29307-60-6

29307-60-6 structure

Name: Genipin-1-O-gentiobioside
Chemical Name: methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
CAS Number: 29307-60-6
Molecular Formula: C₂₃H₃₄O₁₅
Molecular Weight: 550.507
Catalog: Research Areas Inflammation/Immunology
Create Date: 2018-09-20 21:54:44
Modify Date: 2024-01-08 14:04:00
Genipin 1-β-D-gentiobioside (Genipin 1-gentiobioside) is one of the most abundant and bioactive iridoid glycosides in Gardenia jasminoides Ellis, which possesses hepatoprotective, anti-inflammatory, antioxidant, and antithrombotic activities.

Name	methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Synonyms	genipingentiobioside Methyl (1S,4aS,7aS)-1-{[6-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy}-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate Genipin 1-gentiobioside Cyclopenta[c]pyran-4-carboxylic acid, 1-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)- GBGB Genipin 1-β-D-gentiobioside

Description	Genipin 1-β-D-gentiobioside (Genipin 1-gentiobioside) is one of the most abundant and bioactive iridoid glycosides in Gardenia jasminoides Ellis, which possesses hepatoprotective, anti-inflammatory, antioxidant, and antithrombotic activities.
Related Catalog	Signaling Pathways >> Others >> Others Research Areas >> Inflammation/Immunology Natural Products >> Terpenoids and Glycosides
In Vivo	Genipin 1-β-D-gentiobioside (Genipin gentiobioside) has moderate terminal elimination half-life (t1/2=1.65±0.87 h and 2.43±2.30 h for nomal rats (11.4 mg/kg) and cholestatic liver injury (CLI) rats (11.4 mg/kg), respectively)[1].
Animal Admin	Rats[1] Twelve male rats are divided randomly into normal and acute cholestatic liver injury (CLI) group, with 6 rats in each. The rats are kept in an air-conditioned environment at a temperature of 22-24°C and a relative humidity of 50±10%, with access to the standard laboratory food and water. After fasted for 12 h, the rats are given Zhi-Zi-Da-Huang decoction (ZZDHD) at a dose of 8 g/kg (crude drug/body weight, equivalent to 35.9 mg/kg geniposide, 11.4 mg/kg Genipin 1-β-D-gentiobioside, 2.50 mg/kg Rhein, 0.23 mg/kg Emodin, 11.2 mg/kg Isonaringin, 83.5 mg/kg Naringin, 12.4 mg/kg Hesperidin and 79.6 mg/kg Neohesperidin) by oral administration. Blood samples (approximately 0.3 mL) are collected from the fosse orbital vein using heparinized 1.5 mL polythene tubes before the dose and at 0.08, 0.17, 0.33, 0.67, 1, 1.5, 2, 3, 4, 6, 8, 10, 12, 24, 36 and 48 h after dosing, and then centrifuged immediately at 13,000 rpm for 5 min. Plasma is transferred into clean tubes and stored at -80°C until analysis[1].
References	[1]. Zhu H, et al. Simultaneous determination of two iridoid glycosides, two anthraquinones and four flavonoid glycosides of Zhi-Zi-Da-Huang decoction in rat plasma by UFLC-MS/MS: application to a comparative pharmacokinetic study in normal and cholestatic liver injury rats. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jun 1;960:116-25.

Density	1.6±0.1 g/cm3
Boiling Point	835.3±65.0 °C at 760 mmHg
Molecular Formula	C₂₃H₃₄O₁₅
Molecular Weight	550.507
Flash Point	281.0±27.8 °C
Exact Mass	550.189758
PSA	234.29000
LogP	-1.62
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.647
Storage condition	2-8C

114653-46-2

29307-60-6

Literature: Nishizawa; Izuhara; Kaneko; Koshihara; Fujimoto Chemical and Pharmaceutical Bulletin, 1988 , vol. 36, # 1 p. 87 - 95

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