Exudate flavonoid aglycones in the alpine species of Achillea sect. Ptarmica: Chemosystematics of A. moschata and related species (Compositae–Anthemideae)

Valant–Vetschera, Karin M.; Wollenweber, Eckhard

doi:10.1016/s0305-1978(00)00033-8

Cited by 30 publications

(17 citation statements)

References 17 publications

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“…Each one of these subfamilies presents a different and typical profile of indole alkaloids, iridoids and anthraquinones which are considered as Rubiaceae chemotaxonomic markers [49]. Other studies based on chemotaxonomic data obtained by gas chromatography coupled to mass spectrometry show that the iridoid glycosides are present in several different species belonging to the Rubiaceae subfamilies [50][51][52]. Monoterpene indole alkaloids, especially which are derivatives of tryptamine and monoterpene (iridoid) secologanin are another predominant class in Rubiaceae.…”

Section: Alizarin (Xix)mentioning

confidence: 99%

“…Other studies also describe indole alkaloids as the class of substances of major occurrence in Cinchonoideae, especially in Guettardeae tribe [50,55]. Studies by Wijinsma and Verpoorte [56] and Bolzani et al [15] describe the occurrence of standardized chemical markers: iridoids in Ixoroideae; indole alkaloids in Cinchonoideae and anthraquinones in Rubioideae.…”

Section: Data Obtained Through the Bibliographic Surveymentioning

confidence: 99%

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Secondary Metabolites from Rubiaceae Species

2015

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This study describes some characteristics of the Rubiaceae family pertaining to the occurrence and distribution of secondary metabolites in the main genera of this family. It reports the review of phytochemical studies addressing all species of Rubiaceae, published between 1990 and 2014. Iridoids, anthraquinones, triterpenes, indole alkaloids as well as other varying alkaloid subclasses, have shown to be the most common. These compounds have been mostly isolated from the genera Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda. The occurrence and distribution of iridoids, alkaloids and anthraquinones point out their chemotaxonomic correlation among tribes and subfamilies. From an evolutionary point of view, Rubioideae is the most ancient subfamily, followed by Ixoroideae and finally Cinchonoideae. The chemical biosynthetic pathway, which is not so specific in Rubioideae, can explain this and large amounts of both iridoids and indole alkaloids are produced. In Ixoroideae, the most active biosysthetic pathway is the one that produces iridoids; while in Cinchonoideae, it produces indole alkaloids together with other alkaloids. The chemical biosynthetic pathway now supports this botanical conclusion.

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Section: Alizarin (Xix)mentioning

confidence: 99%

Section: Data Obtained Through the Bibliographic Surveymentioning

confidence: 99%

Secondary Metabolites from Rubiaceae Species

2015

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“…Isoflavonoid secretion affects the surrounding microflora in the rhizosphere (Weisskopf et al, 2006), attracts mutualistic microorganisms such as nitrogen-fixing bacteria, and enhances defense responses to pathogens (Paiva, 2000;Dakora and Phillips, 2002). Flavonol glycosides have been detected in the cell wall fraction of Scots pine (Pinus sylvestris) needles (kaempferol 3-glucoside; Schnitzler et al, 1996) and Chrysosplenium americanum (polymethylated flavonol glucosides; Ibrahim et al, 1987), while flavonoid aglycones, including flavones and flavonols, have been detected in exudates of numerous species (Valant-Vetschera and Wollenweber, 2001;Wollenweber et al, 2003).…”

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confidence: 99%

Flavonoid Biosynthesis in Barley Primary Leaves Requires the Presence of the Vacuole and Controls the Activity of Vacuolar Flavonoid Transport

et al. 2007

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Barley (Hordeum vulgare) primary leaves synthesize saponarin, a 2-fold glucosylated flavone (apigenin 6-C-glucosyl-7-Oglucoside), which is efficiently accumulated in vacuoles via a transport mechanism driven by the proton gradient. Vacuoles isolated from mesophyll protoplasts of the plant line anthocyanin-less310 (ant310), which contains a mutation in the chalcone isomerase (CHI) gene that largely inhibits flavonoid biosynthesis, exhibit strongly reduced transport activity for saponarin and its precursor isovitexin (apigenin 6-C-glucoside). Incubation of ant310 primary leaf segments or isolated mesophyll protoplasts with naringenin, the product of the CHI reaction, restores saponarin biosynthesis almost completely, up to levels of the wild-type Ca33787. During reconstitution, saponarin accumulates to more than 90% in the vacuole. The capacity to synthesize saponarin from naringenin is strongly reduced in ant310 miniprotoplasts containing no central vacuole. Leaf segments and protoplasts from ant310 treated with naringenin showed strong reactivation of saponarin or isovitexin uptake by vacuoles, while the activity of the UDP-glucose:isovitexin 7-O-glucosyltransferase was not changed by this treatment. Our results demonstrate that efficient vacuolar flavonoid transport is linked to intact flavonoid biosynthesis in barley. Intact flavonoid biosynthesis exerts control over the activity of the vacuolar flavonoid/H 1 -antiporter. Thus, the barley ant310 mutant represents a novel model system to study the interplay between flavonoid biosynthesis and the vacuolar storage mechanism.

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“…These 'surface' or 'exudate flavonoids' are in most cases lipophilic, predominantly aglycones that in many cases are strongly methylated (Valant-Vetschera and Wollenweber, 2001 ;Wollenweber et al, 2003 ;Onyilagha and Grotewold, 2004) which was defined as a characteristic modification necessary to achieve passing through the lipophilic waxes or lipids (Stafford, 1990) . However, the polar or apolar nature of flavonoids cannot be strictly associated with their extrusion to the extracellular surface or vacuolar storage, respectively, because as well hydrophobic flavonoids such as quercetin 3-methyl ethers appearing in leaf vacuoles of Vellozia streptophylla as presence of polar flavonoid glucosides on the leaf surface of Heteranthemis viscidehirta or Chrysanthemum segetum have been reported (Harborne et al, 1994 ;Valant-Vetschera et al, 2003) .…”

Section: Non-vacuolar Transportmentioning

confidence: 99%

Handling Dangerous Molecules: Transport and Compartmentation of Plant Natural Products

Klein

Roos

2009

Plant-Derived Natural Products

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The plant cell faces a dilemma: secondary products provide a multitude of defence and signalling functions, but their biosynthesis poses a severe burden, as it competes for energy sources and building blocks and may generate toxic products. Thus, evolution of recent secondary metabolites is not only driven by their advantageous functions but also selects for strict control mechanisms including the integration of biosynthesis into the cellular ultrastructure. In order to minimize the risk of self-intoxication, secondary products are usually targeted into compartments of low metabolic activity, notably the vacuole and the extracellular space. This is most obvious for phenolic substances but also for alkaloids, the best studied plant toxins. Compartmentation on a cellular or subcellular level is also instrumental in plants synthesizing preformed defence substances such as cyanogenic glycosides in order to assure that the active toxins are only liberated in case of an attack. Biosynthetic pathways and regulatory elements are wellestablished at least for some natural compound classes such as the flavonoids. In contrast, our knowledge of transport steps behind the subcellular distribution of these substances is just scratching the surface.This chapter provides an overview on transport processes involved in secondary metabolite compartmentation that is concentrated at the best known areas of flavonoid and alkaloid production. Starting from 'classical' data of secondary metabolite transport we characterize the actually known transporters -which mainly belong to the A TP-B inding C assette (ABC) or M ultidrug a nd T oxic E xtrusion (MATE) superfamilies -and their specific functioning in cells and tissues as analyzed by modern experimental techniques. The 'transporter' hypothesis is confronted with 'vesicle transport' models of subcellular trafficking. Although it appears premature to find common ground between these alternative models, the discovery of novel cellular functions of secondary metabolites facilitates our understanding of an intimate interplay between biosynthetic steps, transmembrane 11A.E. Osbourn and V. Lanzotti (eds.), Plant-derived Natural Products, 229

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Exudate flavonoid aglycones in the alpine species of Achillea sect. Ptarmica: Chemosystematics of A. moschata and related species (Compositae–Anthemideae)

Cited by 30 publications

References 17 publications

Secondary Metabolites from Rubiaceae Species

Secondary Metabolites from Rubiaceae Species

Flavonoid Biosynthesis in Barley Primary Leaves Requires the Presence of the Vacuole and Controls the Activity of Vacuolar Flavonoid Transport

Handling Dangerous Molecules: Transport and Compartmentation of Plant Natural Products

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