Reveromycin A, B, C, D

Structure
A: NPEdia
B: NPEdia
C: NPEdia
D: NPEdia
Reveromycin
Producing organism
Streptomyces reveromyceticus SN593
Biological activity
antifungal activity, eukariotic protein synthesis inhibition
Abstract
New antibiotics named reveromycins A, B, C and D were isolated as inhibitors of mitogenic activity induced by epidermal growth factor (EGF) in a mouse epidermal keratinocyte. Reveromycins were produced by a soil actinomycete (strain SN-593) which belongs to the genus Streptomyces.
References
isolation and structural determination
  • Osada H, Koshino H, Isono K, Takahashi H, Kawanishi G.: Reveromycin A, a new antibiotic which inhibits the mitogenic activity of epidermal growth factor.
    J Antibiot, 44(2): 259-261 (1991) PMID: 2010365
  • Takahashi H, Osada H, Koshino H, Kudo T, Amano S, Shimizu S, Yoshihama M, Isono K.: Reveromycins, new inhibitors of eukaryotic cell growth. I. Producing organism, fermentation, isolation and physico-chemical properties.
    J Antibiot, 45(9): 1409-1413 (1992) PMID: 1429225
  • Koshino H, Takahashi H, Osada H, Isono K.: Reveromycins, new inhibitors of eukaryotic cell growth. III. Structures of reveromycins A, B, C and D.
    J Antibiot, 45(9): 1420-1427 (1992) PMID: 1429227
  • biological activity
  • Takahashi H, Osada H, Koshino H, Sasaki M, Onose R, Nakakoshi M, Yoshihama M, Isono K.: Reveromycins, new inhibitors of eukaryotic cell growth. II. Biological activities.
    J Antibiot, 45(9): 1414-1419 (1992) PMID: 1429226
  • Takahashi H, Yamashita Y, Takaoka H, Nakamura J, Yoshihama M, Osada H.: Inhibitory action of reveromycin A on TGF-alpha-dependent growth of ovarian carcinoma BG-1 in vitro and in vivo.
    Oncol Res, 9(1): 7-11 (1997) PMID: 9112255
  • Tanaka Y, Ishikawa F, Osada H, Imajoh-Ohmi S, Uchida T, Kakiuchi T.: Reveromycin A inhibits antigen receptor-mediated antigen presentation by B lymphoma cells via its effect on intracellular trafficking of the antigen.
    J Antibiot, 55(10): 904-913 (2002) PMID: 12523824
  • Miyamoto Y, Machida K, Mizunuma M, Emoto Y, Sato N, Miyahara K, Hirata D, Usui T, Takahashi H, Osada H, Miyakawa T.: Identification of Saccharomyces cerevisiae isoleucyl-tRNA synthetase as a target of the G1-specific inhibitor Reveromycin A.
    J Biol Chem, 277(32): 28810-28814 (2002) PMID: 12050165 [ doi: 10.1074/jbc.M203827200 ]
  • synthesis
  • Masuda T, Osako K, Shimizu T, Nakata T.: Total synthesis of reveromycin B.
    Org Lett, 1(6): 941-944 (1999) PMID: 10823225
  • Shimizu T, Masuda T, Hiramoto K, Nakata T.: Total synthesis of reveromycin A.
    Org Lett, 2(14): 2153-2156 (2000) PMID: 10891254
  • structure-activity relationship
  • Shimizu T, Usui T, Machida K, Furuya K, Osada H, Nakata T.: Chemical modification of reveromycin A and its biological activities.
    Bioorg Med Chem Lett, 12(23): 3363-3366 (2002) PMID: 12419362