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The present study juxtaposes for the first time the heterogeneous methanolysis of gmelina oil over KNO3 activated MgO-ZnO with a NaOH base methanolysis for biodiesel production. The conditions for biodiesel production such as temperature, reaction time, NaOH (or KNO3 dose) and methanol-gmelina oil ratio were optimised. The 4%w/w KNO3 activated MgO-ZnO afforded high biodiesel yield (71.5 %) at 65oC predominantly consisting of C13-C25 cuts of linear fatty acid methyl esters (FAME). This heterogeneous catalyst was characterized using X-ray diffraction (XRD), energy dispersive X-ray (EDX) analyser, scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FTIR). Gas-chromatography-mass spectrometry (GC-MS) revealed the selectivity to petroselinic acid methyl ester. The fuel properties of the biodiesel and its blends were consistent with standards. Relatively, the NaOH process yielded higher biodiesel (96.8%) at 60oC, 90 min, 1.2 % NaOH and 9:1 methanol-oil ratio.

2-Phenylethyl esters of fatty acids were prepared readily by esterification of free fatty acids or transesterification of other lipids. Compared with methyl esters, phenylethyl esters greatly improve the resolution of oleate and petroselinate by both gas and high performance liquid chromatography, and the ultraviolet absorption of the phenylethyl esters facilitates detection of the derivatives by high performance liquid chromatography (HPLC) ultraviolet detectors. The fatty acid compositions of com and soybean oil obtained by analysis of phenylethyl esters agreed with those obtained with methyl esters. The phenylethyl esters were resolved and eluted on C-18 HPLC columns with much smaller solvent volumes than those reported for other aromatic esters. ^Reprinted with permission from J. Am. Oil. Chem. Soc. 72:749-751 (1995). Copyright © 1995. ^Graduate student and Professor, respectively. Department of Food Science and Human Nutrition and Center For Crops Utilization Research. ^Author for correspondence. 18

The oleaginous yeast Apiotrichum curvatum was grown on various lipids as carbon sources. When commercial animal and vegetable oils were used as substrates, the yeast triglyceride had a fatty acid profile similar to that of the substrate oil, but the glyceride structures were altered. Saturated free fatty acids with less than 14 carbons could not be used as carbon sources by the yeast. An emulsion of palmitic acid was well utilized by the yeast, but it was extensively desaturated before being deposited in the yeast triglyceride. Stearic and arachidic acid emulsions gave very limited and no growth, respectively. Oleic acid supported very good yeast growth; eicosenoic acid supported limited growth; erucic acid gave very poor growth. The yeast grew on petroselinic acid and deposited it extensively in its triglyceride. When supplemented with 1000 ppm butylated hydroxyanisole, linoleic and linolenic acids showed excellent growth and lipid accumulation. The yeast deposited ricinoleic acid, eleostearic and vernolic acids in its triglyceride when the yeast was grown on triglycerides containing these fatty acids, but the yeast triglyceride contained less of these conjugated and oxygenated acids than were found in the substrate oils. When crambe oil was used as a carbon source for the yeast, fatty acids with 20 or more carbons were concentrated in the residual substrate oil while those with 16 and 18 carbons were almost completely utilized. When cholesterol was incorporated in the growth medium, the yeast incorporated very little of it into its depot fats.

Bixa orellana L. seeds possess a resinous lipid (6.3 %), which has a pungent and spicy odour. The seed is known for its medicinal properties such as anti-inflammatory, antipyretic activity and as a cure for tonsilitis. Trachyspermum copticum L. seed is a well known digestive aid and relief from colic pain. T. copticum possesses essential oil rich in thymol (>50 %) and lipid (15.6 %). The present study was aimed to quantify lipid classes of these two species by silicic acid chromatography and analyze their fatty acid composition by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). It was observed that the seed lipids are rich in neutral lipids with 98.1 and 95.2 % and lower quantities of glycolipids of 1.5 and 3.8 % and phospholipids of 0.36 and 1.0 % in B. orellana and T. copticum, respectively. The fatty acid composition of B. orellana seed lipid showed major quantities of palmitic (26.9 %), linoleic (26.1 %), oleic (17.5 %), linolenic (15.1 %), stearic acid (10.8 %) and small quantities of eicosanoic acid (3.6 %). In T. copticum seed lipids, petroselinic acid (68.3 %) and linoleic acid (25.3 %) together constituted 93 % of the total lipid. The results revealed that the lipids after recovery of the essential components namely, bixin and volatile oil from B. orellana and T. copticum, respectively can be further explored for industrial applications.

International audience; The implementation of renewable resources in the industrial production processes appears to be the most effective way to achieve sustainable development. However, in order to tackle the key issues of shifting to renewable resources, a full exploitation of biomass resources and efficient utilization of complex organic macromolecules and also other chemical constituents such as antioxidants in bio-refinery system will be crucial. In this regard, fennel (Foeniculum vulgare) seeds could be a promising bio-resource with significant interest as a rich source of both vegetable oil (VO) and essential oil (EO), in addition to rare phytochemicals. Thus, in the present paper, a trans-disciplinary assessment of a new bio-refinery process from fennel seeds was established: the development of an integrated valorization of fennel seeds, allowing the extraction of VO and EO and their exploitation in cosmetic applications as well as the valorization of residual by-products as a source of biologically active compounds, these processes constituted the basis of this bio-refinery concept. Laboratory obtained results and pilot-scale levels with fennel seeds reported extraction of high yield of both VO and EO (19.8% and 1.8%, respectively) with significant amounts of valuable components, petroselinic acid and trans-anethole (74.8% and 70.7%, respectively). Further, the valorization of these oils as functional ingredients in moisturizing cream formulas showed a positive impact on the overall emulsions structure and quality. Next to this, fennel oilseeds by-products exhibited a remarkable antioxidant potential with high phenols and flavonoids contents and exhibited good antimicrobial properties depending on the extract type. These promising findings are of great economic interest as they can lead to a wild range of novel, bio-based industrial applications from fennel seeds.

International audience; This study investigated 25 Tunisian plant species of 13 families based on their oil and total phenolic contents. The fatty acid profiles and antioxidant activity of phenolic extracts of these plant seeds were studied in order to identify species containing unusual fatty acids and potential antioxidants. The oil content varied from 4.2 to 66.5% of DW (Dry Weight). Fatty acid profiles were determined using gas chromatography analysis coupled to flame ionization detection and high resolution mass spectrometry (GC-FID and GC-HRMS). The results showed that plant seeds were mostly composed of classic fatty acids (palmitic, oleic, linoleic and linolenic acids), while unusual fatty acids such as long-chain and odd-chain fatty acids were minor components. However, the petro-selinic acid was the major component of Apiaceae family seed oil, particularly in Pimpinella saxifraga and Pimpinella major. The phenolic content of seed methanolic extracts, measured by Folin-Ciocalteu assay, varied between 30 and 4700 mg GAE/100 g DW. The methanolic extracts exhibited a broad range of antioxidant activity , varying from 13 to 17,000 mg TEAC/100 g DW in the DPPH assay. In the ABTS assay, the antioxidant activity values similarly varied from 4 to 18,100 mg TEAC/100 g DW. The seeds of Apium graveolens, Anethum graveolens, Pimpinella saxifraga and Lepidium sativum had high oil content, interesting fatty acid profiles and their methanolic extracts displayed high antioxidant capacities. This investigation of Tunisian plants showed the potentialities of several species that could be scale-up cultivated for commercial purposes.

The vaporization enthalpies and liquid vapor pressures at T/K = 298.15 have been evaluated by correlation gas chromatography for the following fatty acids (ΔlgHm(298.15 K)/kJ·mol–1; 108·pl298/Pa): (9Z)-hexadecenoic acid (palmitoleic acid) (123.0 ± 6.4); (6900 ± 4200), (6Z)-octadecenoic acid (petroselinic acid), (131.2 ± 2.1); (1130 ± 1000), (9Z)-octadecenoic acid (oleic acid), (132.6 ± 6.6); (1010 ± 600), (5Z,8Z,11Z,14Z)-eicosatetraenoic acid (arachidonic acid), (145.3 ± 6.8); (65 ± 37), (11Z)-eicosenoic acid (gondoic acid), (143.5 ± 2.2); (118 ± 105), (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexenoic acid (cervonic acid), (162.9 ± 2.3); (2.2 ± 2.0), (15Z)-tetracosenoic acid (nervonic acid), (170.6 ± 2.3), (1.0 ± 0.9); n-tetracosanoic acid (lignoceric acid), (170.7 ± 2.3); (1.1 ± 1.0), and n-hexacosanoic acid (cerotic acid, (177.2 ± 2.4); (0.25 ± 0.22). For those fatty acids that are solids at T/K = 298.15, the following fusion temperatures, fusion and sublimation enthalpies, and solid vapor pressures are also repor...

This research is about the natural product of coriander, or the Coriandrum species. The bioactive molecules and the health effects of this plant are constantly discussed. This paper is parallel with those publications, investigating the composition of the herb. The results of current study indicates that the Coriandrum seed is a source of fatty acids. From the publications, petroselinic acid or (6Z)-octadecenoic acid, is the major fatty acid in the coriander extracts. Previous articles reported on coriander’s chemical constituents, biological activities of the coriander’s seeds and leaves, as well as the coriander products in the retail. Indeed, coriander has a lot of uses either as a traditional medicine or spices. Different forms of coriander samples were subjected to a simple maceration by using chloroform. From the chromatographic purification of the seed crude extract, its component could include anisaldehyde, as one of the aromatic aldehyde. It is concluded that the lipid-containing fraction of the coriander seed could also consist of dipetroselin, a diglyceride.

The seed oils of eight Apiaceae species, angelica (Angelica archangelica), anise (Pimpinella anisum), caraway (Carum carvi), carrot (Daucus carota subsp. sativus), coriander (cilantro; Coriandrum sativum), cumin (Cuminum cyminum), dill (Anethum graveolens), and parsley (Petroselinum crispum), obtained by hexane extraction, are investigated for their composition. As is known for the Apiaceae family, the major fatty acid in all oils is petroselinic acid (6(Z)‐octadecenoic acid). Quantification of petroselinic and oleic acids is carried out with their 2‐methoxyethyl esters, resolving the overlap occurring for methyl esters. Linoleic acid is the second most prominent fatty acid, followed by oleic acid with lesser amounts of linolenic, palmitic, and stearic acids. Most of these seed oils contain significant amounts of specific phytochemicals, including anethole in anise, carvone in caraway and dill as well as angelica in lesser amounts, cuminaldehyde in cumin, and apiole and myristicin observed only in parsley. Minor amounts of three C16:1 isomers, Δ4, Δ6, and Δ9, are observed in all oils, thus appearing characteristic of these seed oils. The mass spectra of 2‐methoxyethyl esters are reported with a salient feature being the base peak in the mass spectrum of 2‐methoxyethyl petroselinate at m/z 84 compared to the usual m/z 55. Practical Applications: Knowledge of the composition of seed oils is of utmost significance for their use in all applications, food and non‐food. Typically, these oils are obtained by hexane extraction of the seeds. This work now shows that seed oils from the common Apiaceae family, which includes many food‐related species, contain phytochemicals, which often have physiological significance and are usually associated with other plant parts. Besides this, the mass spectra of the 2‐methoxyethyl esters of fatty acids as found in these seed oils are reported as these esters were shown in the past to be especially suitable for quantification. This information is valuable for verifying the nature of these esters. The seed oils of Apiaceae species contain a variety of specific phytochemicals. The most common fatty acid is petroselinic acid, with 2‐methoxyethyl esters known to allow quantification of this acid. The mass spectra of fatty 2‐methoxyethyl esters are reported.

The present study aimed to investigate the potential role of dietary petroselinic acid (PSA) in enhancing the n-3 long-chain polyunsaturated fatty acid (LC-PUFA) content in fish tissues. Three isolipidic casein-based diets were formulated to comprise graded levels of PSA (0, 10, or 20% of total fatty acid) with the incremented inclusion of coriander seed oil. Fish growth and nutrient digestibility were not significantly (P > 0.05) influenced by dietary PSA level. In general, dietary PSA affected the fatty acid composition of tilapia tissues and whole-body, which reflected dietary fatty acid ratios. Dietary PSA significantly (P < 0.05) increased β-oxidation, particularly on α-linolenic acid (18:3n-3) and linoleic acid (18:2n-6). This study provided evidence that PSA, a pseudoproduct mimicking the structure of 18:3n-6, did reduce Δ-6 desaturation on 18:2n-6 but, contrary to popular speculation, did not stimulate more Δ-6 desaturase activity on 18:3n-3. The overall Δ-6 desaturase enzyme activity may be suppressed at high dietary levels of PSA. Nevertheless, the n-3 and n-6 LC-PUFA biosynthesis was not significantly inhibited by dietary PSA, indicating that the bioconversion efficiency is not modulated only by Δ-6 desaturase. The deposition of n-3 LC-PUFA in liver and fillet lipids was higher in fish fed PSA-supplemented diets.

The paper deals with the investigation of the fatty oil of carom seed (Trachyspermum ammi) for its physicochemical characteristics and fatty acid composition. Oil from carom seed collected from local market was extracted with n-hexane in a glass Soxhlet apparatus. Extracted oil was dark green, burning taste, spicy in odour and soluble in n-hexane, chloroform, pet. ether and benzene. Its chemical characteristic such as acid value (6.69), Iodine value (79.39), Peroxide value (457.11), Saponification value (184.32), Unsaponified matter (9.11), Free fatty acid value as petroselinic acid (48.1) were determined by conventional method. The composition of fatty oil was determined by Gas Liquid Chromatography (GLC). From GLC analysis the main constituents of fatty oil such as Petroselinic acid (89.35%), Oleic acid (5.86%), Linoleic acid (4.79%) were determined. For the better evaluation of these spices, it is necessary to know their complete chemical composition.DOI: http://dx.doi.org/10.3329/jesnr.v5i2.14571 J. Environ. Sci. & Natural Resources, 5(2): 15-21 2012

Anis (Pimpinella anisum L.) seeds obtained from two geographic origins Tunisia (TAS) and Egypt (EAS) were studied regarding their biochemical composition and the antioxidant potential of their extracts. The results showed that the highest value of oil was detected with TAS compared to that of EAS ones. Ten (10) fatty acids were identified for the two locations and petroselinic acid was the most prevalent in oil seeds and interestingly, TAS displayed a significantly higher level of this acid than EAS. Besides, TAS exhibited slightly higher essential oil yield than the Egyptian variety and that trans-anethole was the dominant for the two provenances. In both accessions, the highest total phenolic, flavonoid and tannin content was obtained with ethyl acetate fraction. Therefore, TAS exhibited higher chelating and reducing powers than EAS which may be due to a slightly different phenolic composition between the two accession seed extracts. The phenolic compositions of TAS and EAS revealed that ethyl acetate extracts showed higher proportions of naringin, chlorogenic acid and rosmarinic acid. However, ethanol extracts were richer in larcitrin, rosmarinic acid and cirsimartin. The overall results revealed that aniseeds might constitute a novel source of natural antioxidants and could be used as food additive.

Coriander (Coriandrum sativum L.), a herbal plant, belonging to the family Apiceae, is valued for its culinary and medicinal uses. All parts of this herb are in use as flavoring agent and/or as traditional remedies for the treatment of different disorders in the folk medicine systems of different civilizations. The plant is a potential source of lipids (rich in petroselinic acid) and an essential oil (high in linalool) isolated from the seeds and the aerial parts. Due to the presence of a multitude of bioactives, a wide array of pharmacological activities have been ascribed to different parts of this herb, which include anti-microbial, anti-oxidant, anti-diabetic, anxiolytic, anti-epileptic, anti-depressant, anti-mutagenic, anti-inflammatory, anti-dyslipidemic, anti-hypertensive, neuro-protective and diuretic. Interestingly, coriander also possessed lead-detoxifying potential. This review focuses on the medicinal uses, detailed phytochemistry, and the biological activities of this valuable herb to explore its potential uses as a functional food for the nutraceutical industry.

This study is designed to examine the yield components, fatty acid, and essential oil compositions and phenolic contents fruit essential oil composition, the total phenolic amounts as well as the antioxidant activities of cumin (Cuminum cyminum L.) seeds under drought. This plant is one of the most common aromatics in the Mediterranean kitchen. Plants were treated with different levels of water deficit: control (C), moderate water deficit (MWD) and severe water deficit (SWD). Our results indicated that MWD improved the number of umbels per plant as well as the number of umbellets per umbel and the seed yield, in comparison to the control, but it decreased under SWD. Fatty acid composition analysis indicated that petroselinic acid was the major fatty acid (55.9%) followed by palmitic (23.82%) and linoleic (12.40%) acids. Water deficit enhanced the palmitic acid percentage and affected the double bound index of the fatty acid pool and thus the oil quality. The essential oil yield was 1.64% based on the dry weight and increased by 1.40 folds under MWD. Nevertheless it decreased by 37.19% under SWD in comparison to the non treated seeds. Drought results on the modification of the essential oil chemotype from γ-terpinene/phenyl-1,2 ethanediol in the control seeds to γ-terpinene/cuminaldehyde in stressed ones. Besides, total phenolic contents were higher in the treated seeds (MWD and SWD). Results suggest that water deficit treatment may regulate the production of bioactive compounds in cumin seeds, influencing their nutritional and industrial values. Besides, antioxidant activities of the extracts were determined by four different test systems, namely DPPH, β-carotene/linoleic acid chelating and reducing power assays and showed that treated seeds (MWD and SWD) exhibited the highest activity.

International audience; The aim of this work was to optimise a single-screw extruder dedicated to coriander production and to investigate the effects of screw configuration, nozzle diameter and nozzle/screw distance. On the other hand, the coriander fruit was extracted using soxhlet methods, the results were compared with mechanical screw press methods. Maximum yield was obtained with single screw extruder for a configuration allowing the strongest oil expression (nozzle/screw distance: 3 mm, nozzle diameter: 9 mm). Comparing with mechanical press, the maximum yield was obtained by the soxhlet extraction with 21.25%. The effect of the operating parameters on oil quality was not important. In all the experiments tested, the oil quality was very good. The acid value was below 1.8 mg of KOH/g of oil and iodine values were tolerable (44 mg of iodine/100 g of oil). Nine fatty acids were identified, with petroselinic acid accounting for 74-77% of the total fatty acids, followed by linoleic, oleic and palmitic acids, accounting for 12-13%, 4-6% and 3%, respectively, of the total fatty acids. beta-Sitosterol was the major sterol in all oils with 28% of total sterols of all oils. The next major sterols in all oils were stigmasterol (24-27% of total sterols) and Delta(7)-stigmasterol (14-18% of total sterols). (C) 2011 Elsevier B.V. All rights reserved.

Coriander fruits were harvested at three stages of maturity from Menzel Temime region. Oil yield and glycerolipid fractions were studied. The first results showed that oil yield increased significantly (P

A silver ion HPLC procedure is described that is suitable to determine the fatty acid composition of plant seed oils. After conversion of fatty acids to p-methoxyphenacyl derivatives, it was possible to achieve baseline resolution of all fatty acid components with 0 to 3 double bonds, including the positionally isomeric 18:1 fatty acids oleic acid (cis 9-18:1), petroselinic acid (cis 6-18:1), and cis-vaccenic acid (cis 11-18:1), in aniseed oil (Pimpinella anisum, Apiaceae) by a single gradient run on a single cation exchange column laboratory converted to the silver ion form. The UV detector response (280 nm) was linearly related to the fatty acid concentration in the range 0.01 to 3.5 mg/mL.

Oils extracted from Tunisian (Tn) and Canadian (Can) coriander0 fruits were analysed for fatty acid, sterol and tocol composition. Oil yields were 21.87 and 15.84 %for Tn and Can respectively. Petroselinic acid (C 18:1n-12) was the major fatty acid in two coriander fruit samples, with a higher proportion being found in Tn (75.66 % of total fatty acid (TFA)) than in Can (73.23 % TFA). No difference was observed in phytosterol profiles between the both samples. A total of 7 sterols were identified, (3-sitosterol which constituted the major compound. Significant differences were found in total tocol contents among representing 27.78 mg/100 g oil in Tn and 21.14 mg/ 100 g oil in Can.

Based on the fact that petroselinic acid showed good inhibitory activity (IC50 = 6.99 μmol/L) against protein tyrosine phophatase 1B(PTP1B) in vitro, a series of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives were designed and synthesized. The results indicated that most of the derivatives showed more potent activities against PTP1B. Especially, compound 13 had obvious activity with an IC50 of 106 nmol/L in vitro.

Most surfactants are based on C 12 and C 14 chains from fatty acids and contain alkanols obtained from ethylene. Readily available fatty acids with C 18 and C 22 chains are barely used due to their lower water solubility and less suitable structure for micelle formation. To overcome these deficiencies, we attached polar groups to terminal and/or internal positions of oleic, petroselinic and erucic acid. Internal diols were prepared by epoxidation and acid-catalyzed ring opening or by bishydroxylation with catalytic amounts of osmium tetroxide. Terminal alcohols were prepared by reduction of the methyl esters. For the synthesis of the non-ionic surfactants, the alcohols were reacted with the p-toluenesulfonates of di-, tri- and tetra-ethyleneglycols or the epoxide ring was opened with the corresponding oligoethyleneglycols. This way, ethoxylates free of homologues were obtained. Sodium sulfate surfactants were prepared by reacting the mono-, di- and triols with different equivalents of chlorosulfonic acid. From the purified products, the spectroscopic and the surfactant properties were determined. The latter are in many cases equal or better than those of commercial ionic and non-ionic surfactants based on C 12 and C 14 carbon chains.

BACKGROUND: The essential oil and fatty acid composition of Tunisian annual caraway (Carum carvi L.) seeds from three ecotypes was investigated by gas chromatography and gas chromatography–mass spectrometry analyses. RESULTS: Total fatty acid (TFA) proportion of caraway seeds varied from 2.95% to 5.68% (w/w). The fatty acid composition revealed that Tunisian caraway seed oil is rich in an unusual fatty acid—petroselinic acid—the proportion of which varied from 31.53% and 38.36% of TFA. Essential oil yields were relatively low and ranged from 0.86% to 1.20% (w/w). Forty-one volatile compounds were identified, the main ones being carvone (76.78–80.53%) and limonene (13.05–20.29%). CONCLUSION: Tunisian caraway seed oil is rich in an unusual fatty acid—petroselinic acid—which is of potential industrial significance. In addition, Tunisian caraway essential oil is carvone chemotype. This fact is of great economic interest due to the several applications of carvone in the alimentary and medicinal industries. Copyright © 2009 Society of Chemical Industry

The US effort for the development of new crops is directed toward the advancement of crops that can be grown in rotation with traditional commodity crops, off-season production and utilization of acreage not currently under cultivation. This effort is intended to have no or minimal impact on crop rotations that are sources for food production. The high oil content and the fatty acid profiles of mustard crops make them suitable for utilization as both fuels and base stocks for functionalized industrial chemicals. Pennycress (thlaspi arvense) and lesquerella (lesquerella fendleri) are representatives of this family and have received much attention due to their potential to grow over winter in rotation with soybean production throughout the Midwest (pennycress) or as a winter annual in the desert southwest (lesquerella). Pennycress is an oilseed crop that produces 36% oil with a wide distribution of fatty acids (principal fatty acid is erucic acid 37%) that make it suitable for production of biodiesel. The key aspect of pennycress is that its lifecycle is complete such that a full season soybean can follow its production in the same growing season. Lesquerella is an oilseed crop containing 30% oil that is composed of 60% hydroxy fatty acids. Hydroxy fatty acids are used in a wide range of industrial and cosmetic applications. Two other New Crops currently under investigation are cuphea and coriander. Cuphea is an oilseed crop that contains 35% oil that is composed of medium chain saturated fatty acids. The current cuphea variety under investigation is high in capric fatty acid (76%) with other cuphea species producing high levels of lauric acid. Cuphea can be grown throughout the Midwest but suffers from several agronomic traits that are currently limiting is potential adaptation. Coriander is also an oilseed crop with 25% oil where the main fatty acid is petroselinic acid (76%). Coriander can be grown under a short season production and has potential to rotate as a second crop following winter wheat. Petroselinic acid can be ozonolytically cleaved into adipic and lauric acids both high volume industrial chemicals.

BACKGROUND: Seed and pericarp of coriander fruit were compared in terms of essential oil, fatty acids and sterols. RESULTS: Essential oil yield of coriander samples ranged from 0.30 to 0.68% (w/w) in fruit and seed, respectively. However, in pericarp, the essential oil yield was only of 0.04% (w/w). Linalool was the major compound in the whole fruit, seed and pericarp, with 86.1%, 91.1% and 24.6% of the oils, respectively. Fatty acid composition of pericarp and seed lipids were investigated by gas chromatography. Petroselinic acid was the main compound of fruit and seed, followed by linoleic and oleic acids. Palmitic and linoleic acids were estimated in higher amounts in pericarp lipids. Total sterol contents were 36.93 g kg−1 oil in seed, 6.29 g kg−1 oil in fruit and 4.30 g kg−1 oil in pericarp. Fruit and pericarp oils were characterized by a high proportion of β-sitosterol, with 36.7% and 49.4% of total sterols, respectively. However, stigmasterol (29.5%) was found to be the sterol marker in seed oils. CONCLUSION: Coriander oil is a rich source of many compounds such as essential oils, fatty acids and sterols. This compound distribution presented significant differences between whole fruit, seed and pericarp. Copyright © 2009 Society of Chemical Industry

The fatty acid compositions of vegetable or other plant seed oils are generally determined by gas chromatography (GC). Methyl esters (the most volatile derivatives) are the preferred derivatives for GC analysis. Esters of higher alcohols are good for the separation of volatile and positional isomers. All the esters of the C1–C8 alcohols of vegetable oils were silmilarly prepared by passing the reaction mixture containing the desired alcohol, oil and tetrahydrofuran through the micro-reactor (a 3-mL dispossible syringe packed with 0.5 g of NaOH powder). The reaction products were acidified with acetic acid and the mixture was analyzed by high-performance size exclusion chromatography and GC. Transesterification was quantitative for primary alcohols, but an appreciable amount of free fatty acids was formed for secondary alcohols. Coriander seed oil was quantitatively esterified with 2-ethyl 1-hexanol with the micro-reactor in less than 1 min. Oleic and petroselinic acid 2-ethyl 1-hexyl esters are baseline separated on an Rtx-2330 capillary column (30 m×0.25 mm, 0.25 µm film thickness).

Changes on oil yield and fatty acid profiles were studied during maturation of coriander (Coriandrum sativum L.) fruits cultivated in Menzel Temime and Oued Beja, Tunisia. Oil and petroselinic acid biosynthesis proceeded at a steady rate up to 16 DAF in Oued Beja and in 33 DAF in Menzel Temime. The first results show that a rapid oil accumulation started at newly formed fruits and continued until their full maturity. During fruit maturation, fatty acid profiles varied significantly among the growing regions and stages of maturity. Petroselinic acid had the highest amount at the 16th and the 33th DAF, in Oued Beja and Menzel Temime, respectively. In Oued Beja, at full maturity, the main fatty acids were petroselinic acid (80.90 ± 9.45%), followed by oleic (14.79 ± 2.25%), palmitic (3.50 ± 0.65%) and stearic (0.49 ± 0.09%) acids. Fatty acid profile of fruits cultivated in Menzel Temime showed that in fully ripe fruit, petroselinic acid is the main compound (80.86 ± 7.23%) followed by oleic (14.83 ± 2.05%), palmitic (3.27 ± 3.12%) and stearic (0.31 ± 0.05%) acids. In both growing region, fruit development resulted mainly in an increase of petroselinic acid and a decrease of palmitic acid. Saturated and polyunsaturated fatty acids decreased significantly and monounsaturated fatty acids increased during maturation of fruit. Oil composition at the first four stages of maturity has a healthy and nutritionally value and the last stages were with important economic and industrial applications. Coriander fruit is potentially an important source of petroselinic which have numerous industrial applications.

Oils from the seeds of caraway (Carum carvi), carrot (Daucus carota), celery (Apium graveolens) and parsley (Petroselinum crispum), all from the Apiaceae family, were analyzed by gas chromatography for their triacylglycerol (TAG) composition and fatty acid (FA) distribution between the sn-1(3) and sn-2 positions of TAG. Twenty-two TAG species were quantified. Glyceryl tripetroselinate was the major TAG species in seed oils of carrot, celery and parsley, with levels ranging from 38.7 to 55.3%. In caraway seed oil, dipetroselinoyllinoleoylglycerol was the major TAG species at 21.2%, while the glyceryl tripetroselinate content was 11.4%. Other TAG species were linoleoyloleoylpetroselinoylglycerol and dipetroselinoyloleoylglycerol. Predominantly, TAG were triunsaturated (72.2-84.0%) with diunsaturates at 14.4-25.9%, and small amounts of monounsaturated TAG. Results for regiospecific analysis showed a non-random FA distribution in Apiaceae for palmitic, petroselinic, linoleic and oleic acids. Petroselinic acid was predominantly located at the sn-1(3) position in carrot, celery and parsley seed oils, while it was mainly at the sn-2 position in caraway seed oil. The distribution of linoleic acid was opposite to that of petroselinic acid. Oleic acid was mostly located at the sn-2 position, except for caraway, where it was evenly distributed between the sn-1 (3) and sn-2 positions. Both the saturated FA, palmitic and stearic acid, were located mainly at the sn-1 (3) position. The presence of a high level of tripetroselinin in parsley seed oil (55.3%) makes it a potential source for the production of petroselinic acid.

The seed oils of twenty-six species of Apiaceae belonging to the genera Bunium, Cnidium, Ferula, Ferulago, Heracleum, Hippomarathrum, Malabaila, Myrrhoides, Olymposciadium, Pimpinella, Prangos, Szovitsia, Trigonasciadium, Trinia and Zosima, collected in Turkey, were investigated for their oil content, and amount of petroselinic acid (PA), as well as for the composition of their fatty acid methyl esters (FAMEs) by GC-MS. Seed oil content ranged from 7.1% in Szovitsia callicarpa to 29.3% in Ferula haussknechtii. The results showed that the seed oils of the studied species contained high amounts of PA (1.2–72.2%), followed by significant amounts of linoleic (LA, 13.8–50.8%) and oleic (OA, 4.2–61.6%) acids. PA was found in all the analyzed species, except for Olymposciadium caespitosum, which belongs to a monotypic endemic genus of the family. According to data from our study, PA was found to be predominantly in the seed oils of Hippomarathrum cristatum (72.2%), Trinia glauca (64.9%) and Bunium microcarpum (59.7%) and, therefore these species might be considered as new sources of PA, and represent a potential oleochemical raw material. This is the first extensive study of the composition of Turkish Apiaceae species. The high amounts of PA may also have chemotaxonomic significance.

Thermal properties, powder X-ray diffraction patterns and FT-IR absorption spectra of crystals of two isomers of conjugated linoleic acid (CLA), 9-cis, 11-trans-CLA (c9t11), 10-trans, 12-cis-CLA (t10c12) were examined. To search for polymorphic modifications, we carefully performed crystallization from melt and solution phases, and isolated one type of crystalline form in c9t11 and t10c12. The melting temperature (T m) was 14.9 °C, enthalpy of fusion (ΔH) was 38.7 kJ/mol, and entropy of fusion (ΔS) was 134 J/mol K for c9t11, and T m = 19.8 °C, ΔH = 35.6 kJ/mol and ΔS = 122 J/mol K for t10c12. The X-ray diffraction and FT-IR measurements indicated O⊥ subcell packing in the crystals of c9t11 and t10c12, and long spacing values of 4.22 nm for c9t11 and 3.88 nm for t10c12. The unique molecular structures of the two isomers of CLA are discussed in comparison to the polymorphism of oleic acid, petroselinic acid, elaidic acid and linoleic acid, all of which are unsaturated fatty acids having the same carbon number of 18 as that of the two CLA isomers.

The plant family Apiaceae is known to produce a set of unusual fatty acids in the seed oils. The fatty acids and tocochromanols contents of some species of Prangos, Ferulago, Heracleum, Conium and Malabaila from Apiaceae are determined and analysed by GC, GC—MS and HPLC. Some of the studied species are endemic to Turkey. Petroselinic acid (18:1 Δ6c) is the predominant constituent and consisted of more than half of the oil. Linoleic acid is the second highest fatty acid component. There is very little variation among species in the other fatty acids. In contrast, the tocopherol compositions of the seed oils differ. Tocotrienol contents of the species (except Malabaila pastinicifolia and Ferulago pauciradiata) are found to be higher than the tocopherols, particularly in view of gamma and delta tocotrienols. The relative concentrations of petroselinic acids and tocochromanols in seed oils of Apiaceae show chemotaxonomic and phylogenetic relationships. These acids have also potential as oleochemical ...

In the extraction of oils from seeds of the genus Coriandrum, GC separations of petroselinate from oleate often gave poor resolution of these two isomers. Oleic and petroselinic acids were esterified with a series of alcohols (methanol, ethanol, 1-propanol, 2-propanol, 2-methyl-1-propanol, 1-butanol, 3-methyl-1-butanol, and 2-ethyl-1-hexanol). GC resolution of the Δ6 from the Δ9 and Δ11 octadecenoates was examined for all ester derivatives on a polar phase column. The Δ6 and Δ9 isomers were unresolved as methyl esters; however, the 2-ethyl-1-hexyl esters gave baseline separation of all three isomers under temperature programming conditions. When isothermal conditions were optimized for each ester, separation of these isomers was possible with good resolution values (>89%) for all the alcohols except methanol, which had a partial resolution of 51%. The rates of esterification of all the alcohols were determined for reactions with both oleic acid and triolein using potassium hydroxide as the esterification catalyst. Methanol gave the largest rate constant in both acid and oil esterification reactions with a rate constant 10-fold better than all of the other alcohols. Based on rates of reaction, resolution of petroselinate from oleate, and removal of residual alcohol, the ethyl ester derivative appears to be the best choice for seed oils containing petroselinic acid.

Perfluoroalkyl iodides were added in very good yields to 1,2-dialkyl substituted double bonds of e.g. petroselinic acid initiated by lead/copper(II) acetate in methanol and by copper without solvent, respectively. Using the new initiator system lead/copper(II) acetate, we also obtained good yields in the additions of perfluoroalkyl iodides to allyl alcohol and ω-unsaturated alcohols and of perfluoroalkyl 1,ω-diiodides to methyl 10-undecenoate.

A desaturase with 83% sequence identity to the coriander delta(4)-16:0-ACP desaturase was isolated from developing seeds of Hedera helix (English ivy). Expression of the ivy desaturase in Arabidopsis resulted in the accumulation of 16:1delta(4) and its expected elongation product 18:1delta(6) (petroselinic acid). Expression in Escherichia coli resulted in the accumulation of soluble, active protein that was purified to apparent homogeneity. In vitro assays confirmed delta(4) desaturation with 16:0-ACP; however, with 18:0-acyl acyl carrier protein (ACP) desaturation occurred at the delta(9) position. The ivy desaturase also converted 16:1delta(9)-ACP and 18:1delta(9)-ACP to the corresponding delta(4,9) dienes. These data suggest at least two distinct substrate binding modes, one placing C4 at the diiron active site and the other placing C9 at the active site. In the latter case, 18:0 would likely bind in an extended conformation as described for the castor desaturase with 9-carbons accommodated in the cavity beyond the dirron site. However, delta(4) desaturation would require the accommodation of 12 carbons for C16 substrates or 14 carbons for C18 substrates. The amino acids lining the substrate binding cavity of ivy and castor desaturases are conserved except for T117R and P179I (castor/ivy). Paradoxically, both substitutions, when introduced into the castor desaturase, favored the binding of shorter acyl chains. Thus, it seems likely that delta(4) desaturation would require a non-extended, perhaps U-shaped, substrate conformation. A cis double bond may facilitate the initiation of such a non-extended conformation in the monounsaturated substrates. The multifunctional properties of the ivy desaturase make it well suited for further dissection of the determinants of regiospecificity.

The occurrence of petroselinic acid (18:1delta6cis) in seed oils was believed to be limited to the Umbelliferae or Apiaceae, and a few other members of the Umbelliflorae. A major occurrence of petroselinic acid outside the Umbelliflorae must therefore be regarded as highly unusual and surprising. The seed oil of Geranium sanguineum, a member of the family Geraniaceae, has now been found to contain petroselinic and vernolic acids as major FA in its seed oil TAG. These unusual FA have not been reported previously as constituents of Geraniaceae seed oils. The structure and composition of the seed oil FA from G. sanguineum were determined by combined use of chromatographic (TLC, capillary GLC) and spectroscopic (IR, GC-MS) techniques. The double-bond position in petroselinic acid was located unambiguously by the characteristic mass fragmentation of its dimethyldisulfide (DMDS) adduct. The epoxy FA was identified as vernolic acid by co-chromatography and by the mass fragments formed during GC-MS of the products of the epoxy ring-opening reaction with BF3 in methanol.

Edible plant glycolipids (GL) are anticipated to play a role in human nutrition. Total glycolipids (TGL) were separated from black cumin (Nigella sativa L.), coriander (Coriandrum sativum L.) and niger (Guizotia abyssinica Cass.) seed oils by silica gel chromatography. Different GL subclasses were then identified and separated using high-performance liquid chromatography with ultraviolet adsorption (HPLC/UV). Separation was accomplished using Zorbax-Sil (5 μm) column with an isocratic elution by mixed solvents of isooctane/2-propanol (1:1, v/v) and detection at 206 nm. Methods are described for the analysis of GL constituents, sugar and sterols (ST), using gas–liquid chromatography equipped with flame ionization detector (GLC/FID). A relatively high level of TGL was found in all studied oilseeds. Six GL subclasses were detected in black cumin seed oil, wherein diglucosyldiacylglycerol (DGD) was the prevalent component, followed by glucocerebroside (CER). Among the TGL from coriander and niger oilseeds, acylated steryl glucoside (ASG), steryl glucoside (SG) and CER were detected. The fatty acid profiles of GL fractions from black cumin and niger seed oils was generally similar, wherein linoleic acid C18:2n-6 was the dominating fatty acid, followed by oleic acid C18:1n-9. Petroselinic acid C18:1n-12 was the fatty acid marker in GL subclasses obtained from coriander seed oil, followed by linoleic acid C18:2n-6. Four ST moieties were identified in black cumin and coriander SG and ASG fractions, while the fractions from niger oilseeds showed only three distinct ST peaks. As component sugar, glucose was the only sugar detected in all samples.