Elsevier

Bioorganic Chemistry

Volume 94, January 2020, 103362
Bioorganic Chemistry

Three new bioactive natural products from the fungus Talaromyces assiutensis JTY2

https://doi.org/10.1016/j.bioorg.2019.103362Get rights and content

Highlights

  • Three new Bioactive natural products from the Fungus Talaromyces assiutensis sp. JTY2.

  • Compound 1 is the first represent an unusual type of cyclopent derivative.

  • The anti-inflammatory activities and antibacterial activities of all isolated compounds were evaluated in vitro.

  • Compounds 14 exhibited significant inhibitory effects against the NO production.

  • Compound 2 showed broad spectrum antibacterial against six terrestrial pathogenic bacteria.

Abstract

A novel cyclopentenone derivative, talarocyclopenta A (1), a new phenolicethers derivative, talarocyclopenta B (2) and a new itaconic acid derivative, talarocyclopenta C (3) together with four known itaconic acid derivatives (47) were isolated from the Talaromyces assiutensis JTY2. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. Among them, talarocyclopent (1) is the first represent an unusual type of cyclopentenone derivative, possessing a cyclopentenone unit, a 2-butanone unit and a 3-hydroxybutyric acid unit. All isolated compounds were evaluated for their anti-inflammatory and antibacterial activities. Compounds 14 showed inhibitory activities against the nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells in vitro. Compound 2 showed broad spectrum antibacterial against six terrestrial pathogenic bacteria.

Introduction

Marine microorganisms, especially marine fungi are well known as rich sources of new natural products with promising biological and pharmacological activities [1], [2], [3]. Chemical investigations of mangrove-derived endophytic fungi, especially those from the subtropical island of Hainan, P. R. China, have shown a sharp increase in recent years [4], [5], [6]. As a result of adaptation to some special environments mangrove endophytic fungus have formed unique genetic backgrounds and metabolic pathways [7], [8], [9]. Fungi in the genus Talaromyces produce various bioactive metabolites, such as cyclic peptides, azaphilones, meroterpenoids and butenolides [10], [11], [12], [13]. In our investigation on natural antibacterial and anti-inflammatory products from mangrove fungi in the South China Sea, a fungus Talaromyces assiutensis JTY2 obtained from the leaves of Ceriops tagal attracted our attention. The EtOAc extract of a solid rice fermentation of the fungus exhibited antimicrobial activities and anti-inflammatory activities. Bioassay-guided fractionation of the bioactive extract led to the isolation of novel cyclopentenone derivative, talarocyclopenta A (1), a new phenolicethers derivative, talarocyclopenta B (2) and a new itaconic acid derivative, talarocyclopenta C (3) together with four known itaconic acid derivatives asperitaconic B (4) [14], (3S)-9-hydroxy-3-carboxy-2-methylenenonanoic acid (5) [15], (3S,8R)-8- hydroxy-3-carboxy-2-methylenenonanoic acid (6) [15] and (2S)-Butylitaconic acid (7) [16] (Fig. 1). Compounds 14 showed inhibitory activities against the nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells in vitro. Compound 2 showed broad spectrum antibacterial against six terrestrial pathogenic bacteria. Herein, we report the isolation, structure elucidation and biological activities of these compounds.

Section snippets

General experimental procedures

IR spectra were recorded on a Nicolet 6700 spectrophotometer. Optical rotations were measured on a JASCO P-1020 digital polarimeter. NMR spectra were recorded on a Bruker AV spectrometer (400 MHz for 1H and 100 MHz for 13C) and a JNM-ECZS spectrometer (600 MHz for 1H and 150 MHz for 13C). TMS was used as an internal standard. HRESIMS spectra were measured on a Q-TOF Ultima Global GAA076 LC mass spectrometer. Semi-preparative HPLC was performed on an Agilent 1260 LC series with a DAD detector

Structure elucidation

Compound 1 was isolated as colorless gum. Its molecular formula of C15H20O6 was determined by HR-ESI-MS (calcd for [M + Na]+ 319.1158, found 319.1163). The 1H NMR data revealed one olefinic proton δH 7.27 (br s), three sp3 methine signals at δH 5.34 (m), 3.55 (m) and 2.96 (d, J = 2.8 Hz), three sp3 methylene signals at δH 2.72/2.55, 2.68/2.61 and 2.43 (q, J = 7.2 Hz) and three methyl groups δH 1.05 (t, J = 7.2 Hz), δH 1.35 (d, J = 6.4 Hz) and δH 1.75 (s). The 13C NMR/135DEPT data showed 15

Conclusions

In this study, A novel cyclopentenone derivative, talarocyclopenta A (1), a new phenolicethers derivative, talarocyclopenta B (2) and a new itaconic acid derivative, talarocyclopenta C (3) together with four known itaconic acid derivatives (47) were isolated from the Talaromyces assiutensis JTY2. talarocyclopenta A (1) is the first represent an unusual type of cyclopentenone derivative, possessing a cyclopentenone unit, a 2-butanone unit and a 3-hydroxybutyric acid unit. It presence as

Declaration of Competing Interest

The authors have declared that there is no conflict of interest.

Acknowledgements

This work was supported by the Hainan Province Natural Science Foundation (218QN234), the Hainan Province Natural Science Foundation of Innovative Research Team Project (2016CXTD007), the Innovative Research Team Project of Ministry (IRT-16R19), the open foundation of Key Laboratory of Functional Molecular Engineering of Guangdong Province (No. 2018kf08) and College Students’ Innovative Training Program of Hainan Normal University (cxcyxj2018018).

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