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Review
. 2018 Jan 1;16(1):6.
doi: 10.3390/md16010006.

Marine Alkylpurines: A Promising Group of Bioactive Marine Natural Products

Pablo A García  1 , Elena Valles  2 , David Díez  3 , María-Ángeles Castro  4
Affiliations
Review

Marine Alkylpurines: A Promising Group of Bioactive Marine Natural Products

Pablo A García et al. Mar Drugs. .

Abstract

Marine secondary metabolites with a purine motif in their structure are presented in this review. The alkylpurines are grouped according to the size of the alkyl substituents and their location on the purine ring. Aspects related to the marine source, chemical structure and biological properties are considered together with synthetic approaches towards the natural products and bioactive analogues. This review contributes to studies of structure-activity relationships for these metabolites and highlights the potential of the sea as a source of new lead compounds in diverse therapeutic fields.

Keywords: alkylpurines; antimicrobial activity; cytotoxicity; marine natural products; methylpurines; purines; terpenylpurines.

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Conflict of interest statement

The authors declare no conflict of interest. The founding sponsors had no role in the design of the study, in the data collection, and in the writing and decision to publish the manuscript.

Figures

Figure 1
Figure 1
Structures of 1-methyladenine, herbipoline and related compounds.
Figure 2
Figure 2
Structure of several methylated guanines.
Figure 3
Figure 3
Structure of several methylated isoguanines.
Figure 4
Figure 4
Structure of mucronatine, 16, and methylmucronatine, 17.
Figure 5
Figure 5
Structure of nigricines 18–21.
Figure 6
Figure 6
Structure of methylated xanthines 22–26.
Figure 7
Figure 7
Structure of methylated 8-oxopurines 27 and 28.
Figure 8
Figure 8
Structure of methylated 8-oxopurines 29–32.
Figure 9
Figure 9
Structure of methylated 8-oxopurines 33–38.
Figure 10
Figure 10
Structure of agelasine.
Figure 11
Figure 11
Structure of malonganenones 39–46.
Figure 12
Figure 12
Structures of nuttingins 47–52.
Figure 13
Figure 13
Structure of agelasines E and F and related compounds 53–57.
Figure 14
Figure 14
Structure of agelasines A and B and analogues 58–62.
Figure 15
Figure 15
Structures of agelasines 63–69.
Figure 16
Figure 16
Structures of agelasines 70–72.
Figure 17
Figure 17
Structure of agelasines 73–77.
Figure 18
Figure 18
Structures of agelasines 78–84.
Figure 19
Figure 19
Structures of agelasimines A and B and gelasines A and B.
Figure 20
Figure 20
Structures of agelasines 89–93.
Figure 21
Figure 21
Structure of terpenylpurines 94–96.
Figure 22
Figure 22
Structures of asmarines 97–107.
Figure 23
Figure 23
Structures of alkylpurines 108–110.
Figure 24
Figure 24
Structures of purines 111–115.
Figure 25
Figure 25
Structures of alkylpurines 116–121.
Figure 26
Figure 26
Structures of alkylpurines 122–129.
Figure 27
Figure 27
Structures of spongosine and doridosine.
Figure 28
Figure 28
Structures of cyclonucleosides 132 and 133.
Figure 29
Figure 29
Structures of momusines 134–137.
Figure 30
Figure 30
Structures of hamiguanosinol and salvadenosine.
Figure 31
Figure 31
Structures of nucleosides 140–143.
Scheme 1
Scheme 1
A general synthetic procedure towards 7-alkylpurines.
Scheme 2
Scheme 2
Molinski’s synthesis of acremolin, 122 [91].
Scheme 3
Scheme 3
Fujii’s synthesis of caissarone, 28, [120] and Itaya’s synthesis of aplidiamine, 113 [83].
Scheme 4
Scheme 4
General retrosynthetic strategy for the synthesis of diterpenyladeninium derivatives.
Scheme 5
Scheme 5
Gundersen’s synthesis of malonganenone J, 43 [131].
Figure 32
Figure 32
Structures of natural diterpenoids used in the synthesis of diterpenylpurines.
Scheme 6
Scheme 6
Terpenylpurines obtained from trans-communic and cupressic acids and monoterpenes.
Scheme 7
Scheme 7
Retrosynthetic schemes for asmarines.
Scheme 8
Scheme 8
Synthesis of an advanced analogue of asmarine A by Shenvi [142].
Scheme 9
Scheme 9
Molinski’s synthesis of salvadenosine, 139 [110].
Scheme 10
Scheme 10
Molinski’s synthesis of hamiguanosinol, 138 [110].
Scheme 11
Scheme 11
Synthesis of trachycladines A and B by Wu [143].
Scheme 12
Scheme 12
Synthesis of trachycladines A and B and analogues by Koumbis [144,145].
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