Abstract

Five new chromone-derived polyketides phaseolorins A-F (1–5), together with nine known compounds, were isolated from the deep-sea derived fungus Diaporthe phaseolorum FS431. The structures of new compounds were determined by analysis of their NMR and high-resolution electrospray ionization mass spectroscopy (HRESIMS) spectroscopic data. The absolute configurations were confirmed by chemical transformations, extensively experimental electron capture detection (ECD) calculations, or X-ray crystallography. Among them, compound 2 represented the first example for a new family of chromone derivative possessing an unprecedented recombined five-member γ-lactone ring. Moreover, the new compounds (1–5) were evaluated for in vitro cytotoxic activities against a panel of human cancer cell lines.

Highlights

  • Marine-derived fungi are emerging as a promising source for discovering novel natural products with significant biological and pharmacological properties

  • Previous studies towards the fungi of the genus Diaporthe have revealed that these fungi are capable of producing structurally fascinating and architecturally diverse natural products, such as polyketides, highly substituted benzophenone, pyran-2-one, terpenoid, and diapolic acid [3,4,5,6,7], which usually showed potent cGMP-dependent protein kinase inhibitory and antiparasitic [4], antibacterial [8,9], antimalarial [10], and cytotoxic activities [11,12]

  • The IR spectrum displayed the classical absorption bands at 3362, 1771, and 1614 cm−1, which were characteristic for the hydroxy, γ-lactone carbonyl, and conjugated ketone

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Summary

Introduction

Marine-derived fungi are emerging as a promising source for discovering novel natural products with significant biological and pharmacological properties. Deep-sea fungi have attracted even more attention in recent years because they are naturally forced to metabolize more potent bioactive compounds to acclimatize the extreme and variable environments of the deep sea, which has resulted in the generation of numerous chemically diverse and structurally unique secondary metabolites. Deep-sea fungi have been proverbially respected to be one of the most potential resources for the discovery of biologically meaningful natural products [1,2]. G (6) [13], 4-hydroxyphenthyl methyl known derivatives identified as phomoxanthone.

Structure Elucidation
Perspective
H and resembled to those of and
Biological Activity
General Experimental Procedures
Fungal Material
Fermentation and Extraction
Isolation and Purification
The Chemical Transformation Between Compounds 1 and 2
Details of ECD Calculations
Conclusions

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