A Phylogenetic Analysis of Tribes of the Asteraceae Based on Phytochemical Data

Calabria, Lalita M.; Emerenciano, Vicente P.; Ferreira, Marcelo J. P.; Scotti, Marcus T.; Mabry, Tom J.

doi:10.1177/1934578x0700200310

Cited by 11 publications

(8 citation statements)

References 26 publications

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“…In the Chemistry of Natural Products, secondary metabolites are important chemotaxonomic markers [ 20 , 21 ]. Chemosystematics consists of classifying organisms through chemical characteristics, thus providing some answers and/or proposals for a greater understanding of evolution [ 22 , 23 , 24 , 25 ]. Some chemosystematics studies tried to relate the oxidation of secondary metabolites with the phytochemical evolution and diversity based on that oxidative pathways in plants occur parallel to protective mechanisms against oxidative degradation [ 23 , 25 ].…”

Section: Introductionmentioning

confidence: 99%

Self-Organizing Maps of Molecular Descriptors for Sesquiterpene Lactones and Their Application to the Chemotaxonomy of the Asteraceae Family

et al. 2012

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The Asteraceae, one of the largest families among angiosperms, is chemically characterised by the production of sesquiterpene lactones (SLs). A total of 1,111 SLs, which were extracted from 658 species, 161 genera, 63 subtribes and 15 tribes of Asteraceae, were represented and registered in two dimensions in the SISTEMATX, an in-house software system, and were associated with their botanical sources. The respective 11 block of descriptors: Constitutional, Functional groups, BCUT, Atom-centred, 2D autocorrelations, Topological, Geometrical, RDF, 3D-MoRSE, GETAWAY and WHIM were used as input data to separate the botanical occurrences through self-organising maps. Maps that were generated with each descriptor divided the Asteraceae tribes, with total index values between 66.7% and 83.6%. The analysis of the results shows evident similarities among the Heliantheae, Helenieae and Eupatorieae tribes as well as between the Anthemideae and Inuleae tribes. Those observations are in agreement with systematic classifications that were proposed by Bremer, which use mainly morphological and molecular data, therefore chemical markers partially corroborate with these classifications. The results demonstrate that the atom-centred and RDF descriptors can be used as a tool for taxonomic classification in low hierarchical levels, such as tribes. Descriptors obtained through fragments or by the two-dimensional representation of the SL structures were sufficient to obtain significant results, and better results were not achieved by using descriptors derived from three-dimensional representations of SLs. Such models based on physico-chemical properties can project new design SLs, similar structures from literature or even unreported structures in two-dimensional chemical space. Therefore, the generated SOMs can predict the most probable tribe where a biologically active molecule can be found according Bremer classification.

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Section: Introductionmentioning

confidence: 99%

Self-Organizing Maps of Molecular Descriptors for Sesquiterpene Lactones and Their Application to the Chemotaxonomy of the Asteraceae Family

et al. 2012

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“…From the above, it can be surmised that secondary metabolites are diverse and, in some cases, are unique to specific plant species and, as such, can be used as chemotaxonomic markers [ 15 – 18 ]. Therefore, the unambiguous detection and identification of these metabolites using analytical techniques such as liquid chromatography-mass spectrometry (LC-MS) is of paramount importance.…”

Section: Introductionmentioning

confidence: 99%

Synchronized Survey Scan Approach Allows for Efficient Discrimination of Isomeric and Isobaric Compounds during LC-MS/MS Analyses

Masike

Madala

2018

Journal of Analytical Methods in Chemistry

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Liquid chromatography-mass spectrometry- (LC-MS-) based multiple reaction monitoring (MRM) methods have been used to detect and quantify metabolites for years. These approaches rely on the monitoring of various fragmentation pathways of multiple precursors and the subsequent corresponding product ions. However, MRM methods are incapable of confidently discriminating between isomeric and isobaric molecules and, as such, the development of methods capable of overcoming this challenge has become imperative. Due to increasing scanning rates of recent MS instruments, it is now possible to operate MS instruments both in the static and dynamic modes. One such method is known as synchronized survey scan (SSS), which is capable of acquiring a product ion scan (PIS) during MRM analysis. The current study shows, for the first time, the use of SSS-based PIS approach as a feasible identification feature of MRM. To achieve the above, five positional isomers of dicaffeoylquinic acids (diCQAs) were studied with the aid of SSS-based PIS method. Here, the MRM transitions were automatically optimized using a 3,5-diCQA isomer by monitoring fragmentation transitions common to all five isomers. Using the mixture of these isomers, fragmentation spectra of the five isomers achieved with SSS-based PIS were used to identify each isomer based on previously published hierarchical fragmentation keys. The optimized method was also used to detect and distinguish between diCQA components found in Bidens pilosa and their isobaric counterparts found in Moringa oleifera plants. Thus, the method was shown to distinguish (by differences in fragmentation patterns) between diCQA and their isobars, caffeoylquinic acid (CQA) glycosides. In conclusion, SSS allowed the detection and discrimination of isomeric and isobaric compounds in a single chromatographic run by producing a PIS spectrum, triggered in the automatic MS/MS synchronized survey scan mode.

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“…The secondary metabolite chemistry of Barnadesioideae has been sometimes described as following a simple profile (BOHM and STUESSY 1995;ZDERO et al 1987). This possible simple chemistry profile was proposed and hypothesized as further evidence of the basal position of Barnadesioideae in the Asteraceae family (BOHM and STUESSY 1995;BOHM and STUESSY 2001;CALABRIA et al 2007). In total, two acetophenones (1 and 2) (SENATORE 1996;SENATORE et al 1999), vanillin (3) (HOENEISEN et al 2000), gallic (CASTELUCCI et al 2007), umbelliferone (5) (HOENEISEN et al 2000), 13 flavonoids (kaempferol, quercetin, isorhammetin, and their 3-O-glycosides, 6-18) (BOHM and STUESSY 1995;MENDIONDO et al 1997MENDIONDO et al , 2000SENATORE et al 1999;MENDIONDO and JUÁREZ 2001;JUAREZ and MENDIONDO 2002a, 2002bLANDA et al 2009), and 21 triterpenoids (taraxastane-, lupane-, ursane-and oleanane-type pentacyclic triterpenoids, 19-39) (ZDERO et al 1987;FLAGG et al 1999;HOENEISEN et al 2000;GUROVIC et al 2010) have been described to date in Barnadesioideae.…”

Section: Chemistrymentioning

confidence: 85%

Estudos metabolômicos da subfamília Barnadesioideae (Asteraceae)

Ccana-Ccapatinta¹

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Metabolomics is emerging as an effective approach for the comprehensive evaluation of medicinal plants, classification of raw material, as well as chemotaxonomic studies. This work demonstrates the applicability of metabolomics, using the subfamily Barnadesioideae (Asteraceae) as a study model, for quality assessment and classification purposes of medicinal species (Chuquiraga genus) and a chemotaxonomy study of six Barnadesioideae genera (Arnaldoa, Barnadesia, Chuquiraga, Dasyphyllum, Fulcaldea and Schlechtendalia). First, the LC-MS metabolic profiles of Barnadesioideae demonstrated that this subfamily constitutes a chemically underinvestigated taxa with a complex diversity of phenolic compounds, phenylpropanoid derivatives, alkyl glycosides, and triterpenoid glycosides. The intergeneric relationships within Barnadesioideae genera, based on the comparison of their LC-MS metabolic profiles by exploratory and supervised analyses, displayed similarities to those of the intergeneric relationships obtained by the most recent phylogenetic study based on morphological and molecular markers. Second, the LC-MS metabolic profiles of three Chuquiraga species (C. jussieui, C. spinosa and C. weberbaueri) lead to the identification of a significant variety of phenolic compounds, phenylpropanoid derivatives, alkyl glycosides, and triterpenoid glycosides, as well as the establishment of prediction models for geographical origin and species classification, as well as the identification of discriminating metabolites by exploratory and supervised multivariate statistical analysis. Third, a classical approach was carried out by acquiring HPLC chromatographic profiles of three Chuquiraga species (C. jussieui, C. spinosa and C. weberbaueri) for profiling phenolic compounds and comparison by exploratory and supervised multivariate statistical analysis. Therefore, our results support metabolomics as a valuable tool in the quality control and classification of medicinal plants as well as in chemotaxonomy studies.

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A Phylogenetic Analysis of Tribes of the Asteraceae Based on Phytochemical Data

Cited by 11 publications

References 26 publications

Self-Organizing Maps of Molecular Descriptors for Sesquiterpene Lactones and Their Application to the Chemotaxonomy of the Asteraceae Family

Self-Organizing Maps of Molecular Descriptors for Sesquiterpene Lactones and Their Application to the Chemotaxonomy of the Asteraceae Family

Synchronized Survey Scan Approach Allows for Efficient Discrimination of Isomeric and Isobaric Compounds during LC-MS/MS Analyses

Estudos metabolômicos da subfamília Barnadesioideae (Asteraceae)

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