Santalum insulare Acetylenic Fatty Acid Seed Oils: Comparison within the Santalum Genus

The fatty acids (±)-2-methoxy-6Z-heptadecenoic acid, (±)-2-methoxy-6-hepta-decynoic acid, and (±)-2-methoxyheptadecanoic acid were synthesized and their inhibitory activity against the Leishmania DNA topoisomerase IB enzyme (LdTopIB) determined. Both 2-OMe-17:1 fatty acids were synthesized from 4-bromo-1-pentanol, the olefinic fatty acid in 10 steps and in 7 % overall yield, while the acetylenic fatty acid in 7 steps and in 14 % overall yield. The 2-OMe-17:0 acid was prepared in 6 steps and in 42 % yield from 1-hexa-decanol. The 2-OMe-17:1 acids inhibited LdTopIB, with the acetylenic acid displaying an EC50 = 16.6 ± 1.1 μM, but the 2-OMe-17:0 acid did not inhibit LdTopIB. The (±)-2-methoxy-6Z-heptadecenoic acid preferentially inhibited LdTopIB over the human TopIB enzyme. Unsaturation seems to be a prerequisite for effective inhibition, rationalized in terms of weak intermolecular interactions between the active site of LdTopIB and either the double or triple bonds of the fatty acids. Toxicity toward Leishmania donovani promastigotes was also investigated, resulting in the order acetylenic > olefinic > saturated with the (±)-2-methoxy-6-heptadecynoic acid displaying an EC50 = 74.0 ± 17.1 μM. Our results indicate that α-methoxylation decreases the toxicity of C17:1 fatty acids toward L. donovani promastigotes, but improves their selectivity index.

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Prospects and potential of fatty acid methyl esters of some non-traditional seed oils for use as biodiesel in India

Biomass and Bioenergy ◽

10.1016/j.biombioe.2005.05.001 ◽

2005 ◽

Vol 29 (4) ◽

pp. 293-302 ◽

Cited By ~ 534

Author(s):

M MOHIBBEAZAM ◽

A WARIS ◽

N NAHAR

Keyword(s):

Fatty Acid ◽

Fatty Acid Methyl Esters ◽

Methyl Esters ◽

Seed Oils ◽

Acid Methyl

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IDENTIFICATION OF CONJUGATED TRIENE FATTY ACIDS IN CERTAIN SEED OILS

Canadian Journal of Chemistry ◽

10.1139/v62-319 ◽

1962 ◽

Vol 40 (11) ◽

pp. 2078-2082 ◽

Cited By ~ 23

Author(s):

C. Y. Hopkins ◽

Mary J. Chisholm

Keyword(s):

Fatty Acid ◽

Eleostearic Acid ◽

Octadecatrienoic Acid ◽

Seed Oils ◽

Punicic Acid ◽

Calendula Officinalis ◽

Conjugated Fatty Acid ◽

Mild Conditions ◽

Conjugated Triene ◽

Major Acid

Seed oils were hydrolyzed under mild conditions and the major conjugated fatty acid of each oil was isolated and identified. In two families, species which were closely related botanically contained different but isomeric acids. Thus, in the Bignoniaceae, Jacaranda chelonia had cis trans,cis-8,10,12-octadecatrienoic acid as a major acid while Catalpa speciosa had trans,trans,cis-9,11,13-octadecatrienoic acid. In the Cucurbitaceae, Momordica charantia had the ordinary cis,trans,trans-9,11,13-octadecatrienoic (α-eleostearic) acid while M. balsamina had cis,trans,cis-9,11,13-octadecatrienoic (punicic) acid. M. balsamina is a new and convenient source of punicic acid. α-Eleostearic acid was identified as a major acid in examples of Valerianaceae and Rosaceae. Further proof was obtained that the fatty acid of Calendula officinalis (Compositae) is trans,trans,cis-8,10,12-octadecatrienoic acid.

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