Gardenoside
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MedKoo CAT#: 465304

CAS#: 24512-62-7

Description: Gardenoside is an iridoid glycoside that has been found in G. jasminoides and has anti-inflammatory and antinociceptive activities. It decreases free fatty acid-induced accumulation of lipid droplets and increases in TNF-α, IL-6, and IL-1β levels in HepG2 cells when used at concentrations of 10 and 20 µM. Gardenoside reduces increases in the expression of purinergic P2X3 and P2X7 receptors, as well as reverses decreases in mechanical withdrawal thresholds in a rat model of chronic constriction injury-induced neuropathic pain.


Chemical Structure

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Gardenoside
CAS# 24512-62-7

Theoretical Analysis

MedKoo Cat#: 465304
Name: Gardenoside
CAS#: 24512-62-7
Chemical Formula: C17H24O11
Exact Mass: 404.1319
Molecular Weight: 404.368
Elemental Analysis: C, 50.50; H, 5.98; O, 43.52

Price and Availability

Size Price Availability Quantity
1.0mg USD 260.0 2 Weeks
5.0mg USD 610.0 2 Weeks
10.0mg USD 900.0 2 Weeks
Bulk inquiry

Synonym: Gardenoside; NSC 325664; NSC325664; NSC-325664;

IUPAC/Chemical Name: methyl (1S,4aS,7S,7aS)-7-hydroxy-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

InChi Key: XJMPAUZQVRGFRE-AYDWLWLASA-N

InChi Code: 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

SMILES Code: COC(C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@]3([C@@]1(C=C[C@]3(CO)O)[H])[H])=O

Appearance: Solid powder

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
PBS (pH 7.2) 10.0 24.73
Ethanol 10.0 24.73
DMSO 10.0 24.73
DMF 30.0 74.19

Preparing Stock Solutions

The following data is based on the product molecular weight 404.368 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.

Recalculate based on batch purity %
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

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1: Dong R, Tian Q, Shi Y, Chen S, Zhang Y, Deng Z, Wang X, Yao Q, Han L. An Integrated Strategy for Rapid Discovery and Identification of Quality Markers in Gardenia Fructus Using an Omics Discrimination-Grey Correlation-Biological Verification Method. Front Pharmacol. 2021 Jun 24;12:705498. doi: 10.3389/fphar.2021.705498. PMID: 34248647; PMCID: PMC8264552.

2: Xia MY, Wang Y, Zheng YH, Song YN, Liu TL, Zhang C. [Quality changes of Gardeniae Fructus Praeparatus processed by different frying methods: a color- component correlation analysis]. Zhongguo Zhong Yao Za Zhi. 2021 May;46(9):2197-2206. Chinese. doi: 10.19540/j.cnki.cjcmm.20210220.303. PMID: 34047121.

3: Bao H, Yang H, Li J, Yang X, Huang X. Establishment and Development of Quality Evaluation Method for Sangbaipi Decoction ,,,and. J AOAC Int. 2021 Apr 28:qsab065. doi: 10.1093/jaoacint/qsab065. Epub ahead of print. PMID: 33909887.

4: Nguyen LTH, Ahn SH, Nguyen UT, Yang IJ, Shin HM. Geniposide, a Principal Component of Gardeniae Fructus, Protects Skin from Diesel Exhaust Particulate Matter-Induced Oxidative Damage. Evid Based Complement Alternat Med. 2021 Feb 2;2021:8847358. doi: 10.1155/2021/8847358. PMID: 33603823; PMCID: PMC7872751.

5: Liu F, Li Y, Li M, Wang J, Zhang Y, Du Y, Yang Y. Study on Mechanism of Iridoid Glycosides Derivatives from Fructus Gardeniae in Jiangxi Province by Network Pharmacology. Evid Based Complement Alternat Med. 2020 Jun 26;2020:4062813. doi: 10.1155/2020/4062813. PMID: 32714404; PMCID: PMC7336235.

6: Neri-Numa IA, Pessôa MG, Arruda HS, Pereira GA, Paulino BN, Angolini CFF, Ruiz ALTG, Pastore GM. Genipap (Genipa americana L.) fruit extract as a source of antioxidant and antiproliferative iridoids. Food Res Int. 2020 Aug;134:109252. doi: 10.1016/j.foodres.2020.109252. Epub 2020 Apr 18. PMID: 32517903.

7: Tenuta MC, Deguin B, Loizzo MR, Dugay A, Acquaviva R, Malfa GA, Bonesi M, Bouzidi C, Tundis R. Contribution of Flavonoids and Iridoids to the Hypoglycaemic, Antioxidant, and Nitric Oxide (NO) Inhibitory Activities of Arbutus unedo L. Antioxidants (Basel). 2020 Feb 22;9(2):184. doi: 10.3390/antiox9020184. PMID: 32098404; PMCID: PMC7071084.

8: Neri-Numa IA, DellaTorre A, Oriani VB, Franch GC Jr, Angolini CFF, Dupas Hubinger M, Ruiz ALTG, Pastore GM. In vitro bioactivity approach of unripe genipap (Genipa americana L., Rubiaceae) fruit extract and its solid lipid microparticle. Food Res Int. 2020 Jan;127:108720. doi: 10.1016/j.foodres.2019.108720. Epub 2019 Oct 9. PMID: 31882083.

9: Li C, Lan M, Lv J, Zhang Y, Gao X, Gao X, Dong L, Luo G, Zhang H, Sun J. Screening of the Hepatotoxic Components in Fructus Gardeniae and Their Effects on Rat Liver BRL-3A Cells. Molecules. 2019 Oct 30;24(21):3920. doi: 10.3390/molecules24213920. PMID: 31671698; PMCID: PMC6864725.

10: Park SH, An JE, Jang S, Kim JY, Lee JW, Kim HK. Gardenia jasminoides extract without crocin improved atopic dermatitis-like skin lesions via suppression of Th2-related cytokines in Dfe-induced NC/Nga mice. J Ethnopharmacol. 2019 Sep 15;241:112015. doi: 10.1016/j.jep.2019.112015. Epub 2019 Jun 4. PMID: 31173875.

11: Shan MQ, Wang TJ, Jiang YL, Yu S, Yan H, Zhang L, Wu QN, Geng T, Huang WZ, Wang ZZ, Xiao W. Comparative analysis of sixteen active compounds and antioxidant and anti-influenza properties of Gardenia jasminoides fruits at different times and application to the determination of the appropriate harvest period with hierarchical cluster analysis. J Ethnopharmacol. 2019 Apr 6;233:169-178. doi: 10.1016/j.jep.2019.01.004. Epub 2019 Jan 9. PMID: 30639058.

12: Tian G, Yang XF, Li C, Wu F, Liu X, Feng L, Jia XB. [Simultaneous determination of 9 components in Xiao'er Chiqiao Qingre granules by UPLC]. Zhongguo Zhong Yao Za Zhi. 2018 May;43(10):2081-2085. Chinese. doi: 10.19540/j.cnki.cjcmm.20180208.005. PMID: 29933674.

13: Yu M, Su B, Zhang X. Gardenoside suppresses the pain in rats model of chronic constriction injury by regulating the P2X3 and P2X7 receptors. J Recept Signal Transduct Res. 2018 Jun;38(3):198-203. doi: 10.1080/10799893.2018.1468782. Epub 2018 Jun 22. PMID: 29932348.

14: Neri-Numa IA, Angolini CFF, Bicas JL, Ruiz ALTG, Pastore GM. Iridoid blue- based pigments of Genipa americana L. (Rubiaceae) extract: Influence of pH and temperature on color stability and antioxidant capacity during in vitro simulated digestion. Food Chem. 2018 Oct 15;263:300-306. doi: 10.1016/j.foodchem.2018.05.001. Epub 2018 May 3. PMID: 29784321.

15: Chen L, Wang R, Cui L, Wang X, Wang L, Song F, Ji W. Preparation of five high-purity iridoid glycosides from Gardenia jasminoides Eills by molecularly imprinted solid-phase extraction integrated with preparative liquid chromatography. J Sep Sci. 2018 Jul;41(13):2759-2766. doi: 10.1002/jssc.201800086. Epub 2018 May 14. PMID: 29676851.

16: Yu M, Zhao Y, Zhang X. Gardenoside combined with ozone inhibits the expression of P2X3 and P2X7 purine receptors in rats with sciatic nerve injury. Mol Med Rep. 2018 Jun;17(6):7980-7986. doi: 10.3892/mmr.2018.8803. Epub 2018 Mar 28. PMID: 29620177.

17: Peixoto H, Roxo M, Koolen H, da Silva F, Silva E, Braun MS, Wang X, Wink M. Calycophyllum spruceanum (Benth.), the Amazonian "Tree of Youth" Prolongs Longevity and Enhances Stress Resistance in Caenorhabditis elegans. Molecules. 2018 Feb 27;23(3):534. doi: 10.3390/molecules23030534. PMID: 29495517; PMCID: PMC6017494.

18: Xiao RC, Luo GM, Dong LH, Zhu YY, Zhu JX, Zhang FB, Wu SN. [Comparison of chemical constituents in different parts of Gardenia jasminoides based on multiple wavelength HPLC-DAD]. Zhongguo Zhong Yao Za Zhi. 2017 Dec;42(23):4636-4640. Chinese. doi: 10.19540/j.cnki.cjcmm.2017.0203. PMID: 29376264.

19: Ma WW, Tao Y, Wang YY, Peng IF. Effects of Gardenia jasminoides extracts on cognition and innate immune response in an adult Drosophila model of Alzheimer's disease. Chin J Nat Med. 2017 Dec;15(12):899-904. doi: 10.1016/S1875-5364(18)30005-0. PMID: 29329646.

20: Kong M, Liu HH, Wu J, Shen MQ, Wang ZG, Duan SM, Zhang YB, Zhu H, Li SL. Effects of sulfur-fumigation on the pharmacokinetics, metabolites and analgesic activity of Radix Paeoniae Alba. J Ethnopharmacol. 2018 Feb 15;212:95-105. doi: 10.1016/j.jep.2017.10.023. Epub 2017 Nov 5. PMID: 29080828.