Cis-ferulic Acid Research Articles

Anti-Babesial Compounds from Berberis Vulgaris

Extracts of nine North African medicinal plants have been evaluated for their anti-babesial properties in vitro. The extracts of Berberis vulgaris and Rosa damascena showed more than 90% inhibition of the parasite growth at a test concentration of 100 μg/mL. In addition to berberine alkaloids, we isolated nine active ingredients from B. vulgaris: E-coniferyl alcohol, (-)-simulanol, p-hydroxybenzaldehyde, 3-hydroxy-4,5-dimethoxybenzoic acid, trans-ferulic acid, syringic acid, vanillic acid, cis-ferulic acid, and syringaresinol-β-D-glucoside. These compounds are all known, but are newly reported for B. vulgaris. Among them, trans-ferulic acid showed the lowest IC50 value (7.33 μg/mL), not much above that of the standard drug, diminazene aceturate (0.60 μg/mL).

Diferulate Content of Maize Sheaths Is Associated with Resistance to the Mediterranean Corn Borer Sesamia nonagrioides (Lepidoptera: Noctuidae)

The leaf sheaths of selected inbred lines of maize (Zea mays L.) with variable levels of stem resistance to the Mediterranean corn borer Sesamia nonagrioides (Lefèvbre) were evaluated for antibiotic effect on insect development. Phytochemical analyses of leaf sheaths were conducted for cell wall phenylpropanoid content to gain a better understanding of maize-resistance mechanisms. Laboratory bioassays established that sheath tissues from different genotypes significantly affected the growth of neonate larvae. Three hydroxycinnamates, p-coumaric, trans-ferulic, and cis-ferulic acids, and three isomers of diferulic acid, 8-5', 8-O-4', and 8-5' b (benzofuran form), were identified. Significant negative correlations were found between larvae weight and diferulic acid content for six genotypes. These results are in agreement with previous studies concerning the role of cell wall structural components in stem borer resistance.

Putative Role of Pith Cell Wall Phenylpropanoids in Sesamia nonagrioides (Lepidoptera: Noctuidae) Resistance

The stem borer Sesamia nonagrioides (Lefèbvre) is the most important insect pest that attacks maize, Zea mays L., in northwestern Spain. Host plant resistance to this borer was investigated in relation to the cell wall phenylpropanoids content in the pith. Eight inbred lines that differ in resistance were analyzed. Three major simple phenolic acids, p-coumaric, trans-ferulic, and cis-ferulic acids, and three isomers of diferulic acid, 8-5', 8-O-4', and 8-5'b (benzofuran form), were identified. The amount of all these compounds was correlated with the resistance level in the genotypes, with the resistant inbreds having the highest concentrations. The role of these compounds in cell wall fortification and lignification is well-documented, suggesting their possible intervention in S. nonagrioides resistance. Future studies that focus on these compounds could be useful to enhance S. nonagroides resistance.

Association of non‐starch polysaccharides and ferulic acid in grain amaranth (Amaranthus caudatus L.) dietary fiber

The association of ferulic acid, an alkali-extractable phenolic acid in amaranth (Amaranthus caudatus L., Amaranthaceae) insoluble fiber (trans-ferulic acid: 620 microg.g-1, cis-ferulic acid: 203 microg.g-1), and non-starch polysaccharides was investigated. Enzymatic hydrolysis of insoluble amaranth fiber released several feruloylated oligosaccharides that were separated using Sephadex LH-20-chromatography and reversed phase-high performance liquid chromatography (RP-HPLC). Three compounds were unambiguously identified: O-(6-O-trans-feruloyl-beta-D-galactopyranosyl)-(1-->4)-D-galactopyranose, O-(2-O-trans-feruloyl-alpha-L-arabinofuranosyl)-(1-->5)-L-arabinofuranose, and O-alpha-L-arabinofuranosyl-(1-->3)-O-(2-O-trans-feruloyl-alpha-L-arabinofuranosyl)-(1-->5)-L-arabinofuranose. These feruloylated oligosaccharides show that ferulic acid is predominantly bound to pectic arabinans and galactans in amaranth insoluble fiber. 5-O-trans-Feruloyl-L-arabinofuranose was the only compound isolated in pure form from an acid hydrolyzate. This compound may have its origin from pectic arabinans but also from arabinoxylans.

Free, esterified, and insoluble-bound phenolic acids in white and red Korean ginsengs ( Panax ginseng C.A. Meyer)

Phenolic acids of dried white and red ginsengs were extracted and fractionated into free, esterified, and insoluble-bound forms. The contents of individual phenolic acids in different forms were quantified by gas–liquid chromatography. Identification of all phenolic acids was confirmed by gas chromatography–mass spectrometry and comparison of gas chromatographic retention times. Twelve different phenolic acids as free, esterified, and insoluble-bound forms were identified in Korean ginsengs. Total phenolic acids in white and red ginsengs were 27.2 and 26.8 mg/100 g, respectively. Seven free phenolic acids were identified and their total contents in white and red ginsengs were 4.70 and 4.14 mg/100 g, respectively. trans-Ferulic acid was the predominant free phenolic acid, representing 47.9 and 57.7% of total free phenolic acids in white and red ginsengs, respectively. Esterified phenolic acids represented 71.9 and 77.1% of total phenolic acids in white and red ginsengs, respectively. The most predominant esterified phenolic acids were cis-ferulic acid and trans-ferulic acid. Total insoluble-bound phenolic acid contents in white and red ginsengs were 2.93 and 1.99 mg/100 g, respectively. Ferulic acid ( cis and trans isomers) was also the major insoluble-bound phenolic acids. This paper represents the first report of systematic identification and quantification of phenolic acids in different forms in white and red Korean ginsengs.

Allelochemicals in wheat (Triticum aestivum L.): variation of phenolic acids in shoot tissues.

Seven known phenolic acids implicated in wheat allelopathy were analyzed in a worldwide collection of 58 wheat accessions by gas chromatography and tandem mass spectrometry (GC-MS-MS). Chemical analysis showed that accessions differed significantly in the production of p-hydroxybenzoic, vanillic, syringic, trans-p-coumaric, cis-p-coumaric, trans-ferulic, and cis-ferulic acids in the shoots of 17-day-old wheat seedlings. The concentrations of p-hydroxybenzoic, vanillic, cis-p-coumaric, and cis-ferulic acids were normally distributed in the 58 accessions. A binormal distribution was found for syringic and trans-ferulic acids and a skewed normal distribution for trans-p-coumaric acid. The concentration of each compound also varied with phenolic acids. The relative abundance of each phenolic acid was ordered decreasingly as trans-ferulic, vanillic, trans-p-coumaric, p-hydroxybenzoic, syringic, cis-ferulic, and cis-p-coumaric acids. The concentration of total identified phenolic acids varied from 93.2 to 453.8 mg/kg in the shoots of 58 accessions. The content of each phenolic acid or group was highly associated with others in the shoots of wheat seedlings. Wheat accessions with high levels of total identified phenolic acids in the shoots are generally strongly allelopathic to the growth of annual ryegrass.

Distribution and Exudation of Allelochemicals in Wheat Triticum aestivum

Wheat allelopathy has potential for weed suppression. Allelochemicals were identified in wheat seedlings, and they were exuded from seedlings into agar growth medium. p-Hydroxybenzoic, trans-p-coumaric, cis-p-coumaric, syringic, vanillic, trans-ferulic, and cis-ferulic acids and 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) were identified in both the shoots and roots of 17-day-old wheat seedlings and their associated agar growth medium. Wheat accessions with previously identified allelopathic activity tended to contain higher levels of allelochemicals than poorly allelopathic ones. The allelopathic compounds present in the shoots generally also were identified in the roots and in the agar medium. Allelochemicals were distributed differentially in wheat, with roots normally containing higher levels of allelochemicals than the shoots. When the eight allelochemicals were grouped into benzoic acid and cinnamic acid derivatives, DIMBOA, total coumaric, and total ferulic acids, the amount of each group of allelochemicals was correlated between the roots and the shoots. Most of the allelochemicals identified in the shoots and roots could be exuded by the living roots of wheat seedling into the agar growth medium. However, the amounts of allelochemicals in the agar growth medium were not proportional to those in the roots. Results suggest that wheat plants may retain allelochemicals once synthesized. The presence of allelochemicals in the agar growth medium demonstrated that wheat seedlings were able to synthesize and to exude phytotoxic compounds through their root system that could inhibit the root growth of annual ryegrass.

The identification and quantitation of the hydroxycinnamic acid substituents of a polysaccharide extracted from maize bran

The composition and carbohydrate structure of hemicelluloses namely branan ferulate isolated from maize bran has been determined. This novel polysaccharide material is the base polysaccharide of Sterigel™, a Seton Scholl preparation which is being used successfully as a wound management aid. The structure of the polysaccharide was determined by methylation followed by GC-MS analysis, and 1H- and 13C-NMR spectroscopic analysis. It was shown to be composed of a (1→4)-β-D-xylan backbone substituted with a variety of side-chain components, such as single α-D- glucuronic acid residues (via an α-D-GlcA-(1→2)-linkage to the xylan backbone), single α-L-arabinose residues (via α-L-Araf-(1→2)- and/or α-L-Araf-(1→3)-linkages to the xylan backbone) and longer chains of 2–3 monosaccharide residues containing arabinose, xylose and galactose (in the form α-D- Galp-(1→4)-β-D-Xylp-(1→2)-α-L-Araf, linked to the xylan backbone via α-L-Araf-(1→2)- and/or α-L- Araf-(1→3)-linkages). In addition to the carbohydrate, non-carbohydrate moieties such as hydroxycinnamic acids and some proteins, detected using scanning UV spectroscopy (190–450 nm), are present in the branan ferulate. The hydroxycinnamic acids appear to be bound to the polysaccharide chains via ester linkages between their carboxylic acid groups and the C-5 hydroxyl group of a proportion of the α-L-Araf residues, the location of which are detailed above. Predominantly trans-ferulic acid (0.38% w/w), and small amounts of cis-ferulic acid (0.06% w/w) and trans-p-coumaric acid (0.02% w/w) were extracted with ethyl acetate after hydrolysis using 2 M NaOH and identified using GC and GC-MS. Hydrolysis with an aryl ester hydrolase (EC 3.1.1.2) was carried out to confirm the presence of the ferulate ester linkages. HPLC results confirmed that the ferulic acid is released by the enzyme (0.25% w/w). GPC analysis using UV (280 nm) and RI detection confirmed that the ferulic acid was bound to the polysaccharide chain since the distributions directly overlapped, indicating the presence of little or no free ferulic acids. Indeed, free ferulic acid contents of <0.02% w/w were determined in extracts of solid branan ferulate and an aqueous solution of branan ferulate, by HPLC. © 1999 Society of Chemical Industry

Norisoprenoids from Viburnum dilatatum

A new norisoprenoid, (3 R,6 R,7 E)-3-hydroxy-4,7-megastigmadien-9-one, was isolated together with seven known norisoprenoids, (−)-loliolide, (+)-isololiolide, (6 R,7 E)-4,7-megastigmadien-3,9-dione, (6 S,7 E)-6-hydroxy-4,7-megastigmadien-3,9-dione, (3 S,7 E)-3-hydroxy-5,7-megastigmadien-9-one, (3 S,5 R,6 S,7 E)-5,6-epoxy-3-hydroxy-7-megastigmene-9-one, (3 S,5 R,7 E,8 R)-3,5-dihydroxy-6,7-megastigmadien-9-one and eight known phenolic compounds, trans-ferulic acid, cis-ferulic acid, trans- p-coumaroyl methyl ester, umbelliferone, veratric acid, p-hydroxybenzaldehyde, p-hydroxybenzoic acid, p-methoxybenzoic acid, from the leaves of Viburnum dilatatum. Their structures were established on the basis of chemical evidence and spectral data.

Evolution of Antioxidant Activity during Kilning: Role of Insoluble Bound Phenolic Acids of Barley and Malt

Phenolic acids, bound to the cellular walls of the germinated barley, are very interesting potential antioxidants of beer. Indeed, the antioxidant activity due to these bound compounds is about 2-fold higher than the activity due to the free phenolic compounds. Seven phenolic acids were separated by HPLC after alkaline hydrolysis of the cake resulting from a methanolic extraction of barley or malt. Three main compounds, trans-ferulic acid, trans-p-coumaric acid, and cis-ferulic acid, were quantified using an external standard method. They respectively represent 177.79, 78.50, and 47.15 μg/g of dry matter of germinated barley. Responsible for 20-40% of the antioxidant activity of the hydrolyzed cake, they probably have a real influence on the evolution of this activity during kilning.

Cell wall-bound trans- and cis-ferulic acids in growing maize roots

Cell wall-bound trans- and cis-ferulic acids in growing maize roots

Senegoses A--E, oligosaccharide multi-esters from Polygala senega var. latifolia Torr. et Gray.

From the roots of Polygala senega var. latifolia Torr. et Gray five new oligosaccharides, called senegoses A--E, were isolated and their structures were elucidated by spectroscopic and chemical means. These oligosaccharides were esterified with acetic, benzoic, trans-ferulic and cis-ferulic acids.

Formation and Identification of Cis/Trans Ferulic Acid in Photoyellowed White Spruce Mechanical Pulp

Abstract Direct studies of photoyellowed unbleached white spruce refiner mechanical pulp have been carried out using laser Raman spectroscopy, gas chromatography/mass spectrometry (GC/MS) and Fourier transform infrared spectroscopy (FTIR) techniques. A new chromophore, namely, cis-ferulic acid has been detected. The experimental results indicate the presence of both cis and trans isomers of ferulic acid. The former, because of its yellow color, is considered to be a contributor in the yellowing process.