- An unusual fatty acid and its glyceride from the marine fungus Microsphaeropis olivacea
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Two new metabolites (1 and 2) were isolated from the marine fungus Microsphaeropsis olivacea. The structures were elucidated, through analysis of the spectroscopic data, as an unusual methyl-branched unsaturated fatty acid, 10-methyl-9Z-octadecenoic acid (1), and the glyceride (2). The locations of the double bond and the methyl branching were determined from the electron impact (EI) mass spectrum of the picolinyl derivative of 1 and from MS/MS data on the hydrogenation products of 1 and 2. Two new metabolites (1 and 2) were isolated from the marine fungus Microsphaeropsis olivacea. The structures were elucidated, through analysis of the spectroscopic data, as an unusual methyl-branched unsaturated fatty acid, 10-methyl-9Z-octadecenoic acid (1), and the glyceride (2). The locations of the double bond and the methyl branching were determined from the electron impact (EI) mass spectrum of the picolinyl derivative of 1 and from MS/MS data on the hydrogenation products of 1 and 2.
- Yu, Chao-Mei,Curtis, Jonathan M.,Wright, Jeffrey L.C.,Ayer, Stephen W.,Fathi-Afshar, Ziba R.
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- Synthesis of (R,S)-10-methyloctadecanoic acid (tuberculostearic acid) and key chiral 2-methyl branched intermediates
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Tuberculostearic acid (R)-10-methyloctadecanoic acid, is a characteristic component of pathogenic mycobacteria and related organisms.Sensitive detection of this acid infected material allows rapid detection of mycobacterial disease.A novel, convergent synthesis of tuberculostearic acid and key chiral intermediates is described in this communication, to provide a reference compound.Racemic and (R)- and (S)-1-iodo-2-methyldecanes were synthesised from 1-octanal and 1-carboethoxyethylidenetriphenylphosphorane as initial starting materials. 1-Hydroxyoct-7-yne was made from 1,6-hexanediol by two alternative methods and coupled with the above racemic iodide.Hydrogenation and oxidation of the resulting (R,S)-10-methyloctadec-7-yn-1-ol gave racemic tuberculostearic acid. Keywords: Mycobacterium tuberculosis; Tuberculostearic acid; Acetylene coupling; (R,S)-10-methyloctadecanoic acid; Chiral 2-methyl branched fatty acids
- Wallace, Paul A.,Minnikin, David E.,McCrudden, Katharine,Pizzarello, Andrea
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p. 145 - 162
(2007/10/02)
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