Didemnins and tunichlorin: Novel natural products from the marine tunicate trididemnum solidum

Kenneth L. Rinehart; Vimal Kishore; Keith C. Bible; Ryuichi Sakai; David W. Sullins; Ka I.Ming Li

doi:10.1021/np50055a001

Didemnins and tunichlorin: Novel natural products from the marine tunicate trididemnum solidum

Kenneth L. Rinehart, Vimal Kishore, Keith C. Bible, Ryuichi Sakai, David W. Sullins, Ka I.Ming Li

Medical Oncology

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

99 Scopus citations

Abstract

Didemnins A, B, and C, cyclic depsipeptides previously reported by our laboratory from the Caribbean tunicate Trididemnum solidum, have now been synthesized and, in the process, their structures have been revised to include the new amino acid (3S,4R,5S)-isostatine, C₂H₅CH(CH₃)CHNH/IHOHCH2COOH. All other isomers of isostatine have also been prepared. Didemnin B is currently in Phase II clinical trials as an anticancer agent, and the antineoplastic activity, as well as the antiviral and immunosuppressive activities, of the didemnins are reviewed. A highly unusual porphynoid has also been isolated from T. solidum. The compound has been named tunichlorin and is apparently the first nickel-containing chlorin (and only the second nickel-containing porphyrin-related compound) identified from a living organism.

Original language	English (US)
Pages (from-to)	1-21
Number of pages	21
Journal	Journal of Natural Products
Volume	51
Issue number	1
DOIs	https://doi.org/10.1021/np50055a001
State	Published - Jan 1988

ASJC Scopus subject areas

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

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abstract = "Didemnins A, B, and C, cyclic depsipeptides previously reported by our laboratory from the Caribbean tunicate Trididemnum solidum, have now been synthesized and, in the process, their structures have been revised to include the new amino acid (3S,4R,5S)-isostatine, C2H5CH(CH3)CHNH/IHOHCH2COOH. All other isomers of isostatine have also been prepared. Didemnin B is currently in Phase II clinical trials as an anticancer agent, and the antineoplastic activity, as well as the antiviral and immunosuppressive activities, of the didemnins are reviewed. A highly unusual porphynoid has also been isolated from T. solidum. The compound has been named tunichlorin and is apparently the first nickel-containing chlorin (and only the second nickel-containing porphyrin-related compound) identified from a living organism.",

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AU - Kishore, Vimal

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AU - Sullins, David W.

AU - Li, Ka I.Ming

PY - 1988/1

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N2 - Didemnins A, B, and C, cyclic depsipeptides previously reported by our laboratory from the Caribbean tunicate Trididemnum solidum, have now been synthesized and, in the process, their structures have been revised to include the new amino acid (3S,4R,5S)-isostatine, C2H5CH(CH3)CHNH/IHOHCH2COOH. All other isomers of isostatine have also been prepared. Didemnin B is currently in Phase II clinical trials as an anticancer agent, and the antineoplastic activity, as well as the antiviral and immunosuppressive activities, of the didemnins are reviewed. A highly unusual porphynoid has also been isolated from T. solidum. The compound has been named tunichlorin and is apparently the first nickel-containing chlorin (and only the second nickel-containing porphyrin-related compound) identified from a living organism.

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Didemnins and tunichlorin: Novel natural products from the marine tunicate trididemnum solidum

Abstract

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