Enantiomeric discorhabdin alkaloids and establishment of their absolute configurations using theoretical calculations of electronic circular dichroism spectra.
Enantiomeric pairs of the cytotoxic pyrroloiminoquinone marine alkaloids discorhabdins B (2), G*/I (3), L (4), and W (5) have been isolated from Latrunculia species sponges collected at different locations around the coast of New Zealand. The absolute configuration of all compounds was secured by comparison of observed data with the results of time-dependent density functional theory (TDDFT) calculations of electronic circular dichroism (ECD) spectra. Enantiomeric discorhabdins exhibit equipotent antiproliferative biological activity.
Grkovic
Tanja
T
Department of Chemistry, The University of Auckland, Private Bag 92019, Auckland, New Zealand.
Ding
Yuanqing
Y
Li
Xing-Cong
XC
Webb
Victoria L
VL
Ferreira
Daneel
D
Copp
Brent R
BR
D000470:Alkaloids / Q000737:chemistry*; D002942:Circular Dichroism; D004583:Electrons; D011789:Quantum Theory; D011809:Quinones / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D011809:Quinones