Process for the Purification of cis-p-Coumaric Acid by Cellulose Column Chromatography after the Treatment of the trans Isomer with Ultraviolet Irradiation

Mitani, Takahiko; Mimura, Hisa; Ikeda, Keiko; Nishide, Mitsunori; Yamaguchi, Masanori; Koyama, Hajime; Hayashi, Yukinori; Sakamoto, Hidefumi

doi:10.2116/analsci.18p102

Cited by 11 publications

(12 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The different derivatives detected may correspond to cis and trans stereoisomers like those identified in apple peels ( He and Liu, 2007 ; McGhie et al , 2012 ). This hypothesis is supported by the slight difference in the λ max of the compounds, and 308 nm could be indicative of cis isomers whereas 310/311 nm could correspond to trans isomers ( Mitani et al , 2018 ). The last compound of the group (13), showing a λ max at 322 nm, appeared to be a feruloyl derivative of hydroxy-ursolic or -oleanolic acid.…”

Section: Resultsmentioning

confidence: 88%

Cuticular waxes of nectarines during fruit development in relation to surface conductance and susceptibility to Monilinia laxa

Lino

Quilot-Turion

Dufour

et al. 2020

Journal of Experimental Botany

View full text Add to dashboard Cite

Abstract The cuticle is composed of cutin and cuticular waxes, and it is the first protective barrier to abiotic and biotic stresses in fruit. In this study, we analysed the composition of and changes in cuticular waxes during fruit development in nectarine (Prunus persica L. Batsch) cultivars, in parallel with their conductance and their susceptibility to Monilinia laxa. The nectarine waxes were composed of triterpenoids, mostly ursolic and oleanolic acids, phytosterols, and very-long-chain aliphatics. In addition, we detected phenolic compounds that were esterified with sugars or with triterpenoids, which are newly described in cuticular waxes. We quantified 42 compounds and found that they changed markedly during fruit development, with an intense accumulation of triterpenoids during initial fruit growth followed by their decrease at the end of endocarp lignification and a final increase in very-long-chain alkanes and hydroxylated triterpenoids until maturity. The surface conductance and susceptibility to Monilinia decreased sharply at the beginning of endocarp lignification, suggesting that triterpenoid deposition could play a major role in regulating fruit permeability and susceptibility to brown rot. Our results provide new insights into the composition of cuticular waxes of nectarines and their changes during fruit development, opening new avenues of research to explore brown rot resistance factors in stone fruit.

show abstract

Section: Resultsmentioning

confidence: 88%

Cuticular waxes of nectarines during fruit development in relation to surface conductance and susceptibility to Monilinia laxa

Lino

Quilot-Turion

Dufour

et al. 2020

Journal of Experimental Botany

View full text Add to dashboard Cite

show abstract

“…Isomerization also occurred in the absence of laccase and has been reported more often upon exposure of pCA derivatives to light. 30,31 Moreover, in contrast to VBG, VBG-pCA was readily oxidized by laccase alone with 39% and 82% substrate conversion after 1 and 24 h, respectively (Figure 2B, Tables 1 and 2). This conversion resulted in formation of multiple products with molecular formula C 54 H 54 O 16 , which were annotated as VBG-pCA dimers.…”

Section: ■ Results and Discussionmentioning

confidence: 97%

Reactivity ofp-Coumaroyl Groups in Lignin upon Laccase and Laccase/HBT Treatments

Hilgers

Kabel

Vincken

2020

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Laccase–mediator systems (LMS) are potential green tools for oxidative degradation and modification of lignin. Although LMS convert both phenolic and nonphenolic lignin structures, phenolic structures are more prone to react. Remarkably, in a previous study on laccase/HBT treatment of grasses, we observed the accumulation of p-coumaroyl moieties in residual lignin, even though such groups are free phenolic structures. To provide more insights into this apparent paradox, here, we studied the reactivity of p-coumaroyl groups in lignin and model compounds using HSQC NMR and RP-UHPLC-PDA-MSn, respectively. It was found that a p-coumaroylated model compound (VBG-pCA), in contrast to its nonacylated analogue, was rapidly converted by laccase and laccase/HBT, resulting in oxidative coupling and HBT-mediated degradation, respectively. The high reactivity of VBG-pCA was related to the phenolic character of the p-coumaroyl group. Upon laccase/HBT treatment of two grass lignin isolates, p-coumaroyl groups accumulated in residual lignin, indicating that p-coumaroyl groups in polymeric lignin display different reactivity than those in model compounds. On the basis of additional experiments, we propose that p-coumaroyl groups in lignin polymers can be oxidized by laccase/HBT but undergo HSQC-undetectable radical coupling or redox reactions rather than degradation.

show abstract

“…N , O ‐Bis(trimethysilyl)trifluoroacetamide (BSTFA) and unlabelled trans ‐ferulic and trans ‐ p ‐coumaric acids were purchased from Sigma‐Aldrich (Lyon, France). cis ‐Ferulic and cis‐p‐ coumaric acids were produced by sunlight irradiation of the trans isomers in methanol 14 . Fully 13 C‐labelled trans ‐ferulic and trans ‐ p ‐coumaric acids were isolated (97% 13 C) from leaves of 13 C‐labelled Avena sativa obtained from IsoLife (Wageningen, The Netherlands).…”

Section: Methodsmentioning

confidence: 99%

“…cis-Ferulic and cis-p-coumaric acids were produced by sunlight irradiation of the trans isomers in methanol. 14 Fully 13 Clabelled trans-ferulic and trans-p-coumaric acids were isolated (97% 13 C) from leaves of 13 C-labelled Avena sativa obtained from IsoLife (Wageningen, The Netherlands). This isolation involved alkaline hydrolysis of leaf debris and purification of the resulting total lipid extract by preparative thin layer chromatography (TLC) on silica gel K6 plates (Whatman, Maidstone, UK) after elution with CHCl 3 / CH 3 OH/HCOOH (85:15:1, v/v/v).…”

Section: Chemicalsmentioning

confidence: 99%

Electron ionization mass spectrometric fragmentation and multiple reaction monitoring quantification of ferulic and p‐coumaric acid trimethylsilyl derivatives in deposited atmospheric particles

Rontani

Charrìère

Aubert

et al. 2022

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Rationale: Ferulic and p-coumaric acids are important biological and structural components of plant cell walls and possess antioxidant and antimicrobial properties.These phenolic acids are widespread in environmental samples. However, when they are present at very low concentrations or in very complex lipid extracts, their identification and quantification can be challenging. Methods:The electron ionization mass spectrometry (EI-MS) fragmentation pathways of ferulic and p-coumaric acid trimethylsilyl (TMS) derivatives were investigated. These pathways were deduced by (i) low-energy collision-induced dissociation (CID) gas chromatography (GC)/EI-MS/MS, (ii) accurate mass measurement, and (iii) 13 C labelling. These compounds were then characterized and quantified in multiple reaction monitoring (MRM) mode in total lipid extracts of deposited atmospheric particles using highly specific transitions based on the main fragmentation pathways elucidated.Results: Low-energy CID-MS/MS analyses, accurate mass measurement and 13 C labelling enabled us to elucidate EI-MS fragmentations of ferulic and p-coumaric acid TMS derivatives. Some specific fragmentations proved useful for subsequent characterization and quantification of these compounds. As an application of some of the described fragmentations, trace amounts of these phenolic acids were characterized and quantified in MRM mode in wet-and dry-deposited atmospheric particles containing low proportions of organic matter.Conclusions: EI-MS fragmentations of ferulic and p-coumaric acid TMS derivatives exhibit specific fragment ions that can be very useful for the quantification of trace amounts of both phenolic acids in environmental samples.

show abstract

Process for the Purification of cis-p-Coumaric Acid by Cellulose Column Chromatography after the Treatment of the trans Isomer with Ultraviolet Irradiation

Cited by 11 publications

References 8 publications

Cuticular waxes of nectarines during fruit development in relation to surface conductance and susceptibility to Monilinia laxa

Cuticular waxes of nectarines during fruit development in relation to surface conductance and susceptibility to Monilinia laxa

Reactivity ofp-Coumaroyl Groups in Lignin upon Laccase and Laccase/HBT Treatments

Electron ionization mass spectrometric fragmentation and multiple reaction monitoring quantification of ferulic and p‐coumaric acid trimethylsilyl derivatives in deposited atmospheric particles

Contact Info

Product

Resources

About