ferulic acid glucoside

Joong-Hoon Ahn. J. Mol. The statements, opinions and data contained in the journals are solely 117405-51-3. 2018; 19(8):2321. It has a role as an antioxidant, a MALDI matrix material, a plant metabolite, an anti-inflammatory agent, an apoptosis inhibitor and a … Below is the link to the electronic supplementary material. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). PubMed Google Scholar. Part of Springer Nature. The tea brewed from the leaves of yacón (Smallanthus sonchifolius), a plant traditionally grown in the northern and central Andes, contains quantities of ferulic acid. Ferulic acid beta-D-glucopyranoside Google Scholar, Kim HS, Kim B-G, Sung S, Kim M, Mok H, Chong Y, Ahn J-H (2013) Engineering flavonoid glycosyltransferases for enhanced catalytic efficiency and extended sugar donor selectivity. We used biotransformation using E. coli harboring each UGT. Ferulic acid is converted by certain strains of yeast, notably strains used in brewing of wheat beers, such as Saccharomyces delbrueckii (Torulaspora delbrueckii), to 4-vinyl guaiacol (2-methoxy-4-vinylphenol) which gives beers such as Weissbier and Wit their distinctive "clove" flavour. Sci. [13] As plant sterol esters, this compound is naturally found in rice bran oil, a popular cooking oil in several Asian countries. Twelve candidate uridine diphosphate-dependent glucosyltransferases (UGTs) from Arabidopsis thaliana were screened to identify UGTs that synthesized ferulic acid 4-O-glucoside or feruloyl glucoside, respectively. MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. You seem to have javascript disabled. Biosynthesis of ferulic acid 4-O-glucoside and feruloyl glucoside using Escherichia coli harboring regioselective glucosyltransferases. Abstract: Trans-ferulic acid-4- -glucoside (C16H20O9, TFA-4 -G) is a monomer extracted from the Chinese medicine called radix aconiti carmichaeli (Fuzi). Ferulic acid is a ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring. [22], It is used as a matrix for proteins in MALDI mass spectrometry analyses. Here, we found that trans-ferulic acid-4-β-glucoside effectively promoted cold acclimatization in mice via increased heat production and alleviation of oxidative stress in a cold environment. Our dedicated information section provides allows you to learn more about MDPI. Annu Rev Plant Biol 57:567–597, CAS  To date, research on this substance is lacking. Please note that many of the page functionalities won't work as expected without javascript enabled. Authors to whom correspondence should be addressed. Xue C, Lu H, Liu Y, Zhang J, Wang J, Luo W, Zhang W, Chen J. Trans-Ferulic Acid-4-β-Glucoside Alleviates Cold-Induced Oxidative Stress and Promotes Cold Tolerance. Ferulic acid is a hydroxycinnamic acid, an organic compound. Ferulic acid is less commonly taken as an oral supplement but is believed by some to enhance athletic performance and slow the aging process. Trend Plant Sci 5:380–386. [8], Asterid eudicot plants can also produce ferulic acid. Appl Environ Microbiol 80:2754–2762, Johnsson P, Peerlkamp N, Kamal-Eldin A, Andersson RE, Andersson R, Lundgren LN, Åmana P (2002) Polymeric fractions containing phenol glucosides in flaxseed. Xue, Chong; Lu, Huanyu; Liu, Ying; Zhang, Jianbin; Wang, Jiye; Luo, Wenjing; Zhang, Wenbin; Chen, Jingyuan. Sci. To date, research on this substance is lacking. E. coli harboring AtUGT72E2 showed the best conversion rate for converting ferulic acid into ferulic acid glucoside, at 15.8 μM/h. Arch Biochem Biophys 439:198–203, Article  When applied topically, ferulic acid is said to treat sun damageand reverse the signs of aging (including fine lines and wrinkles). Alzhei… Department of Occupational and Environmental Health, Fourth Military Medical University, Key Laboratory of Hazard Assessment and Control in Special Operational Environment, Ministry of Education, Xi’an 710032, China. Subscribe to receive issue release notifications and newsletters from MDPI journals, You can make submissions to other journals. Applied Biological Chemistry The statements, opinions and data contained in the journal, © 1996-2020 MDPI (Basel, Switzerland) unless otherwise stated. CHEMBL3403684. [7] It is also found in barley grain. 2018, 19, 2321. Google Scholar, Caputi L, Lim E-K, Bowles DJ (2008) Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds. 2018. https://doi.org/10.1007/s13765-016-0186-3, DOI: https://doi.org/10.1007/s13765-016-0186-3, Over 10 million scientific documents at your fingertips, Not logged in Here, we found that trans-ferulic acid-4-β-glucoside effectively promoted cold acclimatization in mice via increased heat production and alleviation of oxidative stress in a cold environment. [16], Ferulic acid is biosynthesized in plants from caffeic acid by the action of the enzyme caffeate O-methyltransferase. Biochem Insights 4:1–12, CAS  In addition, ferulic acid is sometimes used to prevent or treat certain health conditions, including: 1. As a building block of lignocelluloses, such as pectin and lignin, ferulic acid is ubiquitous in the plant kingdom. 8: 2321. J Biol Chem 276:4344–4349, Lim EK, Higgins GS, Li Y, Bowles DJ (2003) Regioselectivity of glucosylation of caffeic acid by a UDP-glucose:glucosyltransferase is maintained in planta. Planta 238:683–693, Kim SY, Lee HR, K-s Park, Kim BG, Ahn J-H (2015) Metabolic engineering of Escherichia coli for the biosynthesis of flavonoid O-glucuronides and flavonoid O-galactoside. It is an intermediate in the synthesis of monolignols, i.e., the monomers of lignin, and is also used for the synthesis of lignans. Article  International Journal of Molecular Sciences. Da Ye Han and Hye Rin Lee authors contributed equally to this work. [21], It can be extracted from wheat bran and maize bran using concentrated alkali. As a component of lignin, ferulic acid is a precursor in the manufacture of other aromatic compounds. In wheat, phenolic compounds are mainly found in the form of insoluble bound ferulic acid and may be relevant to resistance to wheat fungal diseases. et al. [9] It is also found in horse grams (Macrotyloma uniflorum). CHEBI:139435. Trans-ferulic acid-4-β-glucoside (C 16 H 20 O 9, TFA-4β-G) is a monomer extracted from the Chinese medicine called radix aconiti carmichaeli (Fuzi).To date, research on this substance is lacking. Chem Eur J 14:6656–6662, Han SH, Kim B-G, Yoon JA, Chong Y, Ahn J-H (2014) Synthesis of flavonoid O-pentosides by Escherichia coli through engineering nucleotide sugar synthesis pathway and glycosyltransferase. Molecular docking analysis of ferulic acid into the modeled structures of AtUGT71C1 and AtUGT72E2 was used to elucidate the different conversion rates of ferulic acid into corresponding glucoside. J. Mol. 19, no. [15] Rye bread contains ferulic acid dehydrodimers. Biochem J 373:987–992, Lim E-K, Jackson RG, Bowles DJ (2005) Identification and characterization of Arabidopsis glycosyltransferase capable of glucosylating coniferyl aldehyde and sinapyl aldehyde. [5], In cereals, ferulic acid is localized in the bran – the hard outer layer of grain. Sigma-Aldrich offers a number of Ferulic acid products. those of the individual authors and contributors and not of the publisher and the editor(s). Find support for a specific problem on the support section of our website. E. coli … Appl Microbiol Biot 99:2233–2242, Kubo A, Arai Y, Nagashima S, Yoshikawa T (2004) Alteration of sugar donor specificities of plant glycosyltransferases by a single point mutation. FEBS Lett 579:2802–2806, Vogt T, Jones P (2000) Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Appl Biol Chem 59, 481–484 (2016). Learn more about Institutional subscriptions, Bowles D, Lim E-K, Poppenberger B, Vaistij FE (2006) Glycosyltransferases of lipophilic small molecules. "Trans-Ferulic Acid-4-β-Glucoside Alleviates Cold-Induced Oxidative Stress and Promotes Cold Tolerance." Here, we found that trans-ferulic acid-4- -glucoside effectively promoted cold acclimatization in mice - 178.254.54.92. [10], Ferulic acid has been identified in Chinese medicine herbs such as Angelica sinensis (female ginseng), Cimicifuga heracleifolia[11] and Ligusticum chuangxiong. Plant J 48:286–295, Lim E-K, Li Y, Parr A, Jackson R, Ashford DA, Bowles DJ (2001) Identification of glucosyltransferase genes involved in sinapate metabolism and synthesis in Arabidopsis. [23], 2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+, InChI=1/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+, Except where otherwise noted, data are given for materials in their, DTXSID70892035 DTXSID5040673, DTXSID70892035, 10.1002/(SICI)1097-0010(19990301)79:3<396::AID-JSFA262>3.0.CO;2-B, "Potential applications of ferulic acid from natural sources", "Inhibitory effect of ferulic acid and isoferulic acid on the production of macrophage inflammatory protein-2 in response to respiratory syncytial virus infection in RAW264.7 cells", "Cooking sweet corn boosts its ability to fight cancer and heart disease by freeing healthful compounds, Cornell scientists find", "Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens", "Purification and characterization of a ferulic acid decarboxylase from Pseudomonas fluorescens", https://en.wikipedia.org/w/index.php?title=Ferulic_acid&oldid=981440083, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Articles with unsourced statements from December 2019, Creative Commons Attribution-ShareAlike License, 168 to 172 °C (334 to 342 °F; 441 to 445 K), This page was last edited on 2 October 2020, at 09:51. Ferulic acid is best known for its skin-protective properties.

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