Novel C-17 spirost protostane-type triterpenoids from Alisma plantago-aquatica with anti-inflammatory activity in Caco-2 cells

Qinghao Jin; Jianqing Zhang; Jinjun Hou; Min Lei; Chen Liu; Xia Wang; Yong Huang; Shuai Yao; Bang Yeon Hwang; Wanying Wu; Dean Guo

doi:10.1016/j.apsb.2019.04.002

Novel C-17 spirost protostane-type triterpenoids from Alisma plantago-aquatica with anti-inflammatory activity in Caco-2 cells

Acta Pharm Sin B. 2019 Jul;9(4):809-818. doi: 10.1016/j.apsb.2019.04.002. Epub 2019 May 7.

Authors

Qinghao Jin¹, Jianqing Zhang^{1

2}, Jinjun Hou¹, Min Lei¹, Chen Liu¹, Xia Wang^{1

3}, Yong Huang¹, Shuai Yao¹, Bang Yeon Hwang⁴, Wanying Wu^{1

3}, Dean Guo^{1

2}

Affiliations

¹ Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
² School of Pharmacy, Shenyang Pharmaceutical University, Shenyang 110016, China.
³ University of Chinese Academy of Sciences, Beijing 100049, China.
⁴ College of Pharmacy, Chungbuk National University, Cheongju 2816, South Korea.

Abstract

Twenty-one protostane-type triterpenoids with diverse structures, including nine new compounds (1-9), were isolated from the of Alisma plantago-aquatica Linn. Structurally, alisolides A‒F (1-6), composed of an oxole group coupled to a five-membered ring, represent unusual C-17 spirost protostane-type triterpenoids. Alisolide H (8) is a novel triterpenoid with an unreported endoperoxide bridge. Alisolide I (9) represents the first example of 23,24-acetal triterpenoid. Their structures were elucidated based on spectroscopic analysis, wherein the absolute configurations of 4‒6, 8 were further confirmed by the Mo₂(OAc)₄-induced ECD method. Furthermore, all isolates were evaluated for their inhibitory effects on LPS-induced NO production in Caco-2 cells, and all the compounds showed remarkable inhibitory activities, with IC₅₀ values in the range of 0.76-38.20 μmol/L.

Keywords: Alisma plantago-aquatica Linn.; Caco-2 cells; LPS-induced NO production; Protostane-type triterpenoids.