Reveromycin A, B, C, D

• Print

Structure

A:
B:
C:
D:

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)

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)

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)

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)

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)

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)

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) [ 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)

Shimizu T, Masuda T, Hiramoto K, Nakata T.: Total synthesis of reveromycin A.
Org Lett, 2(14): 2153-2156 (2000)

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)