Gypmacrophin A, a Rare Pentacyclic Sesterterpenoid, Together with Three Depsides, Functioned as New Chemical Evidence for Gypsoplaca macrophylla (Zahlbr.) Timdal Identification

Yuan-Fei Zhou; Hai-Xia Shi; Kun Hu; Jian-Wei Tang; Xing-Ren Li; Xue Du; Han-Dong Sun; Li-Song Wang; Jian-Xin Pu

doi:10.3390/molecules22101675

Gypmacrophin A, a Rare Pentacyclic Sesterterpenoid, Together with Three Depsides, Functioned as New Chemical Evidence for Gypsoplaca macrophylla (Zahlbr.) Timdal Identification

Molecules. 2017 Oct 9;22(10):1675. doi: 10.3390/molecules22101675.

Authors

Yuan-Fei Zhou^{1

2}, Hai-Xia Shi³, Kun Hu^{4

5}, Jian-Wei Tang^{6

7}, Xing-Ren Li^{8

9}, Xue Du¹⁰, Han-Dong Sun¹¹, Li-Song Wang¹², Jian-Xin Pu¹³

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. zhouyuanfei@mail.kib.ac.cn.
² Kunming College of Life Sciences, University of Chinese Academy of Sciences, Beijing 100039, China. zhouyuanfei@mail.kib.ac.cn.
³ Key Laboratory for Plant Biodiversity and Biogeography of East Asia, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. hukun@mail.kib.ac.cn.
⁴ 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.
⁵ Kunming College of Life Sciences, University of Chinese Academy of Sciences, Beijing 100039, China. tangjianwei@mail.kib.ac.cn.
⁶ 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.
⁷ Kunming College of Life Sciences, University of Chinese Academy of Sciences, Beijing 100039, China. lixingren@mail.kib.ac.cn.
⁸ 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.
⁹ Kunming College of Life Sciences, University of Chinese Academy of Sciences, Beijing 100039, 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. hdsun@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. shihaixia@mail.kib.ac.cn.
¹² Key Laboratory for Plant Biodiversity and Biogeography of East Asia, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. wanglisong@mail.kib.ac.cn.
¹³ 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

The phytochemical investigation on 1 g of materials from Gypsoplacamacrophylla (Zahlbr.) Timdal resulted in the discovery of gypmacrophin A, a rare pentacyclic sesterterpenoid; brialmontin III, a new polysubstituted depside and two known ones, brialmontins I and II. The structure and absolute configurations of gypmacrophin A were elucidated by spectroscopic analyses and computational methods. Gypmacrophin A showed weak inhibition of AchE with an IC₅₀ value of 32.03 μM. The four compounds provided new chemical evidence for G. macrophylla identification.

Keywords: Gypsoplaca macrophylla; Gypsoplacaceae; Identification; Sesterterpenoid.

MeSH terms

Acetylcholinesterase
Ascomycota / isolation & purification*
Depsides / chemistry*
Models, Molecular
Molecular Structure
Peptide Fragments / antagonists & inhibitors
Sesterterpenes / chemistry*
Structure-Activity Relationship

Substances

AchE peptide
Depsides
Peptide Fragments
Sesterterpenes
Acetylcholinesterase