Amphimic acids, novel unsaturated C28 fatty acids as DNA topoisomerase I inhibitors from an Australian sponge Amphimedon sp.

Nemoto, Takayuki; Ojika, Makoto; Sakagami, Youji

doi:10.1016/s0040-4039(97)01234-3

Cited by 40 publications

(19 citation statements)

References 10 publications

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“…Recently, Nemoto et al (10) isolated free demospongic acids as human DNA topoisomerase-I inhibitors from the sponge Amphimedon sp. and characterized them by spectral methods, including nuclear magnetic resonance (NMR) spectroscopy.…”

mentioning

confidence: 99%

A new cytotoxic fatty acid (5Z,9Z)‐22‐methyl‐5,9‐tetracosadienoic acid and the sterols from the far Eastern sponge Geodinella robusta

Makarieva

Santalova

Горшкова

et al. 2002

Lipids

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A new fatty acid, (5Z,9Z)-22-methyl-5,9-tetracosadienoic acid (1a), and a rare fatty acid, (5Z,9Z)-23-methyl-5,9-tetracosadienoic acid (2a), the predominant constituents of the free fatty acid fraction from the lipids of the sponge Geodinella robusta, were isolated and partly separated by reversed phase high-performance liquid chromatography, followed by multifold crystallization from MeOH to give 1a and 2a in 70% and 60% purity, respectively. These fatty acids were identified as (5Z,9Z)-22- and (5Z,9Z)-23-methyl-5,9-tetracosadienoic acids by nuclear magnetic resonance techniques, including distortionless enhancement by polarization transfer, heteronuclear multiple quantum connectivity, and correlation spectroscopy experiments, as well as from mass-spectrometric data for their methyl esters, the methyl esters of their perhydro derivatives, and their pyrrolidides. Mixtures of 1a and 2a showed cytotoxic activity against mouse Ehrlich carcinoma cells and a hemolytic effect on mouse erythrocytes. The sterol fraction from the same sponge was analyzed by gas-liquid chromatography-mass spectrometry, and 24-methylenecholesterol was identified as a main constituent of this fraction. The implications of the co-occurrence of membranolytic long-chain fatty acids and 24-methylenecholesterol as a main membrane sterol are discussed in terms of the phenomenon of biochemical coordination.

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confidence: 99%

A new cytotoxic fatty acid (5Z,9Z)‐22‐methyl‐5,9‐tetracosadienoic acid and the sterols from the far Eastern sponge Geodinella robusta

Makarieva

Santalova

Горшкова

et al. 2002

Lipids

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“…Little is known about biological activities of these longchain unsaturated FA, except the DNA topoisomerase I inhibition of ∆5,9,21-30:3 (9). To the best of our knowledge, this is the first report of a long-chain fatty ester as an elastase inhibitor.…”

Section: Resultsmentioning

confidence: 95%

“…Acid 5,9,21-30:3 was isolated from Amphimedon sp. and described as a DNA topoisomerase I inhibitor (9).…”

mentioning

confidence: 99%

5,9,23‐Triacontatrienoic methyl ester, an elastase inhibitor from the marine sponge Chondrilla nucula

Meyer

Guyot

2002

Lipids

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“…[1][2][3][4][5][6][7][8][9] Topoisomerase I is a key enzyme in the breaking and fixing of DNA strands and is involved in making the necessary topological changes to DNA for key cellular processes such as replication, transcription, and recombination. 1 Topoisomerases have also evolved as key cellular targets for the development of effective anticancer drugs.…”

Section: Introductionmentioning

confidence: 99%

“…1 Other interesting topo-I lipid inhibitors include conjugated C 18 and eicosapentaenoic fatty acids, 2,4 very-long chain (C 26 -C 30 ) ∆5,9 fatty acids, 5,6 and phospholipids containing unsaturated fatty acids. 7 While most of the fatty acid topoisomerase-I inhibitory work has been performed with straight-chain fatty acids, there is just one report dealing with the topoisomerase I inhibitory activity of methyl-branched iso and anteiso fatty acids.…”

Section: Introductionmentioning

confidence: 99%

An improved synthesis for the (Z)-14-methyl-9-pentadecenoic acid and its topoisomerase I inhibitory activity

Carballeira¹,

Sanabria²,

Oyola³

2006

Arkivoc

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An improved synthesis for the (Z)-14-methyl-9-pentadecenoic acid was developed based on the appropriate use of (trimethylsilyl)acetylene as the key reagent in the synthesis. The reported synthesis started with commercially available 8-bromo-1-octanol and furnished the desired acid in seven steps and in a 16% overall yield, a significant improvement over the previous reported synthesis for this fatty acid. The synthesis reported herein afforded sufficient amounts to study the acid topoisomerase I inhibitory potential and it was found that the title acid inhibits the human placenta DNA topoisomerase I enzyme at concentrations of 500 µM.

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Amphimic acids, novel unsaturated C28 fatty acids as DNA topoisomerase I inhibitors from an Australian sponge Amphimedon sp.

Cited by 40 publications

References 10 publications

A new cytotoxic fatty acid (5Z,9Z)‐22‐methyl‐5,9‐tetracosadienoic acid and the sterols from the far Eastern sponge Geodinella robusta

A new cytotoxic fatty acid (5Z,9Z)‐22‐methyl‐5,9‐tetracosadienoic acid and the sterols from the far Eastern sponge Geodinella robusta

5,9,23‐Triacontatrienoic methyl ester, an elastase inhibitor from the marine sponge Chondrilla nucula

An improved synthesis for the (Z)-14-methyl-9-pentadecenoic acid and its topoisomerase I inhibitory activity

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