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RESEARCH ARTICLE

Oxygenated Terpenoids from the Australian Sponges Coscinoderma matthewsi and Dysidea sp., and the Nudibranch Chromodoris albopunctata

Peter L. Katavic A , Pinus Jumaryatno A B , John N. A. Hooper C , Joanne T. Blanchfield A and Mary J. Garson A D
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.

B Pharmacy Department, Faculty of Mathematics and Natural Sciences, Universitas Islam Indonesia, Yogyakarta, Indonesia.

C Queensland Museum, PO Box 3300, South Brisbane, Qld 4101, Australia.

D Corresponding author. Email: m.garson@uq.edu.au

Australian Journal of Chemistry 65(5) 531-538 https://doi.org/10.1071/CH12010
Submitted: 13 January 2012  Accepted: 3 April 2012   Published: 28 May 2012

Abstract

The isolation and structure elucidation of seven new oxygenated terpenoids and eight known terpene metabolites from marine invertebrates collected at the Inner Gneerings Reef, South East Queensland, is discussed. Investigation of the sponge Coscinoderma matthewsi yielded an epoxylactone derivative (1) of the known furanoterpene tetradehydrofurospongin-1 (2). A chemical investigation of the dissected nudibranch Chromodoris albopunctata provided the new oxygenated diterpenes 12α-acetoxyspongian-16-one (10), 20-acetoxyspongian-16-one (12), 20-oxyspongian-16-one propionate (13) and 12α,20-dioxyspongian-16-one dipropionate (14) in conjunction with three other known diterpene metabolites, while two new chromodorolides, D (17) and E (18), in addition to four known diterpenes were isolated from a Dysidea sp.


References

[1]  G. Cimino, A. Fontana, A. Cutignano, M. Gavagnin, Phytochem. Rev. 2004, 3, 285.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXkvF2js70%3D&md5=184e3de5b1025b72e716826391ddb418CAS |

[2]  M. Gavagnin, A. Fontana, Curr. Org. Chem. 2000, 4, 1201.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXntVaqsw%3D%3D&md5=6caa0d017c363b1aa4d3a25dd6d18fbfCAS |

[3]  G. Cimino, Phytochem. Rev. 2010, 9, 547.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtlyktbnN&md5=b72e50a67815e016fee782e74eccb996CAS |

[4]  (a) M. A. González, Curr. Bioact. Comp. 2007, 3, 1.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) R. A. Keyzers, P. T. Northcote, M. T. Davies-Coleman, Nat. Prod. Rep. 2006, 23, 321.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) M. Hyosu, J. Kimura, J. Nat. Prod. 2000, 63, 422.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXhsVWju7Y%3D&md5=777c7220866c2918bf8a1898ec050ca8CAS |
      (b) S. De Marino, C. Festa, M. V. D’Auria, M.-L. Bourguet-Kondracki, S. Petek, C. Debitus, R. M. Andres, M. C. Terenico, M. Paya, A. Zampella, Tetrahedron 2009, 65, 2905.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. Loukaci, I. Le Saout, M. Samadi, S. Leclerc, E. Damiens, L. Meijer, C. Debitus, M. Guyot, Bioorg. Med. Chem. 2001, 9, 3049.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. Kimura, M. Hyosu, Chem. Lett. 1999, 28, 61.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) J. Kimura, E. Ishizuka, Y. Nakao, W. Y. Yoshida, P. J. Scheuer, M. Kelly-Borges, J. Nat. Prod. 1998, 61, 248.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) J. Kimura, E. Ishizuka, Y. Nakao, W. Y. Yoshida, P. J. Scheuer, M. Kelly-Borges, J. Nat. Prod. 1998, 61, 862.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  K. W. L. Yong, J. N. A. Hooper, M. J. Garson, ARKIVOC 2008, vi, 100.

[7]  A. Fontana, L. Albarella, G. Scognamiglio, M. Uriz, G. Cimino, J. Nat. Prod. 1996, 59, 869.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XltlWntLY%3D&md5=f1da7c8b66ff3b7e0a09b2fc1b91621aCAS |

[8]  I. A. van Altena, D. A. Miller, Aust. J. Chem. 1989, 42, 2181.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXhsFGnurk%3D&md5=2f29abe77ee51caf8f56552d2061b640CAS |

[9]  N. H. Tran, J. N. A. Hooper, R. J. Capon, Aust. J. Chem. 1995, 48, 1757.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  G. Cimino, S. De Stefano, L. Minale, Experientia 1974, 30, 18.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2cXhtlSks7o%3D&md5=92c18d58559e08572421ef6e6da3b1d4CAS |

[11]  X.-D. Luo, S.-H. Wu, Y.-B. Ma, D.-G. Wu, J. Nat. Prod. 2000, 63, 947.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXjsF2qsLs%3D&md5=742dac5080837387ac36f4ef89124efcCAS |

[12]  M. R. Kernan, D. J. Faulkner, J. Org. Chem. 1988, 53, 2773.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXktVKktLw%3D&md5=665660da57d614b4d448c1864d350505CAS |

[13]  C. J. Barrow, J. W. Blunt, M. H. G. Munro, J. Nat. Prod. 1989, 52, 346.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXmtlehtbg%3D&md5=1f338bce7274054f2ad82ccf10c3a4c7CAS |

[14]  K. W. L. Yong, A. A. Salim, M. J. Garson, Tetrahedron 2008, 64, 6733.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXnt1KqtLk%3D&md5=e22a1c974c28977e7a1b12cf2d784d94CAS |

[15]  Suciati, L. K., Lambert, M. J. Garson, Aust. J. Chem. 2011, 64, 757.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  M. R. Kernan, R. C. Cambie, P. R. Bergquist, J. Nat. Prod. 1990, 53, 724.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXlsV2isb4%3D&md5=83f555875de2274e947dc6053a9485caCAS |

[17]  P. Karuso, W. C. Taylor, Aust. J. Chem. 1986, 39, 1629.
         | 1:CAS:528:DyaL2sXjtVahug%3D%3D&md5=a712c13fe682bd83dffee488215338e4CAS |

[18]  G. Cimino, D. De Rosa, S. De Stefano, L. Minale, Tetrahedron 1974, 30, 645.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2cXkslyisrc%3D&md5=20d1dac0860be5ea0a5bae829ca548f2CAS |

[19]  T. Miyamoto, K. Sakamoto, H. Amano, Y. Arakawa, Y. Nagarekawa, T. Komori, R. Higuchi, T. Sasaki, Tetrahedron 1999, 55, 9133.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXks1WqtLc%3D&md5=92406c9f3a4c925f6cefda83e9bc5d19CAS |

[20]  E. Manzo, M. Gavagnin, M. J. Somerville, S.-C. Mao, M. L. Ciavatta, E. Mollo, P. J. Schupp, M. J. Garson, G. Cimino, J. Chem. Ecol. 2007, 33, 2325.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtl2ks7rO&md5=9bac5681a2e667661ec52c77275dfb68CAS |

[21]  W. C. Taylor, S. Toth, Aust. J. Chem. 1997, 50, 895.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXns1Sqsb0%3D&md5=3968eca429b48ccd89250072d78f5ac5CAS |

[22]  M. Arnó, M. A. González, R. J. Zaragozá, J. Org. Chem. 2003, 68, 1242.
         | Crossref | GoogleScholarGoogle Scholar |

[23]  A. J. Blake, M. A. González, M. J. Gil-Gimeno, Acta Crystallogr. 2006, C62, o208.
         | 1:CAS:528:DC%2BD28XjtFOqsbo%3D&md5=64c6edff34ce458896414c408fa34c13CAS |

[24]  K. Gustafson, R. J. Andersen, H. Cun-Heng, J. Clardy, Tetrahedron Lett. 1985, 26, 2521.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXks1ynurk%3D&md5=b67bb9029cbf74f97394168a69a35954CAS |

[25]  E. J. Dumdei, J. Kubanek, J. E. Coleman, J. Pika, R. J. Andersen, J. R. Steiner, J. Clardy, Can. J. Chem. 1997, 75, 773.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXkslKrtLg%3D&md5=7ca0bb4bb5c9a4592b35c90eea7bc173CAS |

[26]  A. R. Carroll, J. Lamb, R. Moni, J. N. A. Hooper, R. J. Quinn, J. Nat. Prod. 2008, 71, 884.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXksFyktrk%3D&md5=589ce2d4fa9e5eb466346ae323121f97CAS |

[27]  MARINLIT database, Department of Chemistry, University of Canterbury: http://www.chem.canterbury.ac.nz/marinlit/marinlit.html.

[28]  K. H. Jang, J. Jeon, S. Ryu, H.-S. Lee, K.-B. Oh, J. Shin, J. Nat. Prod. 2008, 71, 1701.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtFGjsL%2FI&md5=36009dfbf3f7e6c91f6fa5719b442ea6CAS |

[29]  B. C. M. Potts, D. J. Faulkner, J. Am. Chem. Soc. 1991, 113, 6321.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXkvVCru74%3D&md5=bc49a5b03c04a0471b24dc2b91ac5b70CAS |

[30]  C. M. Ireland, J. E. Biskupiak, G. J. Hite, M. Rapposch, P. J. Scheuer, J. R. Ruble, J. Org. Chem. 1984, 49, 559.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXhtVShsr4%3D&md5=cd0537365f3c351fb3dbaad005684a55CAS |

[31]  J. Rodriguez, R. Riguera, C. Debitus, J. Org. Chem. 1992, 57, 4624.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38Xls1OqtLs%3D&md5=58844dc04b076a5d1b37e9b8fd4866bfCAS |

[32]  R. N. Asolkar, R. P. Maskey, E. Helmke, H. Laatsch, J. Antibiot. 2002, 55, 893.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XotlChs78%3D&md5=7f8306a5deebb026591128d33185fffdCAS |

[33]  K. W. L. Yong, M. J. Garson, P. V. Bernhardt, Acta Crystallogr. 2009, C65, o167.
         | 1:CAS:528:DC%2BD1MXktVKhsrs%3D&md5=97fc0d5add20ebb44d528945a0d71ee3CAS |

[34]  The specific rotation of 7α-acetoxyspongian-16-one (8) was not published;[17] however, our sample gave –34.7 (c 0.047, CHCl3).

[35]  A. G. Gonzalez, D. M. Estrada, J. D. Martin, V. S. Martin, C. Perez, R. Perez, Tetrahedron 1984, 40, 4109.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXht12isLY%3D&md5=eb0f3dcb6baedee07723a9e5fa9efe84CAS |

[36]  A. Rudi, Y. Kashman, Tetrahedron 1990, 46, 4019.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXlt12mt7c%3D&md5=bf39e99db2bcd0efc498905cedd97c71CAS |

[37]  E. J. Dumdei, E. D. de Silva, R. J. Andersen, M. I. Choudhary, J. Clardy, J. Am. Chem. Soc. 1989, 111, 2712.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXhslSntro%3D&md5=24e120bd775a05acd0f6ca95f0e493dfCAS |

[38]  S. A. Morris, E. D. de Silva, R. J. Andersen, Can. J. Chem. 1991, 69, 768.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXkvV2nt74%3D&md5=3585ddf969b0e0d39f734d86900db36aCAS |

[39]  W. Rungprom, W. Chavasiri, U. Kokpol, A. Kotze, M. J. Garson, Mar. Drugs 2004, 2, 101.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXptValuro%3D&md5=10603a4a1f8f2f50e0090d57bf055d28CAS |

[40]  Suciati, L. K., Lambert, B. P., Ross, M. A., Deseo, M. J., Garson, Aust. J. Chem. 2011, 64, 489.
         | Crossref | GoogleScholarGoogle Scholar |

[41]  N. Coleman, 1001 Nudibranchs: Catalogue of Indo-Pacific Sea Slugs 2000, p. 67 (Neville Coleman’s Underwater Geographic: Springwood, Qld).