Polyketides with antimicrobial activities from Penicillium canescens DJJ-1

Jia-Peng Wang; Yan Shu; Sheng-Qi Zhang; Lin-Lin Yao; Bing-Xian Li; Li Zhu; Xiao Zhang; Huai Xiao; Le Cai; Zhong-Tao Ding

doi:10.1016/j.phytochem.2022.113554

Polyketides with antimicrobial activities from Penicillium canescens DJJ-1

Phytochemistry. 2023 Feb:206:113554. doi: 10.1016/j.phytochem.2022.113554. Epub 2022 Dec 7.

Authors

Jia-Peng Wang¹, Yan Shu², Sheng-Qi Zhang², Lin-Lin Yao², Bing-Xian Li², Li Zhu², Xiao Zhang², Huai Xiao³, Le Cai⁴, Zhong-Tao Ding⁵

Affiliations

¹ Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China; Yunnan Provincial Key Laboratory of Entomological Biopharmaceutical R&D, College of Pharmacy, Dali University, Dali, Yunnan, China.
² Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China.
³ Yunnan Provincial Key Laboratory of Entomological Biopharmaceutical R&D, College of Pharmacy, Dali University, Dali, Yunnan, China.
⁴ Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China. Electronic address: caile@ynu.edu.cn.
⁵ Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China; Yunnan Provincial Key Laboratory of Entomological Biopharmaceutical R&D, College of Pharmacy, Dali University, Dali, Yunnan, China. Electronic address: ztding@ynu.edu.cn.

PMID: 36496005
DOI: 10.1016/j.phytochem.2022.113554

Abstract

Two undescribed polyketides canecines A-B, one unreported cyclopentenone canecine C, together with 12 known compounds were isolated from an extract of the fungus Penicillium canescens DJJ-1. Their structures were elucidated by detailed analysis of spectroscopic data, NMR calculations with dJ-DP4 or DP4+, and their absolute configurations were further determined by quantum chemical calculations of ECD spectra or X-crystallography. Canecine A was a grisan polyketide featuring a dimethyltetrahydro-4H-furo[2,3-b]pyran. Canecine A exhibited significant inhibitory activity against Candida albicans with an MIC value of 1 μg/mL and showed inhibitory effect on nitric oxide production in LPS-activated RAW264.7 macrophages. These results enrich the structural diversities of polyketides from endophytic fungi.

Keywords: Antimicrobial activity; Canecine; J-DP4; Penicillium canescens; Trichocomaceae.

MeSH terms

Anti-Infective Agents*
Magnetic Resonance Spectroscopy
Molecular Structure
Penicillium* / chemistry
Polyketides* / chemistry

Substances

Polyketides
Anti-Infective Agents

Supplementary concepts

Penicillium canescens