Ent-Abietanoids Isolated from Isodon serra

Jun Wan; Hua-Yi Jiang; Jian-Wei Tang; Xing-Ren Li; Xue Du; Yan Li; Han-Dong Sun; Jian-Xin Pu

doi:10.3390/molecules22020309

Ent-Abietanoids Isolated from Isodon serra

Molecules. 2017 Feb 17;22(2):309. doi: 10.3390/molecules22020309.

Authors

Jun Wan^{1

2}, Hua-Yi Jiang^{3

4}, Jian-Wei Tang^{5

6}, Xing-Ren Li^{7

8}, Xue Du⁹, Yan Li¹⁰, Han-Dong Sun¹¹, Jian-Xin Pu¹²

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. wanjun@imm.ac.cn.
² Kunming College of Life Sciences, University of Chinese Academy of Sciences, Beijing 100039, China. wanjun@imm.ac.cn.
³ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. jianghuayi@mail.kib.ac.cn.
⁴ Kunming College of Life Sciences, University of Chinese Academy of Sciences, Beijing 100039, China. jianghuayi@mail.kib.ac.cn.
⁵ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. tangjianwei@mail.kib.ac.cn.
⁶ Kunming College of Life Sciences, University of Chinese Academy of Sciences, Beijing 100039, China. tangjianwei@mail.kib.ac.cn.
⁷ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. lixingren@mail.kib.ac.cn.
⁸ Kunming College of Life Sciences, University of Chinese Academy of Sciences, Beijing 100039, China. lixingren@mail.kib.ac.cn.
⁹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. duxue@mail.kib.ac.cn.
¹⁰ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. liyanb@mail.kib.ac.cn.
¹¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. hdsun@mail.kib.ac.cn.
¹² State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. pujianxin@mail.kib.ac.cn.

Abstract

Four new ent-abietane diterpenoids, along with four known ones were isolated from the aerial parts of Isodon serra, a traditional Chinese folk medicine. The new diterpenoids were named as serrin K (1), xerophilusin XVII (2), and enanderianins Q and R (3 and 4), while the known ones were identified as rubescansin J (5), (3α,14β)-3,18-[(1-methylethane-1,1-diyl)dioxy]-ent-abieta-7,15(17)-diene-14,16-diol (6), xerophilusin XIV (7), and enanderianin P (8), respectively. Their structures were elucidated by extensive spectroscopic analysis and comparison with the literature. Compound 1 showed remarkable inhibitory activity towards NO production in LPS-stimulated RAW264.7 cells (IC₅₀ = 1.8 μM) and weak cytotoxicity towards five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480).

Keywords: Isodon serra; anti-inflammation; cytotoxicity; ent-abietane diterpenoids.

MeSH terms

Abietanes / chemistry*
Abietanes / isolation & purification*
Abietanes / pharmacology
Animals
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / pharmacology
Cell Line
Cell Line, Tumor
Humans
Isodon / chemistry*
Macrophages / drug effects
Macrophages / metabolism
Magnetic Resonance Spectroscopy
Mice
Models, Molecular
Molecular Conformation
Molecular Structure
Nitric Oxide / biosynthesis
Plant Components, Aerial / chemistry
Plant Extracts / chemistry*
Plant Extracts / isolation & purification*
Plant Extracts / pharmacology

Substances

Abietanes
Antineoplastic Agents, Phytogenic
Plant Extracts
Nitric Oxide