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New Sources of 9-D-Hydroxy-Cis-12-Octadecenoic Acid 1

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New Sources of 9-D-Hydroxy-Cis-12-Octadecenoic Acid 1 Reprinted from LIPIDS, November, 1969, Vol. 4, No.6, Pages: 450-453 New Sources of 9-D-Hydroxy-cis-12-octadecenoic Acid 1 R. G. POWELL, R. KLEIMAN and C. R. SMITH, JR., Northern Regional Research Laboratory,2 Peoria, Illinois 61604 ABSTRACT gl V cerid e mixt ure isolated from Nerium ;l~ander L. seed oil. 9-D -Hydroxy-cis-12-octadecenoic acid has been isolated from 3 seed oils of the family Apocynaceae: Holarrhena anti­ PROCEDURES AND DATA dysenterica (73%), Nerium oleander Infrared (IR) spectra were determined on a (II %) and Nerium indicum (8%). The Perkin-Elmer 137 instrument as liquid films or known occurrence of this acid was as I % solutions in carbon tetrachloride or car­ previously limited to the genus bon disulfide. Nuclear magnetic resonance Strophanthus (9-15%). A mixture of (NMR) spectra were recorded on Varian A-60 unusual tetra-acid glycerides was isolated or HA-IOO spectrometers with deuteriochloro­ from N. oleander oil by thin layer chro­ form solutions containing 1% tetramethylsilane matography. Pancreatic lipase hydrolysis as an internal standard (unless otherwise indi­ of the glyceride mixture showed that cated). Optical rotatory dispersion (ORO) 9 -D-acetoxy-cis-12-octadecenoic acid is measurements were made on a Cary Model 60 esterified exclusively at an Cl'-glycerol recording spectropolarimeter at 26° in absolute position and that normal fatty acids methanol and in 0.5 dm cells. Melting points occupy the remaining 2 glycerol posi­ were determined with a Fisher-Johns melting tions. A portion of the hydroxy acid in point apparatus and are uncorrected.. N. indicum oil was also acetylated, how­ Thin layer chromatography (TLC) was per­ ever. no acetate was found in either H. formed on plates coated with 0.25 mm or 1.0 antidysenterica or Strophanthus hispidus mm layers of Silica Gel G or 20% silver nitrate­ oils. impregnated Silica Gel G with 20% or 30% ether in hexane as the solvent. Bonc ac!d­ INTRODUCTION impregnated plates were used for analysis of lipolysis products. Spots on analytical plates Gunstone (1) first reported the occurrence were visualized by charring with sulfuric acid­ of 9-hydroxy-cis-12-octadecenoic acid in chromic acid. After preparative plates were Strophanthus sarmentosus seed oil and later sprayed with dichlorofluorescein, bands were showed that it probably is of general occur­ visualized under ultraviolet light. rence (9-15%) in seed oils of the genus Gas liquid chromatography (GLC) of methyl Strophanthus, family Apocynaceae (2). The esters was conducted as described by Miwa et structure has been confirmed by synthesis (3) al. (7). Triglycerides were analyzed on an F &M a nd the naturally occurring "Strophanthus Model 5750 instrument equipped with a 24 X acid" has been assigned the D configuration (4). 1/8 in. metal column packed with 3% OV-l. The Strophanthus acid may also be obtained by The instrument was linearly temperature-pro­ partial diimide reduction of naturally occ~rring grammed at 4 deg/min from 200-400 C. 9 -D-h y d r 0 xy t ra m-I O,cis-I 2-octadecad!enOlC Oxidative cleavages were according to the acid (5,6). method of von Rudloff (8). Iodine values were Strophanthus oils are convenient sources of determined by the AOCS method (9). Pan­ min or amounts of 9-D -hydroxy-cis-12-octa­ creatic lipase hydrolyses, silylations and subse­ decenoic acid. however. the low hydroxy acid quent GLC of silylated lipolysis products were content and u'navailability of the oils suggested as described by Tallent and Kleiman (10). a search for additional sources among the closely related genera Holarrhena and Nerium. Isolation and Purification of Hydroxy Acids In tltis paper we report the characterization Seeds were ground and extracted overnight of 9-D-hydroxy-cis-12-octadecenoic acid from 3 in a Soxhlet apparatus with petroleum ether new sources. One, Holarrhena antidysenterica (30-60 C); solvent was removed from the oils (Roth) Wall ex. DC. seed oil, contains this acid on a rotary evaporator. Both Nerium oleander as the major component (73%). We also report and Naium indicum oils exhibited bands in the the characterization of an unusual tetra-acid IR at 1235 cm-! and 1020 cm-! (acetate) which were not present in spectra of H. anti­ ! Presented at the AOCS Meeting, San Francisco, dvsenterica or Strophanthus hispidus oils. April, 1969. Methyl esters were prepared by refluxing the 2No. Utiliz. Res. Dev. Div., ARS, USDA. oils for 2 hr with 5% hydrochloric acid in [I] 9-HYOROXY-CIS-OCTAOECENOIC ACID anhydrous methanol. Esters were recovered by ...'" <r. >0 ~ N N ".; ei ether extraction and were analyzed by GLC. Oil is yield:>, iodine values and analyses of the methyl esters by GLC are recorded in Table 1. Concentrates of the hydroxy esters were ob­ >, ,..., tained by preparative TLC. The concentrates ~ '" ~ >0 U 2 - ,..., r-: were saponified by refluxing for 1 hr with 1N "'0 0 t"- o -l >,-" t"- potassium hydroxide in ethanol, and unsaponi­ v :: - >, fiables were removed by extracting dilute ,:;;; aqueous solutions of the soaps with ether. After .s'"en acidification, the free hydroxy acids were ,..., ,..., "": N recovered by ether extraction. The acids were '"~ - " - 0 0 esterified with diazomethane, and the resulting '""'" - esters were purified by preparative TLC. Overall 2 .5 yields were near 80% in each instance (based on N ~ r-: GLC of the total esters). "t"- t"- .d-.'" ~ "- <t <r. N Characterization of Hydroxy Acids ~ '" Hydroxy acid methyl esters from the 4 oils >, r-: c: 0 (H. antidysenterica, N. oleander, N. illdicum, t"- -<i" N ,...,:xi '" " N N and S. hispidus) were indistinguishable by IR ::g ...E and NMR. The spectra were consistent with a 0 0 "'0 C1 8 methyl ester having 1 hydroxyl and 1 cis = '" 0 >0 CIl'" :~ r-: r-: - double bond. GLC of the esters gave single N <t <r. :xi peaks, > 98%, for each and retention character­ '" 0 " '"<.>" "'" istics of all 4 esters were identical. The esters ~ g >, U showed single spots which were not differen­ <.> 0 OO tiated by TLC on either ordinary or silver­ ~ i nitrate impregnated plates. J "'0 Samples of hydroxy ester from each of the 4 :0 ~ «: <.> oils were cleaved oxidatively and methyl esters -;'" o of the products were prepared by refluxing ""' CIl with acidic methanol. The IR spectrum of each ~ oxidation product had a strong band at 1773 .8 cm- l characteristic of a 'Y-lactone, and GLC 8 ::; showed methyl hexanoate and a fragment cor­ .: responding to a C 'Y-lactone-methyl ester (5). ~ l2 E- .:: Thus, the hydroxy acids from all 4 sources are ~" ~ Cl8 acids having hydroxyl at C9 and a cis ~ double bond at C1 2. ORD curves were also ob­ :; tained for each of the 4 methyl ester samples .£ (Table II). Hydrogenation of the hydroxy ester from H. antidysenterica, with palladium-charcoal in hexane, gave methyl 9-hydroxyoctadecanoate. t""-~-oo ~~I.CiM After preparative TLC and recrystallization M~('.ll""'l from hexane, the saturated ester melted at 51-52 C and had a plain negative ORD curve (Table II). Known methyl 9-o-hydroxyocta­ decanoate gives a similar melting point, 51.5-52.8 C, and a nearly superimposable plain negative ORD curve (11). A 156 mg portion of methyl 9-hydroxy-cis­ 12-octadecenoate, from Holarrhena oil, was acetylated by allowing to stand overnight in a mixture of pyridine-acetic anhydride (1: I). Column chromatography on 2 g of neutral alumina (hexane) yielded 176 mg of product. The product gave IR and NMR spectra which [2 ] R. G. POWELL, R. KLEIMAN AND C. R. SMITH, JR. TABLE II Optical Rotatory Dispersion of Hydroxy Esters Specific rotation in degrees Concentration, Ester and source [a] 589 [a1500 [a]400 g/100 ml Methyl 9-0-hydroxy-cis-12-octadecenoate Holarrhena antidysenterica -0.83 -1.18 -2.00 2.88 Nerium oleander -1.76 -2.30 -3.20 1.13 Nerium indicum -1.92 -2.34 -3.40 0.95 Strophan thus lzispidus -1.87 -2.48 -4.12 2.67 Strophanthus kombea -1.17 -1.76 -2.54 1.02 Methyl 9-0-hydroxyoctadecanoate Hydrogenated Holan-hena ester -0.12 -0.16 -0.30 2.29 Hydrogenated methyl dimorphecolatea -0.17 -0.23 -0.37 1.49 aSpecific rotations of these materials were obtained by Applewhite et aJ. (11) and are listed here for comparison. were consistent with those expected for methyl free carboxylic acid, but also had bands at 1724 9-acetoxY-cis-12-octadecenoate. GLC and TLC cm-1 and 1235 cm- l , characteristic of an showed the product to be homogeneous. acetoxy derivative. Treatment with diazo­ methane gave the methyl ester which was iden­ Glyceride Characterization tical with known methyl 9-acetoxY-cis-12-octa­ An unknown component was observed upon decenoate, as demonstrated by IR, NMR, GLC TLC analysis of N. oleander oil, which had an and TLC. Rf slightly lower than normal triglycerides. A portion of lipolysate of the unusual GLC of the oil indicated that acetotriglycerides glyceride mixture was silylated, and GLC and triterpene acetates were absent because no showed no monoglycerides with acetoxy func­ significant components with carbon numbers tional groups. Similar treatment of a lipolysate less than C52 were observed. A significant peak of the original oil showed that 5% of the mono­ was eluted as Cs 6, however, even though only glycerides contained acyl groups with hydroxy 2% C20 esters were found in the ester analysis. or acetoxy functions, or both. A portion of the The presence of glycerides containing an whole oil lipolysate was treated with diazo­ acetylated hydroxy acid constituent was indi­ methane and subsequent GLC demonstrated 1 cated by a conspicuous 1235 cm- (acetate) that 12% acetoxy and 2% hydroxy methyl band in the IR; only weak hydroxyl absorption esters were present in the mixture.
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