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Ultrasound-assisted conversion of tannic acid to gallic acid as a strategy to obtain value-added products.

ABSTRACT: In this work, ultrasound was applied for the conversion of tannic acid into gallic acid using only diluted H₂O₂ as reagent. Experiments were carried out using several types of ultrasonic horns operating at 20 kHz (VC750W processor). The following experimental conditions were evaluated: H₂O₂ concentration (0.2 to 8.5 mol L^-1), horn type (10 to 25 mm of diameter), ultrasound amplitude (20 to 70%), sonication time (10 to 45 min), tannic acid concentration (170 to 1360 mg L^-1), and reaction temperature (50 to 90 °C). Gallic acid production was monitored with ultra-performance liquid chromatography with high-resolution time-of-flight mass spectrometry (UPLC-ToF-MS). The isolated gallic acid was confirmed with nuclear magnetic resonance (¹H and ¹³C NMR). It is important to emphasize that this study was developed as a proof of concept to demonstrate the potential of ultrasound for tannic acid conversion into gallic acid using just diluted H₂O₂. Under selected conditions gallic acid production yield was 128 ± 4 mg g^-1 of initial tannic acid (using 170 mg L^-1 of tannic acid as starting material). Reaction time was set as 30 min, which was carried out using 1 mol L^-1 H₂O₂ and ultrasound amplitude of 50% at 90 °C. At silent conditions (mechanical stirring, from 100 to 1000 rpm), gallic acid production was halved (less than 78 ± 4 mg g^-1 of initial tannic acid).

SUBMITTER: Santos D

PROVIDER: S-EPMC7803818 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Ultrasound-assisted conversion of tannic acid to gallic acid as a strategy to obtain value-added products.

Santos Daniel D Hagemann Cauduro Vitoria V Wohlmann Wilian W Bizzi Cezar A CA Mello Paola A PA Flores Erico M M EMM

Ultrasonics sonochemistry 20201224

In this work, ultrasound was applied for the conversion of tannic acid into gallic acid using only diluted H2O2 as reagent. Experiments were carried out using several types of ultrasonic horns operating at 20 kHz (VC750W processor). The following experimental conditions were evaluated: H2O2 concentration (0.2 to 8.5 mol L-1), horn type (10 to 25 mm of diameter), ultrasound amplitude (20 to 70%), sonication time (10 to 45 min), tannic acid co ...[more]

PMID: 33388694

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Project description:Tannins and hydroxylated aromatic acids, such as gallic acid (3,4,5-trihydroxybenzoic acid), are plant secondary metabolites which protect plants against herbivores and plant-associated microorganisms. Some microbes, such as the yeast Arxula adeninivorans are resistant to these antimicrobial substances and are able to use tannins and gallic acid as carbon sources. In this study, the Arxula gallic acid decarboxylase (Agdc1p) which degrades gallic acid to pyrogallol was characterized and its function in tannin catabolism analyzed. The enzyme has a higher affinity for gallic acid (Km -0.7 ± 0.2 mM, kcat -42.0 ± 8.2 s-1) than to protocatechuic acid (3,4-dihydroxybenzoic acid) (Km -3.2 ± 0.2 mM, kcat -44.0 ± 3.2 s-1). Other hydroxylated aromatic acids, such as 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid are not gallic acid decarboxylase substrates. A. adeninivorans G1212/YRC102-AYNI1-AGDC1, which expresses the AGDC1 gene under the control of the strong nitrate inducible AYNI1 promoter achieved a maximum gallic acid decarboxylase activity of 1064.4 U/l and 97.5 U/g of dry cell weight in yeast grown in minimal medium with nitrate as nitrogen source and glucose as carbon source. In the same medium, gallic acid decarboxylase activity was not detected for the control strain G1212/YRC102 with AGDC1 expression under the control of the endogenous promoter. Gene expression analysis showed that AGDC1 is induced by gallic acid and protocatechuic acid. In contrast to G1212/YRC102-AYNI1-AGDC1 and G1212/YRC102, A. adeninivorans G1234 [Δagdc1] is not able to grow on medium with gallic acid as carbon source but can grow in presence of protocatechuic acid. This confirms that Agdc1p plays an essential role in the tannic acid catabolism and could be useful in the production of catechol and cis,cis-muconic acid. However, the protocatechuic acid catabolism via Agdc1p to catechol seems to be not the only degradation pathway.

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Ultrasound-assisted conversion of tannic acid to gallic acid as a strategy to obtain value-added products.

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Ultrasound-assisted conversion of tannic acid to gallic acid as a strategy to obtain value-added products.

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