UCH9, a new antitumor antibiotic produced by Streptomyces. II. Structure elucidation of UCH9 by mass and NMR spectroscopy.
The structure of UCH9, which is a novel antitumor agent, was determined by spectroscopic methods. UCH9 consists of an aglycone and five 2,6-dideoxy sugars (three D-olivoses, one 4-O-methyl-D-olivose and one D-oliose). Four of the five sugars are sequentially connected through a beta 1-->3 linkage (olivose-1-->3-4-O-methyl-olivose-1-->3-oliose-1-->3-+ ++olivose). On the basis of the results of spectroscopic analysis, it was found that UCH9 belongs to the aureolic acid family of antibiotics. The structure of UCH9 is unique in that mono- and tetrasaccharide moieties, and a long hydrophobic side chain (sec-butyl group) are attached to the aglycone, while di- and trisaccharide moieties and a methyl or a hydrogen are attached in the case of the known aureolic acid analogs. It is known that aureolic acid analogs from a dimer in the presence of Mg2+. NMR, FAB-MS and atomic absorption analysis revealed that UCH9 isolated from Streptomyces also forms a dimer, containing one equivalent molar Mg2+.
Katahira
R
R
Tokyo Research Laboratories, Kyowa Hakko Kogyo Co., Ltd., Japan.
Uosaki
Y
Y
Ogawa
H
H
Yamashita
Y
Y
Nakano
H
H
Yoshida
M
M
D000903:Antibiotics, Antineoplastic / Q000737:chemistry*; D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008926:Plicamycin / Q000031:analogs & derivatives* / Q000737:chemistry; D013302:Streptomyces / Q000378:metabolism
D000903:Antibiotics, Antineoplastic; C110708:UCH 9; D008926:Plicamycin