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      Cytotoxic and Antibacterial Cembranoids from a South China Sea Soft Coral, Lobophytum sp

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          Abstract

          Chemical examination of a South China Sea soft coral Lobophytum sp. led to the isolation of three new α-methylene-γ-lactone-containing cembranoids, (1 R*,3 R*,4 R*,14 R*,7 E,11 E)-3,4-epoxycembra-7,11,15(17)-trien-16,14-olide ( 1), (1 R*,7 S*,14 S*,3 E,11 E)-7-hydroperoxycembra-3,8(19),11,15(17)-tetraen-16,14-olide ( 2), and (1 R*,7 S*,14 S*,3 E,11 E)-18-acetoxy-7-hydroperoxycembra-3,8(19),11,15(17)-tetraen-16,14-olide ( 3), along with eleven known analogues 4– 14. The structures of the new compounds were elucidated through extensive spectroscopic analysis, including 1D and 2D NMR data. Compounds 1– 3 exhibited moderate cytotoxic activity against the selected tumor cell lines. Moreover, 2 and 3 were found to be moderate inhibitors against the bacteria S. aureus and S. pneumoniae.

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          Cytotoxic and anti-inflammatory cembranoids from the soft coral Lobophytum crassum.

          Chih-kai Chao, Hsiao-Fong Yeh, Jyh-Horng Sheu … (2008)
          Five new cembranoids, namely, crassumolides A and B and D-F (1 and 2 and 4-6), along with four known metabolites, 7-10, were isolated from the soft coral Lobophytum crassum. Crassumolide C (3) was isolated for the first time from a natural source. The structures of these compounds were elucidated by extensive spectroscopic analysis and comparison of the NMR data with those of known analogues. The absolute stereochemistry of 1 was determined using the modified Mosher's method. Chemical transformation of 7 into the corresponding methyl ester 3 revealed the absolute stereochemistry of 3. Compounds 1, 3, and 7 were cytotoxic toward Ca9-22 cancer cells, and 10 was broadly cytotoxic toward all six test cancer cell lines used. Compounds 1, 3, 7, and 10 were found to inhibit the accumulation of the pro-inflammatory proteins iNOS and COX-2 at 10 μM.
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            Pestalachlorides A-C, antifungal metabolites from the plant endophytic fungus Pestalotiopsis adusta.

            Erwei Li, Lihua Jiang, Liangdong Guo … (2008)
            Pestalachlorides A-C (1-3), three new chlorinated benzophenone derivatives, have been isolated from cultures of an isolate of the plant endophytic fungus Pestalotiopsis adusta. The structures of these compounds were determined mainly by NMR spectroscopy, and the structures of 1 and 3 were further confirmed by X-ray crystallography. Pestalachloride A (1) was obtained as a mixture of two inseparable atropisomers (1a and 1b), whereas pestalachloride C (3) was found to be a racemic mixture. Compounds 1 and 2 displayed significant antifungal activities against three plant pathogens.
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              Sinugibberol, a new cytotoxic cembranoid diterpene from the soft coral Sinularia gibberosa.

              Rei-Sheu Hou, Chang-Yih Duh, Michael Chiang … (1995)
              Bioactivity-guided fractionation of a chloroform extract of the soft coral Simularia gibberosa afforded a new cytotoxic cembranoid diterpene, sinugibberol [1]. The structure of 1 was determined by spectral and X-ray crystallographic analysis.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Mar Drugs
                Journal ID (iso-abbrev): Mar Drugs
                Journal ID (publisher-id): marinedrugs
                Title: Marine Drugs
                Publisher: MDPI
                ISSN (Electronic): 1660-3397
                Publication date (Electronic): 03 April 2013
                Publication date Collection: April 2013
                Volume: 11
                Issue: 4
                Pages: 1162-1172
                Affiliations
                [1 ]School of Pharmacy, Wenzhou Medical College, Wenzhou 325035, China; E-Mails: miniezhao@ 123456gmail.com (M.Z.); yinjian198708@ 123456gmail.com (J.Y.); xzh007@ 123456126.com (Z.X.); jianyd@ 123456wzmc.edu.cn (J.D.)
                [2 ]College of Environmental Science and Engineering, Yangzhou University, Yangzhou 225127, China; E-Mail: weijiang@ 123456yzu.edu.cn
                [3 ]Analytical and Testing Center, Wenzhou University, Wenzhou 325035, China; E-Mails: youihj1023@ 123456gmail.com (M.M.); xxlei@ 123456wzu.edu.cn (X.L.)
                Author notes
                [† ]

                These authors contributed equally to this work.

                [* ] Authors to whom correspondence should be addressed; E-Mail: hkx@ 123456wzmc.edu.cn (K.H.); yanpc@ 123456wzmc.edu.cn (P.Y.); Tel.: +86-577-8668-9706 (K.H.); Fax: +86-577-8668-9706 (K.H.); Tel.: +86-577-8669-9229 (P.Y.); Fax: +86-577-8668-9983 (P.Y.).
                Article
                Publisher ID: marinedrugs-11-01162
                DOI: 10.3390/md11041162
                PMC ID: 3705396
                PubMed ID: 23552878
                SO-VID: 79f44492-8e31-4ce2-a398-ba1cc2be8a98
                Copyright © © 2013 by the authors; licensee MDPI, Basel, Switzerland.
                License:

                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
                Date received : 28 February 2013
                Date revision received : 18 March 2013
                Date accepted : 23 March 2013
                Categories
                Subject: Article

                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: soft coral,lobophytum,cembranoids,cytotoxicity,antibacterial activity
                Data availability:
                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: soft coral, lobophytum, cembranoids, cytotoxicity, antibacterial activity

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