Icariside I
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MedKoo CAT#: 463979

CAS#: 56725-99-6

Description: Icariside I is a flavonoid glycoside and an active metabolite of icariin that has been found in Epimedium and has osteogenic and anticancer activities. It is formed from icariin in rats by intestinal microbiota. It stimulates the proliferation and differentiation of isolated rat osteoblasts in a concentration-dependent manner. Icariside I increases the cytotoxicity of adriamycin in multidrug-resistant MCF-7/adr breast cancer cells with an IC50 value of 60.78 µM.

Chemical Structure

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Icariside I
CAS# 56725-99-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 463979
Name: Icariside I
CAS#: 56725-99-6
Chemical Formula: C27H30O11
Exact Mass: 530.18
Molecular Weight: 530.526
Elemental Analysis: C, 61.13; H, 5.70; O, 33.17

Price and Availability

Size Price Availability Quantity
10mg USD 250 2 Weeks
25mg USD 450 2 Weeks
50mg USD 750 2 Weeks
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Synonym: Icariside I; Icariside-I;

IUPAC/Chemical Name: 3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

InChi Key: IYCPMVXIUPYNHI-WPKKLUCLSA-N

InChi Code: InChI=1S/C27H30O11/c1-12(2)4-9-15-17(36-27-24(34)22(32)20(30)18(11-28)37-27)10-16(29)19-21(31)23(33)25(38-26(15)19)13-5-7-14(35-3)8-6-13/h4-8,10,18,20,22,24,27-30,32-34H,9,11H2,1-3H3/t18-,20-,22+,24-,27-/m1/s1

SMILES Code: C/C(C)=C\CC1=C2C(C(C(O)=C(O2)C3=CC=C(OC)C=C3)=O)=C(O)C=C1O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O

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: 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

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Icariside I is a metabolite of Icarlin, which could regulate bone remodeling and is recognized as an effective agent for the treatment of osteoporosis.
In vitro activity: These results suggest that Icariside I specifically enhances NLRP3 inflammasome activation triggered by ATP and nigericin, but not SiO2, poly(I:C) and cytosolic LPS. Reference: Cell Commun Signal. 2021 Feb 11;19(1):13. https://pubmed.ncbi.nlm.nih.gov/33573688/
In vivo activity: In vivo, oral administration of icariside I downregulates SLC7A8 and PAT4 transporters and AhR, thus inhibiting nuclear PD-1 in CTLs. Moreover, icariside I significantly upregulates CD8 + T cells in both peripheral blood and tumor tissues of tumor-bearing mice. Reference: Biomed Pharmacother. 2022 Sep;153:113387. https://pubmed.ncbi.nlm.nih.gov/35834991/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 1.0 1.88
DMSO 31.8 59.85
DMSO:PBS (pH 7.2) (1:3) 0.3 0.47

Preparing Stock Solutions

The following data is based on the product molecular weight 530.53 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
Formulation protocol: 1. Gao Y, Xu G, Ma L, Shi W, Wang Z, Zhan X, Qin N, He T, Guo Y, Niu M, Wang J, Bai Z, Xiao X. Icariside I specifically facilitates ATP or nigericin-induced NLRP3 inflammasome activation and causes idiosyncratic hepatotoxicity. Cell Commun Signal. 2021 Feb 11;19(1):13. doi: 10.1186/s12964-020-00647-1. PMID: 33573688; PMCID: PMC7879676. 2. Liu M, Xu H, Ma Y, Cheng J, Hua Z, Huang G. Osteoblasts Proliferation and Differentiation Stimulating Activities of the Main Components of Epimedii folium. Pharmacogn Mag. 2017 Jan-Mar;13(49):90-94. doi: 10.4103/0973-1296.197654. PMID: 28216889; PMCID: PMC5307921. 3. Chen G, Huang J, Lei H, Wu F, Chen C, Song Y, Cao Z, Zhang C, Zhang C, Ma Y, Huang M, Zhou J, Lu Y, Zhao Y, Zhang L. Icariside I - A novel inhibitor of the kynurenine-AhR pathway with potential for cancer therapy by blocking tumor immune escape. Biomed Pharmacother. 2022 Sep;153:113387. doi: 10.1016/j.biopha.2022.113387. Epub 2022 Jul 11. PMID: 35834991. 4. Chen G, Cao Z, Shi Z, Lei H, Chen C, Yuan P, Wu F, Liu C, Dong M, Song Y, Zhou J, Lu Y, Zhang L. Microbiome analysis combined with targeted metabolomics reveal immunological anti-tumor activity of icariside I in a melanoma mouse model. Biomed Pharmacother. 2021 Aug;140:111542. doi: 10.1016/j.biopha.2021.111542. Epub 2021 Jun 2. PMID: 34088571.
In vitro protocol: 1. Gao Y, Xu G, Ma L, Shi W, Wang Z, Zhan X, Qin N, He T, Guo Y, Niu M, Wang J, Bai Z, Xiao X. Icariside I specifically facilitates ATP or nigericin-induced NLRP3 inflammasome activation and causes idiosyncratic hepatotoxicity. Cell Commun Signal. 2021 Feb 11;19(1):13. doi: 10.1186/s12964-020-00647-1. PMID: 33573688; PMCID: PMC7879676. 2. Liu M, Xu H, Ma Y, Cheng J, Hua Z, Huang G. Osteoblasts Proliferation and Differentiation Stimulating Activities of the Main Components of Epimedii folium. Pharmacogn Mag. 2017 Jan-Mar;13(49):90-94. doi: 10.4103/0973-1296.197654. PMID: 28216889; PMCID: PMC5307921.
In vivo protocol: 1. Chen G, Huang J, Lei H, Wu F, Chen C, Song Y, Cao Z, Zhang C, Zhang C, Ma Y, Huang M, Zhou J, Lu Y, Zhao Y, Zhang L. Icariside I - A novel inhibitor of the kynurenine-AhR pathway with potential for cancer therapy by blocking tumor immune escape. Biomed Pharmacother. 2022 Sep;153:113387. doi: 10.1016/j.biopha.2022.113387. Epub 2022 Jul 11. PMID: 35834991. 2. Chen G, Cao Z, Shi Z, Lei H, Chen C, Yuan P, Wu F, Liu C, Dong M, Song Y, Zhou J, Lu Y, Zhang L. Microbiome analysis combined with targeted metabolomics reveal immunological anti-tumor activity of icariside I in a melanoma mouse model. Biomed Pharmacother. 2021 Aug;140:111542. doi: 10.1016/j.biopha.2021.111542. Epub 2021 Jun 2. PMID: 34088571.

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1: Wang M, Gao H, Li W, Wu B. Icariin and its metabolites regulate lipid metabolism: From effects to molecular mechanisms. Biomed Pharmacother. 2020 Nov;131:110675. doi: 10.1016/j.biopha.2020.110675. Epub 2020 Aug 28. PMID: 32861069.

2: Tang XY, Dai ZQ, Wu QC, Zeng JX, Gao MX, Xiao HH, Yao ZH, Dai Y, Yao XS. Simultaneous determination of multiple components in rat plasma and pharmacokinetic studies at a pharmacodynamic dose of Xian-Ling-Gu-Bao capsule by UPLC-MS/MS. J Pharm Biomed Anal. 2020 Jan 5;177:112836. doi: 10.1016/j.jpba.2019.112836. Epub 2019 Aug 26. PMID: 31473481.

3: Teo YL, Cheong WF, Cazenave-Gassiot A, Ji S, Logan S, Lee ZXK, Li J, Seng KY, Lee LS, Yong EL. Pharmacokinetics of Prenylflavonoids following Oral Ingestion of Standardized Epimedium Extract in Humans. Planta Med. 2019 Mar;85(4):347-355. doi: 10.1055/a-0806-7673. Epub 2018 Dec 6. PMID: 30522143.

4: Liu M, Xu H, Ma Y, Cheng J, Hua Z, Huang G. Osteoblasts Proliferation and Differentiation Stimulating Activities of the Main Components of Epimedii folium. Pharmacogn Mag. 2017 Jan-Mar;13(49):90-94. doi: 10.4103/0973-1296.197654. PMID: 28216889; PMCID: PMC5307921.

5: Cheng T, Sheng T, Yi Y, Zhang T, Han H. Metabolism profiles of icariin in rats using ultra-high performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry and in vitro enzymatic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Oct 15;1033-1034:353-360. doi: 10.1016/j.jchromb.2016.09.010. PMID: 27620672.

6: Wu H, Kim M, Han J. Icariin Metabolism by Human Intestinal Microflora. Molecules. 2016 Aug 31;21(9):1158. doi: 10.3390/molecules21091158. PMID: 27589718; PMCID: PMC6273050.

7: Sun E, Xu F, Qian Q, Cui L, Tan X, Jia X. Metabolite Profiles of Icariin in Rat Feces, Bile and Urine by Ultraperformance Liquid-Chromatography/Quadrupole- Time-of-Flight Mass Spectrometry. J Chromatogr Sci. 2016 Feb;54(2):158-64. doi: 10.1093/chromsci/bmv121. PMID: 26792083.

8: Ming LG, Chen KM, Xian CJ. Functions and action mechanisms of flavonoids genistein and icariin in regulating bone remodeling. J Cell Physiol. 2013 Mar;228(3):513-21. doi: 10.1002/jcp.24158. PMID: 22777826.

9: Qian Q, Li SL, Sun E, Zhang KR, Tan XB, Wei YJ, Fan HW, Cui L, Jia XB. Metabolite profiles of icariin in rat plasma by ultra-fast liquid chromatography coupled to triple-quadrupole/time-of-flight mass spectrometry. J Pharm Biomed Anal. 2012 Jul;66:392-8. doi: 10.1016/j.jpba.2012.03.053. Epub 2012 Apr 5. PMID: 22522037.

10: Wong SP, Shen P, Lee L, Li J, Yong EL. Pharmacokinetics of prenylflavonoids and correlations with the dynamics of estrogen action in sera following ingestion of a standardized Epimedium extract. J Pharm Biomed Anal. 2009 Sep 8;50(2):216-23. doi: 10.1016/j.jpba.2009.04.022. Epub 2009 May 3. PMID: 19464838.

11: Shen P, Wong SP, Li J, Yong EL. Simple and sensitive liquid chromatography- tandem mass spectrometry assay for simultaneous measurement of five Epimedium prenylflavonoids in rat sera. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Jan 1;877(1-2):71-8. doi: 10.1016/j.jchromb.2008.11.030. Epub 2008 Nov 27. PMID: 19083275.

12: Qin L, Han T, Zhang Q, Cao D, Nian H, Rahman K, Zheng H. Antiosteoporotic chemical constituents from Er-Xian Decoction, a traditional Chinese herbal formula. J Ethnopharmacol. 2008 Jul 23;118(2):271-9. doi: 10.1016/j.jep.2008.04.009. Epub 2008 Apr 15. PMID: 18501540.

13: Park JS, Park HY, Rho HS, Ahn S, Kim DH, Chang IS. Statistically designed enzymatic hydrolysis for optimized production of icariside II as a novel melanogenesis inhibitor. J Microbiol Biotechnol. 2008 Jan;18(1):110-7. PMID: 18239426.

14: Huang H, Liang M, Zhang X, Zhang C, Shen Z, Zhang W. Simultaneous determination of nine flavonoids and qualitative evaluation of Herba Epimedii by high performance liquid chromatography with ultraviolet detection. J Sep Sci. 2007 Dec;30(18):3207-13. doi: 10.1002/jssc.200700262. PMID: 18008281.

15: Xu W, Zhang Y, Yang M, Shen Z, Zhang X, Zhang W, Li H. LC-MS/MS method for the simultaneous determination of icariin and its major metabolites in rat plasma. J Pharm Biomed Anal. 2007 Nov 30;45(4):667-72. doi: 10.1016/j.jpba.2007.07.007. Epub 2007 Jul 10. PMID: 17706393.

16: Liang HR, Yan WM, Li L, Jiang L, Dai L. [Studies on the chemical constituents of Epimedium acuminatum Franch]. Zhongguo Zhong Yao Za Zhi. 1993 Nov;18(11):677-9, 703. Chinese. PMID: 8003229.