ABSTRACT
As part of the development of an analytical technique for the detection of meridianins and related compounds in biological fluids, a crude extract of the tunicate Aplidium meridianum was analysed using neutral loss tandem mass spectrometry. The 41 u neutral loss-EI(+) mass spectrum showed molecular ions corresponding to two previously undetected alkaloids. We report herein the isolation and structure elucidation of these alkaloids, meridianins F and G.
Subject(s)
Alkaloids/analysis , Alkaloids/chemistry , Indole Alkaloids/analysis , Indole Alkaloids/chemistry , Urochordata/chemistry , Animals , Molecular Structure , Tandem Mass SpectrometryABSTRACT
[structure: see text] In the course of our search of new bioactive metabolites from marine invertebrates, paesslerins A and B, sesquiterpenoids with an unprecedented tricyclic skeleton, were isolated from the subAntarctic soft coral Alcyonium paessleri collected at a depth of 200 m near the South Georgia islands, and their structures were elucidated by spectroscopic techniques. These compounds show moderate cytotoxicity in preliminary assays.
Subject(s)
Bridged-Ring Compounds/chemistry , Cnidaria/chemistry , Sesquiterpenes/chemistry , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Biological Factors/chemistry , Biological Factors/isolation & purification , Biological Factors/pharmacology , Bridged-Ring Compounds/isolation & purification , Bridged-Ring Compounds/pharmacology , Humans , Marine Biology , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Tumor Cells, Cultured/drug effects , WorkforceABSTRACT
Fifteen illudalane sesquiterpenoids, alcyopterosins A-O (1-15) have been isolated from the subAntarctic soft coral Alcyonium paessleri which was collected at a depth of 200 m near the South Georgia Islands, and their structures were elucidated by spectroscopic techniques. Eight of these compounds (2, 3, 5-8, 10, and 13) are the first natural nitrate esters, while the other four (1, 4, 11, and 12) are chlorinated. These compounds are as well the first illudalane sesquiterpenoids to be isolated from the marine environment. Compounds 1, 3, 5, and 8 showed mild cytotoxicity toward human tumor cell lines.
Subject(s)
Cnidaria/chemistry , Esters/chemistry , Nitrates/chemistry , Nitrates/isolation & purification , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Animals , Antarctic Regions , Cell Line , Esters/isolation & purification , Esters/toxicity , Humans , Magnetic Resonance Spectroscopy , Molecular Structure , Nitrates/toxicity , Sesquiterpenes/toxicity , Spectroscopy, Fourier Transform InfraredABSTRACT
The sterol composition of the Patagonian tunicate Polizoa opuntia was examined, and twenty-four compounds were identified as having either a delta 5, delta 7, or delta 0 nucleus. Two of them, the rare 20-methylpregn-5-en-3 beta-ol and 20-ethylpregn-5-en-3 beta-ol, were previously unreported as natural products from tunicates. These compounds were present only as trace components; therefore, their structures were confirmed by synthesis from suitable precursors and by comparison of the spectral and chromatographic constants of the synthetic and natural compounds.
