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Bioactive compounds from Stuhlmannia moavi from the Madagascar dry forest.

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.
AuthorsYixi Liu, Liva Harinantenaina, Peggy J Brodie, Jessica D Bowman, Maria B Cassera, Carla Slebodnick, Martin W Callmander, Richard Randrianaivo, Etienne Rakotobe, Vincent E Rasamison, Wendy Applequist, Chris Birkinshaw, Gwilym P Lewis, David G I Kingston
JournalBioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 21 Issue 24 Pg. 7591-4 (Dec 15 2013) ISSN: 1464-3391 [Electronic] England
PMID24239390 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2013 Elsevier Ltd. All rights reserved.
Chemical References
  • Antimalarials
  • Antineoplastic Agents, Phytogenic
Topics
  • Antimalarials (chemistry, isolation & purification, pharmacology)
  • Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
  • Caesalpinia (chemistry)
  • Cell Line, Tumor
  • Cell Proliferation (drug effects)
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Madagascar
  • Models, Molecular
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Plant Leaves (chemistry)
  • Plant Roots (chemistry)
  • Plasmodium falciparum (drug effects)
  • Structure-Activity Relationship
  • Trees (chemistry)

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