Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus
作者： Louise C. Forster , Gregory K. Pierens , Andrew M. White , Karen L. Cheney , Pradeep Dewapriya
关键词: Lactone 、 Diterpene 、 Cytotoxicity 、 Cancer cell 、 Biosynthesis 、 Cytotoxic T cell 、 Bond cleavage 、 Molecular model 、 Chemistry 、 Stereochemistry
摘要: Epoxygoniolide-1 (1), possessing spiroepoxide lactone, enal, and masked dialdehyde functionalities, has been characterized from the conspicuously patterned mollusc Goniobranchus splendidus. Its relative configuration was investigated by spectroscopic analyses, molecular modeling, density functional theory calculations. The biosynthesis of 1 may involve rearrangement a diterpene framework, providing precursor to cometabolite gonioline (2), followed C–C bond cleavage (via Grob or P450 mechanism). Moderate cytotoxicity NCIH-460, SW60, HepG2 cancer cells observed for norditerpene 1.
acs.org
uq.edu.au
figshare.com
core.ac.uk 参考文章(40)
Luciano Mayol, Vincenzo Piccialli, Donato Sica, Metabolites from the marine sponge . Three further nor-diterpenes, one of them based on a novel carbocyclic skeleton. Tetrahedron. ,vol. 42, pp. 5369- 5376 ,(1986) , 10.1016/S0040-4020(01)82087-1
L. Mayol, V. Piccialli, D. Sica, Gracilin A, an unique: nor-diterpene metabolite from the marine sponge . Tetrahedron Letters. ,vol. 26, pp. 1357- 1360 ,(1985) , 10.1016/S0040-4039(00)94893-7
Xu-Ming Mao, Zha-Jun Zhan, Matthew N. Grayson, Man-Cheng Tang, Wei Xu, Yong-Quan Li, Wen-Bing Yin, Hsiao-Ching Lin, Yit-Heng Chooi, K. N. Houk, Yi Tang, Efficient Biosynthesis of Fungal Polyketides Containing the Dioxabicyclo-octane Ring System Journal of the American Chemical Society. ,vol. 137, pp. 11904- 11907 ,(2015) , 10.1021/JACS.5B07816
James J. De Voss, Max J. Cryle, Carbon-carbon bond cleavage by P450 systems Metal ions in life sciences. ,vol. 3, pp. 397- 435 ,(2007) , 10.1002/9780470028155.CH13
Yuichiro Hirayama, Peter L. Katavic, Andrew M. White, Gregory K. Pierens, Lynette K. Lambert, Anne E. Winters, Hideo Kigoshi, Masaki Kita, Mary J. Garson, New Cytotoxic Norditerpenes from the Australian Nudibranchs Goniobranchus Splendidus and Goniobranchus Daphne Australian Journal of Chemistry. ,vol. 69, pp. 136- 144 ,(2016) , 10.1071/CH15203
Ana Rueda, Alejandro Losada, Rogelio Fernandez, Carlos Cabanas, Luis F. Garcia- Fernandez, Fernando Reyes, Carmen Cuevas, Gracilins G-I, Cytotoxic Bisnorditerpenes from Spongionella pulchella, and the Anti-Adhesive Properties of Gracilin B Letters in Drug Design & Discovery. ,vol. 3, pp. 753- 760 ,(2006) , 10.2174/157018006778631875
Andrew R. Gallimore, The biosynthesis of polyketide-derived polycyclic ethers. Natural Product Reports. ,vol. 26, pp. 266- 280 ,(2009) , 10.1039/B807902C
Eric J. Dumdei, E. Dilip De Silva, Raymond J. Andersen, M. Iqbal Choudhary, Jon Clardy, Chromodorolide A, a rearranged diterpene with a new carbon skeleton from the Indian Ocean nudibranch Chromodoris cavae Journal of the American Chemical Society. ,vol. 111, pp. 2712- 2713 ,(1989) , 10.1021/JA00189A055
Kathrin Prantz, Johann Mulzer, Synthetic Applications of the Carbonyl Generating Grob Fragmentation Chemical Reviews. ,vol. 110, pp. 3741- 3766 ,(2010) , 10.1021/CR900386H
Liliana Betancur-Galvis, Carmen Zuluaga, Manuel Arnó, Miguel A. González, Ramón J. Zaragozá, Cytotoxic effect (on tumor cells) and in vitro antiviral activity against herpes simplex virus of synthetic spongiane diterpenes. Journal of Natural Products. ,vol. 65, pp. 189- 192 ,(2002) , 10.1021/NP010206T