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 journalArticle

111 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)2538-2543
Number of pages6
JournalJournal of Organic Chemistry
Volume58
Issue number9
StatePublished - 1993

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Tubulin
Antimitotic Agents
Vinblastine
Polyethers
Macrolides
Guanosine Triphosphate
Polymerization
Cells
Nuclear magnetic resonance
homohalichondrin B
halichondrin B

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Pettit, G., Tan, R., Gao, F., Williams, M. D., Doubek, D. L., Boyd, M. R., ... Tackett, L. P. (1993). Isolation and structure of halistatin 1 from the Eastern Indian Ocean marine sponge Phakellia carteri. Journal of Organic Chemistry, 58(9), 2538-2543.

Isolation and structure of halistatin 1 from the Eastern Indian Ocean marine sponge Phakellia carteri. / Pettit, George; Tan, Rui; Gao, Feng; Williams, Michael D.; Doubek, Dennis L.; Boyd, Michael R.; Schmidt, Jean M.; Chapuis, Jean; Hamel, Ernest; Bai, Ruoli; Hooper, John N A; Tackett, Larry P.

In: Journal of Organic Chemistry, Vol. 58, No. 9, 1993, p. 2538-2543.

Research output: Contribution to journalArticle

Pettit, G, Tan, R, Gao, F, Williams, MD, Doubek, DL, Boyd, MR, Schmidt, JM, Chapuis, J, Hamel, E, Bai, R, Hooper, JNA & Tackett, LP 1993, 'Isolation and structure of halistatin 1 from the Eastern Indian Ocean marine sponge Phakellia carteri', Journal of Organic Chemistry, vol. 58, no. 9, pp. 2538-2543.
Pettit, George ; Tan, Rui ; Gao, Feng ; Williams, Michael D. ; Doubek, Dennis L. ; Boyd, Michael R. ; Schmidt, Jean M. ; Chapuis, Jean ; Hamel, Ernest ; Bai, Ruoli ; Hooper, John N A ; Tackett, Larry P. / Isolation and structure of halistatin 1 from the Eastern Indian Ocean marine sponge Phakellia carteri. In: Journal of Organic Chemistry. 1993 ; Vol. 58, No. 9. pp. 2538-2543.
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