methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

• ChemBase ID: 73272
• Molecular Formular: C17H24O10
• Molecular Mass: 388.36646
• Monoisotopic Mass: 388.13694697
• SMILES: [C@H]1([C@H](O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1OC=C([C@@H]2[C@H]1C(=CC2)CO)C(=O)OC)CO)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2C(=CC3)CO)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8-,10-,11-,12-,13+,14-,16+,17+/m1/s1
• InChIKey: IBFYXTRXDNAPMM-BVTMAQQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate
• IUPAC Traditional name: geniposide; methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate
• Synonyms: Geniposide; Genipin 1-glucoside; Jasminoidin; Geniposide

Database IDs

• CAS Number: 24512-63-8
• PubChem SID: 162038192
• PubChem CID: 107848

CALCULATED PROPERTIES

• Acid pKa: 12.206515
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.2147315
• LogD (pH = 7.4): -2.2147381
• Log P: -2.2147312
• Molar Refractivity: 88.5066 cm^3
• Polarizability: 35.61959 Å^3
• Polar Surface Area: 155.14 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Mechanism of Action: Glucagon-like peptide-1 (GLP-1) receptor agonist

Product Information

• Salt Data: Free Base
• Biological Source: Constit. of Gardenia jasminoides
• Application(s): Anti-angiogenic; Anti-inflammatory; Antithrombotic; Antitumor; Neuroprotective

DETAILS

Selleck Chemicals - S2411

Research Area: Cardiovascular Disease
Biological Activity:
Geniposide is an iridoid glycoside isolated from the fruit of Gardenia jasminoides Ellis. Geniposide is one of the biologically active ingredients of gardenia fruit. Geniposide is widely used in multi-component injection in the treatment of cerebrovascular and cardiovascular diseases in China for its anti-thrombotic and anti-inflammatory effects. Geniposide exerts protective effects against hepatic steatosis in rats fed with a high fat diet; the underlying mechanism may be associated with its antioxidant actions or regulation of adipocytokine release and expression of peroxisome proliferator-activated receptor-α. Geniposide (10-20 μM) inhibited high glucose (33 mM)-induced adhesion of monocytes to HUVECs in a dose-dependent manner. Geniposide (5-40 μM) also inhibited high glucose-induced expression of VCAM-1 and E-selectin at the gene and protein levels. Furthermore, geniposide (5-20 mM) decreased reactive oxygen species production and prevented IkappaB degradation in the cytoplasm and NF-kappaB translocation from the cytoplasm to the nucleus in HUVECs. [1][2][3]References on Geniposide[1] J Zhejiang Univ Sci B., 2011 Feb, 12(2):143-8[2] J Pharm Pharmacol., 2011 Apr, 63(4):587-93[3] Acta Pharmacol Sin., 2010 Aug, 31(8):953-62

REFERENCES

• Ma T et al. J Pharm Pharmacol. 2011 Apr; 63(4):587-93.
• 1. Hsua HY, Yangb JJ, Lina SY, Lin CC. Comparisons of geniposidic acid and previous termgeniposidenext term on antitumor and radioprotection after sublethal irradiation,
• Cancer Lett. 113 (1997), pp. 31?7.
• 2. Koo HJ, Lee S, Shin KH, Kim BC, Lim CJ, Park EH. Geniposide, an anti-angiogenic compound from the fruits of Gardenia jasminoides. Planta Med. 2004 May;70(5):467-9.
• 3. Koo HJ, Lim KH, Jung HJ, Park EH. Anti-inflammatory evaluation of gardenia extract, geniposide and genipin. J Ethnopharmacol. 2006 Feb 20;103(3):496-500. Epub 2005 Sep 19.
• 4. Suzuki Y, Kondo K, Ikeda Y, Umemura K. Antithrombotic effect of geniposide and genipin in the mouse thrombosis model. Planta Med. 2001 Dec;67(9):807-10.
• 5. Lee P, Lee J, Choi SY, Lee SE, Lee S, Son D. Geniposide from Gardenia jasminoides attenuates neuronal cell death in oxygen and glucose deprivation-exposed rat hippocampal slice culture.
• Biol Pharm Bull. 2006 Jan;29(1):174-6.
• 6. Liu J, Yin F, Zheng X, Jing J, Hu Y. Geniposide, a novel agonist for GLP-1 receptor, prevents PC12 cells from oxidative damage via MAP kinase pathway.
• Neurochem Int. 2007 Nov-Dec;51(6-7):361-9. Epub 2007 May 6.