Title: Chartreusin
CAS Registry Number: 6377-18-0
CAS Name: 10-[[6-Deoxy-2-O-(6-deoxy-3-O-methyl-a-D-galactopyranosyl)-b-D-galactopyranosyl]oxy]-6-hydroxy-1-methylbenzo[h][1]benzopyrano[5,4,3-cde][1]benzopyran-5,12-dione
Additional Names: antibiotic X-465A; lambdamycin
Manufacturers' Codes: NSC-5159
Molecular Formula: C32H32O14
Molecular Weight: 640.59
Percent Composition: C 60.00%, H 5.04%, O 34.97%
Literature References: Antibiotic substance produced by Streptomyces chartreusis from African soil, also by another Streptomyces sp. from North American soil: B. E. Leach et al., J. Am. Chem. Soc. 75, 4011 (1953). Identity with Antibiotic X-465A: J. Berger et al., ibid. 80, 1636 (1958). Structure: L. H. Sternbach et al., ibid. 1639; E. Simonitsch et al., Helv. Chim. Acta 47, 1459 (1964); W. Eisenhuth et al., ibid. 1475. Anticancer activity: J. P. McGovern et al., Cancer Res. 37, 1666 (1977). Synthesis of chartarin, the chartreusin aglycone: T. R. Kelly et al., J. Am. Chem. Soc. 102, 798 (1980); F. M. Hauser, D.W. Combs, J. Org. Chem. 45, 4071 (1980).
Properties: Yellow plates from acetone or methylene chloride + ethanol, mp 184-186°. Weak acid. [a]D25 +132.5° (c = 0.2 in pyridine); [a]D25 -33° (c = 0.3 in glacial acetic acid). uv max: 237, 262, 332, 382, 405, 422 nm. Practically insol in water. Sol in acetone.
Melting point: mp 184-186°
Optical Rotation: [a]D25 +132.5° (c = 0.2 in pyridine); [a]D25 -33° (c = 0.3 in glacial acetic acid)
Absorption maximum: uv max: 237, 262, 332, 382, 405, 422 nm
Derivative Type: Sodium salt
Properties: Gold-colored needles or plates from water. Soly in water: at least 20 mg/ml (pH 9.5). LD50 i.v. in mice: 250 mg/kg (Leach).
Toxicity data: LD50 i.v. in mice: 250 mg/kg (Leach)
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