| Identification | Back Directory | [Name]
2-BUTENOIC ACID, 2-METHYL-, (5S,6S,7S,13AS)-5,6,7,13A-TETRAHYDRO-6-HYDROXY-1,2,3,13-TETRAMETHOXY-6,7-DIMETHYLBENZO[3,4]CYCLOOCTA[1,2-F][1,3]BENZODIOXOL-5-YL ESTER, (2Z)- | [CAS]
58546-55-7 | [Synonyms]
GOMISINB
Schizantherin B
Wuweizi ester B
SCHISANTHERIN B
Schisantherin B (Gomisin-B
SCHISANTHERIN B 98.0% BY HPLC
(5S)-5,6,7,8-Tetrahydro-1,2,3,13-tetramethoxy-6,7β-dimethylbenzo[3,4]cycloocta[1,2-f][1,3]benzodioxole-5α,6β-diol 5-[(Z)-2-methyl-2-butenoate]
(5S)-6α,7β-Dimethyl-1,2,3,12-tetramethoxy-10,11-methylenedioxy(5,6,7,8-tetrahydrodibenzo[a,c]cyclooctene)-5α,6β-diol 5-[(Z)-2-methyl-2-butenoate]
(5S,6S,7S)-6-Hydroxy-1,2,3,13-tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3',4']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxol-5-yl (Z)-2-methylbut-2-enoate
(2Z)-2-Methyl-2-butenoic acid(5S,6S,7S,13aS)-5,6,7,8-tetrahydro-6-hydroxy-1,2,3,13-tetramethoxy-6,7-dimethylbenzo[3,4]cycloocta[1,2-f][1,3]benzodioxol-5-yl ester
2-Butenoic acid, 2-methyl-, (5S,6S,7S,13aS)-5,6,7,8-tetrahydro-6-hydroxy-1,2,3,13-tetramethoxy-6,7-dimethylbenzo[3,4]cycloocta[1,2-f][1,3]benzodioxol-5-yl ester, (2Z)-
2-BUTENOIC ACID, 2-METHYL-, (5S,6S,7S,13AS)-5,6,7,13A-TETRAHYDRO-6-HYDROXY-1,2,3,13-TETRAMETHOXY-6,7-DIMETHYLBENZO[3,4]CYCLOOCTA[1,2-F][1,3]BENZODIOXOL-5-YL ESTER, (2Z)-
2-BUTENOIC ACID, 2-METHYL-, (5S,6S,7S,13AS)-5,6,7,13A-TETRAHYDRO-6-HYDROXY-1,2,3,13-TETRAMETHOXY-6,7-DIMETHYLBENZO[3,4]CYCLOOCTA[1,2-F][1,3]BENZODIOXOL-5-YL ESTER, (2Z)- USP/EP/BP | [Molecular Formula]
C28H34O9 | [MDL Number]
MFCD08460221 | [MOL File]
58546-55-7.mol | [Molecular Weight]
514.56 |
| Chemical Properties | Back Directory | [Boiling point ]
638.6±55.0 °C(Predicted) | [density ]
1.28 | [storage temp. ]
Refrigerator | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
13.54±0.60(Predicted) | [color ]
White to Off-White | [InChIKey]
BKGUPIVDQHHVMV-WMUMBSKPNA-N | [SMILES]
C(O[C@@H]1[C@](O)(C)[C@@H](C)CC2=C(C3=C(OC)C(OC)=C(OC)C=C31)C(OC)=C1OCOC1=C2)(=O)/C(/C)=C\C |&1:2,3,6,r| |
| Hazard Information | Back Directory | [Description]
Schisantherin B (STB) is a lignan originally isolated from S. sphenanthera fruit.1 It inhibits formation of advanced glycation end products (AGEs) in vitro.2 STB (0.1 mg/kg) decreases escape latency in the Morris water maze and increases spontaneous alternation in the Y-maze in a mouse model of Alzheimer''s disease induced by amyloid-β (1-42) (Item No. 20574).3 It increases glial expression of glutamate transporter 1 (GLP-1) and decreases immobility time in the forced swim test (FST) in mice, indicating antidepressant-like activity.4 STB also increases spontaneous alternation in the Y-maze in a mouse model of stress-induced short-term learning impairment induced by the FST. | [Uses]
Schisantherin B is a bioactive of lignans isolated from Schisandra chinesis which protect against cognitive deficits and neurodegeneration induced by Aβ1-42 in mice. | [Definition]
ChEBI:Gomisin B is a tannin. | [target]
P450 (e.g. CYP17) | GSK-3 | Beta Amyloid | [References]
[1] C S LIU. Studies on the active principles of Schisandra sphenanthera Rehd. et Wils. The structures of schisantherin A, B, C, D, E, and the related compounds.[J]. Scientia Sinica, 1978, 21 4: 483-502.
[2] B. POORNIMA . Advanced glycation end-products inhibitors isolated from Schisandra grandiflora[J]. Natural Product Research, 2016, 30 4: Pages 493-496. DOI: 10.1080/14786419.2015.1024117
[3] MENGJIE XU . Schisantherin B ameliorates Aβ1–42-induced cognitive decline via restoration of GLT-1 in a mouse model of Alzheimer’s disease[J]. Physiology & Behavior, 2016, 167: Pages 265-273. DOI: 10.1016/j.physbeh.2016.09.018
[4] MENGJIE XU. Schisantherin B Improves the Pathological Manifestations of Mice Caused by Behavior Desperation in Different Ages-Depression with Cognitive Impairment.[J]. Biomolecules & Therapeutics, 2019, 27 2: 160-167. DOI: 10.4062/biomolther.2018.074 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
2-BUTENOIC ACID, 2-METHYL-, (5S,6S,7S,13AS)-5,6,7,13A-TETRAHYDRO-6-HYDROXY-1,2,3,13-TETRAMETHOXY-6,7-DIMETHYLBENZO[3,4]CYCLOOCTA[1,2-F][1,3]BENZODIOXOL-5-YL ESTER, (2Z)-(58546-55-7)1HNMR
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