Isolation and Structure of Halistatin 1 from the Eastern Indian Ocean Marine Sponge Phakellia carteri

George Pettit; Rui Tan; Feng Gao; Michael D. Williams; Dennis L. Doubek; Michael R. Boyd; Jean M. Schmidt; Jean Chapuis; Ernest Hamel; Ruoli Bai; John N A Hooper; Larry P. Tackett

doi:10.1021/jo00061a030

Isolation and Structure of Halistatin 1 from the Eastern Indian Ocean Marine Sponge Phakellia carteri

George Pettit, Rui Tan, Feng Gao, Michael D. Williams, Dennis L. Doubek, Michael R. Boyd, Jean M. Schmidt, Jean Chapuis, Ernest Hamel, Ruoli Bai, John N A Hooper, Larry P. Tackett

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

125 Scopus citations

Abstract

A highly potent new polyether macrolide antimitotic agent designated halistatin 1 (5) was isolated (8.8 × 10⁻⁷% yield) from Phakellia carteri. The marine sponge was located in coastal areas of the Republic of the Comoros, and it was also found to contain halichondrin B (3) and homohalichondrin B (4). Structure elucidation of halistatin 1 (5) was achieved primarily by employing extensive high-field (400- and 500-MHz) 2D NMR techniques. Halistatin 1, like halichondrin B and homohalichondrin B, caused the accumulation of cells arrested in mitosis, inhibited tubulin polymerization, and inhibited the binding of radiolabeled vinblastine and GTP to tubulin.

Original language	English (US)
Pages (from-to)	2538-2543
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	58
Issue number	9
DOIs	https://doi.org/10.1021/jo00061a030
State	Published - 1993

ASJC Scopus subject areas

Organic Chemistry

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title = "Isolation and Structure of Halistatin 1 from the Eastern Indian Ocean Marine Sponge Phakellia carteri",

abstract = "A highly potent new polyether macrolide antimitotic agent designated halistatin 1 (5) was isolated (8.8 × 10−7% yield) from Phakellia carteri. The marine sponge was located in coastal areas of the Republic of the Comoros, and it was also found to contain halichondrin B (3) and homohalichondrin B (4). Structure elucidation of halistatin 1 (5) was achieved primarily by employing extensive high-field (400- and 500-MHz) 2D NMR techniques. Halistatin 1, like halichondrin B and homohalichondrin B, caused the accumulation of cells arrested in mitosis, inhibited tubulin polymerization, and inhibited the binding of radiolabeled vinblastine and GTP to tubulin.",

author = "George Pettit and Rui Tan and Feng Gao and Williams, {Michael D.} and Doubek, {Dennis L.} and Boyd, {Michael R.} and Schmidt, {Jean M.} and Jean Chapuis and Ernest Hamel and Ruoli Bai and Hooper, {John N A} and Tackett, {Larry P.}",

year = "1993",

doi = "10.1021/jo00061a030",

language = "English (US)",

volume = "58",

pages = "2538--2543",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Isolation and Structure of Halistatin 1 from the Eastern Indian Ocean Marine Sponge Phakellia carteri

AU - Pettit, George

AU - Tan, Rui

AU - Gao, Feng

AU - Williams, Michael D.

AU - Doubek, Dennis L.

AU - Boyd, Michael R.

AU - Schmidt, Jean M.

AU - Chapuis, Jean

AU - Hamel, Ernest

AU - Bai, Ruoli

AU - Hooper, John N A

AU - Tackett, Larry P.

PY - 1993

Y1 - 1993

N2 - A highly potent new polyether macrolide antimitotic agent designated halistatin 1 (5) was isolated (8.8 × 10−7% yield) from Phakellia carteri. The marine sponge was located in coastal areas of the Republic of the Comoros, and it was also found to contain halichondrin B (3) and homohalichondrin B (4). Structure elucidation of halistatin 1 (5) was achieved primarily by employing extensive high-field (400- and 500-MHz) 2D NMR techniques. Halistatin 1, like halichondrin B and homohalichondrin B, caused the accumulation of cells arrested in mitosis, inhibited tubulin polymerization, and inhibited the binding of radiolabeled vinblastine and GTP to tubulin.

AB - A highly potent new polyether macrolide antimitotic agent designated halistatin 1 (5) was isolated (8.8 × 10−7% yield) from Phakellia carteri. The marine sponge was located in coastal areas of the Republic of the Comoros, and it was also found to contain halichondrin B (3) and homohalichondrin B (4). Structure elucidation of halistatin 1 (5) was achieved primarily by employing extensive high-field (400- and 500-MHz) 2D NMR techniques. Halistatin 1, like halichondrin B and homohalichondrin B, caused the accumulation of cells arrested in mitosis, inhibited tubulin polymerization, and inhibited the binding of radiolabeled vinblastine and GTP to tubulin.

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DO - 10.1021/jo00061a030

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SN - 0022-3263

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

Isolation and Structure of Halistatin 1 from the Eastern Indian Ocean Marine Sponge Phakellia carteri

Abstract

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