Anthraquinone Glycosides Research Articles

Notes: Determination of the Cytotoxicity of Rumex crispus during the Vegetation Period Using a Brine Shrimp Bioassay

The percentage of anthraquinone glycosides in the roots of Rumex crispus L. (Polygonaceae) is significantly greater than in other parts of the plant. The roots of R. crispus in different vegetation stages were investigated with regard to anthraquinone glycoside content. Their toxicity towards shrimp were also tested during the vegetation period. The data showed that the percentage of anthraquinone glycosides as well as the toxic effect on the shrimp increased during the vegetation period.

Excessively High Cell Proliferation in Sigmoid Colon After an Oral Purge With Anthraquinone Glycosides

Excessively High Cell Proliferation in Sigmoid Colon After an Oral Purge With Anthraquinone Glycosides

An anthraquinone glycoside from Cassia angustifolia leaves

Extraction of the leaves of Cassia angustifolia afforded a new anthraquinone glycoside, emodin 8- O-sophoroside together with seven known glycos

Concentrations of Anthraquinone Glycosides of Rumex crispus during Different Vegetation Stages

The anthraquinone glycoside contents of various parts of Rumex crispus L. (Polygonaceae) in different vegetation stages were investigated by thin layer chromatographic and spectro-photometric methods. The data showed that the percentage of anthraquinone glycoside in all parts of plant increased at each stage. Anthraquinone glycoside content was increased in leaf, stem, fruit and root from 0.05 to 0.40%, from 0.03 to 0.46%, from 0.08 to 0.34%, and from 0.35 to 0.91% respectively. From the roots of R. crispus, emodin-8-glucoside, RGA (isolated in our laboratory, its structure was not elucidated), traceable amount of glucofrangulin B and an unknown glycoside (Rf = 0.28 in ethyl acetate:m ethanol:water/100:20:10) was detected in which the concentration was increased from May to August. The other parts of plant contained only emodin-8-glucoside

Antiplatelet constituents of formosan Rubia akane.

A known steroid, in addition to triterpenoids, anthraquinones, naphthalenes and a new anthraquinone glycoside, xanthopurpurin 3-O-beta-D-glucoside, were isolated from the roots of Rubia akane grown in Taiwan. Mollugin, a naphthohydroquinone, showed strong inhibition of arachidonic acid (AA)-induced and collagen-induced platelet aggregation. In contrast, 2-methyl-1,3,6-trihydroxyl-9,10-anthraquinone, xanthopurpurin 3-O-beta-D-glucoside, and xanthopurpurin showed mainly strong inhibition of collagen-induced platelet aggregation.

Anthraquinone and naphthalene glycosides from Rhamnus nakaharai

A new anthraquinone glycoside and a new naphthalene glycoside have been isolated from the root bark of Rhamnus nakaharai. These compounds have been characterized as chrysophanol 8- O-xylosyl-(1 → 6)-glucoside and 2-acetyl-3-methyl-6-methoxynaphthalene-1,8-diol 8- O-xylosyl-(1 → 6)-glucoside, respectively.

Reassessment of the structure of an anthraquinone glycoside from Rhamnus formosana

The structure of an anthraquinone glycoside from Rhamnus formosana has been reinterpreted to be emodin 8- O-rhamnosyl-(1→2)-glucoside.

Cytotoxic anthraquinones from Rheum pulmatum

A new cytotoxic anthraquinone glucoside, pulmatin, 1,8-dihydroxy-3-methyl-anthraquinone-1- O-β- d-glucoside, and its congeners, chrysophanein and physcionin, have been isolated as minor components from the root of Rheum pulmatum, an Indonesian Jamu (medicinal plant) known as ‘kelembak’ by recycling high performance liquid chromatography (R-HPLC). These anthraquinone glycosides exhibited moderate cytotoxic activity against several types of carcinoma cells. Their structures were established by means of spectroscopic methods, in particular, the NMR data.

Formation of genotoxic metabolites from anthraquinone glycosides, present in Rubia tinctorum L.

Rubia tinctorum L., a medicinal plant used for the treatment of kidney and bladder stones, contains a characteristics spectrum of 9,10-anthraquinone derivatives, which are substituted in only one of the aromatic benzo rings. The majority of the anthraquinones present in the plant itself or in plant extracts are glycosides. We investigated the metabolism of two such glycosides, alizarinprimeveroside (AIP) and lucidinprimeveroside (LuP). AIP given orally to rats was metabolized to alizarin (Al) and 1-hydroxyanthraquinone (1-HA). The reductive cleavage of AlP was also observed after treatment of this compound with rat liver enzymes (S9) and NADHPH. 1-HA has been reported to induce unscheduled DNA synthesis (UDS) in primary rat hepatocytes (PRH) and intestinal and liver tumors in rats after chronic treatment. The in vitro genotoxicity of 1-HA was confirmed by our present investigations. We also observed that the glycoside AlP was active at inducing UDS in PRH, but the compound was inactive in the Salmonella/microsome assay. Oral administration of LuP to rats resulted in the excretion of lucidin and rubiadin. When LuP was treated with rat liver extract and NADPH, the compound was reduced to rubiadinprimeveroside (RuP), which was hydrolyzed to rubiadin. We have recently shown that lucidin is highly genotoxic in a battery of short-term tests. We now report that rubiadin is also highly genotoxic in Salmonella typhimurium. However, in contrast to lucidin, it requires metabolic activation. In the UDS assay in PRH, rubiadin was even more potent than lucidin and equal to the positive control DMBA. In addition, the glycoside LuP is active in the Salmonella/microsome assay as well as in the UDS assay. The present work demonstrates that the uptake of the anthraquinone glycosides AlP and LuP leads to the rodent carcinogen 1-HA, and to the highly genotoxic compounds lucidin and rubiadin. This extends our previous studies and supports our suggestion that the therapeutic use of Rubia tinctorum may involve a carcinogenic risk.

Flavonol and anthraquinone glycosides from Rhamnus formosana

Two new flavonol triglycosides, and a new anthraquinone glycoside, have been isolated from the roots of Rhamnus formosana. These compounds have been characterized as rhamnazin 3- O-[α- l-rhamopyranosyl(1→4)-α- l-rhamnopyranosyl(1→6)-β- d-galactopyranoside (rhamnazin 3-isorhamninoside), rhamnocitrin 3- O-isorhamninoside and 1,6,8-trihydroxy-3-methylanthraquinone 1- O-rhamnosyl(1→2)glucoside, respectively.

Potential Inhibitors of Platelet Aggregation from Plant Sources, V. Anthraquinones from Seeds of Cassia obtusifolia and Related Compounds

Three anthraquinone glycosides, gluco-obtusifolin [11], gluco-chryso-obtusin [15], and gluco-aurantioobtusin [13], were found to be platelet anti-aggregatory constituents of seeds of Cassia obtusifolia. Various other anthraquinone analogues were also tested, and their structure-activity relationships are discussed.

Anthraquinone glycosides from Rhamnus libanoticus

A new anthraquinone glycoside, physcion 8- O-β-rutinoside, has been isolated from the bark of Rhamnus libanoticus together with emodin, its 6- O-α- l-rhamnoside and 8- O-β- d-glucoside, and kaempferol.

Anthraquinones from Rhamnus formosana

A new anthraquinone glycoside has been isolated from the roots of Rhamnus formosana together with methyllinoleate, chrysophanol, physcion, β-sitosterol, emodin, frangulin B, and stigmasterol-β-d-glucoside. The new glycoside has been characterized as 1,8-dihydroxy-6-methoxy-3-methylanthraquinone 8-O-rhamnosyl-(1 → 2)-glucoside.

Anthraquinone glycosides from the seeds of Cassia tora

Three new anthraquinone glycosides, 1-[(β- d-glucopyranosyl-(1 → 3)- O-β- d-glucopyranosyl-(1 → 6)- O-β- d-glucopyranosyl)oxy]-8-hydroxy-3-methyl-9,10-anthraquinone, 1-[(β- d-glucopyranosyl-(1 → 6)- O-β- d-glucopyranosyl-(1 → 3)- O-β- d-glucopyranosyl-(1 → 6)- O-β- d-glucopyranosyl)oxy]-8-hydroxy-3-methyl-9,10-anthraquinone and 2-(β- d-glucopyranosyloxy)-8-hydroxy-3-methyl-1-methoxy-9,10-anthraquinone were isolated from the seeds of Cassia tora. Their structures were elucidated on the basis of chemical and spectral data. The first two compounds exhibited a weak protective effect on primary cultured hepatocytes against carbon tetrachloride toxicity.

Toxicity of the anthraquinone glycoside P-1894B for human skin fibroblasts.

P-1894B inhibits prolyl hydroxylase in vitro and has been proposed as a topical treatment for dermal fibrosis. The drug had similar effects on two fibroblast lines from normal human skin and one line from a patient with lichen sclerosus et atrophicus. Exposure of logarithmically-growing cell monolayers for 72 h caused dose-dependent inhibition of proliferation at 0.05-0.5 microgram/ml but time-dependent cell death at 1-50 micrograms/ml. The epithelial cell line NCTC 2544 gave a similar result. Collagen lattices containing normal fibroblasts contracted more slowly in the presence of the drug at 0.1-0.5 microgram/ml, but this was clearly related to loss of viability. Collagen synthesis by monolayer cultures was unaffected at 0.05 and 0.1 microgram/ml P-1894B in one line of normal fibroblasts, but was reduced by 40% and 15%, respectively, in the other. The concentrations of P-1894B reported to be active against prolyl hydroxylase are therefore lethal to cultured skin cells. Although the effective use of dithranol as a topical anti-psoriatic agent, despite its cytotoxicity in vitro, is encouraging for P-1894B, further toxicological studies are imperative.

Investigations on DNA binding in rat liver and in Salmonella and on mutagenicity in the Ames test by emodin, a natural anthraquinone

Emodin (1,6,8-trihydroxy-3-methylanthraquinone), an important aglycone found in natural anthraquinone glycosides frequently used in laxative drugs, was mutagenic in the Salmonella/mammalian microsome assay (Ames test) with a specificity for strain TA1537. The mutagenic activity was activation-dependent with an optimal amount of S9 from Aroclor 1254-treated male Sprague-Dawley rats of 20% in the S9 mix (v/v) for 10 μg emodin per plate. Heat inactivation of the S9 for 30 min at 60°C prevented mutagenicity. The addition of the cytochrome P-448 inhibitor 7,8-benzoflavone (18.5 nmoles per plate) reduced the mutagenic activity of 5.0 μg emodin per plate to about one third, whereas the P-450 inhibitor metyrapone (up to 1850 nmoles per plate) was without effect. To test whether a metabolite binds covalently to Salmonella DNA, [10- 14C]emodin was radiosynthesized, large batches of bacteria were incubated with [10- 14C]emodin and DNA was isolated. [G- 3H]Aflatoxin B 1 (AFB 1) was used as a positive control mutagen known to act via DNA binding. DNA obtained after aflatoxin treatment could be purified to constant specific activity. With emodin, the specific activity of DNA did not remain constant after repeated precipitations so that it is unlikely that the mutagenicity of emodin is due to covalent interaction of a metabolite with DNA. The antioxidants vitamin C and E or glutathione did not reduce the mutagenicity. Emodin was also negative with strain TA102. Thus, oxygen radicals are probably not involved. When emodin was incubated with S9 alone for up to 50 h before heat-inactivation of the enzymes and addition of bacteria, the mutagenic activity did not decrease. It is concluded that the mutagenicity of emodin is due to a chemically stable, oxidized metabolite forming physico-chemical associations with DNA, possibly of the intercalative type. In order to check whether an intact mammalian organism might be able to activate emodin to a DNA-binding metabolite, radiolabelled emodin was administered by oral gavage to male SD rats and liver DNA was isolated after 72 h. Very little radioactivity was associated with the DNA. Considering that DNA radioactivity could also be due to sources other than covalent interactions, an upper limit for the covalent binding index, CBI = (μmoles chemical bound per moles DNA nucleotides)/(mmoles chemical administered per kg body weight) of 0.5 is deduced. This is 10 4 times below the CBI of AFB 1. The demonstration of a lack of covalent interaction with DNA both in Salmonella and in rat liver is discussed in terms of a reduced hazard posed by emodin as a mutagenic drug in use in humans.

Alternative formation of anthraquinones and lipoquinones in heterotrophic and photoautotrophic cell suspension cultures of Morinda lucida Benth.

Photoheterotrophic and photoautotrophic cell suspension cultures were raised from a callus tissue derived from a Morinda lucida Benth. plant (Rubiaceae). The cultures were characterized with regard to fresh weight, dry weight, cell number, pH, chlorophyll and quinoid natural products. The amount of lipoquinones (phylloquinone, α-tocopherol, plastoquinone, ubiquinone) isolated from the photoautotrophic cultures matched the amount detected in an intact leaf. Anthraquinone glycosides which are found in the roots of Morinda plants were not present in the photoautotrophic culture. The photoheterotrophic culture contained only trace amounts of these pigments. Abundant anthraquinone synthesis was observed when photoautotrophic and photoheterotrophic suspension cultures were transferred into darkness, provided sucrose was present in the medium. Induction of synthesis of anthraquinone pigments coincided with a rapid disappearance of lipoquinones from the culture. Thus, in the suspension culture, photoautotrophy correlates with lipoquinone synthesis and heterotrophy correlates with anthraquinone synthesis. This reflects the situation in the intact plants where lipoquinones are chloroplast-associated whereas anthraquinones occur in the roots.

A New anthraquinone Glycoside from the Stem Bark ofDiospyros discolor

A New anthraquinone Glycoside from the Stem Bark of<i>Diospyros discolor</i>

Studies on the constituents of the seeds of Cassia obtusifolia LINN. The structures of two new anthraquinone glycosides.

Two new anthraquinones, alaternin 1-O-β-D-glucopyranoside and chryso-obtusin 2-O-β-D-glucopyranoside, were isolated, along with physcion 8-O-β-D-glucopyranoside, from the seeds of Cassia obtusifolia LINN., and their structures were established on the basis of spectral and chemical evidence.

An anthraquinone glycoside from Rhamnus pallasii

A new anthraquinone glycoside, together with α-sorinin, has been isolated from the bark of Rhamnus pallasii and its structure elucidated as physc