Abstract
Combining different chromatography systems, unusual nonprotein amino acids were isolated and unequivocally identified from a small amount (less than 100 g fresh weight) ofAmanita gymnopus fruit body. Without obtaining crystals of these amino acids, on the basis of1H-NMR determination, high resolution mass spectrometry, chlorine analysis and oxidation with L-amino acid oxidase, one of them proved to be a new chloroamino acid, (2S)-2-amino-5-chloro-4-hydroxy-5-hexenoic acid (G2). The other three were (2S)-2-amino-5-hexenoic acid (G1), (2S)-2-amino-4,5-hexadienoic acid (G3) and (2S)-2-amino-5-hexynoic acid (G4). Amino acid (G1) was also encountered for the first time in natural products. Amino acid (G3) has been reported from several kinds of fungi belonging toAmanita, subgenusLepidella. The occurrence of amino acid (G4) was already reported fromCortinarius claricolor.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
Aoyagi, Y. and Sugahara, T. 1985. 2(S)-Amino-5-hexynoic acid, an antimetabolite fromCortinarius claricolor var.tenuipes. Phytochemistry24: 1835–1836.
Bas, C. 1969. Morphology and subdivision ofAmanita and a monograph of its sectionLepidella. Persoonia5: 285–579.
Bas, C. and Hatanaka, S. I. 1984. Persoonia12: 321–325.
Black, D. K. and Landor, S. R. 1968. Allenes. Part XVII. The synthesis of allenic amino-acids from allenic bromides and diethyl formylaminomalonate. J. Chem. Soc. (C) 283–287.
Chilton, W. S. and Tsou, G. 1972. A chloro amino acid fromAmanita solitaria. Phytochemistry11: 2853–2857.
Chilton, W. S. and Tsou, G. 1975. The unsaturated norleucines ofAmanita solitaria. Chemical and pharmacological studies. Lloydia36: 169–193.
Chilton, W. S., Tsou, G. and Benedict, R. G. 1968. A naturally occurring allenic amino acid. Tetrahedron Lett.: 6283–6284.
Corner, E. J. H. and Bas, C. 1962. The genus Amanita in Singapore and Malaya. Persoonia2: 241–304.
Hatanaka, S. I. 1992. Amino acids from mushroom. Progress in the Chemistry of Organic Natural Products59: 1–144.
Hatanaka, S. I. and Kawakami, K. 1980. Isolation and identification ofl-2-amino-4,5-hexadienoic acid fromAmanita neoovoidea Hongo. Sci. Pap. Coll. Gen. Educ. Univ. Tokyo30: 147–150.
Hatanaka, S. I., Niimura, Y. and Takishima, K. 1985. Non-protein amino acids of unsaturated norleucine-type inAmanita pseudoporphyria. Trans. Mycol. Soc. Japan26: 61–68.
Hongo, T. 1974. Notulae Mycologicae (13). Mem. Shiga Univ.24: 44–51.
Moriguchi, K., Hara, Y. and Hatanaka, S. I. 1987. Antibacterial activity ofl-2-amino-4-chloro-4-pentenoic acid isolated fromAmanita pseudoporphyria. J. Antibiot.:40: 904–906.
Murakami, N., Furukawa, J., Okuda, S. and Hatanaka, S. I. 1985. Stereochemistry of 2-aminopimelic acid in three species ofAsplenium. Phytochemistry24: 2491–2294.
Ohta, T., Nakajima, S., Hatanaka, S. I., Yamamoto, M., Shimmen, Y., Nishimura, S., Yamaizumi, Z. and Nozoe, S. 1987. A chlorohydrin amino acid fromAmanita abrupta. Phytochemistry26: 565–566.
Ohta, T., Nakajima, S., Sato, Z., Aoki, T., Hatanaka, S. I. and Nozoe, S. 1986. Cyclopropylalanine, an antifungal amino acid of the mushroomAmanita virgineoides Bas. Chemistry Letters: 511–512.
Singer, R. 1986. “The Agaricales in modern taxonomy, 4th ed.,” Koeltz Sci. Books, Koenigstein. 981 p.
Yamaura, Y., Fukuhara, M., Takabatake, E., Ito, N. and Hashimoto, T. 1986. Hepatotoxic action of a poisonous mushroom,Amanita abrupta, in mice and its toxic component. Toxicology38: 161–173.
Author information
Authors and Affiliations
Additional information
Part 23 in the series “Biochemical studies of nitrogen compounds in fungi.” Part 22, Hatanaka, S. I. et al. 1985. Trans. Mycol. Soc. Japan26: 61–68.
About this article
Cite this article
Hatanaka, SI., Furukawa, J., Aoki, T. et al. (2S)-2-Amino-5-chloro-4-hydroxy-5-hexenoic acid, a new chloroamino acid, and related compounds fromAmanita gymnopus . Mycoscience 35, 391–394 (1994). https://doi.org/10.1007/BF02268510
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02268510