Structure of slow-reacting substance of anaphylaxis (SRS-A) |
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Authors: | Haruo Ohnishi Hiroshi Kosuzume Yutaka Kitamura Kazuo Yamaguchi Masahiro Nobuhara Yasuo Suzuki Shoji Yoshida Hisao Tomioka Akira Kumagai |
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Institution: | Tokyo Research Laboratory, Mochida Pharmaceutical Co., Ltd. 1-1-1 Kamiya, Kita-ku, Tokyo, 115, Japan;The Second Department of Internal Medicine, School of Medicine, Chiba University, 1-8-1 Inohana, Chiba-shi, 280, Japan |
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Abstract: | To elucidate the chemical structure of slow-reacting substance of anaphylaxis from rat (SRS-Arat), SRS-Arat were purified by the method of Orange with modification using DEAE-Sephadex A-25 chromatography. Ultraviolet absorption spectrum of purified SRS-Arat indicated the presence of conjugated triene. Arylsulfatase B degradation products and HCl degradation products were subjected to analysis by a gas chromatography and mass spectrometry and a thin layer chromatography. Products obtained by arylsulfatase B catalysis contained 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid. HCl degradation products showed the presence of glycine, glutamic acid and cysteic acid. Furthermore, the analysis of anhydrous hydrazine degradation products of SRS-Arat and of HCl hydrolyzed products of dinitrophenylated SRS-Arat revealed the presence of glycine at C-terminal and glutamic acid at N-terminal. The study of the substrate specificity of arylsulfatase B against various materials including SRS-Arat suggested the presence of sulfone in SRS-Arat. The molecular ion peak of SRS-Arat sodium salt was observed at m/e 680 in field desorption mass spectrum of SRS-Arat.On the basis of these data, we identified the structure of SRS-Arat as γ-glutamyl-4(5-hydroxy-7,9,11,14-eicosatetraenoic acid-6-yl)-4,4-dioxocysteinyl] glycine. |
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Keywords: | Slow-reacting substance of anaphylaxis (SRS-A) Structure Arylsulfatase Field desorption mass spectrometry (FDMS) |
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