Overcrowding factors of mosquito larvae. 10. Structure-activity relationship of 3-methylalkanoic acids and their esters against mosquito larvae

Hwang, Yih‐Shen; Navvab-Gojrati, H. A.; Mulla, Mir S.

doi:10.1021/jf60217a068

Cited by 10 publications

(10 citation statements)

References 5 publications

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“…6 Moreover, it is also known that 3-methylpentadecanoic acid, which was also identified in C. podatypa, has larvicidal activity against the mosquito larvae of Culex pipiens quinquefasciatus. 10 In addition, 10-methylpentadecanoic acid, also identified in this C. podatypa, has been identified in the phospholipids of the sulfate-reducing bacterium Desulfobacter. 11 Despite all of these findings, 11-methylpentadecanoic acid remained elusive until this report.…”

mentioning

confidence: 90%

“…The 11-methylpentadecanoic acid is of interest because other methyl-branched hexadecanoic acids, in particular the 13-methylpentadecanoic acid, display antimicrobial activity against the cariogenic Streptococcus mutans . Moreover, it is also known that 3-methylpentadecanoic acid, which was also identified in C. podatypa , has larvicidal activity against the mosquito larvae of Culex pipiens quinquefasciatus . In addition, 10-methylpentadecanoic acid, also identified in this C. podatypa , has been identified in the phospholipids of the sulfate-reducing bacterium Desulfobacter .…”

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confidence: 99%

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Identification and Total Synthesis of Novel Fatty Acids from the Caribbean Sponge Calyx podatypa

1998

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The phospholipid fatty acid composition of the Caribbean sponge Calyx podatypa was studied, and 85 different fatty acids were identified, in particular the 11-methylpentadecanoic acid and 10-tricosenoic acid, which have no literature precedence. Structural characterization was accomplished by means of gas chromatography-mass spectrometry on their corresponding methyl esters and dimethyl disulfide derivatives. The structure of 11-methylpentadecanoic acid was further confirmed by total synthesis (17% overall yield) starting from commercially available 10-hydroxydecanoic acid.

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confidence: 90%

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confidence: 99%

Identification and Total Synthesis of Novel Fatty Acids from the Caribbean Sponge Calyx podatypa

1998

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“…The relative abundances of these unusual fatty acids is high in mammalian skin tissue and it has been speculated that they prevent invasion of microorganisms by hindering their metabolic functions (Nicolaides 1974). Furthermore, 3-methylalkanoic acids have been found to possess larvicidal activity against the southern house mosquito Culex pipiens quinquefasciatus in rabbit fat (Hwang et al 1978). Because domestic sewage contains high levels of coliform bacteria, it would be expected that oysters deployed at the sewage disturbed locations are continually challenged with coliform bacteria from the surrounding waters.…”

Section: Comparison Of Sewage-disturbed and Control Location Lipid Prmentioning

confidence: 99%

The Use of Lipid Metabolic Profiling to Assess the Biological Impact of Marine Sewage Pollution

Avery

Dunstan

Nell

1998

Archives of Environmental Contamination and Toxicology

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Sydney rock oysters, Saccostrea commercialis, were deployed for a 3-month period at sewage-disturbed and control marine locations in the Hunter Region, New South Wales, Australia. After this period, the oysters were retrieved and the gills dissected and extracted for analysis of the saponified lipid components (including fatty acids and sterols), using gas chromatography-mass spectrometry (gc-ms). Multivariate analysis (discriminant function) of the gc-ms lipid profiles indicated that the lipid homeostasis in oysters from the sewage locations was significantly different compared with that observed in oysters from control locations (p < 0.0001). The primary factor discriminating between sewage and control locations was the level of beta-sitosterol, a plant sterol derived from domestic sewage and marine algae. The results indicate that gill lipid metabolism differentially alters in response to deployment of oysters into either sewage-contaminated or control locations. This method of analysis provides a sensitive measure for the biological impact of composite waste cocktails on strategically located marker organisms in affected environments.

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“…3-Methylalkanoic acids have been reported to occur in Surakhany crude oil (9) and in rabbit fat (10). The importance of the latter compounds lies in the fact that they have been found to possess larvicidal activity against the southern house mosquito Culexpipiens quinquefasciatus (11).…”

Section: 7mentioning

confidence: 99%

“…18-Methyl-5,9-tcosadienoic acid methyl ester 163 (4), 154(4), 152(2.6), 150(14), 149 (10), 145(1.5), 141(27), 136 (13), 135 (11), 123(9), 119 (3), 115 (2), 111 (11), 110 (20), 109(48), 108 (11), 107(8), 105(3), 101 (2.5), 99(16), 97 (23) , 95(31), 93(12), 91 (8), 87 (10), 85 (12), 83 (35) , 82 (36), 81(100), 80 (23), 79 (27), 74 (25), 69 (48), 68 (25), 67 (77), 57 (46); ir v max (CHClj) 2969, 2939, 2885, 1745, 1462, 1378, 1310, 1244, 1169, 1057,722 cm-1.…”

Section: 7mentioning

confidence: 99%

Identification and Characterization of Two New Methylicosadienoic Acids from Erylus formosus

Carballeira¹,

Negrón²

1991

J. Nat. Prod.

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The novel fatty acids 18-methyl-5,9-icosadienoic acid [1] and 19-methyl-5,9-icosadienoic acid [2] were identified in the Caribbean sponge Erylus formosus. Other interesting fatty acids identified were the branched acids 3-methylpentadecanoic acid and 3-methylhexadecanoic acid, which are known to possess larvicidal activity. The most stable conformation of the new acid 19-methyl-5,9-icosadienoic acid is also presented as predicted by Molecular Mechanics (MM2) calculations. The sterol composition of E. formosus is also reported.

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Overcrowding factors of mosquito larvae. 10. Structure-activity relationship of 3-methylalkanoic acids and their esters against mosquito larvae

Cited by 10 publications

References 5 publications

Identification and Total Synthesis of Novel Fatty Acids from the Caribbean Sponge Calyx podatypa

Identification and Total Synthesis of Novel Fatty Acids from the Caribbean Sponge Calyx podatypa

The Use of Lipid Metabolic Profiling to Assess the Biological Impact of Marine Sewage Pollution

Identification and Characterization of Two New Methylicosadienoic Acids from Erylus formosus

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