Chermesins A-D: Meroterpenoids with a Drimane-Type Spirosesquiterpene Skeleton from the Marine Algal-Derived Endophytic Fungus Penicillium chermesinum EN-480

Journal of Natural Products

Volumn 79, Issue 4, 2016, Pages 806-811

  Liu, Hui ^a,b   Li, Xiao Ming ^a   Liu, Yang ^a,b   Zhang, Peng ^a,b   Wang, Jia Ning ^a,b   Wang, Bin Gui ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B; ANTIINFECTIVE AGENT; CHERMESIN A; CHERMESIN B; CHERMESIN C; CHERMESIN D; CHLORAMPHENICOL; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG; DRIMANE; SESQUITERPENE; SPIRO COMPOUND;

AEROMONAS HYDROPHILA; ALTERNARIA BRASSICAE; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTEMIA; ARTEMIA SALINA; ARTICLE; BOTRYOSPHAERIA BERENGERIANA; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG STRUCTURE; EDWARDSIELLA TARDA; ENDOPHYTIC FUNGUS; ESCHERICHIA COLI; FUNGUS CULTURE; FUSARIUM OXYSPORUM; GAEUMANNOMYCES GRAMINIS; GLOMERELLA CINGULATA; HETERONUCLEAR MULTIPLE BOND CORRELATION; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PENICILLIUM; PENICILLIUM CHERMESINUM; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; ULTRAVIOLET SPECTROSCOPY; VIBRIO ALGINOLYTICUS; VIBRIO HARVEYI; VIBRIO PARAHAEMOLYTICUS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ISOLATION AND PURIFICATION; MARINE BIOLOGY; MICROBIAL SENSITIVITY TEST; NUCLEAR MAGNETIC RESONANCE;

CRYSTALLOGRAPHY, X-RAY; MARINE BIOLOGY; MICROBIAL SENSITIVITY TESTS; MICROCOCCUS LUTEUS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PENICILLIUM; SESQUITERPENES; SPIRO COMPOUNDS;

EID: 84967139333     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.5b00893     Document Type: Article

References (20)

1. Gerwick, W. H.; Fenner, A. M. Microb. Ecol. 2013, 65, 800-806 10.1007/s00248-012-0169-9
2. Blunt, J. W.; Copp, B. R.; Keyzers, R. A.; Munro, M. H. G.; Prinsep, M. R. Nat. Prod. Rep. 2015, 32, 116-211 10.1039/C4NP00144C
3. Zhang, P.; Mandi, A.; Li, X. M.; Du, F. Y.; Wang, J. N.; Li, X.; Kurtan, T.; Wang, B. G. Org. Lett. 2014, 16, 4834-4837 10.1021/ol502329k
4. Zhang, P.; Li, X. M.; Li, X.; Wang, B. G. Phytochem. Lett. 2015, 12, 182-185 10.1016/j.phytol.2015.03.017
5. Zhang, P.; Li, X. M.; Wang, J. N.; Li, X.; Wang, B. G. Chin. Chem. Lett. 2015, 26, 313-316 10.1016/j.cclet.2014.11.020
6. Li, X.; Li, X. M.; Xu, G. M.; Li, C. S.; Wang, B. G. Phytochem. Lett. 2014, 7, 120-123 10.1016/j.phytol.2013.11.008
7. Wang, S.; Li, X. M.; Teuscher, F.; Li, D. L.; Diesel, A.; Ebel, R.; Proksch, P.; Wang, B. G. J. Nat. Prod. 2006, 69, 1622-1625 10.1021/np060248n
8. Kaise, H.; Shinohara, M.; Miyazaki, W.; Izawa, T.; Nakano, Y.; Sugawara, M.; Sugiura, K.; Sasaki, K. J. Chem. Soc., Chem. Commun. 1979, 726-727 10.1039/c39790000726
9. Ayer, W. A.; Miao, S. Can. J. Chem. 1993, 71, 487-493 10.1139/v93-069
10. Sakai, K.; Watanabe, K.; Masuda, K.; Tsuji, M.; Hasumi, K.; Endo, A. J. Antibiot. 1994, 48, 447-456 10.7164/antibiotics.48.447
11. Kaneto, R.; Dobashi, K.; Kojima, I.; Sakai, K.; Shibamoto, N.; Yoshioka, T.; Nishida, H.; Okamoto, R.; Akagawa, H.; Mizuno, S. J. Antibiot. 1994, 48, 727-730 10.7164/antibiotics.47.727
12. Miyako, K.; Hirocultural, K.; Jun, U.; Shozo, F.; Tsuyoshi, K.; Yasuo, K. Biosci., Biotechnol., Biochem. 1997, 61, 2153-2155 10.1271/bbb.61.2153
13. Lam, Y. K. T.; Wichmann, C. F.; Meinz, M. S.; Guariglia, L.; Giacobbe, R. A.; Mochales, S.; Kong, L.; Honeycutt, S. S.; Zink, D.; Bills, G. F.; Huang, L.; Burg, R. W.; Monaghan, R. L.; Jackson, R.; Reid, G.; Maguire, J. J.; Mcknight, A. T.; Ragan, C. I. J. Antibiot. 1992, 45, 1397-1403 10.7164/antibiotics.45.1397
14. Chan, J. A.; Freyer, A. J.; Carte, B. K.; Hemiing, M. E.; Hofmann, G. A.; Mattern, M. R.; Mentzer, M. A.; Westley, J. W. J. Nat. Prod. 1994, 57, 1543-1548 10.1021/np50113a011
15. Crystallographic data of compounds 1-4 have been deposited in the Cambridge Crystallographic Data Centre as CCDC 1412760, 1412761, 1412762, and 1412644, respectively. The data can be obtained free of charge via http://www.ccdc.cam.ac.uk/data-request/cif (or from the CCDC, 12 Union Road, Cambridge CB21EZ, U.K.; fax: +44-1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
16. Sheldrick, G. M. SADABS, Software for Empirical Absorption Correction; University of Göttingen: Germany, 1996.
17. Sheldrick, G. M. SHELXTL, Structure Determination Software Programs; Bruker Analytical X-ray System Inc.: Madison, WI, 1997.
18. Sheldrick, G. M. SHELXL-97 and SHELXS-97, Program for X-ray Crystal Structure Solution and Refinement; University of Göttingen: Germany, 1997.
19. Pierce, C. G.; Uppuluri, P.; Tristan, A. R.; Wormley, F. L., Jr.; Mowat, E.; Ramage, G.; Lopez-Ribot, J. L. Nat. Protoc. 2008, 3, 1494-1500 10.1038/nprot.2008.141
20. Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobsen, L. B.; Nichols, D. E.; McLaughlin, J. L. Planta Med. 1982, 45, 31-34 10.1055/s-2007-971236