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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H14O5
Molecular Weight 226.2259
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENIPIN

SMILES

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

InChI

InChIKey=AZKVWQKMDGGDSV-BCMRRPTOSA-N
InChI=1S/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7-,9-,11-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7299624 | https://www.ncbi.nlm.nih.gov/pubmed/24041312 | https://www.ncbi.nlm.nih.gov/pubmed/9827681

Genipin is an aglycone derived from an iridoid glycoside called Geniposide (structure on the bottom) present in fruit of Gardenia jasmindides Ellis. Genipin have been demonstrated to have diverse pharmacological activities including anti-inflammatory, antioxidative, neuroprotective, and neurotrophic effects. Genipin is an excellent natural cross-linker for protein, collagen, gelatin, and chitosan cross-linking and can be considered as a substitute for glutaraldehyde. Due to cross-linking properties genipin can be used in controlling drug delivery. In addition genipin exerts choleretic action.

CNS Activity

CNS Active
3913
Curator's Comment: Genipin is CNS active in animal studies. No human data available

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Mitochondrial uncoupling protein 2
1
Target ID: P70406
Gene ID: 22228.0
Gene Symbol: Ucp2
Target Organism: Mus musculus (Mouse)
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Harvested porcine mitral xenograft fixation: impact on fluid dynamic performance.
2001 Jan
[Studies on the cytological function of the biomembrane and the neurons].
2002 Oct
Isolation and characterization of water-soluble intermediates of blue pigments transformed from geniposide of Gardenia jasminoides.
2002 Oct 23
Crosslinking of biological tissues using genipin and/or carbodiimide.
2003 Mar 1
Biocompatibility and biodegradation of a bone composite containing tricalcium phosphate and genipin crosslinked gelatin.
2004 Jun 15
Genipin--a novel fingerprint reagent with colorimetric and fluorogenic activity.
2004 Mar
Acellular bovine pericardia with distinct porous structures fixed with genipin as an extracellular matrix.
2004 May-Jun
Metabolic activities of ginsenoside Rb1, baicalin, glycyrrhizin and geniposide to their bioactive compounds by human intestinal microflora.
2004 Oct
A natural compound (ginsenoside Re) isolated from Panax ginseng as a novel angiogenic agent for tissue regeneration.
2005 Apr
Genipin prevents fulminant hepatic failure resulting in reduction of lethality through the suppression of TNF-alpha production.
2005 Dec
Construction of varying porous structures in acellular bovine pericardia as a tissue-engineering extracellular matrix.
2005 May
Genipin, a novel fingerprint reagent with colorimetric and fluorogenic activity, part II: optimization, scope and limitations.
2005 Nov
Genipin suppresses subconjunctival fibroblast migration, proliferation and myofibroblast transdifferentiation.
2006
Anti-inflammatory evaluation of gardenia extract, geniposide and genipin.
2006 Feb 20
Genipin cross-linked alginate-chitosan microcapsules: membrane characterization and optimization of cross-linking reaction.
2006 Jul
Swelling and mechanical properties of biopolymer hydrogels containing chitosan and bovine serum albumin.
2006 Nov
Preparation and characterization of novel polymeric microcapsules for live cell encapsulation and therapy.
2007
Rheological study of genipin cross-linked chitosan hydrogels.
2007 Dec
Constituents of Gardenia volkensii: their brine shrimp lethality and DPPH radical scavenging properties.
2007 Feb
Application of crosslinkers to dentin collagen enhances the ultimate tensile strength.
2007 Jan
Synthesis of monoterpene alkaloid derivatives from the iridoid glucoside geniposide.
2007 Nov
Molecularly imprinted chitosan-genipin hydrogels with recognition capacity toward o-xylene.
2007 Nov
Noninvasive nuclear factor-kappaB bioluminescence imaging for the assessment of host-biomaterial interaction in transgenic mice.
2007 Oct
Effects of collagen crosslinking on tissue fragility.
2008 Jan
Effect of genipin on the biliary excretion of cholephilic compounds in rats.
2008 Jun
Evaluation of the release rate of bioactive recombinant human epidermal growth factor from crosslinking collagen sponges.
2008 Mar
Genipin exhibits neurotrophic effects through a common signaling pathway in nitric oxide synthase-expressing cells.
2008 Mar 10
Patents

Patents

05078750
2
05272172
2
05374653
2
05459160
2
06262083
1
JP1019092A
1
JP1022820A
1
JP1023861A
1
JP1031796A
1
JP2000053544A
1
JP2000095654A
6
JP2001503299A
1
JP2006500975A
14
JP2007526793A
16
JP2009502364A
1
JP2009525327A
1
JP2010075692A
1
JP2010155830A
1
JP2010521985A
1
JP2010522164A
1
JP2011102297A
1
JP2011115564A
1
JP4746046B2
1
JPH02107162A
1
JPH02107163A
1
JPH02263833A
1
JPH0358791A
1
JPH0366682A
1
JPH05339134A
1
JPH0558859A
1
JPH0656638A
1
JPH0687740A
2
JPH07310023A
1
JPH0995445A
1
JPS5253934A
1
JPS55164625A
1
JPS6147167A
1
JPS63123382A
1
JPS63157981A
1
JPS633064A
1
JPS6419092A
1
JPS6422820A
1
JPS6423861A
1
JPS6431796A
1

Sample Use Guides

In Vivo Use Guide
Oral genipin, at dose 50 mg/kg, exerts anti-inflammatory activity in carrageenan-induced rat paw edema
Route of Administration: Oral
In Vitro Use Guide
Genipin reduced the viability of K562 cells with an IC(50) value of approximately 250 μmol/L. Genipin 200-400 μmol/L induced formation of typical apoptotic bodies and DNA fragmentation.
Name Type Language
GENIPIN
Common Name English
(+)-GENIPIN
Common Name English
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A.ALPHA.,5,7A.ALPHA.-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER
Common Name English
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A,5,7A-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1R,4AS,7AS)-
Systematic Name English
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A,5,7A-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1R-(1.ALPHA.,4A.ALPHA.,7A.ALPHA.))-
Systematic Name English
Code System Code Type Description
WIKIPEDIA
Genipin
Created by admin on Sat Dec 16 07:59:10 GMT 2023 , Edited by admin on Sat Dec 16 07:59:10 GMT 2023
PRIMARY
FDA UNII
A3V2NE52YG
Created by admin on Sat Dec 16 07:59:10 GMT 2023 , Edited by admin on Sat Dec 16 07:59:10 GMT 2023
PRIMARY
PUBCHEM
442424
Created by admin on Sat Dec 16 07:59:10 GMT 2023 , Edited by admin on Sat Dec 16 07:59:10 GMT 2023
PRIMARY
CAS
6902-77-8
Created by admin on Sat Dec 16 07:59:10 GMT 2023 , Edited by admin on Sat Dec 16 07:59:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID30894999
Created by admin on Sat Dec 16 07:59:10 GMT 2023 , Edited by admin on Sat Dec 16 07:59:10 GMT 2023
PRIMARY
SUBSTANCE RECORD
Structure of GENIPIN
NIH
NCATS
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