Synthesis of two new hemisynthetic diterpenylhydroquinones from natural iiwf-Labdanes

Molecules

Volumn 14, Issue 6, 2009, Pages 2181-2194

  Catálan, Luis Espinoza ^a   Marin, Karen Catalan ^a   Villegas, Alejandro Madrid ^a   Altamirano, Héctor Carrasco ^b   Garcia, Joan Villena ^c   Fritis, Mauricio Cuellar ^c  

^a DEPARTAMENTO DE FÍSICA   (Chile)

^b UNIVERSIDAD ANDRÉS BELLO   (Chile)

^c UNIVERSIDAD DE VALPARAÍSO   (Chile)

Author keywords

Diterpenyl hydroquinones; E labdanes; Nmr structural determination; Synthesis

Indexed keywords

DITERPENE; HYDROQUINONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

DITERPENES; HYDROQUINONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 67649861550     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14062181     Document Type: Article

References (23)

1. Capon, R.J. Studies in Natural Products Chemistry. Structure and Chemistry, Part C; ur-Rahman, A., Ed.; Elsevier: Amsterdam, The Netherlands, 1995; Vol. 15, pp. 289-326.
2. De Rosa, S.; de Giulio, A.; Iodice, C. Biological Effects of Prenylated Hydroquinones: Structure- Activity Relationship Studies in Antimicrobial, Brine Shrimp, and Fish Lethality Assays. J. Nat. Prod. 1994, 57, 1711-1716.
3. Muller, W.E.G.; Maidhof, A.; Zahn, R.K.; Schroder, H.C.; Gasiae, M. J.; Heidemann, D.; Bernd, A.; Kurelec, B.; Eich, E.; Seibert, G. Potent Antileukemic Activity of the Novel Cytostatic Agent Avarone and Its Analogues in Vitro and in Vivo. Cancer Res. 1985, 45, 4822-4826.
4. Chen, C.Y.; Shen, Y.C.; Chen, Y.J.; Sheu, J.H.; Duh, C.Y. Bioactive Sesquiterpenes from A Taiwanese Marine Sponge Parahigginsia sp. J. Nat. Prod. 1999, 62, 573-576.
5. Shen, Y.C.; Hsieh, P.W. New Sesquiterpene Hydroquinones from a Taiwanese Marine Sponge Polyfibrospongia australis. J. Nat. Prod. 1997, 60, 93-97.
6. Talpir, R.; Rudi, A.; Kashman, Y. Three new Sesquiterpene Hydroquinones from Marine Origin. Tetrahedron 1994, 50, 4179-4184.
7. Prokofeva, N.G.; Utkina, N.K.; Chaikina, E.L.; Makarchenko, A.E. Biological Activities of Marine Sesquiterpenoid Quinones: Structure-Activity Relationships in Cytotoxic and Hemolytic Assays. Comp. Biochem. Physiol. Part B 2004, 139, 169-173.
8. Hamann, M.T.; Scheuer, P.J.; Kelly-Borges, K. Biogenetically Diverse, Bioactive Constituents of a Sponge, Order Verongida: Bromotyramines and Sesquiterpene-Shikimate Derived Metabolites J. Org. Chem. 1993, 55, 6565-6569.
9. Alvi, K.; Diaz, M.C.; Crews, P. Slate, D.L.; Lee, R.H.; Moretti, R. Evaluation of New Sesquiterpene Quinones from two Dysidea Sponge Species as Inhibitors of Protein Tyrosine Kinase. J. Org. Chem. 1992, 57, 6604-6607.
10. Schroder, H.C.; Sari, P.S.; Rottmann, M.; Wenger, R.; Maidhof, A.; Renneisen, K.; Muller, W.E.G. Differential Modulation of Host Cell and HIV Gene Expression by Combinations of Avarol and AZT in vitro. Biochem. Pharmacol. 1988, 37, 3947-3952.
11. Schroder, H.C.; Wenger, R.; Gerner, H.; Reuter, P.; Kuchino, Y.; Sladiae, D.; Muller, W.E.G. Suppression of the Modulatory Effects of the Antileukemic and Anti-Human Immunodeficiency Virus Compound Avarol on Gene Expression by Tryptophan. Cancer Res. 1989, 49, 2069-2076.
12. Loya, S.; Tal, R.; Kashman, Y.; Hizi, A. Illimaquinone, a Selective Inhibitor of the RNase H Activity of Human Immunodeficiency Virus Type 1 Reverse Transcriptase. Antimicrob. Agents Chemother. 1990, 34, 2009-2012.
13. Barrero, A.F.; Alvarez-Manzaneda, E.J.; Chahboun, R. Enantiospecific Synthesis of (+)- Puupehenone from (-)-sclareol and Protocatechualdehyde. Tetrahedron Lett. 1997, 38, 2325- 2328.
14. Seifert, K., Schroder, J., Matthes, B., Total Synthesis of the Marine Sesquiterpene Quinone (-)- cyclozonarone. Tetrahedron Lett. 2001, 42, 8151-8152.
15. Cortes, M.; Valderrama, J.A.; Cuellar, M.; Armstrong, V.; Preite, M.; Synthesis of (+)- Cyclozonarone and the Absolute Configuration of Naturally Occurring (-)-Cyclozonarone. J. Nat. Prod. 2001, 64, 348-349.
16. Poigny, S.; Guyot, M.; Samadi, M.; Efficient Total Synthesis of (-)-Ilimaquinone. J. Org. Chem. 1998, 63, 5890-5894.
17. Laube, T.; Beil, W.; Seifert, K. Total Synthesis of two 12-nordrimanes and the Pharmacological Active Sesquiterpene Hydroquinone Yahazunol. Tetrahedron 2005, 67, 1141-1148.
18. Almeida, W.P.; Correira, C.R.D. Stereoselective Total Synthesis and Enantioselective Formal Synthesis of the Antineoplastic Sesquiterpene Quinone Metachromin A. J. Braz. Chem. Soc. 1999, 70, 401-414.
19. Gonzalez, A.G.; Martin, J.D. Thes Synthesis of a Taondiol Derivative. Tetrahedron Lett. 1972, 22, 2259-2260.
20. Gonzalez, A.G.; Darias, J.; Martin, J.D.; Pascual, C. Marine Natural Products of the Atlantic Zone-V. The Structure and Chemistry of Taondiol and Related Compounds. Tetrahedron 1973, 29, 1605-1609.
21. Espinonza, L.; Carrasco, H.; Cuellar, M.; Gallardo, C.; Catalan, K. Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part I. Molecules 2007, 72, 318-327.
22. Bastard, J.; Duc-Khac, D.; Fetizon, M. CMR Spectroscopy of Labdanic Diterpenes and Related Substances. J. Nat. Prod. 1984, 47, 592-599.
23. Forster, P.G.; Ghisalberti, E.L.; Jefferies, P.R. Labdane Diterpenes from an Acacia Species. Photochemistry 1985, 24, 2991-2993.