Analysis of triacylglycerols containing cyclopropane fatty acids in Sterculia fostida (Linn.) seed lipids

Pasha, Mohammed Khysar; Ahmad, Feroz

doi:10.1021/jf00016a020

Cited by 12 publications

(7 citation statements)

References 18 publications

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“…These data imply that the DHSA synthesized on sn-1 of PC may be removed from the sn-1 before desaturation and subsequently re-incorporated into PC. The positional distribution of CPE-FAs in triacylglycerols of S. foetida seeds indicates that for triacylglycerols containing only one CPE-FA, CPE-FAs are more abundant at sn-1 or 3 positions, but for triacylglycerols containing two CPE-FAs, CPE-FAs are enriched at the sn-2 position (43). These data suggest that the metabolism of cyclopropene fatty acids in seeds oils may involve several acylation steps.…”

Section: The Addition Of Methylene Group Takes Place On the Sn-1 Posimentioning

confidence: 83%

Characterization of Cyclopropane Fatty-acid Synthase fromSterculia foetida

Bao

Thelen²,

Bonaventure

et al. 2003

Journal of Biological Chemistry

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Section: The Addition Of Methylene Group Takes Place On the Sn-1 Posimentioning

confidence: 83%

Characterization of Cyclopropane Fatty-acid Synthase fromSterculia foetida

Bao

Thelen²,

Bonaventure

et al. 2003

Journal of Biological Chemistry

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“…A product that has yet to be thoroughly examined for its potential nutraceutical properties is sterculic oil (SO), a known natural inhibitor of stearoyl-CoA desaturase 1 (SCD1) [ 9 , 10 ]. Sterculic oil contains two unique cyclopropenoic fatty acids, sterculic (55%), and malvalic (10%) acids [ 11 , 12 ], which inhibit the enzymatic activity of SCD1 [ 9 , 10 ]. Recently, SCD1, a major enzyme involved in fatty acid metabolism, has emerged as a potential pharmaceutical target for the treatment of obesity and type 2 diabetes [ 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Sterculic Oil, a Natural SCD1 Inhibitor, Improves Glucose Tolerance in Obese ob/ob Mice

et al. 2012

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Obesity and its metabolic complications are associated with increased expression/activity of stearoyl-CoA desaturase-1 (SCD1), a major regulator of lipid metabolism. Reduction or ablation of this enzyme is associated with an improved metabolic profile and has gained attention as a target for pharmaceutical development. Sterculic oil (SO) is a known inhibitor of SCD1 and may provide a natural approach for treating obesity and/or insulin resistance. The purpose of this study was to evaluate the effects of SO consumption in leptin-deficient ob/ob mice, a model of obesity and insulin resistance. Five-week-old male mice received either an AIN-93G (control) or an AIN-93G diet containing 0.5% SO. After 9 weeks, SO supplementation did not alter food intake or body weight; however, the desaturase indices, a proxy of SCD1 activity, were reduced in liver and adipose tissue of SO-supplemented animals. This reduction was associated with improved glucose and insulin tolerance and attenuated hepatic inflammation in obese ob/ob mice, while no appreciable changes were observed in lean control mice receiving SO. Future studies are needed to better understand the mechanism(s) by which SO is functioning to improve glucose metabolism and to further explore the nutraceutical potential and health implications of SO supplementation.

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“…Sterculia foetida accumulates the desaturated CFA (i.e. cyclopropene fatty acid) to more than 60% of its seed oil (Bohannon and Kleiman, 1978;Pasha and Ahmad, 1992). The first step in its synthesis is the formation of the CPA by the cyclopropane synthase (CPS) enzyme, which transfers a methyl group to C9 of the oleoyl-phospholipid followed by cyclization to form the cyclopropane ring (Grogan and Cronan, 1997;Bao et al, 2002Bao et al, , 2003.…”

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confidence: 99%

Coexpressing Escherichia coli Cyclopropane Synthase with Sterculia foetida Lysophosphatidic Acid Acyltransferase Enhances Cyclopropane Fatty Acid Accumulation

Prakash

Sweet

et al. 2013

Plant Physiology

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(M.S., J.S.)Cyclopropane fatty acids (CPAs) are desirable as renewable chemical feedstocks for the production of paints, plastics, and lubricants. Toward our goal of creating a CPA-accumulating crop, we expressed nine higher plant cyclopropane synthase (CPS) enzymes in the seeds of fad2fae1 Arabidopsis (Arabidopsis thaliana) and observed accumulation of less than 1% CPA. Surprisingly, expression of the Escherichia coli CPS gene resulted in the accumulation of up to 9.1% CPA in the seed. Coexpression of a Sterculia foetida lysophosphatidic acid acyltransferase (SfLPAT) increases CPA accumulation up to 35% in individual T1 seeds. However, seeds with more than 9% CPA exhibit wrinkled seed morphology and reduced size and oil accumulation. Seeds with more than 11% CPA exhibit strongly decreased seed germination and establishment, and no seeds with CPA more than 15% germinated. That previous reports suggest that plant CPS prefers the stereospecific numbering (sn)-1 position whereas E. coli CPS acts on sn-2 of phospholipids prompted us to investigate the preferred positions of CPS on phosphatidylcholine (PC) and triacylglycerol. Unexpectedly, in planta, E. coli CPS acts primarily on the sn-1 position of PC; coexpression of SfLPAT results in the incorporation of CPA at the sn-2 position of lysophosphatidic acid. This enables a cycle that enriches CPA at both sn-1 and sn-2 positions of PC and results in increased accumulation of CPA. These data provide proof of principle that CPA can accumulate to high levels in transgenic seeds and sets the stage for the identification of factors that will facilitate the movement of CPA from PC into triacylglycerol to produce viable seeds with additional CPA accumulation.

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Analysis of triacylglycerols containing cyclopropane fatty acids in Sterculia fostida (Linn.) seed lipids

Cited by 12 publications

References 18 publications

Characterization of Cyclopropane Fatty-acid Synthase fromSterculia foetida

Characterization of Cyclopropane Fatty-acid Synthase fromSterculia foetida

Sterculic Oil, a Natural SCD1 Inhibitor, Improves Glucose Tolerance in Obese ob/ob Mice

Coexpressing Escherichia coli Cyclopropane Synthase with Sterculia foetida Lysophosphatidic Acid Acyltransferase Enhances Cyclopropane Fatty Acid Accumulation

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