Charting Angiosperm Chemistry: Evolutionary Perspective on Specialized Metabolites Reflected in Chemical Property Space

Abstract

Plants possess an outstanding chemical diversity of specialized metabolites developed to adapt to environmental niches and increase fitness. The observed diversity is hypothesized to result from various evolutionary mechanisms, such as the continuous branching off and extension of existing biosynthetic pathways or enhanced levels of catalytic promiscuity in certain enzymes. In this study, ChemGPS-NP has been employed to chart the distribution and diversity of physicochemical properties for selected types of specialized metabolites from the angiosperms. Utilizing these charts, it is analyzed how different properties of various types of specialized metabolites change in different plant groups, and the chemical diversity from the volume they occupy in chemical property space is evaluated. In this context, possible underlying evolutionary mechanisms are discussed, which could explain the observed distribution and behavior in chemical property space. Based on these studies, it is demonstrated that evolutionary processes in plant specialized metabolism and the resultant metabolic diversification are reflected in chemical property space.

Unraveling Plant Natural Chemical Diversity for Drug Discovery Purposes

“…Statistical analyses have been performed on natural products to study their chemical diversity (Firn and Jones, 2003;Hong, 2011), molecular properties (Feher and Schmidt, 2003;Quinn et al, 2008), scaffold diversity (Lee and Schneider, 2001;Grabowski et al, 2008;Yongye et al, 2012), and coverage of the chemical space (Rosén et al, 2009a). Comparisons between NP and other compound collections (Henkel et al, 1999;Lee and Schneider, 2001;Grabowski and Schneider, 2007;Rosén et al, 2009a) have also been performed, showing that NP differ from drugs and synthetic compounds in several aspects. NP are considered complex due to their number of asymmetric centers, their number of Sp3 carbon ratio in rings, and their number of ring junctions.…”

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“…Advances in nuclear magnetic resonance (NMR) spectroscopy include the Metabolomics and Dereplication by Two‐dimensional Experiments (MADByTE) tool, which leverages heteronuclear single quantum coherence (HSQC) spectroscopy and total correlated spectroscopy (TOCSY) data to construct spin systems of a compound, and uses these features to generate association networks for analyses (Egan & Linington, 2019). In addition to applications of these new analytical techniques in drug discovery initiatives, exploration of plant metabolite diversity has also proven useful to phylogenetic and evolutionary studies within genera and across larger groups of angiosperms (Ernst et al., 2019; Henz Ryen & Backlund, 2019). Beyond advances in mass spectrometry and nuclear magnetic resonance, emerging technologies that unite the strengths of X‐ray crystallography with electron microscopy are enabling crystal structures of tiny quantities of certain natural products in mixtures to be determined.…”

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