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1. Prismatomerin, a new iridoid from Prismatomeris tetrandra. Structure elucidation, determination of absolute configuration, and cytotoxicity.

Author

Krohn K, Gehle D, Dey SK, Nahar N, Mosihuzzaman M, Sultana N, Sohrab MH, Stephens PJ, Pan JJ, and Sasse F

Subjects
Bangladesh, Drug Screening Assays, Antitumor, Humans, Mitosis drug effects, Molecular Structure, Plant Leaves chemistry, Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic isolation & purification, Antineoplastic Agents, Phytogenic pharmacology, Iridoids chemistry, Iridoids isolation & purification, Iridoids pharmacology, Rubiaceae chemistry
Abstract

A new complex iridoid, prismatomerin (1), has been isolated from the leaves of Prismatomeris tetrandra, together with the known glucoside gaertneroside (4). The structures of 1 and 4 were determined by spectroscopic analysis, notably 2D NMR techniques. The (1R,5S,8S,9S,10S)-(-) absolute configuration of prismatomerin (1) was determined by comparison of the vibrational circular dichroism (VCD) spectrum calculated using density functional theory and the experimental VCD spectrum of the O-acetyl derivative 3. Prismatomerin (1) showed remarkable antitumor activity and also interfered with mitotic spindle formation.

Published
2007
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