An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10

Chengqian Pan; Yutong Shi; Bibi Nazia Auckloo; Xuegang Chen; Chen-Tung Arthur Chen; Xinyi Tao; Bin Wu

doi:10.3390/md14080156

An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10

Mar Drugs. 2016 Aug 18;14(8):156. doi: 10.3390/md14080156.

Authors

Chengqian Pan¹, Yutong Shi², Bibi Nazia Auckloo³, Xuegang Chen⁴, Chen-Tung Arthur Chen⁵, Xinyi Tao⁶, Bin Wu⁷

Affiliations

¹ Ocean College, Zhejiang University, Hangzhou 310058, China. 3100103262@zju.edu.cn.
² Ocean College, Zhejiang University, Hangzhou 310058, China. 11434028@zju.edu.cn.
³ Ocean College, Zhejiang University, Hangzhou 310058, China. naz22ia@hotmail.com.
⁴ Ocean College, Zhejiang University, Hangzhou 310058, China. chenxg83@gmail.com.
⁵ Department of Oceanography, National Sun Yat-sen University, Kaohsiung 80424, Taiwan. ctchen@mail.nsysu.edu.tw.
⁶ State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China. xytao@ecust.edu.cn.
⁷ Ocean College, Zhejiang University, Hangzhou 310058, China. wubin@zju.edu.cn.

Abstract

A new verrucosidin derivative, methyl isoverrucosidinol (1), was isolated from the marine fungus Penicillium sp. Y-50-10, dwelling in sulfur rich sediment in the Kueishantao hydrothermal vents off Taiwan. The structure was established by spectroscopic means including HRMS and 2D-NMR spectroscopic analysis. The absolute configuration was defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Among hitherto known compounds with a verrucosidine backbone isolated from natural resource, compound 1 represents the first example of a new conformational isomer of its skeleton, exhibiting antibiotic activity against Bacillus subtilis with MIC value 32 μg/mL.

Keywords: Penicillium sp.; antibiotic; conformational isomer; marine fungus; verrucosidin.

MeSH terms

Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / pharmacology
Aquatic Organisms / chemistry*
Bacillus subtilis / drug effects
Hydrothermal Vents / microbiology*
Isomerism
Microbial Sensitivity Tests
Molecular Conformation
Nuclear Magnetic Resonance, Biomolecular
Penicillium / chemistry*
Pyrones / chemistry*
Pyrones / isolation & purification
Pyrones / pharmacology
Taiwan

Substances

Anti-Bacterial Agents
Pyrones
methyl isoverrucosidinol
verrucosidin