calycosin
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477376646
| Name = Calycosin
| ImageFile = Calycosin.svg
| ImageSize = 220px
| ImageName = Chemical structure of calycosin
| ImageFile1 = Calycosin-3D-balls.png
| ImageSize1 = 220
| ImageAlt1 = Calycosin molecule
| IUPACName = 3′,7-Dihydroxy-4′-methoxyisoflavone
| SystematicName = 7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
| OtherNames = 7,3′-Dihydroxy-4′-methoxyisoflavone
3′-Hydroxyformononetin
|Section1={{Chembox Identifiers
| CASNo = 20575-57-9
| CASNo_Ref = {{cascite|changed|??}}
| CASNoOther =
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 241608
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 09N3E8P7TA
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17793
| PubChem = 5280448
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444104
| SMILES = O=C\1c3c(O/C=C/1c2ccc(OC)c(O)c2)cc(O)cc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZZAJQOPSWWVMBI-UHFFFAOYSA-N
| MeSHName =
}}
|Section2={{Chembox Properties
| C=16
| H=12
| O=5
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
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}}
Calycosin is an O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus{{Cite journal | doi = 10.1016/S0021-9673(02)00535-6| pmid = 12198969| title = Preparative isolation and purification of calycosin from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography| journal = Journal of Chromatography A| volume = 962| issue = 1–2| pages = 243–7| year = 2002| last1 = Ma| first1 = Xiaofeng| last2 = Zhang| first2 = Tianyou| last3 = Wei| first3 = Yun| last4 = Tu| first4 = Pengfei| last5 = Chen| first5 = Yingjie| last6 = Ito| first6 = Yoichiro}} and Trifolium pratense L. (red clover).{{cite journal | doi = 10.1016/S0031-9422(00)94679-X| title = Identification of isoflavones calycosin and pseudobaptigenin in Trifolium pratense| journal = Phytochemistry| volume = 17| issue = 9| pages = 1683| year = 1978| last1 = Biggs| first1 = David R| last2 = Lane| first2 = Geoffrey A| bibcode = 1978PChem..17.1683B}}
Biosynthesis
Isoflavone 3′-hydroxylase uses formononetin, NADPH, H+ and O2 to produce calycosin, NADP+ and H2O.
Pharmacology
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.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}}