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Cyclopropene Fatty Acids of Selected Seed Oils from Bombacaceae , Malvaceae, and Sterculiaceae

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Cyclopropene Fatty Acids of Selected Seed Oils from Bombacaceae , Malvaceae, and Sterculiaceae Reprinted from LIPIDS, Vol. 13, No.4, Pages: ~70-273 (1978) Cyclopropene Fatty Acids of Selected Seed Oils from Bombacaceae , Malvaceae, and Sterculiaceae M.B. BOHANNON and R. KLEIMAN, Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Peoria, Illinois 61604 ABSTRACT Fatty acid compositions of seed oils from three species of Bombacaceae, eleven from i\lalvaceae. and six from Sterculiaceae were determined. Each of the seed oils contains varying amounts of both malvalic and sterculic acids accompanied by one or both of the corresponding ;yclopropane fatty aCids. In addltlOn, the seed oil of Paclzira aqllaric Aub!. (Bombacaceae) contains 12.8% o:-hvdroxv- sterculic acid. INTRODUCTION treated with silver nitrate by the procedure of Schneider et al. (10) to convert the cyclo­ Cyclopropene fatty acids have been reported propene acids to derivatives amenable to chro­ as constituents in the seed oils from many matography. Epoxy acids, when present, were species of the Malvaceae, Sterculiaceae, Tilli;­ converted to methoxy-hydroxy derivatives by ceae, and Bombacaceae families (I). A number treating with boron trifluoride (II). Equivalent of oils from these families have been investi­ gated and found to contain both malvalic and chain lengths (ECL) of methyl esters and the sterculic acids, frequently accompanied by reaction products were determined by GLC as smaller proportions of one or both of the analo­ previously described (6). The normal methyl gous cyclopropane acids (2,3). In addition, seed esters were separated from the reaction prod­ oils containing malvalic acid usually contain ucts of the cyclopropene and hydroxy acids by measurable amounts of epoxy acids (4). thin layer chromatography (TLC) on l.()..mm It is evident from these earlier investigations layers of Silica Gel G developed with n-hexane­ that seed oils containing such an array o~f COm­ ethyl ether (70:30). The normal methyl esters pounds are difficult to quan titatively analyz were separated according to degree of unsatura­ by traditional gas liquid chromatography (GLC) tion on Silica Gel G (containing 20% silver and hydrogen bromide (HBr) titration proce­ nitrate) developed with benzene. Mass spectral dures. Recourt et al. (5) have shown that the data were obtained with a Dupont 21-491-2 c yc!opropene acids te~d to isomerize and m ass spectrometer interfaced to a Bendix decompose as they pass through the GLC Model 2600 gas chromatograph (GC-MS). The column. In addition. G LC data show that the column, 6 ft x Y, in. packed with 5% Silar (5 malvalic acid peak is masked bv the linoleic cp) was held isothermally at 195 C. acid peak (3) and that the corresponding cyclo­ Nuclear magnetic resonance (NMR) spectra propane acid may also be obscured by the were determined with a Varian HA-I 00 spectro­ presence of oleic acid (6). The HBr tit~ation meter. Samples were dissolved in deutero­ methods most often used to determine the chloroform; tetramethylsilane was used as an cyclopropene and epoxy acids present are internal standard. Infrared (IR) spectra were recognized as being su bject to interference by measured on liquid films with a Perkin-Elmer conjugated dienols (7). Model 337 spectrometer. A Beckman DK-2A The present investigation was undertaken to spectrophotometer was used to record ultra­ determine the fatty acid composition of a series violet (UV) spectra. Hydroxyl groups were of seed oils that contains a mixture of normal silylated with bis(trimethylsilyI)-trifluoro­ fatty acids and fatty acids with epoxy, acetamide in pyridine. h y d ro x y, cyclopropene, and cyclopropane functional groups. RESULTS AND DISCUSSION Preliminary Identification of Methyl Esters EXPERIMENTAL PROCEDURES and Derivatives Oil was obtained from the ground seed as GLC analyses of mixed methyl esters con­ previously described (8). Fatty ;cids in the oils taining only normal esters and derivatized reacting with hydrogen bromide at 55 C were cyc!opropene esters were consistent with the determined by the titration method of Harris et peaks previously reported for the esters from al. (9). Methyl esters for G LC were prepared by derivatized Sterculia foetida oil (10). However, sodium methoxide catalyzed methanolysis and G LC of those mixed esters also containing 270 TAIlLE I C'ollljlosilioll of S\,'L'd Oils J'-utly acid l'olllplJ~ilioll hy (:I.e (area %) ._-_.,.,-,._._~_.~-_.- C'yclo- Cyclo- Spectral data (lil ill !l_~!l~~!~::,_ ~!J.~~~,~_:__ HBr reactive ------ Sample seed (t)r;) 16:0 16: I 17:0 17: I 18:0 IH: I 18 2 20:0 20: I I H 19 IH 19 Epoxy:l Hydroxyh acids at sse «(XJ) uv lR /lomhI1CllCl'iH' Chot/sia St. lIiL 21.7 I H.7 0,5 0.2 0.2 2.R II.'I 4'1.7 0.7 (), I 0.5 12.4 10.0 O.H 21.0 Pllcllirll a(fuaticll Alibi 55,5 bO.S 0.3 2.9 7.6 4.7 0.'1 0.1 1.6 8.6 J 2.8 26.6 011 .\'almaJiIl mil/aharicll (DC') SdlOll and End!. 23,6 .lO.O 0.6 0.2 O.H 5.0 16,7 25.0 Ir 0.6 7.5 11.0 1.0 15.5 L3" 1.0 () >-<: A1£1JI'1l/'CI1C () t-< A It!locullin'/{ 1a L. 12.2 1.1.0 0.5 0.3 0.'1 4.'1 7.5 52.8 O.H 0.'1 0.2 16.5 1.6 22.4 ... 0 /lilli,w'l/.\' gramJij1oru,\J.I I 1.7 I H.2 0.4 2.0 6.0 15.5 46.0 0 . .1 O.H 1..1 4.0 .1.0 1.6 7.2 ... OB "tJ l1ihisCII,\' syril1£'II,Vd 27.7 20.0 Ir Ir 0.7 2.2 10.2 42.6 0 . .1 Ir 1.0 1J.4 3.0 2.7 2.B 19.9 ... all :>:l K itaiht'lia vitifolia 0 "tJ Will" 22.6 H.O 0.3 Ir 0.3 2.5 14.2 64.4 0.5 0.2 0.1 7.7 1.5 10.5 OB tTl I.agullarfa pater,WHlff Z C;. DOll I H.t) 23.0 .1.9 Ir 0.4 4.7 21.5 22.3 Ir I.t 7.7 3.9 1.4 14.1 ... OB tTl llva/era kas1lmirfanll 'Tj Comh. 19.1 15.0 Ir Ir 0,6 .1.6 10.H 50.5 0.5 0 . .1 0.5 Ir 16.4 1.2 ... -.. 14.4 ... > iHlllvl111/0nfatW Forsk 18.4 15.7 0.2 Ir 0.4 .1 ..1 10.3 55.5 Ir 0.2 12. I 1.0 ... 1.0 14.4 ... ... >-J ... ... >-J Malva parviJlora L. 11.0 15.4 0.2 1.1 .1.0 9.0 5.1.'1 O.B 0.2 0.4 12.0 1.7 1.0 1.2 14.8 --< Malva 100UIU'fOl'tiIl1l11 L. 17.0 12.4 0.5 1.6 2.1 .1.5 11.0 4.1.B 2.3 0.2 Ir 0.3 17.H 1.5 2.0 '" 23.7 ... ... Ala/ope {rlfltIa 11axl. 18.0 0.3 .1.7 6.8 17.7 0.2 1.6 44.3 0.2 0.2 0 . .1 11.5 3.1 6.5 1.2 24.9 L2" 5.4 OH ()> PUl'fJ1lil1 sf'plufll SI. Ilil 26.6 .11.0 1.0 Ir D.2 2.0 1SA 34.2 0.5 Ir Ir Ir 2.3 1.3 5.1 5.7 17.6 L2 3.6 OH a (fJ S'!erculit1ct'(U' Ffrmitlllll pldtallifo1itl Schott and End!. 24.3 17.2 1.2 Ir 0.2 2.4 18.2 36.0 0.7 Ir 0 ..1 1.6 20.5 2.0 '" 24.3 Ptt'rygolll a/aId Hoxh, 47.H 24.4 1.6 0.2 0.3 .1.:1 9.9 .18.5 0.6 0.1 0.6 12.2 2.5 2.7 1.4 19.5 ... OB Pterospermlllll (leerifoliulJI (L.)lVilid 21.5 17.0 Ir Ir 0 . .1 2.9 8.6 .12.3 1.0 .12.2 3.8 ... ... 39.1 •\'U'J'clilia ftH.'tida L. 5.1.5 14.7 Ir Ir Ir 1.4 4.9 4.5 I.B 0.2 Ir 0.4 6.3 65.1 ... ... 64.6 'J'llrric{iulifiliJI..1 29.7 29.2 0.7 0.1 0.2 2,0 20..1 0.6 Ir 0.2 6,8 ... ... t-< 18.9 Ir 20.2 25.7 ~ UEpoxy acid is verl1IJlic hy GLC evidcllce. t:! h'-Iydroxy add is a conjugated dicilol hy GLC' L'vidt~I1CC except ill P. aqllatic(J andH. syriaclJs which Wt~re identified as a-hydroxystcrculic. •(fJ <: q-:l conjugaled (dene; % in falty acids. 0 tlAHthorilY no! available. r q~2 conjugated dicne; % ill fatty acids. ~- Z l~ 9 --..I -I> 272 M.B. BOHANNON AND R. KLEIMAN epoxy, hydroxy, or conjugated unsaturation from the isolated component were not as were difficult to interpret. Esters shown to con­ clearly defined. However, the appropriate mole­ tain the epoxy function were further deriva­ cular ions at m/e = 412 for the ketone deriva­ tized by converting this group to the methoxy­ tive and m/e = 428 for the methoxy derivative hydroxy derivative followed by conversion of were apparent. Also, the ion at m/e = 161 re­ the hydroxyl group to the trimethylsiloxy sulting from cleavage alpha to the carbon (TMS) ether (11). The resulting TMS-deriva­ bearing the TMS group was observed. tized esters were reanalyzed by GLC.
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