IUPAC/Chemical Name
(1S,4aS,7aS)-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
InChi Key
ZJDOESGVOWAULF-OGJQONSISA-N
InChi Code
InChI=1S/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)/t7-,9-,10-,11-,12+,13-,15+,16+/m1/s1
SMILES Code
O=C(C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@]3([H])[C@]1([H])CC=C3CO)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Geniposidic acid is an effective anticancer and radioprotection agent.
In vitro activity:
GPA pretreatment substantially attenuated LPS-induced NLRP3 expression at both the mRNA and protein levels (Fig. 2A and B and Fig. S2). Furthermore, the release of pro-inflammatory cytokines, including IL-1β, IL-6, and TNF-α, was markedly blunted by GPA pretreatment prior to LPS stimulation (Fig. 2C).
Reference: Redox Biol. 2022 Jul 14;55:102404. https://pubmed.ncbi.nlm.nih.gov/35868156/
In vivo activity:
The over-expression of LRH-1 in RPH can up-regulate the mRNA and protein levels of CYP7a1. GPA can improve the biochemical and liver pathology of ANIT-induced cholestasis rats, which may be related to the decrease of CYP7a1 by activating SHP through LRH-1 in RPH.
Reference: Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2019 Jun 28;44(6):605-613. https://pubmed.ncbi.nlm.nih.gov/31304920/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
30.0 |
80.14 |
|
| DMSO |
48.7 |
130.01 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
374.34
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Song M, Chen Z, Qiu R, Zhi T, Xie W, Zhou Y, Luo N, Fuqian Chen, Liu F, Shen C, Lin S, Zhang F, Gao Y, Liu C. Inhibition of NLRP3-mediated crosstalk between hepatocytes and liver macrophages by geniposidic acid alleviates cholestatic liver inflammatory injury. Redox Biol. 2022 Jul 14;55:102404. doi: 10.1016/j.redox.2022.102404. Epub ahead of print. PMID: 35868156; PMCID: PMC9304672.
2. Song M, Chen Z, Qiu R, Zhi T, Xie W, Zhou Y, Luo N, Fuqian Chen, Liu F, Shen C, Lin S, Zhang F, Gao Y, Liu C. Inhibition of NLRP3-mediated crosstalk between hepatocytes and liver macrophages by geniposidic acid alleviates cholestatic liver inflammatory injury. Redox Biol. 2022 Jul 14;55:102404. doi: 10.1016/j.redox.2022.102404. Epub ahead of print. PMID: 35868156; PMCID: PMC9304672.
3. Chen H, Gao X, Zhao W, Yu H, Wang N, Mi S. [Effect of geniposidic acid on SHP-LRH-1 signaling pathway in cholestasis rats]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2019 Jun 28;44(6):605-613. Chinese. doi: 10.11817/j.issn.1672-7347.2019.06.001. PMID: 31304920.
In vitro protocol:
1. Song M, Chen Z, Qiu R, Zhi T, Xie W, Zhou Y, Luo N, Fuqian Chen, Liu F, Shen C, Lin S, Zhang F, Gao Y, Liu C. Inhibition of NLRP3-mediated crosstalk between hepatocytes and liver macrophages by geniposidic acid alleviates cholestatic liver inflammatory injury. Redox Biol. 2022 Jul 14;55:102404. doi: 10.1016/j.redox.2022.102404. Epub ahead of print. PMID: 35868156; PMCID: PMC9304672.
In vivo protocol:
1. Song M, Chen Z, Qiu R, Zhi T, Xie W, Zhou Y, Luo N, Fuqian Chen, Liu F, Shen C, Lin S, Zhang F, Gao Y, Liu C. Inhibition of NLRP3-mediated crosstalk between hepatocytes and liver macrophages by geniposidic acid alleviates cholestatic liver inflammatory injury. Redox Biol. 2022 Jul 14;55:102404. doi: 10.1016/j.redox.2022.102404. Epub ahead of print. PMID: 35868156; PMCID: PMC9304672.
2. Chen H, Gao X, Zhao W, Yu H, Wang N, Mi S. [Effect of geniposidic acid on SHP-LRH-1 signaling pathway in cholestasis rats]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2019 Jun 28;44(6):605-613. Chinese. doi: 10.11817/j.issn.1672-7347.2019.06.001. PMID: 31304920.
1. Carrillo-Ocampo, D., Bazaldúa-Gómez, S., Bonilla-Barbosa, J.R., et al. Anti-inflammatory activity of iridoids and verbascoside isolated from Castilleja tenuiflora. Molecules 18(10), 12109-12118 (2013).
2. Kim, S.-J., Kim, K.-M., Park, J., et al. Geniposidic acid protects against D-galactosamine and lipopolysaccharide-induced hepatic failure in mice. J. Ethnopharmacol. 146(1), 271-277 (2013).
3. Nakamura, K., Hosoo, S., Yamaguchi, S., et al. Geniposidic acid upregulates atrial natriuretic peptide secretion and lowers blood pressure in spontaneously hypertensive rat. J. Funct. Foods 40, 634-638 (2018).
