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Review
. 2013 May 17;11(5):1602-43.
doi: 10.3390/md11051602.

Meroterpenes from marine invertebrates: structures, occurrence, and ecological implications

Marialuisa Menna  1 , Concetta Imperatore, Filomena D'Aniello, Anna Aiello
Affiliations
Review

Meroterpenes from marine invertebrates: structures, occurrence, and ecological implications

Marialuisa Menna et al. Mar Drugs. .

Abstract

Meroterpenes are widely distributed among marine organisms; they are particularly abundant within brown algae, but other important sources include microorganisms and invertebrates. In the present review the structures and bioactivities of meroterpenes from marine invertebrates, mainly sponges and tunicates, are summarized. More than 300 molecules, often complex and with unique skeletons originating from intra- and inter-molecular cyclizations, and/or rearrangements, are illustrated. The reported syntheses are mentioned. The issue of a potential microbial link to their biosynthesis is also shortly outlined.

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Figures

Figure 1
Figure 1
Quinones and hydroquinones linked with linear prenyl chains.
Figure 2
Figure 2
Cyclodiprenyl hydroquinones/quinones.
Figure 3
Figure 3
Chromene (2H-benzopyran) derivatives.
Figure 4
Figure 4
Cyclic triprenylated quinone/hydroquinones.
Figure 5
Figure 5
Monomeric meta-and paracyclophane type meroterpenes.
Figure 6
Figure 6
Dimeric paracyclophane type meroterpenes.
Figure 7
Figure 7
Dimeric benzo[c]chromene-7,10-dione containing meroterpenes.
Figure 8
Figure 8
Prenylated thiazinoquinones from A. conicum.
Figure 9
Figure 9
Metachromins.
Figure 10
Figure 10
4,9-Friedodrimane-type skeleton containing meroterpenes of the avarol/avarone series.
Figure 11
Figure 11
Drimane-type skeleton containing meroterpenes.
Figure 12
Figure 12
Amino- and amino acid- substituted quinone containing meroterpenes.
Figure 13
Figure 13
Nakijiquinones and nakijinol.
Figure 14
Figure 14
Meroterpenoids with a fourth ring originated by an ether linkage between the benzo(hydro)quinone and terpene moieties.
Figure 15
Figure 15
Sesquimeroterpenoids with unusual and/or complex structures.
Figure 16
Figure 16
Diterpene benzo(hydro)quinones with linear or monocyclic terpene moieties.
Figure 17
Figure 17
Diterpene benzo(hydro)quinones with bicyclic terpene moieties.
Figure 18
Figure 18
Chromane meroditerpenes.
Figure 19
Figure 19
Diterpene benzo(hydro)quinones with tricyclic terpene moieties.
Figure 20
Figure 20
Strongylophorines and fascioquinols C and D.
Figure 21
Figure 21
Sestermeroterpenes: coscinoquinols, coscinosulfates, and halisulfates.
Figure 22
Figure 22
Sulfated triterpene hydroquinones.
Figure 23
Figure 23
Meroterpenoids from soft corals.
Figure 24
Figure 24
Meroterpenoids from marine invertebrates-associated Aspergillus spp.
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References

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