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
. 2008 Dec 18;10(24):5505-8.
doi: 10.1021/ol8020644.

Marineosins A and B, cytotoxic spiroaminals from a marine-derived actinomycete

Chollaratt Boonlarppradab  1 , Christopher A Kauffman, Paul R Jensen, William Fenical
Affiliations

Marineosins A and B, cytotoxic spiroaminals from a marine-derived actinomycete

Chollaratt Boonlarppradab et al. Org Lett. .

Abstract

Two novel spiroaminals, marineosins A and B (1, 2), containing two pyrrole functionalities, were isolated from cultures of a marine sediment-derived actinomycete related to the genus Streptomyces. The marineosins, which appear to be derived from unknown modifications of prodigiosin-like pigment pathways, showed significant inhibition of human colon carcinoma (HCT-116) in an in vitro assay (IC50 = 0.5 microM for marineosin A) and selective activities in diverse cancer cell types.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Selected COSY (bold lines) and HMBC NMR correlations (red arrows) observed for marineosin A (1).
Figure 2
Figure 2
Fragment ions observed in the EIMS experiment performed on marineosin A (1)
Figure 3
Figure 3
Assigned relative configuration of 1 based upon selected NOESY NMR correlations.
Figure 4
Figure 4
Large-ring conformation of 1 suggested by the pyrrole-ring shielded proton chemical shifts of H-17 and H-19.
Figure 5
Figure 5
Assigned relative configuration of 2 based upon selected NOESY NMR correlations.
Figure 6
Figure 6
Possible biosyntheses of 1 and 2 via a hetero Diels Alder cyclization.
See this image and copyright information in PMC

References

    1. Fenical W, Jensen PR. Nat Chem Biol. 2006;2:666–673. - PubMed
    2. Ward AC, Bull AT, Goodfellow M. Int J Syst Evol Microbiol. 2005;55:1759. - PubMed
    1. Bérdy J. J Antibiot. 2005;58:1–26. - PubMed
    1. Gontang EA, Fenical W, Jensen PR. Appl Env Micro. 2007;73:3272–3282. - PMC - PubMed

    1. Marineosin A (1): colorless oil; [α]D −101.7 (c 0.06, MeOH); UV (MeOH) λmax (log ε) 285 nm (4.06), 227 nm (3.88); IR νmax (KBr) 2925, 2856, 1610, 1508, 1435, 1261, 763 cm−1; NMR spectral data, see Table 1 and SI; HREIMS [M]+ m/z 409.2726 (calcd for C25H35N3O2, 409.2729).

    1. Morales JJ, Rodriguez AD. J Nat Prod. 1991;54:629–631. - PubMed
    2. Shen X, Perry TL, Dunbar CD, Kelly-Borges M, Hamann MT. J Nat Prod. 1998;61:1302–1303. - PubMed

Publication types

MeSH terms