Rare 1,2'-binaphthyls produced by Nodulisporium hinnuleum Smith (ATCC 36102)

Records of Natural Products

Volumn 5, Issue 4, 2011, Pages 252-260

  Schlingmann, Gerhard ^a   Luckman, Scott ^a   McDonald, Leonard A ^a   Koehn, Frank E ^a  

^a WYETH RESEARCH   (United States)

Author keywords

Binaphthyl; Fungal metabolite; Nodulisporium hinnuleum; Oxygen reactive compounds

Indexed keywords

HINNULIN A; HINNULIN B; HINNULIN C; HINNULIN D; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG PURIFICATION; DRUG STRUCTURE; FERMENTATION; FUNGUS; NODULISPORIUM HINNULEUM; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

FUNGI; NODULISPORIUM;

EID: 79957604753     PISSN: None     EISSN: 13076167     Source Type: Journal    
DOI: None     Document Type: Article

References (14)

1. D.C. Aldridge, W.B. Turner, A.J. Geddes, B. Sheldrick (1975). Demethoxyviridin and demethoxyviridiol, new fungal metabolites, J. Chem. Soc., Perkin Trans. 1, 10, 943-945.
2. R.J. Cole, J.W. Kirksey, J. P. Springer, J. Clardy, H.G. Cutler, K.H. Garren (1975). Desmethoxyviridiol, a new toxin from Nodulisporium hinnuleum, Phytochemistry 14, (5-6), 1429-1432.
3. M.A. O'Leary, J.R. Hansen (1982). Hinnuliquinone, a bisindolyl-2,5-dihydroxybenzoquinone pigment from Nodulisporium hinnuleum, Tetrahedron Letters 23, (17), 1855-1856.
4. M.A. O'Leary, J.R. Hansen, B.L.Yeoh (1984). The structure and biosynthesis of hinnuliquinone, a pigment from Nodulisporium hinnuleum, J. Chem. Soc., Perkin Trans. 1, 3, 567-569.
5. S.B. Singh, J.G. Ondeyka, N. Tsipouras, C. Ruby, V. Sardana, M. Schulman, M. Sanchez, F. Pelaez, M. W. Stahlhut, S. Munshi, D.B. Olsen, R.B. Lingham (2004). Hinnuliquinone, a C2-symmetric dimeric non-peptide fungal metabolite inhibitor of HIV-1 protease, Biochem.Biophys. Res. Comm. 324, (1), 108-113.
6. S. Croux, M.T. Maurette, M. Hocquaux, A. Ananides, A.M. Braun, E. Oliveros (1990). Kinetic parameters of the reactivity of dihydroxynaphthalenes with singlet oxygen, New J. Chem. 14, 161-167.
7. M.C. Foti, E.R. Johnson, M.R. Vinqvist, J.S. Wright, L.R.C. Barclay, K. U. Ingold (2002). Naphthalene Diols: A new class of antioxidants. Intramolecular hydrogen bonding in catechols, naphthalene diols, and their aryloxyl radicals, J. Org. Chem. 67, (15), 5190-5196.
8. [8] M. Flueraru, A. Chichirau, L.L. Chepelev, W.G. Willmore, T. Durst, M. Charron, L.R.C. Barclay, J.S. Wright(2005) Cytotoxicity and cytoprotective activity in naphthalenediols depends on their tendency to form naphthoquinones, Free Radical Biol. Med. 39, (10), 1368-1377.
9. M. Flueraru, R. So, W.G. Willmore, M.O. Poulter, T. Durst, M. Charron, J.S. Wright (2006). Cytotoxicity and cytoprotective activity of Naphthalenediols in rat cortical neurons, Chem. Res. Toxicol. 19, (9), 1221-1227.
10. G. Schlingmann, S. Matile, N. Berova, K. Nakanishi, G.T. Carter (1996). Absolute stereochemistry of the diepoxins, Tetrahedron 1996, 52, (2), 435-446.
11. J. Dai, K. Krohn, U. Floerke, S. Draeger, B. Schulz, A. Kiss-Szikszai, S. Antus, T. Kurtan, T. van Ree (2006). Metabolites from the endophytic fungus Nodulisporium sp. from Juniperus cedre, Eur. J. Org. Chem. 15, 3498-3506.
12. B. Bodo, R.G. Tih, D. Davoust, H. Jacquemin (1983). Hypoxylone, a naphthyl-naphthoquinone pigment from the fungus Hypoxylon sclerophaeum, Phytochemistry 22, (11), 2579-2581.
13. T. Hashimoto, S. Tahara, S. Takaoka, M. Tori, Y. Asakawa (1994). Structures of a novel binaphthyl and three novel benzophenone derivatives with plant-growth inhibitory activity from the fungus Daldinia concentric, Chem.Pharm. Bull. 42, (7), 1528-30.
14. M. Kanda, M. Furui, Y. Abe, M. Shimada (1998). Binaphthalene derivatives, manufacture of their lead compound, and their uses as anti-Helicobacter pylori agents, etc. Japanese Patent: JP 10168009 A 19980623 Heisei. (CAN 129:117830).