Ushikulide C (1), a new immunosuppressant, was isolated from the culture broth of Streptomyces sp. IUK-102. The structure of 1 is a new 22-membered macrolide that is related to ushikulides A (2) and B (3). The immunosuppressive activity of 1 on murine splenocyte proliferation in vitro was comparable with those of 2 and 3.
DreyfussM., HarriE., HoffmannH., KobelH., PacheW., TscherterH. (1976) Cyclosporin A and C. New metabolites from Trichoderma polysporum (Linx ex Pers.) Rifai. European Journal of Applied Microbiology, 3, 125–133.
2.
KinoT., HatanakaH., HashimotoM., NishiyamaM., GotoT., OkuharaM., KohsakaM., AokiH., ImanakaH. (1987) FK-506, a new novel immunosuppressant isolated from a Streptomyces. I. Fermentation, isolation, and physic-chemical and biological characteristics. Journal of Antibiotics, 40, 1249–1255.
3.
SchreiberS.L., CrabtreeG.R. (1992) The mechanism of action of cyclosporine A and FK506. Immunology Today, 13, 136–142.
4.
TakahashiK., YoshiharaT., KurosawaK. (2005) Ushikulides A and B, immunosuppressants produced by a strain of Streptomyces sp. Journal of Antibiotics, 58, 420–424.
5.
TrostB.M., O'BoyleB.M. (2008) Exploiting orthogonally reactive functionality: synthesis and stereochemical assignment of (-)-ushikulide A. Journal of American Chemical Society, 130, 16190–16192.
6.
TrostB.M., O'BoyleB.M., HundD. (2009) Total synthesis and stereochemical assignment of (-)-ushikulide A. Journal of American Chemical Society, 131, 15061–15074.
7.
KurosawaK., TakahashiK., TsudaE. (2001) SNF4435C and D, novel immunosuppressants produced by a strain of Streptomyces spectabilis. I. Taxonomy, fermentation, isolation and biological activities. Journal of Antibiotics, 54, 541–547.
