Leptoclinidamines A-C, indole alkaloids from the Australian ascidian Leptoclinides durus.
Three new indole alkaloids, leptoclinidamines A-C (1-3), were isolated from the Australian ascidian Leptoclinides durus. Their structures were determined by analysis of 2D NMR spectra. Leptoclinidamines A and B both contain an indoleglyoxylic acid attached to an L-arginine. The structure of leptoclinidamine A was confirmed by total synthesis. Leptoclinidamine C contains the naturally rare 1,3-dimethyl-5-(methylthio)histidine attached to a 6-bromoindole-3-carboxylic acid. Leptoclinidamine C (3) and both enantiomers of leptoclinidamine A (1) were tested for antimalarial, antitrypanosomal, and cytotoxic activity, but none of the compounds were bioactive.
Carroll
Anthony R
AR
Australian Rivers Institute, Griffith University, Gold Coast, Queensland, Australia. A.Carroll@griffith.edu.au
Avery
Vicky M
VM
D000818:Animals; D001315:Australia; D002738:Chloroquine / Q000494:pharmacology; D004351:Drug Resistance; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010963:Plasmodium falciparum / Q000187:drug effects; D013237:Stereoisomerism; D014346:Trypanosoma brucei brucei / Q000187:drug effects; D014561:Urochordata / Q000737:chemistry*
D026121:Indole Alkaloids; C540543:leptoclinidamine A; C540544:leptoclinidamine B; C540545:leptoclinidamine C; D002738:Chloroquine