Four new chloro-eremophilane sesquiterpenes from an antarctic deep-sea derived fungus, Penicillium sp. PR19N-1

Marine Drugs

Volumn 11, Issue 4, 2013, Pages 1399-1408

  Wu, Guangwei ^a   Lin, Aiqun ^a   Gu, Qianqun ^a   Zhu, Tianjiao ^a   Li, Dehai ^a  

^a OCEAN UNIVERSITY OF CHINA   (China)

Author keywords

Antarctic deep sea derived fungus; Chlorinated eremophilane sesquiterpene; Penicillium sp.

Indexed keywords

1 CHLORO 3BETA ACETOXY 7 HYDROXYTRINOREREMOPHIL 1,6,9 TRIEN 8 ONE; EREMOFORTINE C; EREMOPHILANE DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; NUCLEOTIDE SEQUENCE; PENICILLIUM; PROTON NUCLEAR MAGNETIC RESONANCE;

FUNGI; PENICILLIUM SP.;

EID: 84877004452     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11041399     Document Type: Article

References (24)

1. Pettit, R.K. Culturability and secondary metabolite diversity of extreme microbes: Expanding contribution of deep sea and deep-sea vent microbes to natural product discovery. Mar. Biotechnol. 2011, 13, 1-11.
2. Thornburg, C.C.; Zabriskie, T.M.; McPhail, K.L. Deep-sea hydrothermal vents: Potential hot spots for natural products discovery? J. Nat. Prod. 2010, 73, 489-499.
3. Kellenberger, E.; Hofmann, A.; Quinn, J.R. Similar interactions of natural products with biosynthetic enzymes and therapeutic targets could explain why nature produces such a large proportion of existing drugs. Nat. Prod. Rep. 2011, 28, 1483-1492.
4. Fenical, W.; Jensen, P.R. Developing a new resource for drug discovery: Marine actinomycete bacteria. Nat. Chem. Biol. 2006, 2, 666-673.
5. Li, D.H.; Wang, F.P.; Xiao, X.; Fang, Y.C.; Zhu, T.J.; Gu, Q.Q.; Zhu, W.M. Trisorbicillinone A, a novel sorbicillin trimer, from a deep sea fungus, Phialocephala sp. FL30r. Tetrahedron Lett. 2007, 48, 5235-5238.
6. Du, L.; Li, D.H.; Zhu, T.J.; Cai, S.X.; Wang, F.P.; Xiao, X.; Gu, Q.Q. New alkaloids and diterpenes from a deep ocean sediment derived fungus Penicillium sp. Tetrahedron 2009, 65, 1033-1039.
7. Zhou, L.N.; Zhu, T.J.; Cai, S.X.; Gu, Q.Q.; Li, D.H. Three new indole-containing diketopiperazine alkaloids from a deep-ocean sediment derived fungus Penicillium griseofulvum. Helv. Chim. Acta 2010, 93, 1758-1763.
8. Skropeta, D. Deep-sea natural products. Nat. Prod. Rep. 2008, 25, 1131-1166.
9. Moreau, S.; Cacan, M. Eremofortin C, a new metabolite obtained from Penicillium roqueforti cultures and from biotransformation of PR toxin. J. Org. Chem. 1977, 42, 2632-2633.
10. Moreau, S.; Biguet, J. Structures et stereochimie des sesquiterpenes de Penicillium roqueforti PR toxine et eremofortines A, B, C, D, E. Tetrahedron 1980, 36, 2989-2997.
11. Watanabe, N.; Fujita, A.; Ban, N.; Yagi, A.; Etoh, H.; Ina, K. Bipolal: Anti-microalgal compound isolated as a candidate for marine antifouling produced by Bipolaris sp. F5206. J. Nat. Prod. 1995, 58, 463-466.
12. Guerriero, A.; Cuomo, V.; Vanzanella, F.; Pietra, F. A novel glyceryl ester (glyceryl dendryphiellate A), a trinor-eremophilane (dendryphiellin A1), and eremophilanes (dendryphiellin E1 and E2) from the marine deutermycete Dendryphiella salina (Sutherland) Pugh et Nicot. Helv. Chim. Acta 1990, 73, 2090-2096.
13. Nunes, F.M.; Oliveira, M.C.F.; Arriaga, Â.M.C.; Lemos, T.L.G.; Andrade-Neto, M.; Mattos, M.C.; Mafezoli, J.; Viana, F.M.P.; Ferreira, V.M.; Rodrigues-Filhod, E.; et al. A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae). J. Braz. Chem. Soc. 2008, 19, 478-482.
14. Guerriero, A.; D'Ambrosio, M.; Cuomo, V.; Vanzanella, F.; Pietra, F. Dendryphiellin A, the first fungal trinor-eremophilane. Isolation from the marine deuteromycete Dendryphiella salina (Sutherland) Pugh et Nicot. Helv. Chim. Acta 1989, 71, 57-61.
15. McDonald, L.A.; Barbieri, L.R.; Bernan, V.S.; Janso, J.; Lassota, P.; Carter, G.T. 07H239-A, a new cytotoxic eremophilane sesquiterpene from the marine-dedived Xylariaceous fungus LL-07H239. J. Nat. Prod . 2004, 67, 1565-1567.
16. Yamada, T.; Doi, M.; Miura, A.; Harada, W.; Hiramura, M.; Minoura, K.; Tanaka, R.; Numata, A. Absolute stereostructures of cell-adhesion inhibitors, peribysins A, E, F and G, produced by a sea hare-derived Periconia sp. J. Antibiot. 2005, 58, 185-191.
17. Sørensen, D.; Raditsis, A.; Trimble, L.A.; Blackwell, B.A.; Sumarah, M.W.; Miller, J.D. Isolation and structure elucidation by LC-MS-SPE/NMR; PR toxin- and cuspidatol-related eremophilane sesquiterpenes from Penicillium roqueforti. J. Nat. Prod. 2007, 70, 121-123.
18. Huang, Y.F.; Qiao, L.; Lv, A.L.; Pei, Y.H.; Tian, L. Eremophilane sesquiterpenes from the marine fungus Penicillium sp. BL-27-2. Chin. Chem. Lett. 2008, 19, 562-564.
19. Shishova, E.T.; Costamzo, L.D.; Cane, D.E.; Christianson, D.W. X-ray crystal structure of aristolochene synthase from Aspergillus terreus and evolution of templates for the cyclization of farnesyl diphosphate. Biochemistry 2007, 46, 1941-1951.
20. Agger, S.; Lopez-Gallego, F.; Schmidt-Dannert, C. Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus. Mol. Microbiol. 2009, 72, 1181-1195.
21. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
22. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Jonathan, T. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Nat. Cancer Inst . 1990, 82, 1107-1112.
23. Fraga, B.M. Natural sesquiterpenoids. Nat. Prod. Rep. 2012, 29, 1334-1366.
24. Fraga, B.M. Natural sesquiterpenoids. Nat. Prod. Rep. 2011, 28, 1580-1610.