Scalarane-type Sesterterpenes from the Philippines Sponge Hyrtios sp.
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The marine sponge Hyrtios sp. collected in the Philippines was extracted and partitioned. The resulting organic layer was purified by C18 reversed-phase column chromatography and HPLC to achieve the separation of nine scalarane-type sesterterpenes, including one new compound with eight known scalarane analogs. The chemical structures of the isolated compounds 1−9 were elucidated by 1D and 2D NMR and MS data analysis. All nine compounds were evaluated for their antibacterial activities against three Gram-positive and three Gram-negative bacteria. The compound 3 exhibited potent antibacterial activities against Bacillus subtilis and Micrococcus luteus. The compounds 7 and 9 displayed considerable activities against Bacillus subtilis and the others had moderate results.
Abstract
The marine sponge Hyrtios sp. collected in the Philippines was extracted and partitioned. The resulting organic layer was purified by C18 reversed-phase column chromatography and HPLC to achieve the separation of nine scalarane-type sesterterpenes, including one new compound with eight known scalarane analogs. The chemical structures of the isolated compounds 1−9 were elucidated by 1D and 2D NMR and MS data analysis. All nine compounds were evaluated for their antibacterial activities against three Gram-positive and three Gram-negative bacteria. The compound 3 exhibited potent antibacterial activities against Bacillus subtilis and Micrococcus luteus. The compounds 7 and 9 displayed considerable activities against Bacillus subtilis and the others had moderate results.
참고문헌 (25)
- Amina M, "Biological resource of waters", pp.201~230 (2018), IntechOpen
- Cimino G, "13C-NMR spectrum and absolute stereochemistry of furoscalarol", Tetrahedron Lett, 19(23), pp.2041~2044 (1978)
- Davis R, "Two new scalarane sesterterpenes : Isoscalarafuran-A and-B, epimeric alcohols from a southern Australian Marine Sponge, Spongia hispida", Aust J Chem, 46(8), pp.1295~1299 (1993)
- De Rosa S, "A new scalarane sesterterpenoid from the marine sponge Cacospongia mollior", J Nat Prod, 57(2), pp.256~262 (1994)
- Doi Y, "New sesterterpenes with nerve growth factor synthesis-stimulating activity from the Okinawan marine sponge Hyrtios sp", Chem Pharm Bull, 41(12), pp.2190~2191 (1993)
- Fattorusso E, "Scalarin, a new pentacyclic C-25 terpenoid from the sponge Cacospongia scalaris", Tetrahedron, 28(24), pp.5993~5997 (1972)
- Fontana A, "New scalaranes from the nudibranch Glossodoris atromarginata and its sponge prey", J Nat Prod, 62(10), pp.1367~1370 (1999)
- Fontana A, "Scalarane and homoscalarane compounds from the nudibranchs Glossodoris sedna and Glossodoris dalli : Chemical and biological properties", J Nat Prod, 63(4), pp.527~530 (2000)
- Gavagnin M, "Scalarane metabolites of the nudibranch Glossodoris rufomarginata and its dietary sponge from the South China Sea", J Nat Prod, 67(12), pp.2104~2107 (2004)
- Gonzalez MA, "Scalarane sesterterpenoids", Curr Bioact Compd, 6(3), pp.178~206 (2010)
- Iguchi K, "Hyrtiosal, a new sesterterpenoid with a novel carbon skeleton from the Okinawan marine sponge Hyrtios erectus", J Org Chem, 57(2), pp.522~524 (1992)
- Jaspars M, "Using scalarane sesterterpenes to examine a sponge taxonomic anomaly", J Nat Prod, 60(6), pp.556~561 (1997)
- Kamel HN, "Scalarane sesterterpenoids : Semisynthesis and biological activity", J Nat Prod, 72(8), pp.1492~1496 (2009)
- Kashman Y, "The 13C-NMR spectrum and stereochemistry of heteronemin", Tetrahedron, 33(22), pp.2997~2998 (1997)
- Lee Y-J, "Cytotoxic sesterterpenoids isolated from the marine sponge Scalarispongia sp", Int J Mol Sci, 15(11), pp.20045~20053 (2014)
- Liu Y, "Sesterterpenoids", Nat Prod Rep, 24(6), pp.1401~1429 (2007)
- Miller JH, "Microtubulestabilizing drugs from marine sponges : Focus on peloruside A and zampanolide", Mar Drugs, 8(4), pp.1059~1079 (2010)
- Miyaoka H, "Three new scalarane sesterterpenoids from the Okinawan sponge Hyrtios erectus", J Nat Prod, 63(10), pp.1369~1372 (2000)
- Pettit GR, "Antineoplastic agents 385. The isolation and structure of a scalaranetype sesterterpene from the Indian Ocean Porifera Hyrtios erecta", Collec Czech Chem C, 63(10), pp.1671~1677 (1998)
- Pettit GR, "Antineoplastic agents 397 : Isolation and structure of sesterstatins 4 and 5 from Hyrtios erecta(The Republic of Maldives)", Bioorg Med Chem Lett, 8(16), pp.2093~2098 (1998)
- Roy MC, "New scalarane class sesterterpenes from an Indonesian sponge, Phyllospongia sp", J Nat Prod, 65(12), pp.1838~1842 (2002)
- Ryu G, "Three new cytotoxic sesterterpenes from the marine sponge Hyrtios cf. erectus", J Nat Prod, 59(5), pp.515~517 (1996)
- Song J, "Scalarane sesterterpenes from the sponge Smenospongia sp", J Nat Prod, 71(11), pp.1866~1871 (2008)
- Ungur N, "Synthetic paths towards scalaranes : Assembling the scalaranic skeleton and further transformations", Phytochem Rev, 3(3), pp.401~415 (2004)
- Yu ZG, "Hyrtiosins A-E, five new scalarane sesterterpenes from the South China Sea sponge Hyrtios erecta", Helv Chim Acta, 88(5), pp.1004~1009 (2005)