Abstract

The Annonaceae family of plants is one of the most anatomically and structurally uniform families. Chemotaxonomy is a common practice to determine the chemical patterns within these families at different phylogenetic levels. The aim of this study was to build a dataset of all the secondary metabolites isolated within the Annonaceae family and to perform the respective chemotaxonomic analysis using self-organizing maps (SOMs). This dataset is composed of 5321 botanical occurrences and 1860 unique molecules present in all subfamilies of the Annonaceae. Diterpenes account for 366 unique compounds and 533 botanical occurrences seen in both Annonoideae and Malmeoideae subfamilies. The Annoneae, Xylopieae and Miliuseae tribes had the highest number of botanical occurrences and were therefore selected for the analysis. Molecular descriptors of the diterpenes and their respective botanical occurrences were used to generate the SOMs. These SOMs demonstrated clear and indicative tribe separations, with a match rate higher than 70%. Our results corroborate with the morphological and molecular data. These models can be used to predict the phylogenetic location of certain diterpenes and to accelerate the research of Annonaceae secondary metabolites and their biological potentials.

Highlights

  • The Annonaceae family was first described by Antoine Laurent de Jussieu in 1789 and is known for its striking anatomical and structural uniformity

  • We collected and processed all Web of Science-indexed research papers published between 1970 and 2019 to create a database of secondary metabolites isolated from Annonaceae, except for the acetogenin class that is exclusive to this family

  • One explanation for this growth is the abundant and diverse biological activity of the Annonaceae that comes from the structural diversity of the secondary metabolites

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Summary

Introduction

The Annonaceae family was first described by Antoine Laurent de Jussieu in 1789 and is known for its striking anatomical and structural uniformity. The family is very consistent morphologically, with a unique primitive group of angiosperms providing easy identification.[1,2,3,4]. Two recent studies relevantly discuss the phylogenetic classification of the Annonaceae family. The first study carried out by Chatrou et al.[5] used eight plastid markers and representatives of 94 genera to formally and scientifically classify the Annonaceae into four subfamilies: Anaxagoreoideae, Ambavioideae, Annonoideae and Malmeoideae. The two largest subfamilies, Annonoideae and Malmeoideae, were divided into 14 tribes. The second study was conducted by Guo et al.,[6] and considered the phylogenetics of the Annonaceae based on a super matrix

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