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DOI: 10.1055/s-2006-931554
Two New Cytotoxic Naphthoquinones from Mendoncia cowanii from the Rainforest of Madagascar
Publication History
Received: October 27, 2005
Accepted: January 10, 2006
Publication Date:
24 April 2006 (online)
Abstract
Bioassay-guided fractionation of the root and stem extracts of Mendoncia cowanii led to the isolation of two new and two known naphthoquinones. The structures of the new compounds, avicequinones D and E (1 and 2), were determined using 1D and 2D NMR spectroscopy and by chemical conversion of compound 1 to 2. The new compounds were active in the A2780 human ovarian cancer cell line with IC50 values of 7.4 - 50 μM, respectively, and 1, 3, and 4 were subsequently found to be weakly active in an assay for inhibition of the kinase Akt.
References
-
1 Biodiversity, conservation and drug discovery in Madagascar. Part 19, this manuscript. For part 18. Cao S, Radwan MM, Norris A, Miller JS, Ratovoson F, Mamisoa A et al
Cytotoxic and other compounds from Didymochlaena truncatula from the Madagascar rain forest . J Nat Prod 2006 69: 284-6 -
2 Missouri Botanical Garden. Available at http://mobot.mobot.org/cgi-bin/search_vast?ssdp = 01 885 737. Accessed in 2005.
- 3 Ito C, Katsuno S, Kondo Y, Tan H T-W, Furukawa H. Chemical constituents of Avicennia alba. Isolation and structural elucidation of new naphthaquinones and their analogs. Chem Pharm Bull. 2000; 48 339-43
- 4 Mock J, Murphy S T, Ritchie E, Taylor W C. Chemical studies of the Proteateae VI. Two naphthaquinones from Stenocarpus salignus . Aust J Chem. 1973; 26 1121-30
- 5 Thomson R H. Naturally occurring quinones. 2nd edition New York; Academic Press 1971: p 49-57
- 6 Zhou H, Li X -M, Meinkoth J, Pittman R N. Akt regulates cell survival and apoptosis at a postmitochondrial level. J Cell Biol. 2000; 151 483-94
- 7 Datta S R, Brunet A, Greenberg M E. Cellular survival: a play in three Akts. Genes Dev. 1999; 13 2905-27
- 8 Cardone M H, Roy N, Stennicke H R, Salvesen G S, Franke T F, Stanbridge E. et al . Regulation of cell death protease caspase-9 by phosphorylation. Science. 1998; 282 1318-21
- 9 Tran H, Brunet A, Grenier J M, Datta S R, Fornace Jr. A J, DiStefano P S. et al . DNA repair pathway stimulated by the forkhead transcription factor FOXO3a through the Gadd45 protein. Science. 2002; 296 530-4
- 10 Brunet A, Bonni A, Zigmond M J, Lin M Z, Juo P, Hu L S. et al . Akt promotes cell survival by phosphorylating and inhibiting a forkhead transcription factor. Cell. 1999; 96 857-68
- 11 Williams R B, Norris A, Slebodnick C, Merola J, Miller J S, Andriantsiferana R. et al . Cytotoxic sesquiterpene lactones from Vernonia pachyclada from the Madagascar rainforest. J Nat Prod. 2005; 68 1371-4
- 12 Ferreira V F, Pinto A V, Pinto M CFR, Silva M M. Selective reduction in pyranonaphthoquinone systems. J Chem Res Synop 1987: 26
- 13 Louie K G, Behrens B C, Kinsella T J, Hamilton T C, Grotzinger K R, McKoy W M. et al . Radiation survival parameters of antineoplastic drug-sensitive and -resistant human ovarian cancer cell lines and their modification by buthionine sulfoximine. Cancer Res. 1985; 45 2110-5
Prof. Dr. David G. I. Kingston
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