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Molecules 2017, 22(7), 1202; doi:10.3390/molecules22071202

Akanthopyrones A–D, α-Pyrones Bearing a 4-O-Methyl-β-d-glucopyranose Moiety from the Spider-Associated Ascomycete Akanthomyces novoguineensis

1
Department of Microbial Drugs, Helmholtz Centre for Infection Research, 38124 Braunschweig, Germany
2
Department of Microbiology, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand
3
Department of Chemistry, Faculty of Science, Aswan University, Aswan 81528, Egypt
4
Department of Chemistry, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand
5
Natural Products Research Center of Excellence, Prince of Songkla University, Songkhla 90112, Thailand
6
National Centre for Genetic Engineering and Biotechnology (BIOTEC), Pathumthani 12120, Thailand
7
Center of Excellence for Innovation in Chemistry, Prince of Songkla University, Songkhla 90112, Thailand
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 20 June 2017 / Accepted: 13 July 2017 / Published: 18 July 2017
(This article belongs to the Section Natural Products)
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Abstract

Hypocrealean fungi have proved to be prolific bioactive metabolite producers; they have caught the attention of mycologists throughout the world. However, only a few studies on the insect and spider parasitic genus Akanthomyces have so far been carried out. In this study, we report the isolation, structural elucidation and biological activities of four unprecedented glycosylated α-pyrone derivatives, akanthopyrones A–D (14), from a culture of Akanthomyces novoguineensis collected in Thailand. The chemical structures of the akanthopyrones were determined by extensive 1D- and 2D-NMR, and HRMS spectroscopic analysis. Their absolute configurations were determined. Akanthopyrone A (1) exhibited weak antimicrobial activity against Bacillus subtilis DSM10 and cytotoxicity against the HeLa cell line KB-3-1, while akanthopyrone D (4) showed weak activity against Candida tenuis MUCL 29892. View Full-Text
Keywords: cordycipitaceae; hypocreales; invertebrate-associated fungi; α-pyrones; 4-O-methyl-β-d-glucopyranose cordycipitaceae; hypocreales; invertebrate-associated fungi; α-pyrones; 4-O-methyl-β-d-glucopyranose
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Kuephadungphan, W.; Helaly, S.E.; Daengrot, C.; Phongpaichit, S.; Luangsa-ard, J.J.; Rukachaisirikul, V.; Stadler, M. Akanthopyrones A–D, α-Pyrones Bearing a 4-O-Methyl-β-d-glucopyranose Moiety from the Spider-Associated Ascomycete Akanthomyces novoguineensis. Molecules 2017, 22, 1202.

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