Abstract

Four new quinazolinone alkaloids, namely, aniquinazolines A–D (1–4), were isolated and identified from the culture of Aspergillus nidulans MA-143, an endophytic fungus obtained from the leaves of marine mangrove plant Rhizophora stylosa. The structures of the new compounds were elucidated by spectroscopic analysis, and their absolute configurations were determined on the basis of chiral HPLC analysis of the acidic hydrolysates. The structure for 1 was confirmed by single-crystal X-ray diffraction analysis. All these compounds were examined for antibacterial and cytotoxic activity as well as brine shrimp (Artemia salina) lethality.

Highlights

  • Quinazolinone derivatives generally refer to the compounds possessing a building block of quinazolin-4-one

  • It is notable that some quinazolinone derivatives biogenetically synthesized by nonribosomal peptide synthesis (NRPS) [10] were isolated from a diverse group of fungi including Aspergillus fumigatus, A. flavipes, A. versicolor, Chaetomium sp., and Penicillium thymicola

  • A detailed NMR data comparison with those reported for fumiquinazoline C, a quinazolinone alkaloid identified from a fungal strain of Aspergillus fumigatus originally derived from the marine fish Pseudolabrus japonicus [2], revealed that the two compounds had the same carbon skeleton

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Summary

Introduction

Quinazolinone derivatives generally refer to the compounds possessing a building block of quinazolin-4-one. More than 160 naturally occurring quinazolinones have been isolated from different organisms including plants, animals and microorganisms [1]. This family of alkaloids has attracted great. It is notable that some quinazolinone derivatives biogenetically synthesized by nonribosomal peptide synthesis (NRPS) [10] were isolated from a diverse group of fungi including Aspergillus fumigatus, A. flavipes, A. versicolor, Chaetomium sp., and Penicillium thymicola. (Figure 1), were isolated and elucidated from the culture of the fungus Aspergillus nidulans MA-143, which was obtained from the leaves of a mangrove plant Rhizophora stylosa. Structure elucidation, and biological activity of compounds 1–4 are reported

Structure Elucidation of the New Compounds 1–4
Biological Activities of the Isolated Compounds
General
Fungal Material
Extraction and Isolation
X-ray Crystallographic Analysis of Compounds 1
Amino Acid Analysis
Reduction of Compound 1
Cytotoxicity Assay
Conclusions

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