Ophiodilactones A and B, cytotoxic tetrameric phenylpropanoids, from the ophiuroid Ophiocoma scolopendrina

Journal of Organic Chemistry

Volumn 74, Issue 11, 2009, Pages 4396-4399

  Ueoka, Reiko ^a   Fujita, Toshihiko ^b   Matsunaga, Shigeki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b DEPARTMENT OF BOTANY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON SKELETON; CHEMICAL EQUATIONS; CYTOTOXIC; CYTOTOXIC ACTIVITIES; LEUKEMIA CELLS; PHENYLPROPANOIDS; SPECTROSCOPIC DATA;

CHEMICAL REACTIONS;

CYTOTOXIC AGENT; OPHIODILACTONE A; OPHIODILACTONE B; PHENYLPROPANOID; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CYTOTOXICITY; ECHINODERM; LEUKEMIA P 388; MOUSE; NONHUMAN; OPHIOCOMA SCOLOPENDRINA; SPECTROSCOPY; STRUCTURE ANALYSIS;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZENE DERIVATIVES; CELL DEATH; CELL LINE, TUMOR; LACTONES; LEUKEMIA; MICE; MOLECULAR STRUCTURE; SPECTRUM ANALYSIS; STARFISH;

EID: 66249119014     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9003844     Document Type: Article

References (31)

1. (a) Oak, T.; Scheibling, R. E. Coral Reefs 2006, 25, 213-222.
2. (b) Fourgon, D.; Lepoint, G.; Eeckhaut, I. J. Mar. Biol. Ass. U.K. 2006, 86, 1443-1447.
3. (c) Clark, A. M.; Rowe, F. W. E. In Monograph of Shallow-Water Indo-West Pacific Echinoderms; Trustees of the British Museum (Natural History): London, 1971.
4. (a) Roccatagliata, A. J.; Maier, M. S.; Seldes, A. M.; Pujol, C. A.; Damonte, E. B. J. Nat. Prod. 1996, 59, 887-889.
5. (b) Roccatagliata, A. J.; Maier, M. S.; Seldes, A. M. J. Nat. Prod. 1998, 61, 370-374.
6. (c) Levina, E. V.; Andriyaschenko, P. V.; Kalinovsky, A. I.; Stonik, V. A. J. Nat. Prod. 1998, 61, 1423-1426.
7. (d) Ivanchina, N. V.; Kicha, A. A.; Kalinovsky, A. I.; Dmitrenok, P. S.; Stonik, V. A. J. Nat. Prod. 2003, 66, 298-301.
8. (e) Inagaki, M.; Shibata, M.; Isobe, R.; Higuchi, R. Chem. Pharm. Bull. 2001, 49, 1521-1525.
9. (f) Sato, D.; Ando, Y.; Tsujimoto, R.; Kawasaki, K. Lipids 2001, 36, 1371-1375.
10. Kupchan, S. M.; Britton, R. W.; Ziegler, M. F.; Sigel, C. W. J. Org. Chem. 1973, 38, 178-179.
11. Newmark, R. A.; Hill, J. R. Org. Magn. Reson. 1980, 13, 40-44.
12. (a) Beecham, A. F. Tetrahedron Lett. 1968, 2355-2360.
13. (b) Novák, J. J. K. Collect. Czech. Chem. Commun. 1974, 39, 869-882.
14. (a) Kato, A.; Hashimoto, Y.; Kidokoro, M. J. Nat. Prod. 1979, 42, 159-162.
15. (b) Sefkow, M. J. Org. Chem. 2001, 66, 2343-2349.
16. (c) Inagaki, I.; Hisada, S.; Nishibe, S. Chem. Pharm. Bull. 1972, 20, 2710-2718.
17. (a) Mason, C. P.; Edwards, K. R.; Carlson, R. E.; Pignatello, J.; Gleason, F. K.; Wood, J. M. Science 1982, 215, 400-402.
18. (b) Pignatello, J. J.; Porwoll, J.; Carlson, R. E.; Xavier, A.; Gleason, F. K.; Wood, J. M. J. Org. Chem. 1983, 48, 4035-4038.
19. (c) Kiriyama, N.; Nitta, K.; Sakaguchi, Y.; Taguchi, Y.; Yamamoto, Y. Chem. Pharm. Bull. 1977, 25, 2593-2601.
20. (d) Nitta, K.; Fujita, N.; Yoshimura, T.; Arai, K.; Yamamoto, Y. Chem. Pharm. Bull. 1983, 31, 1528-1533.
21. (e) Braña, M. F.; García, M. L.; López, B.; de Pascual-Teresa, B.; Ramos, A.; Pozuelo, J. M.; Domínguez, M. T. Org. Biomol. Chem. 2004, 2, 1864-1871.
22. (f) Miao, S.; Andersen, R. J. J. Org. Chem. 1991, 56, 6275-6280.
23. (g) Yang, X.; Shimizu, Y.; Steiner, J. R.; Clardy, J. Tetrahedron Lett. 1993, 34, 761-764.
24. (h) Smith, C. J.; Hettich, R. L.; Jompa, J.; Tahir, A.; Buchanan, M. V.; Ireland, C. M. J. Org. Chem. 1998, 63, 4147-4150.
25. (i) Tsui, W. Y.; Williams, G. A.; Brown, G. D. Phytochemistry 1996, 43, 1083-1085.
26. (j) Lee, S. C.; Brown, G. D. J. Nat. Prod. 1998, 61, 29-33.
27. (k) Lee, S. C.; Williams, G. A.; Brown, G. D. Phytochemistry 1999, 52, 537-540.
28. (l) Wong, H. F.; Williams, G. A.; Brown, G. D. Phytochemistry 2002, 60, 425-429.
29. (m) Brown, G. D.; Wong, H. F.; Hutchinson, N.; Lee, S. C.; Chan, B. K. K. Phytochem. Rev. 2004, 3, 381-400.
30. (o) Ward, R. S. Nat. Prod. Rep. 1999, 16, 75-96.
31. Wang, W.; Hong, J.; Lee, C. O.; Cho, H. Y.; Shin, S.; Jung, J. H. Nat. Prod. Sci. 2004, 10, 253-261.