Two new unsaturated fatty acids from the mangrove rhizosphere soil-derived fungus Penicillium javanicum HK1-22

Zhao-Yang Liang; Nan-Xing Shen; Yao-Yao Zheng; Jin-Tao Wu; Li Miao; Xiu-Mei Fu; Min Chen; Chang-Yun Wang

doi:10.1016/j.bioorg.2019.103331

Two new unsaturated fatty acids from the mangrove rhizosphere soil-derived fungus Penicillium javanicum HK1-22

Bioorg Chem. 2019 Dec:93:103331. doi: 10.1016/j.bioorg.2019.103331. Epub 2019 Sep 30.

Authors

Zhao-Yang Liang¹, Nan-Xing Shen², Yao-Yao Zheng¹, Jin-Tao Wu², Li Miao², Xiu-Mei Fu³, Min Chen⁴, Chang-Yun Wang⁵

Affiliations

¹ Marine Science & Technology Institute, College of Environmental Science & Engineering, Yangzhou University, 196#, Huayang West Street, Yangzhou City, Jiangsu Province, People's Republic of China; Key Laboratory of Marine Drugs, the Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China; Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, People's Republic of China.
² Marine Science & Technology Institute, College of Environmental Science & Engineering, Yangzhou University, 196#, Huayang West Street, Yangzhou City, Jiangsu Province, People's Republic of China.
³ Key Laboratory of Marine Drugs, the Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China.
⁴ Marine Science & Technology Institute, College of Environmental Science & Engineering, Yangzhou University, 196#, Huayang West Street, Yangzhou City, Jiangsu Province, People's Republic of China. Electronic address: dieying0719@163.com.
⁵ Key Laboratory of Marine Drugs, the Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China; Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, People's Republic of China; Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, People's Republic of China. Electronic address: changyun@ouc.edu.cn.

PMID: 31622851
DOI: 10.1016/j.bioorg.2019.103331

Abstract

Two new unsaturated fatty acids, 6R,8R-dihydroxy-9Z,12Z-octadecadienoic acid (1) and methyl-6R,8R-dihydroxy-9Z,12Z-octadecadienoate (2), and two known 9Z,12Z-octadecadienoic acid analogues (3, 4) together with a known sesquiterpenoid (5) were isolated from the mangrove rhizosphere soil-derived fungus Penicillium javanicum HK1-22. An acetonide derivative (1a) from 1 was also prepared. The relative configuration of 1 was determined by analysis of the 1D and 2D NOE spectra of 1a. The absolute configuration of 1 was assigned on the basis of biogenetic considerations. The antifungal activity of the high yield compound 5 was evaluated against four strains of crop pathogens and it showed significant antifungal activities against all the tested strains.

Keywords: Antifungal activity; Mangrove rhizosphere soil-derived fungus; Penicillium javanicum; Unsaturated fatty acid.

Publication types

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

MeSH terms

Antifungal Agents / chemistry
Antifungal Agents / isolation & purification
Antifungal Agents / pharmacology
Carbon-13 Magnetic Resonance Spectroscopy
Crops, Agricultural / microbiology
Fatty Acids, Unsaturated / chemistry
Fatty Acids, Unsaturated / isolation & purification*
Fatty Acids, Unsaturated / pharmacology
Penicillium / chemistry*
Penicillium / classification
Penicillium / genetics
Phylogeny
Proton Magnetic Resonance Spectroscopy
Rhizosphere*
Soil Microbiology*
Spectrometry, Mass, Electrospray Ionization
Wetlands*

Substances

Antifungal Agents
Fatty Acids, Unsaturated