title: Equilibrating isomers: bromoindoles and a seco-xanthine encountered during a study of nematocides from the southern Australian marine sponge Hymeniacidon sp.
abstract: 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.
authors.affiliation: School of Chemistry, University of Melbourne, Parkville, Victoria 3010, Australia. r.capon@unimelb.edu.au
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Capon
authors.forename: Colin
authors.initials: C
authors.lastname: Skene
authors.forename: Dat
authors.initials: D
authors.lastname: Vuong
authors.forename: Ernest
authors.initials: E
authors.lastname: Lacey
authors.forename: Jennifer H
authors.initials: JH
authors.lastname: Gill
authors.forename: Kirstin
authors.initials: K
authors.lastname: Heiland
authors.forename: Thomas
authors.initials: T
authors.lastname: Friedel
mesh_terms: 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
chemical_list: D000969:Antinematodal Agents; D001965:Bromides; D007211:Indoles; D014966:Xanthenes; C456051:hymeniacidin