The structures of salicortin and tremulacin

Pearl, Irwin A.; Darling, Stephen F.

doi:10.1016/s0031-9422(00)97369-2

Cited by 38 publications

(21 citation statements)

References 10 publications

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“…Catechol is an excellent substrate for trembling aspen PPO (J. J. Patton and C. P. Constabel, unpublished data). Furthermore, it had previously been demonstrated that under basic conditions, catechol is formed as a decomposition product of salicortin and tremulacin (Pearl and Darling 1971).…”

Section: Resultsmentioning

confidence: 99%

Polyphenol oxidase and herbivore defense in trembling aspen (Populus tremuloides): cDNA cloning, expression, and potential substrates

Haruta

Pedersen

Constabel

2001

Physiologia Plantarum

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The biochemical anti-herbivore defense of trembling aspen (Populus tremuloides Michx.) was investigated in a molecular analysis of polyphenol oxidase (PPO; EC 1.10.3.2). A PPO cDNA was isolated from a trembling aspen wounded leaf cDNA library and its nucleotide sequence determined. Southern analysis indicated the presence of two PPO genes in the trembling aspen genome. Expression of PPO was found to be induced after herbivory by forest tent caterpillar, by wounding, and by methyl jasmonate treatment. Wound induction was systemic, and occurred in unwounded leaves on wounded plants. This pattern of expression is consistent with a role of this enzyme in insect defense. A search for potential PPO substrates in ethanolic aspen leaf extracts using electron spin resonance (ESR) found no pre-existing diphenolic compounds. However, following a brief delay and several additions of oxygen, an ESR signal specific for catechol was detected. The source of this catechol was most likely the aspen phenolic glycosides tremulacin or salicortin which decomposed during ESR experiments. This was subsequently confirmed in experiments using pure salicortin.

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Section: Resultsmentioning

confidence: 99%

Polyphenol oxidase and herbivore defense in trembling aspen (Populus tremuloides): cDNA cloning, expression, and potential substrates

Haruta

Pedersen

Constabel

2001

Physiologia Plantarum

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“…On the other hand, Pearl and Darling (1971) focused their attention on the structure of salicortin, the ester of salicin and tremulacin, which is 2-O-benzoyl ester of salicortin. The studies were conducted by hydrogenolysis, acid and alkaline hydrolysis as well as infrared spectroscopy (IR) and NMR.…”

Section: Historical Outline Of Research On Phenolic Compoundsmentioning

confidence: 99%

Characterization of bioactive compounds in the biomass of black locust, poplar and willow

Tyśkiewicz

Konkol

Kowalski

et al. 2019

Trees

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Key message Liquid chromatography is the main method for assaying bioactive compounds in biomass. Total phenolic content and antioxidant capacity are measured with spectroscopy. Phenolics are the most important bioactive substances in short rotation coppice. Secondary metabolites of black locust, willow and poplar have many different activities. The richest source of bioactive compounds are flowers, bark and buds. Abstract The black locust (Robinia pseudoacacia), willow (Salix spp.) and poplar (Populus spp.) may be the source of the biomass obtained from natural habitats as well as intentionally established plantations in the system of short rotation coppice. These species are promising candidates as an alternative source of bioactive compounds in researches for developing new bioproducts for multidirectional uses, including polymers, lubricants, construction materials, pharmaceuticals, as well as bioenergy and fuels. Various parts of plants, such as leaves, flowers, seeds, bark, woods, buds, catkins, whole tree material and bee products (honey, propolis) are a source of bioactive compounds. The characterization of these compounds, especially phenolic compounds (flavonoids, stilbenes, lignans, phenolic acids, tannins and phenolic glucosides), fatty acids, sterols, etc. may be determined by a variety of analytical (spectroscopy, chromatography) and extraction methods. This review contains 131 references and systematize all available data on the characterization of the bioactive compounds in the biomass of black locust, poplar and willow by analytical and extraction methods.

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“…Both PGs and CTs are thought to be derived from the phenylpropanoid pathways [6]. Salicin (salicyl alcohol glucoside, O -hydroxymethyl phenyl β-D-glucoside), the first PG-like substance isolated from Salix bark, is considered a potential precursor of higher-order PGs, such as salicortin and tremulacin [2,7,8]. CTs are polyphenolics composed of proanthocyanidin monomers, and are derived from the flavonoid pathway initiated by the conjugation and modification of phenylpropanoid and malonyl-CoA [6,9,10].…”

Section: Introductionmentioning

confidence: 99%

Glycosylation-mediated phenylpropanoid partitioning in Populus tremuloides cell cultures

et al. 2009

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BackgroundPhenylpropanoid-derived phenolic glycosides (PGs) and condensed tannins (CTs) comprise large, multi-purpose non-structural carbon sinks in Populus. A negative correlation between PG and CT concentrations has been observed in several studies. However, the molecular mechanism underlying the relationship is not known.ResultsPopulus cell cultures produce CTs but not PGs under normal conditions. Feeding salicyl alcohol resulted in accumulation of salicins, the simplest PG, in the cells, but not higher-order PGs. Salicin accrual reflected the stimulation of a glycosylation response which altered a number of metabolic activities. We utilized this suspension cell feeding system as a model for analyzing the possible role of glycosylation in regulating the metabolic competition between PG formation, CT synthesis and growth. Cells accumulated salicins in a dose-dependent manner following salicyl alcohol feeding. Higher feeding levels led to a decrease in cellular CT concentrations (at 5 or 10 mM), and a negative effect on cell growth (at 10 mM). The competition between salicin and CT formation was reciprocal, and depended on the metabolic status of the cells. We analyzed gene expression changes between controls and cells fed with 5 mM salicyl alcohol for 48 hr, a time point when salicin accumulation was near maximum and CT synthesis was reduced, with no effect on growth. Several stress-responsive genes were up-regulated, suggestive of a general stress response in the fed cells. Salicyl alcohol feeding also induced expression of genes associated with sucrose catabolism, glycolysis and the Krebs cycle. Transcript levels of phenylalanine ammonia lyase and most of the flavonoid pathway genes were reduced, consistent with down-regulated CT synthesis.ConclusionsExogenous salicyl alcohol was readily glycosylated in Populus cell cultures, a process that altered sugar utilization and phenolic partitioning in the cells. Using this system, we identified candidate genes for glycosyltransferases that may mediate the glycosylation, and for transporters that mediate the subcellular compartmentalization of sugars and phenolic glycosides. The suspension cells appear to represent a facile system for dissecting the regulation of phenolic carbon partitioning, and in turn, its effects on growth in Populus.

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The structures of salicortin and tremulacin

Cited by 38 publications

References 10 publications

Polyphenol oxidase and herbivore defense in trembling aspen (Populus tremuloides): cDNA cloning, expression, and potential substrates

Polyphenol oxidase and herbivore defense in trembling aspen (Populus tremuloides): cDNA cloning, expression, and potential substrates

Characterization of bioactive compounds in the biomass of black locust, poplar and willow

Glycosylation-mediated phenylpropanoid partitioning in Populus tremuloides cell cultures

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