Calycosin

Calycosin

Chemical structure of calycosin
Names
IUPAC name 3′,7-Dihydroxy-4′-methoxyisoflavone
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
CAS Number	20575-57-9  N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17793  Y
ChEMBL	ChEMBL241608  Y
ChemSpider	4444104  Y
ECHA InfoCard	100.222.904
PubChem CID	5280448
UNII	09N3E8P7TA  Y
CompTox Dashboard (EPA)	DTXSID70174580
InChI InChI=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 Y Key: ZZAJQOPSWWVMBI-UHFFFAOYSA-N Y
SMILES O=C\1c3c(O/C=C/1c2ccc(OC)c(O)c2)cc(O)cc3
Properties
Chemical formula	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). N  verify  (what is  YN ?) Infobox references

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

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. ^{[3] [4] [5]}

References

1. 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.
2. 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.
3. 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 (Feb 2024). "Unveiling the potential anti-cancer activity of calycosin against multivarious cancers with molecular insights: A promising frontier in cancer research". Cancer Med. 13 (3) e6924. doi:10.1002/cam4.6924. PMC   10905684 . PMID   38230908.
4. Ren, F; Ma, Y; Zhang, K; Luo, Y; Pan, R; Zhang, J; Kan, C; Hou, N; Han, F; Sun, X (May 2024). "Exploring the multi-targeting phytoestrogen potential of Calycosin for cancer treatment: A review". Medicine (Baltimore). 103 (18) e38023. doi:10.1097/MD.0000000000038023. PMC   11062656 . PMID   38701310.
5. Lu, Q; Jiang, J; Wang, X; Wang, R; Han, X (2025). "Advancements in the Research of Astragalus membranaceus for the Treatment of Colorectal Cancer". Am J Chin Med. 53 (1): 119–146. doi:10.1142/S0192415X25500065. PMID   39880662.