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Improved Synthesis of Analogues of Red Wine Pyranoanthocyanin Pigments.

ABSTRACT: An improved procedure is described for the preparation of pyranoflavylium cations from the reaction of 5,7-dihydroxy-4-methylflavylium cation with aromatic aldehydes. Modifications of the procedure of Chassaing et al. (Tetrahedron Lett. 2008, 49, 6999-7004; Tetrahedron 2015, 71, 3066-3078) circumvent the reported restriction to electron-rich benzaldehydes and provide access to a wide variety of substituted pyranoflavylium cations, including those with electron-withdrawing substituents or an attached heterocyclic or polycyclic aromatic ring. This opens the way for studies of substituent and structural effects on the ground and excited states of these pyranoanthocyanin analogues, the behavior of which should mirror fundamental aspects of the chemistry and photophysics of the pyranoanthocyanin chromophores present in mature red wines.

SUBMITTER: da Silva CP

PROVIDER: S-EPMC6641511 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Improved Synthesis of Analogues of Red Wine Pyranoanthocyanin Pigments.

da Silva Cassio Pacheco CP Pioli Renan Moraes RM Liu Liu L Zheng Shasha S Zhang Mengjiao M Silva Gustavo Thalmer de Medeiros GTM Carneiro Vânia Maria Teixeira VMT Quina Frank H FH

ACS omega 20180125 1

An improved procedure is described for the preparation of pyranoflavylium cations from the reaction of 5,7-dihydroxy-4-methylflavylium cation with aromatic aldehydes. Modifications of the procedure of Chassaing et al. (Tetrahedron Lett. 2008, 49, 6999-7004; Tetrahedron 2015, 71, 3066-3078) circumvent the reported restriction to electron-rich benzaldehydes and provide access to a wide variety of substituted pyranoflavylium cations, including those with el ...[more]

PMID: 31457941

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Project description:Twelve species of Hypomyces/Cladobotryum producing red pigments are reported growing in various tropical areas of the world. Ten of these are described as new, including teleomorphs for two previously known anamorphic species. In two species the teleomorph has been found in nature and in three others it was obtained in culture; only anamorphs are known for the rest. None of the studied tropical collections belongs to the common temperate species H. rosellus and H. odoratus to which the tropical teleomorphic collections had previously been assigned. Instead, taxa encountered in the tropics are genetically and morphologically distinct from the nine species of Hypomyces/Cladobotryum producing red pigments known from temperate regions. Besides observed host preferences, anamorphs of several species can spread fast on soft ephemeral agaricoid basidiomata but the slower developing teleomorphs are mostly found on polyporoid basidiomata or bark. While a majority of previous records from the tropics involve collections from Central America, this paper also reports the diversity of these fungi in the Paleotropics. Africa appears to hold a variety of taxa as five of the new species include material collected in scattered localities of this mostly unexplored continent. In examining distribution patterns, most of the taxa do not appear to be pantropical. Some species are known only from the Western Hemisphere, while others have a geographic range from southeastern Asia to Africa or Australia. The use of various morphological characters of anamorphs and teleomorphs as well as culture characteristics in species delimitation is evaluated. For detecting genetic segregation, partial sequences of the two largest subunits of the ribosomal polymerase perform the best in terms of providing informative sites and the number of well-supported groups recognised in the phylogenies. These are followed by the sequence data of the translation-elongation factor 1-alpha, while the ribosomal DNA ITS regions are of only limited use in distinguishing species and their phylogenetic relationships.

Dataset Information

Improved Synthesis of Analogues of Red Wine Pyranoanthocyanin Pigments.

Publications

Improved Synthesis of Analogues of Red Wine Pyranoanthocyanin Pigments.

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