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Review
. 2016 Jan 14;14(1):16.
doi: 10.3390/md14010016.

Marine Isonitriles and Their Related Compounds

Jens Emsermann  1 , Ulrich Kauhl  2 , Till Opatz  3
Affiliations
Review

Marine Isonitriles and Their Related Compounds

Jens Emsermann et al. Mar Drugs. .

Abstract

Marine isonitriles represent the largest group of natural products carrying the remarkable isocyanide moiety. Together with marine isothiocyanates and formamides, which originate from the same biosynthetic pathways, they offer diverse biological activities and in spite of their exotic nature they may constitute potential lead structures for pharmaceutical development. Among other biological activities, several marine isonitriles show antimalarial, antitubercular, antifouling and antiplasmodial effects. In contrast to terrestrial isonitriles, which are mostly derived from α-amino acids, the vast majority of marine representatives are of terpenoid origin. An overview of all known marine isonitriles and their congeners will be given and their biological and chemical aspects will be discussed.

Keywords: antibiotics; carbonimidic dichlorides; formamides; isonitriles; isothiocyanates; malaria; marine natural products; terpenes.

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Figures

Figure 1
Figure 1
Xanthocillin (1), axisonitrile-1 (2) and axisothiocyanate (3).
Figure 2
Figure 2
Skeletal-types of sesquiterpenoids (arrows indicate potential attachment points of the nitrogenous function).
Figure 3
Figure 3
Axanes.
Figure 4
Figure 4
Eudesmanes.
Figure 5
Figure 5
Dimeric sesquiterpenoids with eudesmane skeleton.
Figure 6
Figure 6
Cadinanes.
Figure 7
Figure 7
Spiroaxanes.
Figure 8
Figure 8
Aromadendranes.
Figure 9
Figure 9
Epimaalianes.
Figure 10
Figure 10
Pupukeananes.
Figure 11
Figure 11
Bisabolanes.
Figure 12
Figure 12
Oxygenated bisabolanes.
Figure 13
Figure 13
Guaianes.
Figure 14
Figure 14
Further sesquiterpenoids.
Figure 15
Figure 15
Acyclic diterpenoids.
Figure 16
Figure 16
Malonganenones.
Figure 17
Figure 17
Tetrahydropyran kalihinols.
Figure 18
Figure 18
Tetrahydrofuran-substituted kalihinols.
Figure 19
Figure 19
Isokalihinols.
Figure 20
Figure 20
Kalihinenes.
Figure 21
Figure 21
Kalihipyrans.
Figure 22
Figure 22
Intermediates.
Figure 23
Figure 23
Amphilectane frameworks.
Figure 24
Figure 24
Amphilectenes.
Figure 25
Figure 25
Cycloamphilectenes.
Figure 26
Figure 26
Isocycloamphilectanes.
Figure 27
Figure 27
Neopamphilectene.
Figure 28
Figure 28
Isoneoamphilectenes.
Figure 29
Figure 29
Acyclic and monocyclic carbonimidic dichlorides.
Figure 30
Figure 30
Bicyclic carbonimidic dichlorides.
Figure 31
Figure 31
Farnesyls.
Figure 32
Figure 32
Lipid and amino alcohol derivatives.
Figure 33
Figure 33
Long-chain isothiocyanates.
Figure 34
Figure 34
Derivatives with C7- and C9-carbon skeletons.
Figure 35
Figure 35
Thiocyanatins.
Figure 36
Figure 36
Cylindricins and Fasicularin.
Figure 37
Figure 37
Psammaplin B.
Figure 38
Figure 38
Proposed biosynthesis to sesquiterpenoids.
Figure 39
Figure 39
Proposed biosynthesis of diterpenoids [12,14,99].
Figure 40
Figure 40
Proposed biosynthesis of carbonimidic dichlorides.
Figure 41
Figure 41
Number of new marine isonitriles and related compounds found until 2015.
See this image and copyright information in PMC

References

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