Bioactive compounds from Stuhlmannia moavi from the Madagascar dry forest.
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.
Department of Chemistry and the Virginia Tech Center for Drug Discovery, M/C 0212, Virginia Tech, Blacksburg, VA 24061, USA.
Yixi
Y
Liu
Liva
L
Harinantenaina
Peggy J
PJ
Brodie
Jessica D
JD
Bowman
Maria B
MB
Cassera
Carla
C
Slebodnick
Martin W
MW
Callmander
Richard
R
Randrianaivo
Etienne
E
Rakotobe
Vincent E
VE
Rasamison
Wendy
W
Applequist
Chris
C
Birkinshaw
Gwilym P
GP
Lewis
David G I
DG
Kingston
D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D029911:Caesalpinia / Q000737:chemistry*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008270:Madagascar; D008958:Models, Molecular; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D018515:Plant Leaves / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014197:Trees / Q000737:chemistry*
D000962:Antimalarials; D000972:Antineoplastic Agents, Phytogenic
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