Avarol

Muller, W. E. G., Bohm, M., Batel, R., Rosa, S. D., Tommonaro, G., Muller, I. M., and Schroder, H. C. (2000). Application of cell culture for the production of bioactive compounds from sponges Synthesis of avarol by primmorphs from Dysidea avara. J. Nat. Prod. 63,1077-1081. 

Loya S, Hizi A. The inhibition of human immunodeficiency vims type 1 reverse transcriptase by avarol and avarone derivatives. FEBS Lett 1990 269 131-134. 

Puupehenone (63) is a member of a distinctive family of sponge metabolites — a sesquiterpene joined to a C6-shikimate moiety — first exemplified by the quinol-quinone pair of avarol and avarone. Among the varied activities that have been reported for this diverse class of compounds is the property of ilimaquinone to inhibit replication of the HIV virus.78 Preliminary screening of puupehenone against Mycobacterium tuberculosis showed 99% inhibition of the organism. A series of chemical modifications have been conducted on puupehenone to study the effect on its biological activity. 

From another Dysidea sponge species, Dysidea avara, the sesquiterpenes avarol, Fig. (9) and avarone, Fig. (10), which show a wide variety of biological activities, were first isolated. Both compounds are potent antileukemic agents in vitro and in vivo. They were determined to be neither direct mutagens nor premutagens, and they displayed antimutagenic activity... 

Both avarol and avarone inhibit replication of the ethiological agent of acquired immuno-deficiency syndrome (AIDS) [77], Additionally, avarol and avarone effectively control acute inflammation in experimental models after either oral or topical administration. Their anti-inflammatory activity may result from inhibition of eicosanoid release and depression of superoxide generation in leukocytes [78], Several studies reviewed the structures and bioactivity of compounds related to avarone as an antihuman immuno-deficiency virus (HIV), antitopoisomerase II activity and as proteinkinase C (PKC) inhibitors [3, 79],... 

Melemeleones A and B (320 and 321) possess a 4,9-friedodrimane sesquiterpene array linked to a quinone bearing a taurine and they are structurally related to avarol. Compounds 320 and 321 were isolated from the sponge Dysidea sp. and identified by analysis of their spectroscopic data. Compound 321 showed a moderate inhibitory activity against the pp60v src protein Tyrosine Kinase with an IC50 of 28 pM [236]. 

Mamanulhaquinone (1) is a combination of a sesquiterpene and a quinone. Its skeleton, with both terpene and quinone or hy-droquinone portions, is not unusual for a natural product derived from a sponge.2 An example is avarol (2). containing a hydroqui-none ring and the terpene skeleton of drimane.3... 

The sesquiterpene quinones and hydroquinones display a wide range of biological activities.4 Some of the compounds are cytu-toxic, whereas others show antimicrobial characteristics. Avarol (2) has been the subject of investigation as a consequence of its ability to inhibit reverse transcriptase, but no clinical value (as an anti-AIDS agent, for example) has yet been established.3... 

Tropical rainforest tree and Malaysian tree A number of natural products have been reported to interact with reverse transcriptase, i.e., baicalin, avarol, avarone, psycho-trine, phloroglucinol derivatives and, in particular, calanolides (from the tropical rainforest tree, Calophyllum lanigerum) and inophyllums (from the Malaysian tree, Calophyllum inophyllum). 

AVAROL, AVARONE, PSYCHOTRINE, AND PHLOROGLUCINOL DERIVATIVES (i.e., MALLOTOJAPONIN)... 

Avarol and avarone derivatives (from the Red Sea sponge Dysidea cinerea), the alkaloids psy-chotrine and O-methylpsychotrine (from ipecac, the dried rhizome and root of Cephaelis ipecacuanha), and phloroglucinol derivatives such as mallotojaponin, from the pericarps of Mallotus japonicus, have all been reported to inhibit the reverse transcriptase activity of HIV-1, noncom-petitively with respect to the natural substrate (dNTP). In neither case was the anti-HIV-1 activity determined in cell culture, so it is not clear whether any of these compounds is really an effective... 

Illimaquinone, such as avarone and avarol isolated from a Red Sea sponge, i.e., Smenospongia, has been reported to inhibit the RNase H activity associated with the HIV-1 reverse transcriptase at a concentration of 5 to 10 pg/rnl, whereas it was not active against the RNA-dependent DNA polymerase (RDDP) and DNA-dependent DNA polymerase (DDDP) activities of the enzyme at a concentration of 50 pg/rnl. 

Muller, W. E. G., Diehl-Seifert, B., Sobel, C., Bechtold, A., Kljajic, Z., and Dorn, A., Sponge secondary metabolites biochemical and ultrastructural localization of the antimitotic agent avarol in Dysidea avara, J. Histochem. Cytochem., 34, 1687, 1986. 

The semisynthesis of avinosol was performed from avarone (8) and 2 -deoxyinosine to confirm the structure of the natural product. Avarone was prepared by oxidation of the naturally occurring avarol (9) obtained in the same extract (Scheme 9.1). 

There are three AVASOL.q, designed for the requirements of various users. AVAROL Mo. 10 is a light-bodied paste designed for optimum softening and lubricating properties. AVASOL No. 

Sponges produce furanosesquiterpenes of various skeletal types, such as furodysinin (118) from Dysidea herbacea and nakafuran-8 (119) from D. etheria, the latter of which is antifeeding. Similarly, mixed shikrmate-mevalonate metabolites are often encountered as sponge metabolites the first example is avarol (120), which was isolated from Dysidea avara. Several related compounds have been isolated from dictyoceratid... 

Anti-HIV compounds from marine sources also included terpenoids, steroids, peptides and alkaloids. Avarol, Fig. (1) and avarone. Fig. (2), sesquiterpenoid hydroquinones from the marine sponge Dysidea cinerea, are promising anti-HIV compounds [41,42]. Three new... 

Interference with assembly of viral coat proteins and viral RNA into new virus particles. Interferons may induce in the ribosomes of the host cells production of enzymes that inhibit translation of viral proteins. Avarol and avarine are thought to interfere with cytoskeletal assembly of virus particles. PROTEASE inhibitors can prevent the release of reverse transcriptase, and HIV-1 proteinase (e.g. saquinavir) are under development or in trial application. 

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