Antifungal Properties of n-Alkoxyacetic Acids and Their Methyl Esters

Gershon, Herman; Shanks, Larry; Deangelis, Alan

doi:10.1002/jps.2600680125

Cited by 13 publications

(5 citation statements)

References 16 publications

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“…incorporation in the cells, as < 12 C fatty acids Greater activity of short chain ( < 12 C) than are not cellular components of dermatophytes long chain ( > 12 C) fatty acids is recognized in [29]. Acholeplasma laidlawii incorporates most the present study which confirms previous reports efficiently those exogenous saturated fatty acids [3, [24][25][26][27][28]. Higher activity of short chain fatty (C 13 : 0, C 16 : 0) in membranes that most closely A. P. GARC & J. MULLER Table 3.…”

Section: Discussionsupporting

confidence: 90%

Fungitoxicity of fatty acids against dermatophytes

Garg

Müller

1993

Mycoses

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Summary. Ten saturated and three unsaturated fatty acids over a wide spectrum of their carbon chain length were tested for their fungitoxicity against five dermatophytes. The experiments showed that short chain saturated fatty acids (C 7:0‐C 11:0) are more toxic to dermatophytes than long chain ones (> C 12:0). The antifungal activity decreases with increasing carbon chain length in the even‐numbered carbon chain series. Odd‐numbered carbon fatty acids show irregularities in these respects. Undecanoic acid (C11:0) is outstandingly most toxic in the C7:0‐C18:0 series. Polyunsaturated fatty acids are more toxic than their corresponding saturated acids. The per cent growth inhibition decreased from day 4 to day 12 at all concentrations suggesting the degradation and/or utilization of fatty acids by the fungi during the observation period. The results are discussed on the background of the biochemistry of fatty acids. Zusammenfassung. Zehn gesättigte und drei ungesättigte Fettsäuren unterschiedlicher Koh‐lenstoflkettenlänge wurden auf ihre Fungitoxizität gegen fünf Dermatophyten geprüft. Die Studie führte zu folgenden Ergebnissen: Kurzkettige gesättigte Fettsäuren (C7: 0‐C11:0) sind toxi‐scher als langkettige (>C12:0). Die antimyze‐tische Aktivität sinkt mit steigender Kettenlänge in der geradzahligen C‐Kettenserie, während ungeradzahlige Fettsäuren Irregularitäten zeigen. Undekanonsäure (C11:0) ist die am starksten toxische in der C7:0‐C18: O‐Reihe. Mehrfach ungesättigte Fettsäuren sind toxischer als ihre korrespondierenden gesättigten Fettsäuren. Der Prozentsatz der Wachstumshemmung nahm vom Bebrütungstag 4 bis Tag 12 bei allen Konzentrationen ab. Dies spricht für einen Abbau bzw. eine Nutzung der Fettsäuren durch die Pilze während der Beobachtungsdauer. Die Befunde werden auf dem Hintergrund der Biochemie der Fettsäuren diskutiert.

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Section: Discussionsupporting

confidence: 90%

Fungitoxicity of fatty acids against dermatophytes

Garg

Müller

1993

Mycoses

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“…Despite their efficacy, their utility is limited by a high lipid solubility and rapid enzyme degradation. In general, fatty acids, such as myristic acid, are metabolized by u-, 13-and co-oxidation (Klein et al, 1971) and are ineffective for systematic use, in spite of their low toxicities, because they are metabolized by the host via the usual fatty acid pathways (Gershon et al, 1978). Accordingly, 5' -rnonoesters of thymidine (dThd) may offer a method to deliver myristic acid analogues more efficiently,…”

Section: Introductionmentioning

confidence: 99%

Syntheses and Biological Evaluation of 5′-O-Myristoyl Derivatives of Thymidine against Human Immunodeficiency Virus

Parang

Wiebe

Knaus

1997

Antivir Chem Chemother

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; Fax: + 1 403 492 1217.--S ummary A series of 5'-O-acyl derivatives of thymidine (dThd) were prepared by direct acylation of thymidine using the Mitsunobu reaction. Further reaction of the bromo analogues with sodium azide gave azido ester analogues. Anti-human immunodeficiency virus type 1 (HIV-1) activities were determined against HIV-infeeted T4 lymphocytes. 5'-0-( 12-Azidododecanoyl)thymidine exhibited moderate activity (EC so 4.6 11M) against HIVinfected T4 lymphocytes. 5'-0-(2-Bromotetradecanoyl)-thymidine was found to be the most stable ester (t 1/2 15.3 min) to hydrolysis by porcine liver esterase in vitro. Partition coefficients (P) in n-octanol-phosphate buffer were determined (log1 Prange 4.15-6.72) and compared with the theoreticaPvalues calculated (log10 P 3.96-6.53) using the PALLAS program. Anti-HIV structure-activity data suggest that the experimental partition coefficient should be in the 10glo P 4.6-4.8 range for optimum anti-HIV activity. The structures of these thymidine analogues were optimized using molecular mechanics (MM+ force field) and semi-empirical quantum mechanics PM3 calculations. The moderately active compounds adopted a similar C-2' endo sugar conformation and exhibited similar energies for the lowest energy conformer. A quantitative structure-activity relationship (QSAR) regression equation was developed, based on the optimized structures and anti-HIV data using the SciQSAR program, which showed that log P was a determinant of anti-HIV activity.

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“…A previous study has reported that anthraniloyl‐CoA:methanol acyltransferase was also found to be active with methanol to produce the methyl anthranilate in Washington Concord grapes, which plays both defensive and attractive roles in enhancing plant fitness and survival in nature (Wang and De Luca 2005). Gershon et al (1979) have also reported that the methyl esters had been linked with antifungal properties. These findings indicate that the MdAAT2 might be a potential stress‐related gene.…”

Section: Resultsmentioning

confidence: 97%

Overexpression of the apple alcohol acyltransferase gene alters the profile of volatile blends in transgenic tobacco leaves

Shen

et al. 2008

Physiologia Plantarum

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Alcohol acyltransferases (AATs) are key enzymes in ester biosynthesis. Previous studies have found that AAT may be a stress-related gene. To investigate further the function of the apple alcohol acyltransferase gene (MdAAT2), transgenic tobacco plants overexpressing MdAAT2 were generated. Gas chromatography-mass spectroscopy analysis showed that the volatile blends were altered in these transgenic tobacco leaves. Although no apple-fruity volatile esters were detected in transgenic tobacco leaves, methyl caprylate, methyl caprate, and methyl dodecanoate were newly generated, and the concentrations of methyl benzoate and methyl tetradecanoate were significantly increased, suggesting that MdAAT2 may use medium-chain fatty acyl CoA and benzoyl-CoA as acyl donors together with methanol acceptors as substrates. Surprisingly, the concentrations of linalool were significantly increased in transgenic tobacco leaves, which may mediate the repellent effect on Myzus persicae (Sulzer) aphids. Using methyl jasmonate (MeJA) and wounding treatments, we found that MdAAT2 may substitute for the partial ability of MeJA to induce the production of linalool in transgenic plants. These data suggest that MdAAT2 may be involved in the response to the MeJA signal and may play a role in the response to biotic and abiotic stress.

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Antifungal Properties of n-Alkoxyacetic Acids and Their Methyl Esters

Cited by 13 publications

References 16 publications

Fungitoxicity of fatty acids against dermatophytes

Fungitoxicity of fatty acids against dermatophytes

Syntheses and Biological Evaluation of 5′-O-Myristoyl Derivatives of Thymidine against Human Immunodeficiency Virus

Overexpression of the apple alcohol acyltransferase gene alters the profile of volatile blends in transgenic tobacco leaves

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