Prismatomerin, a new iridoid from Prismatomeris tetrandra. Structure elucidation, determination of absolute configuration, and cytotoxicity.
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.
Krohn
Karsten
K
Department of Chemistry, University of Paderborn, D-33098 Paderborn, Germany. k.krohn@uni-paderborn.de
Gehle
Dietmar
D
Dey
Sujit Kumar
SK
Nahar
Nilufar
N
Mosihuzzaman
Mohammed
M
Sultana
Nasim
N
Sohrab
Mohammed Hossain
MH
Stephens
Philip J
PJ
Pan
Jian-Jung
JJ
Sasse
Florenz
F
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001459:Bangladesh; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D039823:Iridoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008938:Mitosis / Q000187:drug effects; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry; D019666:Rubiaceae / Q000737:chemistry*
D000972:Antineoplastic Agents, Phytogenic; D039823:Iridoids; C523225:prismatomerin