Microbial biotransformation of bioactive flavonoids

Abourashed, 2012, Bioconversion of silybin to phase I and II microbial m etabolites with retained antioxidant activity, Bioorg Med Chem, 20, 2784, 10.1016/j.bmc.2012.03.046 Akihisa, 2012, Cytotoxic activities and anti-tumor-promoting effects of microbial transformation products of prenylated chalcones from Angelica keiskei, Chem Biodivers, 9, 318, 10.1002/cbdv.201100255 Alarcón, 2013, Aspergillus niger catalyzes the synthesis of flavonoids from chalcones, Biocat Biotransform, 31, 160, 10.3109/10242422.2013.813489 Andrae-Marobela, 2013, Polyphenols: a diverse class of multi-target anti-HIV-1 agents, Curr Drug Metab, 7, 392, 10.2174/13892002113149990095 Araújo, 2013, Bioconversion of quercetin and rutin and the cytotoxicity activities of the transformed products, Food Chem Toxicol, 51, 93, 10.1016/j.fct.2012.09.015 Ballester, 2013, Citrus phenylpropanoids and defence against pathogens. Part I: Metabolic profiling in elicited fruits, Food Chem, 136, 178, 10.1016/j.foodchem.2012.07.114 Bandyukova, 1971, The structure of methoxylated flavonoids, Chem Nat. Comput., 7, 250, 10.1007/BF00568991 Barreca, 2013, Polymethoxylated, C- and O-glycosyl flavonoids in tangelo (Citrus reticulata×Citrus paradisi) juice and their influence on antioxidant properties, Food Chem, 141, 1481, 10.1016/j.foodchem.2013.03.095 Barreca, 2014, Biochemical and antimicrobial activity of phloretin and its glycosilated derivatives present in apple and kumquat, Food Chem, 160, 292, 10.1016/j.foodchem.2014.03.118 Bartmańska, 2013, Biotransformations of prenylated hop flavonoids for drug discovery and production, Curr Drug Metab, 14, 1083, 10.2174/1389200214666131211151855 Bartmańska, 2010, Biotransformation of the phytoestrogen 8-prenylnaringenin, Z Naturforsch C, 65, 603, 10.1515/znc-2010-9-1012 Bernini, 2011, A convenient and safe O-methylation of flavonoids with dimethyl carbonate (DMC), Molecules, 16, 1418, 10.3390/molecules16021418 Buisson, 2007, Biotransformation of polymethoxylated flavonoids: access to their 4′-O-demethylated metabolites, J Nat Prod, 70, 1035, 10.1021/np070084q Corrêa, 2011, Biotransformation of chalcones by the endophytic fungus Aspergillus flavus isolated from Paspalum maritimum Trin, J Braz Chem Soc, 22, 1333, 10.1590/S0103-50532011000700019 Costa, 2008, Selection of filamentous fungi of the Beauveria genus able to metabolize quercetin like mammalian cells, Braz J Microbiol, 39, 405, 10.1590/S1517-83822008000200036 Dajanta, 2009, Enhanced aglycone production of fermented soybean products by Bacillus species, Acta Biol Szeged, 53, 93 Escriche, 2014, Suitability of antioxidant capacity, flavonoids and phenolic acids for floral authentication of honey. Impact of industrial thermal treatment, Food Chem, 142, 135, 10.1016/j.foodchem.2013.07.033 Das, 2006, Microbial and enzymatic transformations of flavonoids, J Nat Prod, 69, 499, 10.1021/np0504659 de Lacey, 2014, Biotransformation and resulting biological properties of green tea polyphenols produced by probiotic bacteria. LWT–Food, Sci Technol, 58, 633 Gechev, 2014, Natural products from resurrection plants: potential for medical applications, Biotechnol Adv, 32, 1091, 10.1016/j.biotechadv.2014.03.005 Gioia, 2014, Flavonoid bioconversion in Bifidobacterium pseudocatenulatum B7003: a potential probiotic strain for functional food development, J Funct Foods, 7, 671, 10.1016/j.jff.2013.12.018 Hanasaki, 1994, The correlation between active oxygen scavenging and antioxidative effects of flavonoids, Free Radic Biol Med, 16, 845, 10.1016/0891-5849(94)90202-X Herath, 2003, Identification and biological activity of microbial metabolites of xanthohumol, Chem Pharm Bull, 51, 1237, 10.1248/cpb.51.1237 Herath, 2003, Microbial transformation of xanthohumol, Phytochemistry, 62, 673, 10.1016/S0031-9422(02)00615-5 Hosny, 2001, Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus, J Nat Prod, 64, 462, 10.1021/np000457m Hosoda, 2013, Regioselective hydroxylation and glucosylation of flavanones with cultured plant cells of Eucalyptus perriniana, Nat Prod Commun, 8, 905 Ibrahim, 1990, Microbiological transformation of flavone and isoflavone, Xenobiotica, 20, 363, 10.3109/00498259009046853 Ibrahim, 2003, O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans, Chem Pharm Bull, 51, 203, 10.1248/cpb.51.203 Ibrahim, 2010, Microbial metabolism of cannflavin A and B isolated from Cannabis sativa, Phytochemistry, 71, 1014, 10.1016/j.phytochem.2010.02.011 Ibrahim, 2005, Biotransformation of chrysin and apigenin by Cunninghamella elegans, Chem Pharm Bull, 53, 671, 10.1248/cpb.53.671 Jassbi, 2004, Antioxidant study and assignments of NMR spectral data for 3′,4′,7-trihydroxyflavanone 3′,7-di-O-β-D-glucopyranoside (butrin) and its hydrolyzed product, Chem Nat Comp, 40, 250, 10.1023/B:CONC.0000039134.46227.1f Katayama, 2013, Apple polyphenols suppress antigen presentation of ovalbumin by THP–1–derived dendritic cells, Food Chem, 138, 757, 10.1016/j.foodchem.2012.10.076 Kimura, 2013, 6-Demethoxynobiletin, a nobiletin-analog citrus flavonoid, enhances extracellular signal-regulated kinase phosphorylation in PC12D cells, Biol Pharm Bull, 36, 1646, 10.1248/bpb.b13-00230 Kim, 2013, Galangin attenuates mast cell-mediated allergic inflammation, Food Chem Toxicol, 57, 209, 10.1016/j.fct.2013.03.015 Kim, 2010, Biotransformation of flavonoid compounds; phloretin and chrysin, using Streptomyces species, J Biotechnol, 150, S347, 10.1016/j.jbiotec.2010.09.382 Kim, 2014, Dietary supplementation of chardonnay grape seed flour reduces plasma cholesterol concentration, hepatic steatosis, and abdominal fat content in high-fat diet-induced obese hamsters, J Agric Food Chem, 62, 1919, 10.1021/jf404832s Kostrzewa–Susłow, 2012, Microbial transformations of 7-hydroxyflavanone, Sci World J, 10.1100/2012/254929 Kostrzewa–Susłowa, 2006, Microbial transformations of flavanone and 6-hydroxyflavanone by Aspergillus niger strains, J Mol Catal B Enzym, 39, 18, 10.1016/j.molcatb.2006.01.020 Kostrzewa–Susłow, 2012, Microbial transformations of 7-methoxyflavanone, Molecules, 17, 14810, 10.3390/molecules171214810 Kostrzewa–Susłow, 2014, Microbial transformations of 3-methoyflavone by strains of Aspergillus niger, Pol J Microbiol, 63, 111, 10.33073/pjm-2014-016 Kostrzewa–Susłow, 2014, Enantioselective conversion of certain derivatives of 6-hydroxyflavanone, J Mol Catal B, 02, 59, 10.1016/j.molcatb.2014.01.013 Kostrzewa–Susłow, 2010, Microbial transformation of selected flavanones as a method of increasing the antioxidant properties. Z Naturforsch C, J Biosci, 65, 55 Kostrzewa–Susłowa, 2008, Microbial transformations of flavanone by Aspergillus niger and Penicillium chermesinum cultures, J Mol Catal B Enzym, 52–53, 34, 10.1016/j.molcatb.2008.01.002 Lai, 2013, Advances on biotransformation of flavonoid compounds, Agric Sci, 4, 95 Li, 2014, Bioaccessibility, in vitro antioxidant activities and in vivo anti-inflammatory activities of a purple tomato (Solanum lycopersicum L.), Food Chem, 159, 353, 10.1016/j.foodchem.2014.03.023 Liao, 2013, Flavonoids from Millettia nitida var. Hirsutissima with their anticoagulative activities and inhibitory effects on NO production, J Nat Med, 67, 856, 10.1007/s11418-013-0745-4 Lin, 2014, Production of quercetin, kaempferol and their glycosidic derivatives from the aqueous-organic extracted residue of litchi pericarp with Aspergillus awamori, Food Chem, 145, 220, 10.1016/j.foodchem.2013.08.048 Liu, 2013, Selective hydrolysis of flavonoid glycosides by Curvularia lunata, Chin J Nat Med, 11, 684, 10.3724/SP.J.1009.2013.00684 Liu, 2014, Dietary flavonoids intake and risk of type 2 diabetes: a meta-analysis of prospective cohort studies, Clin Nutr, 33, 59, 10.1016/j.clnu.2013.03.011 Lu, 2012, Biotransformation of rutin to quercetin by microorganisms, IOSR J Eng, 2, 70, 10.9790/3021-0217076 Ludwig-Müller, 2014, Improvement of hairy root cultures and plants by changing biosynthetic pathways leading to pharmaceutical metabolites: strategies and applications, Biotechnol Adv, 32, 1168, 10.1016/j.biotechadv.2014.03.007 Luo, 2014, Biotransformation of bavachinin by three fungal cell cultures, J Biosci Bioeng, 117, 191, 10.1016/j.jbiosc.2013.08.001 Ma, 2010, Preparative isolation and purification of four prenylflavanones from microbial biotransformation of kurarinone by high-speed counter-current chromatography, Sep Purif Technol, 76, 140, 10.1016/j.seppur.2010.09.033 Mamadalieva, 2011, El–Readi MZ, Tahrani A, Hamoud R, Egamberdieva DR, et al. Flavonoids in Scutellaria immaculata and S. ramosissima (Lamiaceae) and their biological activity, J Pharm Pharmacol, 63, 1346, 10.1111/j.2042-7158.2011.01336.x Marín, 2013, Recent trends in the pharmacological activity of isoprenyl phenolics, Curr Med Chem, 20, 272, 10.2174/092986713804806676 Miyazawa, 2004, Biotransformation of isoflavones by Aspergillus niger, as biocatalyst, J Mol Catal B, 27, 91, 10.1016/j.molcatb.2003.09.008 Miyazawa, 2006, Biotransformation of isoflavones by Aspergillus niger as biocatalyst, J Chem Technol Biotechnol, 81, 674, 10.1002/jctb.1461 Mohamed, 2008, Biotransformation of glabratephrin, a rare type of isoprenylated flavonoids by Aspergillus niger, Z Naturforsch C, 63, 561, 10.1515/znc-2008-7-816 Nielsen, 1998, In vitro biotransformation of flavonoids by rat liver microsomes, Xenobiotica, 28, 389, 10.1080/004982598239498 Ogungbe, 2014, Antileishmanial phytochemical phenolics: molecular docking to potential protein targets, J Mol Graph Model, 48, 105, 10.1016/j.jmgm.2013.12.010 Okuno, 2004, Biotransformation of nobiletin by Aspergillus niger and the antimutagenic activity of a metabolite, 4′-hydroxy-5,6,7,8,3′-pentamethoxyflavone, J Nat Prod, 67, 1876, 10.1021/np034007g Okuno, 2006, Microbial O-demethylation of sinesetin and antimutagenic activity of the metabolite, J Chem Technol Biotechnol, 81, 29, 10.1002/jctb.1353 Pervaiz, 2013, Microbial biotransformation: a tool for drug designing, Appl Biochem Microbiol, 49, 437, 10.1134/S0003683813050098 Pham, 2008, Effect of lactulose on biotransformation of isoflavone glycosides to aglycones in soymilk by lactobacilli, J Food Sci, 73, M158, 10.1111/j.1750-3841.2008.00687.x Pham, 2008, Skim milk powder supplementation affects lactose utilization, microbial survival and biotransformation of isoflavone glycosides to isoflavone aglycones in soymilk by Lactobacillus, Food Microbiol, 25, 653, 10.1016/j.fm.2008.04.004 Pham, 2008, Effect of lactulose supplementation on the growth of bifidobacteria and biotransformation of isoflavone glycosides to isoflavone aglycones in soymilk, J Agric Food Chem, 56, 4703, 10.1021/jf072716k Pham, 2007, Biotransformation of isoflavone glycosides by Bifidobacterium animalis in soymilk supplemented with skim milk powder, J Food Sci, 72, M316, 10.1111/j.1750-3841.2007.00476.x Plaza, 2014, Substituent effects on in vitro antioxidizing properties, stability, and solubility in flavonoids, J Agric Food Chem, 62, 3321, 10.1021/jf405570u Roh, 2009, Regioselective hydroxylation of isoflavones by Streptomyces avermitilis MA-4680, J Biosci Bioeng, 108, 41, 10.1016/j.jbiosc.2009.02.021 Salomon, 2012, Natural products as leads for tuberculosis drug development, Curr Top Med Chem, 12, 735, 10.2174/156802612799984526 Sanchez–Gonzalez, 2004, Microbial transformations of chalcones: hydroxylation, O-demethylation, and cyclization to flavanones, J Nat Prod, 67, 553, 10.1021/np030448o Sanchez–Gonzalez, 2006, Biocatalytic synthesis of butein and sulfuretin by Aspergillus alliaceus, J Agric Food Chem, 54, 4646, 10.1021/jf060900k Santos, 2013, Nanoencapsulation of polyphenols for protective effect against colon–rectal cancer, Biotechnol Adv, 31, 514, 10.1016/j.biotechadv.2012.08.005 Savi, 2010, Evaluation of antirotavirus activity of flavonoids, Fitoterapia, 81, 1142, 10.1016/j.fitote.2010.07.017 Schnekenburger, 2014, Plant-derived epigenetic modulators for cancer treatment and prevention, Biotechnol Adv, 32, 1123, 10.1016/j.biotechadv.2014.03.009 Seo, 2011, Flavonoids biotransformation by bacterial non-heme dioxygenases, biphenyl and naphthalene dioxygenase, Appl Microbiol Biotechnol, 91, 219, 10.1007/s00253-011-3334-z Shi, 2012, Microbial transformation of norkurarinone by Cunninghamella blakesleana AS 3.970, J Asian Nat Prod Res, 14, 906, 10.1080/10286020.2012.702759 Shi, 2012, Microbial biotransformation of kurarinone by Cunninghamella echinulata AS 3.3400, J Asian Nat Prod Res, 14, 1002, 10.1080/10286020.2012.681049 Shimoda, 2010, Biotransformation of naringin and naringenin by cultured Eucalyptus perriniana cells, Phytochemistry, 71, 201, 10.1016/j.phytochem.2009.09.035 Sisa, 2010, Photochemistry of flavonoids, Molecules, 15, 5196, 10.3390/molecules15085196 Stompor, 2013, Microbial synthesis of dihydrochalcones using Rhodococcus and Gordonia species, J Mol Catal B Enzym, 97, 283, 10.1016/j.molcatb.2013.09.009 Stompor, 2013, Microbiological reduction of xanthohumol and 4-methoxychalcone, Przem Chem, 92, 574 Sumarna, 2010, Hydrolysis of bioactive isoflavone in soymilk fermented with β-glucosidase producing lactic acid bacteria from local fermented foods of Indonesian, Malays J Microbiol, 6, 30 Swathi, 2012, Biotransformation of hesperidine to hesperitine by Cunninghamella elegans, Asian J Pharm Clin Res, 5, 174 Tronina, 2013, Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro, Bioorg Med Chem, 21, 2001, 10.1016/j.bmc.2013.01.026 Tronina, 2014, Transformation of xanthohumol by Aspergillus ochraceus, J Basic Microbiol, 54, 66, 10.1002/jobm.201200320 Walle, 2007, Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass?, Semin Cancer Biol, 17, 354, 10.1016/j.semcancer.2007.05.002 Wang, 2010, New progress in biocatalysis and biotransformation of flavonoids, J Med Plants Res, 4, 847 Wang, 2005, Biotransformation of flavonoids by Streptomyces griseus ATCC 13273, Pharm Biotechnol, 12, 308 Xi, 2014, Flavonoid composition and antioxidant activities of Chinese local pummelo (Citrus grandis Osbeck.) varieties, Food Chem, 161, 230, 10.1016/j.foodchem.2014.04.001 Xiao, 2013, Natural products for treatment of Alzheimer's disease and related diseases: understanding their mechanism of action, Curr Neuropharmacol, 11, 337, 10.2174/1570159X11311040001 Xiao, 2013, Advance in dietary polyphenols as α-glucosidases inhibitors: a review on structure–activity relationship aspect, Crit Rev Food Sci Nutr, 53, 818, 10.1080/10408398.2011.561379 Xiao, 2013, A review on structure–activity relationship of dietary polyphenols inhibiting α-amylase, Crit Rev Food Sci Nutr, 53, 497, 10.1080/10408398.2010.548108 Xiao, 2014, Flavonoid glycosylation and biological benefits, Biotechnol Adv, 10.1016/j.biotechadv.2014.05.004 Xiao, 2014, Advance on biotechnology for glycosylation of high-value flavonoids, Biotechnol Adv, 32, 1145, 10.1016/j.biotechadv.2014.04.006 Xiao, 2014, Influence of diabetes on the pharmacokinetic behavior of natural polyphenols, Curr Drug Metab, 15, 23, 10.2174/1389200214666131210142614 Xiao, 2014, Dietary polyphenols and type 2 diabetes: current insights and future perspectives, Curr Med Chem, 10.2174/0929867321666140706130807 Xiao, 2015, Advance in dietary polyphenols as aldose reductases inhibitors: structure–activity relationship aspect, Crit Rev Food Sci Nutr, 55, 15, 10.1080/10408398.2011.584252 Xiang, 2010, Isolation and identification of chlorinated genistein from Actinoplanes sp. HBDN08 with antioxidant and antitumor activities, J Agric Food Chem, 58, 1933, 10.1021/jf9035194 Ye, 2007, Biotransformation of puerarin into 3′-hydroxypuerarin by Trichoderma harzianum NJ01, Enzyme Microb Technol, 40, 594, 10.1016/j.enzmictec.2006.05.016 You, 2010, Transformation of rutin to antiproliferative quercetin 3-glucoside by Aspergillus niger, J Agric Food Chem, 58, 10886, 10.1021/jf102871g