Further Investigations on the Chemistry of Fulvic Acid, a Soil Humic Fraction

1971 ◽  
Vol 49 (13) ◽  
pp. 2302-2309 ◽  
Author(s):  
S. U. Khan ◽  
M. Schnitzer
Keyword(s):  
Fatty Acids ◽  
Hydrogen Bonds ◽  
Fulvic Acid ◽  
Phenolic Acids ◽  
Complex Structures ◽  
Isolation And Identification ◽  
Fractionation Scheme ◽  
Humic Fraction ◽  
Benzenecarboxylic Acids

The fractionation scheme described in this and in an earlier paper resulted in the isolation and identification of about 2.0 g of pure components from 100 g of fulvic acid. About 28% of these compounds were phenolic acids, 19% benzenecarboxylic acids, 13% alkanes and fatty acids, and 40% dialkyl phthalates. The isolation of appreciable amounts of dialkyl phthalates was somewhat surprising but their presence was shown not be an artifact. The KMnO4 oxidation of the same fractions increased the yields of methylated phenolic and benzenecarboxylic acids by between 3 and 11 times.Following KMnO4 oxidation of methylated but unfractioned fulvic acid, the yield of phenolic and benzenecarboxylic acids increased substantially. The increased yields, after oxidation, of the same compounds as those that were separated without oxidation indicate that either these compounds originated from more complex structures or that they came from a structure of the type proposed earlier, which consists of phenolic and benzenecarboxylic acids joined by hydrogen-bonds, on which alkanes, fatty acids, and dialkyl phthalates are adsorbed.

The Occurrence of Fatty Acids in Fulvic Acid, A Soil Humic Fraction

1970 ◽  
Vol 8 (3) ◽  
pp. 505-512 ◽  
Author(s):  
M. Schnitzer ◽  
G. Ogner
Keyword(s):  
Fatty Acids ◽  
Fulvic Acid ◽  
Humic Fraction

The Chemistry of High Molecular Weight Fulvic Acid Fractions

1974 ◽  
Vol 52 (24) ◽  
pp. 4123-4132 ◽  
Author(s):  
Jean A. Neyroud ◽  
Morris Schnitzer
Keyword(s):  
Fatty Acids ◽  
Molecular Weight ◽  
Ethyl Acetate ◽  
Fulvic Acid ◽  
Phenolic Acids ◽  
Degradation Products ◽  
Building Blocks ◽  
Oh Groups ◽  
Molecular Weights ◽  
Chemical Structures

Fulvic acid (FA) was methylated, dissolved in benzene, and fractionated over Al2O3 with the aid of organic solvents of increasing polarities. This paper is concerned with fractions eluted with ethyl acetate (III), ethyl acetate — methanol (1:1) (IV), and methanol (V), which were quantitatively the most abundant ones and which we consider as being most representative of the original FA. Each fraction was characterized by chemical and spectroscopic methods and by degradation with alkaline permanganate. Fractions IV and V were also degraded by NaOH hydrolysis and by alkaline CuO-oxidation. The degradation products were identified with the aid of a gas chromatograph — mass spectrometer — computer system.The number-average molecular weights of the three fractions were: III, 821; IV, 945; and V, 1,397. Infrared, proton n.m.r., and carbon-13 n.m.r. spectra provided, except for functional groups, little detailed information on the chemical structures of the fractions. The major degradation products were benzenecarboxylic and phenolic acids in addition to smaller amounts of aliphatic (mainly n-fatty) acids. Evidence is presented that may be interpreted to indicate: (a) esterification of some of the fatty acids to OH groups of phenolic acids; (b) the existence in the fractions of ether (C—O) linkages; and (c) rupture of C—C bonds during degradation. While in both the lower and the higher molecular weight FA fractions benzenecarboxylic and phenolic acids were the basic "building blocks", the latter appeared to be more complex and more stable in the higher-molecular weight fractions, possibly because chemical bonding as well as hydrogen bonding, van der Waal's forces, and π-bonding were involved simultaneously.

Chemistry of Fulvic Acid, a Soil Humic Fraction, and its Relation to Lignin

1971 ◽  
Vol 49 (7) ◽  
pp. 1053-1063 ◽  
Author(s):  
G. Ogner ◽  
M. Schnitzer
Keyword(s):  
Gas Chromatography ◽  
Hydrogen Bonding ◽  
Fulvic Acid ◽  
Water Soluble ◽  
Chromatographic Retention ◽  
Biological Oxidation ◽  
Polycarboxylic Acids ◽  
Preparative Gas Chromatography ◽  
Humic Fraction ◽  
Benzenecarboxylic Acids

Fulvic acid, a water-soluble soil humic fraction, was extracted from a Podzol soil and exhaustively methylated so as to make it soluble in benzene. The resulting material was separated repeatedly by column, thin layer, and preparative gas chromatography until relatively pure components were obtained. The latter were then identified by comparing their mass and micro-i.r. spectra and their gas chromatographic retention times with those of standards of known structures.Twenty-one phenolic and benzene-carboxylic acids were identified as methyl ethers and esters. In addition, a number of polymethoxy-benzene polycarboxylic acids of as yet unknown identity were isolated.A number of the compounds isolated have been reported to arise from the alkaline KMnO4 oxidation of lignin. Since we did not oxidize the fulvic acid in the laboratory, it is likely that it originated from products resulting from the chemical and/or biological oxidation of lignin in the soil. Methylation of the fulvic acid was necessary to make the compounds extractable by organic solvents. Since methylation reduces hydrogen-bonding in the fulvic acid, it is suggested that in fulvic acid phenolic and benzenecarboxylic acids are joined by hydrogen-bonds to form a polymeric structure of yet unknown conformation. Any weakening of hydrogen-bonding will lead to a break-up of this structure.

PHYTOCHEMICAL SCREENING, ANTIOXIDANT, ANTI-CYTOTOXIC AND ANTICANCER EFFECTS OF GALINSOGA PARVIFLORA AND VERNONIA POLYANTHES (ASTERACEAE) EXTRACTS

2020 ◽  
Vol 8 (10) ◽  
pp. 84-98
Author(s):  
Sula M. V. Feleti ◽  
Renê L. Aleluia ◽  
Suiany V. Gervásio ◽  
Jean Carlos V. Dutra ◽  
Jessica R. P. Oliveira ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Phenolic Acids ◽  
Unsaturated Fatty Acids ◽  
Biological Effects ◽  
Human Lymphocytes ◽  
Chemical Characterization ◽  
Total Content ◽  
Ags Cells ◽  
Ft Icr Ms ◽  
Ft Icr

The study was designed to investigate the chemical composition and the biological effects of G. parviflora and V. polyanthes ethanolic extracts in vitro. Total content of phenols, flavonoids and tannins was quantified by spectrophotometry; chemical characterization was permed by mass spectrometry (ESI (-) FT-ICR MS and APCI (+) FT-ICR MS analysis). Antioxidant activities were determined by FRAP and Fe2+ chelating methods. Extracts cytotoxicity was evaluated in human lymphocytes, sarcoma-180 (S-180) and human gastric adenocarcinoma (AGS) cells, by MTT assay. V. polyanthes presented higher total content of tannins and G. parviflora presented higher amount of phenols and flavonoids. Chemical characterization showed the presence of flavonoids, phenolic acids and sesquiterpene lactones in V. polyanthes extract, and steroids, phenolic acids and fatty acids (Poly Unsaturated Fatty Acids - PUFA) in G. parviflora extract. V. polyanthes extract stood out in the Fe2+ chelation test. G. parviflora extract did not present outstanding antioxidant results in the tested protocols. Both species showed a tendency to promote cytotoxicity in human lymphocyte cells. Regarding the antiproliferative effect, both species were able to reduce S-180 cell viability and G. parviflora extract showed high antiproliferative potential in the assay with AGS cells. These findings reinforce the medicinal use of these plants, as well as suggest their potential use for the development of new drugs and for the treatment of cancers.

Isolation and identification of C-19 fatty acids with anti-tumor activity from the spores of Ganoderma lucidum (reishi mushroom)

Fitoterapia ◽  
2012 ◽  
Vol 83 (3) ◽  
pp. 490-499 ◽  
Author(s):  
Pei Gao ◽  
Tomoya Hirano ◽  
Zhiqing Chen ◽  
Tadashi Yasuhara ◽  
Yoshihiro Nakata ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Ganoderma Lucidum ◽  
Isolation And Identification ◽  
Anti Tumor Activity

Isolation and Identification of Lipolytic Microorganisms Found on Rough Rice from Two Growing Areas

1978 ◽  
Vol 41 (1) ◽  
pp. 28-30 ◽  
Author(s):  
ANTHONY J. DeLUCCA ◽  
STEPHEN J. PLATING ◽  
ROBERT L. ORY
Keyword(s):  
Fatty Acids ◽  
Brown Rice ◽  
Plate Count ◽  
Isolation And Identification ◽  
Lipolytic Action ◽  
Rough Rice ◽  
Colony Forming Units ◽  
Rice Samples ◽  
Lipolytic Microorganisms ◽  
Rice Oil

Rice bran and whole brown rice are currently underutilized because free fatty acids are formed from rice oil during storage. Rough rice from two growing areas was tested for presence of lipolytic microorganisms that could release these fatty acids. Approximately 10% of the total bacterial plate count (4 × 106/g for Louisiana and 12 × 106/g for the Arkansas rice samples) were lipolytic. Upon testing, most were classified as nonsaccharolytic, alkali-producing pseudomonads. The average mold plate count for the Louisiana sample was 2 × 103 colony forming units (cfu)/g and 5 × 103 cfu/g for the Arkansas sample. All molds isolated showed various amounts of lipolytic action, as determined by the size of the lipolytic zone. The molds were generally isolated more from the Louisiana than from the Arkansas rice. Alternaria and Helminthosporium species, the most prevalent molds, were found in all samples.

scholarly journals Bioactive Compounds in Sarcocornia and Arthrocnemum, Two Wild Halophilic Genera from the Iberian Peninsula

Plants ◽  
2021 ◽  
Vol 10 (10) ◽  
pp. 2218
Author(s):  
Irene Sánchez-Gavilán ◽  
Esteban Ramírez Chueca ◽  
Vicenta de la Fuente García
Keyword(s):  
Fatty Acids ◽  
Salt Tolerance ◽  
Ferulic Acid ◽  
Iberian Peninsula ◽  
Bioactive Compounds ◽  
Phenolic Acids ◽  
Coastal Marshes ◽  
Esi Ms ◽  
Tinto River ◽  
High Diversity

(1) Background: this study describes bioactive compounds in the following halophytes: Sarcocornia (S. alpini, S. pruinosa, and S. perennis) and Arthrocnemum (A. macrostachyum). The material comes from: coastal marshes in Tinto River, Guadiana River, and some interior provinces from the Iberian Peninsula. (2) Methods: the techniques used were Folin–Ciocalteu, GC-MS, and ESI-MS/MS. (3) Results: Five phenolic acids were found in Sarcocornia: trans-cinnamic, salicylic, veratric, coumaric, and caffeic acids. In addition, in Arthronemum, ferulic acid was also detected. The obtained flavonoids were cyanidin-3-O-arabinoside, luteolin-7-glucoside, dihydroquercetin, and p-coumaroyl-glucoside. They also presented fatty acids, such as palmitic, linoleic, and oleic acids in Sarcocornia, while palmitic, linolenic, and stearic acids were the main fatty acids in A. macrostachyum. (4) Conclusions: the high diversity of the compounds identified confirms the relation between nutritional interest and salt tolerance in halophytes.

scholarly journals Ability of phenolic acids to protect naturally present alfa-tocopherol during the heating of plant oils  

2012 ◽  
Vol 30 (No. 4) ◽  
pp. 351-357 ◽  
Author(s):  
Z. Réblová ◽  
J. Fišnar ◽  
D. Tichovská ◽  
M. Doležal ◽  
K. Joudalová
Keyword(s):  
Fatty Acids ◽  
Antioxidant Activity ◽  
Phenolic Acids ◽  
Sunflower Oil ◽  
Phenolic Acid ◽  
Half Life ◽  
Tocopherol Content ◽  
Plant Oils ◽  
Hot Plate ◽  
Experimental Conditions

The ability of phenolic acids (ferulic, gallic, protocatechuic, and sinapic; 600 mg/kg) to protect naturally present a-tocopherol was tested during the heating of sunflower oil on a hot plate set at 120, 150, 180, 210, or 240°C, and during the heating of rapeseed, olive and soybean oils on a hot plate set at 180°C. In all the studied conditions, a-tocopherol was significantly protected only by gallic acid. This phenolic acid prolonged the half-life of a-tocopherol (calculated as the time needed for the a-tocopherol content to decrease to 50% of the original value) typically two- to four-fold. Hence the ability of phenolic acids to protect a-tocopherol in bulk oils does not markedly depend on the experimental conditions as is seen in antioxidant activity, i.e. in the ability of antioxidants to protect fatty acids.  

scholarly journals Role of caffeic and chlorogenic acid in the modulation of cellular fatty acid uptake

2020 ◽  
Vol 79 (OCE2) ◽  
Author(s):  
Mirko Marino ◽  
Massimiliano Tucci ◽  
Valentina Taverniti ◽  
Patrizia Riso ◽  
Marisa Porrini ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Chlorogenic Acid ◽  
Phenolic Acids ◽  
Lipid Accumulation ◽  
Biological Activities ◽  
Fatty Acid Uptake ◽  
Cellular Fatty Acid ◽  
Bioactive Molecules ◽  
Acid Uptake

AbstractPolyphenols are bioactive molecules widely distributed in numerous foods such as fruits, vegetables, tea, coffee, cocoa and beverages. Their main classification include flavonoids (i.e. flavonols, flavones, flavanones, flavanols, anthocyanins, and isoflavones), non-flavonoids (i.e. lignans and stilbens) and phenolic acids (i.e. hydroxycinnamic and hydroxybenzoic acids)(1). Caffeic acid (CA) and chlorogenic acid (CGA; an ester of CA and quinic acid) are the major representatives of hydroxycinnamic acids. Accumulating evidence has demonstrated that CA and CGA may exert different biological activities, including antioxidant, anti-inflammatory, antidiabetic, and antihypertensive(2). Despite these promising and diverse anti-atherosclerotic actions, investigations addressing the effect of CA and CGA on atherogenesis are scarce.The present study evaluated the capacity of CA and CGA to reduce lipid accumulation in macrophages derived from monocytic THP-1 cells. THP-1-derived macrophages were incubated with fatty acids (500 μM oleic/palmitic acid, 2:1 ratio) and different concentrations (from 0.03 to 3 μM) of CA and CGA, alone or in combination. Lipid accumulation was quantified spectrophotometrically (excitation: 544 nm, emission: 590 nm) with the fluorescent dye, Nile red. The fold increase compared to the control (without fatty acids) was calculated. In addition, the expression of several transcription factors including peroxisome proliferator-activated receptor gamma (PPARγ) and CCAAT/enhancer-binding protein (CEBP), as potential mechanisms involved in the regulation of lipid accumulation, was evaluated by real time PCR.Analysis of variance (ANOVA) was used to assess the effect of the different concentrations of CA and CGA on lipid accumulation in THP-1 macrophages following stimulation with FA.The preliminary results obtained have shown a significant increase in lipid accumulation following fatty acid exposure (p < 0.0001). Incubation with CA and CGA did not reduce lipid accumulation in THP-1 derived macrophages, while the combination of CA + CGA at 0.03, 0.3 and 3 μM (p < 0.01) decreased cellular fatty acid uptake at all concentrations tested by -28%, -32%, -23%, respectively. An apparent modulation of the transcriptional activity of PPARγ, but not CEBP, was observed following the combination of phenolic acids.In conclusion, the incubation of CA + CGA at physiologically relevant concentrations, but not the single compounds, seem to reduce the uptake of fatty acids in THP-1-derived macrophages. Further experiments are ongoing in order to confirm the findings obtained and to better identify the mechanisms of action involved in the reduction of lipid accumulation as a key phenomenon of atherogenesis.

scholarly journals Collagen-Based Materials Modified by Phenolic Acids—A Review

Materials ◽  
2020 ◽  
Vol 13 (16) ◽  
pp. 3641
Author(s):  
Beata Kaczmarek ◽  
Olha Mazur
Keyword(s):  
Antimicrobial Activity ◽  
Hydrogen Bonds ◽  
Phenolic Acids ◽  
Biomedical Applications ◽  
Present Knowledge ◽  
Polymeric Chain ◽  
Mechanical Parameters ◽  
Research Reporting ◽  
Pure Collagen ◽  
Different Types

Collagen-based biomaterials constitute one of the most widely studied types of materials for biomedical applications. Low thermal and mechanical parameters are the main disadvantages of such structures. Moreover, they present low stability in the case of degradation by collagenase. To improve the properties of collagen-based materials, different types of cross-linkers have been researched. In recent years, phenolic acids have been studied as collagen modifiers. Mainly, tannic acid has been tested for collagen modification as it interacts with a polymeric chain by strong hydrogen bonds. When compared to pure collagen, such complexes show both antimicrobial activity and improved physicochemical properties. Less research reporting on other phenolic acids has been published. This review is a summary of the present knowledge about phenolic acids (e.g., tannic, ferulic, gallic, and caffeic acid) application as collagen cross-linkers. The studies concerning collagen-based materials with phenolic acids are summarized and discussed.

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