Print 2017 May. The maximum conversion was observed in 0.1 M phosphate buffer (pH 8.0), using 60 mM … Time course of growing cell biotransformations of vanillic acid by Nocardia sp. NIH Untersuchungen über pflanzenfarbstoffe I. Über die konstitution einiger anthocyanidine. Biocatal Biotransform 31(1):42–48, Civolani C, Barghini P, Roncetti AR, Ruzzi M, Schiesser A (2000) Bioconversion of ferulic acid into vanillic acid by means of a vanillate-negative mutant of Pseudomonas fluorescens strain BF13. While we use encryption to protect sensitive information transmitted online, we also protect your information offline. Glucose homeostasis was assessed with a glucose or insulin tolerance test. Copyright © 2020 American Society for Microbiology | Privacy Policy | Website feedback, Print ISSN: 0099-2240; Online ISSN: 1098-5336, Division of Medicinal and Natural Products Chemistry, and Center for Biocatalysis and Bioprocessing, College of Pharmacy, University of Iowa, Iowa City, Iowa 52242, Sign In to Email Alerts with your Email Address. eCollection 2020. Vanillic acid is the major product obtained by β-oxidation of ferulic acid by species ofBacillus , Pseudomonas (11, 23), Polyporus , Rhodotorula, and Streptomyces (17, 22). After 5 min of equilibration, the cartridge was washed three times with 200 ml of hexane and then three times with 200 ml of dichloromethane. Protein Pept Lett. Mechanisms of ferulic acid conversions to vanillic acid and guaiacol by. Appl Microbiol Biotechnol 51:456–461, Kumar V, Kumar V, Thakur N, Bhalla TC (2015) Bench scale synthesis of p-hydroxybenzoic acid using whole cells nitrilase of Gordonia terrae mutant E9. Deciphering the Anti-obesity Benefits of Resveratrol: The "Gut Microbiota-Adipose Tissue" Axis. strain NRRL 5646. J Biotechnol 156:309–316, Walton NJ, Mayer MJ, Narbad A (2003) Vanillin. PubMed Google Scholar. The innovative approach proposed herein for the first time, which involves the synthesis of sustainable monomers under solvent-free conditions, is fully aligned with one of the main principles of green chemistry. Developed plates were first sprayed with a freshly prepared equal-volume mixture of solutions A and B and then sprayed with solution C before being heated with a heat gun to develop colors from yellow to orange. 2015;22(1):52-62. doi: 10.2174/0929866521666140909154537. In the preparative scale incubation reaction, TLC analysis indicated that benzoate-induced Nocardia cells produced two major metabolites corresponding to 4-O-benzylvanillin (compound 3b, 170 mg, 24% yield) and 4-O-benzylvanillyl alcohol (compound 4b, 210 mg, 30% yield). All polymers have high thermal stability. The organic extracts were separately concentrated by rotary evaporation to give 45 mg of oil (from hexane) and 90 mg of residue (from dichloromethane). CAS Part of Springer Nature. The medium contained 20 g of glucose, 5 g of yeast extract, 5 g of soybean flour, 5 g of NaCl, and 5 g of K2HPO4 per liter in distilled water and was adjusted to pH 7.2 with 6 N HCl before being autoclaved at 121°C for 20 min. Vanillic acid (4-hydroxy-3-methoxybenzoic acid) is a dihydroxybenzoic acid derivative used as a flavoring agent. Immediate online access to all issues from 2019. You will get an estimated time at checkout. Ionizing matrices were either 3-nitrobenzyl alcohol or thioglycerol. Based on your measures, we model your boots. Both the adenylation and carbonyl-AMP reduction steps are catalyzed by a single enzyme (5, 13, 16). USA.gov. Microb Cell Fact 9:84, Topakas E, Kalogeris E, Kekos D, Macris BJ, Christakopoulos P (2003) Bioconversion of ferulic acid into vanillic acid by the thermophilic fungus Sporotrichum thermophile. High-performance liquid chromatography (HPLC) was performed with a Shimadzu liquid chromatograph equipped either with a LC-10AD system controller, four FCV-10AL pumps, and a photodiode array UV-Vis detector (SPD-M6A) or with a SCL 6-B system controller, two LC-6A pumps, and a variable-wavelength UV detector. Bioprocess Biosyst Eng 36(5):613–625, Zhanj ZJ, Xu JH, He YC, Ouyang LM, Liu YY, Imanaka T (2010) Efficient production of (R)- mandelic acid with highly substrate/product tolerant and enatioselective nitrilase from recombinant Alcaligenes sp. Solvent-free synthesis of monomers is one among the most promising ways to develop greener polymers that are both environmentally and economically acceptable, but it was described as one of the “grand challenges” facing chemists. strain NRRL 5646 and a pure aryl aldehyde oxidoreductase (carboxylic acid reductase) from this organism. Solvent-free synthesis of the three fully biobased vanillic acid-based diols was performed according to the following procedure: To an amount of diol (1 eq, 130 mmol) was added 2 eq (260 mmol) of vanillic acid in a round bottom reactor equipped with a mechanical stirrer. In whole-cell Nocardia biotransformation reactions, vanillic acid decarboxylation to guaiacol was the major complicating pathway. What personally identifiable information is collected from you through the web site, how it is used and with whom it may be shared. Enter multiple addresses on separate lines or separate them with commas. NMR spectra were obtained with a Bruker WM 360-MHz high-field spectrometer equipped with an IBM Aspect-2000 processor. With dichloromethane-acetonitrile-formic acid (75:25:1 [vol/vol/vol]),Rf values for vanillic acid, vanillin, vanillyl alcohol, and guaiacol were 0.5, 0.4, 0.8, and 0.9, respectively. 4-O-Benzylvanillin (170 mg, 24% yield) was eluted with dichloromethane, while 4-O-benzylvanillyl alcohol (210 mg, 30% yield) was eluted with dichloromethane-benzene-acetic acid (100:4:6 [vol/vol/vol]). Zhou L, Xiao X, Zhang Q, Zheng J, Deng M. Front Endocrinol (Lausanne). Sandoval V, Sanz-Lamora H, Arias G, Marrero PF, Haro D, Relat J. Nutrients. The identification of guaiacol and vanillyl alcohol as metabolites confirmed that Nocardia sp. Clipboard, Search History, and several other advanced features are temporarily unavailable. also contains another reductase that converts aldehydes to alcohols (unpublished data). Biotransformation of vanillic acid with growing cells ofNocardia sp.HPLC analyses of vanillic acid biotransformation by Nocardia sp. Bioprocess and Biosystems Engineering ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. Int J Pharma Stud Res 1:100–105, Kornhauser A, Coelho SG, Hearing VJ (2010) Applications of hydroxy acids: classification, mechanisms and photoactivity. Many microbial transformation approaches have been used to produce vanillin. The Role of the Gut Microbiome in Energy Balance With a Focus on the Gut-Adipose Tissue Axis. The structure of compound 1b was confirmed by low-resolution electron impact mass spectrometry (EIMS) with the following parameters: m/z 258 (8%, M+) and 91 (100%, benzonium ion); 1H nuclear magnetic resonance (NMR) at 360 MHz (d6-acetone), δH 3.83 (3H, s, OCH3), 5.21 (2H, s, C-7′), 7.12, 7.14 (1H, d, J = 8.3 Hz, H-5), 7.33 to 7.52 (5H, m, H-2′, -3′, -4′, -5′, and -6′), 7.58, 7.57 (1H, d, J = 2.0 Hz, H-2), and 7.63 to 7.65 (1H, dd, J = 8.3, 2.0 Hz, H-6). Zhang H, Hao Y, Wei C, Yao B, Liu S, Zhou H, Huang D, Zhang C, Wu Y. Biomed Pharmacother. Ferulic acid [3-(4-hydroxy-3-methoxyphenyl)-propenoic acid] is an extremely abundant plant product available from corn kernel hulls obtained from wet milling (21). Process Biochem 45:887–891, Bhatia SK, Mehta PK, Bhatia RK, Bhalla TC (2013) Optimization of arylacetonitrilase production from Alcaligenes sp. When you submit sensitive information via the website, your information is protected both online and offline. Fed batch reaction for transformation of 4-hydroxy-3-methoxybenzonitrile using whole cell nitrilase of wild G. terrae resulted in 2.36 g of vanillic acid in 5 h with a catalytic and volumetric productivity of 0.78 gg(-1)(DCW) h(-1) and 4.72 gL(-1)h(-1), respectively. We will use your information to respond to you, regarding the reason you contacted us. doi: 10.1371/journal.pone.0173661. CAS number: 121-34-6. Epub 2017 Jul 25. 2019 Sep 27;19:676-690. doi: 10.1016/j.isci.2019.08.020. Thus, 4-O-benzylvanillic acid was reduced first to the aldehyde 3b and subsequently to the alcohol 4b (Fig. Analytical scale biotransformations were conducted in the same medium as for preparative biotransformations. We know that Nocardia sp. β-Lapachone Prevents Diet-Induced Obesity by Increasing Energy Expenditure and Stimulating the Browning of White Adipose Tissue via Downregulation of miR-382 Expression. 2019 Jun 27;10:413. doi: 10.3389/fendo.2019.00413. HHS Results showed high melting points in the 121.8–142.3 °C range and no significant weight loss (Td, 5%) up to 243, 312 and 284 °C respectively for diols with 2, 3, and 4 methylene units. This study demonstrated that vanillic acid could prevent obesity by activating BAT thermogenesis and the promotion of inguinal WAT browning. 4-O-Benzylation of vanillic acid was carried out by adding 11 ml of 1 N NaOH to 900 mg of vanillic acid (5.4 mmol) in 16 ml of ethanol, followed by dropwise addition of 1 g (5.8 mmol) of benzyl bromide in 2.5 ml of ethanol over 60 min. Curr Opin Chem Biol. Tetramethylsilane was used as the internal standard. In: Havkin-Frenkel D, Belanger FC (eds) Biotechnology in flavor production. The resting cells of Gordonia terrae mutant E9 having enhanced nitrilase activity were used for biotransformation of 4-hydroxy-3-methoxybenzonitrile into vanillic acid. Furthermore, reductions of carboxylic acids to aldehydes are difficult to achieve by chemical means, and the reduction of vanillic acid to vanillin has not been widely reported. Epub 2011 Sep 22. MTCC 10675 and its application in mandelic acid synthesis. This privacy policy applies solely to information collected by this web site. Karrer, P., and Widmer, R. 1927. Abstract. Erythropoietin (EPO) ameliorates obesity and glucose homeostasis by promoting thermogenesis and endocrine function of classical brown adipose tissue (BAT) in diet-induced obese mice. Bioprocess Biosyst Eng 38(7):1267–1279, Fawcett JK, Scott JE (1960) A rapid and precise method for the determination of urea. Synonym: 4-Hydroxy-3-methoxybenzoic acid. The carboxylic acid reductase used in enzymatic reductions of vanillic acid was isolated from Nocardia sp. Chromatography.Thin-layer chromatography (TLC) was carried out on silica gel GF254 plates (E. Merck, Darmstadt, Germany). Synthesis of vanillic acid using whole cell nitrilase of wild and mutant Gordonia terrae We fed C57BL/6J mice vanillic acid supplements in a high fat and high fructose diet for 16 weeks. 1). All materials revealed high thermal stability with onset degradation temperatures Td, 5% ranging from 314 to 373 °C and a wide glass transition temperature (Tg) range oscillating from -2.8 to 69.5 °C. Vanillic acid is the major product obtained by β-oxidation of ferulic acid by species ofBacillus , Pseudomonas (11, 23), Polyporus , Rhodotorula, and Streptomyces (17, 22). After 5 min, cartridges were extracted twice with 3 ml each of dichloromethane-acetonitrile (90:10). The security procedures in place to protect the misuse of your information. 2017 Mar 13;12(3):e0173661. Extremophiles. Effective and facile solvent-free synthesis route to novel biobased monomers from vanillic acid: Structure–thermal property relationships of sustainable polyesters. In our laboratory, the mechanism of ferulic acid transformation to vanillic acid by R. rubra IFO 889 occurred by β-oxidation (8). Old Wellington Mall Page you are looking for does not exists anymore. We are also thankful to computational facility at Sub Distributed Information Centre, Himachal Pradesh University, Shimla-171005, India. Only employees who need the information to perform a specific job (for example, billing or customer service) are granted access to personally identifiable information. Recrystallization in ethanol gave 45.3 g (187 mmol, 85% yield) of compound 3b confirmed by EIMS: m/z 242 (4%, M+), 91 (100%, benzonium ion); 1H NMR at 360 MHz (CDCl3), δH 3.95 (3H, s, OCH3), 5.25 (2H, s, C-7′), 7.00, 6.98 (1H, d, J = 8.3 Hz, H-5), 7.34 to 7.43 (7H, m, H-2, -6, -2′, -3′, -4′, -5′, and -6′), and 9.84 (1H, s, H-7). The cells were harvested by centrifugation at 8,000 × g for 20 min at 24 h after the benzoate addition.
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