- Biosynthesis of novel daidzein derivatives using Bacillus amyloliquefaciens whole cells
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Biotransformation of daidzein was performed by using Bacillus amyloliquefaciens KCTC 13588, Lactococcus lactis subsp. lactis KCTC 3769, Leuconostoc citreum KCTC 13186, Kluyveromyces lactis var. lactis KCTC 17704, Pediococcus pentosaceus KCTC 3116, and Lac
- Kim, Kyu-Min,Park, Jin-Soo,Choi, HaeRi,Kim, Min-Seon,Seo, Joo-Hyun,Pandey, Ramesh Prasad,Kim, Jin Woo,Hyun, Chang-Gu,Kim, Seung-Young
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- Synthesis of daidzein glycosides, α-tocopherol glycosides, hesperetin glycosides by bioconversion and their potential for anti-allergic functional-foods and cosmetics
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Daidzein is a common isoflavone, having multiple biological effects such as anti-inflammation, anti-allergy, and anti-aging. α-Tocopherol is the tocopherol isoform with the highest vitamin E activity including anti-allergic activity and anti-cancer activity. Hesperetin is a flavone, which shows potent anti-inflammatory effects. These compounds have shortcomings, i.e., water-insolubility and poor absorption after oral administration. The glycosylation of bioactive compounds can enhance their water-solubility, physicochemical stability, intestinal absorption, and biological half-life, and improve their bio- and pharmacological properties. They were transformed by cultured Nicotiana tabacum cells to 7-β-glucoside and 7-β-gentiobioside of daidzein, and 30- and 7-β-glucosides, 30,7-β-diglucoside, and 7-β-gentiobioside of hesperetin. Daidzein and α-tocopherol were glycosylated by galactosylation with β-glucosidase to give 40- and 7-β-galactosides of daidzein, which were new compounds, and α-tocopherol 6-β-galactoside. These nine glycosides showed higher anti-allergic activity, i.e., inhibitory activity toward histamine release from rat peritoneal mast cells, than their respective aglycones. In addition, these glycosides showed higher tyrosinase inhibitory activity than the corresponding aglycones. Glycosylation of daidzein, α-tocopherol, and hesperetin greatly improved their biological activities.
- Fujitaka, Yuya,Hamada, Hiroki,Uesugi, Daisuke,Kuboki, Atsuhito,Shimoda, Kei,Iwaki, Takafumi,Kiriake, Yuya,Saikawa, Tomohiro
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- Molecular and Structural Characterization of a Promiscuous C-Glycosyltransferase from Trollius chinensis
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Herein, the catalytic promiscuity of TcCGT1, a new C-glycosyltransferase (CGT) from the medicinal plant Trollius chinensis is explored. TcCGT1 could efficiently and regio-specifically catalyze the 8-C-glycosylation of 36 flavones and other flavonoids and could also catalyze the O-glycosylation of diverse phenolics. The crystal structure of TcCGT1 in complex with uridine diphosphate was determined at 1.85 ? resolution. Molecular docking revealed a new model for the catalytic mechanism of TcCGT1, which is initiated by the spontaneous deprotonation of the substrate. The spacious binding pocket explains the substrate promiscuity, and the binding pose of the substrate determines C- or O-glycosylation activity. Site-directed mutagenesis at two residues (I94E and G284K) switched C- to O-glycosylation. TcCGT1 is the first plant CGT with a crystal structure and the first flavone 8-C-glycosyltransferase described. This provides a basis for designing efficient glycosylation biocatalysts.
- He, Jun-Bin,Zhao, Peng,Hu, Zhi-Min,Liu, Shuang,Kuang, Yi,Zhang, Meng,Li, Bin,Yun, Cai-Hong,Qiao, Xue,Ye, Min
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supporting information
p. 11513 - 11520
(2019/07/16)
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- Exploring the aglycon promiscuity of a new glycosyltransferase from Pueraria lobata
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Enzymatic glycosylation catalyzed by glycosyltransferases has great potential for creating bioactive glycosylated small-molecule compounds. Here, we highlight the aglycon promiscuity of a new glycosyltransferase (PlGT7) from Pueraria lobata. PlGT7 exhibited the capability to glycosylate 26 structurally diverse drug-like scaffolds and simple phenolics with UDP-glucose to form O-, S-, and N-glycosides. The reversibility of PlGT7 coupled with its substrate flexibility was also exploited to generate bioactive glucosides with simple sugar donor. These studies indicate the significant potential of an enzymatic approach to the glycosylation of bioactive natural and unnatural products in drug discovery.
- Sun, Lili,Chen, Dawei,Chen, Ridao,Xie, Kebo,Liu, Jimei,Yang, Lin,Dai, Jungui
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supporting information
p. 1518 - 1521
(2016/03/12)
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- Assessing the regioselectivity of oleD-catalyzed glycosylation with a diverse set of acceptors
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To explore the acceptor regioselectivity of OleD-catalyzed glucosylation, the products of OleD-catalyzed reactions with six structurally diverse acceptors flavonesnY (daidzein), isoflavones (flavopiridol), stilbenes (resveratrol), indole alkaloids (10-hydroxycamptothecin), and steroids (2- methoxyestradiol)- were determined. This study highlights the first synthesis of flavopiridol and 2-methoxyestradiol glucosides and confirms the ability of OleD to glucosylate both aromatic and aliphatic nucleophiles. In all cases, molecular dynamics simulations were consistent with the determined product distribution and suggest the potential to develop a virtual screening model to identify additional OleD substrates.
- Zhou, Maoquan,Hamza, Adel,Zhan, Chang-Guo,Thorson, Jon S.
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p. 279 - 286
(2013/06/05)
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- Synthesis of β-maltooligosaccharides of glycitein and daidzein and their anti-oxidant and anti-allergic activities
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The production of β-maltooligosaccharides of glycitein and daidzein using Lactobacillus delbrueckii and cyclodextrin glucanotransferase (CGTase) as biocatalysts was investigated. The cells of L. delbrueckii glucosylated glycitein and daidzein to give their corresponding 4′- and 7-O-β-glucosides. The β-glucosides of glycitein and daidzein were converted into the corresponding β-maltooligosides by CGTase. The 7-O-β- glucosides of glycitein and daidzein and 7-O-β-maltoside of glycitein showed inhibitory effects on IgE antibody production. On the other hand, β-glucosides of glycitein and daidzein exerted 2,2-diphenyl-1- picrylhydrazyl (DPPH) free-radical scavenging activity and supeoxide-radical scavenging activity.
- Shimoda, Kei,Hamada, Hiroki
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experimental part
p. 5153 - 5161
(2011/02/21)
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- An efficient method for the glycosylation of isoflavones
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The isoflavone phytoestrogens are still of current interest for their positive and negative health benefits. However, there are still many unanswered questions regarding their absorption, metabolism and bioavailability. Studies in this area require access to samples of both the isoflavone 7-O-glucosides, the form found in plants and the 7-O-glucuronides, which are important mammaliam metabolites. A new efficient, high-yielding glycosylation procedure is described for isoflavones, which employs 2,2,2-trifluoro-N-(p-methoxyphenyl) acetamidates as the glycosyl donors. This methodology was used to prepare the 7-O-glycosides of the three main isoflavones, daidzein, genistein and glycitein. The isoflavones were protected with hexanoyl groups which improved their solubility in organic solvents and improved the efficiency of the reaction. The same methodology was then adapted for the synthesis of the analogous 7-O-glucuronides. The new synthesis will provide access to large quantities of these compounds for further biological studies. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Al-Maharik, Nawaf,Botting, Nigel P.
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experimental part
p. 5622 - 5629
(2009/05/27)
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- Kinetic modeling of malonylgenistin and malonyldaidzin conversions under alkaline conditions and elevated temperatures
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The conversion and degradation of malonylglucosides were kinetically characterized under elevated pH/heat conditions. Malonylgenistin and malonyldaidzin were heated at 60, 80, and 100°C and pH values of 8.5, 9, and 9.5. A simple kinetic model was developed, which adequately predicted the conversion and degradation reactions. The conversion and degradation rates increased as temperature and pH increased. The rates of conversion of both malonylglucosides into their respective β-glucosides were comparable under all pH/heat treatments. However, at 100°C, the rates of degradation of malonyldaidzin were approximately double those of malonylgenistin, under all pH treatments. When malonlydaidzin was heated at 100°C and pH 9.5, degradation of the produced daidzin occurred. Therefore, an alternative kinetic model was developed to better predict the conversion and degradation of malonyldaidzin occurring at 100°C and pH 9.5. The models developed provide soy food manufacturers with guidelines for better control of the profile and level of isoflavones.
- Vaidya, Nirupama A.,Mathias, Kevin,Ismail, Baraem,Hayes, Kirby D.,Corvalan, Carlos M.
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p. 3408 - 3413
(2008/02/07)
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- Regioselective glucosylation of aromatic compounds: Screening of a recombinant glycosyltransferase library to identify biocatalysts
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(Chemical Equation Presented) A novel whole-cell screen for the identification of new glucosyltransferase (GT) biocatalysts within a recombinant enzyme library was developed. Following biotransformation, levels of D-glucose were used as a measure of biocatalysis. Twenty five enzymes that transfer D-glucose to trans-resveratrol were identified that have the regioselectivity shown in the picture.
- Weis, Markus,Lim, Eng-Kiat,Bruce, Neil,Bowles, Dianna
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p. 3534 - 3538
(2007/10/03)
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- METHOD FOR PURIFYING AND SEPARATING SOY ISOFLAVONES
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A method for purifying isoflavones glycosides of genistin and daidzin from impurities present in a soy isoflavones concentrate. The method includes digesting a soy isoflavones concentrate with an acidic solution and separating insoluble solids from the acidic solution, wherein the solids are enriched in genistin and comprise glycosides of genistin and daidzin.
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- Facile synthesis of flavonoid 7-O-glycosides
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Highly regioselective removal of the 7-O-acyl groups of the peracylated flavones, isoflavones, and flavonols (PhSH, imidazole, NMP) followed by effective glycosylation with glycosyl trifluoroacetimidates (BF 3·Et2O) and cautious deprotection of the acyl groups under basic conditions afforded the desired 7-O-flavonoid glycosides in satisfactory yields.
- Li, Ming,Han, Xiuwen,Yu, Biao
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p. 6842 - 6845
(2007/10/03)
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- The phase transfer catalysed synthesis of isoflavone-O-glucosides
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Daidzin 1, genistin 2, ononin 3 and sissotrin 4 are the major products of the phase transfer catalysed reaction between the isoflavone aglycones daidzein, genistein, formononetin and biochanin A, respectively, and 1-bromo-2,3,4,6-tetra-O-acetyl-α-glucopyranose. Complete proton and carbon NMR assignments are presented for compounds 1-4.
- Lewis, Philip,Kaltia, Seppo,Waehaelae, Kristiina
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p. 2481 - 2484
(2007/10/03)
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- Process for the isolation and purification of isoflavones
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The present invention relates to a process for the isolation and purification of isoflavones from a number of different biomass sources. More particularly, the present invention relates to a three-step process whereby a biomass containing isoflavones with a solvent thereby forming an extract that is subsequently fractionated using a reverse phase matrix in combination with a step gradient elution, wherein the resulting fractions eluted from the column contain specific isoflavones that are later crystallized. The purified isoflavone glycosides may then be hydrolyzed to their respective aglycone.
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- Phenolic glucosides from the root of Pueraria lobata
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Six phenolic glucosides were isolated from the methanolic extract of the root of Pueraria lobata. Three of them were new compounds and their structures were proved to be kuzubutenolide A, 3'-hydroxy-4'-O-β-D- glucosylpuerarin and 3'-methoxydaidzin.
- Hirakura, Kazuhiro,Morita, Makoto,Nakajima, Kaoru,Sugama, Koh,Takagi, Koji,Niitsu, Kazuaki,Ikeya, Yukinobu,Maruno, Masao,Okada, Minoru
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p. 921 - 928
(2007/10/03)
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- SYNTHESIS OF 7-O-β-D-GLUCOPYRANOSIDES OF ISOFLAVONES AND THEIR HETEROCYCLIC ANALOGUES
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The products of the interaction of α-acetobromoglucose with 2,4,5-trihydroxyphenyl benzyl ketone and 2,4-dihydroxyphenyl 4'-hydroxybenzyl ketone and also with their heterocyclic analogues, which are present completely or partially in the enolic form, have been investigated.It has been shown that in this reaction a tetra-O-acetylglucosyl residue is added at the 4-OH hydroxy group of the phenyl residue of the ketone.The compounds obtained have been converted into isoflavone 7-O-glucosides by the action of the Vilsmeier reagent or acetoformic anhydride.
- Pivovarenko, V. G.,Khilya, V. P.
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p. 181 - 186
(2007/10/02)
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- Isoflavone glucosides exist as their 6''-O-malonyl esters in Pueraria lobata and its cell suspension cultures
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Methanol extracts prepared by mild and careful procedure from cultured cells of P. lobata were analyzed by reverse phase high performance liquid chromatography (HPLC) to reveal that most of the isoflavone 7-O-glucosides daidzin(1) and genistin(2), and 8-C-glucoside puerarin(3), exiost as their 6''-O-malonyl esters. The presence of malonyl esters of 1, 2 and 3 was also detected in the fresh roots and stems of P. lobata.
- Park,Hakamatsuka,Noguchi,Sankawa,Ebizuka
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p. 1978 - 1980
(2007/10/02)
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