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.
McKee
T C
TC
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.
Covington
C D
CD
Fuller
R W
RW
Bokesch
H R
HR
Young
S
S
Cardellina II
J H
JH
Kadushin
M R
MR
Soejarto
D D
DD
Stevens
P F
PF
Cragg
G M
GM
Boyd
M R
MR
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