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Identification of the Unsaturated Heptadecyl Fatty Acids in the Seed

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Identification of the Unsaturated Heptadecyl Fatty Acids in the Seed J Am Oil Chem Soc (2012) 89:1599–1609 DOI 10.1007/s11746-012-2071-5 ORIGINAL PAPER Identification of the Unsaturated Heptadecyl Fatty Acids in the Seed Oils of Thespesia populnea and Gossypium hirsutum Michael K. Dowd Received: 29 December 2011 / Revised: 25 March 2012 / Accepted: 5 April 2012 / Published online: 4 May 2012 Ó AOCS (outside the USA) 2012 Abstract The fatty acid composition of the seed oils of (17:1) and heptadecadienoic (17:2) acids, which were Thespesia populnea and cotton variety SG-747 (Gossypium reported to be present at levels of about 0.1 % each. hirsutum) were studied to identity their 17-carbon fatty Because of their small concentrations, these components acids. With a combination of chemical derivatization, gas have largely been ignored in studies on cottonseed oil chromatography, and mass spectrometry, 8-heptadecenoic composition [3–5]. Consequently the positioning of the acid, 9-heptadecenoic acid, and 8,11-heptadecadienoic double bonds in these compounds has never been deter- acids were identified in both oils. Additionally, traces of mined, and their origins have not been discussed. 10-heptadecenoic acid were identified in the T. populnea As part of an in-progress survey of the seed fatty acid oil. Although these odd-carbon number fatty acids are composition of wild Gossypium species, seeds of several present in only minor amounts in cottonseed oil, they make related plant genera were also evaluated. Among these up about *2 % of the fatty acids in T. populnea seed oil. were seeds of Thespesia populnea. Chromatography of the The identification of these acids indicates that fatty acid methyl esters from this plant’s seed oil suggested that the a-oxidation is not restricted to cyclopropene fatty acids in oil contained 10- to 20-fold higher levels of these odd- these plants, but also occurs with unsaturated fatty acids. chain fatty acids, which have not been mentioned in prior Combined with malvalic acid (generally accepted as being analyses of the plant’s oil [6–8]. formed by a-oxidation of sterculic acid), *7 % of the fatty T. populnea is a small- to medium-sized flowering tree acids in T. populnea seed have under gone a-oxidization. that is widely distributed in the tropics. Its wood is used in The results should help clarify the composition of T. pop- many cultures for carving small ornamental and utilitarian ulnea seed oil, which has been reported inconsistently in objects. Like the cotton plant, the Thespesia genus is part the literature. of the Gossypieae tribe within the Malvoideae subfamily of Malvaceae plants. The plant is a gossypol producer, and its Keywords a-Oxidation Á Cottonseed Á Cyclopropenoid bark was the original source material for the isolation of fatty acids Á Heptadecyl fatty acids Á Malvaceae plants (?)-gossypol [9]. Other unusual terpenoid compounds have also been isolated from its hardwood [10]. T. populnea is thought to originate from India but has become established Introduction throughout the tropics. Consequently, the plant has many common names, including Portia tree (Caribbean), Milo In early communications, Fisher and coworkers [1, 2] noted (South Pacific), Tulip Tree (India), Pacific Rosewood that cottonseed oil contained small levels of heptadecenoic (Australia), and Seaside Mahoe (USA). To give a better account for the composition of this oil and to allow for comparisons between the seed oils of this plant M. K. Dowd (&) tribe, the identities of these acids were needed. These were Commodity Utilization Research Unit, Agricultural Research determined by a combination of chemical derivatization Service, US Department of Agriculture, 1100 Robert E. Lee Blvd, New Orleans, LA 70124, USA methods coupled with gas chromatography and mass spec- e-mail: [email protected] trometry. The origin of these components is also discussed. 123 1600 J Am Oil Chem Soc (2012) 89:1599–1609 Experimental Methods For identifying fatty acids and determining fatty acid profiles, single seeds were dehulled and extracted in indi- Materials vidual microcentrifuge tubes as described above. Between 1 and 1.5 mL of hexane was used to produce miscellas Seeds of a commercial Upland cotton (Gossypium hirsu- containing 20–30 mg/mL of extracted crude oil. tum) variety (SG 747) were obtained from an ARS cotton research program in Stoneville, MS, USA. Seeds of Derivatization Chemistry T. populnea were collected from trees growing just above the shoreline along the gulf coast of Central Florida (USA). To prepare fatty acid methyl ester (FAME) derivatives, Seed of Asclepias syriaca (milkweed) were purchased from 200 lL of methanolic base was mixed with *1mLof Everwilde Farms (Sand Creek, WI, USA) and were used to freshly extracted miscella in a screw-capped test tube. With confirm the elution time of the methyl ester of 9,12-hex- periodic vortex mixing, each solution was heated at 70 °C adecadienoic acid (9,12-16:2), which was also identified in for 10 min. After allowing the tubes to cool to room tem- both seed oils. Methanolic base, dimethyl disulfide perature, 1 mL of hexane and 1 mL of a saturated NaCl (DMDS), 3-hydroxymethylpyridine (i.e., 3-pyridylcarbi- solution were added, and the samples were vortex mixed nol), tert-butoxide in tetrahydrofuran, dichloromethane, again. The contents were then allowed to settle into organic and N-methyl-N-(trimethylsilyl)fluoroacetamide were pur- and aqueous layers. The organic phase was recovered and chased from Sigma-Aldrich (St. Louis, MO, USA) or their was used directly for chromatography or was dried with Supelco subsidiary (Bellefonte, PA, USA). Methyl ester anhydrous sodium sulfate for further derivatization. standards of vernolic acid and dihydrosterculic acid To prepare thiomethyl adducts, a procedure similar to (CPA19:0) were purchased from Matreya, LLC (Pleasant that described in the AOCS Lipid Library was used [12]. Gap, PA, USA). A volume of the FAME mixture was taken to yield *10 mg of esters; the hexane was evaporated under a Oil Content and Iodine Value stream of dry nitrogen; and the esters were re-dissolved in 1 mL of DMDS. Two hundred microliters of a 60 mg/mL Seeds were sectioned with a razor blade and were dehulled solution of iodine in diethyl ether was then added to by hand. The kernels were ground in a Braun hand chopper catalyze the reaction. Each tube was capped and allowed to pass a #20-mesh sieve and were then freeze dried. to mix gently at room temperature overnight (*16 h). Approximately 5.0 g of dry ground tissue was prepared The next morning, 5 mL of hexane was added to each from each seed source. To determine the kernel oil content, sample, and the contents were mixed. Solutions were then *1.5 g of each sample was extracted with 40 mL of washed two-to-three times with 1 mL portions of a 5 % petroleum ether in a Soxtec extractor (Foss North America, (w/v) aqueous sodium thiosulfate solution until all of the St. Claire, MN). After recovering the miscella, the bulk of color of the organic phase cleared. Each organic phase the solvent was evaporated, and the recovered oil was dried was then recovered, dried over anhydrous sodium sulfate, in an oven at 130 °C for 30 min. The oil was then stored in and evaporated to dryness under a stream of dry nitrogen. a desiccator until the sample reached room temperature, Preparations were then taken up in 1 mL of hexane for and the amount of oil was determined gravimetrically. chromatography. To measure iodine values, *2.0 g of ground kernel To prepare picolinyl esters, freshly extracted oil was sample was extracted with hexane at room temperature in a trans-esterified with 3-hydroxymethylpyridine under basic series of microcentrifuge tubes (*200 mg seed tissue and conditions as described by Destaillats and Angers [13]. 1 mL of hexane per tube). Chrome-steel beads (2.3 mm Crude oil (*10 mg) was recovered from each miscella by diam.) were added to the tubes, which were then ground in evaporating the hexane under a stream of dry nitrogen. Oils a Biospec Products (Bartlesville, OK, USA) microcentri- were then treated with 1 mL of anhydrous dichlorometh- fuge bead mill (90 % maximum speed) to macerate the ane, followed by 200 lL of 3-hydroxymethylpyridine and kernel matrix. The tubes were then centrifuged for 5 min at 100 lL of a 1.0 M solution of potassium tert-butoxide in *10,000g to pellet the debris, and the supernatant misc- tetrahydrofuran. The mixtures were allowed to react at ellas were combined in a single screw-cap test tube. Oil 40 °C for 30 min. After cooling, 1 mL of a 2.5 % sodium was recovered by evaporating the hexane under a stream of bicarbonate solution was added to each sample. The sam- dry nitrogen until the tube’s weight loss was negligible. ples were vortex mixed, and the aqueous and organic The process yielded *600 mg of crude oil for each sam- phases were allowed to separate. Each organic (lower) ple. Iodine values were determined by AOCS Official phase was recovered, dried with anhydrous sodium sulfate, Method Cd 1–25 [11]. Both yield and iodine analyses were and centrifuged to pellet the drying agent. The supernatants conducted in duplicate. were recovered for chromatography. 123 J Am Oil Chem Soc (2012) 89:1599–1609 1601 Gas Chromatography/Mass Spectrometry Determination of Fatty Acid Composition Most chromatography was conducted on a pair of Agilent The oils from ten individual seeds of T. populnea and ten 7890 gas chromatographs with split/splitless injectors and individual seeds of SG747 cottonseed were extracted and flame ionization detectors. One instrument was operated trans-methylated to form methyl esters. These were ana- with a Supelco SP-2380 capillary column (30 m 9 0.25 lyzed on both the SP-2380 and SP-2560 stationary phases.
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