Production of Prostaglandins by the Marine Alga, Gracilaria verrucosa Ichiro NAKAJIMA*1, Kazuhiko SUZAKI*2, and Kenkichi OBA*3 *1 Life Science Researc
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1 Production of Prostaglandins by the Marine Alga, Gracilaria verrucosa Ichiro NAKAJIMA*1, Kazuhiko SUZAKI*2, and Kenkichi OBA*3 *1 Life Science Research Center, Lion Corporation (100, Tajima, Odawara-shi, Kanagawa-ken ) *2 Pharmaceutical Affairs Department, Lion Corporation (1-3-7, Honjo, Sumida-ku, Tokyo ) *3 Research & Development Headquarters, Lion Corporation ( , Hirai, Edogawa-ku, Tokyo ) Abstract: Marine red alga Gracilaria verrucosa, a material commonly used to make agar, contains no prostaglandins(pg) in nature. But through physical stimulation, this alga was found to produce remarkable amounts of PG using enzymes and substrates in itself. PG was produced in the amount of approximately 2g/kg in dry matter with PGE2 at 90%. PG composition was determined mainly by polyunsaturated fatty acids present in the alga and could be controlled through use of a suitable precursor for each PG. The data for unialgal culture of G. verrucosa confirmed that this alga produces PG. Various species of other algae belonging to the genus Gracilaria were found to produce PG in small amounts. Key words: Gracilaria verrucosa, prostaglandin, culture, biosynthesis
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3 Fig. 2 Prostaglandins obtained from Gracilaria verrucosa. -: HPLC elution pattern of the extracts monitored by absorbance at 196nm. œ : Contraction of rat stomach strip with the eluate. Table 1 Yields of prostaglandins produced by G. verrucosa. Table 2 Fatty acid composition in G. verrucosa. The number before the colon means chain length and the number after the colon degree of unsaturation. Omega(ƒÖ) shows the first double bond position from the methyl terminal. DHL: dihomo -ƒá-linolenic acid, AA: arachidonic acid, EPA: eicosapentaenoic acid.
4 Table 3 Prostaglandin composition after the additional reaction with a precursor. DHL: dihomo-ć-linolenic acid, AA: arachidonic acid, EPA: eicosapentaenoic acid, ND: not detected. Table 4 Yields of prostaglandins produced and fatty acid contents of prostaglandin precursors in cultured G. verrucosa. DHL: dihomo-ć-linolenic acid, AA: arachidonic acid, EPA: eicosapentaenoic acid, ND: not detected. Fig. 3 Seasonal variation of fatty acid contents and PGE2 productivity. AA: arachidonic acid, EPA: eicosapentaenoic acid.
5 Table 5 Prostaglandin productivity of other algae belonging to genus Gracilaria. DHL: dihomo-ć-linolenic acid, AA: arachidonic acid, EPA: eicosapentaenoic acid, ND: not detected.
6 2) N. Fusetani, K. Hashimoto, Bull. Jpn. Soc. Sci. Fish., 50, 465 (1984). 3) R.P. Gregson, J.F. Marwood, R.J. Quinn, Tetrahedron Lett., 46, 4505 (1979). 4) W.S. Powell, Prostaglandins, 20, 947 (1980). 6) J.H. Gaddum, Br. J. Pharmacol., 8, 321 (1953). 7) J. Folch, M. Lees, G.A. Sloane-Stanley, J. Biol. Chem., 226, 497 (1957). 8) L. Provasoli, gcultures and Collections of Algae h (Proceedings of the U.S.-Japan Conference held at Hakone, Sep , 1966, ed. by A. Watanabe, A. Hattori), Japan. Soc. Plant Physiol., Tokyo (1966) p ) J.E. Pike, F.H. Lincoln, W.P. Schneider, J. Org. Chem., 34, 3552 (1969). 11) T. Yasumoto, D. Yasumura, M. Yotsu, T. Michishita, A. Endo, Y. Kotaki, Agric. Biol. Chem., 50, 793 (1986). 12) T. Noguchi, J.K. Jeon, O. Arakawa, H. Sugita, Y. Deguchi, Y. Shida, K. Hashimoto, J. Biochem., 99, 311 (1986). 13) M. Kodama, T. Ogata, S. Sato, Agric. Biol. Chem., 52, 1075 (1988). 14) J. Zhang, B. Xia, Oceanologia et Limnologia Sinica, 16, 175 (1985). 15) H. Yamamoto, J. Sasaki, Bull. Fac. Fish. Hokkaido Univ., 39 (1), 1 (1988). 16) S. Araki, T. Sakurai, T. Oohusa, M. Kayama, K. Nisizawa, Hydrobiologia, 204/205, 513 (1990). 17) D.F. Reingold, P. Needleman, Trends in Pharmacological Science, September, 359 (1980). 18) D.B. Largo, P.T. Bacolod, M.A.V. Cusi, C.A. Orosco, M. Ohno, gscientific Survey of Marine Algae and their Resources in the Philippine Islands h, ed. by I. Umezaki (1989) p ) E.J. Corey, W.N. Washburn, J.C. Chen, J. Amer. Chem. Soc., 95, 2054 (1973). 16
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