Zooxanthellactone, a novel γ-lactone-type oxylipine from dinoflagellates of Symbiodinium sp.: Structure, distribution, and biological activity

Bioscience, Biotechnology and Biochemistry

Volumn 68, Issue 4, 2004, Pages 848-852

  Onodera, Ken Ichi ^a   Fukatsu, Takuya ^a   Kawai, Nozomi ^a   Yoshioka, Yukio ^b   Okamoto, Tetsuji ^b   Nakamura, Hideshi ^a   Ojika, Makoto ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Cytotoxic; Dinoflagellate; Oxylipine; Symbiodinium; Zooxanthellactone

Indexed keywords

DOCOSAHEXAENOIC ACID; LACTONE;

ANIMAL; ARTICLE; CELL DEATH; CHEMICAL STRUCTURE; CHEMISTRY; DINOFLAGELLATE; DRUG EFFECT; HUMAN; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TUMOR CELL LINE;

ANIMALS; CELL DEATH; CELL LINE, TUMOR; DINOFLAGELLIDA; DOCOSAHEXAENOIC ACIDS; HUMANS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

DINOPHYCEAE; SYMBIODINIUM; SYMBIODINIUM SP.;

EID: 4544219985     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.68.848     Document Type: Article

References (18)

1. Rowan, R., and Powers, D. A., A molecular genetic classification of zooxanthellae and the evolution of animal-algal symbioses. Science, 251, 1348-1351 (1991).
2. Murata, M., and Yasumoto, T., The structure elucidation and biological activities of high molecular weight algal toxins: maitotoxin, prymnesins and zooxanthellatoxins. Nat. Prod. Rep., 17, 293-314 (2000).
3. Uemura, D., Bioactive polyethers. In "Bioorganic Marine Chemistry" Vol. 4, ed. Scheuer, P. J., Springer-Verlag, Berlin, pp. 1-29 (1991).
4. Shimizu, Y., Microalgal metabolites. Chem. Rev., 93, 1685-1698 (1993).
5. Nakamura, H., Asari, T., Ohizumi, Y., Kobayashi, J., Yamasu, T., and Murai, A., Isolation of zooxanthellatoxins, novel vasoconstrictive substances from the zooxanthella Symbiodinium sp. Toxicon, 31, 371-376 (1993).
6. Onodera, K., Nakamura, H., Oba, Y., and Ojika, M., Zooxanthellamide A, a novel polyhydroxy metabolite from a marine dinoflagellate of Symbiodinium sp. Tetrahedron, 59, 1067-1071 (2003).
7. Fabricant, R. N., De Larco, J. E., and Todaro, G., Nerve growth factor receptors on human melanoma cells in culture. Proc. Natl. Acad. Sci. USA, 74, 565-569 (1977).
8. Miyauchi, S., Moroyama, T., Kyoizumi, S., Asakawa, J., Okamoto, T., and Takada, K., Malignant tumor cell lines produce intereukin-1 like factor. In Vitro Cell. Dev. Biol., 24, 753-758 (1988).
9. Myoken, Y., Myoken, Y., Okamoto, T., Kan, M., Sato, J. D., and Takada, K., Release of fibroblast growth factor-1 by human squamous cell carcinoma correlates with autocrine cell growth. In Vitro Cell. Dev. Biol. Anim., 30A, 790-795 (1994).
10. Michimukai, E., Kitamura, N., Zhang, Y., Wang, H., Hiraishi, Y., Sumi, K., Hayashido, Y., Toratani, S., Okamoto, T., and Takada, K., Mutations in the human homologue of the Drosophila segment polarity gene patched in oral squamous cell carcinoma cell lines. In Vitro Cell. Dev. Biol. Anim., 37, 459-464 (2001).
11. Sato, J. D., Kawamoto, T., and Okamoto, T., Cholesterol requirement of P3-X63-Ag8 and X63-Ag8.653 mouse myeloma cells for growth in vitro. J. Exp. Med., 165, 1761-1766 (1987).
12. Zhang, Y., Wang, H., Toratani, S., Sato, J. D., Kan, M., McKeehan, W. L., and Okamoto, T., Growth inhibition by keratinocyte growth factor receptor of human salivary adenocarcinoma cells through induction of differentiation and apoptosis. Proc. Natl. Acad. Sci. USA, 98, 11336-11340 (2001).
13. Wenkert, E., Buckwalter, B. L., Burfitt, I. R., Gasic, M. J., Gottlieb, H. E., Hagaman, E. W., Schell, F. M., and Wovkulich, P. M., In "Topics in Carbon-13 NMR Spectroscopy" Vol. 2, ed. Levy, G. C., Wiley Interscience, New York, pp. 81-121 (1976).
14. Utaka, M., Watabu, H., and Takeda, A., Asymmetric reduction of the prochiral carbonyl group of aliphatic γ-and δ-keto acids by use of fermenting bakers' yeast. J. Org. Chem., 52, 4363-4368 (1987).
15. Papina, M., Meziane, T., and van Woesik, R., Symbiotic zooxanthellae provide the host-coral Montipora digitata with polyunsaturated fatty acids. Comp. Biochem. Physiol. B, 135, 533-537 (2003).
16. Mansour, M. P., Volkman, J. K., Jackson, A. E., and Blackburn, S. I., The fatty acid and sterol composition of five marine dinoflagellates. J. Phycol., 35, 710-720 (1999).
17. Zhukova, N. V., and Titlyanov, E. A., Fatty acid variations in symbiotic dinoflagellates from Okinawan corals. Phytochemistry, 62, 191-195 (2003).
18. Baillie, B. K., Belda-Baillie, C. A., and Maruyama, T., Conspecificity and Indo-Pacific distribution of Symbiodinium genotypes (Dinophyceae) from giant clams. J. Phycol., 36, 1153-1161 (2000).