Analysis of conjugated octadecatrienoic acids inmomordica balsamina seed oil by GLC and¹³C NMR Spectroscopy

Abstract

Separation of conjugated octadecatrienoic acids by open tubular gas liquid chromatography (GLC) was performed using glass capillary columns coated with Carbowax 20 M and with OV‐1. The equivalent chain length of geometrical isomers of the conjugated octadecatrienoic acids belonging to the two series C18:3Δ8.10.12 and C18:3Δ9.11.13 were determined. The application of these results to the study of theMomordica balsamina seed oil shows that this oil contains two conjugated octadecatrienoic fatty acids in appreciable amounts, punicic acid (50%) and α‐eleostearic acid (13%). The isomerization of conjugated acids inM. balsamina seed oil was followed for one year. Quantitation of octadecatrienoic acids using GLC gave results similar to those obtained with13C NMR.

Screening analysis of unknown seed oils

“…BPX-70 TM ∆5-unsaturated polymethylene-interrupted fatty acids in Ranunculaceae [120]; γ-linolenic, α-linolenic, and stearidonic acid in Boraginaceae [121]; acetylenic fatty acids in Olacaceae [11] Carbowax 20M TM /DB Wax TM Conjugated triene fatty acids in Cucurbitaceae [90], positional monoene isomers in Sapindaceae [2,122], ∆5-unsaturated polymethylene-interrupted fatty acids in Cupressaceae, Pinaceae, and Taxaceae [123] CP-SIL-88 TM Unusual unsaturated double bond and configuration isomers in Ranunculaceae [124] and Pinaceae [125] CP-WAX 52CB TM Methyl-branched and ∆5-unsaturated polymethylene-interrupted fatty acids in Ginkgo biloba [20] DB-23 TM Cyclopropanoic, cyclopropenoic, and hydroxy fatty acids in Bombacaceae [14], positional monoene isomers in Sapindaceae [2,122], conjugated triene, tetraene, and keto fatty acids in Chrysobalanaceae [21,77,126] and Euphorbiaceae [6], acetylenic acids in Olacaceae [3,128] and Santalaceae [3,128] SILAR 5 CP TM ∆5-unsaturated polymethylene-interrupted fatty acids in Ranunculaceae [129], allenic fatty acids [13] SP2330 TM Polyunsaturated fatty acids in various species [130] Detection of the individual compounds can be made with a flame-ionization detector (FID).…”

“…for acetylenes [84][85][86][87], allenes [15,69], conjugated acetylenes [10], conjugated dienes [5,85,88], trienes [89][90][91][92], tetraenes [8,91,93], conjugated olefin-acetylenes [3,11,72], cyclopropenes [14,83], epoxy [94], hydroxy [14,95,96], keto [95,97], and olefins (monoenes [84,85,87,98]; polyenes, methyleneinterrupted [99][100][101][102]; non-methylene-interrupted [98,103,104]). …”

High‐resolution nuclear magnetic resonance spectroscopy —Applications to fatty acids and triacylglycerols

“…Cherry seed oil, from the Rosaceae family, contains about 10% of α-eleostearic acid, 18:3(9c,11t,13t), which was characterized by 1 H-and 13 C NMR spectral analysis (92).The seed oil of Momordica balsamina contains high levels of punicic acid, 18:3(9c,11t,13c) (50%), and α-eleostearic acid, 18:3(9c,11t,13t) (13%). The structure and the quantities of these conjugated fatty acids in the oil were determined by a combination of gas-liquid chromatographic and 13 C NMR analyses (93). Tulloch (94) studied the spectra of seven seed oils (Punica granatum, Cucurbita palmata, Jacaranda mimosifolia, Centranthus ruber, Catalpa bignonioides, Chilopsis linearis, and Calendula officinalis) and identified six C 18 isomeric conjugated trienes by this technique.…”

Sources and Bioactive Properties of Conjugated Dietary Fatty Acids

“…This may be in part due to the prevalence of these isomers within certain seed oils, etc. (Table 1) [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34], but also due to the extensive range of bioactivities associated with these isomers. Indeed, isomers of CLNA have been associated with anti-adipogenic and anti-carcinogenic properties, along with the modulation of immune function and inflammatory response [13,35].…”

“…Similar to pomegranate seed oil, bitter gourd seed oil and its primary CLNA isomer, known as α-eleostearic acid (c9, t11, t13), have both exhibited anti-carcinogenic properties in studies conducted using colonic (HT-29, Caco-2), mammary (MDA-wt, MDA-ER α7, MCF-7), and human leukemia cells (HL60) [64][65][66][67][68]. In these in vitro studies, exposure to α-eleostearic acid has been associated with increased cellular lipid peroxidation, inhibition of DNA synthesis, Fevillea trilobata oil 30 [17] Momordica balsamina seed oil 50 [18,19] Snake gourd seed oil 40 [20,21] Ecballium elaterium seed oil 22 [20] Milk fat ≤0.03 [22] Canadian milk fat Rapeseed oil 2.50 [23] GMO rapeseed c9, t11,t13 Tung seed oil 67.7 [16] Bitter gourd seed oil 56.2 [16] Snake gourd seed oil 30-50 [24] White mahlab 38.32 [25] Parwal seed oil 30-50 [24] Sugihiratake mushroom NS [26] Edible Japanese mushroom Parinarium species seed oil 22-69 [27,28] Prunus yedoensis seed oil 35 [28] Chrysobalanus icaco seed oil 22 [27] t9, t11, c13 Catalpa seed oil 42.3 [16] t9, t11, t13 Chemosynthesized >97 [29] Larodan Fine Chemicals, Sweden c8, t10, c12 Jacaranda seed oil 31 [30] t8, t10, c12 Pot marigold seed oil 50-62 [16] t8, t10, t12 Pot marigold seed oil 4.7 [31] c9, t11, c15 Lactobacillus plantarum AKU 1009a 67 [32] 6,9,11,15 Strains of Bifidobacterium breve 9-26 [ Chrysobalanus icaco seed oil 10 [27] Sebastiania brasiliensis seed oil 39 [44] Impatiens edgeworthii seed oil 48…”