Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2019 Feb 6;17(2):100.
doi: 10.3390/md17020100.

New Acyclic Cytotoxic Jasplakinolide Derivative from the Marine Sponge Jaspis splendens

Affiliations

New Acyclic Cytotoxic Jasplakinolide Derivative from the Marine Sponge Jaspis splendens

Sherif S Ebada et al. Mar Drugs. .

Abstract

A new acylic jasplakinolide congener (2), another acyclic derivative requiring revision (4), together with two jasplakinolide derivatives including the parent compound jasplakinolide (1) were isolated from the Indonesian marine sponge Jaspis splendens. The chemical structures of the new and known compounds were unambiguously elucidated based on HRESIMS and exhaustive 1D and 2D NMR spectral analysis as well as a comparison of their NMR data with those of jasplakinolide (1). The isolated jasplakinolides inhibited the growth of mouse lymphoma (L5178Y) cells in vitro with IC50 values in the low micromolar to nanomolar range.

Keywords: Jaspis splendens; cytotoxic activity; jasplakinolide Z5; jasplakinolide Z6.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of 1–5.
Figure 2
Figure 2
1H NMR spectra of 1 and 2 showing differences in aromatic protons at the β-tyrosine residue.
Figure 3
Figure 3
Key 1H–1H COSY, HMBC and ROESY correlations of 2.
Figure 4
Figure 4
Key 1H–1H COSY and HMBC correlations of the tyrosine oxygenated moiety of 4.

References

    1. Zabriskie T.E., Klocke J.A., Ireland C.M., Marcus A.H., Molinski T.F., Faulkner D.J., Xu C., Clardy J.C. Jaspamide, a modified peptide from a Jaspis sponge, with insecticidal and antifungal activity. J. Am. Chem. Soc. 1986;108:3123–3124. doi: 10.1021/ja00271a062. - DOI
    1. Crews P., Manes L.V., Boehler M. Jasplakinolide, a cyclodepsipeptide from the marine sponge, Jaspis sp. Tetrahedron Lett. 1986;27:2797–2800. doi: 10.1016/S0040-4039(00)84645-6. - DOI
    1. Du L., Shen B. Biosynthesis of hybrid peptide-polyketide natural products. Curr. Opin. Drug Discov. Dev. 2001;4:215–228. - PubMed
    1. Ireland C., Scheuer P.J. Ulicyclamide and ulithiacyclamide, two new small peptides from a marine tunicate. J. Am. Chem. Soc. 1980;102:5688–5691. doi: 10.1021/ja00537a053. - DOI
    1. Scott V.R., Boehme R., Matthews T.R. New class of antifungal agents: Jasplakinolide, a cyclodepsipeptide from the marine sponge, Jaspis species. Antimicrob. Agents Chemother. 1988;32:1154–1157. doi: 10.1128/AAC.32.8.1154. - DOI - PMC - PubMed

MeSH terms

LinkOut - more resources