Abstract

Four new chromone derivatives, phomopsichins A–D (1–4), along with a known compound, phomoxanthone A (5), were isolated from the fermentation products of mangrove endophytic fungus Phomopsis sp. 33#. Their structures were elucidated based on comprehensive spectroscopic analysis coupled with single-crystal X-ray diffraction or theoretical calculations of electronic circular dichroism (ECD). They feature a tricyclic framework, in which a dihydropyran ring is fused with the chromone ring. Compounds 1–5 showed weak inhibitory activities on acetylcholinesterase as well as α-glucosidase, weak radical scavenging effects on 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as OH, and weak antimicrobial activities. Compounds 1–4 showed no cytotoxic activity against MDA-MB-435 breast cancer cells. Their other bioactivities are worthy of further study, considering their unique molecular structures.

Highlights

  • The chromone family of natural products exhibit a range of biological activities including anticancer, anti-inflammatory, antibacterial, antiviral, atypical antipsychotic, and anti-platelet properties [1,2,3,4,5,6,7,8,9]

  • Compounds 1–4 showed no cytotoxic activity against MDA-MB-435 breast cancer cells

  • MO, USA); 1,1-diphenyl-2-picrylhydrazyl (DPPH), H2 O2, 1,10-phenanthroline, FeSO4, and other reagents were of analytical grade and commercially available; methanol was of chromatographic grade; potato dextrose agar (PDA) medium was purchased from Beijing L and Bridge Technology Co

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Summary

Introduction

The chromone family of natural products exhibit a range of biological activities including anticancer, anti-inflammatory, antibacterial, antiviral, atypical antipsychotic, and anti-platelet properties [1,2,3,4,5,6,7,8,9]. In our continuous investigation of new bioactive secondary metabolites from the mangrove endophytic fungi in the South China Sea, four new chromone derivatives, phomopsichin. A–D (1–4), along with a known compound, phomoxanthone A (5), were isolated from the metabolic products of endophytic fungus Phomopsis sp. We report the isolation, structural elucidation, and exploration on the biological activities of compounds 1–5. We report the isolation, structural elucidation, and exploration on the biological.

Structure Elucidation
These results suggested that compound
A was dicyclic
Biological Evaluation
General Experimental Procedures
Fungal Material
Spectral Data
Computational Analyses
X-ray Crystallographic Analysis of Compound 1
AchE Inhibitory Assay
DPPH Radical Scavenging Assay
OH-Radical-Scavenging Assay
Conclusions
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