Synthesis and bioactivity of Luffarin I

Marine Drugs

Volumn 13, Issue 4, 2015, Pages 2407-2423

  Urosa, Aitor ^a   Marcos, Isidro S ^a   Díez, David ^a   Lithgow, Anna ^a   Plata, Gabriela B ^b   Padrón, José M ^b   Basabe, Pilar ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

Diastereoselective reduction; Luffarin I; Marine metabolites; Sclareol; Sesterterpenolide; Sponges

Indexed keywords

19,20 EPOXY LUFFARA 8,17(20),18 TETRAEN 21,OLIDE; 19,20 EPOXY LUFFARA 8,17(20),18 TETRAENE 21 DIOL; 21 TRIHYDROXY LUFFARA 8,17 TRIEN 19,20 OLIDE; ANTINEOPLASTIC AGENT; CISPLATIN; DRUG ANALOG; ETOPOSIDE; LUFFARIN I; UNCLASSIFIED DRUG; DITERPENE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FURAN DERIVATIVE; GAMMA BUTYROLACTONE; SCLAREOL; SESTERTERPENE;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CANCER INHIBITION; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IN VITRO STUDY; LUFFARIELLA GEOMETRICA; SPONGE (PORIFERA); ANALOGS AND DERIVATIVES; ANIMAL; AUSTRALIA; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECTS; NEOPLASMS; OSMOLARITY; PACIFIC OCEAN; PATHOLOGY; STEREOISOMERISM; SYNTHESIS; TUMOR CELL LINE;

LUFFARIELLA;

4-BUTYROLACTONE; ANIMALS; ANTINEOPLASTIC AGENTS; AUSTRALIA; CELL LINE, TUMOR; CELL PROLIFERATION; DITERPENES; FURANS; HUMANS; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NEOPLASMS; OSMOLAR CONCENTRATION; PACIFIC OCEAN; PORIFERA; SESTERTERPENES; STEREOISOMERISM;

EID: 84928326052     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md13042407     Document Type: Article

References (42)

1. Ebada, S.S.; Lin, W.H.; Proksch, P. Bioactive sesterterpenes and triterpenes from marine sponges: Occurrence and pharmacological significance. Mar. Drugs 2010, 8, 313-346.
2. Braekman, J.C.; Daloze, D. Chemical defense in sponges. Pure Appl. Chem. 1986, 58, 357-364.
3. Wang, L.; Yang, B.; Lin, X.-P.; Zhou, X.-F.; Liu, Y. Sesterterpenoids. Nat. Prod. Rep. 2013, 30, 455-473.
4. Youssef, D.T.A.; Yamaki, R.K.; Kelly, M.; Scheuer, P.J. Salmahyrtisol a, a novel cytotoxic sesterterpene from the Red Sea Sponge Hyrtios erecta. J. Nat. Prod. 2002, 65, 2-6.
5. Villa, F.A.; Gerwick, L. Marine natural product drug discovery: Leads for treatment of inflammation, cancer, infections, and neurological disorders. Immunopharmacol. Immunotoxicol. 2010, 32, 228-237.
6. Wang, Q.-X.; Bao, L.; Yang, X.-L.; Liu, D.-L.; Guo, H.; Dai, H.-Q.; Song, F.-H.; Zhang, L.-X.; Guo, L.-D.; Li, S.-J.; et al. Ophiobolins p-t, five new cytotoxic and antibacterial sesterterpenes from the endolichenic fungus Ulocladium sp. Fitoterapia 2013, 90, 220-227.
7. Kazlauskas, R.; Murphy, P.T.; Wells, R.J. Five new c26 tetracyclic terpenes from a sponge (Lendenfeldia sp.). Aust. J. Chem. 1982, 35, 51-59.
8. Marwaha, A.; Goel, R.K.; Mahajan, M.P. Pass-predicted design, synthesis and biological evaluation of cyclic nitrones as nootropics. Bioorg. Med. Chem. Lett. 2007, 17, 5251-5255.
9. Schumacher, M.; Juncker, T.; Schnekenburger, M.; Gaascht, F.; Diederich, M. Natural compounds as inflammation inhibitors. Genes Nutr. 2011, 6, 89-92.
10. Guerrero, M.D.; Aquino, M.; Bruno, I.; Terencio, M.C.; Paya, M.; Riccio, R.; Gomez-Paloma, L. Synthesis and pharmacological evaluation of a selected library of new potential anti-inflammatory agents bearing the γ-hydroxybutenolide scaffold: A new class of inhibitors of prostanoid production through the selective modulation of microsomal prostaglandin e synthase-1 expression. J. Med. Chem. 2007, 50, 2176-2184.
11. Butler, M.S.; Capon, R.J. The luffarins (a-z), novel terpenes from an Australian marine sponge, Luffariella geometrica. Aust. J. Chem. 1992, 45, 1705-1743.
12. Basabe, P.; Bodero, O.; Marcos, I.S.; Diez, D.; Blanco, A.; de Roman, M.; Urones, J.G. Yamaguchi-type lactonization as a key step in the synthesis of marine metabolites: (+)-luffalactone. J. Org. Chem. 2009, 74, 7750-7754.
13. Ruzicka, L.; Seidel, C.F.; Engel, L.L. Diterpenes. Liii. Oxidation of sclareol with potassium permanganate. Helv. Chim. Acta 1942, 25, 621-630.
14. Leite, M.A.F.; Sarragiotto, M.H.; Imamura, P.M.; Marsaioli, A.J. Absolute configuration of drim-9(11)-en-8-ol from aspergillus oryzae. J. Org. Chem. 1986, 51, 5409-5410.
15. Marcos, I.S.; Laderas, M.; Diez, D.; Basabe, P.; Moro, R.F.; Garrido, N.M.; Urones, J.G. Synthesis and absolute configuration of (-)-chrysolic acid and (+)-isofregenedol. Tetrahedron Lett. 2003, 44, 5419-5422.
16. Hua, S.-K.; Wang, J.; Chen, X.-B.; Xu, Z.-Y.; Zeng, B.-B. Scalable synthesis of methyl ent-isocopalate and its derivatives. Tetrahedron 2011, 67, 1142-1144.
17. Oppolzer, W.; Sarkar, T.; Mahalanabis, K.K. A simple alkylative 1,2-carbonyl transposition of cyclohexenones. Helv. Chim. Acta 1976, 59, 2012-2020.
18. Moriarty, R.M.; Hou, K.C. A-hydroxylation of ketones using o-iodosylbenzoic acid. Tetrahedron Lett. 1984, 25, 691-694.
19. Carneiro, V.M.T.; Ferraz, H.M.C.; Vieira, T.O.; Ishikawa, E.E.; Silva, L.F., Jr. A ring contraction strategy toward a diastereoselective total synthesis of (+)-bakkenolide a. J. Org. Chem. 2010, 75, 2877-2882.
20. Davies, H.M.L.; Jin, Q. Intermolecular c-h activation at benzylic positions: Synthesis of (+)-imperanene and (-)-α-conidendrin. Tetrahedron: Asymmetry 2003, 14, 941-949.
21. Wakita, H.; Yoshiwara, H.; Nishiyama, H.; Nagase, H. Total synthesis of optically active m-phenylene pgi2 derivative: Beraprost. Heterocycles 2000, 53, 1085-1110.
22. Takeuchi, K.; Kohn, T.J.; Mais, D.E.; True, T.A.; Wyss, V.L.; Jakubowski, J.A. Development of dual-acting agents for thromboxane receptor antagonism and thromboxane synthase inhibition. 2. Design, synthesis, and evaluation of a novel series of phenyl oxazole derivatives. Bioorg. Med. Chem. Lett. 1998, 8, 1943-1948.
23. Baker, S.R.; Clissold, D.W.; McKillop, A. Synthesis of leukotriene a4 methyl ester from D-glucose. Tetrahedron Lett. 1988, 29, 991-994.
24. Stumpp, M.C.; Schmidt, R.R. Synthesis of moenocinol. Tetrahedron 1986, 42, 5941-5948.
25. Dess, D.B.; Martin, J.C. A useful 12-i-5 triacetoxyperiodinane (the dess-martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-i-5 species. J. Am. Chem. Soc. 1991, 113, 7277-7287.
26. Boeckman, R.K., Jr.; Shao, P.; Mullins, J.J. The dess-martin periodinane: 1,1,1-triacetoxy-1,1- dihydro-1,2-benziodoxol-3(1H)-one. Org. Synth. 2000, 77, 141-152.
27. Commeiras, L.; Parrain, J.-L. Concise enantioselective synthesis of furocaulerpin. Tetrahedron: Asymmetry 2004, 15, 509-517.
28. Corey, E.J.; Bakshi, R.K.; Shibata, S. Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications. J. Am. Chem. Soc. 1987, 109, 5551-5553.
29. Corey, E.J.; Helal, C.J. Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: A new paradigm for enantioselective catalysis and a powerful new synthetic method. Angew. Chem. Int. Ed. 1998, 37, 1986-2012.
30. Meyer, M.P. Nonbonding interactions and stereoselection in the corey-bakshi-shibata reduction. Org. Lett. 2009, 11, 4338-4341.
31. Corey, E.J.; Roberts, B.E. Total synthesis of dysidiolide. J. Am. Chem. Soc. 1997, 119, 12425-12431.
32. Jones, T.K.; Mohan, J.J.; Xavier, L.C.; Blacklock, T.J.; Mathre, D.J.; Sohar, P.; Jones, E.T.T.; Reamer, R.A.; Roberts, F.E.; Grabowski, E.J.J. An asymmetric synthesis of mk-0417. Observations on oxazaborolidine-catalyzed reductions. J. Org. Chem. 1991, 56, 763-769.
33. Corey, E.J.; Bakshi, R.K.; Shibata, S.; Chen, C.P.; Singh, V.K. A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses. J. Am. Chem. Soc. 1987, 109, 7925-7926.
34. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. High-field ft nmr application of mosher's method. The absolute configurations of marine terpenoids. J. Am. Chem. Soc. 1991, 113, 4092-4096.
35. Dale, J.A.; Mosher, H.S. Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J. Am. Chem. Soc. 1973, 95, 512-519.
36. de la Torre, M.C.; Garcia, I.; Sierra, M.A. An approach to furolabdanes and their photooxidation derivatives from r-(+)-sclareolide. J. Nat. Prod. 2002, 65, 661-668.
37. Seco, J.M.; Quinoa, E.; Riguera, R. The assignment of absolute configuration by NMR. Chem. Rev. (Washington, DC, USA) 2004, 104, 17-117.
38. Seco, J.M.; Quinoa, E.; Riguera, R. 9-anthrylmethoxyacetic acid esterification shifts-correlation with the absolute stereochemistry of secondary alcohols. Tetrahedron 1999, 55, 569-584.
39. Ohtani, I.I.; Hotta, K.; Ichikawa, Y.; Isobe, M. Application of modified mosher's method to α-aromatic secondary alcohols. Exception of the rule and conformational analyses. Chem. Lett. 1995, 513-514, doi:10.1246/cl.1995.513.
40. Kernan, M.R.; Faulkner, D.J. Regioselective oxidation of 3-alkylfurans to 3-alkyl-4-hydroxybutenolides. J. Org. Chem. 1988, 53, 2773-2776.
41. Sinhababu, A.K.; Borchardt, R.T. General method for the synthesis of phthalaldehydic acids and phthalides from O-bromobenzaldehydes via ortho-lithiated aminoalkoxides. J. Org. Chem. 1983, 48, 2356-2360.
42. Miranda, P.O.; Padron, J.M.; Padron, J.I.; Villar, J.; Martin, V.S. Prins-type synthesis and sar study of cytotoxic alkyl chloro dihydropyrans. ChemMedChem 2006, 1, 323-329.