References of 5-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3,11,14-trihydroxy-10,
13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,
17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
Title: Gamabufotalin
CAS Registry Number: 465-11-2
CAS Name: (3b,5b,11a)-3,11,14-Trihydroxybufa-20,22-dienolide
Synonyms: gamabufogenin; gamabufagin
Molecular Formula: C24H34O5
Molecular Weight: 402.52
Percent Composition: C 71.61%, H 8.51%, O 19.87%
Literature References: One of the genins found in the venom of a Japanese toad (gama;
Bufo vulgaris formosus). Isoln and structure: Kotake,
Ann. 465, 11 (1928); Wieland, Vocke,
Ann. 481, 215 (1930); Chen
et al., J. Pharmacol. Exp. Ther. 49, 26 (1933); Kondo, Ohno,
J. Pharm. Soc. Jpn. 59, 186 (1939); Jensen,
J. Am. Chem. Soc. 59, 767 (1937); Kuno Meyer,
Helv. Chim. Acta 32, 1599 (1949). Also found in Ch'an-Su, A Chinese drug prepared from Chinese toads (
Bufo asiaticus = Bufo gargarizans Cantor): Ruckstuhl, Meyer,
Helv. Chim. Acta 40, 1270 (1957).
Properties: Bitter, solvated prisms from alcohol + ether, mp 254°; when dry dec 262-263°. [a]D18 +1.26° (c = 0.793 in methanol). Produces numbness of the tongue. uv max about 300 nm. Very sparingly sol in chloroform, acetone, water. Somewhat more sol in methanol.
Melting point: mp 254°
Optical Rotation: [a]D18 +1.26° (c = 0.793 in methanol)
Absorption maximum: uv max about 300 nm