Additional Cytotoxic Polyacetylenes from the Marine Sponge <i>Petrosia </i>Species

Lim, Young Ja; Park, Hyun Sook; Im, Kwang Sik; Lee, Chong‐O.; Hong, Jongki; Lee, Min Young; Kim, Dong‐Kyoo; Jung, Jee H.

doi:10.1021/np000252d

Cited by 26 publications

(28 citation statements)

References 19 publications

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“…The identification of the dideoxypetrosynols, petrotetrynols (30H, 30R-U, 30W), petrotriyndiol (30V), and the homologous and epimeric petrocortynes (30D-G, 30J, 30M, 30O, 30Q) greatly expanded the number of observed alcohol configurations, chain lengths, and levels of desaturation (Fig. 34) [327,[336][337][338], suggesting that this class of metabolites may be assembled from available unsaturated fatty acid or PK precursors and subjected to environmentally controlled or subspecies-dependent hydroxylation. It was proposed by Shin that hydroxide attack on the C-21 or C-27 alkenes followed by hydride abstraction was the origin of petrocortynes E-H (30I, 30L, 30N, 30P) [327].…”

Section: Marine Fatty Acids Andmentioning

confidence: 99%

“…Interference with DNA synthesis has been mentioned to be a likely cause of their cytotoxicity [327].…”

Section: Marine Fatty Acids Andmentioning

confidence: 99%

“…34) [327,[336][337][338], suggesting that this class of metabolites may be assembled from available unsaturated fatty acid or PK precursors and subjected to environmentally controlled or subspecies-dependent hydroxylation. It was proposed by Shin that hydroxide attack on the C-21 or C-27 alkenes followed by hydride abstraction was the origin of petrocortynes E-H (30I, 30L, 30N, 30P) [327]. A chemically more facile hypothesis is that a lipoxygenase or heme-based oxygenase activity, analogous to that described earlier from algae (Section 2.3.1.3), is involved.…”

Section: Marine Fatty Acids Andmentioning

confidence: 99%

“…[327,343]. With its C 47 linear chain, nepheliosyne A (31I), isolated from the marine sponge Xestospongia sp., is one of the longest marine acetylenic acids to date (Fig.…”

Section: Marine Fatty Acids Andmentioning

confidence: 99%

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Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

286

221

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Polyacetylenic natural products are a substantial class of often unstable compounds containing a unique carbon-carbon triple bond functionality, that are intriguing for their wide variety of biochemical and ecological functions, economic potential, and surprising mode of biosynthesis. Isotopic tracer experiments between 1960 and 1990 demonstrated that the majority of these compounds are derived from fatty acid and polyketide precursors. During the past decade, research into the metabolism of polyacetylenes has swiftly advanced, driven by the cloning of the first genes responsible for polyacetylene biosynthesis in plants, moss, fungi, and actinomycetes, and the initial characterization of the gene products.The current state of knowledge of the biochemistry and molecular genetics of polyacetylenic secondary metabolic pathways will be presented together with an up-to-date survey of new terrestrial and marine natural products, their known biological activities, and a discussion of their likely metabolic origins.

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Section: Marine Fatty Acids Andmentioning

confidence: 99%

“…Interference with DNA synthesis has been mentioned to be a likely cause of their cytotoxicity [327].…”

Section: Marine Fatty Acids Andmentioning

confidence: 99%

Section: Marine Fatty Acids Andmentioning

confidence: 99%

“…[327,343]. With its C 47 linear chain, nepheliosyne A (31I), isolated from the marine sponge Xestospongia sp., is one of the longest marine acetylenic acids to date (Fig.…”

Section: Marine Fatty Acids Andmentioning

confidence: 99%

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Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

286

221

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“…The polyacetylenes from Petrosia sp. [124] are unusual in several ways: two central triple bonds are non-conjugated connected by a carbonyl group, and they contain a terminal HC=CHOH.C= group that might plausibly undergo cationoid bromination.…”

Section: Polyacetylenesmentioning

confidence: 99%

Biological Effects and Biosynthesis of Brominated Metabolites

Neilson

2003

The Handbook of Environmental Chemistry

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Abstract. On the basis of halogenated metabolites assembled by Gribble, an attempt is made to provide a hypothesis for the biosynthesis of representative groups. Examples of brominated and iodinated metabolites are drawn from the major classes of terpenoids and acetogenins, and related to the biosynthesis of their putative precursors. Brominated and iodinated carbocyclic and heterocyclic aromatic compounds are discussed as weil as mechanisms for the oxidative coupling of phenolic substrates. A few chlorinated metabolites are introduced for additional illustration. Halogenation by cationoid (Hai+) reactions catalyzed by haloperoxidases is discussed, and attention drawn to the alternative role of anionoid (Hal-) halogenation. The presentation is extended to the biosynthesis of isonitriles and dichloroimines by anionoid reaction of precursors with cyanide. The range of biota that produce brominated substrates is briefly indicated, and comments made on the ecological significance of metabolites and associations among biota.

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Characterisation of polyacetylenes isolated from carrot (Daucus carota) extracts by negative ion tandem mass spectrometry

Dilip

Brunton

Koidis

et al. 2011

Rapid Comm Mass Spectrometry

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The potential use of negative electrospray ionisation mass spectrometry (ESI-MS) in the characterisation of the three polyacetylenes common in carrots (Daucus carota) has been assessed. The MS scans have demonstrated that the polyacetylenes undergo a modest degree of in-source decomposition in the negative ionisation mode while the positive ionisation mode has shown predominantly sodiated ions and no [M+H](+) ions. Tandem mass spectrometric (MS/MS) studies have shown that the polyacetylenes follow two distinct fragmentation pathways: one that involves cleavage of the C3-C4 bond and the other with cleavage of the C7-C8 bond. The cleavage of the C7-C8 bond generated product ions m/z 105.0 for falcarinol, m/z 105/107.0 for falcarindiol, m/z 147.0/149.1 for falcarindiol-3-acetate. In addition to these product ions, the transitions m/z 243.2 → 187.1 (falcarinol), m/z 259.2 → 203.1 (falcarindiol), m/z 301.2 → 255.2/203.1 (falcarindiol-3-acetate), mostly from the C3-C4 bond cleavage, can form the basis of multiple reaction monitoring (MRM)-quantitative methods which are poorly represented in the literature. The 'MS(3) ' experimental data confirmed a less pronounced homolytic cleavage site between the C11-C12 bond in the falcarinol-type polacetylenes. The optimised liquid chromatography (LC)/MS conditions have achieved a baseline chromatographic separation of the three polyacetylenes investigated within 40 min total run-time.

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Additional Cytotoxic Polyacetylenes from the Marine Sponge Petrosia Species

Cited by 26 publications

References 19 publications

Biosynthesis and function of polyacetylenes and allied natural products

Biosynthesis and function of polyacetylenes and allied natural products

Biological Effects and Biosynthesis of Brominated Metabolites

Characterisation of polyacetylenes isolated from carrot (Daucus carota) extracts by negative ion tandem mass spectrometry

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