Avarone

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],... 

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. 

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). 

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... 

W. E. G. Muller, R. K. Zahn, E. Eich Extraction and purification of avarone and avarol from Dysidea avara,Ger. Offen., DE 3621032 Al, 28th January 1988. 

W. E. G. Muller Application of avarol and avarone derivatives in combination with 3 -azido-3 -deoxythymidine for antiviral therapy, Ger. Offen., DE 3821676 Al, 8th February 1990. 

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