Guanidine Compounds and Phosphagens

Natural Guanidino Compounds

“…Asterubine has no effect on blood pressnre; the effect on blood glucose is a short initial hyperglycaemia, followed by areturn to normal levels (Ackermann and Heinsen, 1935). first isolated from the marine polychaete Arenicola marina 1954a) and subsequently characterized in other marine worms (Thoai and Robin, 1969), sponges Ackermann and Pant, 1961;Bergquist and Hartmann, 1969) and a sea anemone (Makisumi, 1961). Taurocyamine was also found in various biological fluids and tissues of mammals, e.g.…”

“…The urinary excretion of glycocyamine is strongly increased in hyperargininemia (Terheggen et al, 1972). Apart from mammals, glycocyamine has also been reported in various marine invertebrates (Thoai and Robin, 1954a); this compound is particularly abundant in the muscles of certain marine worms which utilize phosphoglycocyamine as the muscular phosphagen (Thoai et a1., 1953b;Thoai and Robin, 1969).…”

“…Octopine (30) (derived from arginine and pyruvic acid) was first isolated from Octopus muscle (Morizawa, 1927) and also found in a large number of molluscs (Mayeda, 1936;Ackermann and Mohr, 1937;Moore and Wilson, 1937;Irvin and Wilson, 1939;Regnouf and Thoai, 1970;Gäde and Zebe, 1973), in yeast cultures (Obata and Iimori, 1952), in sipunculid and nemertean worms (Thoai and Robin, 1969;Robin, 1964a), in sea anemones (Zamit and Newsholme, 1976;Ellington, 1980), and in crown gall tumors induced by Agrobacterium tumefaciens (Menage and Morel, 1964). Homooctopine (31) (derived from homoarginine and pyruvic acid) was isolated from crown gall tumor tissues cultured on media containing homoarginine (Petit and Morel, 1966).…”

“…However, the proposed structure has not been unequivo-The bio10gical role 01' the diguanidino compounds is unclear. They do not participate in the formation 01' a new phosphagen, even in the leech in which hirudonine is the principal guanidino compound present in the muscle, but in which, exceptionally, no phosphagen could be detected (Thoai and Robin, 1969). Arcaine, audouine and hirudonine were shown to promote in vitro the po1ymerization of actin as efficient1y as the corresponding diamines (Oriol-Audit, 1978); they could therefore playapart in the control of growth processes.…”

“…However, it increases in muscular dystrophy as a result of the inabi1ity of the muscle to retain creatine (Menne and Beckrnann, 1955;Hur1ey and Wil1iams, 1955). Creatine was further characterized in a number of protochordates and of invertebrates (Meyerhof, 1928;Greenwald, 1946;Roche et al, 1951;Thoai and Robin, 1969). In these animals, creatine is present either as a permanent constituent of muscle, or as a seasona1 constituent, e.g.…”