Pyranocoumarins from tropical species of the genus Calophyllum: a chemotaxonomic study of extracts in the National Cancer Institute collection.
(+)-Calanolide A, a novel dipyranocoumarin from the Malesian tree Calophyllum lanigerum var. austrocoriaceum, and a closely related compound, (-)-calanolide B, isolated from Calophyllum teysmannii var. inophylloide, are representatives of a distinct class of nonnucleoside HIV-1 specific reverse-transcriptase inhibitor under development as an AIDS chemotherapeutic. NCI repository specimens totalling 315 organic extracts from 31 taxa of Calophyllum were analyzed for related pyranocoumarins using a simple TLC system. A total of 127 extracts was initially classified as "positive"; eight out of the 31 taxa examined, representing perhaps 28 species already described (1/7-1/8 of all the species in this genus), contained prenylated coumarins, suggesting that these compounds, while sometimes abundantly present, are not widespread in the genus. Representative members of the TLC-positive extracts were partitioned between CH2C12 and 25% aqueous MeOH; the CH2C12-soluble materials were then analyzed by TLC and 1H NMR to confirm the presence of pyranocoumarins. The anti-HIV activity of the partitioned extracts are also presented. This study suggested that there are several distinctive coumarin chemotaxonomic markers distinguishing species of this genus.
Laboratory of Drug Discovery Research and Development, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Building 1052, Room 121, Frederick, Maryland 21702-1201, USA.
T C
TC
McKee
C D
CD
Covington
R W
RW
Fuller
H R
HR
Bokesch
S
S
Young
J H
JH
Cardellina II
M R
MR
Kadushin
D D
DD
Soejarto
P F
PF
Stevens
G M
GM
Cragg
M R
MR
Boyd
D019380:Anti-HIV Agents / Q000737:chemistry / Q000145:classification / Q000494:pharmacology; D002460:Cell Line; D003374:Coumarins / Q000737:chemistry* / Q000145:classification; D006801:Humans; D010936:Plant Extracts / Q000145:classification / Q000494:pharmacology; D019685:Rosales / Q000737:chemistry* / Q000145:classification; D014329:Tropical Climate
D019380:Anti-HIV Agents; D003374:Coumarins; D010936:Plant Extracts