Novel Diterpenoids from the Twigs of Podocarpus nagi

Yuan-Dong Zheng; Xing-Chen Guan; Dan Li; An-Qi Wang; Chang-Qiang Ke; Chun-Ping Tang; Li-Gen Lin; Yang Ye; Zheng-Liang Wang; Sheng Yao

doi:10.3390/molecules21101282

Novel Diterpenoids from the Twigs of Podocarpus nagi

Molecules. 2016 Sep 25;21(10):1282. doi: 10.3390/molecules21101282.

Authors

Yuan-Dong Zheng^{1

2

3}, Xing-Chen Guan⁴, Dan Li⁵, An-Qi Wang⁶, Chang-Qiang Ke^{7

8}, Chun-Ping Tang^{9

10}, Li-Gen Lin¹¹, Yang Ye^{12

13

14}, Zheng-Liang Wang⁴, Sheng Yao^{15

16}

Affiliations

¹ State Key Laboratory of Drug Research & Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. zhengyd@shanghaitech.edu.cn.
² University of Chinese Academy of Sciences, Beijing 100049, China. zhengyd@shanghaitech.edu.cn.
³ School of Life Science and Technology, ShanghaiTech University, Shanghai 201203, China. zhengyd@shanghaitech.edu.cn.
⁴ School of Chemistry & Environmental Engineering, Yangtze University, Jingzhou 434023, China. gxc911212@126.com.
⁵ State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macau 999078, China. yb47516@umac.mo.
⁶ State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macau 999078, China. yb37510@umac.mo.
⁷ State Key Laboratory of Drug Research & Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. kechangqiang@simm.ac.cn.
⁸ University of Chinese Academy of Sciences, Beijing 100049, China. kechangqiang@simm.ac.cn.
⁹ State Key Laboratory of Drug Research & Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. tangcp_sh@163.com.
¹⁰ University of Chinese Academy of Sciences, Beijing 100049, China. tangcp_sh@163.com.
¹¹ State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macau 999078, China. ligenl@umac.mo.
¹² State Key Laboratory of Drug Research & Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. yye@simm.ac.cn.
¹³ University of Chinese Academy of Sciences, Beijing 100049, China. yye@simm.ac.cn.
¹⁴ School of Life Science and Technology, ShanghaiTech University, Shanghai 201203, China. yye@simm.ac.cn.
¹⁵ State Key Laboratory of Drug Research & Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. yaosheng@simm.ac.cn.
¹⁶ University of Chinese Academy of Sciences, Beijing 100049, China. yaosheng@simm.ac.cn.

Abstract

Phytochemical investigation of the twigs of Podocarpus nagi (Podocarpaceae) led to the isolation of two new abietane-type diterpenoids, named 1β,16-dihydroxylambertic acid (1) and 3β,16-dihydroxylambertic acid (2), along with two new ent-pimarane-type diterpenoids, named ent-2β,15,16,18-tetrahydroxypimar-8(14)-ene (3) and ent-15-oxo-2β,16,18-trihydroxypimar-8(14)-ene (4). Their respective structures were elucidated on the basis of spectroscopic analyses, including 1D- and 2D-NMR, IR, CD, and HR-ESI-MS. This is the first time ent-pimarane-type diterpenoids from the genus Podocarpus has been reported. All four new compounds were tested for cytotoxic activity. The MTT assay results showed that compounds 3 and 4 significantly inhibited the proliferation of human cervical cancer Hela cells, human lung cancer A549 cells, and human breast cancer MCF-7 cells at a concentration of 10 μM. Furthermore, using the lipopolysaccharide (LPS)-stimulated RAW264.7 cells, compounds 2 and 4 were found to significantly inhibit nitrogen oxide (NO) production with IC50 values of 26.5 ± 6.1 and 17.1 ± 1.5 μM, respectively.

Keywords: Podocarpus nagi; abietane-type diterpenoid; anti-inflammation; cytotoxicity; ent-pimarane-type diterpenoid.