One-Pot Bi-Enzymatic Cascade Synthesis of Novel Ganoderma Triterpenoid Saponins

Catalysts

Tzi-Yuan Wang¹  Te-Sheng Chang²  Yu-Li Tsai²  Huei-Ju Ting²  Jiumn-Yih Wu³  Chien-Min Chiang⁴  Yu-Wei Wu⁵ 

[1] Biodiversity Research Center, Academia Sinica, Taipei 115, Taiwan;Department of Biological Sciences and Technology, National University of Tainan, Tainan 70005, Taiwan;Department of Food Science, National Quemoy University, Kinmen County 892, Taiwan;Department of Pharmacy, Chia Nan University of Pharmacy and Science, No. 60, Sec. 1, Erh-Jen Rd., Jen-Te District, Tainan 71710, Taiwan;Graduate Institute of Biomedical Informatics, College of Medical Science and Technology, Taipei Medical University, Taipei 106, Taiwan;

关键词: Ganoderma lucidum;    ganoderic acid A;    triterpenoid;    glycosyltransferase;    cyclodextrin glucanotransferase;    saponin;   

DOI  :  10.3390/catal11050580

来源: DOAJ

【 摘 要 】

Ganoderma lucidum is a medicinal fungus whose numerous triterpenoids are its main bioactive constituents. Although hundreds of Ganoderma triterpenoids have been identified, Ganoderma triterpenoid glycosides, also named triterpenoid saponins, have been rarely found. Ganoderic acid A (GAA), a major Ganoderma triterpenoid, was synthetically cascaded to form GAA-15-O-β-glucopyranoside (GAA-15-G) by glycosyltransferase (BtGT_16345) from Bacillus thuringiensis GA A07 and subsequently biotransformed into a series of GAA glucosides by cyclodextrin glucanotransferase (Toruzyme^® 3.0 L) from Thermoanaerobacter sp. The optimal reaction conditions for the second-step biotransformation of GAA-15-G were found to be 20% of maltose; pH 5; 60 °C. A series of GAA glucosides (GAA-G2, GAA-G3, and GAA-G4) could be purified with preparative high-performance liquid chromatography (HPLC) and identified by mass and nucleic magnetic resonance (NMR) spectral analysis. The major product, GAA-15-O-[α-glucopyranosyl-(1→4)-β-glucopyranoside] (GAA-G2), showed over 4554-fold higher aqueous solubility than GAA. The present study demonstrated that multiple Ganoderma triterpenoid saponins could be produced by sequential actions of BtGT_16345 and Toruzyme^®, and the synthetic strategy that we proposed might be applied to many other Ganoderma triterpenoids to produce numerous novel Ganoderma triterpenoid saponins in the future.

【 授权许可】

Unknown