Table of Contents Author Guidelines Submit a Manuscript
BioMed Research International
Volume 2017, Article ID 7871459, 7 pages
https://doi.org/10.1155/2017/7871459
Research Article

Punctaporonins N–S, New Caryophyllene Sesquiterpenoids from Cytospora sp.

1State Key Laboratory of Toxicology & Medical Countermeasures, Beijing Institute of Pharmacology & Toxicology, Beijing 100850, China
2Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing 100081, China
3State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, China

Correspondence should be addressed to Yongsheng Che; nc.ca.mi@syehc

Received 5 May 2017; Revised 27 July 2017; Accepted 22 August 2017; Published 24 October 2017

Academic Editor: Jane Hanrahan

Copyright © 2017 Yan Li et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. T. Henkel, R. M. Brunne, H. Müller, and F. Reichel, “Statistical investigation into the structural complementarity of natural products and synthetic compounds,” Angewandte Chemie International Edition, vol. 38, no. 5, pp. 643–647, 1999. View at Publisher · View at Google Scholar · View at Scopus
  2. J. B. Gloer, “Antiinsectan Natural Products from Fungal Sclerotia,” Accounts of Chemical Research, vol. 28, no. 8, pp. 343–350, 1995. View at Publisher · View at Google Scholar · View at Scopus
  3. J. Meinwald and T. Eisner, “Chemical ecology in retrospect and prospect,” Proceedings of the National Acadamy of Sciences of the United States of America, vol. 105, no. 12, pp. 4539-4540, 2008. View at Publisher · View at Google Scholar · View at Scopus
  4. J. B. Gloer, “The mycota. A comprehensive treatise on fungi as experimental systems for basic applied research. Volume IV: environmental and microbial relationships,” in The Mycota IV: Environmental and Microbial Relationships, D. T. Wicklow and B. Soderstrom, Eds., pp. 249–268, Springer, Berlin, Germany, 1997. View at Google Scholar
  5. H. Guo, H. Hu, S. Liu, X. Liu, Y. Zhou, and Y. Che, “Bioactive p-terphenyl derivatives from a Cordyceps-colonizing isolate of Gliocladium sp,” Journal of Natural Products, vol. 70, no. 9, pp. 1519–1521, 2007. View at Publisher · View at Google Scholar · View at Scopus
  6. Y. Zhang, S. Liu, Y. Che, and X. Liu, “Epicoccins A-D, epipolythiodioxopiperazines from a Cordyceps-colonizing isolate of Epicoccum nigrum,” Journal of Natural Products, vol. 70, no. 9, pp. 1522–1525, 2007. View at Publisher · View at Google Scholar · View at Scopus
  7. H. Guo, B. Sun, H. Gao et al., “Trichocladinols A-C, cytotoxic metabolites from a Covdyceps-colomzing ascomycete Trichocladium opacum,” European Journal of Organic Chemistry, no. 32, pp. 5525–5530, 2009. View at Publisher · View at Google Scholar · View at Scopus
  8. Y. Zhang, S. Liu, H. Liu, X. Liu, and Y. Che, “Cycloaspeptides F and G, cyclic pentapeptides from a Cordyceps-colonizing isolate of Isaria farinosa,” Journal of Natural Products, vol. 72, no. 7, pp. 1364–1367, 2009. View at Publisher · View at Google Scholar · View at Scopus
  9. Y. Chen, H. Guo, Z. Du, X.-Z. Liu, Y. Che, and X. Ye, “Ecology-based screen identifies new metabolites from a Cordyceps-colonizing fungus as cancer cell proliferation inhibitors and apoptosis inducers,” Cell Proliferation, vol. 42, no. 6, pp. 838–847, 2009. View at Publisher · View at Google Scholar · View at Scopus
  10. C. Ma, Y. Li, S.-B. Niu, H. Zhang, X.-Z. Liu, and Y. Che, “N-hydroxypyridones, phenylhydrazones, and a quinazolinone from isaria farinosa,” Journal of Natural Products, vol. 74, no. 1, pp. 32–37, 2011. View at Publisher · View at Google Scholar · View at Scopus
  11. J. Lin, S. Liu, B. Sun et al., “Polyketides from the ascomycete fungus Leptosphaeria sp.,” Journal of Natural Products, vol. 73, no. 5, pp. 905–910, 2010. View at Publisher · View at Google Scholar · View at Scopus
  12. X. Zou, S. Niu, J. Ren, E. Li, X. Liu, and Y. Che, “Verrucamides A-D, antibacterial cyclopeptides from Myrothecium verrucaria,” Journal of Natural Products, vol. 74, no. 5, pp. 1111–1116, 2011. View at Publisher · View at Google Scholar · View at Scopus
  13. J. Lin, X. Chen, X. Cai et al., “Isolation and characterization of aphidicolin and chlamydosporol derivatives from Tolypocladium inflatum,” Journal of Natural Products, vol. 74, no. 8, pp. 1798–1804, 2011. View at Publisher · View at Google Scholar · View at Scopus
  14. Y. Li, S. Niu, B. Sun, S. Liu, X. Liu, and Y. Che, “Cytosporolides A-C, antimicrobial meroterpenoids with a unique peroxylactone skeleton from cytospora sp.,” Organic Letters, vol. 12, no. 14, pp. 3144–3147, 2010. View at Publisher · View at Google Scholar · View at Scopus
  15. J. T. J. Spence and J. H. George, “Structural reassignment of cytosporolides A-C via Biomimetic synthetic studies and reinterpretation of NMR Data,” Organic Letters, vol. 13, no. 19, pp. 5318–5321, 2011. View at Publisher · View at Google Scholar · View at Scopus
  16. Y. Li, C. Li, C. Cui, X. Liu, and Y. Che, “Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.,” Natural Products and Bioprospecting, vol. 2, no. 2, pp. 70–75, 2012. View at Publisher · View at Google Scholar
  17. S. T. Deyrup, D. C. Swenson, J. B. Gloer, and D. T. Wicklow, “Caryophyllene sesquiterpenoids from a fungicolous isolate of Pestalotiopsis disseminata,” Journal of Natural Products, vol. 69, no. 4, pp. 608–611, 2006. View at Publisher · View at Google Scholar · View at Scopus
  18. Crystallographic data for compound 1a have been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC 778343). Copies of the data can be obtained, free of charge, on application to the director, CCDC 12 Union Road, Cambridge CB2 1EZ, UK, 2017.
  19. Sheldrick G. M., “Crystal structure refinement with SHELXL,” Acta Crystallographica, vol. C71, pp. 3–8, 2015. View at Google Scholar
  20. G. M. Sheldrick, SADABS, program for empirical absorption correction of area detector data, University of Göttingen, Göttingen, Germany, 1999.
  21. Y. Li, D. Ye, Z. Shao, C. Cui, and Y. Che, “A sterol and spiroditerpenoids from a Penicillium sp. isolated from a deep sea sediment sample,” Marine Drugs, vol. 10, no. 2, pp. 497–508, 2012. View at Publisher · View at Google Scholar · View at Scopus
  22. N. Zhang, Y. Chen, R. Jiang et al., “PARP and RIP-1 are required for autophagy induced by 11- deoxyverticillin A, which precedes caspase-dependent apoptosis,” Autophagy, vol. 7, no. 6, pp. 598–612, 2011. View at Publisher · View at Google Scholar · View at Scopus