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Structure type: monomer
Trivial name: stigmasterol 3-O-β-D-glucopyranoside
Compound class: saponin glycoside, glycoside, steroid glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8697
  Elsbaey M, Sallam A, El-Metwally M, Nagata M, Tanaka C, Shimizu K, Miyamoto T "Melanogenesis inhibitors from the endophytic fungus Aspergillus amstelodami" - Chemistry and Biodiversity 16(8) (2019) ID e1900237
  

  Two new compounds, named 3,4-dimethoxyphenyl α-D-ribofuranoside (1) and 3β-(β-D-glucopyranosyloxy)olean-12-ene-23,28,30-trioic acid (2), together with thirteen known compounds, were isolated from the white beans culture of the marine derived endophytic fungus Aspergillus amstelodami. Structure elucidation of the new compounds was carried out by one-, two-dimensional spectroscopy, and high resolution electrospray ionization mass. The antimelanogenic and anti-allergic activity of the isolated compounds were investigated. Compounds 4, 7, 1, 3, 11, 6 and 9 selectively suppressed melanin production in B16 melanoma cells, using arbutin as a positive control. Their IC50 values were 30.8±5.57, 38.5±6.08, 52.6±6.64, 98.0±1.16, 100.4±3.05, 112.0±0.22 and 144.7±2.35 μm, respectively, while that of arbutin was 151.7±1.27 μm. The tested compounds did not show any significant anti-allergic activity in RBL-2H3 cells, as compared to quercetin.

  biological activity, 3, 4-dimethoxyphenyl α-D-ribofuranoside, 3β-(β-D-glucopyranosyloxy)olean-12-ene-23, 28, 30-trioic acid, Aspergillus amstelodami, B16 melanoma cells, β-hexosaminidase

  NCBI PubMed ID: 31241824
  Publication DOI: 10.1002/cbdv.201900237
  Journal NLM ID: 101197449
  Publisher: Verlag Helvetica Chimica Acta
  Correspondence: marwaelsebay1611@mans.edu.eg
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, Egypt, Department of Natural Products Chemistry, Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan, Division of Marine Environment, National Institute of Oceanography and Fisheries, Hurghada, Egypt, Department of Agro-environmental Sciences, Graduate School of Bioresource and Bioenvironmental Science, Kyushu University, Fukuoka, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, PCR, TLC, acid hydrolysis, HPLC, extraction, column chromatography, cell growth, enzymatic assay, HR-ESI-MS, cell viability assay, cytotoxicity assay, MTT
  
   
  
  Aspergillus amstelodami AUMC EGY
  CSDB ID 49612 (all data & tools)
• Article ID: 11404
  Li W, Chan CL, Leung HW, Yeung HW, Xiao P "Xanthones from Polygala caudata" - Phytochemistry 51(7) (1999) 953-958
  

  A new xanthone-O-glycoside, polycaudoside A, together with 2'-benzoylmangiferin, 1-methoxy-7-hydroxyxanthone, 1,2,8-trihydroxyxanthone, euxanthone, gentisein, wubangziside A, wubangziside B, 1,3-dihydroxy-2-methoxyxanthone, lancerin and neolancerin, stigmasterol, stigmastrol-3-O-D-glucoside, p-hydroxybenzoic acid, dihydroquercetin and quercetin were isolated from the roots of Polygala caudata. Their structures were established on the basis of chemical studies and spectral evidence, including 2D NMR analyses.

  steroids, flavonoids, roots, Polygalaceae, xanthones, Polygala caudata

  Publication DOI: 10.1016/S0031-9422(99)00059-X
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Chemistry and the Institute for the Advancement of Chinese Medicine, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100094, China
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, MS, UV, HPTLC, HMBC, HCl hydrolysis, HR-EI-MS, UV EI-MS
  
   
  
  Polygala caudata
  CSDB ID 62647 (all data & tools)
• Article ID: 11435
  Simonet AM, Stochmal A, Oleszek W, Macías FA "Saponins and polar compounds from Trifolium resupinatum" - Phytochemistry 51(8) (1999) 1065-1067
  

  In addition to the known soyasaponin I, 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→2-β-D-glucuronopyranosyl]-22-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucopyranosyl]soyasapogenol B, soyasaponin II, 3-O-β-D-glucopyranosyl sitosterol, 3-O-β-D-glucopyranosyl stigmasterol and 3-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]oct-1-ene-3-ol, the new saponin, 3-O-α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]-22-O-β-D-glucopyranosyl soyasapogenol B (2) was isolated and characterised from the seed saponins fraction of Trifolium resupinatum. The structural determination is based on spectroscopic methods (including DQF-COSY, HETCOR, TOCSY, ROESY and NOEs experiments).

  glycosides, saponins, Leguminosae, clover seeds, Persian clover, Trifolium resupinatum

  Publication DOI: 10.1016/S0031-9422(99)00192-2
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: Macías FA
  Institutions: Departamento de Quı́mica Orgánica, Facultad de Ciencias, Universidad de Cádiz, C/República Saharaui s/n, Apdo. 40, 11510-Puerto Real, Cádiz, Spain, Department of Biochemistry, Institute of Soil and Plant Cultivation, ul., Czartoryskich 8, Osada Palacowa, 24-100, Pulawy, Poland
  Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, optical rotation measurement, ROESY, TOCSY, DQF-COSY, HETCOR
  
   
  
  Trifolium resupinatum
  CSDB ID 62747 (all data & tools)
• Article ID: 11509
  Zhu M, Li RC "Receptor binding activities of Schefflera triterpenoids and oligosaccharides" - Planta Medica 65(2) (1999) 99-103
  

  Roots and leaves of Schefflera bodinieri were studied for their activity in the central nervous system (CNS) by bioassay-guided isolation in conjunction with receptor binding assays. As demonstrated in preliminary screening, ethanol extracts of leaves and roots of S. bodinieri showed strong binding affinity to a number of CNS receptors. Chemical investigation of this plant species was then conducted and fourteen plant ingredients were obtained. In this study, nine of these isolated compounds were tested by fifteen receptor binding assays for their CNS activities. Results showed that three compounds, namely bodinone, bodinone glycoside and D-sorbitol, were able to selectively bind to muscarine receptors, a trisaccharide bound to Ca2+ channel and 5HT-2 receptors, stigmasterol 3-O-glucoside bound to 5HT- 2 receptors, and bodirin A bound to dopamine-2 receptors with IC50 values at μM level. In the drug-interaction studies, bodinone, bodinone glycoside, bodirin A, bodinitin A and the trisaccharide were found to affect binding affinity of certain specific binding agents to the 5HT1C, 5HT2, opiate, β- adrenergic and histamine 1 receptors. These observations suggest interactions between the plant ingredients and receptors as well as synergistic effect of various compounds at receptor level.

  interaction, araliaceae, Schefflera bodinieri, plant ingredients, receptor binding assay

  NCBI PubMed ID: 10193197
  Publication DOI: 10.1055/s-1999-13967
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: Zhu M
  Institutions: Department of Pharmacy, Faculty of Medicine, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong, China
  Methods: NMR, HPLC, binding assays
  
   
  
  Schefflera bodinieri
  CSDB ID 63102 (all data & tools)
• Article ID: 11630
  Kovganko NV, Kashkan ZN "Sterol glycosides and acylglycosides" - Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(5) (1999) 479-497
  

  The structure, properties, distribution in nature, and biological activity of sterol glycosides and acylgylcosides are reviewed.

  biological activity, sterol glycoside, acylgylcoside

  Publication DOI: 10.1007/BF02323277
  Journal NLM ID: 0151571
  Publisher: Tashkent: Izdatelstvo Fan
  Institutions: Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus, 220141, Belarus, Minsk, Ul. Akad. Kuprevicha, 5/2, Belarus
  
   
  
  Senecio bonariensis, Prunella vulgaris
  CSDB ID 64012 (all data & tools)
• Article ID: 11637
  Ullah N, Ahmed Z, Ahmed S, Muhammad P, Malik A "A pentacyclic triterpene from Daphne oleoides" - Phytochemistry 50(5) (1999) 839-841
  

  From the whole plant extract of Daphne oleoides, a new triterpene and the known 20(30)-lupene-3,29-diol, butilin, and stigmasterol glycoside have been isolated for the first time from this source. The new triterpene was established as lup-20(30)-ene-3α, 29-diol on the basis of homonuclear 1H decoupled 13C, DEPT, 1H-13C HMQC, long range HMBC NMR spectral studies and by chemical methods.

  steroids, triterpenoids, Thymelaeaceae, Daphne oleoides, lup-20(30)-ene-3α, 29-diol

  Publication DOI: 10.1016/S0031-9422(98)00600-1
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: International Centre for Chemical Sciences, H.E.J. Research Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan
  Methods: VLC
  
   
  
  Daphne oleoides
  CSDB ID 64092 (all data & tools)
• Article ID: 11757
  Chang F-R, Chen C-Y, Hsieh T-J, Cho C-P, Wu Y-C "Chemical constituents from Annona glabra III" - Journal of the Chinese Chemical Society = Zhongguo hua hsueh hui hui zhi 47(4B) (2000) 913-920
  

  Twenty compounds including a dioxoaporphine, annobraine (1); two oxoaporphines, liriodenine (2) and lysicamine (3); five aporphines, (-)-nornuciferine (4), (-)-anonaine (5), (-)-N-formylanonaine (6), (-)-asimilobine (7) and (+)-nordomesticine (8); one proaporphine, (+)-stepharine (9); two protoberberines, (-)-kikemanine (10) and dehydrocorydalmine (11); one azaanthraquinone, 1-aza-4-methyl-2-oxo-1,2-dihydro-9,10-anthracenedione (12); two amides, N-trans-feruloyltyramine (13) and N-p-coumaroyltyramine (14); one ionone, blumenol A (15); and five steroids, β-sitosterol (16), stigmasterol (17), β-sitosteryl-D-glucoside (18), stigmasteryl-D-glucoside (19) and 6-O-palmitoyl-β-sitosteryl-D-glucoside (20), were isolated from the fruits and stems of Annona glabra. Among them, 1 is a novel dioxoaporphine alkaloid and 12 was obtained for the first time from natural sources. These compounds were characterized and identified by physical and spectral evidence.

  Annona glabra

  Publication DOI: 10.1002/jccs.200000124
  Journal NLM ID: 16210600R
  Publisher: Taipei: Chinese Chemical Society
  Institutions: Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan, China
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, UV, extraction, EI-MS, column chromatography, melting point determination, evaporation, HR-EI-MS
  
   
  
  Annona glabra
  CSDB ID 65045 (all data & tools)
• Article ID: 11808
  Debella A, Haslinger E, Schmid MG, Bucar F, Michl G, Abebe D, Kunert O "Triterpenoid saponins and sapogenin lactones from Albizia gummifera" - Phytochemistry 53(8) (2000) 885-892
  

  The structures of two new monodesmosidic and bisdesmosidic triterpenoid saponins (1 and 2) and the known compound delta 5-stigmasterol-3-O-β-D-glucopyranoside (3) as well as two new oleanane type triterpene lactone glycosides 4, 5 and a new sapogenin lactone 6 isolated from the stem bark of Albizia gummifera C.A. Smith (Mimosaceae) have been elucidated as 3-O-{β-D-glucopyranosyl(1→2)-[α-L-arabinopyranosyl(1→6)]-β-D-glucopyranosyl}-oleanolic acid (1), β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl-3-O-}β-D-glucopyranosyl(1→2)-[α-L-arabinopyrano syl(1→6)]-β-D-glucopyranosyl}-oleanolate (2), 3 β-{O-D-glucopyranosyl-(1→2)-[O-α-L-arabinopyranosyl(1→6 )] β-D-glucopyranosyloxy}-machaerinic acid gamma-lactone (4), 3β-O-β-D-glucopyranosiduronic acid (1→2)-β-D-glucopyranosyloxy]-machaerinic acid gamma-lactone (5), and A-homo-3a-oxa-5β-olean-12-en-3-one-28-oic acid (6), respectively. The complete assignment of the 1H and 13C resonances of 1, 2, 4 and 6 and of the peracetate of 5 were achieved by means of 2D-NMR studies.

  stem bark, oleanolic acid glycosides, Mimosaceae, Albizia gummifera (C.A. Smith), machaerinic acid lactone glycosides, A-homo-3a-oxa-olean-12-en-28-oic acid, stigmasterol glycoside

  NCBI PubMed ID: 10820798
  Publication DOI: 10.1016/s0031-9422(99)00464-1
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: haslinger@kfunigraaz.ac.at
  Institutions: Institut für Pharmazeutische Chemie, Universität Graz, Graz, Austria, Institut für Pharmakognosie, Universität Graz, Graz, Austria, Schering A.G., Berlin, Germany, Ethiopian Health and Nutrition Research Institute, Addis-Abeba, Ethiopia
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, GC-MS, TLC, ESI-MS, acid hydrolysis, GLC, alkaline hydrolysis, UV, extraction, optical rotation measurement, acetylation, column chromatography, melting point determination, derivatization, evaporation, capillary electrophoresis, PPC
  
   
  
  Albizia gummifera
  CSDB ID 65250 (all data & tools)
• Article ID: 11924
  Herath HM, deSilva S "New constituents from Gliricidia sepium" - Fitoterapia 71(6) (2000) 722-724
  

  The heart wood of Gliricidia sepium stem yielded stigmastanol glucoside (1) and 3',4'-dihydroxy-trans-cinnamic acid octacosylester 2, along with three other known constituents.

  triterpenes, sterols, Gliricidia sepium, 3', isoflavonoids, stigmastanol glucoside, 4'-dihydroxy-trans-cinnamic acid octacosylester

  NCBI PubMed ID: 11077187
  Publication DOI: 10.1016/s0367-326x(00)00219-7
  Journal NLM ID: 16930290R
  Publisher: Elsevier
  Correspondence: herath@ifs.ac.lk
  Institutions: Natural Products Programme, Institute of Fundamental Studies, Kandy, Sri Lanka
  Methods: 13C NMR, 1H NMR, IR, EI-MS, melting point determination
  
   
  
  Gliricidia sepium
  CSDB ID 65773 (all data & tools)
• Article ID: 12183
  Mishra M, Shukla YN, Kumar S "Euphane triterpenoid and lipid constituents from Butea monosperma" - Phytochemistry 54(8) (2000) 835-838
  

  Besides stigmasterol, stigmasterol-β-D-glucopyranoside and nonacosanoic acid, two new compounds isolated from the stems of Butea monosperma have been characterised as 3α-hydroxyeuph-25-ene and 2,14-dihydroxy-11,12-dimethyl-8-oxo-octadec-11-enylcyclohexane by spectral data and chemical studies.

  Butea monosperma; Fabaceae; 3α-hydroxyeuph-25-ene; lipids; steroids

  NCBI PubMed ID: 11014275
  Publication DOI: 10.1016/s0031-9422(00)00136-9
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: Shukla YN
  Institutions: Medicinal Plant Chemistry and Herbal Product Development Divisions, Central Institute of Medicinal and Aromatic Plants, Lucknow, India
  Methods: 13C NMR, 1H NMR, HPLC
  
   
  
  Butea monosperma
  CSDB ID 66899 (all data & tools)
• Article ID: 12263
  Ortega CA, María AOM, Gianello JC "Chemical components and biological activity of Bidens subalternans, B. aurea (Astereaceae) and Zuccagnia puntacta (Fabaceae)" - Molecules 5(3) (2000) 465-467
  

  The aim of this work was to evaluate the activity in the gastrointestinal tract of the several extracts and pure components isolated from Bidens species and Zuccagnia puntacta

  Bidens species, Zuccagnia puntacta, gastrointestinal activity

  Publication DOI: 10.3390/50300465
  Journal NLM ID: 100964009
  Publisher: Basel, Switzerland: MDPI
  Correspondence: jcgian@unsl.edu.ar
  Institutions: Química Orgánica, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, San Luis, Argentina
  Methods: 13C NMR, 1H NMR, GC-MS, biological assays, MS, extraction, column chromatography
  
   
  
  Bidens subalternans
  CSDB ID 67265 (all data & tools)
• Article ID: 12276
  Park H-J, Kwon S-H, 0 Yun S-Y, Lee K-T "Isolation of steroids and flavonoids from the herbs of Hypericum ascyron L." - Saengyak Hakhoechi = Korean journal of pharmacognosy [Korean] 31(1) (2000) 39-44
  

  A sterol mixture, 3-O-glucosides of these sterols, 6'-O-fattyacyl ester of these sterol glucosides, kaempferol, quercetin and isoquercitrin were isolated from the whole plants of Hypericum ascyron L. The sterols were found to be a mixture of β-sitosterol, campesterol and stigmasterol by GC-MS. The kinds of fatty acids linked at 6'-OH of sterol glucoside ester mixture were shown to be palmitic acid, stearic acid, oleic acid and linoleic acid by GC- MS. Three flavonoids were identified by spectroscopic methods and comparisons of mixed mp and co-TLC with authentic specimens.

  Hypericum ascyron L.; Hypericaceae; flavonoid; steroid

  Journal NLM ID: 9713418
  WWW link: https://kmbase.medric.or.kr/Main.aspx?menu=01&d=KMBASE&m=VIEW&i=0616120000310010039
  Publisher: Seoul : Hanguk Saengyak Hakhoe
  Institutions: College of Pharmacy, Kyung-Hee University, Seoul, South Korea, Division of Applied Plant Sciences, Sangji University, Wonji, South Korea
  Methods: GC-MS, extraction
  
   
  
  Hypericum ascyron
  CSDB ID 67303 (all data & tools)