Chemical characterization of two morphologically related Espeletia (Asteraceae) species and chemometric analysis based on essential oil components

Padilla-González, Guillermo F.; Aldana, Jennyfer Andrea; Costa, Fernando B. Da

doi:10.1016/j.bjp.2016.05.009

Cited by 14 publications

(11 citation statements)

References 22 publications

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“…Percentage compositions of the essential oil components were used as input data to perform a hierarchical clustering analysis (HCAbp) with bootstrap resampling in the software R 3.4.1 (R Foundation for Statistical Computing, Vienna, Austria), using the pvclust [65] package, the ward's clustering algorithm and Euclidean distance. Prior to multivariate analyses, raw data were scaled by the arcsine method in accordance with previous reports for data expressed as percentages [66,67]. Two types of support values were plotted in the HCAbp using 10,000 replicates: traditional bootstrapping (bp) and approximately unbiased (au) p-values.…”

Section: Multivariate Analysismentioning

confidence: 99%

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The Diversity of Volatile Compounds in Australia’s Semi-Desert Genus Eremophila (Scrophulariaceae)

Sadgrove

Padilla-González

Green

et al. 2021

Plants

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Australia’s endemic desert shrubs are commonly aromatic, with chemically diverse terpenes and phenylpropanoids in their headspace profiles. Species from the genus Eremophila (Scrophulariaceae ex. Myoporaceae) are the most common, with 215 recognised taxa and many more that have not yet been described, widely spread across the arid parts of the Australian continent. Over the years, our research team has collected multiple specimens as part of a survey to investigate the chemical diversity of the genus and create leads for further scientific enquiry. In the current study, the diversity of volatile compounds is studied using hydrodistilled essential oils and leaf solvent extracts from 30 taxa. Several rare terpenes and iridoids were detected in chemical profiles widely across the genus, and three previously undescribed sesquiterpenes were isolated and are assigned by 2D NMR—E-11(12)-dehydroisodendrolasin, Z-11-hydroxyisodendrolasin and 10-hydroxydihydro-α-humulene acetate. Multiple sampling from Eremophila longifolia, Eremophila arbuscular, Eremophila latrobei, Eremophila deserti, Eremophila sturtii, Eremophila oppositifolia and Eremophila alternifolia coneys that species in Eremophila are highly chemovariable. However, taxa are generally grouped according to the expression of (1) furanosesquiterpenes, (2) iridoids or oxides, (3) mixtures of 1 and 2, (4) phenylpropanoids, (5) non-furanoid terpenes, (6) mixtures of 4 and 5, and less commonly (7) mixtures of 1 and 5. Furthermore, GC–MS analysis of solvent-extracted leaves taken from cultivated specimens conveys that many heavier ‘volatiles’ with lower vapour pressure are not detected in hydrodistilled essential oils and have therefore been neglected in past chemical studies. Hence, our data reiterate that chemical studies of the genus Eremophila will continue to describe new metabolites and that taxon determination has limited predictive value for the chemical composition.

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Section: Multivariate Analysismentioning

confidence: 99%

“…A principal component analysis (PCA) was performed using the prcomp function and the factoextra package in the software R. Prior to PCA, raw data were scaled by the arcsine method in accordance with previous reports for data expressed as percentages [66,67].…”

Section: Multivariate Analysismentioning

confidence: 99%

The Diversity of Volatile Compounds in Australia’s Semi-Desert Genus Eremophila (Scrophulariaceae)

Sadgrove

Padilla-González

Green

et al. 2021

Plants

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“…Peaks detected in the last 5 min of the chromatographic run (equilibration stage) were excluded from the analyses. Considering that the subtribe Espeletiinae is especially rich in phenolic compounds [ 40 , 57 , 58 ], which also represents the main class of metabolites correlated with the biogeographic segregation of Espeletia [ 38 ], the negative ionization mode was selected for further preprocessing steps. These data were processed by MZmine 2.21 [ 59 ] to perform peak detection, peak filtering, chromatogram construction, chromatogram deconvolution, isotopic peak grouping, chromatogram alignment, gap filling, duplicate peaks filter, fragment search, and the search for adducts and peak identities using an in-house chemical structure database (see below).…”

Section: Methodsmentioning

confidence: 99%

Effect of the Andean Geography and Climate on the Specialized Metabolism of Its Vegetation: The Subtribe Espeletiinae (Asteraceae) as a Case Example

2021

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The Andean mountains are ‘center stage’ to some of the most spectacular examples of plant diversifications, where geographic isolation and past climatic fluctuations have played a major role. However, the influence of Andean geography and climate as drivers of metabolic variation in Andean plants is poorly elucidated. Here, we studied the influence of those factors on the metabolome of the subtribe Espeletiinae (Asteraceae) using liquid chromatography coupled to high-resolution mass spectrometry data of over two hundred samples from multiple locations. Our results demonstrate that metabolic profiles can discriminate Espeletiinae taxa at different geographic scales, revealing inter- and intraspecific metabolic variations: at the country level, segregation between Colombian and Venezuelan taxa was observed; regionally, between páramo massifs; and locally, between páramo complexes. Metabolic differences in Espeletiinae were mainly explained by geographic isolation, although differences in taxonomic genera, temperature, and elevation, were also important. Furthermore, we found that different species inhabiting the same páramo complex showed stronger chemical similarities than the same species at different locations, corroborating that geographic isolation represents the main driver of metabolic change in Espeletiinae. The current study serves as a starting point to fill in the gaps in how Andean geography and climate have shaped the metabolism of its vegetation and reveal the potential of untargeted metabolomics to study the environmental physiology of plants.

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“…Percentage compositions of the essential oil components were used as input data to perform a hierarchical clustering analysis (HCAbp) with bootstrap resampling in the software R 3.4.1 (R Foundation for Statistical Computing, Vienna, Austria), using the pvclust [ 22 ] package, the ward’s clustering algorithm and Euclidean distance. Prior to multivariate analyses, raw data were scaled by the arcsine method in accordance with previous reports for data expressed as percentages [ 23 , 24 ]. Two types of support values were plotted in the HCAbp using 10,000 replicates: traditional bootstrapping (bp) and approximately unbiased (au) p -values.…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Prostanthera (Lamiaceae) as a ‘Cradle of Incense’: Chemophenetics of Rare Essential Oils from Both New and Forgotten Australian ‘Mint Bush’ Species

Sadgrove

Padilla-González

Telford

et al. 2020

Plants

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The highly aromatic Australian mint bushes from the genus Prostanthera Labill. produce a high yield of essential oil on hydrodistillation. Together with its rich history, horticultural potential, iconic flowers, and aromatic leaves, it achieves high ornamental and culinary value. Species in the genus express highly diverse and chemically unique essential oils that demonstrate intra- and inter-specific patterns that have inspired taxonomic reinterpretation for over a hundred years. Previous studies have conveyed that phenoplastic expression of volatiles creates chemotypes within taxa, adding complexity to chemophenetic exploration. The current study chemically characterised essential oils from 64 highly aromatic specimens, representative of 25 taxa, giving yields as high as >2% g/g. The chemical profiles of essential oils are diverse, but generally include 1,8-cineole and signatory compounds such as sesquiterpene oxides, caryophyllene oxide, kessane and cis-dihydroagarofuran; sesquiterpene alcohols, globulol, epiglobulol, maaliol, prostantherol, spathulenol and ledol; and monoterpene derivatives of common scaffolds, borneol, bornyl acetate, bornanone, linalool and linalyl acetate. As in previous studies, analysis of chemical data confirms that the chemistry strongly agrees with taxonomic classifications. Importantly, as in classical taxonomy, the current chemical study complemented morphological analysis but conveys chemovariation, obscuring the taxonomic agreement. Nevertheless, variation within taxa may be due to environmental factors, meaning that cultivation of species in gardens will create different chemical profiles as compared to those published here.

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Chemical characterization of two morphologically related Espeletia (Asteraceae) species and chemometric analysis based on essential oil components

Cited by 14 publications

References 22 publications

The Diversity of Volatile Compounds in Australia’s Semi-Desert Genus Eremophila (Scrophulariaceae)

The Diversity of Volatile Compounds in Australia’s Semi-Desert Genus Eremophila (Scrophulariaceae)

Effect of the Andean Geography and Climate on the Specialized Metabolism of Its Vegetation: The Subtribe Espeletiinae (Asteraceae) as a Case Example

Prostanthera (Lamiaceae) as a ‘Cradle of Incense’: Chemophenetics of Rare Essential Oils from Both New and Forgotten Australian ‘Mint Bush’ Species

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