Genistein is the principal isoflavone constituent of soybean. It has attracted more attention than other plant polyphenols because of its significant affinity with medical interests. Herein, we biosynthesized and structurally characterized ten different natural and non-natural analogues of genistein glycopyranosides using versatile glycosyltransferases (GTs) and sugar-O-methyltransferases (SOMTs). Two GTs, AtUGT89C1 from the Arabidopsis thaliana plant and YjiC from Bacillus licheniformis DSM-13 bacteria, catalyzed the glycosylation reaction. Two SOMTs transferred the methyl group to two specific hydroxy positions in the sugar moiety of genistein rhamnopyranoside, thus diversifying the sugar attached to genistein. Among the biosynthesized compounds, four of the 2-deoxy-D-glycopyranosides, 7-O-(2-deoxy-β-D-arabino-hexopyranosyl)genistein, 4′-O-(2-deoxy-β-D-arabino-hexopyranosyl)genistein, 4′,7-bis-O-(2-deoxy-β-D-arabino-hexopyranosyl)genistein, and 4′,5,7-tri-O-(2-deoxy-β-D-arabino-hexopyranosyl)genistein, and two of the O-methyl rhamnopyranosides, 7-O-(3-O-methyl-α-L-rhamnopyranosyl)genistein and 7-O-(4-O-methyl-α-L-rhamnopyranosyl)genistein, are novel compounds that have not been previously reported. The other glycopyranosides are 7-O-(α-L-rhamnopyranosyl)genistein, 7-O-(β-D-glucopyranosyl)genistein, 4′-O-(β-D-glucopyranosyl)genistein, and 4′,7-O-(β-D-glucopyranosyl)genistein. Microbial production of these novel compounds and other glucopyranosides is appreciable in shake flask culture. This study highlights the application of versatile enzymes in the production of diverse glycosides of medicinally important genistein, which can have positive impacts on a variety of molecular targets in future studies, as shown by genistein with remedied drawbacks.
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机译：金雀异黄素是大豆的主要异黄酮成分。与其他植物多酚相比，它与医学利益有着显着的亲和力，因此引起了更多关注。在这里，我们使用通用的糖基转移酶（GTs）和糖- O -甲基转移酶（SOMT）对金雀异黄素糖吡喃糖苷的十种不同的天然和非天然类似物进行了生物合成和结构表征。两种GTs，来自拟南芥植物的AtUGT89C1和来自地衣芽孢杆菌DSM-13细菌的YjiC催化了糖基化反应。两个SOMT将甲基转移到染料木黄酮鼠李吡喃糖苷的糖部分中的两个特定的羟基位置，从而使附着在染料木黄酮上的糖多样化。在生物合成的化合物中，2-脱氧- D -糖吡喃糖苷中有四个，7- O -（2-脱氧-β- D - 阿拉伯-己吡喃糖基）染料木黄酮，4'- O -（2-deoxy-β- D - arabino -六吡喃糖基）染料木黄酮，4'，7-双- O -（2-脱氧-β-<小> D -阿拉伯糖-六吡喃糖基）染料木黄酮和4'，5,7-tri- O -（2-deoxy-β- D - arabino -hexopyranosyl）genistein，and of the 2'，其中两个 O -甲基鼠李吡喃糖苷7- O -（3- O -甲基-α- L -鼠李糖吡喃糖基）染料木黄酮和7- O -（4- O -甲基-α- L -鼠李糖吡喃糖基）染料木黄酮是尚未被发现的新型化合物以前的报道。其他糖吡喃糖苷是7- O -（α- L -鼠李糖吡喃糖基）染料木黄酮，7- O -（β- D < / small>-吡喃葡萄糖基）金雀异黄素，4'- O -（β- D -吡喃葡萄糖基）金雀异黄素和4'，7- O -（β- D -吡喃葡萄糖基）染料木黄酮。这些新型化合物和其他吡喃葡萄糖苷的微生物生产在摇瓶培养中是可观的。这项研究强调了通用酶在具有医学重要性的染料木黄酮的多种糖苷生产中的应用，这可能会在未来的研究中对多种分子靶标产生积极影响，如染料木黄酮具有纠正的缺点。
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