Minor alkaloids of Camptotheca acuminata

Phytochemistry
1979.0

Abstract

Several camptothecin alkaloidal analogs have been isolated from the leaves and bark of Camptotheca acuminata Decne. (Nyssaceae), including (+)-camptothecin (1), 10-hydroxycamptothecin (2) and 10-methoxycamptothecin (3), which are of interest due to their anti-tumor properties and camptothecin's effect on inhibiting macromolecular synthesis. We now report the isolation from C. acuminata of the minor alkaloids 20-deoxycamptothecin (5), 20-hexanoylcamptothecin (6) and 20-hexanoyl-10-methoxycamptothecin (7). A modification of the original extraction process offering higher yields in fewer steps was employed: ground C. acuminata bark was extracted with chloroform-ethanol, followed by preliminary purification, low pressure liquid chromatography (LPLC) and preparative thin-layer chromatography (PLC). The structure of 20-deoxycamptothecin (5) was verified by comparison with racemic 5 prepared from 1 and by oxidation to 1; its stereochemistry at C-20 proved racemic as no optical rotation was exhibited. 20-Hexanoylcamptothecin (6) was identical to synthetic 6 by NMR, IR and MS. 20-Hexanoyl-10-methoxycamptothecin (7) was identified by NMR and MS.

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