Stereochemistry | ABSOLUTE |
Molecular Formula | C16H14O4 |
Molecular Weight | 270.28 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12COC3=C(C=CC(O)=C3)[C@]1([H])OC4=CC(OC)=CC=C24
InChI
InChIKey=NSRJSISNDPOJOP-BBRMVZONSA-N
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
Molecular Formula | C16H14O4 |
Molecular Weight | 270.28 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Medicarpin, is a pterocarpan-type phytoalexin which is also classified as methoxylated isoflavonoid and is one of the major constituents of dietary legumes. Medicarpin is present in chickpea (Cicer arietinum), peanut (Arachis hypogaea), alfalfa (Medicago sativa), red clover (Trifolium pratense) and in an Indian medicinal plant Butea monosperma. Medicarpin, a legume phytoalexin has excellent oral bioavailability and potent antiproliferative activity against breast cancer and acute myeloid leukemia (AML) cells. Medicarpin also inhibits the oncogenic NF-kB signaling by attenuating the TNF-α-induced nuclear translocation of p65. Medicarpin stimulates osteoblast differentiation likely via estrogen receptor (ER) beta, promotes achievement of peak bone mass. Medicarpin inhibits ER stress-induced apoptosis and promotes osteoblast cell survival by targeting GRP78. Medicarpin was isolated as nematicidal constituent from the extract Taverniera abyssinica A.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Myeloid leukemia cells were incubated in culture media supplemented with dimethyl sulfoxide (DMSO) or various concentrations of Medicarpin (5, 10, 20, 50, 100 uM) or TRAIL (1, 2.5, 5, 10, 25 ng) for 48 h. Medicarpin alone significantly reduced Myeloid leukemia cell viability at higher doses and showed sensitization with various doses of TRAIL in all the cell lines at a dose of 20 uM.