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Structure type: monomer
C₂₇H₃₄O₁₁
Trivial name: arctiin
Compound class: glycoside, lignan glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8874
  Dong M, Ma Z, Yang Q, Hu Q, Ye Y, Zhou M "A new pericarbonyl lignan from Amauroderma rude" - Records of Natural Products 13(4) (2019) 296-300
  

  A new pericarbonyl lignan (1), named amaurolignan A was isolated from an ethanol extract of the fruiting bodies in Amauroderma rude of family Ganodermataceae, together with two known lignans, 4-methoxymatairesinol 4′-β-D-glucoside (2) and lappaol F (3). The structures of compounds (1-3) were elucidated using NMR and MS spectroscopic methods.

  pericarbonyl lignan, amaurolignan A, Amauroderma rude

  Publication DOI: 10.25135/rnp.115.18.10.1007
  Journal NLM ID: 101479886
  Publisher: Turkey: ACG Publications
  Correspondence: Zhou M
  Institutions: Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University, Kunming, China, School of Chemistry and Environment, Yunnan Minzu University, Kunming, China
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, UV, extraction, CC, HR-ESI-MS
  
   
  
  Amauroderma rude
  CSDB ID 49609 (all data & tools)
• Article ID: 12256
  Inagaki I, Hisada S, Nishibe S "On the constituents of Trachelospermum asiaticum Nakai var. intermedium Nakai" - Chemical and Pharmaceutical Bulletin 16(11) (1968) 2307-2308
  

  tracheloside, trachelogenin, Trachelospermum asiaticum

  Publication DOI: 10.1248/cpb.16.2307
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan
  Methods: 1H NMR, IR, TLC, UV, optical rotation measurement, elemental analysis, melting point determination
  
   
  
  Trachelospermum asiaticum var. intermedium
  CSDB ID 65911 (all data & tools)
• Article ID: 12257
  Inagaki I, Hisada S, Nishibe S "Lignan glycosides of Trachelospermum asiaticum var. intermedium" - Phytochemistry 10(1) (1971) 211-213
  

  Matairesinol-4′-β-D-glucoside (matairesinoside) and tracheloside have been isolated from the stem of Trachelospermum asiaticum var. intermedium. The structure of tracheloside is discussed.

  tracheloside, Trachelospermum asiaticum, matairesinol

  Publication DOI: 10.1016/S0031-9422(00)90274-7
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan
  Methods: 1H NMR, methylation, IR, TLC, MS, UV, extraction, elemental analysis, melting point determination, evaporation, permanganate oxidation
  
   
  
  Trachelospermum asiaticum var. intermedium
  CSDB ID 65913 (all data & tools)
• Article ID: 12370
  Inagaki I, Hisada S, Nishibe S "Lignans of Trachelospermum asiaticum var. intermedium. I. Isolation and structures of arctiin, matairesinoside and tracheloside" - Chemical and Pharmaceutical Bulletin 20(12) (1972) 2710-2718
  

  As the components of the stems of Trachelospermum asiaticum NAKAI var. intermedium NAKAI, arctiin (I), matairesinoside(VI) and tracheloside(VIII) were isolated. VI was elucidated as 4, 4'-dihydroxy-3, 3'-dimethoxy-lignan-olid(9, 9')-4'-β-D-glucopyranoside. In addition the formula of VIII established by T.Takano, et al. as C36H50O18 was reexamined and revised to C27H34O12·1/2H2O. VIII gave trachelogenin(X), C21H24O7, mp 139-141° and D-glucose by acid or emulsin hydrolysis. From chemical and physical data structure of X was proposed as 4', 8'-dihydroxy-3, 4, 3'-trimethoxy-lignan-olid(9, 9')(Xa) or 4, 8'-dihydroxy-3, 3', 4'-trimethoxylignan-olid(9, 9')(Xb). In this paper structure of methyltranchelogenin(XI) with absolute configuration was determined to be 8(S), 8'(S)-8'-dihydroxy-3, 4, 3', 4'-tetramethoxy-lignan-olid(9, 9'). Now we suggest two possible structures for VIII; 8(S), 8'(S)-4', 8'-dihydroxy-3, 4, 3', -trimethoxy-lignan-olid(9, 9')-4'-β-D-glucopyranoside(VIIIa) or 8(S), 8'(S)-4, 8'-dihydroxy-3, 3', 4'-trimethoxy-lignan-olid(9, 9')-4-β-D-glucopyranoside(VIIIb).

  lignans, tracheloside, Trachelospermum asiaticum, arctiin, matairesinoside

  Publication DOI: 10.1248/cpb.20.2710
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Nagoya University, Nagoya, Japan
  Methods: 1H NMR, methylation, IR, TLC, acid hydrolysis, GLC, paper chromatography, UV, extraction, optical rotation measurement, acetylation, elemental analysis, reduction, ethylation, CC, melting point determination, evaporation, permanganate oxidation
  
   
  
  Trachelospermum asiaticum var. intermedium
  CSDB ID 66333 (all data & tools)
• Article ID: 12525
  Nikaido T, Ohmoto T, Kinoshita T, Sankawa U, Nishibe S, Hisada S "Inhibition of cyclic AMP phosphodiesterase by lignans" - Chemical and Pharmaceutical Bulletin 29(12) (1981) 3586-3592
  

  Cyclic adenosine monophosphate (AMP) phosphodiesterase inhibitors contained in Forsythia suspensa were identified as lignans, (+)-pinoresinol (Ia) and (+)-pinoresinol-β-D-glucoside (Id), and their structure-activity relationship was investigated. In pinoresinol congeners, the configuration of the two phenyl rings is very important in relation to the activity. When both of the p-hydroxyl groups in matairesinol congeners are substituted by methyl or glucose, the activities are decreased as compared with those of the unsubstituted compounds.

  inhibitors, Forsythia suspensa, lignans, cAMP phosphodiesterase, (+)-pinoresinol, (+)-pinoresinol-β-D-glucoside, (-)-matairesinol

  NCBI PubMed ID: 6280885
  Publication DOI: 10.1248/cpb.29.3586
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, University of Tokyo, Tokyo, Japan, Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan, Faculty of Pharmaceutical Sciences, Toho University, Funabashi, Japan
  Methods: inhibition studies, biological assays
  
   
  
  Forsythia viridissima
  CSDB ID 67082 (all data & tools)
• Article ID: 12526
  Nishibe S, Hisada S, Inagaki I "Structures of tracheloside and nortracheloside from Trachelospermum asiaticum Nakai var. intermedium Nakai" - Chemical and Pharmaceutical Bulletin 19(4) (1971) 866-868
  

  tracheloside, Trachelospermum asiaticum var. intermedium, nortracheloside

  Publication DOI: 10.1248/cpb.19.866
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
  
   
  
  Trachelospermum asiaticum var. intermedium
  CSDB ID 67087 (all data & tools)
• Article ID: 12528
  Nishibe S, Hisada S, Inagaki I "Lignan diglucosides from Trachelospermum asiaticum" - Phytochemistry 11(10) (1972) 3084-3085
  

  Trachelospermum asiaticum var. intermedium; Apocynaceae; lignans; matairesinol-4, 4’-di-O-β-D-glucopyranoside; nortrachelogenin-4, 4’-di-O-β-D-glucopyranoside

  Publication DOI: 10.1016/0031-9422(72)80115-8
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
  
   
  
  Trachelospermum asiaticum var. intermedium
  CSDB ID 67094 (all data & tools)
• Article ID: 12530
  Nishibe S, Hisada S, Inagaki I "Lignans of Trachelospermum asiaticum var. intermedium. II. Structures of tracheloside and nortracheloside" - Chemical and Pharmaceutical Bulletin 21(5) (1973) 1108-1113
  

  A new lignan glucoside named nortracheloside (IV), C26H32O12·H2O, mp 95-100°, was isolated from the stems of Trachelospermum asiaticum NAKAI var. intermedium NAKAI (Apocynaceae). The lignan derivatives were prepared from tracheloside (III) and nortracheloside (IV). From the discussion of mass spectra of the lignan derivatives, the structures of III and IV were established as 8(S), 8'(S)-4', 8'-dihydroxy-3, 4, 3'-trimethoxy-lignan-olid(9, 9')4'-β-D-glucopyranoside and 8(S), 8'(S)-4, 4', 8'-trihydroxy-3, 3'-dimethoxy-lignan-olid(9, 9')4'-β-D-glucopyranoside, respectively.

  Publication DOI: 10.1248/cpb.21.1108
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
  
   
  
  Trachelospermum asiaticum var. intermedium
  CSDB ID 67100 (all data & tools)
• Article ID: 12532
  Nishibe S, Hisada S, Inagaki I "Lignans of Trachelospermum asiaticum var. intermedium. V. Isolation of nortrachelogenin-4,4'-di-O-β-glucopyranoside" - Chemical and Pharmaceutical Bulletin 21(5) (1973) 1114-1117
  

  A new lignan diglucoside was isolated from the stems of Trachelospermum asiaticum nakai var.intermedium nakai (apocynaceae) and its structure was established as nortrachelogenin-4,4'-di-O-β-D-glucopyranoside (I). Also the presence of a-conidendrin glucoside was suggested.

  Publication DOI: 10.1248/cpb.21.1114
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
  
   
  
  Trachelospermum asiaticum var. intermedium
  CSDB ID 67110 (all data & tools)
• Article ID: 12537
  Nishibe S, Tsukamoto H, Hisada S "Effects of O-methylation and O-glucosylation on carbon-13 nuclear magnetic resonance chemical shifts of matairesinol, (+)-pinoresinol and (+)-epipinoresinol" - Chemical and Pharmaceutical Bulletin 32(11) (1984) 4653-4657
  

  The effects of O-methylation and O-glucosylation on the carbon-13 nuclear magnetic resonance chemical shifts of matairesinol (1), (+)-pinoresinol (6) and (+)-epipinoresinol (11) are discussed. The chemical shifts of carbons on the 2, 3-dibenzylated butyrolactone and 2,6-diarylated 3,7-dioxabicyclo[3.3.0] octane rings are not affected by methylation and glucosylation of hydroxy groups on the aromatic rings. As regards the chemical shifts of aromatic carbons caused by O-methylation, all the 1'(1"), 3'(3"), and 4'(4") carbons of the guaiacyl unit are characteristically shifted downfield by 1.6±0.1, 1.3±0.1, and 2.4±0.1 ppm, respectively, while the 5'(5") carbons are shifted upfield by 3.5±0.1 ppm. In the case of the chemical shifts of aromatic carbons caused by O-glucosylation, all the 1'(1") and 3'(3") carbons of the guaiacyl unit are characteristically shifted downfield by 3.0±0.1 and 1.3±0.1 ppm, respectively.

  13C-NMR, lignan, matairesinol, (+)-pinoresinol, O-methylation shift, O-glucosylation shift, guaiacyl group

  Publication DOI: 10.1248/cpb.32.4653
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
  
   
  
  Forsythia suspensa
  CSDB ID 67118 (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 67124 (all data & tools)
• Article ID: 12540
  Nishibe S, Fujimoto T, Nose M, Takeda T, Ogihara Y, Xu G "Lignans from Trachelospermum axillare" - Phytochemistry 32(6) (1993) 1579-1581
  

  A new lignan, traxillaside and nine known lignans, arctigenin, traxillagenin, trachelogenin, matairesinol, nortrachelogenin, arctiin, tracheloside, matairesinoside and nortracheloside, were isolated from the bark of Trachelospermum axillare.

  Apocynaceae, bark, lignans, Trachelospermum axillare, traxillagenin, traxillaside, 2-4”-hydroxy-3”-methoxybenzyl-3-3’, 4’, 5’-trimethoxybenzylbutyrolactone-4"-O-β-D-glucopyranoside

  Publication DOI: 10.1016/0031-9422(93)85183-R
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan, Faculty of Pharmaceutical Sciences, Higashi-Nippon-Gakuen-University, Ishikari-Tobetsu, Japan, China Pharmaceutical University, Nanjing, China
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
  
   
  
  Trachelospermum axillare
  CSDB ID 67134 (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
  
   
  
  Trachelospermum jasminoides
  CSDB ID 67139 (all data & tools)
• Article ID: 12549
  Nose M, Fujimoto T, Takeda T, Nishibe S, Ogihara Y "Structural transformation of lignan compounds in rat gastrointestinal tract" - Planta Medica 58(6) (1992) 520-523
  

  Structural transformation of arctiin and tracheloside, major components of seeds of Arctium lappa and Carthamus tinctorius, were investigated using rat gastric juice (pH 1.2-1.5) and rat large intestinal flora in vitro. Quantitative analysis of lignans and their metabolites was carried out by high performance liquid chromatography. Both lignans were stable in rat gastric juice and arctiin was rapidly transformed to arctigenin in rat large intestinal flora, followed by conversion to the major metabolite, 2-(3",4"-dihydroxybenzyl)-3-(3',4'-dimethoxybenzyl)-butyrolactone. On the other hand, tracheloside also decreased dependently with time and was converted to trachelogenin and its major metabolite, 2-(3",4"-dihydroxybenzyl)-3-(3',4'-dimethoxybenzyl)-2-hydroxybutyrola ctone. These experiments suggest that in the course of metabolism of lignans, firstly a cleavage of the glycosidic bond occurred and then demethylation of the phenolic methoxy group in the alimentary tract followed.

  structural transformation, intestinal flora, tracheloside, arctiin, gastric juice

  NCBI PubMed ID: 1336605
  Publication DOI: 10.1055/s-2006-961540
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Faculty of Pharmaceutical Science, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan, Department of Pharmacognosy, Faculty of Pharmaceutical Science, Nagoya City University, Nagoya, Japan
  Methods: biological assays, HPLC
  
   
  
  Arctium lappa
  CSDB ID 67182 (all data & tools)
• Article ID: 12550
  Nose M, Fujimoto T, 0Nishibe S, Ogihara Y "Structural transformation of lignan compounds in rat gastrointestinal tract; II. Serum concentration of lignans and their metabolites" - Planta Medica 59(2) (1993) 131-134
  

  Serum concentrations of arctiin, tracheloside, and their metabolites formed in the gastrointestinal tract were investigated in the rat. Arctiin or tracheloside was not detected in the serum after oral administration (200 mg/kg). In regard to their metabolites, each metabolite 1 (AM1, TM1), their genuine genins, appeared in the serum, and the serum concentration of arctiin metabolite 1 (AM1) reached its peak at 4 h and that of tracheloside metabolite 1 (TM1) reached its peak at 8 h. On the other hand, both metabolites 2 (AM2, TM2), which each possess a catechol moiety as reported previously, were not found in the serum. Now, we have studied the detection of their metabolites in the rat large intestinal contents after oral administration. It was revealed that all metabolites reported previously were certainly formed in rat gastrointestinal tract in vivo. Thus, we presumed a possibility that metabolite 2 was converted into metabolite 1 through C-3" methylation by catechol-O-methyltransferase (COMT) in rat liver. Each metabolite 2 was incubated with rat liver cytosol in the presence of S-adenosyl-L-methionine. It was proved that metabolite 2 was rapidly converted into metabolite 1 within 3 min. We suggest that arctiin or tracheloside was transformed to at least two metabolites in the gastrointestinal tract, and after absorption from the intestine, metabolite 2 was converted into metabolite 1 through methylation by COMT in the liver, and arctiin and tracheloside existed as metabolite 1, the genuine genin, in the blood stream.

  tracheloside, arctiin, serum concentration, structural transformation in rat liver cytosol, catechol-O-methyltransferase

  NCBI PubMed ID: 8387675
  Publication DOI: 10.1055/s-2006-959627
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Faculty of Pharmaceutical Science, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan, Department of Pharmacognosy, Faculty of Pharmaceutical Science, Nagoya City University, Nagoya, Japan
  Methods: biological assays, HPLC
  
   
  
  Arctium lappa
  CSDB ID 67184 (all data & tools)