Caffeic Acid Derivatives from Eupatorium perfoliatum L.

Maas, M.Sc Dr.Ir. Azwar; Petereit, Frank; Hensel, Andreas

doi:10.3390/molecules14010036

Cited by 45 publications

(36 citation statements)

References 30 publications

(35 reference statements)

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“…1B). The structures of known compounds were determined by comparing their spectroscopic and/or chromatographic data with values in the literature and were identified as 3-O-[(trans)-caffeoyl]-glucaric acid (A) (Maas et al, 2009;Nagels et al, 1982), 2-O-[(trans)-caffeoyl]-glucaric acid (B-1) (Strack et al, 1987), 5-O-[(trans)-caffeoyl]-quinic acid (neo-chlorogenic acid)…”

Section: Discussionmentioning

confidence: 99%

Identification of Flavonoids in Leaves of a Labile Bicolor Flowering Dahlia (<i>Dahlia variabilis</i>) ‘Yuino’

et al. 2018

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Bicolor flowering dahlias are a group of cultivars that produce inflorescences with bicolored petals characterized by a colored basal part and a white tip. However, they frequently produce single-colored petals, even if they are vegetatively propagated. In a previous study, strong relationships between inflorescence color and leaf phenotype were observed in a red-white bicolor flowering dahlia 'Yuino'; red petal-producing individuals accumulate flavonoids in leaves, whereas only bicolor petal-producing individuals tend not to accumulate them in leaves. Flavonoids in leaves are assumed to be chalcones. In this study, we investigated flavonoids in the leaves of 'Yuino' by nuclear magnetic resonance analysis and identified six caffeoyl esters, four flavonol derivatives, and three novel butein derivatives in the flavonoid-rich leaves of 'Yuino'. The three novel compounds were butein 4',4-O-di-[2-O-(β-glucopyranosyl)-β-glucopyranoside], butein 4'-O-[2-O-(β-glucopyranosyl)-β-glucopyranoside]-4-O-β-glucopyranoside, and butein 4'-[6-O-(3-hydroxy-3-methylglutaryl)-β-glucopyranoside]-4-O-β-glucopyranoside.On the other hand, only caffeoyl esters were detected in flavonoidpoor leaves. These data demonstrated that flavonoid-rich leaves accumulated the flavonoids of butein and flavonol derivatives. The common enzyme for the biosynthesis of butein and flavonol derivatives is chalcone synthase; thus, the importance of chalcone synthase for phenotypic lability in 'Yuino' was confirmed.

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Section: Discussionmentioning

confidence: 99%

Identification of Flavonoids in Leaves of a Labile Bicolor Flowering Dahlia (<i>Dahlia variabilis</i>) ‘Yuino’

et al. 2018

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“…The presence of this rare type of compounds was not reported in Inula sp. before, although the presence of di-tri-and tetracaffeoylglucaric acid derivatives was demonstrated in other genera of Asteroideae subfamily such as Leontopodium, Gnaphalium and Eupatorium (Schwaiger et al 2005;Maas et al 2009;Cicek et al 2012). Jaiswal et al (2011) identified six hydroxycinnamic acid derivatives in the extract from aerial parts of I. helenium, including three monocaffeoylquinic acids (1-O-, 3-O-, and 5-O-CQA), 5-O-feruloylquinic acid, 5-O-p-coumaroylquinic acid, and 3-Ocaffeoyl-4-O-p-coumaroylquinic acid.…”

Section: Resultsmentioning

confidence: 94%

“…Peaks 4, 6-8, 12 and 14-16 showed a cleavage of two to four caffeoyl [M -H-162] -moieties resulting in m/z 209 fragment (Table 1), indicating the presence of glucaric acid or galactaric acid, the so-called aldaric acids (Ruiz et al 2013;Lorentz et al 2012). However, up to now, only the presence of hydroxycinnamic acid glucarates has been reported (Maas et al 2009;Lorentz et al 2012;Ruiz et al 2014). The presence of this rare type of compounds was not reported in Inula sp.…”

Section: Resultsmentioning

confidence: 96%

Hydroxycinnamates from elecampane (Inula helenium L.) callus culture

2016

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Hydroalcoholic extract from Inula helenium callus tissue showed remarkable reducing capacity. An HPLC/DAD analysis revealed the presence of numerous hydroxycinnamic acid derivatives, including chlorogenic acid (5-O-CQA, 0.1 % dry weight) and 3,5-dicaffeoylquinic acid (3,5-DCQA, 0.3 % dry weight), which were among major constituents of the examined extract. Application of a hyphenated chromatographic method-UHPLC/DAD/MS n -allowed identification of sixteen compounds, derivatives of caffeic acid. Apart from the compounds commonly found in Inula sp., the plant material contained eight conjugates of caffeic acid with aldaric acid. The aldarates constituted over 50 % of the hydroxycinnamate fraction in the examined tissue. This is the first report on the occurrence of the caffeoylaldaric acids in Inula sp. and in a plant tissue culture.

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“…Jedinjenja koja su u ovom istraživanju kvantifikovana takođe su prisutna i u drugim biljkama familije Asteraceae (Apáti et al, 2004;Maas et al, 2008;Romani et al, 2002;EMEA 2008;Landa et al, 2009;Mendiondo et al, 2011;Saleh i Bohm, 1971), kao i u drugim familijama (Plazonić et al, 2009;Trute i Nahrstedt, 1997;Barros et al, 2012).…”

Section: Sadržaj Dominantnih Fenolnih Komponentiunclassified

Influence of growing conditions on morphological and chemical properties and biological effects of extracts of Arnica montana L.

Pljevljakušić¹

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Belgrade, 2012(1,7 -2,4%).Mikroskopskim snimanjem samlevenog biljnog materijala pod različitim uveličanjima ustanovljena je jednostavna procedura identifikacije cveta arnike u odnosu na dva pretpostavljena falsifikata. Tako Since the A. montana plant specie is not native to the region of Serbia, although it occurs spontaneously in some mountain areas of neighboring countries and the Balkans in general, the aim of this study was to find a suitable technology solution of field cultivation based on the examination of induced various ecological factor effects.In this research, beside observations connected with flower heads, as the main drug, underground parts of arnica: rhizome and roots, were also studied as side products. The first phase of the experimental work included a three-year three-factorial field experiment in different modes of production, where as the factors examined: time of plantation establishment (spring and autumn planting), fertilization (manure and NPK) and methods of propagation (from seed and clonal propagation -division of the tuft). In the second phase of the experiment, characterization of the raw material was carried out in the terms of its rapid identification, qualitative evaluations based on the content of secondary metabolites and testing of biological effects of extracts obtained.Tests were performed on the field experiment conducted in 2008 at locality of Kaludjerske Bare (1008 m) on mountain Tara, in area of Nursery production department of the National Park "Tara". Since arnica its first vegetation remains in the rosette phenophase, all measurements of morphological parameters, yields and chemical Summary Doctoral Dissertation

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Caffeic Acid Derivatives from Eupatorium perfoliatum L.

Cited by 45 publications

References 30 publications

Identification of Flavonoids in Leaves of a Labile Bicolor Flowering Dahlia (<i>Dahlia variabilis</i>) ‘Yuino’

Identification of Flavonoids in Leaves of a Labile Bicolor Flowering Dahlia (<i>Dahlia variabilis</i>) ‘Yuino’

Hydroxycinnamates from elecampane (Inula helenium L.) callus culture

Influence of growing conditions on morphological and chemical properties and biological effects of extracts of Arnica montana L.

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