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      Natural Product Chemistry of Gorgonian Corals of Genus Junceella—Part II

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          Abstract

          The structures, names, bioactivities, and references of 81 new secondary metabolites obtained from gorgonian corals belonging to the genus Junceella are described in this review. All compounds mentioned in this review were obtained from sea whip gorgonian corals Junceella fragilis and Junceella juncea, collected from the tropical and subtropical Indo-Pacific Ocean.

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          Key to the genera of Octocorallia exclusive of Pennatulacea (Coelenterata: Anthozoa), with diagnoses of new taxa

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            Frajunolides E-K, briarane diterpenes from Junceella fragilis.

            Chemical investigation of the gorgonian octocoral Junceella fragilis, collected in Taiwan, resulted in the isolation of seven new briarane-type diterpenes, frajunolides E-K (1-7), in addition to 14 known briaranes, praelolide, junceellin, junceellolides A-E, and K, 11a,20a-epoxy-4-deacetoxyjunceelolide D, umbraculolide A, junceellonoid A, and juncins Y, Z, and ZI, as well as ergosterol peroxide. The structures of 1-7 were determined by analysis of HRESIMS and 2D NMR spectroscopic data. Cytotoxicity and in vitro anti-inflammatory activities of compounds 1-7 were also evaluated.
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              Junceellolides J-L, 11,20-epoxybriaranes from the gorgonian coral Junceella fragilis.

              Three new 11,20-epoxybriarane diterpenoids, junceellolides J-L (1-3), along with a known metabolite, 4, have been isolated from the gorgonian coral Junceella fragilis. The structures of these metabolites were elucidated using spectroscopic methods. The cyclohexane rings were found to exist in boat form in briaranes 1 and 4 and in chair form in 2 and 3. The structure of 1 was further confirmed by chemical conversion and single-crystal X-ray diffraction analysis. The relationship between (13)C NMR chemical shifts and the conformation of the cyclohexane ring in briaranes possessing an 11,20-epoxy group are described. The briaranes 2 and 4 showed mild inhibitory effects on human neutrophil elastase release.
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                Author and article information

                Journal
                Mar Drugs
                marinedrugs
                Marine Drugs
                MDPI
                1660-3397
                19 December 2011
                December 2011
                : 9
                : 12
                : 2773-2792
                Affiliations
                [1 ]Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung 404, Taiwan; Email: yachwu@ 123456mail.cmu.edu.tw
                [2 ]Natural Medicinal Products Research Center and Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan
                [3 ]Institute of Marine Biotechnology, National Dong Hwa University, Pingtung 944, Taiwan; Email: x2219@ 123456nmmba.gov.tw (J.-H.S.); cfweng@ 123456mail.ndhu.edu.tw (C.-F.W.); chlee016@ 123456mail.ndhu.edu.tw (C.-H.L.); jinx6609@ 123456nmmba.gov.tw (M.-C.L.); jimmy@ 123456nmmba.gov.tw (J.K.)
                [4 ]National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan; Email: whw@ 123456nmmba.gov.tw (W.-H.W.); jj@ 123456nmmba.gov.tw (J.-J.L.)
                [5 ]Uni-President Biotech Co., LTD., No. 31, Gongye 2nd Rd., Annan District, Tainan 709, Taiwan; Email: tong.xin@ 123456msa.hinet.net (T.-T.C.); pin@ 123456unibiotech.com.tw (Y.-P.C.)
                [6 ]Department of Life Science and Institute of Biotechnology, National Dong Hwa University, Hualien 974, Taiwan
                [7 ]Department of Sport, Health and Leisure, Cheng Shiu University, Kaohsiung 833, Taiwan; Email: lsfang@ 123456csu.edu.tw
                [8 ]Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan
                [9 ]Division of Marine Biotechnology, Asia-Pacific Ocean Research Center, National Sun Yat-sen University, Kaohsiung 804, Taiwan
                Author notes
                [* ] Authors to whom correspondence should be addressed; Email: sheu@ 123456mail.nsysu.edu.tw (J.-H.S.); pjsung@ 123456nmmba.gov.tw (P.-J.S.); Tel.: +886-7-525-2000 (ext. 5030) (J.-H.S.); +886-8-882-5037 (P.-J.S.); Fax: +886-7-525-5020 (J.-H.S.); +886-8-882-5087 (P.-J.S.).
                Article
                marinedrugs-09-02773
                10.3390/md9122773
                3280581
                22363249
                e47f5dcd-d52f-42ea-9c1c-0148dd1be3be
                © 2011 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
                : 10 November 2011
                : 06 December 2011
                : 15 December 2011
                Categories
                Review

                Pharmacology & Pharmaceutical medicine
                south china sea,briarane,junceella,indo-pacific ocean,gorgonian

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