Antineoplastic agents. 560. Isolation and structure of kitastatin 1 from an alaskan Kitasatospora sp.

George Pettit, Rui Tan, Robin Pettit, Thomas H. Smith, Song Feng, Dennis L. Doubek, Linda Richert, John Hamblin, Christine Weber, Jean Chapuis

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

By utilizing a bioassay-guided separation (P388 lymphocytic leukemia and a panel of human cancer cell lines) of fermentation broths from a Kitasatospora sp. collected from a tundra soil sample taken at the shore of the Beaufort Sea, we have isolated three powerful (GI50 to 0.0006 μg/mL) cancer cell growth inhibitors (1-3) and determined their structures to be closely related cyclodepsipeptides. From 380 L fermentations of Kitasatospora sp. were obtained 2.6 mg of a new cyclodepsipeptide designated kitastatin 1 (3), accompanied by the previously known respirantin (1, 10.8 mg) and its valeryl homologue (2, 4.8 mg). The structures were determined by employment of a series of high-resolution mass and 2D NMR spectroscopic analyses. The stereochemical assignments and overall structures were confirmed by subsequent total synthesis of depsipdptide 1, as reported in the accompanying contribution.

Original languageEnglish (US)
Pages (from-to)1069-1072
Number of pages4
JournalJournal of Natural Products
Volume70
Issue number7
DOIs
StatePublished - Jul 2007

Fingerprint

Kitasatospora
Depsipeptides
antineoplastic agents
Antineoplastic Agents
Fermentation
fermentation
tundra soils
Beaufort Sea
Lymphoid Leukemia
Growth Inhibitors
lymphocytic leukemia
Bioassay
Oceans and Seas
Biological Assay
cell growth
Neoplasms
Soil
soil sampling
bioassays
Cells

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Antineoplastic agents. 560. Isolation and structure of kitastatin 1 from an alaskan Kitasatospora sp. / Pettit, George; Tan, Rui; Pettit, Robin; Smith, Thomas H.; Feng, Song; Doubek, Dennis L.; Richert, Linda; Hamblin, John; Weber, Christine; Chapuis, Jean.

In: Journal of Natural Products, Vol. 70, No. 7, 07.2007, p. 1069-1072.

Research output: Contribution to journalArticle

Pettit, George ; Tan, Rui ; Pettit, Robin ; Smith, Thomas H. ; Feng, Song ; Doubek, Dennis L. ; Richert, Linda ; Hamblin, John ; Weber, Christine ; Chapuis, Jean. / Antineoplastic agents. 560. Isolation and structure of kitastatin 1 from an alaskan Kitasatospora sp. In: Journal of Natural Products. 2007 ; Vol. 70, No. 7. pp. 1069-1072.
@article{9209bc1135c5440db3966dff6c947192,
title = "Antineoplastic agents. 560. Isolation and structure of kitastatin 1 from an alaskan Kitasatospora sp.",
abstract = "By utilizing a bioassay-guided separation (P388 lymphocytic leukemia and a panel of human cancer cell lines) of fermentation broths from a Kitasatospora sp. collected from a tundra soil sample taken at the shore of the Beaufort Sea, we have isolated three powerful (GI50 to 0.0006 μg/mL) cancer cell growth inhibitors (1-3) and determined their structures to be closely related cyclodepsipeptides. From 380 L fermentations of Kitasatospora sp. were obtained 2.6 mg of a new cyclodepsipeptide designated kitastatin 1 (3), accompanied by the previously known respirantin (1, 10.8 mg) and its valeryl homologue (2, 4.8 mg). The structures were determined by employment of a series of high-resolution mass and 2D NMR spectroscopic analyses. The stereochemical assignments and overall structures were confirmed by subsequent total synthesis of depsipdptide 1, as reported in the accompanying contribution.",
author = "George Pettit and Rui Tan and Robin Pettit and Smith, {Thomas H.} and Song Feng and Doubek, {Dennis L.} and Linda Richert and John Hamblin and Christine Weber and Jean Chapuis",
year = "2007",
month = "7",
doi = "10.1021/np068072c",
language = "English (US)",
volume = "70",
pages = "1069--1072",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "7",

}

TY - JOUR

T1 - Antineoplastic agents. 560. Isolation and structure of kitastatin 1 from an alaskan Kitasatospora sp.

AU - Pettit, George

AU - Tan, Rui

AU - Pettit, Robin

AU - Smith, Thomas H.

AU - Feng, Song

AU - Doubek, Dennis L.

AU - Richert, Linda

AU - Hamblin, John

AU - Weber, Christine

AU - Chapuis, Jean

PY - 2007/7

Y1 - 2007/7

N2 - By utilizing a bioassay-guided separation (P388 lymphocytic leukemia and a panel of human cancer cell lines) of fermentation broths from a Kitasatospora sp. collected from a tundra soil sample taken at the shore of the Beaufort Sea, we have isolated three powerful (GI50 to 0.0006 μg/mL) cancer cell growth inhibitors (1-3) and determined their structures to be closely related cyclodepsipeptides. From 380 L fermentations of Kitasatospora sp. were obtained 2.6 mg of a new cyclodepsipeptide designated kitastatin 1 (3), accompanied by the previously known respirantin (1, 10.8 mg) and its valeryl homologue (2, 4.8 mg). The structures were determined by employment of a series of high-resolution mass and 2D NMR spectroscopic analyses. The stereochemical assignments and overall structures were confirmed by subsequent total synthesis of depsipdptide 1, as reported in the accompanying contribution.

AB - By utilizing a bioassay-guided separation (P388 lymphocytic leukemia and a panel of human cancer cell lines) of fermentation broths from a Kitasatospora sp. collected from a tundra soil sample taken at the shore of the Beaufort Sea, we have isolated three powerful (GI50 to 0.0006 μg/mL) cancer cell growth inhibitors (1-3) and determined their structures to be closely related cyclodepsipeptides. From 380 L fermentations of Kitasatospora sp. were obtained 2.6 mg of a new cyclodepsipeptide designated kitastatin 1 (3), accompanied by the previously known respirantin (1, 10.8 mg) and its valeryl homologue (2, 4.8 mg). The structures were determined by employment of a series of high-resolution mass and 2D NMR spectroscopic analyses. The stereochemical assignments and overall structures were confirmed by subsequent total synthesis of depsipdptide 1, as reported in the accompanying contribution.

UR - http://www.scopus.com/inward/record.url?scp=34548017851&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34548017851&partnerID=8YFLogxK

U2 - 10.1021/np068072c

DO - 10.1021/np068072c

M3 - Article

C2 - 17608530

AN - SCOPUS:34548017851

VL - 70

SP - 1069

EP - 1072

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 7

ER -