Tetrapetalone A, a Novel Lipoxygense Inhibitor from Streptomyces sp

• Published in: Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2004-01, Vol.68 (1), p.104-111
• Main Authors: KOMODA, Toshikazu, YOSHIDA, Kayo, ABE, Naoki, SUGIYAMA, Yasumasa, IMACHI, Misako, HIROTA, Hiroshi, KOSHINO, Hiroyuki, HIROTA, Akira
• Format: Article
• Language: English
• Subjects: Biological and medical sciences; Fundamental and applied biological sciences. Psychology; soybean lipoxygenase inhibitor; Streptomyces
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.68.104

A simple new assay was designed for lipoxygenase inhibitors. This assay was used to find the novel lipoxygenase inhibitor, tetrapetalone A (1). Tetrapetalone A (1), C 26 H 33 NO 7 , was isolated from Streptomyces sp. USF-4727 strain. Its planar structure was determined by spectroscopic evidence and by methylating with diazomethane to show the presence of a novel tetracyclic skeleton and a β-D-rhodinosyl moiety. The stereochemistry of 1 was investigated by the coupling constant in the 1 H-NMR spectrum, NOE correlations, modified Mosher's method and derivation. We have reported the structural elucidation of 1 in our previous paper. However, further investigation gave another structure for 1, which is described in this paper. Tetrapetalone A showed similar inhibitory activity against soybean lipoxygenase to the two well-known lipoxygenase inhibitors, kojic acid and NDGA, while methylated tetrapetalone A (2) showed little inhibitory activity, even at a concentration of 1 mM.