Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Penidioxolanes A and B, 1,3-Dioxolane Containing Azaphilone Derivatives from Marine-derived Penicillium sp. KCB12C078

  • Kim, Seung Min (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Son, Sangkeun (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim, Jong Won (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Jeon, Eun Soo (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Ko, Sung-Kyun (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Ryoo, In-Ja (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Shin, Kee-Sun (Microbial Resources Center, KRIBB) ;
  • Hirota, Hiroshi (RIKEN-KRIBB Joint Research Unit, Global Research Cluster, RIKEN) ;
  • Takahashi, Shunji (RIKEN-KRIBB Joint Research Unit, Global Research Cluster, RIKEN) ;
  • Osada, Hiroyuki (Chemical Biology Research Group, RIKEN CSRS) ;
  • Jang, Jae-Hyuk (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Ahn, Jong Seog (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology)
  • Received : 2015.06.05
  • Accepted : 2015.06.17
  • Published : 2015.12.31
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Abstract

Two new azaphilone derivatives containing 1,3-dioxolane moiety, penidioxolanes A (1) and B (2), were isolated from marine-derived fungus Penicillium sp. KCB12C078, together with four known compounds (3-6) by chemical investigation. Compounds 1 - 6 were isolated by combination of silica gel, ODS column chromatography and preparative HPLC. Their structures were determined by analysis of spectroscopic data including 1D-, 2D-NMR, and MS techniques. The isolates were evaluated against cancer cell growth inhibition effects and antimicrobial activity.

Keywords

References

  1. Berdy, J. J. Antibiot. 2005, 58, 1-26. https://doi.org/10.1038/ja.2005.1
  2. Fenical, W.; Jensen, P. R. Nat. Chem. Biol. 2006, 2, 666-673. https://doi.org/10.1038/nchembio841
  3. Faulkner, D. J. Nat. Prod. Rep. 1998, 15, 113-158. https://doi.org/10.1039/a815113y
  4. Satpute, S. K.; Banat, I. M.; Dhakephalkar, P. K.; Banpurkar, A. G.; Chopade, B. A. Biotechnol. Adv. 2010, 28, 436-450. https://doi.org/10.1016/j.biotechadv.2010.02.006
  5. Osmanova, N.; Schultze, W.; Ayoub, N. Phytochem. Rev. 2010, 9, 315-342. https://doi.org/10.1007/s11101-010-9171-3
  6. Gao, J. M.; Yang, S. X.; Qin, J. C. Chem. Rev. 2013, 113, 4755-4811. https://doi.org/10.1021/cr300402y
  7. Quang, D. N.; Hashimoto, T.; Fournier, J.; Stadler, M.; Radulovic, N.; Asakawa, Y. Tetrahedron 2005, 61, 1743-1748. https://doi.org/10.1016/j.tet.2004.12.031
  8. Kanokmedhakul, S.; Kanokmedhakul, K.; Nasomjai, P.; Louangsy-souphanh, S.; Soytong, K.; Isobe, M.; Kongsaeree, P.; Prabpai, S.; Suksamrarn, A. J. Nat. Prod. 2006, 69, 891-895. https://doi.org/10.1021/np060051v
  9. Yu, B. Z.; Zhang, G. H.; Du, Z. Z.; Zheng, Y. T.; Xu, J. C.; Luo, X. D. Phytochemistry 2008, 69, 2523-2526. https://doi.org/10.1016/j.phytochem.2008.07.013
  10. Quang, D. N.; Hashimoto, T.; Tanaka, M.; Stadler, M.; Asakawa, Y. Phytochemistry 2004, 65, 469-473. https://doi.org/10.1016/j.phytochem.2003.09.022
  11. Li, J. J.; Shang, X. Y.; Li, L. L.; Liu, M. T.; Zheng, J. Q.;Jin, Z. L. Molecules 2010, 15, 1958-1966. https://doi.org/10.3390/molecules15031958
  12. Dong, J.; Zhou, Y.; Li, R.; Zhou, W.; Li, L.; Zhu, Y.; Huang, R.; Zhang, K. FEMS. Microbiol. Lett. 2006, 264, 65-69. https://doi.org/10.1111/j.1574-6968.2006.00430.x
  13. Yasukawa, K.; Takahashi, M.; Natori, S.; Kawai, K.; Yamazaki, M.; Takeuchi, M.; Takido, M. Oncology 1994, 51, 108-112. https://doi.org/10.1159/000227320
  14. Michael, A. P.; Grace, E. J.; Kotiw, M.; Barrow, R. A. Aust. J. Chem. 2003, 56, 13-15. https://doi.org/10.1071/CH02021
  15. Arai, N.; Shiomi, K.; Tomoda, H.; Tabata, N.; Yang, D. J.; Masuma R.; Kawakubo, T.; Omura, S. J. Antibiot. 1995, 48, 696-702. https://doi.org/10.7164/antibiotics.48.696
  16. Curtin, T. P.; Reilly, J. Biochem. J. 1940, 34, 1419-1421.
  17. Holker, J. S. E.; Ross, W. J.; Staunton J.; Whalley, W. B. J. Chem. Soc. 1962, 4150-4154. https://doi.org/10.1039/jr9620004150
  18. Gray, R. W.; Whalley, W. B. Chem. Commun. 1970, 12, 762.
  19. Yang, D. J.; Tomoda, H.; Tabata, N.; Masuma, R.; Omura, S. J. Antibiot. 1996, 49, 223-229. https://doi.org/10.7164/antibiotics.49.223
  20. Matsuzaki, K.; Tanaka, H.; Omura, S. J. Antibiot. 1995, 48, 708-713. https://doi.org/10.7164/antibiotics.48.708
  21. Arunpanichlert, J.; Rukachaisirikul, V.; Sukpondma, Y.; Phongpaichit, S.; Tewtrakul, S.; Rungjindamai, N.; Sakayaroj, J. Chem. Pharm. Bull. 2010, 58, 1033-1036. https://doi.org/10.1248/cpb.58.1033

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