Evolution and current status of ecological phytochemistry

Macías, Francisco A.; Galindo, José; Galindo, Juan C. G.

doi:10.1016/j.phytochem.2007.10.010

Cited by 55 publications

(30 citation statements)

References 108 publications

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“…The vast structural diversity in plant secondary metabolites is considered to be the consequence of chemical adaptation by plants to specific ecological niches, since plants exploit secondary metabolites in defense responses against pathogens, and in symbiotic relationships, such as nitrogen fixation and pollinator attraction (Gershenzon and Dudareva, 2007;Macías et al, 2007). A particular plant lineage develops specialized metabolites by acquisition of novel functions of biosynthetic enzymes to increase fitness to its environment.…”

Section: Introductionmentioning

confidence: 99%

Local Differentiation of Sugar Donor Specificity of Flavonoid Glycosyltransferase in Lamiales

et al. 2009

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Flavonoids are most commonly conjugated with various sugar moieties by UDP-sugar:glycosyltransferases (UGTs) in a lineage-specific manner. Generally, the phylogenetics and regiospecificity of flavonoid UGTs are correlated, indicating that the regiospecificity of UGT differentiated prior to speciation. By contrast, it is unclear how the sugar donor specificity of UGTs evolved. Here, we report the biochemical, homology-modeled, and phylogenetic characterization of flavonoid 7-Oglucuronosyltransferases (F7GAT), which is responsible for producing specialized metabolites in Lamiales plants. All of the Lamiales F7GATs were found to be members of the UGT88-related cluster and specifically used UDP-glucuronic acid (UDPGA). We identified an Arg residue that is specifically conserved in the PSPG box in the Lamiales F7GATs. Substitution of this Arg with Trp was sufficient to convert the sugar donor specificity of the Lamiales F7GATs from UDPGA to UDPglucose. Homology modeling of the Lamiales F7GAT suggested that the Arg residue plays a critical role in the specific recognition of anionic carboxylate of the glucuronic acid moiety of UDPGA with its cationic guanidinium moiety. These results support the hypothesis that differentiation of sugar donor specificity of UGTs occurred locally, in specific plant lineages, after establishment of general regiospecificity for the sugar acceptor. Thus, the plasticity of sugar donor specificity explains, in part, the extraordinary structural diversification of phytochemicals.

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Section: Introductionmentioning

confidence: 99%

Local Differentiation of Sugar Donor Specificity of Flavonoid Glycosyltransferase in Lamiales

et al. 2009

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“…Santos (2009) (Santos et al, 2009). L'activité allélopathique des dérivés de lupane (lupéol, acide bétulinique, bétulonal 2, bétuline et messagénine) a été rapportée dans le travail de Macias (Macias et al, 2007). Ces triterpènes possédaient potentiellement une activité allélopathique en particulier sur les espèces dicotylédones.…”

Section: Résultats Et Discussionunclassified

Détermination structurale de triterpenoïdes isolés des feuilles de <i>Combretum glutinosium</i> Perr. Ex DC (Combretaceae)

N’diaye¹,

Mbaye²,

Gassama³

et al. 2017

Int. J. Bio. Chem. Sci

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Structural determination of triterpenoids isolated from leaves combretum glutinosum Perr. Ex DC (Combretaceae)ABSTRACT Combretum glutinosum Perr.Ex DC is a plant of the Senegal traditional pharmacopoeia whose leaves are used in the treatment I of various diseases. Four triterpenoids betulinol 1, betulonal 2, betulonic acid 3 and cabraleone 4 were isolated from the hexane and dichloromethane extracts of the leaves. Isolation and characterization of this compounds were respectively done by chromatography on silica gel and by NMR (1D, 2D) and ESI-MS spectral analysis. This work allowed us to confirm the ethnopharmacological studies carried out on this plant.

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“…As isoflavones are precursors for these protective compounds (phytoalexins), the differences in the total amounts could influence in the disease susceptibility. Disease sensitive and resistant plant genotypes may be characterized, among other traits, by their response time: those plants that are able to synthesize phytoalexins faster will be able to control the disease in the early stages (Macias et al, 2007). Ohberg et al (2005) found differences in disease resistance between the early and late types of Swedish red clover cultivars, with the late types showing more resistance to Sclerotinia trifoliorum (Clover Rot) than the earlier ones.…”

Section: Genetic Diversity For Isoflavones and Cluster Analysismentioning

confidence: 99%

Genetic variability of isoflavones in the USDA red clover core collection

Ramos¹,

Dias²,

Morais³

et al. 2012

Rev. bras. farmacogn.

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Abstract:Red clover is one of the most utilized forage in agriculture and contains many of the isoflavones known for their human health benefits. The objectives of this study were: i) to quantify, using HPLC analysis, isoflavones in 77 accessions from the USDA core collection and a Brazilian line; ii) to verify possible relationships depending on their origin, improvement status or maturity type and; iii) to verify the seasonal variation. The isoflavone mean contents were 29.27 µg g -1 of dry material for daidzein, 163.69 µg g -1 for genistein, 11353.29 µg g -1 for formononetin and 6568.8 µg g -1 for biochanin A. Clustering was mainly influenced by the total amount of isoflavones and partially due to maturity type, improvement status and geographic origin. The seasonal evaluation demonstrated an increase of concentration during winter, and decrease during spring. These results highlighted accessions that can be used to develop new varieties with low or high isoflavones concentration.

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Evolution and current status of ecological phytochemistry

Cited by 55 publications

References 108 publications

Local Differentiation of Sugar Donor Specificity of Flavonoid Glycosyltransferase in Lamiales

Local Differentiation of Sugar Donor Specificity of Flavonoid Glycosyltransferase in Lamiales

Détermination structurale de triterpenoïdes isolés des feuilles de <i>Combretum glutinosium</i> Perr. Ex DC (Combretaceae)

Genetic variability of isoflavones in the USDA red clover core collection

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