Chemical constituents from wetland soil fungus Penicillium oxalicum GY1

Ting Ding; Yuan Zhou; Jiang-Jiang Qin; Luo-Jie Yang; Wei-Dong Zhang; Yun-Heng Shen

doi:10.1016/j.fitote.2020.104530

Chemical constituents from wetland soil fungus Penicillium oxalicum GY1

Fitoterapia. 2020 Apr:142:104530. doi: 10.1016/j.fitote.2020.104530. Epub 2020 Feb 28.

Authors

Ting Ding¹, Yuan Zhou², Jiang-Jiang Qin³, Luo-Jie Yang⁴, Wei-Dong Zhang⁵, Yun-Heng Shen⁶

Affiliations

¹ State Key Laboratory of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai 201203, China.
² College of Pharmaceutical Sciences, Zhejiang Chinese Medical University, Hangzhou 310053, China.
³ College of Pharmaceutical Sciences, Zhejiang Chinese Medical University, Hangzhou 310053, China; Institute of Cancer and Basic Medicine, Chinese Academy of Sciences, Cancer Hospital of the University of Chinese Academy of Sciences, Zhejiang Cancer Hospital, Hangzhou, China.
⁴ Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China.
⁵ State Key Laboratory of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai 201203, China; School of Pharmacy, The Second Military Medical University, Shanghai 200433, China. Electronic address: [email protected].
⁶ School of Pharmacy, The Second Military Medical University, Shanghai 200433, China. Electronic address: [email protected].

PMID: 32114035
DOI: 10.1016/j.fitote.2020.104530

Abstract

A new azo compound, penoxalin (1), a new isochroman carboxylic acid, penisochroman B (3), two new natural products, penisochroman A (2) and 2,6-dihydroxy-4-[(2R)-2-hydroxyheptyl] benzoic acid (4), together with four known compounds (5-8) were isolated from wetland soil fungus Penicillium oxalicum GY1. All structures were elucidated by extensive NMR spectroscopic evidences together with mass spectrometry. The absolute configuration of penoxalin (1) was determined by calculated ECD spectrum, while the absolute configuration of new natural product penisochroman A (2) was established for the first time by single crystal X-ray diffraction. In addition, all compounds were evaluated for their cytotoxic activity in vitro. 2, 6-Dihydroxy-4-[(2R)-2-hydroxyheptyl] benzoic acid (4) displayed significant cytotoxicity against human esophageal carcinoma cells OE19 with an IC₅₀ value of 5.50 μM.

Keywords: Absolute configuration; Azo; Cytotoxic activity; Isochroman carboxylic acid; Penicillium oxalicum; Soil fungus.

MeSH terms

Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification*
Azo Compounds / chemistry
Azo Compounds / isolation & purification*
Benzoates / chemistry
Benzoates / isolation & purification*
Cell Line, Tumor
Drug Screening Assays, Antitumor
Humans
Penicillium / chemistry*
Wetlands

Substances

Antineoplastic Agents
Azo Compounds
Benzoates

Supplementary concepts

Penicillium oxalicum