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      Three New Sesquiterpene Aryl Esters from the Mycelium of Armillaria mellea

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          Abstract

          Three new sesquiterpene aryl esters and eight known compounds were isolated from the EtOH extract of the mycelium of Armillaria mellea. The structures of new compounds were established by analysis of their spectroscopic data. Some of the isolates showed cytotoxicity to a variety of cancer cell lines, including MCF-7, H460, HT-29, and CEM.

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          Purification, structural elucidation, and anti-inflammatory effect of a water-soluble 1,6-branched 1,3-α-d-galactan from cultured mycelia of Poria cocos

          Mei-Kuang Lu, Jing-Jy Cheng, Cha-Yui Lin … (2010)
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            Cytotoxic and antifungal activities of melleolide antibiotics follow dissimilar structure-activity relationships.

            Markus Bohnert, Hans-Wilhelm Nützmann, Volker Schroeckh … (2014)
            The fungal genus Armillaria is unique in that it is the only natural source of melleolide antibiotics, i.e., protoilludene alcohols esterified with orsellinic acid or its derivatives. This class of natural products is known to exert antimicrobial and cytotoxic effects. Here, we present a refined relationship between the structure and the antimicrobial activity of the melleolides. Using both agar diffusion and broth dilution assays, we identified the Δ(2,4)-double bond of the protoilludene moiety as a key structural feature for antifungal activity against Aspergillus nidulans, Aspergillus flavus, and Penicillium notatum. These findings contrast former reports on cytotoxic activities and may indicate a different mode of action towards susceptible fungi. We also report the isolation and structure elucidation of five melleolides (6'-dechloroarnamial, 6'-chloromelleolide F, 10-hydroxy-5'-methoxy-6'-chloroarmillane, and 13-deoxyarmellides A and B), along with the finding that treatment with an antifungal melleolide impacts transcription of A. nidulans natural product genes.
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              In vitro cytotoxicity of melleolide antibiotics: structural and mechanistic aspects.

              Markus Bohnert, Sebastian Miethbauer, Hans-Martin Dahse … (2011)
              Melleolide sesquiterpene aryl esters are secondary products of the mushroom genus Armillaria. We compared the cytotoxicity of eleven melleolides--five thereof are new natural products--against four human cancer cell lines. Armillaridin, 4-O-methylarmillaridin, and dehydroarmillylorsellinate were most active, at IC(50) = 3.0, 4.1 and 5.0 μM, respectively, against Jurkat T cells for the former two compounds, and K-562 cells for the latter. Dehydroarmillylorsellinate did not inhibit respiration and RNA-synthesis of K-562 cells at 5 μM. However, replication of DNA dropped to 35% after 120 min at this concentration, and translational activity also decreased.
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                Author and article information

                Contributors
                Thomas J. Schmidt: Role: Academic Editor
                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 29 May 2015
                Publication date Collection: June 2015
                Volume: 20
                Issue: 6
                Pages: 9994-10003
                Affiliations
                [1 ]Department of Biotechnology, HungKuang University, Sha Lu, Taichung 433, Taiwan; E-Mails: ccchen@ 123456sunrise.hk.edu.tw (C.-C.C.); alyssum15@ 123456yahoo.com.tw (C.-L.N.)
                [2 ]Department of Nursing, HungKuang University, Sha Lu, Taichung 433, Taiwan
                [3 ]Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, Taiwan; E-Mail: kuoyh@ 123456mail.cmu.edu.tw
                [4 ]Department of Biotechnology, Asia University, Taichung 413, Taiwan
                [5 ]National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Peitou, Taipei 112, Taiwan; E-Mail: verona@ 123456nricm.edu.tw
                [6 ]Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 944, Taiwan; E-Mail: pjsung@ 123456nmmba.gov.tw
                [7 ]National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan
                [8 ]Biotechnology Center, Grape King Bio Ltd., Chung Li, Taoyuan 320, Taiwan; E-Mail: gkbioeng@ 123456grapeking.com.tw
                Author notes
                [* ] Author to whom correspondence should be addressed; E-Mail: ccshen@ 123456nricm.edu.tw ; Tel.: +886-2-2820-1999 (ext. 8581); Fax: +886-2-2826-4276.
                Article
                Publisher ID: molecules-20-09994
                DOI: 10.3390/molecules20069994
                PMC ID: 6272629
                PubMed ID: 26035099
                SO-VID: 71f8585a-beec-4001-a98a-c358e018aa7b
                Copyright © © 2015 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 09 April 2015
                Date accepted : 26 May 2015
                Categories
                Subject: Article

                Keywords: sesquiterpene aryl esters,armillaria mellea,tricholomataceae,cytotoxicity
                Data availability:
                Keywords: sesquiterpene aryl esters, armillaria mellea, tricholomataceae, cytotoxicity

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