scholarly journals Biogenesis of rosmarinic acid in Mentha

1970 ◽  
Vol 118 (2) ◽  
pp. 291-297 ◽  
Author(s):  
B. E. Ellis ◽  
G. H. N. Towers
Keyword(s):  
Lactic Acid ◽  
Chlorogenic Acid ◽  
Cinnamic Acid ◽  
Rosmarinic Acid ◽  
Time Course ◽  
Turnover Rate ◽  
Mentha Piperita ◽  
Coumaric Acid ◽  
Acid Moiety ◽  
Insoluble Polymers

The biogenesis of rosmarinic acid (α-O-caffeoyl-3,4-dihydroxyphenyl-lactic acid), the second most common ester of caffeic acid in the plant kingdom, was studied in Mentha arvense and Mentha piperita. Administration of 14C-labelled compounds showed that, whereas the caffeoyl moiety was formed from phenylalanine via cinnamic acid and p-coumaric acid, the 3,4-dihydroxyphenyl-lactic acid moiety was formed from tyrosine and 3,4-dihydroxyphenylalanine. Time-course studies and the use of labelled rosmarinic acid showed that endogenous rosmarinic acid had a low turnover rate. The caffeoyl moiety did not appear to contribute to the formation of insoluble polymers, as has been suggested for chlorogenic acid in other plants.

scholarly journals Polyphenol Profile and Antimicrobial and Cytotoxic Activities of Natural Mentha × piperita and Mentha longifolia Populations in Northern Saudi Arabia

Processes ◽  
2020 ◽  
Vol 8 (4) ◽  
pp. 479 ◽  
Author(s):  
Hosam O. Elansary ◽  
Agnieszka Szopa ◽  
Paweł Kubica ◽  
Halina Ekiert ◽  
Marta Klimek-Szczykutowicz ◽  
...  
Keyword(s):  
Saudi Arabia ◽  
Chlorogenic Acid ◽  
Cancer Cells ◽  
Rosmarinic Acid ◽  
Biologically Active ◽  
Mentha Piperita ◽  
Cytotoxic Activities ◽  
Coumaric Acid ◽  
Leaf Extracts ◽  
Mentha Longifolia

New sources of polyphenols with anticancer, antioxidant, and antimicrobial properties in arid environments are critical for the development of alternative medicines and natural remedies. This study explored the polyphenol profiles and biological activities of methanolic leaf extracts from natural Mentha × piperita and Mentha longifolia populations in northern Saudi Arabia. Chromatographic analyses identified several polyphenols in M. × piperita including phenolic acids: rosmarinic acid (1547.6 mg/100 g DW (dry weight)), cryptochlorogenic acid (91.7 mg/100 g DW), and chlorogenic acid (69.4 mg/100 g DW), as well as flavonoids: naringin (328.8 mg/100 g DW) and cynaroside (162.8 mg/100 g DW). The major polyphenols in M. longifolia were: rosmarinic acid (781.6 mg/100 g DW), cryptochlorogenic acid (191.1 mg/100 g DW), p-coumaric acid (113.0 mg/100 g DW), m-coumaric acid (112.2 mg/100 g DW), and chlorogenic acid (63.8 mg/100 g DW). M. × piperita and M. longifolia leaf extracts had high antioxidant activities due to the major polyphenols (cynaroside, rosmarinic and cryptochlorogenic acids). M. × piperita had higher activities against different cancer cells than M. longifolia. Naringin, cryptochlorogenic acid, and rosmarinic acid had the highest activities against cancer cells. The leaf extracts had antibacterial effects against most bacteria species (Pseudomonas aeruginosa was most sensitive), which was attributed to the polyphenols. Antifungal activities were similarly broad (Aspergillus flavus was most sensitive) and attributed to naringin, cryptochlorogenic acid, and caffeic acid. Populations of M. × piperita and M. longifolia in Northern Riyadh may be a valuable source of natural biologically active compounds.

scholarly journals Anti-malarial Activity Of Phenolic Acids Is Structurally Related

2020 ◽  
Author(s):  
Prince A Fordjour ◽  
Jonathan P Adjimani ◽  
Bright Asare ◽  
Nancy O Duah-Quashie ◽  
Neils B Quashie
Keyword(s):  
Plasmodium Falciparum ◽  
Ferulic Acid ◽  
Chlorogenic Acid ◽  
Gallic Acid ◽  
Caffeic Acid ◽  
Phenolic Acids ◽  
Rosmarinic Acid ◽  
Protocatechuic Acid ◽  
Antimalarial Activity ◽  
Coumaric Acid

Abstract Background In the absence of an effective vaccine against malaria, chemotherapy remains a major option in the control of the disease. Then, the recent report of the emergence and spread of clones of Plasmodium falciparum resistant to available antimalarial drugs should be of concern as it poses a threat to disease control. Compounds whose pharmacological properties have been determined and touted for other disease can be investigated for antimalarial activity. Phenolic acids (polyphenols) have been reported to exhibit antioxidant, anticancer, anti-inflammatory, antiviral and antibiotic effects. However, information on their antimalarial activity is scanty. Phenolic acids are present in a variety of plant-based foods: mostly high in the skins and seeds of fruits as well as the leaves of vegetables. Systematic assessment of these compounds for antimalarial activity is therefore needed. Method Using the classical in vitro drug test, the antimalarial activities of five hydroxycinnamic acids, (caffeic acid, rosmarinic acid, chlorogenic acid, o-Coumaric acid and ferulic acid) and two hydroxybenzoic acids (gallic acid and protocatechuic acid) against 3D7 clones of Plasmodium falciparum was determined. Results Among the phenolic acids tested, caffeic acid and gallic acid were found to be the most effective, with mean IC 50 value of 17.73µg/ml and 26.59µg/ml respectively for three independent determinations. Protocatechuic acid had an IC 50 value of 30.08 µg/ml. Rosmarinic acid and chlorogenic acid, showed moderate antimalarial activities with IC 50 values of 103.59µg/ml and 105µg/ml respectively. The IC 50 values determined for ferulic acid and o-Coumaric acid were 93.36µg/ml and 82.23µg/ml respectively. Conclusion The outcome of this study suggest that natural occurring phenolic compounds have appreciable level of antimalarial activity which can be exploited for use through combination of actions/efforts including structural manipulation to attain an increase in their antimalarial effect. Eating of natural food products rich in these compounds could provide antimalarial prophylactic effect.

scholarly journals Analysis of triterpenoids, carotenoids, and phenylpropanoids in the flowers, leaves, roots, and stems of white bitter melon (Cucurbitaceae, Momordica charantia)

2021 ◽  
Vol 20 (1) ◽  
pp. 155-160
Author(s):  
Do Manh Cuong ◽  
Ramaraj Sathasivam ◽  
Chang Ha Park ◽  
Hyeon Ji Yeo ◽  
Ye Eun Park ◽  
...  
Keyword(s):  
Chlorogenic Acid ◽  
Gallic Acid ◽  
Cinnamic Acid ◽  
Developmental Stages ◽  
Momordica Charantia ◽  
Bitter Melon ◽  
Coumaric Acid ◽  
Direct Sunlight ◽  
Β Carotene ◽  
Different Parts

Purpose: To evaluate the contents of carotenoids, triterpenoids, and phenylpropanoids in different parts of white bitter melon.Methods: We evaluated the accumulation of 2 triterpenoids, 10 carotenoids, and 11 phenylpropanoids in different parts of white bitter melon, including fruits at four different developmental stages using HPLC.Results: Charantin, lutein, and rutin were the main triterpenoids, carotenoids, and phenylpropanoids, respectively. The accumulation of triterpenoids (momordicine and charantin), carotenoids (antheraxanthin, lutein, violaxanthin, α-carotene, and β-carotene), and phenylpropanoids (caffeic acid, chlorogenic acid, epicatechin, gallic acid, p-coumaric acid, rutin, and trans-cinnamic acid) was high inthe leaves and/or flowers, which are exposed to direct sunlight, but low in the roots.Conclusion: Most of the analyzed components were accumulated at high levels in the leaves and/or flowers. These results will help exploit the compounds in various parts of white bitter melon that are beneficial for human health. Keywords: Momordica charantia, Bitter melon, Triterpenoid, Carotenoid, Phenylpropanoid

scholarly journals Glycosylation of Capsaicin Derivatives and Phenylpropanoid Derivatives Using Cultured Plant Cells

2011 ◽  
Vol 4 ◽  
pp. BCI.S6682 ◽  
Author(s):  
Hisashi Katsuragi ◽  
Kei Shimoda ◽  
Ryohei Yamamoto ◽  
Kohji Ishihara ◽  
Hiroki Hamada
Keyword(s):  
Ferulic Acid ◽  
Caffeic Acid ◽  
Cinnamic Acid ◽  
Time Course ◽  
Cultured Cells ◽  
Plant Cells ◽  
Coumaric Acid ◽  
Reaction Products ◽  
Phenolic Group ◽  
Time Course Study

Biotransformations of capsaicinoids such as capsaicin and 8-nordihydrocapsaicin and phenylpropanoids such as cinnamic acid, p-coumaric acid, caffeic acid, and ferulic acid have been investigated using cultured plant cells. Capsain and 8-nordihydrocapsaicin were converted into the corresponding glycosides which are three glycosides respectively using the cultured cells of Catharanthus roseus. In a time-course study under sterile conditions, the changes in amounts of their reaction products were determined. Furthermore phenypropanoid, such as cinnamic acid, p-coumaric acid, caffeic acid and ferulic acid have been biotransformed using the cultured cells of the Eucalyptus perriniana, and then cinnamic acid was converted into two glycosides. In addition, p-coumaric acid, caffeic acid and ferulic acid were converted into four, four and three glycosides respectively. Then in time-course study under sterile conditions, the change in amounts of their reaction products were determined. Finally it was found that the cultured plant cells have the ability to glycosylate the phenolic group of capsacinoids and phenylpropanoids regioselectively.

METABOLISM OF PHENYLPROPANOID COMPOUNDS IN SALVIA: II. BIOSYNTHESIS OF PHENOLIC CINNAMIC ACIDS

1959 ◽  
Vol 37 (1) ◽  
pp. 537-547 ◽  
Author(s):  
D. R. McCalla ◽  
A. C. Neish
Keyword(s):  
Caffeic Acid ◽  
Phenolic Acids ◽  
Cinnamic Acid ◽  
Shikimic Acid ◽  
Sinapic Acid ◽  
Coumaric Acid ◽  
Cinnamic Acids ◽  
Phenyllactic Acid ◽  
Salvia Splendens ◽  
Specific Activities

p-Coumaric, caffeic, ferulic, and sinapic acids were found to occur in Salvia splendens Sello in alkali-labile compounds of unknown constitution. A number of C14-labelled compounds were administered to leafy cuttings of salvia and these phenolic acids were isolated after a metabolic period of several hours and their specific activities measured. Cinnamic acid, dihydrocinnamic acid, L-phenylalanine, and (−)-phenyllactic acid were found to be good precursors of the phenolic acids. D-Phenylalanine, L-tyrosine, and (+)-phenyllactic acid were poor precursors. A kinetic study of the formation of the phenolic acids from L-phenylalanine-C14 gave data consistent with the view that p-coumaric acid → caffeic acid → ferulic acid → sinapic acid, and that these compounds can act as intermediates in lignification. Feeding of C14-labelled members of this series showed that salvia could convert any one to a more complex member of the series but not so readily to a simpler member. Caffeic acid-β-C14 was obtained from salvia after the feeding of L-phenylalanine-β-C14 or cinnamic acid-β-C14, and caffeic acid labelled only in the ring was obtained after feeding generally labelled shikimic acid.

scholarly journals Identification of the Tyrosine- and Phenylalanine-Derived Soluble Metabolomes of Sorghum

2021 ◽  
Vol 12 ◽  
Author(s):  
Jeffrey P. Simpson ◽  
Jacob Olson ◽  
Brian Dilkes ◽  
Clint Chapple
Keyword(s):  
Amino Acids ◽  
Cinnamic Acid ◽  
Aromatic Amino Acids ◽  
Flavonoid Glycosides ◽  
Coumaric Acid ◽  
Biotic And Abiotic Stress ◽  
Proportional Contribution ◽  
Negative Ionization ◽  
Derivatives Of

The synthesis of small organic molecules, known as specialized or secondary metabolites, is one mechanism by which plants resist and tolerate biotic and abiotic stress. Many specialized metabolites are derived from the aromatic amino acids phenylalanine (Phe) and tyrosine (Tyr). In addition, the improved characterization of compounds derived from these amino acids could inform strategies for developing crops with greater resilience and improved traits for the biorefinery. Sorghum and other grasses possess phenylalanine ammonia-lyase (PAL) enzymes that generate cinnamic acid from Phe and bifunctional phenylalanine/tyrosine ammonia-lyase (PTAL) enzymes that generate cinnamic acid and p-coumaric acid from Phe and Tyr, respectively. Cinnamic acid can, in turn, be converted into p-coumaric acid by cinnamate 4-hydroxylase. Thus, Phe and Tyr are both precursors of common downstream products. Not all derivatives of Phe and Tyr are shared, however, and each can act as a precursor for unique metabolites. In this study, 13C isotopic-labeled precursors and the recently developed Precursor of Origin Determination in Untargeted Metabolomics (PODIUM) mass spectrometry (MS) analytical pipeline were used to identify over 600 MS features derived from Phe and Tyr in sorghum. These features comprised 20% of the MS signal collected by reverse-phase chromatography and detected through negative-ionization. Ninety percent of the labeled mass features were derived from both Phe and Tyr, although the proportional contribution of each precursor varied. In addition, the relative incorporation of Phe and Tyr varied between metabolites and tissues, suggesting the existence of multiple pools of p-coumaric acid that are fed by the two amino acids. Furthermore, Phe incorporation was greater for many known hydroxycinnamate esters and flavonoid glycosides. In contrast, mass features derived exclusively from Tyr were the most abundant in every tissue. The Phe- and Tyr-derived metabolite library was also utilized to retrospectively annotate soluble MS features in two brown midrib mutants (bmr6 and bmr12) identifying several MS features that change significantly in each mutant.

scholarly journals The effect of coffee beans roasting on its chemical composition

10.5219/1062 ◽  
2019 ◽  
Vol 13 (1) ◽  
pp. 344-350 ◽  
Author(s):  
Pavel Diviš ◽  
Jaromír Pořízka ◽  
Jakub Kříkala
Keyword(s):  
Acetic Acid ◽  
Lactic Acid ◽  
Formic Acid ◽  
Chlorogenic Acid ◽  
Total Phenolic ◽  
Coffee Beans ◽  
Aroma Characteristics ◽  
Phenolic Substances ◽  
Almost All ◽  
Coffee Cultivation

Drinking coffee has become part of our everyday culture. Coffee cultivation is devoted to over 50 countries in the world, located between latitudes 25 degrees North and 30 degrees South. Almost all of the world's coffee production is provided by two varieties, called ‘Arabica’ and ‘Robusta’ whereas the share of Arabica is 70% of the world's coffee harvest. Green (raw) coffee can not be used to prepare coffee beverages, coffee beans must first be roasted. Roasting coffee and reaching a certain degree of coffee roasting determine its flavor and aroma characteristics. In the present study the fate of sucrose, chlorogenic acid, acetic acid, formic acid, lactic acid, caffeic acid, total phenolic compounds and 5-hydroxymethylfurfural was studied in coffee (Brazil Cerrado Dulce, 100% Arabica) roasted in two ways (Medium roast and Full city roast). It has been found that almost all sucrose has been degraded (96 – 98%) in both roasting ways. During Medium roast 65% of chlorogenic acid contained in green coffee was degraded while during Full city roast it was 85%. During both Medium and Full city roasting, the formation of acetic acid but especially formic and lactic acid was recorded. The highest concentration of organic acids was recorded at Full City roasting at medium roasting times (3.3 mg.g-1 d.w. acetic acid, 1.79 mg.g-1 d.w. formic  acid, 0.65 mg.g-1d.w. lactic acid). The amount of phenolic substances also increased during roasting up to 16.7 mg.g-1 d.w. of gallic acid equivalent. Highest concentrations of 5-hydroxymethylfurfural were measured at medium roasting times at both Medium (0.357 mg.g-1 d.w.) and French city (0.597 mg.g-1 d.w.) roasting temperatures. At the end of roasting, the 5-hydroxymethylfurfural concentration in coffee were 0.237 mg.g-1 d.w. (Medium roast) and 0.095 mg.g-1 d.w. (Full city roast).

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