Studies on Active Principles of Tar. VII. Production of Biological Active Substances in Pyrolyses of Amino Acids and Antifungal Constituents in Pyrolysis Products of Tryptophan

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  • タール剤の成分研究(第7報)各種アミノ酸の乾留による生理活性物質の生成およびトリブトファン乾留成績体中の抗糸状菌性物質について

Abstract

Past studies on active principles in tar has shown that active principles were classified into basic and acidic parts, namely pyrolysis of protein-rich sourses like eggs, nonfat soybean, or fish meal mostly produced N-heteroaromatic compounds, while pyrolysis of carbohydrate-rich sources like wood or rice bran produced acidic compounds. These results prompted clarification of pyrosynthetic mechanisms of fomation of these N-heteroaromatic compounds under pyrolytic conditions. A series of amino acids was pyrolyzed and their antifungal activities were tested to find that pyrolysates of aromatic amino acids (tryptophan, phenylalanine, tyrosine), lysine, and arginine, had a potent antifungal activity. Among them the active principles in the pyrolysate of DL-tryptophan were identified as norharman, harman, and 1-ethyl-β-carboline. It was also found that 1-isobutyl-, 1-isopentyl-, and 1-(2-methylbutyl)-β-carboline, which were isolated from egg tar, were formed from the pyrolysis of DL-tryptophan-leucine and DL-tryptophan-isoleucine mixture.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 98 (7), 904-909, 1978

    The Pharmaceutical Society of Japan

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