Calycosin
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| Names | |
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| IUPAC name
3′,7-Dihydroxy-4′-methoxyisoflavone
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| Systematic IUPAC name
7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one | |
| Other names
7,3′-Dihydroxy-4′-methoxyisoflavone
3′-Hydroxyformononetin | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.222.904 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C16H12O5 | |
| Molar mass | 284.267 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Calycosin is an O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus[1] and Trifolium pratense L. (red clover).[2]
Biosynthesis
[edit]Isoflavone 3′-hydroxylase uses formononetin, NADPH, H+ and O2 to produce calycosin, NADP+ and H2O.
Pharmacology
[edit]Calycosin has been shown to possess anti-cancer properties in vitro, and extracts of Astragalus membranaceus have been used to complement chemotherapy regimes in treatment of cancer in China.[3][4][5]
References
[edit]- ^ Ma, Xiaofeng; Zhang, Tianyou; Wei, Yun; Tu, Pengfei; Chen, Yingjie; Ito, Yoichiro (2002). "Preparative isolation and purification of calycosin from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography". Journal of Chromatography A. 962 (1–2): 243–7. doi:10.1016/S0021-9673(02)00535-6. PMID 12198969.
- ^ Biggs, David R; Lane, Geoffrey A (1978). "Identification of isoflavones calycosin and pseudobaptigenin in Trifolium pratense". Phytochemistry. 17 (9): 1683. Bibcode:1978PChem..17.1683B. doi:10.1016/S0031-9422(00)94679-X.
- ^ Sohel M, Zahra Shova FT, Shuvo S, Mahjabin T, Mojnu Mia M, Halder D, Islam H, Roman Mogal M, Biswas P, Saha HR, Sarkar BC, Mamun AA. Unveiling the potential anti-cancer activity of calycosin against multivarious cancers with molecular insights: A promising frontier in cancer research. Cancer Med. 2024 Feb;13(3):e6924. doi:10.1002/cam4.6924 PMID 38230908
- ^ Ren F, Ma Y, Zhang K, Luo Y, Pan R, Zhang J, Kan C, Hou N, Han F, Sun X. Exploring the multi-targeting phytoestrogen potential of Calycosin for cancer treatment: A review. Medicine (Baltimore). 2024 May 3;103(18):e38023. doi:10.1097/MD.0000000000038023 PMID 38701310
- ^ Lu Q, Jiang J, Wang X, Wang R, Han X. Advancements in the Research of Astragalus membranaceus for the Treatment of Colorectal Cancer. Am J Chin Med. 2025;53(1):119-146. doi:10.1142/S0192415X25500065 PMID 39880662
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