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Genipin-1-O-gentiobioside

Names

[ CAS No. ]:
29307-60-6

[ Name ]:
Genipin-1-O-gentiobioside

[Synonym ]:
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

Biological Activity

[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.


[Related Small Molecules]

Captisol | Cyclosporin A | H2DCFDA | 0MPTP hydrochloride | GW4869 | Etomoxir | TD139 | Mitoquinone mesylate | GSK2795039 | JC-1 | BAPTA-AM | AP 20187 | Setanaxib (GKT137831) | D-Luciferin | Crotaline

Chemical & Physical Properties

[ 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

Synthetic Route


Related Compounds