Novel lipoxygenase inhibitors, tetrapetalone B, C, and D from Streptomyces sp.
Three novel lipoxygenase inhibitors, tetrapetalone B (2, C(28)H(35)NO(9)), C (3, C(26)H(34)NO(8)), and D (4, C(28)H(36)NO(10)), were isolated from a culture broth of Streptomyces sp. USF-4727 that produced a lipoxygenase inhibitor tetrapetalone A (1) simultaneously. Each chemical structure was revealed by spectroscopic evidence, this suggests that these three compounds are structurally related to 1. They had a tetracyclic skeleton and a beta-D-rhodinosyl moiety. Tetrapetalone B, C, and D inhibited soybean lipoxygenase with IC(50): 320, 360, and 340 microM respectively.
Komoda
Toshikazu
T
Laboratory of Applied Microbiology, School of Food and Nutritional Sciences, University of Shizuoka, Yada, Japan.
Kishi
Madoka
M
Abe
Naoki
N
Sugiyama
Yasumasa
Y
Hirota
Akira
A
D003978:Diazomethane / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007536:Isomerism; D008084:Lipoxygenase / Q000378:metabolism; D016859:Lipoxygenase Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation / Q000187:drug effects; D015394:Molecular Structure; D013025:Glycine max / Q000201:enzymology; D013302:Streptomyces / Q000737:chemistry*
D006027:Glycosides; D006576:Heterocyclic Compounds, 4 or More Rings; D016859:Lipoxygenase Inhibitors; C494870:tetrapetalone B; C494871:tetrapetalone C; C494872:tetrapetalone D; D003978:Diazomethane; D008084:Lipoxygenase