trans-p-Coumaric acid

A Novel, Simple Rapid Reverse-Phase HPLC-DAD Analysis, for the Simultaneous Determination of Phenolic Compounds and Abscisic Acid Commonly Found in Foodstuff and Beverages.[Pubmed:34553229]

J Chromatogr Sci. 2021 Sep 22. pii: 6374069.

A novel, simple, rapid, 7-minute HPLC-DAD method for the determination of 10 phenolic compounds and abscisic acid commonly found in teas, wines, fruit and honey was successfully developed and validated according to the International Council of Harmonization (ICH) guidelines. This reverse-phase (RP) HPLC-DAD method boasts rapid separation and excellent resolution while introducing green chemistry techniques. The Agilent 1200 series diode array detector SL coupled with a reverse-phase Advanced Materials Technology Halo C18 column (100 x 3.0 mm i.d., 2.7 mum) contributed to the rapid analyses. This, together with a 0.1% formic acid in water (v/v) and methanol mobile phase, a flow rate of 0.8 mL/min and the utilization of a meticulous gradient elution resulted in a validated method for the determination of 10 phenolic compounds and abscisic acid commonly found in various foodstuffs. The resulting method proved to be rapid, accurate, precise and linear with sensitive detection limits from 0.025 mug/mL to 0.500 mug/mL and percentage recoveries of 98.07%-101.94%. Phenolic compounds have been acknowledged throughout literature for their therapeutic properties, interalia, antioxidant, anti-inflammatory and antiaging due to free radical scavenging potentials. However, resulting analysis, can be frequently complicated and long and very often discounts green chemistry techniques. The developed and validated method successfully and rapidly analyses, gallic acid, caffeic acid, trans-p-Coumaric acid, rutin, myricetin, abscisic acid, trans-cinnamic acid, quercetin, luteolin, kaempferol and chrysin with excellent resolution and precision.

Concentrations of Phenolic Acids Are Differently Genetically Determined in Leaves, Flowers, and Grain of Common Buckwheat (Fagopyrum esculentum Moench).[Pubmed:34205223]

Plants (Basel). 2021 Jun 3;10(6). pii: plants10061142.

Common buckwheat (Fagopyrum esculentum Moench) is a valuable source of proteins, B vitamins, manganese, tryptophan, phytochemicals with an antioxidant effect, and the natural flavonoid rutin. Due to its composition, buckwheat supports the human immune system, regulates blood cholesterol, and is suitable for patients with diabetes or celiac disease. The study aimed to compare the allocation of selected phenolic acids (neochlorogenic acid, chlorogenic acid, trans-caffeic acid, trans-p-Coumaric acid, trans-sinapic acid, trans-ferulic acid) and flavonoids (rutin, vitexin, quercetin, kaempferol) in the leaves, flowers, and grain of buckwheat cultivars of different origin. The content of individual phenolics was determined by the HPLC-DAD method. The results confirmed the determining role of cultivar on the relative content of chlorogenic acid, trans-caffeic acid, trans-sinapic acid, vitexin, and kaempferol in buckwheat plants. A significantly negative correlation among concentrations of phenolic acids in different common buckwheat plant parts shows that there are different mechanisms of genetic influences on the concentration of phenolic substances in common buckwheat flowers, leaves, and grain. These differences should be taken into account when breeding buckwheat for a high concentration of selected phenolic substances.

[A new 9,19-cycloartane glycoside from Asplenium ruprechtii].[Pubmed:33787110]

Zhongguo Zhong Yao Za Zhi. 2021 Mar;46(5):1155-1159.

Chemical constituents of water extracts of Asplenium ruprechtii were investigated. Five compounds were isolated by silica gel, Sephadex LH-20 gel column chromatographies and preparative HPLC, and their structures were identified by various spectral analyses as aspleniumside G(1), trans-p-Coumaric acid(2), trans-p-Coumaric acid 4-O-beta-D-glucoside(3), cis-p-coumaric acid 4-O-beta-D-glucoside(4), and(E)-ferulic acid-4-O-beta-D-glucoside(5). Among them, compound 1 is a new 9,19-cycloartane glycoside.

Quantification of phenolic compounds in different types of crafts beers, worts, starting and spent ingredients by liquid chromatography-tandem mass spectrometry.[Pubmed:31653471]

J Chromatogr A. 2020 Feb 8;1612:460622.

An accurate quantification of phenolic compounds present in several kind of craft beers, corresponding worts, ingredients and spent products was performed by LC-MS/MS in this study. The dilution 1:2 of the sample with the mobile phase gave the best results, offering a very fast and simple method to reduce the matrix effect. A validated method was applied to six different types of craft beers, their worts, starting and spent products, such as barley malts and barley husks, starting hops and spent hops, and finally, starting yeast and spent yeasts to quantify the selected phenolic compounds. The Total Phenol Content (TPC) of barley malts is not negligible and it results almost prevalently due to trans-p-Coumaric acid, which ranges from 76.4 mug/Kg for Mais to 672.6 mug/Kg for Munich. The trans-p-Coumaric acid is transferred to the worts during the must preparation and is responsible for the not negligible TPC of worts, that was between 131.1 mug/Kg for Ego to 2041.6 mug/Kg for Alter beer. Bitter acids and prenylflavonoids are mainly present in the starting hops (TPC 323.8 mug/Kg and TPC 500.3 for Saaz and Perle hops, respectively). Their concentration strongly decreases in the spent hops where the TPC ranges between 8.0 mug/Kg for Triplo Malto to 24.4 mug/Kg for Alter, suggesting that they are transferred to the intermediate of production. Phenolic compounds, originally present in the starting barley malts and hops, are limitedly present into the final beers, and their TPC ranges approximately from 65.6 mug/Kg for Fiat lux to 105.3 mug/Kg for Alter. Actually, most phenolic compounds are absorbed into the yeast added for the fermentation, as it is clearly evident from the observation that spent yeasts contain a higher phenolic compounds amount with the respect to the starting yeast, and several phenolic compounds, in particular those coming from hops, are originally absent into the yeast and are only present in the spent ones.

[A new lupane-type triterpenoid from Dichroa hirsuta].[Pubmed:31342709]

Zhongguo Zhong Yao Za Zhi. 2019 May;44(9):1829-1835.

The chemical constituents from methanol extract of Dichroa hirsuta were separated by silica gel and Sephadex LH-20 column chromatography,high pressure preparative liquid chromatography( HPLC) and recrystallization. Their structures were elucidated by NMR and MS. Nine compounds were obtained and their structures were identified as 3beta,21alpha-O-diacetyl-lup-9( 11)-en-7beta-ol( 1),( Z)-methyl p-hydroxycinnamate( 2),cis-p-coumaric acid ethyl ester( 3),( E)-methyl p-hydroxycinnamate( 4),trans-p-Coumaric acid ethyl ester( 5),4( 3 H)-quinazolinone( 6),7-hydroxycoumarin( 7),hydrangenol( 8) and thunberginol C( 9). Compound 1 is a new lupane-type triterpenoid,and compounds 1-5,8-9 were firstly isolated from this plant. Dual reporter assay results showed that compounds 2-5 could activate the Nrf2-ARE signaling pathway.

Acylated pelargonidin glycosides from the red-purple flowers of Iberis umbellata L. and the red flowers of Erysimum x cheiri (L.) Crantz (Brassicaceae).[Pubmed:30605852]

Phytochemistry. 2019 Mar;159:108-118.

Five previously undescribed acylated pelargonidin 3-sophoroside-5-glucosides (pigments 2-6) were isolated from the red-purple flowers of Iberis umbellata L. 'Candycane Rose' and 'Candycane Red', in addition to a known one (pigment 1). The structures of five undescribed acylated anthocyanins were determined by chemical and spectroscopic methods to be pelargonidin 3-O-[2-O-(2-O-("acyl-A")-beta-glucopyranosyl)-6-O-("acyl-B")-beta-glucopyranoside ]-5-O-[6-O-(malonyl)-beta-glucopyranoside], in which the "acyl-A" group was either trans-sinapic (2), trans-ferulic (3), trans-sinapic (4), trans-ferulic (5), or trans-ferulic acid (6), and "acyl-B" was either glucosyl-trans-p-Coumaric acid (2), glucosyl-trans-p-Coumaric acid (3), trans-feruloyl-glucosyl-trans-p-Coumaric acid (4), trans-feruloyl-glucosyl-trans-p-Coumaric acid (5), or glucosyl-trans-feruloyl-glucosyl-trans-p-Coumaric acid (6). Moreover, three previously undescribed acylated pelargonidin 3-sambubioside-5-glucosides (pigments 7, 8, and 10) and one undescribed acylated pelargonidin 3-(3(X)-glucosylsambubioside)-5-glucoside (pigment 9) were isolated from the red flowers of Erysimumxcheiri (L.) Crantz 'Aurora' as major anthocyanins. The structures of the three undescribed acylated pelargonidin 3-sambubioside-5-glucosides were determined to be pelargonidin 3-O-[2-O-(2-O-("acyl-C")-beta-xylopyranosyl)-6-O-("acyl-D")-beta-glucopyranoside] -5-O-(beta-glucopyranoside), in which the "acyl-C" group was either non (7), non (8), or trans-p-Coumaric acid (10) and "acyl-D" was either trans-p-coumaric (7), trans-ferulic (8), or trans-p-Coumaric acid (10). Moreover, a previously undescribed acylated pelargonidin 3-(3(X)-glucosylsambubioside)-5-glucoside was identified to be pelargonidin 3-O-[2-O-(2-O-(trans-p-coumaroyl)-3-O-(beta-glucopyranosyl)-beta-xylopyranosyl)-6 -O-(trans-p-coumaroyl)-beta-glucopyranoside]-5-O-(beta-glucopyranoside) (9). In addition, the distribution of anthocyanidins structural elements in 24 Brassicaceous species is compared.

Process for the Purification of cis-p-Coumaric Acid by Cellulose Column Chromatography after the Treatment of the trans Isomer with Ultraviolet Irradiation.[Pubmed:30305597]

Anal Sci. 2018;34(10):1195-1199.

A methanolic solution of trans-p-Coumaric acid was exposed to ultraviolet radiation and a mixture solution of the trans and cis isomers was subjected to cellulose column chromatography, eluting with an aqueous 0.1% trifluoroacetic acid solution containing methanol (90:10, v/v). Separation of the trans and cis isomers was achieved. The identity of the cis isomer was confirmed by TLC, HPLC, and NMR. Since both the support and eluent are inexpensive, the cis isomers can be obtained economically on both the laboratory and industrial scales.

New phenylpropanoids from Bulbophyllum retusiusculum.[Pubmed:30151611]

Arch Pharm Res. 2018 Nov;41(11):1074-1081.

Two new phenylpropanoids, retusiusines A (1) and B (2), and a pair of new phenylpropyl enantiomers, (+/-)-retusiusine C (3a and 3b), together with eight known compounds, dihydroconiferyl dihydro-p-coumarate (4), methyl 3-(4-hydroxyphenyl) propionate (5), 3-(4-hydroxyphenyl)-propanoic acid (6), dihydroferulic acid (7), methyl 3-(4-methoxyphenyl) propionate (8), 3-(3,4-dimethoxyphenyl)-2-propenal (9), trans-p-Coumaric acid (10) and dihydroconiferyl alcohol (11), were isolated from the tubers of Bulbophyllum retusiusculum. The absolute configurations of the new compounds were determined by calculating their electronic circular dichroism (ECD), spectra and specific optical rotations and comparing the calculated values with the experimental data. Compound 2 exhibited potent antifungal activity against Candida albicans (16 mug/mL). Compound 3 showed moderate antibacterial activity against Bacillus subtilis (64 mug/mL).

Identification and Growth Inhibitory Activity of the Chemical Constituents from Imperata Cylindrica Aerial Part Ethyl Acetate Extract.[Pubmed:30037062]

Molecules. 2018 Jul 21;23(7). pii: molecules23071807.

Imperata cylindrica (L.) Raeusch. (IMP) aerial part ethyl acetate extract has anti-proliferative, pro-apoptotic, and pro-oxidative effects towards colorectal cancer in vitro. The chemical constituents of IMP aerial part ethyl acetate extract were isolated using high-performance liquid chromatography (HPLC) and identified with tandem mass spectrometry (ESI-MS/MS) in combination with ultraviolet-visible spectrophotometry and 400 MHz NMR. The growth inhibitory effects of each identified component on BT-549 (breast) and HT-29 (colon) cancer cell lines were evaluated after 48/72 h treatment by MTT assay. Four isolated compounds were identified as trans-p-Coumaric acid (1); 2-Methoxyestrone (2); 11, 16-Dihydroxypregn-4-ene-3, 20-dione (3); and Tricin (4). Compounds (2), (3), and (4) exhibited considerable growth inhibitory activities against BT-549 and HT-29 cancer cell lines. Compounds (2), (3), and (4) are potential candidates for novel anti-cancer agents against breast and colorectal cancers.

Facile Chemoselective Strategy toward Capturing Sphingoid Bases by a Unique Glutaraldehyde-Functionalized Resin.[Pubmed:30023788]

ACS Omega. 2018 Jan 31;3(1):753-759.

Sphingoid bases, which have a 2-amino-1,3-diol common functional group, are the structural backbone units of all sphingolipids. Recently, much attention has been focused on sphingoid bases because of their potentially beneficial bioactivities toward various cancer cells as well as their dietary interest. However, low abundance and the handling complexity caused by their amphiphilic character led to very limited research on them. Glutaraldehyde has two aldehyde groups, and it reacts rapidly with the 2-amino-1,3-diol functional group of sphingosine to give a tricyclic product. Immobilization of glutaraldehyde on a resin was successfully performed by organic synthesis, starting from trans-p-Coumaric acid via eight steps. This approach suppresses the self-polymerization of glutaraldehyde, and addition of water to the developed resin causes the formation of cyclic double hemiacetal function, which avoids oxidation like a reducing sugar in nature and makes it stable even for up to 1 year incubation. The resin was applied to the solid-phase extracting experiment of free sphingosine from human serum at a concentration of 280 nM. Another extraction study of edible golden oyster mushrooms showed that the sphingoid base was selectively captured from complex natural extracts. These results demonstrate that the developed glutaraldehyde resin method is a highly selective method, and hence, the combination of it with the o-phthaldialdehyde HPLC method was confirmed as an efficient and sensitive method for analysis of sphingoid bases in biological samples.

The Occurrence of Flavonoids and Related Compounds in Cedrus brevifolia A. Henry ex Elwes & A. Henry Needles. Inhibitory Potencies on Lipoxygenase, Linoleic Acid Lipid Peroxidation and Antioxidant Activity.[Pubmed:29280942]

Plants (Basel). 2017 Dec 27;7(1). pii: plants7010001.

The phytochemical analysis of the polar extracts of Cedrus brevifolia needles yielded 20 compounds, namely from the methanol extract we isolated three flavonoids (1-3), one hydrolysable tannin (4), eleven phenolic derivatives (5-15) and one apocarotenoid (16), while from the methanol: water (5:1) extract we isolated four flavonoids (17-20). Chemical structures of all isolated compounds were determined by 1D, 2D-NMR (1 Dimension, 2 Dimensions Nuclear Magnetic Resonance) and UV-Vis (Ultraviolet-Visible) spectroscopy. Furthermore, the antioxidant potentials and the anti-inflammatory activities of both crude extracts and isolates were evaluated through DPPH radical scavenging capability, linoleic acid lipid peroxidation inhibition, and soybean LOX inhibition assays. This is the first report on the chemical profile of C. brevifolia needles. Catechin was the main compound derived from the methanol extract. According to our results, 4-O-beta-d-glucopyranyl trans-p-Coumaric acid and taxifolin were the most active ingredients.

Conformational Map of Phenolic Acids.[Pubmed:29215883]

J Phys Chem A. 2018 Jan 18;122(2):646-651.

The benefits of vaporization by laser ablation and the high resolution and sensitivity attained by the chirped pulse Fourier transform microwave spectroscopy CP-FTMW have provided the first conformational map of the simplest phenolic acids of trans-cinnamic and p-coumaric. Two conformers of trans-cinnamic acid and four conformers of trans-p-Coumaric acid have been characterized under the isolation conditions of a supersonic expansion. The spectroscopic constants derived from the analysis of the rotational spectra compared with those predicted theoretically provide an unmatched means to achieve an unambiguous identification of the observed species.