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)- Chemical Properties

Boiling point:

638.6±55.0 °C(Predicted)

Density 

1.28

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

13.54±0.60(Predicted)

form 

Solid

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|

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)- Usage And Synthesis

Description

Schisantherin B (STB) is a lignan originally isolated from S. sphenanthera fruit. It inhibits formation of advanced glycation end products (AGEs) in vitro. 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) . 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. 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

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)Related Product Information

• Benzo(3,4)cycloocta(1,2-f)(1,3)benzodioxol-1-ol, 5,6,7,8-tetrahydro-2, 3,13-trimethoxy-6,7-dimethyl-, stereoisomer
• schisanhenol
• Anwuligan
• Epigomisin O
• Angeloylgomisin O
• GOMISING
• Arisanlactone D
• Angeloylgomisin H
• gomisin J
• Gomisin M2
• Gomisin A
• SCHIZANDRIN B
• Schisandrin A
• Schisantherin A
• Schisandrin
• Arisantetralone C
• 3,5,6,6-tetraMethyl-4,5,5a,6,7,8-hexahydrocyclopenta[c]pentalen-2(1H)-one
• schisantherin D