Olivomycin and related antibiotics XXVIII. Monomeric composition of aureolic acid and proof that the antibiotics LA-7017 and mithramycin are identical to it
Summary1. It has been shown that aureolic acid, antibiotic LA-7017, and mithramycin are identical.2. It has been established that aureolic acid is a glycoside of chromomycinone (I) and contains the monosaccharides D-olivose (II), D-oliose (III), and D-mycarose (IV) in a ratio of 3 : 1 : 1.
Aureolic Acid Group of Anti-tumour Antibiotics
SINCE 1953 several antibiotics of similar biological and physico-chemical properties have been described. These are aureolic acid1, aburamycin2, LA-7017 (ref. 3), M5-18903 (ref. 4), chromomycin5, antibiotic 2410 (ref. 6), NSC A-649 (ref. 7), olivomycin8, mithramycin9 and antibiotics 232, 3014, 7193, 11296 (ref. 10) and SK-229 (ref. 11). Two members of this group, olivomycin and chromomycin, were subjected to extensive chemical research which resulted in the isolation and structural elucidation of their components, olivomycins A, B, C, D (ref. 12) and chromomycins A2, A3, A4 (ref. 13). The other members of the group, however, have been only scantily investigated.
METABOLITES OF PATHOGENIC FUNGI: III. THE STRUCTURE OF XANTHOMEGNIN
Xanthomegnin, a pigment isolated from Trichophyton megnini, was shown to be (−) 3,3′-bis-[2-methoxy-5-hydroxy-7-(2-hydroxypropyl)-8-carboxy-l,4-naphthoquinone lactone]. Application of the Hudson–Klyne lactone rule (C. S. Hudson, J. Am. Chem. Soc., 32, 338 (1910); W. Klyne, Chem. Ind. (London), 1198 (1954)) gave results which supported the proposed stereochemistry.