Chemistry and tumor cell growth inhibitory activity of 11,20-epoxy-3Z,5(6) E-diene briaranes from the South China Sea gorgonian Dichotella gemmacea

Marine Drugs

Volumn 11, Issue 5, 2013, Pages 1565-1582

  Li, Cui ^a   Jiang, Mei ^a   La, Ming Ping ^a   Li, Tie Jun ^a   Tang, Hua ^a   Sun, Peng ^a   Liu, Bao Shu ^a   Yi, Yang Hua ^a   Liu, Zhiyong ^b   Zhang, Wen ^a  

^a SECOND MILITARY MEDICAL UNIVERSITY   (China)

^b SECOND MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Biological activity; Briarane diterpenoids; Dichotella gemmacea; Gorgonian; Structure activity relationship

Indexed keywords

DICHOTELLIDE C; DICHOTELLIDE F; DICHOTELLIDE I; DITERPENOID; GEMMACOLIDE AA; GEMMACOLIDE AB; GEMMACOLIDE AC; GEMMACOLIDE AD; GEMMACOLIDE AE; GEMMACOLIDE AF; GEMMACOLIDE AG; GEMMACOLIDE AH; GEMMACOLIDE AI; GEMMACOLIDE AJ; GEMMACOLIDE AK; GEMMACOLIDE AL; GEMMACOLIDE AM; GEMMACOLIDE AN; GEMMACOLIDE AO; GEMMACOLIDE AP; GEMMACOLIDE AQ; GEMMACOLIDE AR; GEMMACOLIDE N; JUNCENOLIDE C; JUNCENOLIDE D; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; DICHOTELLA GEMMACEA; DRUG STRUCTURE; GROWTH INHIBITION; IN VITRO STUDY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; TUMOR GROWTH;

GORGONIA;

EID: 84878274301     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11051565     Document Type: Article

References (18)

1. Blunt, J.W.; Copp, B.R.; Keyzers, R.A.; Munro, M.H.G.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2013, 30, 237-323.
2. Berrue, F.; Kerr, R.G. Diterpenes from gorgonian corals. Nat. Prod. Rep. 2009, 26, 681-710.
3. Sung, P.J.; Su, J.H.; Wang, W.H.; Sheu, J.H.; Fang, L.S.; Wu, Y.C.; Chen, Y.H.; Chung, H.M.; Su, Y.D.; Chang, Y.C. Survey of briarane-type diterpenoids - Part IV. Heterocycles 2011, 83, 1241-1258.
4. Zhang, W.; Guo, Y.W.; Gu, Y.C. Secondary metabolites from the South China Sea invertebrates chemistry and biological activity. Curr. Med. Chem. 2006, 13 2041-2090.
5. Sun, J.F.; Han, Z.; Zhou, X.F.; Yang, B.; Lin, X.; Liu, J.; Peng, Y.; Yang, X.W.; Liu, Y.H. Antifouling briarane type diterpenoids from South China Sea gorgonians Dichotella gemmacea. Tetrahedron 2013, 69, 871-880.
6. Liu, T.F.; Lu, X.; Tang, H.; Zhang, M.M.; Wang, P.; Sun, P.; Liu, Z.Y.; Wang, Z.L.; Li, L.; Rui, Y.C.; et al. 3β,5α,6β-Oxigenated sterols from the South China Sea gorgonian Muriceopsis flavida and their tumor cell growth inhibitory activity and apoptosis-inducing function. Steroids 2013, 78, 108-114.
7. Wang, Z.L.; Zhang, H.Y.; Yuan, W.H.; Gong, W.; Tang, H.; Liu, B.S.; Krohn, K.; Yi, Y.H.; Zhang, W. Antifungal nortriterpene and triterpene glycosides from the sea cucumber Apostichopus japonicus Selenka. Food Chem. 2012, 132, 295-300.
8. Sun, P.; Meng, L.Y.; Tang, H.; Liu, B.S.; Li, L.; Yi, Y.H.; Zhang, W. Sinularosides A and B, bioactive 9,11-secosteroidal glycosides from the South China Sea soft coral Sinularia sp. J. Nat. Prod. 2012, 75, 1656-1659.
9. Geng, W.L.; Wang, X.Y.; Kurtán, T.; Mándi, A.; Tang, H.; Schulz, B.; Sun, P.; Zhang, W. Herbarone, a rearranged heptaketide derivative from the sea hare associated fungus Torula herbarum. J. Nat. Prod. 2012, 75, 1828-1832.
10. Li, C.; La, M.P.; Li, L.; Li, X.B.; Tang, H.; Liu, B.S.; Krohn, K.; Sun, P.; Yi, Y.H.; Zhang, W. Bioactive 11,20-epoxy-3,5(16)-diene briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea. J. Nat. Prod. 2011, 74, 1658-1662.
11. Li, C.; La, M.P.; Sun, P.; Kurtán, T.; Mándi, A.; Tang, H.; Liu, B.S.; Yi, Y.H.; Li, L.; Zhang, W. Bioactive (3Z, 5E)-11,20-epoxybriara-3, 5-diene-7,18-olide diterpenoids from the South China Sea gorgonian Dichotella gemmacea. Mar. Drugs 2011, 9, 1403-1418.
12. Li, C.; La, M.P.; Tang, H.; Pan, W.H.; Sun, P.; Yi, Y.H.; Zhang, W. Bioactive briaranes from the South China Sea gorgonian Dichotella gemmacea. Bioorg. Med. Chem. Lett. 2012, 22, 4368-4372.
13. Roe, M.B.; Whittaker, M.; Procter, G. Studies on the synthesis of solenolide F; a Cr(II)-mediated cyclization to form the ten-membered ring. Tetrahedron Lett. 1995, 36, 8103-8106.
14. Balasubramaniam, R.P.; Moss, D.K.; Wyatt, J.K.; Spence, J.D.; Gee, A.; Nantz, M.H. Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes. Tetrahedron 1997, 53, 7429-7444. (Pubitemid 27226744)
15. Rodriguez, A.D.; Ramirez, C.; Cobar, O.M. Briareins C-L, 10 new briarane diterpenoids from the common Caribbean gorgonian Briareum asbestinum. J. Nat. Prod. 1996, 59, 15-22. (Pubitemid 27074375)
16. Iwasaki, J.; Ito, H.; Nakamura, M.; Iguch, K. A synthetic study of briarane-type marine diterpenoid, pachyclavulide B. Tetrahedron Lett. 2006, 47, 1483-1486.
17. Shen, Y.C.; Lin, Y.C.; Ko, C.L.; Wang, L.T. New briaranes from the Taiwanese gorgonian Junceella juncea. J. Nat. Prod. 2003, 66, 302-305.
18. Mosmann, T.J. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.