Antineoplastic agents. Part 409: Isolation and structure of montanastatin from a terrestrial actinomycete

George Pettit; Rui Tan; Noeleen Melody; Joshua M. Kielty; Robin Pettit; Delbert L. Herald; Bruce E. Tucker; Louis P. Mallavia; Dennis L. Doubek; Jean M. Schmidt

doi:10.1016/S0968-0896(99)00024-3

Antineoplastic agents. Part 409: Isolation and structure of montanastatin from a terrestrial actinomycete

George Pettit, Rui Tan, Noeleen Melody, Joshua M. Kielty, Robin Pettit, Delbert L. Herald, Bruce E. Tucker, Louis P. Mallavia, Dennis L. Doubek, Jean M. Schmidt

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

A Montana soil actinomycete, Streptomyces anulatus, produced (1x10^-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 (500MHz) 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. Copyright (C) 1999 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	895-899
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	7
Issue number	5
DOIs	https://doi.org/10.1016/S0968-0896(99)00024-3
State	Published - May 1999

Keywords

Actinomycete
Anticancer
Antimicrobial
Montanastatin
Valinomycin

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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title = "Antineoplastic agents. Part 409: Isolation and structure of montanastatin from a terrestrial actinomycete",

abstract = "A Montana soil actinomycete, Streptomyces anulatus, produced (1x10-2% 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 (500MHz) 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. Copyright (C) 1999 Elsevier Science Ltd.",

keywords = "Actinomycete, Anticancer, Antimicrobial, Montanastatin, Valinomycin",

author = "George Pettit and Rui Tan and Noeleen Melody and Kielty, {Joshua M.} and Robin Pettit and Herald, {Delbert L.} and Tucker, {Bruce E.} and Mallavia, {Louis P.} and Doubek, {Dennis L.} and Schmidt, {Jean M.}",

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AU - Tan, Rui

AU - Melody, Noeleen

AU - Kielty, Joshua M.

AU - Pettit, Robin

AU - Herald, Delbert L.

AU - Tucker, Bruce E.

AU - Mallavia, Louis P.

AU - Doubek, Dennis L.

AU - Schmidt, Jean M.

PY - 1999/5

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N2 - A Montana soil actinomycete, Streptomyces anulatus, produced (1x10-2% 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 (500MHz) 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. Copyright (C) 1999 Elsevier Science Ltd.

AB - A Montana soil actinomycete, Streptomyces anulatus, produced (1x10-2% 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 (500MHz) 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. Copyright (C) 1999 Elsevier Science Ltd.

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KW - Anticancer

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KW - Valinomycin

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Antineoplastic agents. Part 409: Isolation and structure of montanastatin from a terrestrial actinomycete

Abstract

Keywords

ASJC Scopus subject areas

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