AROMATIC METABOLISM IN PLANTS: V. THE BIOSYNTHESIS OF CHLOROGENIC ACID AND LIGNIN IN POTATO CELL CULTURES

1967 ◽  
Vol 45 (9) ◽  
pp. 1451-1457 ◽  
Author(s):  
Oluf L. Gamborg
Keyword(s):  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Aromatic Compounds ◽  
Shikimic Acid ◽  
Quinic Acid ◽  
Insoluble Fraction ◽  
Klason Lignin ◽  
Coumaric Acid ◽  
Insoluble Material ◽  
Potato Cell

Studies were made on the biosynthesis of chlorogenic acid and on lignin formation in potato cells from suspension cultures. The cells were incubated with14C-labelled compounds, and the degree of incorporation into chlorogenic acid and into lignin were measured. Shikimic acid and quinic acid were not readily absorbed by the cells, whereas cinnamic acid, p-coumaric acid, and caffeic acid were absorbed very quickly. The results show that quinic acid and caffeic acid can serve as direct precursors of chlorogenic acid in the cells. A large proportion of the14C from the aromatic compounds was incorporated into the alcohol-insoluble fraction, and was associated with a Klason lignin. The lignin aldehydes obtained after nitrobenzene oxidation of the alcohol-insoluble material consisted of p-hydroxybenzaldehyde, vanillin, and trace amounts of syringaldehyde.

TOBACCO POLYPHENOLS: II. ON THE BIOSYNTHESIS OF CHLOROGENIC ACID

1963 ◽  
Vol 41 (11) ◽  
pp. 2249-2258 ◽  
Author(s):  
V. C. Runeckles
Keyword(s):  
Potato Tuber ◽  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Quinic Acid ◽  
Acid Synthesis ◽  
Coumaric Acid ◽  
Acid Biosynthesis ◽  
Tuber Tissue ◽  
Potato Tuber Tissue ◽  
Leaf Disks

Leaf disks of Nicotiana tabacum var. Delcrest were supplied with α-C14-labelled cinnamic, p-coumaric, and caffeic acids, p-coumaroyl-quinic acid, and the 1-glucose esters of cinnamic and p-coumaric acids. Considerable incorporation of radioactivity into chlorogenic acid occurred in 40 hours from all substrates except caffeic acid. In particular, p-coumaric acid was found to be a good precursor of chlorogenic acid in contrast to the findings of other workers with potato tuber tissue. More p-coumaric acid than cinnamic acid is converted to chlorogenic acid, although the reverse holds for conversion to p-coumaroyl-quinic acid. Chlorogenic acid synthesis from caffeic acid involves breakdown and resynthesis of the acid supplied, leading to the incorporation of radioactivity into other positions in the caffeic acid molecule and into the quinic acid moiety. Cinnamic and p-coumaric acids, on the other hand, are incorporated essentially intact into both p-coumaroyl-quinic and chlorogenic acids. These findings are discussed in relation to the pathway of chlorogenic acid biosynthesis postulated for potato tuber tissue.

TOBACCO POLYPHENOLS: II. ON THE BIOSYNTHESIS OF CHLOROGENIC ACID

1963 ◽  
Vol 41 (1) ◽  
pp. 2249-2258 ◽  
Author(s):  
V. C. Runeckles
Keyword(s):  
Potato Tuber ◽  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Quinic Acid ◽  
Acid Synthesis ◽  
Coumaric Acid ◽  
Acid Biosynthesis ◽  
Tuber Tissue ◽  
Potato Tuber Tissue ◽  
Leaf Disks

Leaf disks of Nicotiana tabacum var. Delcrest were supplied with α-C14-labelled cinnamic, p-coumaric, and caffeic acids, p-coumaroyl-quinic acid, and the 1-glucose esters of cinnamic and p-coumaric acids. Considerable incorporation of radioactivity into chlorogenic acid occurred in 40 hours from all substrates except caffeic acid. In particular, p-coumaric acid was found to be a good precursor of chlorogenic acid in contrast to the findings of other workers with potato tuber tissue. More p-coumaric acid than cinnamic acid is converted to chlorogenic acid, although the reverse holds for conversion to p-coumaroyl-quinic acid. Chlorogenic acid synthesis from caffeic acid involves breakdown and resynthesis of the acid supplied, leading to the incorporation of radioactivity into other positions in the caffeic acid molecule and into the quinic acid moiety. Cinnamic and p-coumaric acids, on the other hand, are incorporated essentially intact into both p-coumaroyl-quinic and chlorogenic acids. These findings are discussed in relation to the pathway of chlorogenic acid biosynthesis postulated for potato tuber tissue.

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 Natural Products from Scorzonera aristata (Asteraceae)

2010 ◽  
Vol 5 (5) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Manuela Jehle ◽  
Johanna Bano ◽  
Ernst P. Ellmerer ◽  
Christian Zidorn
Keyword(s):  
Natural Products ◽  
Methyl Ester ◽  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Acid Methyl Ester ◽  
Quinic Acid ◽  
The South ◽  
Caffeic Acid Derivatives ◽  
Aerial Parts ◽  
Acid Methyl

The aerial parts of Scorzonera aristata Ramond ex DC., collected in the South Tyrolean Dolomites, yielded the flavonoids quercetin 3- O-glucoside, rutin, and isoorientin, and the caffeic acid derivatives chlorogenic acid, 4,5-dicaffeoyl quinic acid, and 3,5-dicaffeoyl quinic acid. Sub-aerial parts contained caffeic acid methyl ester, 3,5-dicaffeoyl quinic acid, and the triterpenes 3α-hydroxyolean-5-ene, lupeol, and magnificol. Chemosystematic implications of the isolated compounds are discussed briefly.

scholarly journals Integrated Analysis of the Transcriptome and Metabolome of Cecropia obtusifolia: A Plant with High Chlorogenic Acid Content Traditionally Used to Treat Diabetes Mellitus

2020 ◽  
Vol 21 (20) ◽  
pp. 7572
Author(s):  
Jorge David Cadena-Zamudio ◽  
Pilar Nicasio-Torres ◽  
Juan Luis Monribot-Villanueva ◽  
José Antonio Guerrero-Analco ◽  
Enrique Ibarra-Laclette
Keyword(s):  
Diabetes Mellitus ◽  
Chlorogenic Acid ◽  
High Performance ◽  
Time Course ◽  
Shikimic Acid ◽  
Quinic Acid ◽  
Integrated Analysis ◽  
Cecropia Obtusifolia ◽  
Key Enzyme

This investigation cultured Cecropia obtusifolia cells in suspension to evaluate the effect of nitrate deficiency on the growth and production of chlorogenic acid (CGA), a secondary metabolite with hypoglycemic and hypolipidemic activity that acts directly on type 2 diabetes mellitus. Using cell cultures in suspension, a kinetics time course was established with six time points and four total nitrate concentrations. The metabolites of interest were quantified by high-performance liquid chromatography (HPLC), and the metabolome was analyzed using directed and nondirected approaches. Finally, using RNA-seq methodology, the first transcript collection for C. obtusifolia was generated. HPLC analysis detected CGA at all sampling points, while metabolomic analysis confirmed the identity of CGA and of precursors involved in its biosynthesis. Transcriptome analysis identified differentially expressed genes and enzymes involved in the biosynthetic pathway of CGA. C. obtusifolia probably expresses a key enzyme with bifunctional activity, the hydroxycinnamoyl-CoA quinate hydroxycinnamoyl transferase and hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase (HQT/HCT), which recognizes shikimic acid or quinic acid as a substrate and incorporates either into one of the two routes responsible for CGA biosynthesis.

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 Synthesis of hydroxycinnamoyl shikimates and their role in monolignol biosynthesis

Holzforschung ◽  
2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Dharshana Padmakshan ◽  
Vitaliy I. Timokhin ◽  
Fachuang Lu ◽  
Paul F. Schatz ◽  
Ruben Vanholme ◽  
...  
Keyword(s):  
Substrate Specificity ◽  
Caffeic Acid ◽  
Biosynthetic Pathway ◽  
Shikimic Acid ◽  
Sinapic Acid ◽  
Enzyme Characterization ◽  
Hydroxycinnamic Acids ◽  
Coumaric Acid ◽  
Monolignol Biosynthesis

Abstract Hydroxycinnamoyl shikimates were reported in 2005 to be intermediates in monolignol biosynthesis. 3-Hydroxylation of p-coumarate, originally thought to occur via coumarate 3-hydroxylase (C3H) from p-coumaric acid or its CoA thioester, was revealed to be via the action of coumaroyl shikimate 3′-hydroxylase (C3′H) utilizing p-coumaroyl shikimate as the substrate, itself derived from p-coumaroyl-CoA via hydroxycinnamoyl-CoA: shikimate hydroxycinnamoyltransferase (HCT). The same HCT was conjectured to convert the product, caffeoyl shikimate, to caffeoyl-CoA to continue on the pathway starting with its 3-O-methylation. At least in some plants, however, a more recently discovered caffeoyl shikimate esterase (CSE) enzyme hydrolyzes caffeoyl shikimate to caffeic acid from which it must again produce its CoA thioester to continue on the monolignol biosynthetic pathway. HCT and CSE are therefore monolignol biosynthetic pathway enzymes that have provided new opportunities to misregulate lignification. To facilitate studies into the action and substrate specificity of C3H/C3′H, HCT, and CSE enzymes, as well as for metabolite authentication and for enzyme characterization, including kinetics, a source of authentic substrates and products was required. A synthetic scheme starting from commercially available shikimic acid and the four key hydroxycinnamic acids (p-coumaric, caffeic, ferulic, and sinapic acid) has been developed to provide this set of hydroxycinnamoyl shikimates for researchers.

Dietary chlorogenic acid supplementation affects gut morphology, antioxidant capacity and intestinal selected bacterial populations in weaned piglets

2018 ◽  
Vol 9 (9) ◽  
pp. 4968-4978 ◽  
Author(s):  
Yong Zhang ◽  
Yu Wang ◽  
Daiwen Chen ◽  
Bing Yu ◽  
Ping Zheng ◽  
...  
Keyword(s):  
Antioxidant Capacity ◽  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Phenolic Acids ◽  
Quinic Acid ◽  
Weaned Piglets ◽  
Gut Morphology ◽  
Bacterial Populations ◽  
Acid Supplementation

Chlorogenic acid (CGA), an ester formed between caffeic acid and quinic acid, is one of the most abundant phenolic acids in plants.

scholarly journals Caffeic acid: a brief overview of its presence, metabolism, and bioactivity

2020 ◽  
Vol 3 (4) ◽  
pp. 74 ◽  
Author(s):  
Anna Birková
Keyword(s):  
Oxidative Stress ◽  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Acid Ester ◽  
Antioxidant Properties ◽  
Quinic Acid ◽  
Bioactive Compound ◽  
Common Phenomenon ◽  
Bioactive Substances ◽  
Naturally Occurring

Caffeic acid is a bioactive compound found in a variety of plants including vegetables, fruits, herbs, and drinks. It belongs to the huge group of chemicals called polyphenols and is a major representative of the polyphenol subgroup of hydroxycinnamic acids. In foods, caffeic acid occurs mostly as a quinic acid ester called chlorogenic acid. Caffeic acid, like other polyphenols, is believed to exhibit many health benefits associated with their antioxidant properties, including the prevention of inflammation, cancer, neurodegenerative diseases, and diabetes. Nowadays, the use of naturally occurring bioactive substances, including caffeic acid, is becoming a very common phenomenon. Thus, information about their functions and properties is very important.Keywords: caffeic acid, polyphenols, bioactive compound, oxidative stress

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