Penipyrols C-G and methyl-penipyrol A, α-pyrone polyketides from the mangrove derived fungus Penicillium sp. HDN-11-131

Lu Wang; Yeqin Shi; Qian Che; Tianjiao Zhu; Guojian Zhang; Xiaokun Zhang; Mingyu Li; Dehai Li

doi:10.1016/j.bioorg.2021.104975

Penipyrols C-G and methyl-penipyrol A, α-pyrone polyketides from the mangrove derived fungus Penicillium sp. HDN-11-131

Bioorg Chem. 2021 Aug:113:104975. doi: 10.1016/j.bioorg.2021.104975. Epub 2021 May 18.

Authors

Lu Wang¹, Yeqin Shi², Qian Che¹, Tianjiao Zhu¹, Guojian Zhang³, Xiaokun Zhang², Mingyu Li⁴, Dehai Li⁵

Affiliations

¹ Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China.
² Fujian Provincial Key Laboratory of Innovative Drug Target Research, School of Pharmaceutical Science, Xiamen University, Fujian 361102, PR China.
³ Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China; Laboratory for Marine Drugs and Bioproducts of Qingdao Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, PR China.
⁴ Fujian Provincial Key Laboratory of Innovative Drug Target Research, School of Pharmaceutical Science, Xiamen University, Fujian 361102, PR China. Electronic address: limingyu@xmu.edu.cn.
⁵ Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China; Laboratory for Marine Drugs and Bioproducts of Qingdao Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, PR China. Electronic address: dehaili@ouc.edu.cn.

PMID: 34020278
DOI: 10.1016/j.bioorg.2021.104975

Abstract

Six new α-pyrone polyketides, penipyrols C-G (1-5) and methyl-penipyrol A (6), together with one biogenetically related known compound, penipyrol A (7), were isolated from the extract of fungus Penicillium sp. HDN-11-131. Their structures including the absolute configurations were established by extensive spectroscopic analysis, Mosher's method, and ECD calculations as well as biogenic considerations. Compounds 1-4 possess a rare skeleton featuring γ-butyrolactone linked to α-pyrone ring through double bond. Compound 1 can induce pancreatic β-cell regeneration in zebrafish at 10 μM, which demonstrated promising anti-diabetes potential.

Keywords: Diabetes; Polyketides; Zebrafish; α-Pyrone; β-cell regeneration; γ-Butyrolactone.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Dose-Response Relationship, Drug
Hypoglycemic Agents / chemistry
Hypoglycemic Agents / isolation & purification
Hypoglycemic Agents / pharmacology*
Insulin-Secreting Cells / drug effects*
Molecular Structure
Penicillium / chemistry*
Polyketides / chemistry
Polyketides / isolation & purification
Polyketides / pharmacology*
Pyrones / chemistry
Pyrones / isolation & purification
Pyrones / pharmacology*
Regeneration / drug effects
Structure-Activity Relationship
Zebrafish

Substances

Hypoglycemic Agents
Polyketides
Pyrones