The (−)-enantiomer of medicarpin.

InChI=1S/C16H14O4/c1-18-10-3-5-11-13-8-19-14-6-9(17)2-4-12(14)16(13)20-15(11)7-10/h2-7,13,16-17H,8H2,1H3/t13-,16-/m0/s1

Medicarpin, a legume phytoalexin, acts as an estrogen receptor (ER) agonist, can stimulate osteoblast differentiation likely via ERβ, promote achievement of peak bone mass, and is devoid of uterine estrogenicity; in addition, given its excellent oral bioavailability, it can be potential osteogenic agent.[1]
Medicarpin exhibits no uterine estrogenicity, however it can inhibit osteoclastogenesis and has nonestrogenic bone conserving effect in ovariectomized mice.[2]
Medicarpin and maackiain and two of their biosynthetic precursors inhibit the constitutive and phenobarbital (PB)-induced types of AHH, but have little effect on the 3-methylcholanthrene (MC)-induced type of AHH, suggests the utility of medicarpin as a probe for different forms of cytochrome P-450 in animal tissues.[3]
Medicarpin sensitizes myeloid leukemia cells to TRAIL-induced apoptosis through the induction of DR5 and activation of the ROS-JNK-CHOP pathway.[4]
Medicarpin has antifungal activity. [5]

English website: Medicarpin
Japanese website: Medicarpin
Chinese website: Medicarpin

[1] Bhargavan B, Singh D, Gautam A K, et al. J Nut Biochem, 2011, 23(1):27-38.
[2] Tyagi A M, Gautam A K, Kumar A, et al. Mol Cell Endocrinol, 2010, 325(1-2):101-9.
[3] Friedman F K, West D, Dewick P M, et al. Pharmacol, 1985, 31(5):289-93.
[4] Trivedi R, Maurya R, Mishra D P. Cell Death Dis, 2014, 5(10):1183-1208.
[5] Martínez-Sotres C, López-Albarrán P, Cruz-De-León J, et al. Int Biodeter Biodegr, 2012, 69(4):38-40.
[6] Zhao D, Wu X, Song P, et al. China Pharmacist, 2015(01):44-6.