title: Microbial biotransformation of bioactive flavonoids.
abstract: The bioactive flavonoids are considered as the most important phytochemicals in food, which exert a wide range of biological benefits for human being. Microbial biotransformation strategies for production of flavonoids have attracted considerable interest because they allow yielding novel flavonoids, which do not exist in nature. In this review, we summarize the existing knowledge on the production and biotransformation of flavonoids by various microbes. The main reactions during microbial biotransformation are hydroxylation, dehydroxylation, O-methylation, O-demethylation, glycosylation, deglycosylation, dehydrogenation, hydrogenation, C ring cleavage of the benzo-γ-pyrone system, cyclization, and carbonyl reduction. Cunninghamella, Penicillium, and Aspergillus strains are very popular to biotransform flavonoids and they can perform almost all the reactions with excellent yields. Aspergillus niger is one of the most applied microorganisms in the flavonoids' biotransformation; for example, A. niger can transfer flavanone to flavan-4-ol, 2'-hydroxydihydrochalcone, flavone, 3-hydroxyflavone, 6-hydroxyflavanone, and 4'-hydroxyflavanone. The hydroxylation of flavones by microbes usually happens on the ortho position of hydroxyl group on the A ring and C-4' position of the B ring and microbes commonly hydroxylate flavonols at the C-8 position. The microorganisms tend to hydroxylate flavanones at the C-5, 6, and 4' positions; however, for prenylated flavanones, dihydroxylation often takes place on the C4α=C5α double bond on the prenyl group (the side chain of A ring). Isoflavones are usually hydroxylated at the C-3' position of the B ring by microorganisms. The microbes convert flavonoids to their 7-O-glycosides and 3-O-glycosides (when flavonoids have a hydroxyl moiety at the C-3 position). The demethylation of multimethoxyl flavonoids by microbes tends to happen at the C-3' and C-4' positions of the B ring. Multimethoxyl flavanones and isoflavone are demethylated at the C-7 and C-4' positions. The O-methylation of flavonols happens at the C-3' and C-4' and microorganisms O-methylate flavones at the C-6 position and the O-methylation of flavanones, usually took place on the hydroxyl groups of the A ring. The prenyl flavanones were cyclized at the prenyl side chain to form a new five-member ring attached to the A ring. Chalcones were regioselectively cyclized to flavanones. Hydrogenation of flavonoids was only reported on transformation of chalcones to dihydrochalcones. The dehydrogenation of flavanoids to flavonoids was not comprehensively studied.
authors.affiliation: School of Chemistry and Chemical Engineering, Nantong University, Nantong 226007, PR China; Department of Chemistry, Central South University, Changsha 410083, PR China.
authors.forename: Hui
authors.initials: H
authors.lastname: Cao
authors.affiliation: Department of Chemistry, Central South University, Changsha 410083, PR China. Electronic address: xqchencsu@yahoo.com.
authors.forename: Xiaoqing
authors.initials: X
authors.lastname: Chen
authors.affiliation: Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran.
authors.forename: Amir Reza
authors.initials: AR
authors.lastname: Jassbi
authors.affiliation: State Key Laboratory of Quality Research in Chinese Medicine, Macau University of Science and Technology, Taipa, Macau, PR China; Institut für Pharmazie und Lebensmittelchemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany. Electronic address: jianboxiao@yahoo.com.
authors.forename: Jianbo
authors.initials: J
authors.lastname: Xiao
mesh_terms: D001419:Bacteria / Q000378:metabolism; D001711:Biotransformation; D044950:Flavanones / Q000378:metabolism*; D047309:Flavones / Q000378:metabolism*; D005419:Flavonoids / Q000378:metabolism*; D005658:Fungi / Q000378:metabolism; D006031:Glycosylation; D054879:Halogenation; D006865:Hydrogenation; D006900:Hydroxylation; D007218:Industrial Microbiology
chemical_list: D044950:Flavanones; D047309:Flavones; D005419:Flavonoids; C561123:4'-hydroxyflavanone; C043562:flavone; C028610:flavanone; C041477:3-hydroxyflavone
keywords: Bacteria; Flavonoids; Fungi; Microbial biotransformation