Molecular species of triacylglycerols in the rubber particles of Parthenium argentatum and Hevea brasiliensis

Hathwaik, Upul; Lin, Jiann‐Tsyh; McMahan, Colleen

doi:10.1016/j.bcab.2018.07.019

Cited by 5 publications

(10 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In a recent valuable LC/MSMS study of triacylglycerols in rubber particles of H. brasiliensis , Hathwaik et al () detected fragment ions corresponding with the presence of 9M5 (e.g. labeled “308‐308‐308” with 308 u indicating 9M5) and, in the same fraction, also (fragment) ions which indicated the presence of a fatty acid with m/z 324, as “308‐308‐324”.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, it seemed more likely that both masses originated from two ions formed by the same molecule(s). Hathwaik et al () used the Lithium (Li) adduct technique for the analysis of triacylglycerols. Considering the difference of 16 u, it appeared plausible that the corresponding ion species shifted 16 u to higher mass originated from sodium (Na) adducts instead of the anticipated Li adducts.…”

Section: Resultsmentioning

confidence: 99%

“…Consequently, LC/MS ions in the Li adduct technique labeled “(9M5‐9M5‐324)Li + ” were rather “(9M5‐9M5‐9M5)Na + ” (Table S6). Likewise, Hathwaik et al () listed two triacylglycerols with the same composition at very different retention times when m/z 324 was detected (e.g., “9M5‐324‐S” at ~22.5 and ~32 min) which is impossible. Most likely, “324 u‐containing species" at earlier LC retention times originated from diacylglycerols and not triacylglycerols which eluted later (Table S6).…”

Section: Resultsmentioning

confidence: 99%

“…In H. brasiliensis , 9M5 is mainly bound to glycerols as triacylglycerol (Englert et al, ), and the existence of triacylglycerols with three 9M5 units (“tri‐9M5,” Fig. 1a) has been reported (Hasma and Subramaniam, ; Hathwaik et al, ; Liengprayoon et al, ). Detailed high performance liquid chromatography (HPLC) fractionation and analysis by liquid chromatography coupled with mass spectrometry (LC/MS) enabled the detection of 55 triacylglycerols and one diacylglycerol in the particle lipid extract of H. brasiliensis latex (Hathwaik et al, ).…”

Section: Introductionmentioning

confidence: 99%

“…Detailed high performance liquid chromatography (HPLC) fractionation and analysis by liquid chromatography coupled with mass spectrometry (LC/MS) enabled the detection of 55 triacylglycerols and one diacylglycerol in the particle lipid extract of H. brasiliensis latex (Hathwaik et al, ). Hathwaik et al () successfully gained low amounts of tri‐9M5 by means of HPLC.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Heart‐Cut Two‐Dimensional Countercurrent Chromatography for the Isolation of a Furan Fatty Acid Triacylglycerol from Latex Gloves and Identification of Further Lipid Compounds

Wiedmaier‐Czerny

Müller

Vetter

2020

J Americ Oil Chem Soc

View full text Add to dashboard Cite

Hevea brasiliensis latex from specific genotypes such as RRIM501 or PB235 is one of the richest natural sources of furan fatty acid 9-(3-methyl-5-pentylfuran-2-yl)nonanoic acid (9M5), which is mainly present in the form of triacylglycerols. In this study, we successfully isolated a triacylglycerol esterified with three 9M5 molecules (tri-9M5) with a purity of 97% from the lipid extract of latex gloves by means of countercurrent chromatography (CCC). The gas chromatography with a mass spectrometry (GC/MS) spectrum of tri-9M5 not only featured the diagnostic fragment ion [M-RCOO] + of triacylglycerols but also a fragment ion shifted by 16 Da to higher mass which corresponded with [M-RCO] + . [M-RCO] + was only detected in triacylglycerols substituted with at least one furan fatty acid. Additionally, five γ-tocotrienyl fatty acid esters (γ-T 3 -FA esters), namely, γ-T 3 -16:0, γ-T 3 -18:0, γ-T 3 -18:1n-9, γ-T 3 -18:2n-6 and γ-T 3 -20:0, were detected in the sample. Contributions of γ-T 3 -FA esters with 18:1n-9 and 18:2n-6 which co-eluted in GC/MS could be calculated after mathematical correction for contributions of the 13 C 2 isotope peak of γ-T 3 -18:2n-6 to γ-T 3 -18:1n-9. This was necessary for quantitation of these two γ-T 3 -FA esters. Improved separation of the γ-T 3 -FA esters could be achieved by the novel heart-cut recycling CCC mode (four cycles). Sterols detected in disposable latex gloves were β-sitosterol, Δ 5avenasterol, and stigmasterol along with small quantities of 24-methylene-cycloartenol and Δ 5 -citrostadienol.Keywords Triacylglycerol Á Countercurrent chromatography Á Hevea brasiliensis latex Á 9M5 Á Furan fatty acid Á Tocotrienyl fatty acid ester J Am Oil Chem Soc (2020) 97: 463-474. Fig. 1 (a) General structure of a triacylglycerol with R 1 , R 2 , and R 3 being acyl moieties and structure of (b) the characteristic GC/MS fragment ion [M-RCOO] + of triacylglycerols, (c) the [M-RCO] + fragment ion additionally found only in the presence of at least one furan fatty acid, and (d) the furan fatty acid 9M5. R 1,2,3 = fatty acid residue (one or more furan fatty acids). The structure with R 1, R 2, R 3 = 9M5 corresponds with tri-9M5 464J Am Oil Chem Soc J Am Oil Chem Soc (2020) 97: 463-474

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Heart‐Cut Two‐Dimensional Countercurrent Chromatography for the Isolation of a Furan Fatty Acid Triacylglycerol from Latex Gloves and Identification of Further Lipid Compounds

Wiedmaier‐Czerny

Müller

Vetter

2020

J Americ Oil Chem Soc

View full text Add to dashboard Cite

show abstract

Enrichment and structural assignment of geometric isomers of unsaturated furan fatty acids

Müller,

Conrad,

Hammerschick

et al. 2023

Anal Bioanal Chem

View full text Add to dashboard Cite

Furan fatty acids (FuFAs) are valuable minor fatty acids, which are known for their excellent radical scavenging properties. Typically, the furan moiety is embedded in an otherwise saturated carboxyalkyl chain. Occasionally, these classic FuFAs are accompanied by low amounts of unsaturated furan fatty acids (uFuFAs), which additionally feature one double bond in conjugation with the furan moiety. A recent study produced evidence for the occurrence of two pairs of E-/Z-uFuFA isomers structurally related to saturated uFuFAs. Here, we present a strategy that allowed such trace compounds to be enriched to a level suited for structure determination by NMR. Given the low amounts and the varied abundance ratio of the four uFuFA isomers, the isolation of individual compounds was not pursued. Instead, the entire isomer mixture was enriched to an amount and purity suitable for structure investigation with contemporary NMR methods. Specifically, lipid extracted from 150 g latex, the richest known source of FuFAs, was subsequently fractionated by countercurrent chromatography (CCC), silver ion, and silica gel column chromatography. Analysis of the resulting mixture of four uFuFAs isomers (2.4 mg in an abundance ratio of 56:23:11:9) by different NMR techniques including PSYCHE verified that the structures of the two most abundant isomers were E-9-(3-methyl-5-pentylfuran-2-yl)non-8-enoic acid and E-9-(3-methyl-5-pent-1-enylfuran-2-yl)nonanoic acid. Additionally, we introduced a computer-based method to generate an averaged chromatogram from freely selectable GC/MS runs of CCC fractions without the necessity of pooling aliquots. This method was found to be suitable to simplify subsequent enrichment steps. Graphical Abstract

show abstract

Biochemical composition of Hevea brasiliensis latex: A focus on the protein, lipid, carbohydrate and mineral contents

Bottier

2020

Advances in Botanical Research

View full text Add to dashboard Cite

Molecular species of triacylglycerols in the rubber particles of Parthenium argentatum and Hevea brasiliensis

Cited by 5 publications

References 29 publications

Heart‐Cut Two‐Dimensional Countercurrent Chromatography for the Isolation of a Furan Fatty Acid Triacylglycerol from Latex Gloves and Identification of Further Lipid Compounds

Heart‐Cut Two‐Dimensional Countercurrent Chromatography for the Isolation of a Furan Fatty Acid Triacylglycerol from Latex Gloves and Identification of Further Lipid Compounds

Enrichment and structural assignment of geometric isomers of unsaturated furan fatty acids

Biochemical composition of Hevea brasiliensis latex: A focus on the protein, lipid, carbohydrate and mineral contents

Contact Info

Product

Resources

About