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PubMed1980

Metabolism and macromolecular binding of carcinogenic and noncarcinogenic metabolites of benzo(a)pyrene by hamster embryo cells.

The metabolism and macromolecular binding of four metabolites of benzo(a)pyrene in hamster embryo fibroblasts has been studied. Two noncarcinogenic phenolic derivatives, 3-hydroxybenz(a)pyrene and 9-hydroxybenzo(a)pyrene, are rapidly metabolized, primarily to their respective glucuronic acid conjugates and other H2O-soluble conjugates (78.4 to 80.8% of total radioactivity). Water-soluble conjugates were also formed from the carcinogenic phenol, 2-hydroxybenzo(a)pyrene, and from 7,8-dihydro-7,8-dihydroxybenzo(a)pyrene, but in lower amounts (36.8 to 43.8% of total radioactivity. With each of the compounds, from 10 to 20% of the radioactivity was converted to ethyl acetate-soluble metabolites. The amount of unmetabolized 2-hydroxybenzo(a)pyrene recovered intracellularly was 20-fold higher than that recovered in incubations with the other phenols. Covalent binding to nuclear macromolecules was monitored after isopyknic separation. Binding of the three phenols tested was similar and was lower than the binding of benzo(a)pyrene to nuclear DNA, RNA, and protein. In contrast to the results with the monohydroxybenzo(a)pyrenes, high levels of covalent binding were observed with 7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene; binding to DNA was 8-fold higher (315 pmol bound per mg DNA) than binding of benzo(a)pyrene to DNA.

Animals↗
PubMed1976

Metabolism of benzo(a)pyrene and benzo (a)pyrene derivatives to mutagenic products by highly purified hepatic microsomal enzymes.

A highly purified and reconstituted hepatic microsomal monooxygenase system, completely free of epoxide hydrase and consisting of cytochrome P-448 from 3-methylcholanthrene-treated rats, NADPH-cytochrome c reductase, phosphatidylcholine, and NADPH, metabolizes benzo (a)pyrene to products highly mutagenic in strains TA 98 and TA 1538 of Salmonella typhimurium. The formation of mutagenic metabolites is completely dependent on the presence of benzo (a)pyrene, NADPH, NADPH-cytochrome c reductase, and cytochrome P-448 and is partially dependent on phosphatidylcholine. Mutation frequency in both strains is linearly related to amount of cytochrome P-448 and to time of incubation. Highly purified cytochrome P-450 from phenobarbital-treated rats is relatively poor in catalyzing the formation of mutagenic metabolites from benzo (a)pyrene. Addition of 7.5 to 75 units of highly purified epoxide hydrase to the cytochrome P-448-dependent monooxygenase system decreases the number of mutations by approximately 50% and30% in strains TA 1538 and TA 98, respectively. Additional amounts of epoxide hydrase (300 units) fail to further suppress mutations, indicating that at least some, but probably not all, of the mutagenic metabolites of benzo (a)pyrene are arene oxides. In the absence of a monooxygenase system, mutations induced by benzo (a)pyrene 4,5-oxide are readily quenched by epoxide hydrase, whereas mutations induced by a diol epoxide metabolite of benzo (a)pyrene [(+/-)-7 beta, 8alpha-dihydroxy-9beta, 10beta-epoxy-7,8,9,10-tetrahydrobenzo (a)pyrene] are not. Several known and potential phenolic and dihydrodiol metabolites of benzo (a)pyrene are metabolized to products mutagenic in the Salmonella. The number of mutations induced per nmol of hemoprotein is approximately 3- to 4-fold higher when trans-7,8-dihydroxy-7,8-dihydrobenzo (a)pyrene replaces benzo (a)pyrene as a substrate for the cytochrome P-448-dependent monooxygenase system. Little or no mutagenic activity is observed with trans-dihydrodiols at positions 4,5, 9,10, or 11,12 of the hydrocarbon, either in the absence or presence of the active monooxygenase system. Of the 12 possible isomeric monophenols of benzo (a)-pyrene, only 6- and 12-hydroxybenzo (a)pyrene are moderately active bacterial mutagens; 1-, 2-, 3-, 6-, 9-, and 12-hydroxybenzo (a)pyrene are premutagens (i.e. metabolized to mutagenic products); and 4-, 5-, 7-, 8-, 10-, and 11-hydroxybenzo (a)pyrene have little or no mutagenic activity with or without further oxidative metabolism. Benzo (a)pyrene 7,8-oxide, a carcinogen on mouse skin, is weakly mutagenic but can be further metabolized to a highly active bacterial mutagen(s), presumably diol epoxide(s), by a combination of epoxide hydrase and the cytochrome P-448 monooxygenase system. This is the first example of a direct role of epoxide hydrase in the metabolic activation of a chemical to a toxic product.

Animals↗
PubMed1992

Utilization of methoxylated benzoates and formation of intermediates by Desulfotomaculum thermobenzoicum in the presence or absence of sulfate.

Desulfotomaculum thermobenzoicum strain TSB (DSM 6193) was found to utilize some methoxylated benzoates as carbon and energy source with or without sulfate. 3- or 4-Methoxybenzoate, vanillate (4-hydroxy-3-methoxybenzoate), syringate (3,5-dimethoxy-4-hydroxybenzoate) and 3,4,5-trimethoxybenzoate were converted to corresponding hydroxybenzoates. However, neither 2-methoxybenzoate nor 2,6-dimethoxybenzoate was utilized. The organism grew acetogenically on each of the methoxylated benzoates in the absence of sulfate. 3,4-Dihydroxy-5-methoxybenzoate was detected during conversion of syringate, and syringate and 3,4-dihydroxy-5-methoxybenzoate were detected during conversion of 3,4,5-trimethoxybenzoate as intermediates. These findings indicate that 4-methoxyl-group is most readily cleaved, whereas 2-methoxyl-group is not utilized by the organism.

Acetates↗
PubMed2001

Identification and effects of interaction phytotoxic compounds from exudate of Cistus ladanifer leaves.

Eleven allelochemicals (ferulic acid, cinnamic acid, 4-hydroxybenzoic acid, hydroxycinnamic acid, methyl propionate, oxalic acid, methylmalonic acid, p-anisic acid, butyric acid, 3-hydroxybutyric acid, and azulene) were identified in the exudate of Cistus ladanifer L. We studied the effect of each on germination, cotyledon emergence, root length, and cotyledon length of Rumex crispus. Three groups were distinguished with respect to phytotoxic activity: compounds with low activity (ferulic acid, 4-hydroxybenzoic acid, oxalic acid, methylmalonic acid, p-anisic acid, hydroxybutyric acid, and azulene), with intermediate activity (cinnamic acid and hydroxycinnamic acid), and with high activity (methyl propionate and butyric acid). The effect of the interaction of the compounds was studied. When acting conjointly, all combinations tested produced a more negative effect on both germination and seedling growth than when acting alone. The interaction affected cotyledon emergence and root length more negatively than germination and cotyledon length. When hydroxycinnamic acid and cinnamic acid were added to these mixtures there was an enhancement in the phytotoxic activity, accentuating the effect of the other allelochemicals.

3-Hydroxybutyric Acid↗
PubMed2002

The trans-anethole degradation pathway in an Arthrobacter sp.

A bacterial strain (TA13) capable of utilizing t-anethole as the sole carbon source was isolated from soil. The strain was identified as Arthrobacter aurescens based on its 16 S rRNA gene sequence. Key steps of the degradation pathway of t-anethole were identified by the use of t-anethole-blocked mutants and specific inducible enzymatic activities. In addition to t-anethole, strain TA13 is capable of utilizing anisic acid, anisaldehyde, and anisic alcohol as the sole carbon source. t-Anethole-blocked mutants were obtained following mutagenesis and penicillin enrichment. Some of these blocked mutants, accumulated in the presence of t-anethole quantitative amounts of t-anethole-diol, anisic acid, and 4,6-dicarboxy-2-pyrone and traces of anisic alcohol and anisaldehyde. Enzymatic activities induced by t-anethole included: 4-methoxybenzoate O-demethylase, p-hydroxybenzoate 3-hydroxylase, and protocatechuate-4,5-dioxygenase. These findings indicate that t-anethole is metabolized to protocatechuic acid through t-anethole-diol, anisaldehyde, anisic acid, and p-hydroxybenzoic acid. The protocatechuic acid is then cleaved by protocatechuate-4,5-dioxygenase to yield 2-hydroxy-4-carboxy muconate-semialdehyde. Results from inducible uptake ability and enzymatic assays indicate that at least three regulatory units are involved in the t-anethole degradation pathway. These findings provide new routes for environmental friendly production processes of valuable aromatic chemicals via bioconversion of phenylpropenoids.

Allylbenzene Derivatives↗
PubMed1980

[Various methods for the determination of preservatives in food. I. Extraction and spectrophotometric determinations (author's transl)].

In the Federal Republik of Germany formic acid, benzoic acid, propionic acid, sorbic acid and the esters of p-hydroxybenzoic acid were permitted as food-additives. They can be extracted together from acidified materials by means of perforation with ether. During distillation the preservatives are fixed by sodium hydroxide. The alkaline extract can then be used directly for various photometric (Part I) and chromatographic (Part II) determinations. All preservatives except propionic acid can be identified and determined by simple and specific color reaction. From the alkaline extract, benzoic acid, sorbic acid and the esters of p-hydroxybenzoic acid can be separated as the free acid by thin-layer chromatography on silica gel. Determination of the remission at 232 nm and 260 nm and of the reduction in fluorescence are employed for the photometric in situ evaluation of the thin-layer chromatograms.

Benzoates↗
PubMed1975

[V. The phenolics of strawberries and their changes during development and ripeness of the fruits (author's transl)].

16 strawberry varieties contained ca. 10--70 mg (+)-catechin per kg freshweight, frequently up to 10 mg (-)-epicatechin, seldom (+)-gallocatechin and never (-)-epigallocatechin. The phenolic contents after hydrolysis were up to ca. 10 mg caffeic acid, ca. 10--15 mg p-coumaric acid, ca. 10--35 mg 4-hydroxybenzoic acid, up to 6 mg protocatechuic acid and ca. 10--40 mg gallic acid per 1000 g freshweight. From "Senga Sengana" ca. 10 mg/kg methyl gallate and ellagic acid were isolated. Salicylic acid, gentisic acid and vanillic acid were found in traces (1 mg/kg). The concentrations of all the examined phenolic acids, relating to the whole fruit (mg per fruit) increased, and, relating to fresh weight (mg per kg) decreased during the growth of the fruits with exception of 4-hydroxybenzoic acid. This acid appeared only in a relatively late stage of the fruit. The changes in catechins were similar. In the ripe fruit the catechin level was reduced a little.

Benzopyrans↗
PubMed1991

Kelletinin I and kelletinin A from the marine mollusc Buccinulum corneum are inhibitors of eukaryotic DNA polymerase alpha.

The inhibitory effect of esters of p-hydroxybenzoic acid (kelletinins I and A), extracted from the marine gastropod Buccinulum corneum, have been tested on eukaryotic and prokaryotic enzymes of DNA metabolism such as DNA polymerases alpha and beta, DNA polymerase I, Exo III, pancreatic DNAse I, micrococcal DNAse and E. coli RNA polymerase. Kelletinin I and kelletinin A inhibit preferentially DNA polymerase alpha. The inhibitory effect of kelletinin I involves the hydroxyl group of p-hydroxybenzoic acid.

Animals↗
PubMed2005

Key enzymes of the protocatechuate branch of the beta-ketoadipate pathway for aromatic degradation in Corynebacterium glutamicum.

Although the protocatechuate branch of the beta-ketoadipate pathway in Gram+ bacteria has been well studied, this branch is less understood in Gram+ bacteria. In this study, Corynebacterium glutamicum was cultivated with protocatechuate, p-cresol, vanillate and 4-hydroxybenzoate as sole carbon and energy sources for growth. Enzymatic assays indicated that growing cells on these aromatic compounds exhibited protocatechuate 3,4-dioxygenase activities. Data-mining of the genome of this bacterium revealed that the genetic locus ncg12314-ncg12315 encoded a putative protocatechuate 3,4-dioxygenase. The genes, ncg12314 and ncg12315, were amplified by PCR technique and were cloned into plasmid (pET21aP34D). Recombinant Escherichia coli strain harboring this plasmid actively expressed protocatechuate 3,4-dioxygenase activity. Further, when this locus was disrupted in C. glutamicum, the ability to degrade and assimilate protocatechuate, p-cresol, vanillate or 4-hydroxybenzoate was lost and protocatechuate 3,4-dioxygenase activity was disappeared. The ability to grow with these aromatic compounds and protocatechuate 3,4-dioxygenase activity of C. glutamicum mutant could be restored by gene complementation. Thus, it is clear that the key enzyme for ring-cleavage, protocatechuate 3,4-dioxygenase, was encoded by ncg12314 and ncg12315. The additional genes involved in the protocatechuate branch of the beta-ketoadipate pathway were identified by mining the genome data publically available in the GenBank. The functional identification of genes and their unique organization in C. glutamicum provided new insight into the genetic diversity of aromatic compound degradation.

Adipates↗
PubMed1998

[Phenolic acid intake of adults in a Bavarian subgroup of the national food consumption survey].

Phenolic acids, essentially hydroxycinnamic acids and hydroxybenzoic acids, are secondary plant products and commonly found in plant derived foodstuff. The antioxidant and anticarcinogenic properties of phenolic acids could be one of the facts to explain the inverse association between fruit and vegetable intake and the incidence of coronary heart disease and cancer, respectively, as found in epidemiologic studies. Phenolic acids are rarely listed in food composition tables and there are no dietary intake data available. Consequently, a data base containing the phenolic acid content of foods (literatur data) was built and 7-d dietary protocols of 63 women and 56 men of a Bavarian subpopulation (age 19-49 years) of the German National Food Consumption Survey (NVS) were evaluated. The average phenolic acid intake of men and women is 222 mg/d within a large range. The dominating one within all the phenolic acids is clearly caffeic acid (206 mg/d); the intake of the other phenolic acids amounts to 0.2 (gentisic acid) up to 5.2 mg/d (ellagic acid). The sum of hydroxybenzoic acids and hydroxycinnamic acids amounts to 11 mg/d and 211 mg/d, respectively. Significant sex differences are found for some of the phenolic acids. Especially, the average intake of caffeic acid of women (229 mg/d) is higher than that of men (179 mg/d) caused by the high amount of coffee consumption. The age group "25-49 years" is consuming more coffee than the age group "19-24 years" and, therefore, reveals a significantly higher intake of caffeic acid. The major sources of phenolic acids are coffee with 92% of the caffeic acid intake and fruits (including fruit products and juices) with 75% of the salycilic acid and 59% of the p-coumaric acid intake. Consequently, phenolic acids are consumed in considerable amounts with food. Since antioxidant and anticarcinogenic properties of phenolic acids are already proven in in vitro as well as in animal experiments, epidemiologic studies will show whether a high phenolic acid intake goes ahead with a reduced risk for coronary heart disease or cancer in humans.

Acids, Carbocyclic↗
PubMed2006

Sedimenticola selenatireducens, gen. nov., sp. nov., an anaerobic selenate-respiring bacterium isolated from estuarine sediment.

The respiration of selenate, as a terminal electron acceptor has been known for over a decade, but the microorganisms involved in this respiration are largely unknown. Here we characterize a novel selenate-respiring bacterium, strain AK4OH1, isolated from an estuarine sediment enrichment culture. Strain AK4OH1 has the unique capability to oxidize aromatic acids, such as benzoate, 4-hydroxybenzoate and 3-hydroxybenzoate, coupled to selenate respiration. This novel respiratory coupling has not been described before. Reduction of selenate is followed by stoichiometric accumulation of selenite. The strain grows in agar shake tubes forming bright red colonies due to precipitation of elemental selenium. Strain AK4OH1 is a strictly anaerobic bacterium, which can also respire nitrate and nitrite via denitrification. Analysis of the 16S rRNA gene sequence shows that this strain clusters with another selenate-reducing bacterium and a (per) chlorate reducing bacterium, within the Gammaproteobacteria, along with symbionts of bivalves and tubeworms. Based on its unique physiological capabilities and its 16S rRNA gene sequence phylogeny, we classify this strain AK4OH1 as a new genus and species with the proposed name Sedimenticola selenatireducens.

Base Sequence↗
PubMed1997

Sensitivity to treatment with polyunsaturated fatty acids is a general characteristic of the ubiquinone-deficient yeast coq mutants.

The biosynthesis of ubiquinone (Q) and the functional consequences of Q-deficiency was studied in the yeast Saccharomyces cerevisiae. Lipid extracts were prepared from various respiratory deficient mutants grown in the presence of p-[U-14C]hydroxybenzoic acid. Q mutant strains harboring mutations in the coq3, coq4, coq5, coq6, coq7, or coq8 genes were unable to produce Q and accumulated an early intermediated that corresponded to 3-hexaprenyl-4-hydroxybenzoic acid. Several respiratory deficient yeast including both nuclear and mitochondrial petite mutant strains, retain the ability to produce Q. Thus, the inability to produce Q is a specific phenotype manifested in the class of mutants termed 'coq'. Previous studies described the enhanced sensitivity of the Q-deficient yeast strain containing a deletion in the COQ3 gene to the products of autoxidized polyunsaturated fatty acids (Do et al., 1996, Proceeding of the National Academy of Science USA, 93, 7534-7539). The results presented here show this to be a general phenotype resulting from Q-deficiency, as all of the coq mutant yeast strains tested exhibit hypersensitivity to polyunsaturated fatty acid treatment.

Electron Transport↗
PubMed2003

Hydrogen peroxide scavenging, antioxidant and anti-radical activity of some phenolic acids.

Some water-soluble phenolic acids were investigated as antioxidants, scavengers of hydrogen peroxide (H(2)O(2)) and scavengers of 1,1-diphenyl-2-picrylhydrazyl radical (DPPH(*)). The strongest antioxidant, scavenging of H(2)O(2) and DPPH(*) radical activity was exhibited by 3,4,5-trihydroxybenzoic (gallic) acid and 1,2,3-trihydroxybenzene (pyrogallol) with three hydroxyl groups bonded to the aromatic ring in an ortho position in relation to each other. Phenolic acids with two hydroxyl groups bonded to aromatic ring in the ortho position, such as 3,4-dihydroxycinnamic (caffeic), 3,4-dihydroxybenzoic (protocatechuic) and 2,3-dihydroxybenzoic (o-pyrocatechuic) acids, showed strong antioxidant and anti-radical activity; however, it was lower than that of 3,4,5-trihydroxybenzoic acid or 1,2,3-trihydroxybenzene. 3,5-Dihydroxybenzoic (alpha-resorcylic) and 2,4-dihydroxybenzoic (beta-resorcylic) acids with two hydroxyls bonded in the meta position in relation to each other showed moderate antioxidant and low DPPH(*) and hydrogen peroxide scavenging activity. Compounds with one hydroxyl group such as 3-hydroxybenzoic, 4-hydroxyphenylacetic and 2-hydroxybenzoic (salicylic) acids, exhibited the lowest anti-radical and antioxidant activity. The results obtained show that the antioxidant and anti-radical activity of phenolic acids correlated positively with the number of hydroxyl groups bonded to the aromatic ring. The model of an ortho substitution of hydroxyl groups to the aromatic ring seems to be adequate for antioxidant and H(2)O(2) or DPPH(*) scavenging activity of phenolic acids.

Antioxidants↗
PubMed2000

Anti-sickling, analgesic and anti-inflammatory properties of 3,5-dimethoxy-4-hydroxy benzoic acid and 2,3,4-trihydroxyacetophenone.

Effects of 3,5-dimethoxy-4-hydroxybenzoic acid and 2,3,4-trihydroxyacetophenone were studied on haemoglobin S (Hb S) polymerisation, analgesia and inflammation using Hb S solution, rats and mice. UV spectrophotometric procedure was used to monitor the polymerization of the Hb S. Acetic acid induced writhing in mice and egg albumin induced rat paw edema procedures were used to evaluate analgesic and anti-inflammatory activities of the compounds respectively. The results indicate that both drugs inhibit the process of polymerization significantly, possibly by direct action on the Hb S molecules. The drugs inhibited acetic acid induced pain and decreased egg albumin induced oedema. It is concluded that 3,5-dimethoxy-4-hydroxybenzoic acid and 2,3,4-trihydroxyacetophenone may have some value in the management of sickle cell disease.

Acetic Acid↗
PubMed2001

The loading module of rifamycin synthetase is an adenylation-thiolation didomain with substrate tolerance for substituted benzoates.

The rifamycin synthetase is primed with a 3-amino-5-hydroxybenzoate starter unit by a loading module that contains domains homologous to the adenylation and thiolation domains of nonribosomal peptide synthetases. Adenylation and thiolation activities of the loading module were reconstituted in vitro and shown to be independent of coenzyme A, countering literature proposals that the loading module is a coenzyme A ligase. Kinetic parameters for covalent arylation of the loading module were measured directly for the unnatural substrates benzoate and 3-hydroxybenzoate. This analysis was extended through competition experiments to determine the relative rates of incorporation of a series of substituted benzoates. Our results show that the loading module can accept a variety of substituted benzoates, although it exhibits a preference for the 3-, 5-, and 3,5-disubstituted benzoates that most closely resemble its biological substrate. The considerable substrate tolerance of the loading module of rifamycin synthetase suggests that the module has potential as a tool for generating substituted derivatives of natural products.

Actinomycetales↗
PubMed2001

Allelochemicals in wheat (Triticum aestivum L.): cultivar difference in the exudation of phenolic acids.

Analysis by GC-MS/MS showed that a worldwide collection of 58 wheat accessions differed significantly in the amounts of 7 known phenolic acids exuded by the living roots of 17-day-old wheat seedlings. The quantities of exuded allelochemicals varied with the specific compound and ranged from 2.3 to 18.6, from 0.6 to 17.5, from 0.1 to 4.9, from 0.0 to 52.7, from 0.33 to 12.7, from 1.5 to 20.5, and from 1.6 to 23.4 microg/L of water/agar for p-hydroxybenzoic, vanillic, cis-p-coumaric, syringic, cis-ferulic, trans-p-coumaric, and trans-ferulic acids, respectively. The concentrations of p-hydroxybenzoic and vanillic acids exuded by wheat seedlings were normally distributed in the 58 accessions. The level of each phenolic acid in root exudates did not correlate well to that previously observed in wheat. In comparison with weakly allelopathic accessions, strongly allelopathic accessions exuded larger quantities of allelochemicals into the growth medium. The chemical basis for wheat seedling allelopathy is an area for further investigation.

Carboxylic Acids↗
PubMed2002

Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection.

A high-performance liquid chromatographic (HPLC) method with diode-array detection (DAD) was used to identify and quantify free and total phenolic acids (m-hydroxybenzoic acid, p-hydroxybenzoic acid, protocatechuic acid, gallic acid, vanillic acid, syringic acid, o-coumaric acid, m-coumaric acid, p-coumaric acid, caffeic acid, ferulic acid, sinapic acid, chlorogenic acid, and ellagic acid) in plant foods. Free phenolic acids were extracted with a mixture of methanol and 10% acetic acid. Bound phenolic acids were liberated using first alkaline and then acid hydrolysis followed by extraction with diethyl ether/ethyl acetate (1:1). All fractions were quantified separately by HPLC. After HPLC quantification, results of alkali and acid hydrolysates were calculated to represent total phenolic acids. Ellagic acid was quantified separately after long (20 h) acid hydrolysis. The methods developed were effective for the determination of phenolic acids in plant foods. DAD response was linear for all phenolic acids within the ranges evaluated, with correlation coefficients exceeding 0.999. Coefficients of variation for 4-8 sample replicates were consistently below 10%. Recovery tests of phenolic acids were performed for every hydrolysis condition using several samples. Recoveries were generally good (mean >90%) with the exceptions of gallic acid and, in some cases, caffeic acid samples.

Caffeic Acids↗
PubMed2003

Phenolic composition of champagnes from Chardonnay and Pinot Noir vintages.

Nineteen phenolic compounds including hydroxybenzoic acids, hydroxycinnamic acids, flavonoids, phenolic alcohols, and phenolic aldehydes have been identified and quantified in two monovarietal champagnes, Chardonnay and Pinot Noir, by using a reverse-phase high-performance liquid chromatography (HPLC) system coupled with diode array detection. The identification of four hydroxycinnamic tartaric esters (caftaric, coutaric, fertaric, and 2-S-glutathionylcaftaric acids), two flavanonols (astilbin and engeletin), and some other compounds was confirmed by HPLC coupled with mass spectrometry. Caftaric acid and tyrosol were the major phenols. Hydroxybenzoic acids and flavonoids were present at low concentrations. The phenolic compositions of 2000 and 2001 Chardonnay and Pinot Noir vary quantitatively according to the year and the variety, but the chemical natures of the molecules are the same. The total phenolic content determined by colorimetric measurement ranges from 176 to 195 mg/L of gallic acid equivalent and is similar to that described in white wines.

Alcohols↗