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Assessment of arbuscular mycorrhizal fungal diversity in roots of Solidago gigantea growing in a polluted soil in Northern Italy.

The arbuscular mycorrhizal (AM) status of Solidago gigantea was investigated in a contaminated site of Northern Italy, where the chemical industry ACNA (Associated National Chemical Companies) was active till 1999. To counteract the devastating effects of chemicals and to allow re-vegetation, soil from an uncontaminated area was used to cover the highly polluted hills of the industrial site about 25 years ago. On the basis of the current floristic features, the hill was divided into four areas. Heavy metal content in soil and in plant shoots and roots was determined by chemical analysis. The AM fungal community colonizing S. gigantea was investigated from a morphological and a molecular point of view. All plants were modestly colonized, but the fungal structures within the roots were normal. By PCR-RFLP and sequencing of 18S rDNA, 14 AM fungal types were identified: three of them were present in all the considered areas and nine appeared to be specific to certain areas. Glomus was the predominant AM genus. Our analysis demonstrates the presence and the relatively high level of AM species variety and shows how a remediation programme based on cover-soil has been efficient to restore a community of AM fungi, tolerant enough to proliferate in a still contaminated soil.

Environmental Pollution↗

Antineoplastic activity of Solidago virgaurea on prostatic tumor cells in an SCID mouse model.

Solidago virgaurea (goldenrod) has traditionally been used as an anti-inflammatory herbal medicine for the treatment of various symptoms, including prostatic diseases. The plant has also been reported to have antibacterial, spasmolytic, and carminative properties. During the course of our screening for antineoplastic activities in various herbal plants, we found that the extract of S. virgaurea exhibits strong cytotoxic activities on various tumor cell lines. The active component mostly resides in the leaves of the plant and is soluble in water. When the extract was fractionated by a Sephadex G-100 column, the active fraction corresponded to a molecular weight of approximately 40,000. This cytotoxic activity is effective on various tumor cell lines, including human prostate (PC3), breast (MDA435), melanoma (C8161), and small cell lung carcinoma (H520). To examine the effect of the cytotoxic activity on tumor cells in vivo, we used the rat prostate cell line (AT6.1) and an SCID mouse model. AT6.1 cells were injected into the flank of SCID mice, and then the G-100 fraction of S. virgaurea was administered intraperitoneally or subcutaneously every 3 days. The size of the tumor was measured for up to 25 days. The growth of the tumor was significantly suppressed by the G-100 fraction at 5 mg/kg without any apparent side effects. Therefore, S. virgaurea is considered to be promising as an antineoplastic medicine with minimal toxicities.

Animals↗

In-vitro effect of flavonoids from Solidago canadensis extract on glutathione S-transferase.

Solidago canadensis is typical of a flavonoid-rich herb and the effect of an aqueous ethanol extract on glutathione-S-transferase (GST) activity using HepG2 cells was compared with those of the flavonol quercetin and its glycosides quercitrin and rutin, found as major constituents. The composition of the extract was determined by HPLC and rutin was found to be the major flavonoidal component of the extract. Total GST activity was assessed using 1-chloro-2,4-dinitrobenzene as a substrate. The glycosides rutin and quercitrin gave dose-dependent increases in GST activity, with a 50% and 24.5% increase at 250 mM, respectively, while the aglycone quercetin inhibited the enzyme by 30% at 250 mM. The total extract of the herb gave an overall dose-dependent increase, the fractions corresponding to the flavonoids showed activating effects while those containing caffeic acid derivatives were inhibitory. The activity observed corresponds to that reported for similar compounds in-vivo using rats, thus the HepG2 cell line could serve as a more satisfactory method of assessing the effects of extracts and compounds on GST.

Cell Line, Tumor↗

Production of an allelopathic polyacetylene in hairy root cultures of goldenrod (Solidago altissima L.).

Hairy roots of goldenrod (Solidago altissima L.) were induced by infecting axenic plants with Agrobacterium rhizogenes strain A4. Growth and allelopathic polyacetylene (cis-dehydromatricaria ester, cis-DME) production of two independent hairy root clones were examined in several culture media and light regimes. cis-DME contents in hairy roots were at the same level as those in normal roots. cis-DME production in root cultures was several-fold lower than that of native plants and greatly repressed by light.

Alkynes↗

Secondary metabolite content in rhizomes, callus cultures and in vitro regenerated plantlets of Solidago chilensis.

An in vitro culture system leading to the formation of callus and plant regeneration, starting from nodal sections and shoot tips, was developed for Solidago chilensis (Asteraceae). The content of the gastroprotective diterpene solidagenone as well as the phenolics chlorogenic acid (CA) and rutin was determined either in rhizomes from wild growing plants and in callus and in in vitro regenerated plantlets by analytical HPLC. Additionally, total phenolic and flavonoid content was assessed in plant samples, callus and cell suspensions. In terms of dry starting material, the percentual solidagenone content in nine S. chilensis samples ranged from 0.5-3.5% for rhizomes from wild growing plants, 0.1-0.3% for callus and 0.3% for an in vitro regenerated plantlet, respectively. The highest solidagenone contents were found in the wild plant during the late summer in the months of March and April (3.5-2.2%) while highest values for chlorogenic acid (0.5%) and rutin (0.4%) were detected in May, before senescence. The callus tissue and cell suspensions contained some 1.8-2.0 and 1.2% of total phenolics, respectively. CA was the main phenolic in the cell suspension while only traces were found in the callus. Rutin was not detected in the callus nor cell culture.

Cells, Cultured↗

Low level mercury uptake by plants from natural environments--mercury distribution in Solidago altissima L.-.

In order to elucidate the participation of plants in the biogeochemical cycling of mercury in natural environments, total mercury contents in leaves, stems and roots of tall goldenrod (Solidago altissima L.), Compositae, were determined. The mercury content in stems was considerably lower than that in leaves and roots. A positive correlation of mercury content was observed between soil and roots. The leaves at the lower part of the plant tended to have a higher concentration of mercury than the upper leaves. However, the mercury content of the leaves was independent of that in the soil. These observations suggested that the leaves of the plant can accumulate environmental mercury, but the mercury does not come from the soil via the root and stems. The mercury in leaves might originate predominantly from ambient air. The mercury in the leaves accumulated from the air can be delivered to the soil when the leaves fall. The roots also can adsorb the mercury from the soil; however, the mercury does not move from the roots and is not released into the air via the plant body.

Ecosystem↗

[Allelopathic effects of invasive weed Solidago canadensis on native plants].

With growth chamber method, this paper studied the allelopathic potential of invasive weed Solidago canadensis on native plant species. Different concentration S. canadensis root and rhizome extracts were examined, and the test plants were Trifolium repens, Trifolium pretense, Medicago lupulina, Lolium perenne, Suaeda glauca, Plantago virginica, Kummerowia stipulacea, Festuca arundinacea, Ageratum conyzoides, Portulaca oleracea, and Amaranthus spinosus. The results showed that the allelopathic inhibitory effect of the extracts from both S. canadensis root and rhizome was enhanced with increasing concentration, and rhizome extracts had a higher effect than root extracts. At the lowest concentration (1:60), root extract had little effect on the seed germination and seedling growth of T. repens, but rhizome extract could inhibit the germination of all test plants though the inhibitory effect varied with different species. The inhibition was the greatest for grass, followed by forb and legume. 1:60 (m:m) rhizome extract had similar effects on seed germination and radicel growth, but for outgrowth, the extract could inhibit Kummerowia stipulacea, Amaranthus spinosus and Festuca arundinacea, had no significant impact on Lolium perenne, Plantago virginica, Ageratum conyzoides, Portulaca oleracea and Amaranthus spinosus, and stimulated Trifolium repens, Trifolium pretense and Medicago lupulina.

Pheromones↗

Isolation, characterization, and mechanistic studies of (-)-alpha-gurjunene synthase from Solidago canadensis.

The leaves of the composite Solidago canadensis (goldenrod) were shown to contain (-)-alpha-gurjunene synthase activity. This sesquiterpene is likely to be the precursor for cyclocolorenone, a sesquiterpene ketone present in high amounts in S. canadensis leaves. (-)-alpha-Gurjunene synthase was purified to apparent homogeneity (741-fold) by anion-exchange chromatography (on several matrices), dye ligand chromatography, hydroxylapatite chromatography, and gel filtration. Chromatography on a gel filtration matrix indicated a native molecular mass of 48 kDa, and SDS-PAGE showed the enzyme to be composed of one subunit with a denatured mass of 60 kDa. Its maximum activity was observed at pH 7.8 in the presence of 10 mM Mg2+ and the KM value for the substrate farnesyl diphosphate was 5.5 microM. Over a range of purification steps (-)-alpha-gurjunene and (+)-gamma-gurjunene synthase activities copurified. In addition, the product ratio of the enzyme activity under several different assay conditions was always 91% (-)-alpha-gurjunene and 9% (+)-gamma-gurjunene. This suggests that the formation of these two structurally related products is catalyzed by one enzyme. For further confirmation, we carried out a number of mechanistic studies with (-)-alpha-gurjunene synthase, in which an enzyme preparation was incubated with deuterated substrate analogues. Based on mass spectrometry analysis of the products formed, a cyclization mechanism was postulated which makes it plausible that the synthase catalyzes the formation of both sesquiterpenes.

Asteraceae↗

Cytotoxic constituents from Solidago virga-aurea var. gigantea MIQ.

Activity-guided fractionation of the whole plant of Solidago virga-aurea var. gigantea M(IQ). (Compositae) has led to the isolation of three cytotoxic compounds, erythrodiol-3-acetate (1), alpha-tocopherol-quinone (2), and trans-phytol (3) from the hexane soluble fraction. It is the first report of those compounds from the genus.

Antineoplastic Agents↗

Four major saponins from Solidago canadensis.

Four new bisdesmosidic saponins each containing eight carbohydrate units were isolated from Solidago canadensis. GC, GC-MS, FABMS analysis and mainly the use of 2D NMR techniques allowed their identification as bayogeninglycosides (canadensissaponins 1-4) 3-O- [beta-D-glucopyranosyl-(1----3)-beta-D-glucopyranosyl]-28-O-[alpha-L- rhamnopyranosyl-(1----3)-beta-D-xylopyranosyl-(1----4)-[beta-D- xylopyranosyl-(1----3)]-alpha-L-rhamnopyranosyl-(1----2)-[beta-D- apio-D-furanosyl-(1----3)]-beta-D-6-deoxyglucopyranosyl- (1----]-bayogenin; -(1----2)-[beta-D-apio-D-furanosyl-(1----3)]-ara- binopyranosyl-(1----]-bayogenin; -[alpha-L-rhamnopyranosyl-(1----3)]-beta- D-6-deoxyglucopyranosyl-(1----]-bayogenin and - [alpha-L-rhamnopyranosyl- (1----3)]-arabinopyranosyl-(1----]-bayogenin.

Carbohydrate Sequence↗

Virgaureasaponin 3, a 3,28-bisdesmosidic triterpenoid saponin from Solidago virgaurea.

A new 3,28-bisdesmosidic triterpenoid glycoside was isolated from the mixture of deacylated saponins from the aerial parts of Solidago virgaurea. The structure of virgaureasaponin 3 was determined as 3-O-beta-D-glucopyranosyl-(1----3)-beta-D-glucopyranosylpolygalacic++ + acid 28-O-beta-D-fucopyranosyl-(1----2)-alpha-L-rhamnopyranosyl-(1----3)-beta -D- xylopyranosyl-(1----4)-alpha-L-rhamnopyranosyl-(1----2)-beta-D-fucopyran oside mainly by various 2D NMR techniques.

Carbohydrate Sequence↗

Diterpenes from Solidago rugosa.

Investigation of the roots and aerial parts of Solidago rugosa afforded the known diterpenes kolavenol, hardwickiic acid, (-)-kaur-16-en-19-oic acid, (+)-manool, (+)-3 beta-hydroxymanool, manoyl oxide and ent-abietic acid. In addition, the new labdane diterpene (+)-18-tigloyloxymanool and four new ent-abietanes were obtained. The structures of all known and new compounds were elucidated by spectroscopic methods, especially high-field 1H and 13C NMR, and inverse 1H-13C-correlation techniques, as well as chemical transformations. Six diterpenes were tested against Mycobacterium tuberculosis and M. avium, but showed no significant activities with minimum inhibitory concentrations of > 100 micrograms ml-1.

Diterpenes↗

epi-Cubebanes from Solidago canadensis.

GC-MS of the essential oil prepared by hydrodistillation of the green parts of a specimen of Solidago canadensis collected near Katowice, Poland, revealed two new sesquiterpene hydrocarbons. Their EI mass spectra resembled the mass spectrum of beta-ylangene (1) but the retention indices of the new compounds differed markedly from this known compound. After isolation of the new compounds by preparative GC their investigation by one- and two-dimensional NMR techniques resulted in the identification of 6-epi-alpha-cubebene (2) (minor constituent, 1.5%) and 6-epi-beta-cubebene (3) (major constituent, 20.5%).

Asteraceae↗

Composition and antifungal activity of the essential oil of Solidago chilensis.

Volatile constituents of the essential oils from leaves and inflorescences of Solidago chilensis Meyen were analyzed by GC-FID, GC-MS and 13C-NMR and thirty-six different compounds were identified. Pumiloxide, an unusual labdane diterpene, was found to be one of the major components in both oils (15.3 % and 12.3 %, respectively). Other important constituents were limonene and several sesquiterpenes, mainly gamma-cadinene. The antifungal activity of the leaf oil was assayed against five different strains of filamentous fungi and one yeast. Paper disk agar diffusion test showed human pathogenic dermatophytes to be the most sensitive.

Antifungal Agents↗

The main saponins from the aerial parts and the roots of Solidago virgaurea subsp. virgaurea.

Two new (3, 4) and two known (1, 2) genuine acylated bisdesmosidic triterpenoid glycosides of polygalacic acid (2 beta, 3 beta, 16 alpha, 23-tetrahydroxyolean-12-en-28-oic acid) were isolated from the aerial parts, as well as from the roots, of Solidago virgaurea L. subsp. virgaurea. The structures of these esters were elucidated as 4-O-fucopyranosyl-acylated compounds (1, 2, 3, 4) of 28-[O-alpha-L-rhamnopyranosyl-(1-->3)-O-beta-D-xylopyranosyl- (1-->4)-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranosyl]-glycosid es of 3-O-[beta-D-glucopyranosyl]-polygalacic acid (5), and 3-O-[O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl]- polygalacic acid (6).

Carbohydrate Sequence↗

Analysis of the Essential Oil of Solidago canadensis.

The analysis of the volatile compounds in the essential oil of SOLIDAGO CANADENSISL. sensu lato (Compositae) GC and GC-MS demonstrated the presence of at least 36 compounds, 18 of which were identified. The Major comonenets are gamma (2)- and delta-cadinenes.

Journal Article↗

[Isolation and structure elucidation of further new saponins from Solidago canadensis].

Four new main saponins (canadensis-saponins 5-8) (compounds 5-8) were isolated from Solidago canadensis L. (Asteraceae). Using GC/MS, FAB-MS, and mainly 2D-NMR techniques their structures were identified as 3-O-[beta-D-glucopyranosyl(1----3)-beta-D- glucopyranosyl]-28-O-[beta-D-galactopyranosyl(1----2)-alpha-L- rhamnopyranosyl-(1----3)-beta-D-xylopyranosyl-(1----4)-[beta-D- xylopyranosyl-(1----3)]-alpha-L-rhamnopyranosyl-(1----2)-[beta-D-apio -D- furanosyl-(1----3)]-beta-D-6-deoxyglucopyranosyl-(1----)]-bayog enin(5),3-O- [beta-D-glucopyranosyl-(1----3)-beta-D-glucopyranosyl]-28-O-[beta-D- galactopyranosyl-(1----2)-alpha-L-rhamnopyranosyl-(1----3)-beta-D- xylopyranosyl-(1----4)-[beta-D-xylopyranosyl-(1----3)]-alpha-L- rhamnopyranosyl-(1----2)-[beta-D-apio-D-furanosyl-(1----3)]- arabinopyranosyl-(1----)]bayogenin(6),3-O-[beta-D-glucopy ran osyl-(1----3)- beta-D-glucopyranosyl]-28-O-[beta-D-galactopyranosyl-(1----2)- alpha-L-rhamnopyranosyl-(1----3)-beta-D-xylopyranosyl-(1----4)-[beta-D- xylopyranosyl-(1----3)]-alpha-L-rhamnopyranosyl-(1----2)-[alpha-L- rhamnopyranosyl-(1----3)]-beta-D-6-deoxyglucopyranosyl-(1----)]-++ +bayogenin (7), and 3-O-[beta-D-glucopyranosyl-(1----3)-beta-D-glucopyranosyl]-28-[O- beta-D-galactopyranosyl-(1----2)-alpha-L-rhamnopyranosyl-(1----3)-beta-D - xylopyranosyl-(1----4)-[beta-D-xylopyranosyl-(1----3)]-alpha-L- rhamnopyranosyl-(1----2)-[alpha-L-rhamnopyranosyl-(1----3)]arabinopyr anosyl - (1----)[-bayogenin (8).

Carbohydrate Sequence↗