Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

New Cytotoxic Norditerpenes from the Australian Nudibranchs Goniobranchus Splendidus and Goniobranchus Daphne

Yuichiro Hirayama A E , Peter L. Katavic B , Andrew M. White B , Gregory K. Pierens C , Lynette K. Lambert C , Anne E. Winters D , Hideo Kigoshi A , Masaki Kita A F and Mary J. Garson B F
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571, Japan.

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

C Centre for Advanced Imaging, The University of Queensland, Brisbane, Qld 4072, Australia.

D School of Biological Sciences, The University of Queensland, Brisbane, Qld 4072, Australia.

E Current address: Department of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.

F Corresponding authors. Email: mkita@chem.tsukuba.ac.jp; m.garson@uq.edu.au

Australian Journal of Chemistry 69(2) 136-144 https://doi.org/10.1071/CH15203
Submitted: 21 April 2015  Accepted: 10 July 2015   Published: 27 August 2015

Abstract

This study reports the isolation and characterisation of six new metabolites with ‘gracilin’-type carbon skeletons and of aplytandiene-3 from the Australian nudibranch Goniobranchus splendidus. The structure of gracilin G is revised, and the C-6 configuration deduced by comparison of calculated 3JC/H values with values measured using the EXSIDE pulse sequence. A lactone isolated from Goniobranchus daphne contains a rearranged spongionellin-type skeleton. Screening of selected metabolites revealed significant cytotoxicity against a HeLa S3 cell line by five of the new terpenes.


References

[1]  See p. 72 in N. Coleman, 1001 Nudibranchs: Catalogue of Indo-Pacific Sea Slugs 2001 (Neville Coleman’s Underwater Geographic Pty Ltd: Springwood).

[2]  R. A. Keyzers, P. T. Northcote, M. T. Davies-Coleman, Nat. Prod. Rep. 2006, 23, 321.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XksVyrtL0%3D&md5=38376ee9eb2613ef14b43c7cae272857CAS | 16572231PubMed |

[3]  M. L. Schnermann, C. M. Beaudry, A. V. Egorova, R. S. Polsichuk, C. Sütterlin, L. E. Overman, Proc. Natl. Acad. Sci. USA 2010, 107, 6158.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXkslyntbw%3D&md5=b4304025c5d9e0ea4c0ad8a3a52c5f48CAS |

[4]  T. P. Brady, E. K. Wallace, S. H. Kim, G. Guizzunti, V. Malhotra, E. A. Theodorakis, Bioorg. Med. Chem. Lett. 2004, 14, 5035.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXns1Ohtb8%3D&md5=0c4ab662b64da69e501a827d14a35253CAS | 15380194PubMed |

[5]  T. P. Brady, S. H. Kim, K. Wen, E. K. Theodorakis, Angew. Chem. Int. Ed. 2004, 43, 739.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhsVKqsb0%3D&md5=c43583e9298ddbb066d55bd07dd60d99CAS |

[6]  W. Rungprom, W. Chavasiri, U. Kokpul, A. Kotze, M. J. Garson, Mar. Drugs 2004, 2, 101.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXptValuro%3D&md5=a5dec8572ef28fdd1503c3ba1b5a4b42CAS |

[7]  S. A. Morris, E. J. Dumdei, E. D. de Silva, R. J. Andersen, Can. J. Chem. 1991, 69, 768.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXkvV2nt74%3D&md5=462b55c4c0fb49201fd3b506becb3810CAS |

[8]  A. Rueda, A. Losada, R. Fernández, C. Cabañas, L. F. Garcia-Fernández, F. Reyes, C. Cuevas, Lett. Drug Des. Discov. 2006, 3, 753.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtF2qsLjM&md5=2b5f63e4b402e92f775651ecffd45cb4CAS |

[9]  M. E. Rateb, W. E. Houssen, M. Schumacher, W. T. A. Harrison, M. Diederich, R. Ebel, M. Jaspars, J. Nat. Prod. 2009, 72, 1471.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXosVOnsLY%3D&md5=f9062a1e1d1aa4d1c3f34ad73a595331CAS | 19601607PubMed |

[10]  M. Leiros, E. Alonso, M. E. Rateb, W. E. Houssen, R. Ebel, M. Jaspars, A. Alfonso, L. M. Botana, Neuropharmacology 2015, 93, 285.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXjs1Olu7g%3D&md5=2ac5f698568fd23e9b1c8a68a7622455CAS | 25724081PubMed |

[11]  B. M. Potts, D. J. Faulkner, R. S. Jacobs, J. Nat. Prod. 1992, 55, 1701.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXjsVOqsg%3D%3D&md5=aeb170fce37bf50a22f88d2fb4b971c3CAS |

[12]  K. W. L. Yong, A. A. Salim, M. J. Garson, Tetrahedron 2008, 64, 6733.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXnt1KqtLk%3D&md5=d5ecd1d05ad9a43c876ed059e05e78baCAS |

[13]  L. K. Suciati, M. J. Lambert, Garson, Aust. J. Chem. 2011, 64, 489.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXkvVCrsL8%3D&md5=e6fda76f674b03190f711bbf085f696dCAS |

[14]  P. L. Katavic, P. Jumaryatno, J. N. A. Hooper, J. T. Blanchfield, M. J. Garson, Aust. J. Chem. 2012, 65, 531.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xns1yrsbw%3D&md5=2f1d5193712a116df5a16d74580bf675CAS |

[15]  L. Mayol, V. Piccialli, D. Sica, Tetrahedron Lett. 1985, 26, 1357.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXitFyltrg%3D&md5=bbf81abed7dabfb5ec041cf580bc74b6CAS |

[16]  L. Mayol, V. Piccialli, D. Sica, J. Nat. Prod. 1986, 49, 823.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXhsFegtbw%3D&md5=6e5e13f340e1967f11e4a3becf0d8e69CAS |

[17]  P. Karuso, B. W. Skelton, W. C. Taylor, A. H. White, Aust. J. Chem. 1984, 37, 1081.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXkvVOlt7s%3D&md5=56bc3e46ac81933b543fe12c90956b77CAS |

[18]  S. K. Graham, M. J. Garson, P. V. Bernhardt, J. Chem. Crystallogr. 2010, 40, 468.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXkt1Cit7g%3D&md5=eae9e8869efc7af6bf0f1220059c9c4bCAS |

[19]  M. R. Kernan, R. C. Cambie, P. R. Bergquist, J. Nat. Prod. 1990, 53, 724.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXlsV2isb4%3D&md5=a7de7671bdb9597ee617999a4aedd559CAS |

[20]  P. Karuso, W. C. Taylor, Aust. J. Chem. 1986, 39, 1629.
         | 1:CAS:528:DyaL2sXjtVahug%3D%3D&md5=de61f897abc5aca1ad032ad7ca792385CAS |

[21]  P. Karuso, P. R. Bergquist, R. C. Cambie, J. S. Buckleton, G. R. Clark, C. E. F. Rickard, Aust. J. Chem. 1986, 39, 1643.
         | 1:CAS:528:DyaL2sXjtVahuw%3D%3D&md5=230e8fde7167920b9bd2797c03919115CAS |

[22]  F. J. Schmitz, J. S. Chang, M. B. Hossain, D. van der Helm, J. Org. Chem. 1985, 50, 2862.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXks1ynurg%3D&md5=23bbb6a1dbcc22b7757b8c7ef5a9412fCAS |

[23]  E. J. Corey, M. A. Levatic, J. Am. Chem. Soc. 1995, 117, 9616.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXnvFOktL4%3D&md5=4afd316e17e36b9d59ecd09f1a4c69c5CAS |

[24]  MacroModel, version 10.0 2013 (Schrödinger, LLC: New York, NY).

[25]  Jaguar, version 8.0 2013 (Schrödinger, LLC: New York, NY).

[26]  R. Aydin, H. Günther, Magn. Reson. Chem. 1990, 28, 448.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXltlWhu7Y%3D&md5=20caa9fd0fe4c1b32dc003ea42d26ba1CAS |

[27]  V. V. Krishnamurthy, J. Magn. Reson. 1996, 121, 33.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xkt1ektrw%3D&md5=b5ba06b2bd896112aa45d983c39f4e75CAS |

[28]  R. Puliti, A. Fontana, G. Cimino, Acta Crystallogr. 1993, C49, 1373.
         | 1:CAS:528:DyaK3sXmslWnsLg%3D&md5=125b375f42141073ed30a612a04fe62bCAS |

[29]  A. Poiner, W. C. Taylor, Aust. J. Chem. 1990, 43, 1713.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXlvFWnuw%3D%3D&md5=20502fe7fef9d3e8145b229368eb3fd2CAS |

[30]  J. E. Hochlowski, D. J. Faulkner, G. K. Matsumoto, J. Clardy, J. Org. Chem. 1983, 48, 1141.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXhsVSrs70%3D&md5=ac522b7a97936802d211a8d284ed20c1CAS |

[31]  T. F. Molinski, D. J. Faulkner, H. Cun-heng, G. D. Van Duyne, J. Clardy, J. Org. Chem. 1986, 51, 4564.
         | Crossref | GoogleScholarGoogle Scholar |

[32]  S. C. Bobzin, D. J. Faulkner, J. Org. Chem. 1989, 54, 5727.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXmt12hu78%3D&md5=f2a5a04f572900eabb203cf010c82ac4CAS |

[33]  I. W. Mudianta, A. M. White, M. J. Garson, Nat. Prod. Commun. 2015, in press
         | 26197502PubMed |

[34]  T. Bally, P. R. Rablen, J. Org. Chem. 2011, 76, 4818.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXmt1Ghu70%3D&md5=277f8838e5dd1fd6477d9e86bdae6668CAS | 21574622PubMed |