Antineoplastic agents. Part 409: Isolation and structure of montanastatin from a terrestrial actinomycete.
A Montana soil actinomycete, Streptomyces anulatus, produced (1 x 10(-2)% yield) a new cancer cell growth inhibitory cyclooctadepsipeptide named montanastatin (1) accompanied by the potent anticancer antibiotic valinomycin (2) in very high (5.1%) yields. Valinomycin but not montanastatin inhibited growth of a number of pathogenic bacteria and fungi. Interpretation of high-field (500 MHz) NMR and high-resolution FAB mass spectral data allowed assignment of the structure cyclo-(D-Val-L-Lac-L-Val-D-Hiv) to montanastatin. Valinomycin (2) was also isolated from actinomycetes cultured from a tree branch and animal feces collected in Malaysia. Streptomyces exfoliatus, isolated from the tree branch, was found to contain valinomycin in 1.6% yield, while the fecal isolate, S. anulatus, gave valinomycin in 0.9% yield.
Cancer Research Institute and Department of Chemistry, Arizona State University, Tempe 85287-2404, USA.
G R
GR
Pettit
R
R
Tan
N
N
Melody
J M
JM
Kielty
R K
RK
Pettit
D L
DL
Herald
B E
BE
Tucker
L P
LP
Mallavia
D L
DL
Doubek
J M
JM
Schmidt
D000192:Actinomycetales / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured; D014634:Valinomycin / Q000737:chemistry / Q000494:pharmacology
D000970:Antineoplastic Agents; D010456:Peptides, Cyclic; C121494:montanastatin; D014634:Valinomycin