Abstract
Four new uncommon 20-nor-isopimarane diterpenoid epimers, aspewentins I−L (1–4), together with a new methylated derivative of 3, aspewentin M (5), were isolated from the deep sea sediment-derived fungus Aspergillus wentii SD-310. The very similar structures of these epimers made the separation and purification procedures difficult. The structures of compounds 1–5 were illustrated based on spectroscopic analysis, and the absolute configurations of compounds 1–5 were unambiguously determined by the combination of NOESY, time-dependent density functional (TDDFT)-ECD calculations, and X-ray crystallographic analysis. These metabolites represented the rare examples of 20-nor-isopimarane analogues possessing a cyclohexa-2,5-dien-1-one moiety. These compounds were tested for antimicrobial activities against human and aquatic pathogenic bacteria, as well as plant-pathogenic fungi. While compounds 1 and 2 exhibited inhibitory activities against zoonotic pathogenic bacteria such as Escherichia coli, Edwardsiella tarda, Vibrio harveyi, and V. parahaemolyticus, compound 5 showed potent activity against the plant pathogen Fusarium graminearum.
Highlights
Aspergillus wentii is a biosynthetically talented fungal species with great potential to produce a wide range of structurally diversified secondary metabolites such as glucans [1], polyketides [2,3], and terpenoids [4,5,6]
In the process of our excavation to identify new bioactive compounds from marine-derived fungi [7,8,9,10,11], the fungus A. wentii SD-310, which was isolated from a deep sea sediment sample and which produces a series of 20-nor-isopimarane diterpenoids [12,13,14], was selected for further study
The pathogenic bacteria and aquatic pathogen strains were provided by the Institute of Oceanology, Chinese Academy of Sciences, while the plant pathogenic fungi strains were provided by Qingdao Agricultural University
Summary
Aspergillus wentii is a biosynthetically talented fungal species with great potential to produce a wide range of structurally diversified secondary metabolites such as glucans [1], polyketides [2,3], and terpenoids [4,5,6] Some of these metabolites exhibit intriguing biological properties including antimicrobial properties [2,6], antioxidant properties [3], cytotoxicity against human cancer cell lines [5], and plant growth-inhibiting activities [4]. Structures of the isolated compounds werethe compounds were established through detailed interpretation of the and mass spectrometric absolute configurations were determined by the combination of NOESY, quantum chemical. ECD established through detailed interpretation of the NMR and mass spectrometric data, and the data, and the absolute configurations were determined by the combination of NOESY, quantum calculations, and. Allexamples of these compounds were examined for antimicrobial activities against human and aquatic of 20-nor-isopimarane analogues possessing a cyclohexa-2,5-dien-1-one moiety at ring B.
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