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Bioorg Med Chem. 2013 Dec 15;21(24):7591-4. doi: 10.1016/j.bmc.2013.10.038. Epub 2013 Nov 1.

Bioactive compounds from Stuhlmannia moavi from the Madagascar dry forest.

Author information

1
Department of Chemistry and the Virginia Tech Center for Drug Discovery, M/C 0212, Virginia Tech, Blacksburg, VA 24061, USA.

Abstract

Bioassay-directed fractionation of the leaf and root extracts of the antiproliferative Madagascar plant Stuhlmannia moavi afforded 6-acetyl-5,8-dihydroxy-2-methoxy-7-methyl-1,4-naphthoquinone (stuhlmoavin, 1) as the most active compound, with an IC50 value of 8.1 μM against the A2780 human ovarian cancer cell line, as well as the known homoisoflavonoid bonducellin (2) and the stilbenoids 3,4,5'-trihydroxy-3'-methoxy-trans-stilbene (3), piceatannol (4), resveratrol (5), rhapontigenin (6), and isorhapontigenin (7). The structure elucidation of all compounds was based on NMR and mass spectroscopic data, and the structure of 1 was confirmed by a single crystal X-ray analysis. Compounds 2-5 showed weak A2780 activities, with IC50 values of 10.6, 54.0, 41.0, and 74.0 μM, respectively. Compounds 1-3 also showed weak antimalarial activity against Plasmodium falciparum with IC50 values of 23, 26, and 27 μM, respectively.

KEYWORDS:

1,4-Naphthoquinone; ANNNBEZJTNCXHY-NSCUHMNNSA-N; AOMAYOSPRMTXRK-NSCUHMNNSA-N; Antimalarial activity; Antiproliferative activity; CDRPUGZCRXZLFL-OWOJBTEDSA-N; DLQSYZMPSWHYMW-XYOKQWHBSA-N; Homoisoflavonoid; Leguminosae; PHMHDRYYFAYWEG-NSCUHMNNSA-N; PHRQNTXVBVJWJE-UHFFFAOYSA-N; QNVSXXGDAPORNA-SNAWJCMRSA-N; X-ray crystallography

PMID:
24239390
PMCID:
PMC3907118
DOI:
10.1016/j.bmc.2013.10.038
[Indexed for MEDLINE]
Free PMC Article
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