Cupolamide A: A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola

Lea S. Bonnington; Junichi Tanaka; Tatsuo Higa; Junji Kimura; Yuki Yoshimura; Yoichi Nakao; Wesley Y. Yoshida; Paul J. Scheuer

doi:10.1021/jo9710285

Cupolamide A: A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola

Lea S. Bonnington, Junichi Tanaka, Tatsuo Higa, Junji Kimura, Yuki Yoshimura, Yoichi Nakao, Wesley Y. Yoshida, Paul J. Scheuer

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

36 Citations (Scopus)

Abstract

A new cyclic heptapeptide cupolamide A (1) was isolated from two samples of the sponge Theonella cupola collected in Indonesia and Okinawa. It contains two L-Val, one D-Leu, and one D-Ser, and three uncommon amino acid residues, D-homoarginine (Har), trans-4-hydroxy-L-proline (Hyp), and L-2,4-diaminobutanoic acid (Dba). The structure elucidation of 1 was performed by NMR spectroscopic techniques and the stereochemistry was determined by Marfey's method. Cupolamide A (1) was active against P388 murine leukemia cells with an IC₅₀ = 7.5 μg/mL.

Original language	English
Pages (from-to)	7765-7767
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	62
Issue number	22
DOIs	https://doi.org/10.1021/jo9710285
Publication status	Published - 1997
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Cupolamide A: A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola",

abstract = "A new cyclic heptapeptide cupolamide A (1) was isolated from two samples of the sponge Theonella cupola collected in Indonesia and Okinawa. It contains two L-Val, one D-Leu, and one D-Ser, and three uncommon amino acid residues, D-homoarginine (Har), trans-4-hydroxy-L-proline (Hyp), and L-2,4-diaminobutanoic acid (Dba). The structure elucidation of 1 was performed by NMR spectroscopic techniques and the stereochemistry was determined by Marfey's method. Cupolamide A (1) was active against P388 murine leukemia cells with an IC50 = 7.5 μg/mL.",

author = "Bonnington, {Lea S.} and Junichi Tanaka and Tatsuo Higa and Junji Kimura and Yuki Yoshimura and Yoichi Nakao and Yoshida, {Wesley Y.} and Scheuer, {Paul J.}",

year = "1997",

doi = "10.1021/jo9710285",

language = "English",

volume = "62",

pages = "7765--7767",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Cupolamide A

T2 - A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola

AU - Bonnington, Lea S.

AU - Tanaka, Junichi

AU - Higa, Tatsuo

AU - Kimura, Junji

AU - Yoshimura, Yuki

AU - Nakao, Yoichi

AU - Yoshida, Wesley Y.

AU - Scheuer, Paul J.

PY - 1997

Y1 - 1997

N2 - A new cyclic heptapeptide cupolamide A (1) was isolated from two samples of the sponge Theonella cupola collected in Indonesia and Okinawa. It contains two L-Val, one D-Leu, and one D-Ser, and three uncommon amino acid residues, D-homoarginine (Har), trans-4-hydroxy-L-proline (Hyp), and L-2,4-diaminobutanoic acid (Dba). The structure elucidation of 1 was performed by NMR spectroscopic techniques and the stereochemistry was determined by Marfey's method. Cupolamide A (1) was active against P388 murine leukemia cells with an IC50 = 7.5 μg/mL.

AB - A new cyclic heptapeptide cupolamide A (1) was isolated from two samples of the sponge Theonella cupola collected in Indonesia and Okinawa. It contains two L-Val, one D-Leu, and one D-Ser, and three uncommon amino acid residues, D-homoarginine (Har), trans-4-hydroxy-L-proline (Hyp), and L-2,4-diaminobutanoic acid (Dba). The structure elucidation of 1 was performed by NMR spectroscopic techniques and the stereochemistry was determined by Marfey's method. Cupolamide A (1) was active against P388 murine leukemia cells with an IC50 = 7.5 μg/mL.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

Cupolamide A: A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola

Abstract

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