lignans and rabdosiin

Symphytum officinale L. (comfrey, Boraginaceae) is a cultivated or spontaneously growing medicinal plant that is traditionally used for the treatment of bone fractures, hematomas, muscle pains and joint pains. A wide range of topical preparations and dried roots for ex tempore applications are marketed in European drug stores or pharmacies.. The aim of this study was to perform the qualitative and quantitative analysis of pyrrolizidine alkaloids (PAs) and phenolic compounds in the hydroethanolic extracts of 16 commercial comfrey root batches purchased from 12 different European countries.. Liquid chromatography hyphenated with high-resolution tandem mass spectrometry (LC-HRMS/MS) was used for the profiling of PAs and phenolic compounds, whereas LC-MS/MS and liquid chromatography with diode array detection (LC-DAD) were used for their quantification.. 20 PAs (i.e. intermedine, lycopsamine, acetylintermedine, acetyllycopsamine, symphytine, symphytine-N-oxide), 17 phenolic compounds (i.e. caffeic and rosmarinic acids, rabdosiin, globoidnan A, globoidnan B) and 9 nonphenolic compounds (sugars, organic and fatty acids) were fully or partly annotated in the analysed samples. In addition, the quantitative analyses revealed that globoidnan B, rabdosiin and globoidnan A are new phenolic markers that can be used together with rosmarinic acid and PAs for the quality control of commercial comfrey root batches.. This study brings new insights into the phytochemical complexity of S. officinale, revealing not only numerous toxic PAs, but also a significant number of valuable phenolic compounds that could contribute to the bioactivities of comfrey-based preparations.

Topics: Caffeic Acids; Chromatography, Liquid; Comfrey; Europe; Lignans; Plant Extracts; Plant Roots; Pyrrolizidine Alkaloids; Tandem Mass Spectrometry

Topics: Animals; Apoptosis; Caffeic Acids; Cells, Cultured; Hydrogen Peroxide; Lamiaceae; Lignans; Molecular Structure; Myocytes, Cardiac; Plant Extracts; Protective Agents; Rats; Spectrum Analysis

During an investigation of plant cell cultures that might be useful in the treatment of renal disorders, we established a vigorously-growing E-4 callus culture of Eritrichium sericeum that produced large amounts of caffeic acid metabolites, (-)-rabdosiin (1.8% dry wt) and rosmarinic acid (4.6% dry wt). Elicitation of the calli by methyl jasmonate induced a 38% increase in total polyphenol production. The most efficient method of eliciting (-)-rabdosiin biosynthesis was through the treatment of E-4 calli with cuprum glycerate, which induced an increase in (-)-rabdosiin production of as much as 4.1% dry wt. Oral administration of E-4 callus biomass (100 mg/kg/d for 30 d) to rats with induced Masugi-nephritis caused an increase in diuresis and lowered creatinine excretion and proteinuria levels as compared with Masugi-nephritis untreated rats. While all of the Masugi-nephritis untreated rats began to suffer, near a quarter of the E-4 treated rats remained in good health. This result indicates that the E-4 culture has the potential to alleviate the symptoms associated with nephritis.

Topics: Acetates; Animals; Biomass; Boraginaceae; Caffeic Acids; Cells, Cultured; Cinnamates; Copper; Creatinine; Cyclopentanes; Depsides; Diuresis; Glyceric Acids; Kinetics; Lignans; Molecular Structure; Nephritis; Oxylipins; Phytotherapy; Plant Growth Regulators; Proteinuria; Random Allocation; Rats; Rats, Sprague-Dawley; Rosmarinic Acid

Rabdosiin and related caffeic acid metabolites have been proposed as active pharmacological agents demonstrating potent anti-HIV and antiallergic activities. We transformed Eritrichium sericeum and Lithospermum erythrorhizon seedlings by the rolC gene, which has been recently described as an activator of plant secondary metabolism. Surprisingly, the rolC-transformed cell cultures of both plants yielded two- to threefold less levels of rabdosiin and rosmarinic acid (RA) than respective control cultures. This result establishes an interesting precedent when the secondary metabolites are differently regulated by a single gene. We show that the rolC gene affects production of rabdosiin and RA irrespective of the methyl jasmonate (MeJA)-mediated and the Ca(2+)-dependent NADPH oxidase pathways. Cantharidin, an inhibitor of serine/threonine phosphatases, partly diminishes the rolC-gene inhibitory effect that indicates involvement of the rolC-gene-mediated signal in plant regulatory controls, mediated by protein phosphatases. We also show that the control MeJA-stimulated E. sericeum root culture produces (-)-rabdosiin up to 3.41% dry weight, representing the highest level of this substance for plant cell cultures reported so far.

Topics: Boraginaceae; Caffeic Acids; Cantharidin; Cells, Cultured; Cinnamates; Depsides; Gene Expression Regulation, Plant; Genes, Bacterial; Lignans; Plant Roots; Plants, Genetically Modified; Rhizobium; Rosmarinic Acid; Transformation, Genetic

Lithospermum erythrorhizon cells cultured in pigment production (M-9) medium produced lithospermic acid B, a dimerized caffeic acid ester derivative, in quantities similar to the production of shikonin. The cells also produced a related dimer, (+)-rabdosiin. In Linsmaier-Skoog liquid medium, which suppresses shikonin production, both lithospermic acid B and (+)-rabdosiin were still formed. Lithospermic acid, a caffeic acid-rosmarinic acid conjugate, was isolated as a main constituent in Lithospermum hairy root cultures. In the aerial parts of L. erythrorhizon, the content of these phenylpropanoid oligomers was relatively low compared to that of rosmarinic acid.

Topics: Benzofurans; Caffeic Acids; Cells, Cultured; Depsides; Dimerization; Lignans; Magnetic Resonance Spectroscopy; Naphthoquinones; Plants

We examined the effects of caffeic acid-containing compounds such as chlorogenic acid, rosmarinic acid and rabdosiin on anti-allergic activities involving active oxygens scavenging activity as well as inhibitory activities of hyaluronidase and beta-hexosaminidase release. Rabdosiin exhibited the highest hyaluronidase-inhibitory activity and scavenging activities against active oxygens species such as superoxide anion radicals and hydroxyl radicals among the tested compounds. Both rabdosiin and caffeic acid inhibited beta-hexosaminidase release from cultured cells more than 90% at 2 mM. The inhibition by rosmarinic acid and chlorogenic acid were weaker than that of rabdosiin. From these results, rabdosiin has been proposed to possess anti-allergic activity.

Topics: Animals; Anti-Allergic Agents; beta-N-Acetylhexosaminidases; Caffeic Acids; Chlorogenic Acid; Cinnamates; Depsides; Electron Spin Resonance Spectroscopy; Enzyme Inhibitors; Free Radical Scavengers; Hyaluronoglucosaminidase; Hydroxyl Radical; Leukemia, Basophilic, Acute; Lignans; Rats; Rosmarinic Acid; Superoxides; Tumor Cells, Cultured