Next Article in Journal
Composition and Enantiomeric Analysis of the Essential Oil of the Fruits and the Leaves of Pistacia vera from Greece
Previous Article in Journal
Solar Ultraviolet-B Radiation Increases Phenolic Content and Ferric Reducing Antioxidant Power in Avena sativa
Molecules 2007, 12(5), 1022-1034; doi:10.3390/12051022
Article

Evaluation of the Activity of the Sponge Metabolites Avarol and Avarone and their Synthetic Derivatives Against Fouling Micro- and Macroorganisms

1
,
2
,
4
,
5
,
5
,
5
,
5
,
2
,
1
 and
1,*
Received: 23 April 2007 / Revised: 13 May 2007 / Accepted: 14 May 2007 / Published: 15 May 2007
Download PDF [94 KB, uploaded 18 June 2014]

Abstract

The sesquiterpene hydroquinone avarol (1) was isolated from the marine sponge Dysidea avara, whereas the corresponding quinone, avarone (2), was obtained by oxidation of avarol, and the significantly more lipophilic compounds [3’-(p-chloro-phenyl)avarone (3), 3’,4’-ethylenedithioavarone (4), 4’-isopropylthioavarone (5), 4’-tert-butylthioavarone (6), 4’-propylthioavarone (7), 4’-octylthioavarone (8)] were obtained by nucleophilic addition of thiols or p-chloroaniline to avarone. All these compounds were tested, at concentrations ranging from 0.5 to 50 μg/mL, for their effect on the settlement of the cyprid stage of Balanus amphitrite, for toxicity to both nauplii and cyprids and for their growth inhibitory activity on marine bacteria (Cobetia marina, Marinobacterium stanieri, Vibrio fischeri and Pseudoalteromonas haloplanktis) and marine fungi (Halosphaeriopsis mediosetigera, Asteromyces cruciatus, Lulworthia uniseptata and Monodictys pelagica).
Keywords: Antifouling activity; settlement inhibition; antimicrobial activity; avarol; avarone Antifouling activity; settlement inhibition; antimicrobial activity; avarol; avarone
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

Tsoukatou, M.; Maréchal, J.P.; Hellio, C.; Novaković, I.; Tufegdzic, S.; Sladić, D.; Gašić, M.J.; Clare, A.S.; Vagias, C.; Roussis, V. Evaluation of the Activity of the Sponge Metabolites Avarol and Avarone and their Synthetic Derivatives Against Fouling Micro- and Macroorganisms. Molecules 2007, 12, 1022-1034.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert