Feruloyl Derivatives Research Articles

Metabolomics and molecular networking approaches reveal differential metabolites of Radix Scrophulariae from different geographical origins: Correlations with climatic factors and biochemical compounds in soil

Radix Scrophulariae (RS) is a well-known and frequently used traditional Chinese medicine. Cultivated RS from Zhejiang province is considered to be superior in quality to that from other provinces in China. However, the contribution of geographical origins to differential metabolite production in RS is unclear. In this study, we used ultrahigh-performance liquid chromatography-quadrupole-orbitrap mass spectrometry-based metabolomics and molecular networking to examine differential metabolites in RS samples from different origins and explore their correlations with climatic factors and biochemical compounds in soil. nineteen compounds were identified as the important differential metabolites in RS from different origins, including two oligosaccharides, six cinnamoyl derivatives, four p-coumaroyl derivatives, three caffeoyl derivatives, two feruloyl derivatives, and three methoxycinnamoyl derivatives. However, harpagide and harpagoside, two chemical markers in Chinese Pharmacopoeia, were not among the differential metabolites. Moreover, 18 compounds having higher contents in RS from Zhejiang than in that from other provinces, emerged as candidate chemical markers of quality control. The contents of differential metabolites were negatively correlated with humidity and precipitation in October and positively correlated with evaporation and surface temperature. This study provides a foundation for further research on the quality control, pharmacological activity, and product development of RS from Zhejiang and a useful strategy for further optimizing the cultivation process of RS.

Comparative UHPLC-HRMS Profiling, Toxicological Assessment, and Protection Against H2O2-Induced Genotoxicity of Different Parts of Opuntia ficus indica.

Opuntia ficus indica has been an important dietary source and a traditionally used medicinal plant. Given the promising health-promoting properties of this plant, a comparative toxicological assessment and antioxidant bioevaluation of extracts from different parts of the plant were carried out in relation to their chemical profile. Toxicity was examined at multiple endpoints using the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT), Comet and the γH2AX In-Cell Western Assay, while hyphenated ultra-high-performance liquid chromatography-high-resolution mass spectrometry (UHPLC-HRMS) analysis was carried out to identify main constituents. None of the extracts showed any cytotoxic and genotoxic effect on cell lines used, apart from the flower extract in HepG2 cells at the highest concentration tested (2.5 mg/mL). Both fruit flesh and seed extracts demonstrated a prominent protective effect against H2O2-induced genotoxicity in almost all concentrations tested, while extracts originated from flowers and cladodes were effective only at the low non-cytotoxic (0.312 and 0.625 mg/mL) and high (1.25 and 2.5 mg/mL) concentrations, respectively. In total, 2 phenolic acids, 12 flavonoids, along with 3 feruloyl derivatives and the plant pigment indicaxanthin, were tentatively identified by UHPLC-HRMS analysis. Phenolic acids (compounds 1 and 2) were mainly distributed in cladodes (64.6%), while flavonoids (3-14) in the flowers (81.8%). Overall, the highest amount of total flavonoids (22.76 ± 0.015 mg of quercetin equivalent [QE]/g) and total phenolics (62.80 ± 0.009 mg gallic acid equivalents [GAE]/g) was found in the flower extract. Flavonoid glycosides have not been detected in the seeds and the flesh, while the fruit seed extract contained mainly feruloyl derivatives. Our data provide convincing evidences for the lack of cytotoxic and genotoxic effects of O. ficus indica aqueous extracts and, in parallel, support the potential for further exploitation of this plant in the food supplement or functional food sector.

Mutation of 4-coumarate: coenzyme A ligase 1 gene affects lignin biosynthesis and increases the cell wall digestibility in maize brown midrib5 mutants

BackgroundMaize brown midrib (bm) mutants associated with impaired lignin biosynthesis are a potential source for the breed of novel germplasms with improved cell wall digestibility. The spontaneous bm5 mutants had been identified since 2008. However, the gene responsible for the bm5 locus, and the comprehensive effects of bm5 mutation on lignin biosynthesis, soluble phenolics accumulation, and cell wall degradation have yet to be elucidated.ResultsThe bm5 locus was identified to encode a major 4-coumarate: coenzyme A ligase (Zm4CL1) through analyzing MutMap-assisted gene mapping data. Two alleles of Zm4CL1 isolated from bm5 mutants contained two transposons inserted in the first exon and the second intron, respectively, and consequently, the activities of 4CLs in the crude enzyme extracts from bm5 midribs were reduced by 51–62% compared with the wild type. Furthermore, five 4CLs were retrieved from maize genome, and Zm4CL1 was the most highly expressed one in the lignified tissues. Mutation of Zm4CL1 mainly impeded the biosynthesis of guaiacyl (G) lignins and increased the level of soluble feruloyl derivatives without impacting maize growth and development. Moreover, both neutral detergent fiber digestibility and saccharification efficiency of cell walls were significantly elevated in the bm5 mutant.ConclusionsZm4CL1 was identified as the Bm5 gene, since two independent alleles of Zm4CL1 were associated with the same mutant phenotype. Mutation of Zm4CL1 mainly affected G lignin biosynthesis and soluble feruloyl derivatives accumulation in maize lignified tissues. The reduced recalcitrance of the bm5 mutant suggests that Zm4CL1 is an elite target for cell wall engineering, and genetic manipulation of this gene will facilitate the utilization of crop straw and stover that have to be dealt with for environmental protection.

Screening of novel feruloyl esterases from Talaromyces wortmannii for the development of efficient and sustainable syntheses of feruloyl derivatives

The feruloyl esterases Fae125, Fae7262 and Fae68 from Talaromyces wortmannii were screened in 10 different solvent: buffer systems in terms of residual hydrolytic activity and of the ability for the transesterification of vinyl ferulate with prenol or l-arabinose. Among the tested enzymes, the acetyl xylan-related Fae125 belonging to the phylogenetic subfamily 5 showed highest yield and selectivity for both products in alkane: buffer systems (n-hexane or n-octane). Response surface methodology, based on a 5-level and 6-factor central composite design, revealed that the substrate molar ratio and the water content were the most significant variables for the bioconversion yield and selectivity. The effect of agitation, the possibility of DMSO addition and the increase of donor concentration were investigated. After optimization, competitive transesterification yields were obtained for prenyl ferulate (87.5–92.6%) and l-arabinose ferulate (56.2–61.7%) at reduced reaction times (≤24 h) resulting in good productivities (>1 g/L/h, >300 kg product/kg FAE). The enzyme could be recycled for six consecutive cycles retaining 66.6% of the synthetic activity and 100% of the selectivity.

Optimized Enzymatic Synthesis of Feruloyl Derivatives Catalyzed by Three Novel Feruloyl Esterases from Talaromyces wortmannii in Detergentless Microemulsions

Three novel feruloyl esterases (Fae125, Fae7262 and Fae68) from Talaromyces wortmannii overexpressed in the C1 platform were evaluated for the transesterification of vinyl ferulate with two acceptors of different size and lipophilicity (prenol and L-arabinose) in detergentless microemulsions. The effect of reaction conditions such as the microemulsion composition, the substrate concentration, the enzyme load, the pH, the temperature and the agitation were investigated. The type A Fae125 belonging to the subfamily 5 (SF5) of phylogenetic classification showed highest yields for the synthesis of both products after optimization of reaction conditions: 81.8% for prenyl ferulate and 33.0% for L-arabinose ferulate. After optimization, an 8-fold increase in the yield and a 12-fold increase in selectivity were achieved for the synthesis of prenyl ferulate.

Derivatives of Ferulic Acid: Structure, Preparation and Biological Activities

Ferulic acid is a natural compound that possesses multiple physiological and pharmaceutical functions. The chemical, physical, and pharmaceutical properties of this phenolic acid can be improved by derivatives with other active compounds. This sentence (Hence, such improvements can widen the applications of ferulic acid in the food, cosmetic, and pharmaceutical industries.) has been deleted. This article reviewed the identification, preparation, and biological activities of feruloyl derivatives of carbohydrates, glycerol and glycerides, amide, fatty alcohol, myo-inositol, and nitric oxide. It also briefly discussed other derivatives. Researchers are encouraged to carry out toxicological, pharmacokinetic, and clinical investigation of potent active feruloyl derivatives and to develop other derivatives. Review Article Pei et al.; ARRB, 5(6): 512-528, 2015; Article no.ARRB.2015.054 513

Antiproliferative evaluation of terpenoids and terpenoid coumarins from Ferulago macrocarpa (Fenzl) Boiss. fruits.

Background:Ferulago macrocarpa is a plant used as flavoring agent and protectant in the food industry and as a folk medicinal plant in Iran with no available information on its chemical identity. Ferulago spp. showed to contain biologically terpenoids and coumarins.Objective:The objective was to isolate and characterize terpenoids and coumarins from the acetone extract of F. macrocarpa fruits and to evaluate their antiproliferative effects on several cell lines.Materials and Methods:A series of normal and reverse phase gravity and high-performance liquid chromatography analyses were used to purify constituents. Compounds 1–5 and 7 were evaluated for their cytotoxic effects on MCF-7, HT-29 and H-1299 cell lines.Results:Six compounds including bornyl acetate (1), 1,10-di-epi-cubenol (2), stigmasterol (3) and three coumarins grandivittin (4), prantschimgin (5) and 4”-hydroxygrandivittin (7) along with mixtures of feruloyl derivatives (6a-6c) have been purified. Their structures were established by spectroscopic methods including nuclear magnetic resonance and MS analyses. Compound 2 showed moderate cytotoxicity effect with IC50 values of 5.0 and 6.7 mM on MCF-7 and HT-29, respectively.Conclusion:1,10-di-epi-Cubenol could be considered as a potential proliferation inhibitor of MCF-7 and HT-29 cell lines.

Structural characterization and radical scavenging activity of monomeric and dimeric cinnamoyl glucose esters from Petrorhagia velutina leaves

From the aerial parts of Petrorhagia velutina, a new dimeric p-coumaroyl glucose and two monomeric cis p-coumaroyl and feruloyl derivatives have been isolated along with three known related compounds. The structural characterization of these compounds has been elucidated by 1D and 2D NMR techniques. CAD mass spectra have allowed to confirm the spectroscopic structural analysis and to disclose the fragmentation pattern of the dimeric p-coumaroyl derivative. Radical scavenging efficacy of all the isolated metabolites was assessed by measuring their ability to scavenge DPPH radical and ABTS radical cation. The dimeric metabolite and the monomeric trans isomers showed an effective reducing power the oxidant probes.

Intramolecular stabilization of acylated betacyanins

Racemization and stability of the betacyanins, betanin (betanidin 5-O-glucoside) and amaranthin(betanidin 5-O-glucuronosylglucoside), under acidic conditions were compared with those of the corresponding feruloyl derivatives, lampranthin II and celosianin II. Both acylbetacyanins showed a reduced racemizationvelocity and celosianin II in addition an enhanced stability, possibly caused by intramolecular associationbetween the betanidin and the feruloyl moieties.

Betacyanins from fruits of Basella rubra

Ion spray mass spectrometry and tandem mass spectrometry of the fresh juice from Basella rubra fruits revealed the presence of betanidin monoglucoside as the major betacyanin and its 4-coumaroyl and feruloyl derivatives as minor components. Co-chromatography (TLC, HPLC) with betacyanin standards identified the betacyanins as gomphrenin I (15 S-betanidin 6- O-β-glucoside), gomphrenin II (15 S-betanidin 6- O-[6′- O-(4-coumaroyl)-β-glucoside]) together with small amounts of the respective R forms (isogomphrenin I and II) and gomphrenin III (15 S-betanidin 6- O-[6′- O-feruloyl-β-glucoside]).

Changes in flowering and the accumulation of polyamines and hydroxycinnamic acid-polyamine conjugates in tobacco plants transformed by the rolA locus from the Ri TL-DNA of Agrobacterium rhizogenes

Tobacco plants containing rolA (root locus A) from the Ri TL-DNA (root-inducing, left-hand, transferred DNA) from Agrobacterium rhizogenes have an altered phenotype, including male sterility, abnormal flower morphology, wrinkled leaves and shortened internodes. This phenotype is unstable, reverting to an attenuated form in lateral branches. We show that the pleiotropic effects of rolA are correlated with inhibition of the accumulation of conjugates between polyamines and the hydroxycinnamic acids. The compounds associated with male fertility are primarily affected, particularly the feruloyl derivatives.

Hydroxycinnamic acid derivatives of rheum rhaponticum

Further work on the polyphenols of Rheum rhaponticum has led to the isolation of a range of hydroxycinnamic acid derivatives. Compounds identified were the 1-glucose esters of ferulic, sinapic and p-coumaric acids. Several other feruloyl derivatives were found, some of which must have complex structures.