Abstract

The Melastomataceae family, the seventh largest flowering plants, has been studied in several fronts of natural product chemistry, including terpenoids, simple phenolics, flavonoids, quinones, lignans and their glycosides, as well as a vast range of tannins or polyphenols. This review concerns the phenolic and polyphenolic metabolites described in the literature for several genera of this family, the mode of isolation and purification, and the structure elucidation of these new natural products that has been achieved by extensive spectral analyses, including ESI-MS, 1H-, 13C-NMR spectra and two-dimensional experiments, COSY, TOCSY, J-resolved, NOESY, HMQC, DEPT, and HMBC, as well as chemical and enzymatic degradations and the chemotaxonomic meaning. Finally, a general biogenetic pathway map for ellagitannins is proposed on the bases of the most plausible free radical C-O oxidative coupling.

Highlights

  • The Melastomataceae Jussieu is a large family of ca. 166 genera and 4200–4500 species that exhibit a diversity of growth habitats, including herbs, shrubs, treelets, climbers, and trees up to 30–45 m high; Molecules 2015, 20 the last are concentrated in the Merianieae and Miconieae tribes

  • Most of the reported chemical constituents from the Melastomataceous plants belong to polyphenolic compounds; some triterpenoids and alkyl benzoquinones [8,9,10,11] have been described

  • A report of anthocyanins and anthocyanidins in different Melastomataceae varieties showed the presence of malvidin glycosides in the flowers (19d, 19e, 19f) and mainly delphinidin and pelargonidin glycosides in the fruits

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Summary

Introduction

The Melastomataceae Jussieu is a large family of ca. 166 genera and 4200–4500 species that exhibit a diversity of growth habitats, including herbs, shrubs, treelets, climbers, and trees up to 30–45 m high; Molecules 2015, 20 the last are concentrated in the Merianieae and Miconieae tribes. 166 genera and 4200–4500 species that exhibit a diversity of growth habitats, including herbs, shrubs, treelets, climbers, and trees up to 30–45 m high; Molecules 2015, 20 the last are concentrated in the Merianieae and Miconieae tribes. They can be recognized among dicotyledoneous by their leaves which have a characteristic acrodromous venation. This review concerns the phenolic and polyphenolic metabolites described in the literature for several genera of this family, the mode of isolation and purification, and the structure elucidation of these new natural products that has been achieved by extensive spectral analyses, including ESI-MS, 1H-, C-NMR spectra and two-dimensional (2D) experiments, COSY, TOCSY, J-resolved, NOESY, HSQC, DEPT, and HMBC, as well as chemical and enzymatic degradations. The taxonomy and folk medicinal uses of Melastomataceae plants are described in Table S1 in the Supplementary File

Chemical Constituents of Melastomataceous Plants
Triterpenoids and Alkyl Benzoquinones
Flavonoids
Anthocyanins and Anthocyanidins
Phenolic Acids and Derivatives
Galloylated Cyanogenic Glucosides and Benzyl Glycosides
Hydrolyzable Tannins
Galloyl Glycosides
Ellagitannins
Biogenesis of Ellagitannins in Melastomataceous Plants
Condensed Tannins
Conclusions
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