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      Bioactive Polyoxygenated Steroids from the South China Sea Soft Coral, Sarcophyton sp

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          Abstract

          Seven new polyoxygenated steroids ( 17) were isolated together with seven known analogues ( 81 4) from the South China Sea soft coral, Sarcophyton sp. The structures of the new compounds were identified on the basis of extensive spectroscopic analysis and comparison with reported data. All the steroids are characterized with 3β,5α,6β-hydroxy moiety, displaying carbon skeletons of cholestane, ergostane, gorgostane and 23,24-dimethyl cholestane. In the in vitro bioassay, metabolites exhibited different levels of antimicrobial activity against bacterial species Escherichia coli and Bacillus megaterium, and fungal species Microbotryum violaceum and Septoria tritici. No inhibition was detected towards microalga Chlorella fusca. Preliminary structure-activity analysis suggests that the 11α-acetoxy group may increase both antibacterial and antifungal activities. The terminal-double bond and the cyclopropane moiety at the side chain may also contribute to the bioactivity.

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          Most cited references39

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          Fungi from marine sponges: diversity, biological activity and secondary metabolites

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            New mono- and dimeric members of the secalonic acid family: blennolides A-G isolated from the fungus Blennoria sp.

            Blennolides A-G (2-8), seven unusual chromanones, were isolated together with secalonic acid B (1) from Blennoria sp., an endophytic fungus from Carpobrotus edulis. This is the first reported isolation of the blennolides 2 and 3 (hemisecalonic acids B and E), the existence of which as the monomeric units of the dimeric secalonic acids had long been postulated. A compound of the proposed structure 4 (beta-diversonolic ester) will need to be revised, as its reported data do not fit those of the established structure of blennolide C (4). Other monomers, the blennolides D-F (5-7) seem to be derived from blennolides A (2) and B (3) by rearrangement of the hydroaromatic ring. The heterodimer 8, composed of the monomeric blennolide A (2) and the rearranged 11-dehydroxy derivative of blennolide E (6), extends the ergochrome family with an ergoxanthin type of skeleton. The structures of the new compounds were elucidated by detailed spectroscopic analysis and further confirmed by an X-ray diffraction study of a single crystal of 2. The absolute configurations were determined by TDDFT calculations of CD spectra, including the solid-state CD/TDDFT approach. Preliminary studies showed strong antifungal and antibacterial activities of these compounds against Microbotryum violaceum and Bacillus megaterium, respectively. They were also active against the alga Chlorella fusca and the bacterium Escherichia coli.
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              Chemical Defences in Soft Corals (Coelenterata: Octocorallia) of the Great Barrier Reef: A Study of Comparative Toxicities

                Author and article information

                Journal
                Mar Drugs
                Mar Drugs
                marinedrugs
                Marine Drugs
                MDPI
                1660-3397
                11 March 2013
                March 2013
                : 11
                : 3
                : 775-787
                Affiliations
                Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, China; E-Mails: wangzenglei@ 123456gmail.com (Z.W.); tanghua0309@ 123456126.com (H.T.); w.p1008@ 123456hotmail.com (P.W.); gongweicn@ 123456foxmail.com (W.G.); bubble1206@ 123456hotmail.com (M.X.); hanbing1977.88@ 123456hotmail.com (H.Z.); liu5012004008@ 123456sina.com (T.L.); liubaoshu@ 123456126.com (B.L.)
                Author notes
                [† ]

                Present address: Department of Entomology, The Pennsylvania State University, University Park, PA 16803, USA.

                [* ] Author to whom correspondence should be addressed; E-Mails: wenzhang1968@ 123456163.com (W.Z.); yiyanghua@ 123456126.com (Y.Y.); Tel./Fax: +86-21-81871257.
                Article
                marinedrugs-11-00775
                10.3390/md11030775
                3705369
                23478486
                4957814b-873c-4175-8d2d-755b1054c1c1
                © 2013 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
                : 26 November 2012
                : 23 January 2013
                : 26 February 2013
                Categories
                Article

                Pharmacology & Pharmaceutical medicine
                antibacterial,antifungal,bioactivity,sarcophyton sp.,steroid

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