GARDENOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H24O11
Molecular Weight	404.3659
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12C=C[C@@](O)(CO)[C@@]1([H])[C@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C2C(=O)OC

InChI

InChIKey=XJMPAUZQVRGFRE-AYDWLWLASA-N

InChI=1S/C17H24O11/c1-25-14(23)8-5-26-15(10-7(8)2-3-17(10,24)6-19)28-16-13(22)12(21)11(20)9(4-18)27-16/h2-3,5,7,9-13,15-16,18-22,24H,4,6H2,1H3/t7-,9-,10-,11-,12+,13-,15+,16+,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C17H24O11
Molecular Weight	404.3659
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27435384
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26610473

Iridoid glycoside gardenoside is the main effective extraction of Gardenia jasminoides Ellis, which is an indigenous medicinal herb widely used for hepatoprotective, analgesic, and antipyretic drug. Gardenoside was shown to be effective toward HCl/ethanol induced gastric injury in mice and prevents cellular steatosis.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nonalcoholic steatohepatitis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26610473	Primary		Basic research	Unknown Approved Use Unknown
Gastritis 45 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27435384	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Novel pharmacokinetic studies of the Chinese formula Huang-Lian-Jie-Du-Tang in MCAO rats.	2013 Jul 15	23628154
An LC-MS method for simultaneous determination of five iridoids from Zhi-zi-chi Decoction in rat brain microdialysates and tissue homogenates: towards an in depth study for its antidepressive activity.	2014 Aug 15	25049209
Inhibitory Effect of Gardenoside on Free Fatty Acid-Induced Steatosis in HepG2 Hepatocytes.	2015 Nov 20	26610473
Preventive effect of Gardenia jasminoides on HCl/ethanol induced gastric injury in mice.	2017 Jan	27435384

Patents

Sample Use Guides

In Vivo Use Guide

mice treated with gardenoside (200 mg/kg) once a day for 2 weeks

Route of Administration: Oral

In Vitro Use Guide

Quantities of 30, 40 and 50 µM of Gardenoside were significantly toxic to HepG2 cells. 10 and 20 µM gardenoside has a protective effect on FFA-induced cellular steatosis in HepG2 cells which indicates that Gardenoside might be a potential therapeutic herb against NASH by suppressed supernatant inflammatory cytokine production and intracellular NFkB activity.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:09:12 GMT 2023` Edited by `admin` on `Sat Dec 16 11:09:12 GMT 2023`
Record UNII	INE79XNR2C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GARDENOSIDE

Common Name

English

CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,7,7A-TETRAHYDRO-7-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1S,4AS,7S,7AS)-

Systematic Name

English

NSC-325664

Code

English

Code System Code Type Description

NSC

325664