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    標題: A New Triterpenoid Glucoside from a Novel Acidic Glycosylation of Ganoderic Acid A via Recombinant Glycosyltransferase of Bacillus subtilis
    作者: Chang, Te-Sheng
    Chien-Min Chiang(江建民)
    Kao, Yu-Han
    Wu, Jiumn-Yih
    Wu, Yu-Wei
    Wang, Tzi-Yuan
    貢獻者: Natl Univ Tainan, Dept Biol Sci & Technol
    Chia Nan Univ Pharm & Sci, Dept Biotechnol
    Natl Quemoy Univ, Dept Food Sci, Jinning 892, Kinmen County, Taiwan
    Taipei Med Univ, Coll Med Sci & Technol, Grad Inst Biomed Informat
    Taipei Med Univ Hosp, Clin Big Data Res Ctr
    Acad Sinica, Biodivers Res Ctr
    關鍵字: ganoderic acid A
    glucosyltransferase
    acidic
    Bacillus subtilis
    triterpenoid
    日期: 2019-10
    上傳時間: 2020-07-29 13:51:03 (UTC+8)
    出版者: MDPI
    摘要: Ganoderic acid A (GAA) is a bioactive triterpenoid isolated from the medicinal fungus Ganoderma lucidum. Our previous study showed that the Bacillus subtilis ATCC (American type culture collection) 6633 strain could biotransform GAA into compound (1), GAA-15-O-beta -glucoside, and compound (2). Even though we identified two glycosyltransferases (GT) to catalyze the synthesis of GAA-15-O-beta -glucoside, the chemical structure of compound (2) and its corresponding enzyme remain elusive. In the present study, we identified BsGT110, a GT from the same B. subtilis strain, for the biotransformation of GAA into compound (2) through acidic glycosylation. BsGT110 showed an optimal glycosylation activity toward GAA at pH 6 but lost most of its activity at pH 8. Through a scaled-up production, compound (2) was successfully isolated using preparative high-performance liquid chromatography and identified to be a new triterpenoid glucoside (GAA-26-O-beta -glucoside) by mass and nuclear magnetic resonance spectroscopy. The results of kinetic experiments showed that the turnover number (k(cat)) of BsGT110 toward GAA at pH 6 (k(cat) = 11.2 min(-1)) was 3-fold higher than that at pH 7 (k(cat) = 3.8 min(-1)), indicating that the glycosylation activity of BsGT110 toward GAA was more active at acidic pH 6. In short, we determined that BsGT110 is a unique GT that plays a role in the glycosylation of triterpenoid at the C-26 position under acidic conditions, but loses most of this activity under alkaline ones, suggesting that acidic solutions may enhance the catalytic activity of this and similar types of GTs toward triterpenoids.
    關聯: Molecules, v.24, n.19, 3457
    Appears in Collections:[生物科技系(所)] 期刊論文

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