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Review
. 2006 Jan 31;11(1):1-33.
doi: 10.3390/11010001.

Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order Dictyoceratida

Dusan Sladić  1 , Miroslav J Gasić
Affiliations
Review

Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order Dictyoceratida

Dusan Sladić et al. Molecules. .

Abstract

A review of results of bioactivity and reactivity examinations of marine sesquiterpene (hydro)quinones is presented. The article is focused mostly on friedo- rearranged drimane structural types, isolated from sponges of the order Dictyoceratida. Examples of structural correlations are outlined. Available results on the mechanism of redox processes and examinations of chemo- and regioselectivity in addition reactions are presented and, where possible, analyzed in relation to established bioactivities. Most of the bioactivity examinations are concerned with antitumor activities and the mechanism thereof, such as DNA damage, arylation of nucleophiles, tubulin assembly inhibition, protein kinase inhibition, inhibition of the arachidonic cascade, etc. Perspectives on marine drug development are discussed with respect to biotechnological methods and synthesis. Examples of the recognition of validated core structures and synthesis of structurally simplified compounds retaining modes of activity are analyzed.

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Figures

Figure 1
Figure 1
Hydroquinones and quinones with friedo-rearranged drimane skeleton.
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Scheme 1
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Scheme 4
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Scheme 5
Figure 2
Figure 2
Activation of position 3’ in avarone by protonation.
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Scheme 6
Figure 3
Figure 3
The PM3 optimized geometry of 13.
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Scheme 7
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Figure 9
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Figure 10
(a) Plot of Ep vs. log cCTAB for 1 mM avarone at pH 9,1 (o); (b) Plot of log k vs. log cCTAB at pH 9.1 for the reaction of BNAH and avarone (●).
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Figure 11
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Figure 19
Examples of nakijiquinone library structural types.
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Figure 20
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Figure 22
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References

    1. Berquist P.R. Sponges. Hutchinson; London: 1978.
    1. Simpson T.L. The cell biology of sponges. Springer; New York: 1984.
    1. Faulkner D.J. Marine natural products. Nat. Prod. Rep. 2002;19:1–48. - PubMed

    2. and earlier reviews in this series.

    1. Blunt J.W., Copp B.R., Munro M.H.G., Northcote P.T., Prinsep M.R. Marine natural products. Nat. Prod. Rep. 2005;22:15–61. doi: 10.1039/b415080p. - DOI - PubMed

    2. and earlier reviews in this series.

    1. Faulkner D.J. Marine Pharmacology. A. van Leeuwenhoek. 2000;77:135–145. doi: 10.1023/A:1002405815493. - DOI - PubMed

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