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Nezbedová, Lenka; Hesse, Manfred; Dušek, Jaromír; Werner, Christa

doi:10.1023/a:1006363612428

Cited by 9 publications

(11 citation statements)

References 24 publications

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“…A similar response was reported for Rehmania glutinosa (Shoyama et al 1986) and Aphelandra sp. (Nezbedova et al 1999), both closely related to the Buddlejaceae. However, there are no reports about the influence of NAA on the root induction for other closely related species nor for callus percentages (Shoyama et al 1986;Inagaki et al 1991;Pletsch et al1993;Yamamoto et al 1998;Nezbedova et al 1999), but our results showed the relevance of exploring several PGRs for response induction purposes.…”

Section: Resultsmentioning

confidence: 99%

“…Measurements of fresh and dry biomass weight were made at 15 intervals during 40 days of culture. GI was calculated gravimetrically as indicated by Nezbedova et al (1999) while l and td were estimated from exponential stage measurements as indicated by Quintero (1993). The corresponding measurement from each interval was made from three glass containers each one inoculated with 2 g of fresh biomass (n = 3).…”

Section: Maintenance and Stability Of Culturesmentioning

confidence: 99%

“…The therapeutic properties have been attributed to major compounds belonging to the phenylpropanoid pathway which have been isolated from aerial parts. Those phenylpropanoids include the conjugated phenylpropanoid verbascoside, the flavonoid linarin, and the p-coumaric, caffeic, ferulic and sinapic hydroxycinnamic acids, all of which are credited with one or other of the following activities: parasiticide, anti-microbial, analgesic, anti-viral, anti-proliferative, anti-hypertensive, anti-oxidant and anti-inflammatory (Fernandez et al 2004;Martínez-Vázquez et al 1998;Nezbedova et al 1999;Inagaki et al 1991). Others compounds belonging to terpenoid metabolites have been isolated, such the iridoid aucubin with anti-bacterial and anti-oxidant activities, and buddledin A with pesticide, piscicidal and anti-fungal activities (Houghton et al 2003).…”

Section: Introductionmentioning

confidence: 99%

“…There are no published reports regarding the phenylpropanoid production of B. cordata in tissue culture. Nevertheless, tissue cultures for producing bioactive compounds by other medicinal plants (wild or cultivated) closely related to the Buddlejaceae have been reported (Dhakulkar et al 2005;Nezbedova et al 1999;Skrzypek and Wysokinska 1999;Wysokinska and Rozga 1998;Pletsch et al 1993).…”

Section: Introductionmentioning

confidence: 99%

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Phenylpropanoid production in callus and cell suspension cultures of Buddleja cordata Kunth

Estrada-Zúñiga

Cruz-Sosa

Rodrı́guez-Monroy

et al. 2009

Plant Cell Tiss Organ Cult

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Plant tissue cultures represent a potential source for producing secondary metabolites. In this work, Buddleja cordata tissue cultures were established in order to produce phenylpropanoids (verbascoside, linarin and hydroxycinnamic acids), as these metabolites are credited with therapeutic properties. Highest callus induction (76.4-84.3%) was obtained in five treatments containing 2,4-Dichlorophenoxyacetic acid (2,4-D: 0.45-9.05 lM) with Kinetin (KIN: 2.32, 4.65 lM), whereas highest root induction (79.6%) corresponded to the a-Naphthaleneacetic acid (9.05 lM) with KIN (2.32 lM) treatment. Verbascoside was the major phenylpropanoid produced in in vitro cultures (root, white and green callus) [66.24-86.26 mg g -1 dry weight (DW)], while linarin and hydroxycinnamic acid production was low (0.95-3.01 mg g -1 DW). Verbascoside and linarin production were improved in cell suspension culture (116 mg g -1 DW and 8.12 mg g -1 DW, respectively).

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Section: Resultsmentioning

confidence: 99%

Section: Maintenance and Stability Of Culturesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Phenylpropanoid production in callus and cell suspension cultures of Buddleja cordata Kunth

Estrada-Zúñiga

Cruz-Sosa

Rodrı́guez-Monroy

et al. 2009

Plant Cell Tiss Organ Cult

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“…± So far, aphelandrine (1) has been found exclusively in the roots of different Aphelandra species. The cell cultures from A. tetragona and A. sinclairiana have been shown to be devoid of any alkaloids [8]. Aphelandrine (1) is easily detectable in the roots of A. squarrosa already 4 weeks after planting by shoot propagation.…”

mentioning

confidence: 99%

Prelandrine, the Key-Step Intermediate in the Biosynthesis of the Macrocyclic Spermine Alkaloid Aphelandrine

Nezbedová

Hesse

Drandarov

et al. 2001

HCA

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Dedicated to Professor Elmar Vilsmaier on the occasion of his 60th birthday By means of the high sensitive on-line-coupled high-performance liquid chromatography and atmosphericpressure chemical-ionization mass spectrometry (HPLC/APCI-MS and HPLC/APCI-MS/MS) techniques, the new macrocyclic spermine alkaloid prelandrine (5) was detected in the roots of Aphelandra squarrosa (Acanthaceae), and its structure was elucidated as 4'-hydroxyprotoverbine ( 8-(4-hydroxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one). It was further demonstrated that protoverbine (6) is enzymatically hydroxylated to prelandrine (5) in a reaction catalyzed by microsomes from the roots of A. squarrosa. The chemical synthesis of (À)-(S)-prelandrine is also described. The possible key role of prelandrine (5) as an intermediate in the biosynthesis of aphelandrine (1) is discussed.Introduction. ± The macrocyclic spermine alkaloid aphelandrine (1; Scheme) is a member of a rather rare class of natural products. Aphelandrine (1) has been found as the major alkaloid in the roots of several Aphelandra species [1 ± 3]. Although the structure of aphelandrine (1) displays p-coumaric acid and spermine (or spermidine and putrescine) as building blocks, little is known about the biosynthesis of this type of alkaloids. The feeding experiments with 3 H-and 14 C-labelled putrescine, spermidine, and coumaric acid confirmed the biogenetic structural units of aphelandrine; however, the question of whether mono-or dicoumaroylspermine is the precursor remained unanswered [4 ± 6]. For the further steps, there are two hypotheses: the first involves cyclization of N(1),N(5)-di(p-coumaroyl)spermine (3) leading to the species 2, which subsequently undergoes phenol coupling to give aphelandrine (1; Scheme) [7]. The second possibility is transformation of N(1)-cinnamoylspermine (4a) or N(1)(pcoumaroyl)spermine (4b) to the macrocycle 6 or 5, respectively, followed by acylation to give 2, which again undergoes phenol coupling to give aphelandrine (1; Scheme). When N(1)-cinnamoylspermine (4a) is cyclized by Michael addition, a hydroxylation step leading from 6 to 5 would be expected.So far, there exists no evidence to support one of these possibilities, presumably because of the concentration limits of the conventional analytical methods. Application of high-sensitive on-line-coupled HPLC/APCI-MS (atmospheric-pressure chemicalionization mass spectrometry) or ESI-MS (electrospray-ionization mass spectrometry) techniques allows the detection of substances, in some cases, at picomolar concentrations. Moreover, HPLC co-eluted substances can be easily differentiated by their molecular weights. The MS/MS spectra of selected quasi-molecular ions ([M H] ) very often provide substantial structural information without isolation.

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Phenol oxidative coupling in the biogenesis of the macrocyclic spermine alkaloids aphelandrine and orantine in Aphelandra sp.

Nezbedová¹,

Hesse²,

Drandarov³

et al. 2001

Planta

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A crucial step in the biosynthesis of the spermine alkaloid aphelandrine and its diastereoisomer orantine is an intramolecular cyclization of the intermediate (S)-dihydroxyverbacine. In order to elucidate this step of the biosynthetic pathway, microsomes from the roots of Aphelandra squarrosa Nees were incubated with unlabeled and (D8)-labeled (S)-dihydroxyverbacine. It was shown that the microsomal fraction catalyzes the intramolecular coupling of (S)-dihydroxyverbacine to aphelandrine. This was proven by microsomal transformation of (D8)-labeled (S)-dihydroxyverbacine to (D8)-labeled aphelandrine. The reaction absolutely requires NAPDH and O2. The underlying reaction mechanism is probably an oxidative phenol coupling catalyzed by an aphelandrine synthase. This enzyme is proposed to be a cytochrome P-450 oxidase. The intramolecular cyclization of (S)-dihydroxyverbacine represents an important point in the biogenesis of the aphelandrine-type alkaloids.

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Untitled

Cited by 9 publications

References 24 publications

Phenylpropanoid production in callus and cell suspension cultures of Buddleja cordata Kunth

Phenylpropanoid production in callus and cell suspension cultures of Buddleja cordata Kunth

Prelandrine, the Key-Step Intermediate in the Biosynthesis of the Macrocyclic Spermine Alkaloid Aphelandrine

Phenol oxidative coupling in the biogenesis of the macrocyclic spermine alkaloids aphelandrine and orantine in Aphelandra sp.

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