Nodulisporisteriods A and B, the first 3,4-seco-4-methyl-progesteroids from Nodulisporium sp.

Steroids

Volumn 78, Issue 9, 2013, Pages 896-901

  Zheng, Qi Chang ^a   Chen, Guo Dong ^a   Kong, Ming Zhu ^b   Li, Guo Qiang ^a   Cui, Jia Yu ^a   Li, Xiao Xia ^a   Wu, Zu Yan ^a   Guo, Liang Dong ^c   Cen, Ying Zhou ^a   Zheng, Yi Zhi ^b   Gao, Hao ^a  

^a JINAN UNIVERSITY   (China)

^b SHENZHEN UNIVERSITY   (China)

^c INSTITUTE OF MICROBIOLOGY   (China)

Author keywords

3 4 Seco 4 methyl progesteroid; 4 Methyl progesteroid; Anti Ab42 aggregation activity; Endolichenic fungus; Nodulisporium sp.; Xylariaceae

Indexed keywords

DEMETHOXYVIRIDIN; EPIGALLOCATECHIN GALLATE; INOTERPENE B; NODULISPORISTERIOD A; NODULISPORISTERIOD B; NOOTROPIC AGENT; PROGESTERONE; THIOFLAVINE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; FLUORESCENCE ANALYSIS; FUNGUS; METABOLITE; NODULISPORIUM; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

FUNGI; NODULISPORIUM; XYLARIACEAE;

EID: 84885004271     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2013.05.007     Document Type: Article

References (29)

1. Rochet JC, Lansbury Jr PT. Amyloid fibrillogenesis: themes and variations. Curr Opin Struct Biol 2000;10:60-8. (Pubitemid 30099328)
2. Harper JD, Lansbury Jr PT. Models of amyloid seeding in Alzheimer's disease and scrapie: mechanistic truths and physiological consequences of the timedependent solubility of amyloid proteins. Annu Rev Biochem 1997;66:385-407. (Pubitemid 27274662)
3. Bernstein SL, Dupuis NF, Lazo ND, Wyttenbach T, Condron MM, Bitan G, et al. Amyloid-b protein oligomerization and the importance of tetramers and dodecamers in the aetiology of Alzheimer's disease. Nat Chem 2009;1:326-31.
4. Tsai J, Grutzendler J, Duff K, Gan WB. Fibrillar amyloid deposition leads to local synaptic abnormalities and breakage of neuronal branches. Nat Neruosci 2004;7:1181-3. (Pubitemid 39426234)
5. Mangialasche F, Solomon A, Winblad B, Mecocci P, Kivipelto M. Alzheimer's disease: clinical trials and drug development. Lancet Neurol 2010;9:702-16.
6. Ondeyka JG, Helms GL, Hensens OD, Goetz MA, Zink DL, Tsipouras A, et al. Nodulisporic acid A, a novel and potent insecticide from a Nodulisporium sp. Isolation, structure determination, and chemical transformations. J Am Chem Soc 1997;119:8809-16.
7. Singh SB, Ondeyka JG, Jayasuriya H, Zink DL, Na SN, Dahl-Roshak A, et al. Nodulisporic acids D-F: structure, biological activities, and biogenetic relationships. J Nat Prod 2004;67:1496-506. (Pubitemid 39298617)
8. Kasettrathat C, Ngamrojanavanich N, Wiyakrutta S, Mahidol C. Cytotoxic and antiplasmodial substances from marine-derived fungi, Nodulisporium sp. and CRI247-01. Phytochemistry 2008;69:2621-6.
9. Dai JQ, Krohn K, Draeger S, Schulz B. New naphthalene-chroman coupling products from the endophytic fungus, Nodulisporium sp. from Erica arborea. Eur J Org Chem 2009;10:1564-9.
10. Kamisuki S, Ishimaru C, Onoda K, Kuriyama I, Ida N, Sugawara F, et al. Nodulisporol and nodulisporone, novel specific inhibitors of human DNA polymerase k from a fungus Nodulisporium sp.. Bioorg Med Chem 2007;15:3109-14. (Pubitemid 46484341)
11. Aldridge DC, Turner WB. Demethoxyviridin and demethoxyviridiol: new fungal metabolites. J Chem Soc Perkin Trans 1975;1:943-5.
12. Cole JR, Kirksey JW, Springer JP, Clardy J, Cutler H, Garren KH, et al. Desmethoxyviridiol, a new toxin from Nodulisporium hinnuleum. Phytochemistry 1975;14:1429-32.
13. He JW, Chen GD, Gao H, Yang F, Li XX, Peng T, et al. Heptaketides with antiviral activity from three endolichenic fungal strains Nigrospora sp., Alternaria sp. and Phialophora sp.. Fitoterapia 2012;83:1087-91.
14. Chen GD, Li YJ, Gao H, Chen Y, Li XX, Li J, et al. New azaphilones and chlorinated phenolic glycosides from Chaetomium elatum with Caspase-3 inhibitory activity. Planta Med 2012;78:1683-9.
15. Yang F, Chen GD, Gao H, Li XX, Wu Y, Guo LD, et al. Two new naphthalene derivatives from an endolichenic fungal strain Scopulariopsis sp. J Asian Nat Prod Res 2012;14:1059-63.
16. Hanson JR, O'Leary MA, Wadsworth HJ. Studies in terpenoid biosynthesis, Part 28. The acetate and mevalonate labelling patterns of the steroid, demethoxyviridin. J Chem Soc Perkin Trans 1983;1:867-70.
17. Nakamura S, Iwami J, Matsuda H, Mizuno S, Yoshikawa M. Absolute stereostructures of inoterpenes A-F from sclerotia of Inonotus obliquus. Tetrahedron 2009;65:2443-50.
18. Chakrabortee S, Liu Y, Zhang L, Matthews HR, Zhang H, Pan N, et al. Macromolecular and small-molecule modulation of intracellular Ab42 aggregation and associated toxicity. Biochem J 2012;442:507-15.
19. CCDC 919524. The data for 1 can be obtained free of charge from the Cambridge Crystallograhic Data Centre via. Available from: http://www.ccdc.cam. ac.uk/data-request/cif.
20. Moss GP. Nomenclature of steroids. Pure Apll Chem 1989;61:1783-822.
21. Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, et al. Classification and pharmacology of progestins. Maturitas 2003;46:S7-S16. (Pubitemid 37506058)
22. Gürgey K. An attempt to recognise oil populations and potential source rock types in Paleozoic sub-and Mesozoic-Cenozoic supra-salt strata in the southern margin of the Pre-Caspian Basin, Kazakhstan Republic. Org Geochem 2002;33:723-41. (Pubitemid 34793623)
23. De Rosa S, Milone A, Popov S, Andreev S. Sterol composition of the Black Sea Hydrozoan, Obelia longissima (Pallas 1766). Comp Biochem Physiol B Biochem Mol Biol 1999;123:229-33. (Pubitemid 29259850)
24. Hanson JR. The viridin family of steroidal antibiotics. Nat Prod Rep 1995;12:381-4.
25. Brown GD. The biosynthesis of steroids and triterpenoids. Nat Prod Rep 1998;15:653-96. (Pubitemid 29025682)
26. Baeyer A, Villiger V. Einwirkung des caro'schen reagens auf ketone. Chem Ber 1899;32:3625-33.
27. Baeyer A, Villiger V. Ueber die Einwirkung des Caro'schen Reagens auf Ketone. Chem Ber 1900;33:858-64.
28. Mandel SA, Amit T, Kalfon L, Reznichenko L, Weinreb O, Youdim MB, et al. Cell signaling pathways and iron chelation in the neurorestorative activity of green tea polyphenols: special reference to epigallocatechin gallate (EGCG). J Alzheimers Dis 2008;15:211-22.
29. Wipf P, Halter RJ. Chemistry and biology of wortmannin. Org Biomol Chem 2005;3:2053-61. (Pubitemid 40859876)