McKee T C, Covington C D, Fuller R W, Bokesch H R, Young S, Cardellina II J H, Kadushin M R, Soejarto D D, Stevens P F, Cragg G M, Boyd M R
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.
J Nat Prod. 1998 Oct;61(10):1252-6. doi: 10.1021/np980140a.
(+)-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.
（+）-卡拉诺内酯A是一种从马来西亚树木大叶桃花心木变种（Calophyllum lanigerum var. austrocoriaceum）中提取的新型二氢吡喃香豆素，而从菲律宾桃花心木变种（Calophyllum teysmannii var. inophylloide）中分离出的一种密切相关的化合物（-）-卡拉诺内酯B，是正在开发用作艾滋病化疗药物的一类独特的非核苷HIV-1特异性逆转录酶抑制剂的代表。使用简单的薄层色谱系统，对美国国立癌症研究所（NCI）储存库中来自31种桃花心木属植物的315份有机提取物进行了分析，以检测其中相关的吡喃香豆素。共有127份提取物最初被归类为“阳性”；在所检测的31个分类群中，有8个分类群含有异戊烯基香豆素，可能代表了已描述的28个物种（该属所有物种的1/7 - 1/8），这表明这些化合物虽然有时大量存在，但在该属中并不广泛分布。对薄层色谱阳性提取物的代表性成分在二氯甲烷和25%甲醇水溶液之间进行分配；然后对二氯甲烷可溶物质进行薄层色谱和¹H核磁共振分析，以确认吡喃香豆素的存在。文中还展示了分配提取物的抗HIV活性。这项研究表明，有几种独特的香豆素化学分类学标记可区分该属的不同物种。
