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Review
. 2016 Feb 19;14(2):39.
doi: 10.3390/md14020039.

Chemical Diversity and Biological Properties of Secondary Metabolites from Sea Hares of Aplysia Genus

Renato B Pereira  1 , Paula B Andrade  2 , Patrícia Valentão  3
Affiliations
Review

Chemical Diversity and Biological Properties of Secondary Metabolites from Sea Hares of Aplysia Genus

Renato B Pereira et al. Mar Drugs. .

Abstract

The marine environment is an important source of structurally-diverse and biologically-active secondary metabolites. During the last two decades, thousands of compounds were discovered in marine organisms, several of them having inspired the development of new classes of therapeutic agents. Marine mollusks constitute a successful phyla in the discovery of new marine natural products (MNPs). Over a 50-year period from 1963, 116 genera of mollusks contributed innumerous compounds, Aplysia being the most studied genus by MNP chemists. This genus includes 36 valid species and should be distinguished from all mollusks as it yielded numerous new natural products. Aplysia sea hares are herbivorous mollusks, which have been proven to be a rich source of secondary metabolites, mostly of dietary origin. The majority of secondary metabolites isolated from sea hares of the genus Aplysia are halogenated terpenes; however, these animals are also a source of compounds from other chemical classes, such as macrolides, sterols and alkaloids, often exhibiting cytotoxic, antibacterial, antifungal, antiviral and/or antifeedant activities. This review focuses on the diverse structural classes of secondary metabolites found in Aplysia spp., including several compounds with pronounced biological properties.

Keywords: Aplysia; biological properties; mollusks; sea hares; secondary metabolites.

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Figures

Figure 1
Figure 1
Structures of aplyronines isolated from A. kurodai.
Figure 2
Figure 2
Structures of aplyolides isolated from Aplysia depilans.
Figure 3
Figure 3
C15-Acetogenins isolated from sea hares of Aplysia genus.
Figure 4
Figure 4
Eight-membered cyclic ether acetogenins isolated from sea hares of Aplysia genus.
Figure 5
Figure 5
Nine-membered cyclic ether acetogenins isolated from sea hares of Aplysia genus.
Figure 6
Figure 6
Alkaloids isolated from sea hares of Aplysia genus.
Figure 7
Figure 7
The 5α,8α-epidioxysterols from sea hares of Aplysia genus.
Figure 8
Figure 8
Degraded sterols from Aplysia sea hares containing the cis-hydrindane skeleton.
Figure 9
Figure 9
A 9,11-secosteroid from A. kurodai containing a tricyclic γ-diketone structure.
Figure 10
Figure 10
Pyrano-monoterpenes isolated from sea hares of the Aplysia genus.
Figure 11
Figure 11
Cyclic monoterpenes isolated from sea hares of the Aplysia genus.
Figure 12
Figure 12
Linear monoterpenes isolated from sea hares of the Aplysia genus.
Figure 13
Figure 13
Chamigrane sesquiterpenes isolated from sea hares of Aplysia genus.
Figure 14
Figure 14
Bisabolane sesquiterpenes isolated from sea hares of the Aplysia genus.
Figure 15
Figure 15
Cuparane sesquiterpenes isolated from sea hares of the Aplysia genus.
Figure 16
Figure 16
Laurane sesquiterpenes isolated from sea hares of the Aplysia genus.
Figure 17
Figure 17
Brasilane sesquiterpenes isolated from sea hares of the Aplysia genus.
Figure 18
Figure 18
First marine omphalane-derived sesquiterpene, isolated from A. dactylomela.
Figure 19
Figure 19
Eudesmane sesquiterpenes isolated from sea hares of the Aplysia genus.
Figure 20
Figure 20
Snyderane sesquiterpenes isolated from sea hares of the Aplysia genus.
Figure 21
Figure 21
Diterpenes isolated from sea hares of the Aplysia genus.
Figure 22
Figure 22
Brominated triterpenes with tetracyclic skeletons isolated from A. dactylomela.
Figure 23
Figure 23
Other metabolites isolated from sea hares of the Aplysia genus.
Figure 24
Figure 24
Distribution of compounds described in Aplysia spp. among the several chemical classes (A) and the prevalence of bioactivities attributed to them (B).
Figure 25
Figure 25
Bioactive compounds from sea hares of the Aplysia genus according to the chemical class.
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