Salinisporamycin, a novel metabolite from Salinispora arenicola. [corrected].
A new rifamycin antibiotic, salinisporamycin (1), has been isolated from a culture of a marine actinomycete. The producing organism was identified as Salinispora arenicola [corrected] on the basis of the 16S rRNA sequence. High-resolution FAB-MS established the molecular formula of 1 as C(33)H(43)NO(9). The planar structure of 1 was elucidated by NMR spectral analysis including COSY, heteronuclear single quantum coherence and heteronuclear multiple bond correlation. The relative stereochemistry of 1 was determined on the basis of rotating frame nuclear Overhauser effect spectroscopy. In addition, the solvatochromic behavior of 1 was investigated by measuring the UV spectra. This compound inhibited the growth of A549 cells, the human lung adenocarcinoma cell line, with an IC(50) value of 3 microg ml(-1), and also showed antimicrobial activity.
Matsuda
Satoru
S
Bioorganic Chemistry Group, Marine Biotechnology Institute Co. Ltd., Kamaishi, Iwate, Japan. s-matsuda@amail.plala.or.jp
Adachi
Kyoko
K
Matsuo
Yoshihide
Y
Nukina
Manabu
M
Shizuri
Yoshikazu
Y
D000890:Anti-Infective Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D019015:Geologic Sediments / Q000382:microbiology; D006801:Humans; D008848:Micromonosporaceae / Q000378:metabolism*; D012294:Rifamycins / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D014871:Water Microbiology
D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D012294:Rifamycins; C544882:salinisporamycin