Incorporation of kaempferol 3-O-glucoside into the cell walls of Norway spruce needles

Heilemann, Jürgen; Strack, Dieter

doi:10.1007/bf00193016

Cited by 11 publications

(8 citation statements)

References 20 publications

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“…Continuous increase of cell wall-bound metabolite levels throughout the 2 years of needle development studied concomitant with the early transient maximum of the soluble, diacylated F3Gs (Figs 1 & 2) suggests that soluble metabolites are translocated and covalently bound to the cell wall. Similar observations exist for Norway spruce and other Pinaceae species (Strack et al 1989;Heilemann & Strack 1990;Schnitzler et al 1996;Fischbach et al 1999) as well as some Mediterranean evergreen broad-leaved trees (Liakoura, Manetas & Karabourniotis 2001). Based on fluorescence microscopic studies with trichomes of Quercus ilex and Olea europaea, it had been suggested that polyphenols are translocated from the perinuclear and cytoplasmatic space to cell walls during leaf ageing (Karabourniotis et al 1998).…”

Section: Discussionsupporting

confidence: 56%

“…The possible involvement of diacylated F3Gs in the process of cell‐wall deposition has been earlier indicated but was not further analysed (Strack et al . 1989; Heilemann & Strack 1990; Schnitzler et al . 1996; Fischbach et al .…”

Section: Discussionmentioning

confidence: 99%

“…Based on fluorescence microscopic studies with trichomes of Quercus ilex and Olea europaea, it had been suggested that polyphenols are translocated from the perinuclear and cytoplasmatic space to cell walls during leaf ageing (Karabourniotis et al 1998). The possible involvement of diacylated F3Gs in the process of cell-wall deposition has been earlier indicated but was not further analysed (Strack et al 1989;Heilemann & Strack 1990;Schnitzler et al 1996;Fischbach et al 1999). The fact that total cell wall-bound hydroxycinnamic acids released upon alkaline hydrolysis are only about half the molar amount of F3Gs released is in favour of a model where acylated intermediates are covalently bound to the cell wall via their hydroxycinnamic acid residues.…”

Section: Discussionmentioning

confidence: 99%

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Environmental and developmental effects on the biosynthesis of UV‐B screening pigments in Scots pine (Pinus sylvestris L.) needles

Kaffarnik

Seidlitz²,

Obermaier

et al. 2006

Plant Cell & Environment

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The major UV-B screening pigments of the epidermal layer of Scots pine ( Pinus sylvestris ) needles are flavonol 3-oglycosides (F3Gs) esterified with hydroxycinnamic acids at positions 3 ¢¢ and 6 ¢¢ . Acylation is the last step in biosynthesis and is catalysed by position-specific hydroxycinnamoyl transferases (3 ¢¢ and 6 ¢¢ HCT). The UV-B dependence of these enzyme activities was studied in primary needles of Scots pine seedlings grown under different UV-B conditions in environmentally controlled sun simulators. 6 ¢¢ HCT activity was induced upon UV-B irradiation while 3 ¢¢ HCT activity was not induced but showed high constitutive values. To investigate the biosynthesis of diacylated F3Gs during needle development under natural conditions, the HCT activities and metabolite contents were analysed in needles of field-grown mature pine trees. Accumulation of diacylated compounds as well as of 6 ¢¢ HCT activity occurred transiently in the first year of needle development only. In contrast, 3 ¢¢ HCT activity exhibited broad maxima in two consecutive years during needle growth. The data suggest that acylated F3Gs are first formed as soluble compounds which are then translocated into the cell wall to be bound by their hydroxycinnamoyl residues.

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Section: Discussionsupporting

confidence: 56%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Environmental and developmental effects on the biosynthesis of UV‐B screening pigments in Scots pine (Pinus sylvestris L.) needles

Kaffarnik

Seidlitz²,

Obermaier

et al. 2006

Plant Cell & Environment

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“…The disappearance of these caffeic acid esters is due to either degradation, transport to an insoluble caffeic acid ester pool (cell wall? ; see Lam et al, 1992), as shown for a flavonol glucoside in Norway spruce needles (Heilemann and Strack, 1990), or translocation into another organ. In rhizomes a11 esters were detected in concentrations ranging from 0.1 to 0.8% of the dry weight over the entire growing season and winter (not documented).…”

Section: Substrate Specificitiesmentioning

confidence: 87%

Hydroxycinnamoyltransferases Involved in the Accumulation of Caffeic Acid Esters in Gametophytes and Sporophytes of Equisetum arvense

1996

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Four hydroxycinnamoyltransferases from Equisefum arvense L. were studied that catalyze the formation of mono-Ocaffeoylmeso-tartrate, di-O-caffeoyl-meso-tartrate, 5-Ocaffeoylshikimate (dactylifrate), and 5-Ocaffeoylquinate (chlorogenate). l h e enzymes were classified as coenzyme A (COA)-ester-dependent acyltransferases (EC 2.3.1), i.e. hydroxycinnamoyl-CoAmeso-tartrate hydroxycinnamoyltransferase (CTT), hydroxycinnamoyl-CoA:caffeoyl-meso-tartrate hydroxycinnamoyltransferase (CCT), hydroxycinnamoyl-CoAshikimate hydroxycinnamoyltransferase (CST), and hydroxycinnamoyl-CoA:quinate hydroxycinnamoyltransferase. The CTT, CCT, and CST were partially purified and separated from E. arvense gametophytes by hydrophobic interaction chromatography on Fractogel TSK Butyl-650 followed by molecular exclusion on fast protein liquid chromatography-Superdex-75 with 87-, 62-, and 130-fold enrichments and 12, 8, and 11% yields, respectively. The enzyme activities obtained with caffeoyl-COA were 95 (CTT), 74 (CCT), and 200 pkat (CST) kg-' protein. The apparent native relative molecular weight values were found t o be approximately 45,000 (CTT), 52,000 (CCT), and 50,000 (CST). Each enzyme showed highest activities at p H 7.5, the CCT and CST i n lris-HCI (1.2 and 1.0 M) and the CTT in imidazole-HCI (1.25 M). Enzyme activities were stimulated more than 3-fold by 1 O0 mM ascorbate. l h e apparent energies of activation (kilojoules mol-') were calculated t o be 56 (CTT), 69 (CST), and 76 (CCT). The enzymes accepted cinnamoyl-COA and various hydroxycinnamoyl-CoAs. The time course of the transferase activities along with that of a fourth one, hydroxycinnamoyl-CoA:quinate hydroxycinnamoyltransferase, and the pattern of product accumulation were determined during a 1 -year growth period of the E. arvense sporophytes.The sterile and fertile sporophytes of Equisetum arvense (horsetail) and some other Equisetum species accumulate a highly complex pattern of phenolic compounds, i.e. various flavonoids, styrylpyrone glucosides, and caffeic acid esters (Veit et al., 1995). In contrast, the gametophytes of E. arvense lack any flavonoids but accumulate styrylpyrone glucosides and caffeic acid esters. The latter are the most widespread hydroxycinnamic acid conjugates in plants (Merlgaard and Ravn, 1988 ( Matern and Kneusel, 1988). Recently, we elucidated the structures of caffeic acid esters in E. arvense, a tartrate diester and a shikimate monoester (Veit et al., 1991b(Veit et al., , 1992. Whereas the shikimate ester (5-O-caffeoylshikimate = dactylifrate) seems to be widespread among members of the Equisetaceae, along with a quinate ester (5-0-caffeoylquinate = chlorogenate), the occurrence of the tartrate ester is characteristic for E. arvense (Veit et al., 1992). These caffeic acid esters show, in contrast to the flavonoids and styrylpyrones, transient accumulation patterns in the sporophytes with high concentrations in spring decreasing to low amounts until the autumn months (Veit et al., 1991b;Weidner et al., 1991).As part of our studies on the e...

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“…Cell-wall-associated¯avonol glycosides have been detected in the needles of conifers (Strack et al 1989). In pulse-chase experiments 14 C-labeled CO 2 was incorporated into soluble kaempferol 3-O-glucoside which was detected 3 weeks later in an insoluble extracellular fraction (Heilmann and Strack, 1990). In other tracer studies using suspension-cultured plant cells,¯avonols with free 3-and 4¢-hydroxyl groups were degraded under speci®c conditions to 2,3-dihydroxy¯avones Muhle et al 1976) which could be further decomposed to form benzoic acid derivatives (HoÈ sel et al 1975;Miller and Schreier 1985).…”

Section: Introductionmentioning

confidence: 97%

Uptake and metabolism of flavonols during in-vitro germination of Petunia hybrida (L.) pollen

Vogt

Taylor

1997

Planta

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Flavonol-de®cient petunia pollen [conditionally male fertile (CMF) pollen] is unable to germinate but application of nanomolar concentrations of¯avonol aglycones completely restores function (Mo et al. 1992). In this study a chemically synthesized radioactivē avonol, [4¢-O-14 C]kaempferide, was used as a model compound to study the metabolism of¯avonols during the ®rst few hours of pollen germination. [4¢-O-14 C]Kaempferide was as ecient at inducing CMF pollen germination as kaempferol and quercetin, the aglycone form of the endogenous¯avonols in petunia pollen. Analysis by high-performance liquid chromatography (HPLC) of extracts from both in-vitro-germinated pollen and the germination medium showed that more than 95% of the applied radioactivity was recovered as three kaempferide 3-O-glycosides and unmetabolized kaempferide; no¯avonol catabolites were detected. Only HPLC fractions that contained the aglycone, or produced it upon acid hydrolysis, could induce CMF pollen germination in vitro. Structurally diverse¯avonols could be classi®ed according to how eciently the aglycone was internalized and glycosylated during pollen germination. The ability of an individual¯avonol to restore germination correlated with the total uptake of¯avonols but not with the amount of glycoside formed in the pollen. Thus this study reinforces the conclusion that avonol aglycones are the active compound for inducing pollen germination. Abbreviations: CMF = conditionally male fertile; FAB-MS = fast atom bombardment mass spectroscopy; GM = germination medium;[4¢-O-14 C]kaempferide = 14 C-labeled

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Incorporation of kaempferol 3-O-glucoside into the cell walls of Norway spruce needles

Cited by 11 publications

References 20 publications

Environmental and developmental effects on the biosynthesis of UV‐B screening pigments in Scots pine (Pinus sylvestris L.) needles

Environmental and developmental effects on the biosynthesis of UV‐B screening pigments in Scots pine (Pinus sylvestris L.) needles

Hydroxycinnamoyltransferases Involved in the Accumulation of Caffeic Acid Esters in Gametophytes and Sporophytes of Equisetum arvense

Uptake and metabolism of flavonols during in-vitro germination of Petunia hybrida (L.) pollen

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