Cyclic fatty acids: natural sources, formation during heat treatment, synthesis and biological properties.

This invention relates to plant fatty acid hydroxylases. Methods to use conserved amino acid or nucleotide sequences to obtain plant fatty acid hydroxylases are described. Also described is the use of cDNA clones encoding a plant hydroxylase to produce a family of hydroxylated fatty acids in transgenic plants. In addition, the use of genes encoding fatty acid hydroxylases or desaturases to alter the level of lipid fatty acid unsaturation in transgenic plants is described.

Production of hydroxylated fatty acids in genetically modified plants

Sterculia foetida oil contains cyclopropene fatty acids namely 8,9-methylene-heptadec-8-enoic acid (malvalic) and 9,10-methylene-octadec-9-enoic acid (sterculic) to an extent of 50–55%. The present study reports the preparation of biodiesel from S. foetida oil using sodium hydroxide as catalyst. The resultant biodiesel was evaluated for physico-chemical properties namely iodine value (72.6), free fatty acids (0.17%), phosphorous content (0 ppm), flash point (179 °C), cloud point (3 °C), pour point (3 °C), viscosity at 40 °C (4.72 cSt), oxidative stability at 110 °C (3.42 h), density (0.850 g/cm3 at 15 °C), and trace metals (Group I metals 0.21 ppm). The properties were compared with that of sunflower, soybean and rapeseed oil-based biodiesels and found to be comparable except for the pour point.

Preparation and Evaluation of Biodiesel from Sterculia foetida Seed Oil

Studies were conducted to characterize the metabolism of the unusual fatty acid petroselinic acid (18:1cis[delta]6) in developing endosperm of the Umbelliferae species coriander (Coriandrum sativum L.) and carrot (Daucus carota L.). Analyses of fatty acid compositions of glycerolipids of these tissues revealed a dissimilar distribution of petroselinic acid in triacylglycerols (TAG) and the major polar lipids phosphatidylcholine (PC) and phosphatidylethanolamine (PE). Petroselinic acid comprised 70 to 75 mol% of the fatty acids of TAG but only 9 to 20 mol% of the fatty acids of PC and PE. Although such data appeared to suggest that petroselinic acid is at least partially excluded from polar lipids, results of [1–14C]acetate radiolabeling experiments gave a much different picture of the metabolism of this fatty acid. In time-course labeling of carrot endosperm, [1–14C]acetate was rapidly incorporated into PC in high levels. Through 30 min, radiolabel was most concentrated in PC, and of this, 80 to 85% was in the form of petroselinic acid. One explanation for the large disparity in amounts of petroselinic acid in PC as determined by fatty acid mass analyses and 14C radiolabeling is that turnover of these lipids or the fatty acids of these lipids results in relatively low accumulation of petroselinic acid mass. Consistent with this, the kinetics of [1–14C]acetate time-course labeling of carrot endosperm and “pulse-chase” labeling of coriander endosperm suggested a possible flux of fatty acids from PC into TAG. In time-course experiments, radiolabel initially entered PC at the highest rates but accumulated in TAG at later time points. Similarly, in pulse-chase studies, losses in absolute amounts of radioactivity from PC were accompanied by significant increases of radiolabel in TAG. In addition, stereospecific analyses of unlabeled and [1–14C]acetate-labeled PC of coriander endosperm indicated that petroselinic acid can be readily incorporated into both the sn-1 and sn-2 positions of this lipid. Because petroselinic acid is neither synthesized nor further modified on polar lipids, the apparent metabolism of this fatty acid through PC (and possibly through other polar lipids) may define a function of PC in TAG assembly apart from its involvement in fatty acid modification reactions.

Apparent role of phosphatidylcholine in the metabolism of petroselinic acid in developing umbelliferae endosperm

Coriander vegetable oil was extracted from fruits of French origin in a 23% yield. The oil was of good quality, with a low amount of free fatty acids (1.8%) and a concurrently high amount of triacylglycerols (98%). It is a rich source of petroselinic acid (C18:1n-12), an important renewable building block, making up 73% of all fatty acids, with also significant amounts of linoleic acid (14%), oleic acid (6%), and palmitic acid (3%). The oil was characterized by a high unsaponifiable fraction, comprising a substantial amount of phytosterols (6.70 g/kg). The main sterol markers were β-sitosterol (35% of total sterols), stigmasterol (24%), and Δ7-stigmastenol (18%). Squalene was detected at an amount of 0.2 g/kg. A considerable amount of tocols were identified (500 mg/kg) and consisted mainly of tocotrienols, with γ-tocotrienol as the major compound. The phospholipid content was low at 0.3%, of which the main phospholipid classes were phosphatidic acid (33%), phosphatidylcholine (25%), phosphatidylinositol (17%), and phosphatidylethanolamine (17%). About 50% of all phospholipids were non-hydratable. The β-carotene content was low at 10 mg/kg, while a significant amount of chlorophyll was detected at about 11 mg/kg. An iron content of 1.4 mg/kg was determined through element analysis of the vegetable oil. The influence of fruit origin on the vegetable oil composition was shown to be very important, particularly in terms of the phospholipids, sterols, and tocols composition.

https://biblio.ugent.be/publication/8069096/file/8069110.pdf

Characterization of French Coriander Oil as Source of Petroselinic Acid.

Analyses of the phospholipids of palash(Butea monosperma), papaya(Carica papaya), jangli badam(Sterculia foetida), coriander(Coriandrum sativum) and carrot(Daucus carota) seeds are reported in the present study. Phosphatidylcholine, phosphatidylethanolamine and phosphatidylinositol were identified as major components in all the seeds. Small amounts of lysophosphatidylcholine in palash and papaya, and cardiolipin in palash, papaya and carrot also were detected. The predominant fatty acids present in the total and individual phospholipids of the seeds examined were oleic, linoleic and palmitic. In the case of palash and papaya phospholipids, the profile of fatty acid distribution was similar to that of their respective oils. However, the unusual fatty acids present predominantly in jangli badam, coriander and carrot oils were found to be significantly reduced in the respective phospholipids.

Phospholipids of palash (Butea monosperma), papaya (Carica papaya), jangli badam (Sterculia foetida), coriander (Coriandrum sativum) and carrot (Daucus carota) seeds

The Karanja (Pongamia glabra) seed kernels were extracted with a solvent mixture of chloroform and methanol (2:1, v/v). The extract was dissolved in chloroform and precipitated with acetone. Acetone insolubles (0.78% wt. of the kernels) contained 2.9 percent of phosphorus. Major constituent phospholipids were identified as phosphatidylcholine, phosphatidylethanolamine and phosphatidylinositol by spraying with characteristic spray reagents on thin-layer chromatograms (TLC) and by comparing the Rf values with those of standards and literature values. A quantitative TLC method using a colorimetric determination of phosphorus without acid digestion was used for studying the phospholipid composition of the acetone insolubles. The composition was found to be phosphatidylcholine, 43.1%; phosphatidyl-ethanolamine, 18.8%, phosphatidylinositol, 33.3% and unidentified, 4.8%. The fatty acid composition of the individual phospholipids is also reported.

S. Venkob Rao

Papers

Phospholipids of palash (Butea monosperma), papaya (Carica papaya), jangli badam (Sterculia foetida), coriander (Coriandrum sativum) and carrot (Daucus carota) seeds

Phospholipid Composition of Karanja (Pongamia glabra) Seeds