Structure determination and total synthesis of a novel antibacterial substance, AB0022A, produced by a cellular slime mold.
A novel antibacterial substance, AB0022A, was isolated from the cellular slime mold Dictyostelium purpureum K1001. It inhibited the growth of Gram-positive bacteria, and its MICs ranged from 0.39 to 50 microg/ml. Because AB0022A was a highly substituted aromatic compound, we could not determine its structure based on only its physico-chemical and spectral data. We therefore used a dehalogenated derivative from AB0022A and deduced that its structure was 1,9-dihydroxy-3,7-dimethoxy-2-hexanoyl-4,6,8-trichlorodibenzofuran . To confirm this structure, we synthesized the compound having the deduced structure. The synthetic compound was identical to naturally occurring AB0022A.
Sawada
T
T
Central Research Laboratories, Kyorin Pharmaceutical Co. Ltd., Nogi-machi, Tochigi, Japan.
Aono
M
M
Asakawa
S
S
Ito
A
A
Awano
K
K
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D016837:Dictyosteliida / Q000737:chemistry* / Q000378:metabolism; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D013210:Staphylococcus / Q000187:drug effects
C417143:1,9-dihydroxy-3,7-dimethoxy-2-hexanoyl-4,6,8-trichlorodibenzofuran; D000900:Anti-Bacterial Agents; D005663:Furans