Yaku'amides A and B, cytotoxic linear peptides rich in dehydroamino acids from the marine sponge Ceratopsion sp

Reiko Ueoka; Yuji Ise; Susumu Ohtsuka; Shigeru Okada; Takao Yamori; Shigeki Matsunaga

doi:10.1021/ja109275z

Yaku'amides A and B, cytotoxic linear peptides rich in dehydroamino acids from the marine sponge Ceratopsion sp

J Am Chem Soc. 2010 Dec 22;132(50):17692-4. doi: 10.1021/ja109275z. Epub 2010 Dec 1.

Authors

Reiko Ueoka¹, Yuji Ise, Susumu Ohtsuka, Shigeru Okada, Takao Yamori, Shigeki Matsunaga

Affiliation

¹ Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.

PMID: 21121605
DOI: 10.1021/ja109275z

Abstract

Two cytotoxic peptides, yaku'amides A (1) and B (2), were isolated from the marine sponge Ceratopsion sp. Their planar structures were elucidated on the basis of spectroscopic data, whereas the absolute configurations were determined by a combination of the Marfey's analysis and dansylation analysis of the total and partial acid hydrolysis products. The growth inhibitory profile of yaku'amide A against a panel of 39 human cancer cell lines was clearly unique and distinguished from other anticancer drugs.

MeSH terms

Amides* / chemistry
Amides* / isolation & purification
Amides* / pharmacology
Amino Acid Sequence
Animals
Antineoplastic Agents* / chemistry
Antineoplastic Agents* / isolation & purification
Antineoplastic Agents* / pharmacology
Aquatic Organisms
Cell Line, Tumor
Cell Proliferation / drug effects
Humans
Inhibitory Concentration 50
Leukemia / drug therapy
Mice
Molecular Sequence Data
Molecular Structure
Oligopeptides / chemistry
Oligopeptides / isolation & purification*
Oligopeptides / pharmacology*
Peptides / chemistry
Peptides / isolation & purification
Peptides / pharmacology
Porifera / chemistry*

Substances

Amides
Antineoplastic Agents
Oligopeptides
Peptides
yaku'amide A
yaku'amide B