[On a diterpene from the roots of Solidago canadensis L. and Solidago gigantea Ait. (Solidago serotina Ait.)].
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Chemical Phenomena↗
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[Knowledge of saponins of genus Solidago. 1. Saponins of Solidago virgaurea L].
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Chromatography, Thin Layer↗
[Bayogenin -- a sapogenin in Solidago canadensis L. 2. The saponins of the species Solidago].
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Plants, Medicinal↗
[HPLC investigation of antioxidant components in Solidago herba].
Representatives of Solidago species have been used in European phytotheraphy for centuries as a component of urological and antiphlogistical remedies. Solidago canadensis L. (Asteraceae) contains a wide range of active ingredients, such as flavonoids, saponins, hydroxycinnamates and mineral elements, which are responsible for its characteristic anti-inflammatory, spasmolytic and diuretic properties. Quality control of collected Solidaginis herba were performed according to the instructions of the X. German Pharmacopoea, while different LC-MS technologies were applied to evaluate the exact phenoloid composition. Three flavonol aglycons (quercetin, kaempferol and isorhamnetin) connected to several sugar components (glucose, rhamnose, galactose and rutinose), caffeoylquinic acid and a caffeoyl-shikimic acid glycoside were identified in the samples. Quercetin-3-O-beta-glucoside (isoquercitrin), quercetin-3-O-beta-galactoside (hyperoside), quercetin-3-O-beta-rhamnoside (quercitrin), quercetin-3-O-beta-rutinoside (rutin), kaempferol-3-O-beta-rhamnoside (afzelin), kaempferol-3-O-beta-rutinoside (nicotiflorin), caffeoil-quinic acid (chlorogenic acid) were identified in sample "A", while the presence of quercetin, quercetin-3-O-beta-glucoside (isoquercitrin), quercetin-3-/6"-O-acetyl-/-beta-glucopiranoside, quercetin-3-O-beta-rutinoside (rutin), kaempferol, kaempferol-3-O-beta-glucoside (astragalin), kaempferol-3-/6"-O-acetyl-/-beta-glucopiranoside, isorhamnetin, isorhamnetin-3-/6"-O-acetyl-/-beta-glucopiranoside, isorhamnetin-3-O-beta-rutinoside (narcissin), caffeoil-quinic acid (chlorogenic acid), caffeoil-shikimic acid-glucoside (dattelic acid-glucoside) were confirmed in sample "B". According to the occurrence of acetyl-glycosides and the diversity of sugar component of flavonoid glycosides Solidaginis herba samples chemotaxonomically were classified into different varieties. Incidence of acetyl-glycosidic flavonoids and absence of flavonoid galactosides and rhamnosides in the sample "B" together give support for the taxonomic recognition of varietases Solidago canadensis L. var. canadensis and var. scabra. Sample "A" was identified as Solidago canadensis L. var. canadensis, while sample "B" has proved to be belong to variety Solidago canadensis L. var. scabra. Due to the same flavonoid aglycons and the large amounts of flavonol glycosides occurring in each drug, phytochemical characteristics of investigated samples proved to be very similar.
Antioxidants↗
Anti-inflammatory, spasmolytic and diuretic effects of a commercially available Solidago gigantea Herb. extract.
The evaluation of a commercially available Solidago gigantea Herb. extract (Urol mono) revealed pronounced anti-inflammatory properties in the rat with respect to a reduction of the carrageenin-induced rat paw oedema. A direct comparison with diclofenac-Na (3 mg/kg b.w. p.o.) revealed that a high dose of Solidago gigantea Herb. extract possesses the same anti-inflammatory efficacy as diclofenac-Na. In addition, the Solidago gigantea Herb. extract exhibited moderate spasmolytic and diuretic properties.
Animals↗
Biosynthesis of the sesquiterpene germacrene D in Solidago canadensis: 13C and (2)H labeling studies.
The biogenetic origin of the isoprenoid building blocks of the sesquiterpene germacrene D was studied in Solidago canadensis. Feeding experiments were carried out with 1-[5,5-D(2)]deoxy-D-xylulose-5-phosphate (D(2)-DOXP), [5-13C]mevalonolactone (13C-MVL) and [1-13C]-D-glucose. The hydrodistillate of a cut shoot fed with D(2)-DOXP was investigated by enantio-MDGC-MS and the volatile fraction of a shoot supplied with 13C-MVL was examined by GC-C-IRMS. The incorporation of [1-13C]-D-glucose was analyzed by quantitative 13C NMR spectroscopy after isolation of germacrene D from the essential oil. Our labeling studies revealed that the biosynthesis of the C-15 skeleton of sesquiterpene germacrene D in Solidago canadensis proceeds predominantly via the methylerythritol phosphate pathway.
Asteraceae↗
Relative competitive abilities and growth characteristics of a narrowly endemic and a geographically widespread Solidago species (Asteraceae).
Relative competitive ability and growth characteristics of the narrow endemic Solidago shortii were compared to those of the geographically widespread S. altissima. Competition and growth studies were conducted over the entire growing season in an ambient-temperature greenhouse, using a 3:1 (v/v) native limestone soil/river sand mixture. Results from a de Wit replacement series experiment (relative yield, relative yield total, plant height, aggressivity values) with S. shortii, S. altissima, and Festuca arundinacea (common competitor) suggested the following competitive hierarchy: S. altissima = F. arundinacea > S. shortii. Using classical growth analysis, we found that the competitive hierarchy was related closely to components of plant size (dry mass, height, leaf area, leaf area duration) and not to relative growth rate or any of its components (net assimilation rate, leaf area ratio, leaf weight ratio, specific leaf area). Solidago shortii allocated proportionately more dry mass to roots (but not to rhizomes) and had significantly greater root/shoot and (root + rhizome)/shoot ratios than did S. altissima. Thus, while the morphological traits of S. shortii enable it to tolerate drier habitats than S. altissima, in moist sites S. shortii easily would be overtopped and shaded out by S. altissima. Low competitive ability may be one of several factors contributing to the narrow endemism of S. shortii.
Journal Article↗
Effects of extracts from Populus tremula L., solidago virgaurea L. and Fraxinus excelsior L. on various myeloperoxidase systems.
Extracts from Populus tremula, Solidago virgaurea and Fraxinus excelsior are used as anti-inflammatory drugs. The effects of these extracts on myeloperoxidase (MPO), an enzyme liberated by activated granulocytes and known to produce the destructive agent hypochloric acid, were investigated. Populus and Fraxinus inhibited this enzyme, Solidago was without effect. These results were obtained concordantly with four different MPO-assays (H2O2/MPO; X/XOD/MPO; activated PMN; and elastase/alpha 1-PI-MPO). Fractionation of Populus and Fraxinus extracts showed that this inhibition is due to several different compounds. Well known or wide spread substances as e.g. rutin, salicylic acid, chlorogenic acid etc. had no or only little effect on the enzyme.
Amino Acids↗
Immunobiological [correction of Immunobioloical] activity of a new benzyl benzoate from the aerial parts of Solidago virga-aurea var. gigantea.
The chromatographic separation of the hexane soluble fraction of the methanol extract of the aerial parts of Solidago virga-aurea var. gigantea M(IQ*) (Compositae) led to the isolation of a new benzylbenzoate (1) together with four known benzylbenzoates (2-5). Their structures were determined as 2-methoxybenzyl-2-hydroxybenzoate (1), benzyl-2-hydroxy-6-methoxybenzoate (2), 2-methoxybenzyl-2,6-dimethoxybenzoate (3), 2-methoxybenzyl-2-methoxy-6-hydroxybenzoate (4), and benzyl-2,6-dimethoxybenzoate (5). Their structures were established by spectroscopic methods. Biological effects of compounds, 1 and 2, were investigated in vitro using mouse peritoneal macrophages. The benzylbenzoates (1 and 2) could serve as immunotherapeutic agents by stimulating macrophage functions, with potential use in the treatment of infectious diseases.
Adjuvants, Immunologic↗
Phytochemical constituents of the aerial parts from Solidago virga-aurea var. gigantea.
The chromatographic separation of the MeOH extract of the aerial parts of Solidago virga-aurea var. gigantea M(IQ) (Compositae) led to the isolation of six terpenoids and four phenolic compounds, trans-phytol (1), ent-germacra-4(15),5,10(14)-trien-1alpha-ol (2), beta-amyrin acetate (3), ent-germacra-4(15),5,10(14)-trien-1beta-ol (4), beta-dictyopterol (5), oleanolic acid (6), kaempferol (7), kaempferol-3-O-rutinoside (8), methyl 3,5-di-O-caffeoyl quinate (9), and 3,5-di-O-caffeoyl quinic acid (10). Their structures were established by chemical and spectroscopic methods. Compounds 4, 5, and 10 showed moderate cytotoxicity against five cultured human tumor cell lines in vitro with its ED50 values ranging from 1.52 to approximately 18.57 microg/mL.
Antineoplastic Agents, Phytogenic↗
An experimental test of the evolution of increased competitive ability hypothesis in goldenrod, Solidago gigantea.
The mechanisms that allow introduced plants to become invasive are poorly understood. Here, we present a test of the evolution of increased competitive ability hypothesis, which holds that because specialized natural enemies may be absent from the introduced range, exotic plants may evolve to invest less in anti-herbivore defenses and thereby gain a competitive advantage over native plants. We grew Solidago gigantea plants derived from both the native range (North America) and the invasive range (Europe) in a common garden in the native range for 2 years. Half the plants were treated with insecticide to protect them from insect herbivores and the other half were exposed to insects that colonized the garden from nearby fields. Insect herbivore biomass was significantly higher on European plants than US plants in the first year but not the second. European plants were more heavily attacked by pathogens in both years of the study. When exposed to insect herbivores, US plants produced more seed than European plants, but when plants were protected from herbivores, seed production was equivalent between US plants and European plants. The presence of insect herbivores suppressed seed production of European plants much more than that of US plants, even though the level of herbivory experienced by European and US plants was similar in the second year, suggesting that the ability to tolerate herbivory was diminished in European plants. These results partially support the EICA hypothesis: plants from the introduced range were more susceptible to some natural enemies and benefited more from insect removal than plants from the native range. The prediction that European plants would perform better than US plants in the absence of insect herbivores was not supported.
Adaptation, Physiological↗
Elevated [CO2] and increased N supply reduce leaf disease and related photosynthetic impacts on Solidago rigida.
To evaluate whether leaf spot disease and related effects on photosynthesis are influenced by increased nitrogen (N) input and elevated atmospheric CO(2) concentration ([CO(2)]), we examined disease incidence and photosynthetic rate of Solidago rigida grown in monoculture under ambient or elevated (560 micromol mol(-1)) [CO(2)] and ambient or elevated (+4 g N m(-2) year(-1)) N conditions in a field experiment in Minnesota, USA. Disease incidence was lower in plots with either elevated [CO(2)] or enriched N (-57 and -37%, respectively) than in plots with ambient conditions. Elevated [CO(2)] had no significant effect on total plant biomass, or on photosynthetic rate, but reduced tissue%N by 13%. In contrast, N fertilization increased both biomass and total plant N by 70%, and as a consequence tissue%N was unaffected and photosynthetic rate was lower on N fertilized plants than on unfertilized plants. Regardless of treatment, photosynthetic rate was reduced on leaves with disease symptoms. On average across all treatments, asymptomatic leaf tissue on diseased leaves had 53% lower photosynthetic rate than non-diseased leaves, indicating that the negative effect from the disease extended beyond the visual lesion area. Our results show that, in this instance, indirect effects from elevated [CO(2)], i.e., lower disease incidence, had a stronger effect on realized photosynthetic rate than the direct effect of higher [CO(2)].
Ascomycota↗
New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase beta.
Bioassay-directed fractionation of a methyl ethyl ketone extract of Solidago canadensis L. (Asteraceae), using an assay to detect the lyase activity of DNA polymerase beta, resulted in the isolation of the four new lupane triterpenoids 1-4 and the seven known compounds lupeol, lupeyl acetate, ursolic acid, cycloartenol, cycloartenyl palmitate, alpha-amyrin acetate, and stigmasterol. The structures of the new compounds were established as 3beta-(3R-acetoxyhexadecanoyloxy)-lup-20(29)-ene (1), 3beta-(3-ketohexadecanoyloxy)-lup-20(29)-ene (2), 3beta-(3R-acetoxyhexadecanoyloxy)-29-nor-lupan-20-one (3), and 3beta-(3-hetohexadecanoyloxy)-29-nor-lupan-20-one (4), respectively, on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical modification studies. All 11 compounds were inhibitory to the lyase activity of DNA polymerase beta.
DNA Polymerase beta↗
A new phenolic glycoside from the aerial parts of Solidago canadensis.
A new phenolic glycoside, 2'-hydroxy-4',6'-di-O-beta-D-glucopyranosyl-butyrrophenone (1), was isolated from the aerial parts of Solidago canadensis. The structure was elucidated on the basis of spectroscopic methods.
Glycosides↗
Antimicrobial activity of extractives of Solidago microglossa.
The antimicrobial activity of the methanol extract from Solidago microglossa roots, essential oil from its aerial part and some isolated compounds was investigated. The oil exhibited concentration-dependent activity against all the tested bacteria and yeasts.
Animals↗
(+)-(10R)-Germacrene A synthase from goldenrod, Solidago canadensis; cDNA isolation, bacterial expression and functional analysis.
Profiling of sesquiterpene hydrocarbons in extracts of goldenrod, Solidago canadensis, by GC-MS revealed the presence of both enantiomers of germacrene D and lesser amounts of germacrene A, alpha-humulene, and beta-caryophyllene. A similarity-based cloning strategy using degenerate oligonucleotide primers, based on conserved amino acid sequences in known plant sesquiterpene synthases and RT-PCR, resulted in the isolation of a full length sesquiterpene synthase cDNA. Functional expression of the cDNA in E. coli, as an N-terminal thioredoxin fusion protein using the pET32b vector yielded an enzyme that was readily purified by nickel-chelate affinity chromatography. Chiral GC-MS analysis of products from of (3)H- and (2)H-labelled farnesyl diphosphate identified the enzyme as (+)-(10R)-germacrene A synthase. Sequence analysis and molecular modelling was used to compare this enzyme with the mechanistically related epi-aristolochene synthase from tobacco.
Alkyl and Aryl Transferases↗
Antimicrobial activity of Solidago virgaurea L. from in vitro cultures.
The antimicrobial activity of ethanolic and methanolic extracts of Solidago virgaurea herb from micropropagated plants and callus tissue was evaluated.
Anti-Bacterial Agents↗
Herbal remedies of Solidago--correlation of phytochemical characteristics and antioxidative properties.
In this study the correlation of phytochemical characteristics and antioxidative properties of classical herbal tea extracts-Infusum solidaginis, Decoctum solidaginis, Maceratum solidaginis-and tinctures prepared by various concentration of ethanol (40, 70, 96% v/v) have been examined for the release of flavonoids and their antioxidant activity. Quantitative and composition determination of flavonoids were carried out by spectrophotometry, high-performance liquid chromatography and capillary electrophoresis, respectively. Hydrogen-donating ability and reducing power properties were used to define in vitro radical scavenging activity of Solidago extracts, but integral antioxidative capacity was determined by luminometry (Photochem), calculating the ascorbic acid equivalents. Chlorogenic acid, quercetin-3-O-beta-D-rutinoside, quercetin-3-O-beta-D-galactoside, quercetin-3-O-beta-D-glucoside, quercetin-3-O-beta-D-rhamnoside, kaempferol-3-O-alpha-L-rhamnoside and quercetin were confirmed by retention times and UV spectra. Based on the dissolution rate, variance of flavonoid release and ascorbic acid equivalents it was concluded, that Tinctura solidaginis (70% v/v ethanol) and Infusum solidaginis are the most appropriate preparations.
Antioxidants↗