Asperversins A and B, Two Novel Meroterpenoids with an Unusual 5/6/6/6 Ring from the Marine-Derived Fungus Aspergillus versicolor

Huaqiang Li; Weiguang Sun; Mengyi Deng; Changxing Qi; Chunmei Chen; Hucheng Zhu; Zengwei Luo; Jianping Wang; Yongbo Xue; Yonghui Zhang

doi:10.3390/md16060177

Asperversins A and B, Two Novel Meroterpenoids with an Unusual 5/6/6/6 Ring from the Marine-Derived Fungus Aspergillus versicolor

Mar Drugs. 2018 May 23;16(6):177. doi: 10.3390/md16060177.

Authors

Huaqiang Li¹, Weiguang Sun², Mengyi Deng³, Changxing Qi⁴, Chunmei Chen⁵, Hucheng Zhu⁶, Zengwei Luo⁷, Jianping Wang⁸, Yongbo Xue⁹, Yonghui Zhang¹⁰

Affiliations

¹ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. lihuaqiang2009@126.com.
² Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. weiguang_s@hust.edu.cn.
³ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. DengMengyi222@163.com.
⁴ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. kingqcx@sina.cn.
⁵ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. chenchunmei@hust.edu.cn.
⁶ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. zhuhucheng@hust.edu.cn.
⁷ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. luozengwei@hust.edu.cn.
⁸ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. jpwang1001@163.com.
⁹ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. yongboxue@hust.edu.cn.
¹⁰ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. zhangyh@mails.tjmu.edu.cn.

Abstract

Asperversins A (1) and B (2), two novel meroterpenoids featuring an uncommon 5/6/6/6 ring system, along with five new analogues (3⁻7) and a known compound asperdemin (8), were obtained from the marine-derived fungus Aspergillus versicolor. Their structures and absolute configurations were confirmed by extensive spectroscopic analyses, single-crystal X-ray diffraction studies, and electronic circular dichroism (ECD) calculation. All new compounds were tested for their acetylcholinesterase enzyme (AChE) inhibitory activities and cytotoxic activities, of which compound 7 displayed moderate inhibitory activity against the AChE with an IC₅₀ value of 13.6 μM.

Keywords: Aspergillus versicolor; acetylcholinesterase enzyme; asperversins; meroterpenoids.

MeSH terms

Aquatic Organisms / metabolism*
Aspergillus / metabolism*
Cholinesterase Inhibitors / chemistry*
Cholinesterase Inhibitors / isolation & purification
Cholinesterase Inhibitors / pharmacology
Circular Dichroism
Crystallography, X-Ray
Inhibitory Concentration 50
Molecular Structure
Spectrum Analysis
Terpenes / chemistry*
Terpenes / isolation & purification
Terpenes / pharmacology

Substances

Cholinesterase Inhibitors
Terpenes
asperversin A
asperversin B