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Optimization Technology of the LHS-1 Strain for Degrading Gallnut Water

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Optimization Technology of the LHS-1 Strain for Degrading Gallnut Water molecules Article Optimization Technology of the LHS-1 Strain for Degrading Gallnut Water Extract and Appraisal of Benzene Ring Derivatives from Fermented Gallnut Water Extract Pyrolysis by Py-GC/MS Chengzhang Wang 1,2,3,4,5,* and Wenjun Li 1,2,3,4,5 1 Institute of Chemical Industry of Forest Products, Chinese Academy Forestry, Nanjing 210042, China; [email protected] 2 National Engineering Laboratory for Biomass Chemical Utilization, Nanjing 210042, China 3 Key and Open Laboratory on Forest Chemical Engineering, State Forestry Administration, Nanjing 210042, China 4 Key Laboratory of Biomass Energy and Material, Nanjing 210042, China 5 Institute of New Technology of Forestry, Chinese Academy Forestry, Beijing 100091, China * Correspondence: [email protected]; Tel./Fax: +86-025-8548-2471 Received: 31 October 2017; Accepted: 11 December 2017; Published: 20 December 2017 Abstract: Gallnut water extract (GWE) enriches 80~90% of gallnut tannic acid (TA). In order to study the biodegradation of GWE into gallic acid (GA), the LHS-1 strain, a variant of Aspergillus niger, was chosen to determine the optimal degradation parameters for maximum production of GA by the response surface method. Pyrolysis–gas chromatography–mass spectrometry (Py-GC/MS) was first applied to appraise benzene ring derivatives of fermented GWE (FGWE) pyrolysis by comparison with the pyrolytic products of a tannic acid standard sample (TAS) and GWE. The results showed that optimum conditions were at 31 ◦C and pH of 5, with a 50-h incubation period and 0.1 g·L−1 of TA as substrate. The maximum yields of GA and tannase were 63~65 mg·mL−1 and 1.17 U·mL−1, respectively. Over 20 kinds of compounds were identified as linear hydrocarbons and benzene ring derivatives based on GA and glucose. The key benzene ring derivatives were 3,4,5-trimethoxybenzoic acid methyl ester, 3-methoxy-1,2-benzenediol, and 4-hydroxy-3,5-dimethoxy-benzoic acid hydrazide. Keywords: gallnut water extract; tannic acid; benzene ring derivatives; biodegradation; Py-GC/MS 1. Introduction Gallnut is an abnormal gall in China produced by parasitic aphids on the host trees of Rhus chinensis, Rhus potaninii, or Rhus punjabensis, etc. Chinese gallnut can be divided into the three categories of Du-ensiform gall, horned gall, and gall flowers, according to aphid species and host differences. Du-ensiform gall enriches 55~65% of tannin (Figure1), and is the most traditional and important raw material for producing gallnut water extract (GWE) which contains 80~90% tannin. GWE has been used to produce gallic acid through the hydrolysis of alkali, and acid catalysis. However, chemical degradation of GWE not only provides very low yields of gallic acid, but causes serious environmental pollution and equipment corrosion. Therefore, it is urgent to probe more environmentally friendly degradation technology in order to produce gallic acid and its derivatives [1,2]. Molecules 2017, 22, 2253; doi:10.3390/molecules22122253 www.mdpi.com/journal/molecules Molecules 2017, 22, 2253 2 of 11 Molecules 2017, 22, 2253 2 of 11 (a) (b) FigureFigure 1. 1. ChineseChinese Du-ensiform Du-ensiform gallnut, gallnut, (a ()a )fresh fresh gallnut; gallnut; (b (b) )dry dry gallnut. gallnut. The enzymatic hydrolysis of GWE using the microorganisms of Aspergillus and Penicillium, The enzymatic hydrolysis of GWE using the microorganisms of Aspergillus and Penicillium, particularly Aspergillus niger, has great potential for the industrialized production of gallic acid [3]. particularly Aspergillus niger, has great potential for the industrialized production of gallic acid [3]. Wang [4] separated one strain of A. niger from Chinese Gall “Beihua” and fermented gallnut directly Wang [4] separated one strain of A. niger from Chinese Gall “Beihua” and fermented gallnut directly to produce GA with a yield of 78.5~89.5%. Yang [5] used the same strain to ferment gallotannins and to produce GA with a yield of 78.5~89.5%. Yang [5] used the same strain to ferment gallotannins purified macroporous resin to obtain a high yield of 85.6% gallic acid. Banerjee modified a tannin- and purified macroporous resin to obtain a high yield of 85.6% gallic acid. Banerjee modified a rich substrate of solid-state fermentation (MSSF) to produce tannase and gallic acid through co- tannin-rich substrate of solid-state fermentation (MSSF) to produce tannase and gallic acid through culture method to obtain maximum yield of 94.8% gallic acid (GA) [6]. However, no literature has co-culture method to obtain maximum yield of 94.8% gallic acid (GA) [6]. However, no literature has reported on fermented GWE chemical constitutes and structures so far, particularly with respect to reported on fermented GWE chemical constitutes and structures so far, particularly with respect to the the biodegradation mechanism of GWE biotransformation. biodegradation mechanism of GWE biotransformation. Since the microbial transformation of tannins was discovered by Tieghem [7], only a few Since the microbial transformation of tannins was discovered by Tieghem [7], only a few analytical analytical techniques, such as high-performance liquid chromatography (HPLC), thin-layer techniques, such as high-performance liquid chromatography (HPLC), thin-layer chromatography chromatography (TLC), or pyrolysis–gas chromatography–mass spectrometry (Py-GC/MS) have (TLC), or pyrolysis–gas chromatography–mass spectrometry (Py-GC/MS) have been applied to been applied to the identification of natural products and their metabolites by both conventional the identification of natural products and their metabolites by both conventional destructive or destructive or non-destructive methods in the process of chemical synthesis and biotransformation non-destructive methods in the process of chemical synthesis and biotransformation [8–11]. In order [8–11]. In order to develop gallic acid by microbial degradation of GWE, Min previously reported the to develop gallic acid by microbial degradation of GWE, Min previously reported the extraction and extraction and screening of tannic acid degradation by the LHS-1 strain according to the indexes of screening of tannic acid degradation by the LHS-1 strain according to the indexes of tannic acid tannic acid degradation rate, gallic acid accumulation concentration, and tannin enzyme activity [12]. degradation rate, gallic acid accumulation concentration, and tannin enzyme activity [12]. This study This study focused on the optimization technology of LHS-1 strain degradation of GWE, and Py- focused on the optimization technology of LHS-1 strain degradation of GWE, and Py-GC/MS was GC/MS was applied to probe the chemical constituents and structural characterization of the linear applied to probe the chemical constituents and structural characterization of the linear and benzene and benzene ring derivatives, based on phenolic and glucose structure from fermented GWE (FGWE) ring derivatives, based on phenolic and glucose structure from fermented GWE (FGWE) pyrolysis. pyrolysis. It will be very helpful for us to research the biodegradation mechanism and the It will be very helpful for us to research the biodegradation mechanism and the corresponding corresponding metabolites of GWE for the future. metabolites of GWE for the future. 2. Results 2. Results 2.1.2.1. Determination Determination of of Tannic Tannic Acid Acid and and Gallic Gallic Acid Acid in in FGWE FGWE Folin–CiocalteauFolin–Ciocalteau and and HPLC HPLC were were both both used used to to moni monitortor the the changes changes in in gallic gallic acid acid and and tannic tannic acid acid inin GWE GWE biodegradation biodegradation with with the the LHS-1 LHS-1 strain. strain. The The standard standard curves curves of tannic of tannic acid and acid gallic and gallic acid had acid 2 higherhad higher linearity. linearity. Tannic Tannic acid was acid dete wascted detected at 630 atnm, 630 and nm, its and equation its equation was y was= 69.848y =x 69.848 + 0.0011x + 0.0011(R = 2 0.9993),(R2 = 0.9993) while, the while equation the equation of gallic of acid gallic was acid y = was0.0029y =x 0.0029+ 0.0039x + (R 0.0039 = 0.9998). (R2 = The 0.9998). analysis The showed analysis GWEshowed contained GWE contained81.6% of tannin 81.6% acid of tannin and 5.6% acid of and gallic 5.6% acid. of gallicWhen acid.GWE When was incubated GWE was at incubated 28 °C with at a28 pH◦C of with 5.0 for a pH 50 ofh, 5.0HPLC for 50showed h, HPLC that showed the levels that of thetannic levels acid of decreased tannic acid and decreased those of and gallic those acid of increasedgallic acid significantly increased significantly in FGWE (Figure in FGWE 2). (Figure2). Molecules 2017, 22, 2253 3 of 11 Molecules 2017, 22, 2253 3 of 11 Molecules 2017, 22, 2253 3 of 11 mAU mA U mAU mA U 270nm,4nm (1.00) 270nm,4nm (1.00) 270nm,4nm (1.00) 270nm,4nm (1.00) 100 100 2000 2000 50 50 1000 1000 0 0 0 0 0.0 5.0 10.0 15.0 20.0 min 0.0 5.0 10.0 15.0 20.0 25.0 30.0 min 0.0 5.0 10.0 15.0 20.0 min 0.0 5.0 10.0 15.0 20.0 25.0 30.0 min (a) (b) (a) (b) Figure 2. HPLC of a standard gallic acid sample and fermented gallnut water extract (FGWE), (a) FigureFigure 2. 2. HPLCHPLC of ofa standard a standard gallic gallic acid acid sample sample and and fermented fermented gallnut gallnut water water extract extract (FGWE), (FGWE), (a) standard sample of gallic acid; (b) the fermentation broth of GWE. standard(a) standard sample sample of gallic of gallic acid; acid; (b) the (b) fermentation the fermentation broth broth of GWE. of GWE. The degradation rate of GWE tannic acid exceeded 85.6%.
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