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A New Triterpenoid Glucoside From a Novel Acidic Glycosylation of Ganoderic Acid A via Recombinant Glycosyltransferase of

A New Triterpenoid Glucoside From a Novel Acidic Glycosylation of Ganoderic Acid A via Recombinant Glycosyltransferase of

Te-Sheng Chang, Chien-Min Chiang, Yu-Han Kao, Jiumn-Yih Wu, Yu-Wei Wu, Tzi-Yuan Wang

Molecules. 2019 Sep 24;24(19):3457.

PMID: 31554155

Abstract:

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-β-glucoside, and compound (2). Even though we identified two glycosyltransferases (GT) to catalyze the synthesis of GAA-15-O-β-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-β-glucoside) by mass and nuclear magnetic resonance spectroscopy. The results of kinetic experiments showed that the turnover number (kcat) of BsGT110 toward GAA at pH 6 (kcat = 11.2 min-1) was 3-fold higher than that at pH 7 (kcat = 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP81907622	Ganoderic acid A		81907-62-2	Price

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