GLC‐MS analysis of the fatty acids of the seed oil, triglycerides, and cyanolipid of Paulliania elegans (Sapindaceae) – a rich source of cis‐13‐eicosenoic acid (paullinic acid)

Abstract

SummaryThe fatty acids of the total lipids, triglycerides, and the cyanolipid of PauZZinia elegans (Sapindaceae) have been analyzed as their methyl esters and 4,4-dimethyloxazoline derivatives by gas chromatography-mass spectrometry. It was shown that the gas chromatographic separation of the oxazoline derivatives was sufficient to ensure the correct identification of the monoenic fatty acid positional isomers. Stereochemistry of the double bonds has been confirmed by infrared and 13C-nuclear magnetic resonance (NMR) spectroscopy. cis-13-Eicosenoic Acid (Paullinic acid) (44.4%) and cis-11-octadecenoic acid (cis-vaccenic acid) (19.8%) were found to be the main components beside other monoenoic acid positional isomers. The cyanolipid of P. eleguns was identified as 2,4-dihydroxy-3-methylenebutyronitrile derivative by IR, 'H-NMR, 13C-NMR spectroscopy and was quantified by 'H-NMR spectroscopy (71.4%).

Screening analysis of unknown seed oils

“…ref. [2,3,10,14,16,21,23,77,120,122,126,129,180,187,206] for 4,4-dimethyloxazoline derivatives and ref. [20,185,186,196,207] for picolinyl ester derivatives.…”

“…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).…”

“…The detection of acetolipids [83], allene estolides [15], cyanolipids I-IV [2,105,106], and free fatty acids [83] is also possible by 13 C NMR spectroscopy. In an Apocynaceae seed oil, even the detection and identification of two apolar alkaloids was possible through analyzing the 13 C NMR data of the lipid mixture [57].…”

Bioactive Natural Products from Sapindaceae Deterrent and Toxic Metabolites Against Insects

“…Eicosanoic acid (20:0) and eicosenoic acid (20:1 n-9) are present in high proportion in many species (Aichholz et al 1997). In the genus Paullinia, the rare fatty acids paullinic acid (Z-13-eicosenoic acid) and cis-vaccenic acid (Z-11-octadecenoic acid) are ubiquitous constituents (Seigler 1974;Spitzer 1995;Spitzer 1996;Lago et al 2000;Avato et al 2003). Other fatty acids found go from dodecanoic (12:0) to docosanoic acids (22:0) (Mikolajczak et al 1970a;1970b;1971;Aichholz et al 1997;Avato et al 2003).…”

Free radical scavenging and anti-edematogenic activities of Paullinia elegans Cambess., Sapindaceae, leaves extracts

“…In Brazil, this species is known as "cipó-timbó". Chemical studies of the seeds of Paullinia elegans describe the isolation of cis-13-eicosenoic acid, cis-11-octadecenoic acid and 2,4-dihydroxy-3-methylenebutyronitrile (Spitzer, 1995(Spitzer, , 1996. Species of the genus are known to contain fatty acids (Spitzer, 1996), and purin alkaloids (Weckerle et al, 2003) as major constituents.…”