (all data & tools)
• Article ID: 12226
  He Z-D, Lau KM-, Xu H-X, Li P-C, Pui-Hay But P "Antioxidant activity of phenylethanoid glycosides from Brandisia hancei" - Journal of Ethnopharmacology 71(3) (2000) 483-486
  

  Brandisia hancei is a medicinal herb in China. The ethanol extract of this plant and four phenylethanoid glycosides, acteoside (1), 2'-acetylacteoside (2), poliumoside (3) and brandioside (4), isolated from it were shown to have inhibitory effects on free radical-induced hemolysis of red blood cells and free radical scavenging activities in vitro. Brandioside (4) and poliumoside (3) showed stronger antioxidant effect than acteoside (1), 2'-acetylacteoside (2) and trolox.

  Antioxidant, phenylethanoid glycoside, Scrophulariaceae, Brandisia hancei

  NCBI PubMed ID: 10940587
  Publication DOI: 10.1016/s0378-8741(00)00189-6
  Journal NLM ID: 7903310
  Publisher: Limerick: Elsevier Sequoia
  Correspondence: paulbut@cuhk.edu.hk
  Institutions: Institute of Chinese Medicine and Department of Biology, The Chinese Uni6ersity of Hong Kong, Shatin, Hong Kong, China
  Methods: biological assays, colorimetry, extraction, chromatography, antioxidant activity test
  
   
  
  Brandisia hancei
  CSDB ID 65747 (all data & tools)
• Article ID: 12285
  Kim SN, Lee JY, Kim HJ, Shin C-G, Park H, Lee YS "Synthesis and HIV-1 integrase inhibitory activities of caffeoylglucosides" - Bioorganic and Medicinal Chemistry Letters 10(16) (2000) 1879-1882
  

  Caffeoylglucosides, which have a glucose ring as a central linker, were synthesized from methyl D-glucosides, and their anti-HIV-1 activities were tested. Among them, four dicaffeoylglucosides (IC50 = 29.1+/-35.1 μM), 6a, 6b, 9b and 10b, showed HIV-1 integrase inhibitory activity as potent as L-chicoric acid.

  NCBI PubMed ID: 10969990
  Publication DOI: 10.1016/s0960-894x(00)00355-3
  Journal NLM ID: 9107377
  Publisher: Elsevier
  Correspondence: Lee YS
  Institutions: Division of Life Sciences, Korea Institute of Science and Technology, Seoul, South Korea, Department of Biotechnology, Chung Ang University, An-Sung, South Korea
  Methods: inhibition studies, biological assays
  
   
  
  Clerodendron trichotomum
  CSDB ID 65987 (all data & tools)
• Article ID: 12289
  Kimura Y, Okuda H, Nishibe S, Arichi S "Effects of caffeoylglycosides on arachidonate metabolism in leukocytes" - Planta Medica 53(2) (1987) 148-153
  

  The effects of caffeoylglycosides (forsythiaside, suspensaside, acteoside, and β-hydroxyacteoside), isolated from dried fruits of Forsythia species, on the formations of the 5-lipoxygenase products 5-hydroxy-6,8,11,14-eicosatetraenoic acid (5-HETE) and leukotriene B4 (LTB4), the 15-lipoxygenase product 15-hydroxy-5,8,11,13-eicosastetraenoic acid (15-HETE) and the cyclooxygenase products 12-hydroxy-5,8,10-heptadecatrienoic acid (HHT), thromboxane B2 and 6-keto-PGF1α in rat peritoneal cells and human peripheral polymorphonuclear leukocytes were studied. Forsythiaside, suspensaside, acteoside, and β-hydroxyacteoside were found to inhibit selectively the formation of the 5-lipoxygenase products 5-HETE and LTB4 in human peripheral polymorphonuclear leukocytes; their concentrations for 50% inhibition (IC50) of 5-HETE formation being 1.92, 49.0, 4.85, and 40.0 µM, and their IC50 values for LTB4 formation being 1.01, 8.85, 2.93, and 8.50 µM, respectively. Forsythiaside, suspensaside, acteoside, and β-hydroxyacteoside inhibited the formation of 5-HETE from arachidonic acid in rat peritoneal cells, their IC50 values on its formation being 2.50, 7.97, 5.27, and 19.3 µM, respectively. Forsythiaside caused non-competitive inhibition of 5-HETE formation.

  caffeoylglycosides, leukocytes, arachidonate metabolism, Forsythia

  NCBI PubMed ID: 3110811
  Publication DOI: 10.1055/s-2006-962658
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan, 2nd Department of Medical Biochemistry, School of Medicine, Ehime University, Shigenobu-cho, Japan, The Research Institute of Oriental Medicine, Kinki University, Sayama-cho, Japan
  Methods: TLC, biological assays, extraction, microscopy, isotopic labeling, antioxidant activities, sonication, centrifugation, optical density measurement
  
   
  
  Forsythia suspensa, Forsythia viridissima
  CSDB ID 66005 (all data & tools)
• Article ID: 12363
  Li Y-M, Jiang S-H, Gao W-Y, Zhu D-Y "Phenylpropanoid glycosides from Scrophularia ningpoensis" - Phytochemistry 54(8) (2000) 923-925
  

  Three phenylpropanoid glycosides named ningposides A (3-O-acetyl-2-O-feruloyl-α-L-rhamnopyranose), B (4-O-acetyl-2-O-feruloyl-α-L-rhamnopyranose) and C (3-O-acetyl-2-O-p-hydroxycinnamoyl-α-L-rhamnopyranose) along with the known compounds sibirioside A, cistanoside D, angoroside C, acteoside, decaffeoylacteoside and cistanoside F were obtained from the roots of Scrophularia ningpoensis.

  glycoside, C, Scrophulariaceae, phenylpropanoid, B, Scrophularia ningpoensis, ningposides A

  NCBI PubMed ID: 11014290
  Publication DOI: 10.1016/s0031-9422(00)00171-0
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: dyzhu@mail.shcnc.ac.cn
  Institutions: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China
  
   
  
  Scrophularia ningpoensis
  CSDB ID 66306 (all data & tools)
• Article ID: 12397
  Kamel MS, Mohamed KM, Hassanean HA, Ohtani K, Kasai R, Yamasaki K "Iridoid and megastigmane glycosides from Phlomis aurea" - Phytochemistry 55(4) (2000) 353-357
  

  From the leaves of Phlomis aurea, two new iridoids of unique structures named 3-epiphlomurin (1) and phlomurin (2), a new megastigmane glucoside phlomuroside (3) and a new benzyl alcohol glycoside having the structure benzyl alcohol-O-β-xylopyranosyl-(1→2)-β-glucopyranoside (4) have been isolated together with four known iridoids auroside, lamiide, 8-epiloganin and ipolamiide, two known phenolic glycosides acteoside (verbascoside) and syringin, one known phenylethanoid glycoside 2-phenylethyl-O-β-xylopyranosyl-(1→2)-β-glucopyranoside, one known lignan liriodendrin and three known flavonoids chrysoeriol-7-O-β-glucopyranoside, acacetin-7-O-β-glucopyranoside and luteolin-7-O-β-glucopyranoside. The structures of the isolated compounds were verified by means of mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectral analyses.

  Lamiaceae, Iridoids, Phlomis aurea, megastigmane, benzyl alcohol glycosides

  NCBI PubMed ID: 11117884
  Publication DOI: 10.1016/s0031-9422(00)00331-9
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: mkamel@mailcity.com
  Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut, Egypt
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, extraction, optical rotation measurement, CC, MPLC, HR-FAB-MS
  
   
  
  Phlomis aurea
  CSDB ID 66489 (all data & tools)
• Article ID: 12436
  Mahato SB "Chemistry of some natural products of biological interest" - Book: Studies in Natural Products Chemistry (series: Bioactive Natural Products) (2000) Vol. 23, Chapter D, 487-529
  

  Chemistry of some natural products of biological interest is reviewed. Cleomeolide, a diterpene lactone with unprecedented structural features is isolable in quantity from renewable regions of Cleome icosandra widely distributed in India. Its chemical convertibility to a tricarboxylic system analogous to that found in taxane indicated its potential for use as a base material for the synthesis of taxol analogues. Novel triterpene acids isolable by acid hydrolysis of the saponins from Mimusops elengi are potential bioactive compounds. Acaciasides A, B and C, the acylated triterpenoid bisglycosides from the pericarps of Acacia auriculiformis, abundantly available throughout India hold promise for their use as spermicidal and antifilarial agents. Unambiguous structure elucidation of four new saponins from Bacopa monniera reputed for its use as a nervine tonic for memory improvement has been achieved and presence of at least eight other saponins has been confirmed. The results disprove the prevailing notion of occurrence in the plant of only bacoside A1 and bacoside A3. Saikosaponins are biologically interesting compounds reported so far from Bupleurum species. Saikosaponins-like glycosides corchorusins A, B, C, D, C1, D1, D2 and D3 have been isolated from Corchorus acutangulus, a plant of different genus and family occurring throughout the hotter parts of India. Interesting acid-catalysed rearrangemednts of some aglyeones are described. Spermidine and spermine alkaloids which belong to the class of polyamine conjugates possess diverse biochemical profiles. Three spermidine alkaloids, Caesalpinines A, B and C have been isolated from the prickly scandent shrub growing in eastern India. Caesalpinine A possessses a novel skeleton of a 13-membered lactum ring fused to a five-membered lactum ring. Flavonoid-, and phenylpropanoid glycosides from polar fraction of Lantana camara widely occurring in many tropical and subtropical parts of the world are of interst for their use for therapeutic intervention in a wide range of diseases including cancer.

  Publication DOI: 10.1016/S1572-5995(00)80136-2
  Publisher: New York: Elsevier
  Editors: Atta-ur-Rahman
  Institutions: Indian Institute of Chemical Biology, Jadavpur, Calcutta, India
  
   
  
  Lantana camara
  CSDB ID 66685 (all data & tools)
• Article ID: 12538
  Nishibe S, Sasahara M, Miyageta M, Noro Y, Kawamura T, Tanaka T "Studies on the methods for chemical identification of Forsythiae Fructus and Plantaginis Herba" - Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 110(6) (1990) 453-456
  

  For Forsythia Fructus (fruits of Forsythia suspensa/F. viridissima/F. viridissima var. koreana): upon reaction with 4-aminoantipyrine, a distinctive red colour is formed, due to the phenylethanoid glycosides forsythiaside and acteoside; with hydroxyamine and FeCl3, a distinctive reddish purple colour is obtained, due to the lignan arctigenin; with H2SO4, a distinctive red colour is developed, due to the lignan phillyrin. The 3 origins of Forsythia Fructus are distinguishable by the different colour reactions of their lignans. Identification of Plantaginis Herba (Plantago asiatica [P. major]) may be based on detection of plantamajoside, by TLC or colour reaction with 4-aminoantipyrine

  Publication DOI: 10.1248/YAKUSHI1947.110.6_453
  Journal NLM ID: 0413613
  Publisher: Tokyo: Nihon Yakugakkai
  Institutions: Faculty of Pharmacy, Meijo University, Nagoya, Japan, Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan, Gifu Pharmaceutical University, Mitahara-higashi, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
  
   
  
  Forsythia suspensa, Forsythia viridissima, Forsythia koreana
  CSDB ID 67126 (all data & tools)
• Article ID: 12539
  Nishibe S, Sasahara M, Ying J, Lu YC, Tanaka T "Phenylethanoid glycosides from Plantago depressa" - Phytochemistry 32(4) (1993) 975-977
  

  The five known phenylethanoid glycosides, cistanoside F, β-hydroxyacteoside, campenoside I, acteoside and orobanchoside, and a new phenylethanoid glycoside, β-oxoacteoside, were isolated from the aerial parts of Plantago depressa. The structure of β-oxoacteoside was deduced from chemical and spectral evidence to be β-oxo-β-(3,4-dihydroxyphenyl)-ethyl-O-α-L-rhamnopyranosyl-(1→3)-β-D-(4-O-caffeoyl)-glucopyranoside.

  Plantaginaceae, phenylethanoid glycosides, Plantago depressa, β-oxoacteoside

  Publication DOI: 10.1016/0031-9422(93)85238-M
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Gifu Pharmaceutical University, Mitahora-higashi, Japan, Faculty of Pharmaceutical Sciences, Higashi-Nippon-Gakuen-University, Ishikari-Tobetsu, Japan, Department of Traditional Chinese Materia Medica, Liaoning College of Traditional Chinese Medicine, Shenyang, China
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
  
   
  
  Plantago depressa
  CSDB ID 67131 (all data & tools)
• Article ID: 12541
  Nishibe S "Bioactive phenolic compounds in traditional medicines" - Pure and Applied Chemistry 66(10-11) (1994) 2263-2266
  

  Bioactive phenolic compounds in traditional medicines were investigated. Arctigenin, matairesinol, trachelogenin and nortrachelogenin from Caulis Trachelospermi, mauritianin from Herba Catharanthi, plantamajoside, acteoside and plantaginin from Plantago Herb, suspensaside, forsythiaside and (+)-pinoresinol O-β-D-glucoside from Forsythia Fruit, and (+)-syringaresinol di-O-β-D-glucoside from Eleutherococcus, were respectively isolated and subjected to assays for their biological activities.

  Publication DOI: 10.1351/pac199466102263
  Journal NLM ID: 0376514
  Publisher: Oxford: Blackwell Scientific Publications
  Institutions: Faculty of Pharmaceutical Sciences, Higashi-Nippon-Gakuen-University, Ishikari-Tobetsu, Japan
  
   
  
  Plantago depressa, Plantago lanceolata
  CSDB ID 67146 (all data & tools)
• Article ID: 12593
  Pedersen JA "Distribution and taxonomic implications of some phenolics in the family Lamiaceae determined by ESR spectroscopy" - Biochemical Systematics and Ecology 28(3) (2000) 229-253
  

  The dihydric phenolics from the leaves of 365 specimens representing 355 species and varieties of 110 genera of Lamiaceae (Labiatae) have been examined as semiquinones by ESR spectroscopy. Of these 89 genera comprising 194 species belong to the Lamiaceae, whereas 21 genera comprising 161 species have been transferred from the Verbenaceae in the most recent classification. Two chemical characters give strong support to the subfamily division of the Lamiaceae as recognised by Erdtman (1945). (Svensk Bot. Tidskr. 29, 279–285) and others. Rosmarinic acid was observed in 110 species out of 127 studied and confined to the subfamily Nepetoideae sensu Erdtman. These species produce tricolpate pollen grains. 3,4- Dihydroxyphenylethanoid glycosides were observed in 111 species all confined to Lamioideae sensu Erdtman with hexacolpate pollen grains. The acid and the phenylethanoid glycosides were found to be mutually exclusive, apart from one species, Teucrium scorodonia. A compound tentatively assigned as a β-hydroxy-(3,4-dihydroxyphenyl) ethanoid glycoside, was observed in 49 species, solely confined to subfamily Lamioideae. Furthermore, rosmarinic acid was observed in Aegiphila mollis and in Hymenopyramis brachiata, both belonging to Lamioideae. No phenylethanoid glycosides were observed from any of 5 Hymenopyramis or from any of 30 species of Vitex. The latter result questions the transfer of the genus to Lamiaceae, but strengthens its isolated position. Chlorogenic acid was observed in 34 species and protochatechuic acid in 16 species. Hydroquinone is scattered in the family (4 species) and thymohydroquinone was observed in 7 species all belong to the Nepetoideae.

  Lamiaceae; Verbenaceae; rosmarinic and chlorogenic acid; dihydroxy-phenylethanoid glycosides; phenolics; ESR; pollen morphology; chemotaxonomy

  Publication DOI: 10.1016/S0305-1978(99)00058-7
  Journal NLM ID: 0430442
  Publisher: Pergamon Press
  Correspondence: jap@kemi.aau.dk
  Institutions: University of British Columbia, Department of Botany, Vancouver, Canada
  
   
  
  (plant)
  CSDB ID 67335 (all data & tools)
• Article ID: 12598
  Pieroni A, Pachaly P, Huang Y, Van Poel B, Vlietinck AJ "Studies on anti-complementary activity of extracts and isolated flavones from Ligustrum vulgare and Phillyrea latifolia leaves (Oleaceae)" - Journal of Ethnopharmacology 70(3) (2000) 213-217
  

  Polar fractions and flavones isolated from methanolic extracts of the leaves of Ligustrum vulgare and Phillyrea latifolia (Oleaceae), whose popular use as an anti-inflammatory is well-known in Mediterranean historical medicine and ethnobotany, showed significant in vitro complement inhibiting effect on the classical pathway of the complement system. Among the isolated flavonoidic structures, apigenin-7-O-glucoside, apigenin-7-O-rutinoside, luteolin-4'-O-glucoside, luteolin-7-O-glucoside and ligustroflavone presented remarkable activity.

  Ligustrum vulgare; Phillyrea latifolia; mediterranean ethnomedicine; flavones; anti-complementary activity

  NCBI PubMed ID: 10837985
  Publication DOI: 10.1016/s0378-8741(99)00169-5
  Journal NLM ID: 7903310
  Publisher: Limerick: Elsevier Sequoia
  Correspondence: Pieroni A
  Institutions: Department of Pharmaceutical Sciences, University of Antwerp (UIA), Antwerp, Belgium, Pharmazeutisches Institut der Rheinischen Friedrich-Wilhelms-Universität Bonn, Bonn, Germany, Dipartimento di Scienza del Suolo e Nutrizione della Pianta, Università degli Studi di Firenze, Firenze, Italy
  Methods: inhibition studies, HPLC, extraction
  
   
  
  Phillyrea latifolia
  CSDB ID 67361 (all data & tools)
• Article ID: 12613
  Ravn H, Nishibe S, Sasahara M, Xuebo L "Phenolic compounds from Plantago asiatica" - Phytochemistry 29(11) (1990) 3627-3631
  

  The four known phenolic compounds, 3,4-dihydroxyphenethyl alcohol-6-O-caffeoyl-β-d-glucoside, acteoside (verbascoside), plantaginin and plantamajoside, and a new phenylpropanoid glycoside, hellicoside, were isolated from the aerial parts of Plantago asiatica, which is used in oriental medicine ‘Plantaginis Herba’. The structure of hellicoside was deduced from chemical and spectral evidence to be 3,4,7-trihydroxy-β-phenethyl-O-β-d-glucopyranosyl-(1 → 3)-4-O-caffeoyl-β-d-glucopyranoside. Plantamajoside and hellicoside showed high inhibition of cyclic AMP phosphodiesterase and 5-lipoxygenase. Acteoside showed high inhibition of lens aldose reductase.

  13C NMR, phenylpropanoid glycoside, phenolic compound, Plantaginaceae, Plantago asiatica, Plantaginis Herba, hellicoside, enzyme inhibitory activity

  Publication DOI: 10.1016/0031-9422(90)85289-R
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan, Royal Danish School of Pharmacy, Department of Pharmacognosy and Botany, Copenhagen, Denmark
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, acid hydrolysis, HPLC, extraction, evaporation
  
   
  
  Plantago asiatica
  CSDB ID 67437 (all data & tools)
• Article ID: 12622
  Rønsted N, Gøbel E, Franzyk H, Jensen SR, Olsen CE "Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides" - Phytochemistry 55(4) (2000) 337-348
  

  Data for 34 species of Plantago (Plantaginaceae), including subgen. Littorella (= Littorella uniflora), have been collected with regard to their content of iridoid glucosides and caffeoyl phenylethanoid glycosides (CPGs). In the present work, 21 species were investigated for the first time and many known compounds were found together with three new iridoid glucosides. Of these, arborescoside and arborescosidic acid, both of the uncommon type with an 8,9-double bond, were present in several species, while 6-deoxymelittoside was found only in P. subulata. The known compounds deoxyloganic acid, caryoptoside and rehmannioside D were isolated from the genus for the first time. The earlier reported occurrence of sorbitol in the family was confirmed, and this compound was shown by NMR spectroscopy to be the main sugar in the three species investigated for this. The combined data show that CPGs are present in all species investigated. With regard to the iridoids, the distribution patterns showed a good correlation with the classification of Rahn. Thus, aucubin is typical for the whole genus, while bartsioside and catalpol as well as 5-substituted iridoids are each characteristic for a subgenus in the family. Finally, the close relationship between Plantago and Veronica suggested by chloroplast DNA sequence analysis. could be corroborated by the common occurrence of the rare 8,9-unsaturated iridoids in these two genera.

  Plantago; Plantaginaceae; chemotaxonomy; iridoid glucosides; bartsioside; aucubin; catalpol; arborescoside; arborescosidic acid; 6-deoxymelittoside; verbascoside; sorbitol

  NCBI PubMed ID: 11117882
  Publication DOI: 10.1016/s0031-9422(00)00306-x
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: Jensen SR
  Institutions: Department of Organic Chemistry, The Technical University of Denmark, Lyngby, Denmark, Department of Chemistry, The Royal Veterinary and Agricultural University, Frederiksberg, Denmark
  Methods: 13C NMR, 1H NMR, extraction, CC, MT: extraction
  
   
  
  Plantago afra (NT: Plantago psyllium), Plantago arborescens, Plantago atrata, Plantago australis, Plantago bellardii, Plantago coronopus, Plantago cretica, Plantago lundborgii, Plantago nivalis, Plantago ovata, Plantago patagonica, Plantago raoulii, Plantago reniformis, Plantago sempervirens, Plantago stauntonii, Plantago subspathulata, Plantago subulata, Plantago uniflora (NT: Littorella uniflora), Plantago webbii, Plantago alpina, Plantago arenaria, Plantago asiatica, Plantago hookeriana, Plantago lagopus, Plantago lanceolata, Plantago major, Plantago myosuros
  CSDB ID 67504 (all data & tools)
• Article ID: 12647
  Samuelsen AB "The traditional uses, chemical constituents and biological activities of Plantago major L. A review" - Journal of Ethnopharmacology 71(1-2) (2000) 1-21
  

  Plantago major L. leaves have been used as a wound healing remedy for centuries in almost all parts of the world and in the treatment of a number of diseases apart from wound healing. These include diseases related to the skin, respiratory organs, digestive organs, reproduction, the circulation, against cancer, for pain relief and against infections. P. major contains biologically active compounds such as polysaccharides, lipids, caffeic acid derivatives, flavonoids, iridoid glycosides and terpenoids. Alkaloids and some organic acids have also been detected. A range of biological activities has been found from plant extracts including wound healing activity, anti-inflammatory, analgesic, antioxidant, weak antibiotic, immuno modulating and antiulcerogenic activity. Some of these effects may attribute to the use of this plant in folk medicine.

  traditional uses; chemical constituents; biological activities; Plantago major L

  NCBI PubMed ID: 10904143
  Publication DOI: 10.1016/s0378-8741(00)00212-9
  Journal NLM ID: 7903310
  Publisher: Limerick: Elsevier Sequoia
  Correspondence: a.b.samuelsen@farmasi.uio.no
  Institutions: Department of Pharmacognosy, School of Pharmacy, University of Oslo, Oslo, Norway
  
   
  
  Plantago major
  CSDB ID 67652 (all data & tools)
• Article ID: 12674
  Seidel V, Verholle M, Malard Y, Tillequin F, Fruchart J-C, Duriez P, Bailleul F, Teissier E "Phenylpropanoids from Ballota nigra L. inhibit in vitro LDL peroxidation" - Phytotherapy Research 14(2) (2000) 93-98
  

  From the European plant Ballota nigra L. various polyphenols including phenylpropanoid derivatives were isolated. There is increasing evidence that oxidized low-density lipoproteins (Ox-LDL) might be involved in the pathogenesis of atherosclerosis and it has been reported that polyphenols inhibit LDL peroxidation and atherogenesis. The goal of this study was to test whether the major polyphenolic compounds extracted from Ballota nigra, four phenylpropanoid glycosides, verbascoside, forsythoside B, arenarioside, and ballotetroside and one non-glycosidic phenylpropanoid, caffeoyl-L-malic acid, inhibit Cu2+-induced LDL peroxidation. The effectiveness of these compounds was compared to the activity of quercetin, a well-known polyphenol inhibitor of Cu2+-induced LDL oxidation. Antioxidant efficacious doses (ED 50) of arenarioside and ballotetroside were 1.8 µM and 7.5 µM respectively, while in the same conditions, the ED 50 of forsythoside B and verbascoside were similar (1 µM) and those of quercetin and of caffeoyl-L-malic acid were 2.3 µM and 9.5 µM respectively. Spectrophotometric studies show that quercetin is a Cu2+ chelator while phenylpropanoid glycosides and caffeoyl-L-malic acid are not Cu2+ chelators. Therefore, phenylpropanoid glycosides are strong inhibitors of Cu2+-induced LDL oxidation, independent of any capacity to act as Cu2+ chelators.

  Ballota nigra; phenylpropanoids; oxidized-LDL

  NCBI PubMed ID: 10685104
  Publication DOI: 10.1002/(sici)1099-1573(200003)14:2<93::aid-ptr558>3.0.co;2-x
  Journal NLM ID: 8904486
  Publisher: Chichester: Wiley
  Correspondence: patrick.duriez@pasteur-lille.fr
  Institutions: Laboratoire de Pharmacognosie, Faculté de Pharmacie, Université de Lille 2, Lille, France, Département d' Athérosclérose, INSERM U325, Institut Pasteur de Lille et Faculté de Pharmacie, Université de Lille 2, Lille, France, Laboratoire de Pharmacognosie, Faculté de Pharmacie, URA au CNRS 1310, Université de Paris V, Paris, France
  
   
  
  Ballota nigra
  CSDB ID 67825 (all data & tools)
• Article ID: 12751
  Tattini M, Gravano E, Pinelli P, Mulinacci N, Romani A "Flavonoids accumulate in leaves and glandular trichomes of Phillyrea latifolia exposed to excess solar radiation" - New Phytologist 148(1) (2000) 69-77
  

  Experiments were conducted on Phillyrea latifolia plants grown under a dense overstorey of Pinus pinea (shade plants) or on seashore dunes (sun plants) in a coastal area of Tuscany (42° 46′ N, 10° 53′ E). Total integrated photon flux densities averaged 1.67 and 61.4 m mol/m^2/d for shade and sun sites, respectively. A leaf morphological–structural analysis, a qualitative and quantitative analysis of phenylpropanoids of leaf tissue and leaf surface, and a histochemical localization of flavonoids were conducted. The area of sun leaves reached 57% of that of shade leaves, whereas leaf angle (β), sclerophylly index (ratio of leaf d. wt:leaf area), and trichome frequency (trichome number mm−2 ) were markedly greater in leaves exposed to full solar radiation than in leaves acclimated to shade. The total thickness of sun leaves was 78% higher than that of shade leaves, mostly owing to a greater development of both palisade parenchyma and spongy mesophyll. The concentration, but not the composition, of leaf tissue phenylpropanoids varied significantly between sun and shade leaves, with a marked increase in flavonoid glycosides in sun leaves. Flavonoids occurred almost exclusively in the upper epidermal cells of shade leaves. By contrast, flavonoids largely accumulated in the upper and lower epidermis, as well as in the mesophyll tissue of leaves that were acclimated to full sunlight. Flavonoid glycosides were found exclusively in the secretory products of glandular trichomes of P. latifolia leaves exposed to high levels of light; luteolin 7-O- glucoside and quercetin 3-O-rutinoside were the major constituents. By contrast, verbascoside and an unidentified caffeic acid derivative constituted 72% of total phenylpropanoids secreted by glandular trichomes of shade leaves, whereas they were not detected in glandular trichomes of sun leaves. These findings suggest that the light-induced synthesis of flavonoids in glandular trichomes of P. latifolia probably occurs in situ and concomitantly inactivates other branch pathways of the general phenylpropanoid metabolism. This is the first report of the key role of glandular trichomes and of flavonoid glycosides in the integrated mechanisms of acclimation of P. latifolia to excess light.

  phenylpropanoids, flavonol glycosides, Oleaceae, fluorescence microscopy, glandular trichomes

  NCBI PubMed ID: 33863030
  Publication DOI: 10.1046/j.1469-8137.2000.00743.x
  Journal NLM ID: 9882884
  Publisher: Blackwell Publishing
  Correspondence: tattini@ipsl.fi.cnr.it
  Institutions: Dipartimento di Scienze Farmaceutiche, Università di Firenze, Florence, Italy, Istituto sulla Propagazione delle Specie Legnose - Consiglio Nazionale delle Ricerche, Scandicci, Italy, Dipartimento di Biologia Vegetale, Università di Firenze, Florence, Italy
  Methods: ESI-MS, HPLC, UV, extraction, HPTLC, HPLC-MS, spectrophotometry
  
   
  
  Phillyrea latifolia
  CSDB ID 68167 (all data & tools)
• Article ID: 12836
  Xiong Q, Tezuka Y, Kaneko T, Li H, Tran LQ, Hase K, Namba T, Kadota S "Inhibition of nitric oxide by phenylethanoids in activated macrophages" - European Journal of Pharmacology 400(1) (2000) 137-144
  

  Nitric oxide (NO) is one of the pro-inflammatory molecules. Some phenylethanoids have been previously shown to possess anti-inflammatory effects. Seven phenylethanoids from the stems of Cistanche deserticola, viz. isoacteoside, tubuloside B, acteoside, 2′-O-acetylacteoside, echinacoside, cistanoside A and tubuloside A, were tested for their effect on NO radical generation by activated murine macrophages. At the concentration of 100–200 μM, all the phenylethanoids reduced (6.3–62.3%) nitrite accumulation in lipopolysaccharide (0.1 μg/ml)-stimulated J774.1 cells. At 200 μM, they inhibited by 32.2–72.4% nitrite accumulation induced by lipopolysaccharide (0.1 μg/ml)/interferon-γ (100 U/ml) in mouse peritoneal exudate macrophages. However, these compounds did not affect the expression of inducible nitric oxide (iNOS) mRNA, the iNOS protein level, or the iNOS activity in lipopolysaccharide-stimulated J774.1 cells. Instead, they showed a clear scavenging effect (6.9–43.9%) at the low concentrations of 2–10 μM of about 12 μM nitrite generated from an NO donor, 1-propanamine-3-hydroxy-2-nitroso-1-propylhydrazino (PAPA NONOate). These results indicate that the phenylethanoids have NO radical-scavenging activity, which possibly contributes to their anti-inflammatory effects.

  macrophage, phenylethanoid, nitric oxide (NO), nitric oxide (NO) synthase, inducible, 1-propanamine-3-hydroxy-2-nitroso-1-propylhydrazino (PAPA NONOate)

  NCBI PubMed ID: 10913595
  Publication DOI: 10.1016/s0014-2999(00)00354-x
  Journal NLM ID: 1254354
  Publisher: Amsterdam: Elsevier
  Correspondence: kadota@ms.toyama-mpu.ac.jp
  Institutions: Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
  Methods: biological assays
  
   
  
  Cistanche deserticola
  CSDB ID 68646 (all data & tools)
• Article ID: 12850
  Yang H, Jiang B, Hou A-J, Lin Z-W, Sun H-D "Colebroside A, a new diglucoside of fatty acid ester of glycerin from Clerodendrum colebrookianum" - Journal of Asian Natural Products Research 2(3) (2000) 177-185
  

  Colebroside A (1), a new diglucoside of fatty acid ester of glycerin, was isolated from the aerial parts of Clerodendrum colebrookianum Walp., along with nine known compounds (2-10). Their structures were elucidated by spectroscopic and chemical methods. Compounds 2, 3, 4, 5, 7, 8, 9 and 10 have been obtained from this plant for the first time.

  Clerodendrum colebrookianum Walp.; Verbenaceae; diglucoside of fatty acid ester of glycerin; colebroside A (1)

  NCBI PubMed ID: 11256691
  Publication DOI: 10.1080/10286020008039909
  Journal NLM ID: 100888334
  Publisher: Harwood Academic Publishers; London: Informa Healthcare
  Correspondence: hdsun@mail.kib.ac.cn
  Institutions: Laboratory of Phytochemistry, Kunming Institute of Botany, Academia Sinica, Kunming, China, Chemistry Department, College of Life Science and Chemistry, Yunnan University, Kunming, China
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
  
   
  
  Clerodendrum colebrookianum
  CSDB ID 68727 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: arenarioside
Compound class: glycoside, phenolic glycoside, phenylethanoid glycoside, phenylpropanoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_189517,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 11504
  Yamamoto H, Yoshida K, Kondo Y, Inoue K "Production of cornoside in Abeliophyllum distichum cell suspension cultures" - Phytochemistry 48(2) (1998) 273-277
  

  The production of phenylethanoid derivatives in callus and cell suspension cultures of four oleaceous plants, Abeliophyllum distichum, Forsythia suspensa, F. viridissima, and F. koreana was investigated. Of two types of A. distichum cultured cells, the friable fine cells produced only the 4-hydroxyphenylethanoid-type glucoside, cornoside, whereas the small cell aggregates produced the 3,4-dihydroxyphenylethanoid-type glycosides (i.e. verbascoside) predominantly. In the cultured cells of F. suspensa and F. viridissima, the latter-type glycosides were produced predominantly and from those of F. koreana, lignan glucosides with 3,4-dioxygenated phenyl groups were isolated.

  production, Forsythia suspensa, Oleaceae, cornoside, Abeliophyllum distichum, benzoquinolethanoid glucoside, cell suspension cultures, F. koreana, F. viridissima, phenylethanoid glycosides

  Publication DOI: 10.1016/S0031-9422(97)01134-5
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Pharmacognosy, Gifu Pharmaceutical University, Gifu, Japan
  Methods: extraction, CC, RP-HPLC
  
   
  
  Abeliophyllum distichum
  CSDB ID 62155 (all data & tools)
• Article ID: 11761
  Didry N, Seidel V, Dubreuil L, Tillequin F, Bailleul F "Isolation and antibacterial activity of phenylpropanoid derivatives from Ballota nigra" - Journal of Ethnopharmacology 67(2) (1999) 197-202
  

  In addition to the previously isolated phenylpropanoid glycosides verbascoside 1, forsythoside B 2, arenarioside 3 and ballotetroside 4, another four compounds were isolated from generative aerial parts of Ballota nigra: three phenylpropanoid glycosides, alyssonoside 5, lavandulifolioside 6 and angoroside A 7 and a non-glycosidic derivative (+)-(E)-caffeoyl-L-malic acid 8. The antibacterial activity of the five major compounds (1-4 and 8) was tested against Gram-positive and Gram-negative bacteria. Three of them (1-3) exhibited a moderate antimicrobial activity against Proteus mirabilis and Staphylococcus aureus including one methicillin-resistant strain.

  antimicrobial activity, Ballota nigra, phenylpropanoid non-glycosidic ester, phenylpropanoid glycosidic esters

  NCBI PubMed ID: 10619384
  Publication DOI: 10.1016/S0378-8741(99)00019-7
  Journal NLM ID: 7903310
  Publisher: Limerick: Elsevier Sequoia
  Institutions: Laboratoire de Pharmacognosie, Faculté des Sciences Pharmaceutiques et Biologiques, B.P. 83, 59006 Lille Cedex, France, Laboratoire de Bactériologie, Faculté des Sciences Pharmaceutiques et Biologiques, B.P. 83, 59006 Lille Cedex, France, Laboratoire de Pharmacognosie, Faculté des Sciences Pharmaceutiques et Biologiques, U.R.A. au C.N.R.S. no. 1310, 4, Avenue de l’Observatoire, 75006 Paris, France
  Methods: 13C NMR, 1H NMR, TLC, colorimetry, optical rotation measurement, acetylation, antibacterial assay, COSY, HETCOR, COLOC
  
   
  
  Ballota nigra
  CSDB ID 62802 (all data & tools)
• Article ID: 11800
  Kong LD, Wolfender JL, Cheng CHK, Hostettmann K, Tan RX "Xanthine oxidase inhibitors from Brandisia hancei" - Planta Medica 65(8) (1999) 744-746
  

  Xanthine oxidase is a key enzyme associated with the incidence of hyperuricemia-related disorders. Repeated chromatography of the enzyme inhibitory part of the water extract of the twigs and leaves of Brandisia hancei (Scrophulariaceae) gave a flavone luteolin, an iridoid glycoside mussaenoside, two β-sitosterol glycosides daucosterol and β-sitosterol gentiobioside, and five phenylethanoids arenarioside, brandioside, acteoside, 2'-O-acetylacteoside and isoacteoside. Luteolin and isoacteoside inhibited the xanthine oxidase (XO, EC 1.2.3.2) with the IC50 values at 7.83 and 45.48 μM, respectively. Isoacteoside was found to be the first phenylethanoid that decreased substantially the formation of uric acid by inhibiting competitively xanthine oxidase (K(i) value: 10.08 μM). Furthermore, the study suggested that the caffeoylation of the 6'-hydroxyl group of the phenylethanoids was essential for the enzyme inhibitory action.

  inhibitor, Brandisia hancei, xanthine oxidase

  NCBI PubMed ID: 10630118
  Publication DOI: 10.1055/s-2006-960854
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: Tan RX
  Institutions: Department of Biochemistry, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong, China, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Science, Nanjing University, Nanjing, China, Institute of Pharmacognosy & Phytochemistry, School of Pharmacy, University of Lausanne, BEP, Lausanne-Dorigny, Switzerland
  Methods: 13C NMR, 1H NMR, FAB-MS, inhibition studies, TLC, MS, HPLC, UV, optical rotation measurement, HMBC, HMQC, DEPT, COSY, LC-UV
  
   
  
  Brandisia hancei
  CSDB ID 63026 (all data & tools)
• Article ID: 12104
  Daels-Rakotoarison DA, Seidel V, Gressier B, Brunet C, Tillequin F, Bailleul F, Luyckx M, Dine T, Cazin M, Cazin JC "Neurosedative and antioxidant activities of phenylpropanoids from Ballota nigra" - Arzneimittel-Forschung 50(1) (2000) 16-23
  

  Ballota nigra is a European plant known for its neurosedative properties. In this study, the ability of five phenylpropanoids (verbascoside, forsythoside B, arenarioside, ballotetroside, and caffeoyl malic acid) isolated from a hydroalcoholic extract, to bind to benzodiazepine, dopaminergic, and morphinic receptors was investigated. To carry out these studies, affinity tests with rat striata, entire brains and receptor rich preparations were employed. In addition, the phenolic aspect of these five phenylpropanoid esters led to investigate antioxidant activities using cell-free experiments and cellular experiments including isolated polymorphonuclear neutrophils (PMN). Effects of phenylpropanoid esters against reactive oxygen species as superoxide anion, peroxide hydrogen, hypochlorous acid and hydroxyl radical were tested. These molecules are liberated by PMN during inflammatory disorders, so that reproduction of this process in vitro stimulating PMN by chemical stimulants was undertaken. Results show that four of the five compounds are able to bind to the studied receptors. Inhibitory concentrations at 50% were determined and vary from 0.4 to 4.7 mg/ml. This may be in relation with the Ballota nigra known neurosedative activities. Results concerning antioxidant investigations evidence an ability to scavenge reactive oxygen species. Inhibitory concentrations at 50% obtained are comparable to those of known antioxidant drugs (mesna or N-acetyl cysteine). Moreover, the use of different stimuli having various pathways of action on PMN oxidative metabolism permits to establish that each phenylpropanoid ester has its own particular way of action by using proteine kinase C or phospholipase C pathways.

  reactive oxygen species, Antioxidant activity, phenylpropanoids, Ballota nigra, neurosedative activity

  NCBI PubMed ID: 10683711
  Publication DOI: 10.1055/s-0031-1300158
  Journal NLM ID: 0372660
  Publisher: Aulendorf, Editio Cantor
  Institutions: Laboratoire de Pharmacologie et Pharmacie Clinique, Faculté des Sciences Pharmaceutiques et Biologiques, Lille, France, Laboratoire de Pharmacognosie, Faculté des Sciences Pharmaceutiques et Biologiques, Lille, France, Laboratoire de Pharmacognosie, Unité de Recherche Associée (URA) au Centre National de Recherches Scientifiques (CNRS) 1310, Université de Paris Vc, Paris, France
  Methods: 13C NMR, 1H NMR, MS, extraction, CC, enzymatic assay, antioxidant activities, cytotoxicity assay, spectrophotometry, derivatization, evaporation, affinity assay
  
   
  
  Ballota nigra
  CSDB ID 65203 (all data & tools)
• Article ID: 12674
  Seidel V, Verholle M, Malard Y, Tillequin F, Fruchart J-C, Duriez P, Bailleul F, Teissier E "Phenylpropanoids from Ballota nigra L. inhibit in vitro LDL peroxidation" - Phytotherapy Research 14(2) (2000) 93-98
  

  From the European plant Ballota nigra L. various polyphenols including phenylpropanoid derivatives were isolated. There is increasing evidence that oxidized low-density lipoproteins (Ox-LDL) might be involved in the pathogenesis of atherosclerosis and it has been reported that polyphenols inhibit LDL peroxidation and atherogenesis. The goal of this study was to test whether the major polyphenolic compounds extracted from Ballota nigra, four phenylpropanoid glycosides, verbascoside, forsythoside B, arenarioside, and ballotetroside and one non-glycosidic phenylpropanoid, caffeoyl-L-malic acid, inhibit Cu2+-induced LDL peroxidation. The effectiveness of these compounds was compared to the activity of quercetin, a well-known polyphenol inhibitor of Cu2+-induced LDL oxidation. Antioxidant efficacious doses (ED 50) of arenarioside and ballotetroside were 1.8 µM and 7.5 µM respectively, while in the same conditions, the ED 50 of forsythoside B and verbascoside were similar (1 µM) and those of quercetin and of caffeoyl-L-malic acid were 2.3 µM and 9.5 µM respectively. Spectrophotometric studies show that quercetin is a Cu2+ chelator while phenylpropanoid glycosides and caffeoyl-L-malic acid are not Cu2+ chelators. Therefore, phenylpropanoid glycosides are strong inhibitors of Cu2+-induced LDL oxidation, independent of any capacity to act as Cu2+ chelators.

  Ballota nigra; phenylpropanoids; oxidized-LDL

  NCBI PubMed ID: 10685104
  Publication DOI: 10.1002/(sici)1099-1573(200003)14:2<93::aid-ptr558>3.0.co;2-x
  Journal NLM ID: 8904486
  Publisher: Chichester: Wiley
  Correspondence: patrick.duriez@pasteur-lille.fr
  Institutions: Laboratoire de Pharmacognosie, Faculté de Pharmacie, Université de Lille 2, Lille, France, Département d' Athérosclérose, INSERM U325, Institut Pasteur de Lille et Faculté de Pharmacie, Université de Lille 2, Lille, France, Laboratoire de Pharmacognosie, Faculté de Pharmacie, URA au CNRS 1310, Université de Paris V, Paris, France
  
   
  
  Ballota nigra
  CSDB ID 67827 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: cornoside
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11504
  Yamamoto H, Yoshida K, Kondo Y, Inoue K "Production of cornoside in Abeliophyllum distichum cell suspension cultures" - Phytochemistry 48(2) (1998) 273-277
  

  The production of phenylethanoid derivatives in callus and cell suspension cultures of four oleaceous plants, Abeliophyllum distichum, Forsythia suspensa, F. viridissima, and F. koreana was investigated. Of two types of A. distichum cultured cells, the friable fine cells produced only the 4-hydroxyphenylethanoid-type glucoside, cornoside, whereas the small cell aggregates produced the 3,4-dihydroxyphenylethanoid-type glycosides (i.e. verbascoside) predominantly. In the cultured cells of F. suspensa and F. viridissima, the latter-type glycosides were produced predominantly and from those of F. koreana, lignan glucosides with 3,4-dioxygenated phenyl groups were isolated.

  production, Forsythia suspensa, Oleaceae, cornoside, Abeliophyllum distichum, benzoquinolethanoid glucoside, cell suspension cultures, F. koreana, F. viridissima, phenylethanoid glycosides

  Publication DOI: 10.1016/S0031-9422(97)01134-5
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Pharmacognosy, Gifu Pharmaceutical University, Gifu, Japan
  Methods: extraction, CC, RP-HPLC
  
   
  
  Forsythia viridissima, Abeliophyllum distichum
  CSDB ID 62156 (all data & tools)
• Article ID: 12386
  Jensen SR "Chemical relationships of Polypremum procumbens, Tetrachondra hamiltonii and Peltanthera floribunda" - Biochemical Systematics and Ecology 28(1) (2000) 45-51
  

  Polypremum procumbens (Buddlejaceae) was found to contain sorbitol, cornoside, salidroside and conandroside. One collection of Peltanthera floribunda (Buddlejaceae) contained verbascoside, two others the cornoside-derived rengyolone (=halleridone). From Tetrachondra hamiltonii (Tetrachondraceae) was isolated sorbitol, cornoside and verbascoside. Iridoids were not found in any of the taxa. The taxonomic significance of the different chemical constituents is discussed, and the data demonstrate a close relationship between Polypremum and Tetrachondra. They may also suggest an inclusion of Peltanthera in Gesneriaceae. These findings are in concert with recently published chloroplast DNA sequence data.

  chemotaxonomy, cornoside, verbascoside, Polypremum procumbens, Peltanthera floribunda, Buddlejaceae, Tetrachondra hamiltonii, Tetrachondraceae, sorbitol, conandroside, rengyolone

  Publication DOI: 10.1016/S0305-1978(99)00040-X
  Journal NLM ID: 0430442
  Publisher: Pergamon Press
  Correspondence: oksrj@pop.dtu.dk
  Institutions: Department of Organic Chemistry, The Technical University of Denmark, Lyngby, Denmark
  Methods: 13C NMR, 1H NMR, extraction, CC, evaporation
  
   
  
  Polypremum procumbens, Tetrachondra hamiltonii
  CSDB ID 66442 (all data & tools)