Novel protostane-type triterpenoids with inhibitory human carboxylesterase 2 activities. Issue 46 (31st May 2017)

• Record Type: Journal Article
• Authors: Zhang, Zhi-Jie; Huo, Xiao-Kui; Tian, Xiang-Ge; Feng, Lei; Ning, Jing; Zhao, Xin-Yu; Sun, Cheng-Peng; Wang, Chao; Deng, Sa; Zhang, Bao-Jing; Zhang, Hou-Li; Liu, Yong
• Is Part Of: RSC advances. Volume 7:Issue 46(2017)
• Page Start: 28702
• Page End: 28710
• Publication Date: 2017-05-31
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7ra04841f
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Ten new triterpenoids, including two novel nor -protostanes, were isolated from A. orientalis and biotransformation of alisols A and B 23-acetate. Abstract : The rhizomes of Alisma orientalis have been used for centuries in China and other Asian countries as an effective herbal remedy. The phytochemical investigation of A. orientalis and biotransformation of two major triterpenoids alisols A (11 ) and B 23-acetate (13 ) by Cunninghamella elagans AS 3.2028 and Penicillium janthinellum AS 3.510 have led to the isolation of ten new protostane-type triterpenoids (1–5 and18–22 ), including one novel 26- nor -protostane (1 ) and one unusual 17- nor -protostane (2 ), together with twelve known analogues. Their structures were determined by 1D and 2D NMR, and HRESIMS spectroscopic analyses. All the isolated compounds were assayed for their inhibitory activities against human carboxylesterase 2 (HCE-2). Compounds1, 3–9, 12, 14–16, 19, and20 showed significant inhibitory activities on HCE-2 with IC50 values from 0.51 ± 0.09 μM to 9.45 ± 0.73 μM. The inhibition kinetics of compound5 toward HCE-2 were established, and its K i value was determined as 0.57 μM. The interaction of compound5 with HCE-2 was investigated using molecular docking.