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      Prenylated Indolediketopiperazine Peroxides and Related Homologues from the Marine Sediment-Derived Fungus Penicillium brefeldianum SD-273

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          Abstract

          Three new indolediketopiperazine peroxides, namely, 24-hydroxyverruculogen ( 1), 26-hydroxyverruculogen ( 2), and 13- O-prenyl-26-hydroxyverruculogen ( 3), along with four known homologues ( 47), were isolated and identified from the culture extract of the marine sediment-derived fungus Penicillium brefeldianum SD-273. Their structures were determined based on the extensive spectroscopic analysis and compound 1 was confirmed by X-ray crystallographic analysis. The absolute configuration of compounds 13 was determined using chiral HPLC analysis of their acidic hydrolysates. Each of the isolated compounds was evaluated for antibacterial and cytotoxic activity as well as brine shrimp ( Artemia salina) lethality.

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          Brine shrimp: a convenient general bioassay for active plant constituents.

          A method, utilizing brine shrimp (Artemia salina Leach), is proposed as a simple bioassay for natural product research. The procedure determines LC (50) values in microg/ml of active compounds and extracts in the brine medium. Activities of a broad range of known active compounds are manifested as toxicity to the shrimp. Screening results with seed extracts of 41 species of Euphorbiaceae were compared with 9KB and 9PS cytotoxicities. The method is rapid, reliable, inexpensive, and convenient as an in-house general bioassay tool.
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            Phylogeny of Penicillium and the segregation of Trichocomaceae into three families

            Species of Trichocomaceae occur commonly and are important to both industry and medicine. They are associated with food spoilage and mycotoxin production and can occur in the indoor environment, causing health hazards by the formation of β-glucans, mycotoxins and surface proteins. Some species are opportunistic pathogens, while others are exploited in biotechnology for the production of enzymes, antibiotics and other products. Penicillium belongs phylogenetically to Trichocomaceae and more than 250 species are currently accepted in this genus. In this study, we investigated the relationship of Penicillium to other genera of Trichocomaceae and studied in detail the phylogeny of the genus itself. In order to study these relationships, partial RPB1, RPB2 (RNA polymerase II genes), Tsr1 (putative ribosome biogenesis protein) and Cct8 (putative chaperonin complex component TCP-1) gene sequences were obtained. The Trichocomaceae are divided in three separate families: Aspergillaceae, Thermoascaceae and Trichocomaceae. The Aspergillaceae are characterised by the formation flask-shaped or cylindrical phialides, asci produced inside cleistothecia or surrounded by Hülle cells and mainly ascospores with a furrow or slit, while the Trichocomaceae are defined by the formation of lanceolate phialides, asci borne within a tuft or layer of loose hyphae and ascospores lacking a slit. Thermoascus and Paecilomyces, both members of Thermoascaceae, also form ascospores lacking a furrow or slit, but are differentiated from Trichocomaceae by the production of asci from croziers and their thermotolerant or thermophilic nature. Phylogenetic analysis shows that Penicillium is polyphyletic. The genus is re-defined and a monophyletic genus for both anamorphs and teleomorphs is created (Penicillium sensu stricto). The genera Thysanophora, Eupenicillium, Chromocleista, Hemicarpenteles and Torulomyces belong in Penicillium s. str. and new combinations for the species belonging to these genera are proposed. Analysis of Penicillium below genus rank revealed the presence of 25 clades. A new classification system including both anamorph and teleomorph species is proposed and these 25 clades are treated here as sections. An overview of species belonging to each section is presented. Taxonomic novelties: New sections, all in Penicillium: sect. Sclerotiora Houbraken & Samson, sect. Charlesia Houbraken & Samson, sect. Thysanophora Houbraken & Samson,sect. Ochrosalmonea Houbraken & Samson, sect. Cinnamopurpurea Houbraken & Samson, Fracta Houbraken & Samson, sect. Stolkia Houbraken & Samson, sect. Gracilenta Houbraken & Samson, sect. Citrina Houbraken & Samson, sect. Turbata Houbraken & Samson, sect. Paradoxa Houbraken & Samson, sect. Canescentia Houbraken & Samson. New combinations: Penicillium asymmetricum (Subramanian & Sudha) Houbraken & Samson, P. bovifimosum (Tuthill & Frisvad) Houbraken & Samson, P. glaucoalbidum (Desmazières) Houbraken & Samson, P. laeve (K. Ando & Manoch) Houbraken & Samson, P. longisporum (Kendrick) Houbraken & Samson, P. malachiteum (Yaguchi & Udagawa) Houbraken & Samson, P. ovatum (K. Ando & Nawawi) Houbraken & Samson, P. parviverrucosum (K. Ando & Pitt) Houbraken & Samson, P. saturniforme (Wang & Zhuang) Houbraken & Samson, P. taiwanense (Matsushima) Houbraken & Samson. New names: Penicillium coniferophilum Houbraken & Samson, P. hennebertii Houbraken & Samson, P. melanostipe Houbraken & Samson, P. porphyreum Houbraken & Samson.
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              Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman.

              The chemical composition of the essential oil of Haplophyllum tuberculatum (Forsskal) A. Juss (Rutaceae) was analyzed by gas chromatography-mass spectral (GC-MS) and 13C NMR spectroscopy. Thirty compounds, constituting about 99.7% of the total oil, were identified. The most abundant oil components are beta-phellandrene (23.3%), limonene (12.6%), (Z)-beta-ocimene (12.3%), beta-caryophyllene (11.6%), myrcene (11.3%), and alpha-phellandrene (10.9%). Ten microlitres (25 mg) of pure oil partially inhibited the growth of Escherichia coli, Salmonella choleraesuis, and Bacillus subtilis to the same extent as 0.10 microg of gentamycin sulfate. The oil also affected the mycelial growth of Curvularia lunata and Fusarium oxysporium in a dose-dependent manner but had no effect on the germination of their spores.
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                Author and article information

                Journal
                Mar Drugs
                Mar Drugs
                marinedrugs
                Marine Drugs
                MDPI
                1660-3397
                27 January 2014
                February 2014
                : 12
                : 2
                : 746-756
                Affiliations
                [1 ]Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China; E-Mails: anchy5885@ 123456gmail.com (C.-Y.A.); lixmqd@ 123456yahoo.com.cn (X.-M.L.); lichunshun@ 123456ms.qdio.ac.cn (C.-S.L.); aericxu@ 123456gmail.com (G.-M.X.)
                [2 ]University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, China
                Author notes
                [* ]Author to whom correspondence should be addressed; E-Mail: wangbg@ 123456ms.qdio.ac.cn ; Tel./Fax: +86-532-8289-8553.
                Article
                marinedrugs-12-00746
                10.3390/md12020746
                3944513
                24473173
                e51b739e-315a-4133-bb6a-a2f447cd4d4e
                © 2014 by the authors; 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/3.0/).

                History
                : 21 November 2013
                : 10 January 2014
                : 15 January 2014
                Categories
                Article

                Pharmacology & Pharmaceutical medicine
                marine sediment,penicillium brefeldianum sd-273,indolediketopiperazine,brine shrimp lethality

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