Gomisin A

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Names

[ Name ]:
Gomisin A

[Synonym ]:
(6S,7S)-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-6-ol
Gomisin A
Benzo[3',4']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxol-6-ol, 5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-, (6S,7S)-
Wuweizichun B
wuweizialcoholb
wuweizichunb
SchizandrolB
Besigomsin
BESIGOMISIN
Schisandrol B
TJN-101

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
579.7±50.0 °C at 760 mmHg

[ Melting Point ]:
88.5°C

[ Molecular Formula ]:
C₂₃H₂₈O₇

[ Molecular Weight ]:
416.464

[ Flash Point ]:
304.4±30.1 °C

[ Exact Mass ]:
416.183502

[ PSA ]:
75.61000

[ LogP ]:
4.77

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.561

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DE8396900

CHEMICAL NAME :: Benzo(3,4)cycloocta(1,2-f)(1,3)benzodioxol-6-ol, 5,6,7,8-tetrahydro-6,7-dimethyl- 1,2,3,13-tetramethoxy-, stereoisomer

CAS REGISTRY NUMBER :: 58546-54-6

LAST UPDATED :: 198910

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C23-H28-O7

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 777 mg/kg

TOXIC EFFECTS :: Behavioral - sleep Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 101,1030,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 390 mg/kg

TOXIC EFFECTS :: Behavioral - sleep Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 101,1030,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Behavioral - sleep Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 101,1030,1981

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

Precursor & DownStream

Precursor

met B
Dibromomethane
((2'R,7S)-1,2,3,13-tetramethoxy-7,8-dihydro-5H-spiro[benzo[3',4']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxole-6,2'-oxiran]-7-yl)methyl methanesulfonate
3,4,5-Trimethoxybenzaldehyde
(S)-(E)-3-[5-Methoxy-3,4-(methylenedioxy)benzyl]butanolide
4-(3,4-dihydroxy-5-methoxybenzyl)-3-(3,4,5-trimethoxybenzylidene)dihydrofuran-2(3H)-one

DownStream

Articles

Gomisin A inhibits lipopolysaccharide-induced inflammatory responses in N9 microglia via blocking the NF-κB/MAPKs pathway.

Food Chem. Toxicol. 63 , 119-27, (2014)

Gomisin A, one of the major dibenzocyclooctadiene lignans isolated from Schisandra chinensis Baill., has proved to possess a variety of pharmacological effects. The aim of the present study was to inv...

Gomisin A enhances tumor necrosis factor-α-induced G1 cell cycle arrest via signal transducer and activator of transcription 1-mediated phosphorylation of retinoblastoma protein.

Biol. Pharm. Bull. 35(11) , 1997-2003, (2012)

Gomisin A, a dibenzocyclooctadiene lignan isolated from the fruit of Schisandra chinensis, has been reported as an anti-cancer substance. In this study, we investigated the effects of gomisin A on can...

Antihypertensive effect of gomisin A from Schisandra chinensis on angiotensin II-induced hypertension via preservation of nitric oxide bioavailability.

Hypertens. Res. 35(9) , 928-34, (2012)

Gomisin A (GA) is a small molecular weight lignan present in Schisandra chinensis, and has been demonstrated to have vasodilatory activity. In the present study, we investigated the effect of GA on bl...