New Bioactive Sulfated Alkenes from the Sea Cucumber Apostichopus japonicus
Ming-Ping La
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorCui Li
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorLing Li
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorPeng Sun
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorHua Tang
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorBao-Shu Liu
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorWei Gong
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorHua Han
College of Animal Sciences, Zhejiang University, 268 Kai-Xuan Road, Hangzhou 310029, P. R. China
Search for more papers by this authorCorresponding Author
Yang-Hua Yi
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)Search for more papers by this authorCorresponding Author
Wen Zhang
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)Search for more papers by this authorMing-Ping La
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorCui Li
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorLing Li
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorPeng Sun
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorHua Tang
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorBao-Shu Liu
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorWei Gong
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Search for more papers by this authorHua Han
College of Animal Sciences, Zhejiang University, 268 Kai-Xuan Road, Hangzhou 310029, P. R. China
Search for more papers by this authorCorresponding Author
Yang-Hua Yi
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)Search for more papers by this authorCorresponding Author
Wen Zhang
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China (phone/fax: +86-21-81871257)Search for more papers by this authorAbstract
Two new alkene sulfates, (5Z)-dec-5-en-1-yl sulfate (4) and (3E)-dec-3-en-1-yl sulfate (5), together with three known sulfated alkanes, 2,6-dimethylheptyl sulfate (1), octyl sulfate (2), and decyl sulfate (3), were isolated from the sea cucumber Apostichopus japonicus. The structures of the new compounds 4 and 5 were elucidated by spectroscopic analysis, including 1H-, 13C-, and 2D-NMR, ESI-MS, and HR-ESI-MS. Compounds 2 and 3 were isolated from natural sources for the first time. In preliminary bioassays in vitro, compounds 4 and 5 showed antibacterial, antifungal, and cytotoxic activities.
Graphical Abstract
References
- 1 J. A. Findlay, Z.-Q. He, L. A. Calhoun, J. Nat. Prod. 1990, 53, 1015.
- 2 J. A. Findlay, N. Yayli, L. A. Calhoun, J. Nat. Prod. 1991, 54, 302.
- 3a A. Crispino, A. De Giulio, S. De Rosa, S. De Stefano, A. Milone, N. Zavodnik, J. Nat. Prod. 1994, 57, 1575;
- 3b S. Tsukamoto, H. Kato, H. Hirota, N. Fusetani, J. Nat. Prod. 1994, 57, 1606;
- 3c A. Aiello, E. Fattorusso, M. Menna, Tetrahedron 1997, 53, 5877;
- 3d A. Aiello, E. Fattorusso, M. Menna, R. Carnuccio, T. Iuvone, Tetrahedron 1997, 53, 11489;
- 3e A. Aiello, S. Carbonelli, G. Esposito, E. Fattorusso, T. Iuvone, M. Menna, J. Nat. Prod. 2000, 63, 1590;
- 3f A. Aiello, S. Carbonelli, E. Fattorusso, T. Iuvone, M. Menna, J. Nat. Prod. 2001, 64, 219;
- 3g M. Fujita, Y. Nakao, S. Matsunaga, T. Nishikawa, N. Fusetani, J. Nat. Prod. 2002, 65, 1936.
- 4 M. Diop, A. Samb, V. Costantino, E. Fattorusso, A. Mangoni, J. Nat. Prod. 1996, 59, 271.
- 5 A. J. Roccatagliata, M. S. Maier, A. M. Seldes, S. Zea, C. Duque, J. Nat. Prod. 1997, 60, 285.
- 6 K. Yasumoto, A. Nishigami, F. Kasai, T. Kusumi, T. Ooi, Chem. Pharm. Bull. 2006, 54, 271.
- 7 W. Yuan, Y. Yi, H. Tang, M. Xue, Z. Wang, G. Sun, W. Zhang, B. Liu, L. Li, P. Sun, Chem. Pharm. Bull. 2008, 56, 1207; W.-H. Yuan, Y.-H. Yi, H.-F. Tang, B.-S. Liu, Z.-L. Wang, G.-Q. Sun, W. Zhang, L. Li, P. Sun, Planta Med. 2009, 75, 168; H. Han, W. Zhang, Y.-H. Yi, B.-S. Liu, M.-X. Pan, X.-H. Wang, Chem. Biodiversity 2010, 7, 1764.
- 8 I. Kitagawa, T. Sugawara, I. Yosioka, Chem. Pharm. Bull. 1976, 24, 275; I. Kitagawa, H. Yamanaka, M. Kobayashi, T. Nishino, I. Yosioka, T. Sugawara, Chem. Pharm. Bull. 1978, 26, 3722; I. I. Maltsev, V. A. Stonik, A. I. Kalinovsky, G. B. Elyakov, Comp. Biochem. Physiol., B 1984, 78, 421.
- 9 C. H. Xue, L. F. Yu, P. Dong, J. Xu, Z. J. Li, Y. Xue, Period. Ocean Univ. China 2010, 40, 60.
- 10 M. Karlberg, L. Piculell, L. Huang, Carbohydr. Polym. 2007, 70, 350; J. F. Berret, Colloid Polym. Sci. 2009, 287, 801.
- 11 N. Fusetani, K. Yasumuro, S. Matsunaga, H. Hirota, Tetrahedron Lett. 1989, 30, 6891; F. D. Gunstone, J. Am. Oil Chem. Soc. 1993, 70, 965.
- 12 T. Mosmann, J. Immunol. Methods 1983, 65, 55.