Equilibrating isomers: bromoindoles and a seco-xanthine encountered during a study of nematocides from the southern Australian marine sponge Hymeniacidon sp.
Bioassay-directed fractionation of a Hymeniacidon sp. yielded as nematocidal agents the equilibrating E/Z bromoindole ethyl esters 1 and 2 and corresponding methyl esters 3 and 4. Also isolated for the first time as a natural product was an equilibrating mixture of seco-xanthine formamides, attributed the trivial name hymeniacidin (5). The structure for 5 was assigned on the basis of detailed spectroscopic analysis and total synthesis.
Capon
Robert J
RJ
School of Chemistry, University of Melbourne, Parkville, Victoria 3010, Australia. r.capon@unimelb.edu.au
Skene
Colin
C
Vuong
Dat
D
Lacey
Ernest
E
Gill
Jennifer H
JH
Heiland
Kirstin
K
Friedel
Thomas
T
D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001315:Australia; D001965:Bromides / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera; D013237:Stereoisomerism; D014966:Xanthenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000969:Antinematodal Agents; D001965:Bromides; D007211:Indoles; D014966:Xanthenes; C456051:hymeniacidin