An efficient glucosylation of alcoholic hydroxyls in the structures of protostane triterpenoids catalyzed by fungus has been developed. Four protostanes 1-4 as the substrates have been transformed by Syncephalastrum racemosum AS 3.264 and generated corresponding 11-OH glucosylation derivatives. The regioselective characteristics were also identified by various highly oxygenated protostane substrates. The time-courses displayed the highest yields of 1a, 3a, and 4a at > 50%, and 1a had the highest yield of 72%. All of the protostane analogues displayed hCE-2 inhibitory effects in an in vitro bioassay. This report describes a rare biocatalytic alcoholic hydroxyl glucosylation with considerable yield and regioselective characteristics.
glucosylation, alcoholic hydroxyls, protostane triterpenoid, Syncephalastrum racemosum AS 3.264
Publication DOI: 10.1016/j.catcom.2016.10.025Journal NLM ID: 101126473Publisher: Amsterdam, New York: Elsevier
Correspondence: Wang W
; Ma X
Institutions: TCM and Ethnomedicine Innovation & Development Laboratory, School of Pharmacy, Hunan University of Chinese Medicine, Changsha, China, College of Pharmacy, Research Institute of Integrated Traditional and Western Medicine, Dalian Medical University, Dalian, China
Methods: 13C NMR, 1H NMR, ESI-MS, LC-ESI-MS, HR-ESI-MS, HMBC, HPLC-DAD
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