Isolation and structure of the marine sponge cell growth inhibitory cyclic peptide phakellistatin 1

George R. Pettit; Zbigniew Cichacz; Jozsef Barkoczy; Ann Christine Dorsaz; Delbert L. Herald; Michael D. Williams; Dennis L. Doubek; Jean M. Schmidt; Larry P. Tackett; Daniel C. Brune; Ronald L. Cerny; John N.A. Hooper; Gerald J. Bakus

doi:10.1021/np50092a011

Isolation and structure of the marine sponge cell growth inhibitory cyclic peptide phakellistatin 1

George R. Pettit, Zbigniew Cichacz, Jozsef Barkoczy, Ann Christine Dorsaz, Delbert L. Herald, Michael D. Williams, Dennis L. Doubek, Jean M. Schmidt, Larry P. Tackett, Daniel C. Brune, Ronald L. Cerny, John N.A. Hooper, Gerald J. Bakus

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Abstract

A new cell growth inhibitory (P-388 murine leukemia ED₅₀ 7.5 µg/ml) cycloheptapeptide designated phakellistatin 1 was isolated from two Indo-Pacific sponges, Phakellia costata and Stylotella aurantium. Structural elucidation was accomplished utilizing high field nmr, amino acid analyses, and mass spectral techniques (fab, tandem ms/ms), followed by chiral gas chromatographic procedures for absolute configuration assignments (all S-amino acid units). By these methods phakellistatin 1 [1] was found to be cyclo (Pro-Ile-Pro-Ile-Phe-Pro-Tyr), and this assignment was finally confirmed by an X-ray crystal structure determination.

Original language	English (US)
Pages (from-to)	260-267
Number of pages	8
Journal	Journal of Natural Products
Volume	56
Issue number	2
DOIs	https://doi.org/10.1021/np50092a011
State	Published - Feb 1993

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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Pettit, G. R., Cichacz, Z., Barkoczy, J., Dorsaz, A. C., Herald, D. L., Williams, M. D., Doubek, D. L., Schmidt, J. M., Tackett, L. P., Brune, D. C., Cerny, R. L., Hooper, J. N. A., & Bakus, G. J. (1993). Isolation and structure of the marine sponge cell growth inhibitory cyclic peptide phakellistatin 1. Journal of Natural Products, 56(2), 260-267. https://doi.org/10.1021/np50092a011

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title = "Isolation and structure of the marine sponge cell growth inhibitory cyclic peptide phakellistatin 1",

abstract = "A new cell growth inhibitory (P-388 murine leukemia ED50 7.5 µg/ml) cycloheptapeptide designated phakellistatin 1 was isolated from two Indo-Pacific sponges, Phakellia costata and Stylotella aurantium. Structural elucidation was accomplished utilizing high field nmr, amino acid analyses, and mass spectral techniques (fab, tandem ms/ms), followed by chiral gas chromatographic procedures for absolute configuration assignments (all S-amino acid units). By these methods phakellistatin 1 [1] was found to be cyclo (Pro-Ile-Pro-Ile-Phe-Pro-Tyr), and this assignment was finally confirmed by an X-ray crystal structure determination.",

author = "Pettit, {George R.} and Zbigniew Cichacz and Jozsef Barkoczy and Dorsaz, {Ann Christine} and Herald, {Delbert L.} and Williams, {Michael D.} and Doubek, {Dennis L.} and Schmidt, {Jean M.} and Tackett, {Larry P.} and Brune, {Daniel C.} and Cerny, {Ronald L.} and Hooper, {John N.A.} and Bakus, {Gerald J.}",

year = "1993",

month = feb,

doi = "10.1021/np50092a011",

language = "English (US)",

volume = "56",

pages = "260--267",

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issn = "0163-3864",

publisher = "American Chemical Society",

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T1 - Isolation and structure of the marine sponge cell growth inhibitory cyclic peptide phakellistatin 1

AU - Pettit, George R.

AU - Cichacz, Zbigniew

AU - Barkoczy, Jozsef

AU - Dorsaz, Ann Christine

AU - Herald, Delbert L.

AU - Williams, Michael D.

AU - Doubek, Dennis L.

AU - Schmidt, Jean M.

AU - Tackett, Larry P.

AU - Brune, Daniel C.

AU - Cerny, Ronald L.

AU - Hooper, John N.A.

AU - Bakus, Gerald J.

PY - 1993/2

Y1 - 1993/2

N2 - A new cell growth inhibitory (P-388 murine leukemia ED50 7.5 µg/ml) cycloheptapeptide designated phakellistatin 1 was isolated from two Indo-Pacific sponges, Phakellia costata and Stylotella aurantium. Structural elucidation was accomplished utilizing high field nmr, amino acid analyses, and mass spectral techniques (fab, tandem ms/ms), followed by chiral gas chromatographic procedures for absolute configuration assignments (all S-amino acid units). By these methods phakellistatin 1 [1] was found to be cyclo (Pro-Ile-Pro-Ile-Phe-Pro-Tyr), and this assignment was finally confirmed by an X-ray crystal structure determination.

AB - A new cell growth inhibitory (P-388 murine leukemia ED50 7.5 µg/ml) cycloheptapeptide designated phakellistatin 1 was isolated from two Indo-Pacific sponges, Phakellia costata and Stylotella aurantium. Structural elucidation was accomplished utilizing high field nmr, amino acid analyses, and mass spectral techniques (fab, tandem ms/ms), followed by chiral gas chromatographic procedures for absolute configuration assignments (all S-amino acid units). By these methods phakellistatin 1 [1] was found to be cyclo (Pro-Ile-Pro-Ile-Phe-Pro-Tyr), and this assignment was finally confirmed by an X-ray crystal structure determination.

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SN - 0163-3864

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EP - 267

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 2

ER -

Isolation and structure of the marine sponge cell growth inhibitory cyclic peptide phakellistatin 1

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ASJC Scopus subject areas

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