Coumestan Explained

Coumestan is a heterocyclic organic compound. Coumestan forms the central core of a variety of natural compounds known collectively as coumestans. Coumestans are oxidation products of pterocarpan^[1] that are similar to coumarin. Coumestans, including coumestrol, a phytoestrogen, are found in a variety of plants. Food sources high in coumestans include split peas, pinto beans, lima beans, and especially alfalfa and clover sprouts.^[2]

Coumestrol has about the same binding affinity for the ER-β estrogen receptor as 17β-estradiol, but much less affinity than 17α-estradiol, although the estrogenic potency of coumestrol at both receptors is much less than that of 17β-estradiol.^[3]

Because of the estrogenic activity of some coumestans, a variety of syntheses have been developed that allow the preparation of coumestans so that their pharmacological effects can be explored.^{[4] [5]}

Notes and References

1. Pharmaceutical Chemistry Journal . April 2013 . 47 . 1 . 1–11 . Synthesis and biological activity of coumestan derivatives (Review) . V. A. Tuskaev . 10.1007/s11094-013-0886-5 . 32550281 .
2. Web site: Barbour S. Warren . Carol Devine . Phytoestrogens and Breast Cancer . Program on Breast Cancer and Environmental Risk Factors . . July 2001 . 2011-03-19 .
3. Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta . Endocrinology . 139 . 10 . 1998 . 4252–4263 . 9751507 . 10.1210/endo.139.10.6216.
4. Yao, Tuanli . Yue, Dawei . Larock, Richard C . An Efficient Synthesis of Coumestrol and Coumestans by Iodocyclization and Pd-Catalyzed Intramolecular Lactonization. Journal of Organic Chemistry. 2005. 70. 24. 9985–9989. 10.1021/jo0517038. 16292831.
5. Takeda, Norihiko . Miyata, Okiko . Naito, Takeaki . Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: short synthesis of natural 2-arylbenzofurans. European Journal of Organic Chemistry. 2007. 9. 1491–1509. 10.1002/ejoc.200601001. 2007.