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Maike Petersen - One of the best experts on this subject based on the ideXlab platform.
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cloning and characterisation of Rosmarinic Acid synthase from melissa officinalis l
Phytochemistry, 2011Co-Authors: Corinna Weitzel, Maike PetersenAbstract:Lemon balm (Melissa officinalis L.; Lamiaceae) is a well-known medicinal plant mainly due to two groups of compounds, the essential oil and the phenylpropanoid derivatives. The prominent phenolic compound is Rosmarinic Acid (RA), an ester of caffeic Acid and 3,4-dihydroxyphenyllactic Acid. RA shows a number of interesting biological activities. Rosmarinic Acid synthase (RAS; 4-coumaroyl-CoA:hydroxyphenyllactic Acid hydroxycinnamoyltransferase) catalyses the ester formation. Cell cultures of M. officinalis have been established in order to characterise the formation of RA in an important diploid medicinal plant. RAS activity as well as the expression of the RAS gene are closely correlated with the accumulation of RA in suspension cultures of M. officinalis. The RAS cDNA and gene (MoRAS) were isolated. The RAS gene was shown to be intron-free. MoRAS belongs to the BAHD superfamily of acyltransferases. Southern-blot analysis suggests the presence of only one RAS gene copy in the M. officinalis genome. The enzyme was characterised with respect to enzyme properties, substrate preferences and kinetic data in crude plant extracts and as heterologously synthesised protein from Escherichia coli.
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cDNA cloning and functional characterisation of CYP98A14 and NADPH:cytochrome P450 reductase from Coleus blumei involved in Rosmarinic Acid biosynthesis
Plant Molecular Biology, 2009Co-Authors: David Eberle, Pascaline Ullmann, Danièle Werck-reichhart, Maike PetersenAbstract:The final reactions of Rosmarinic Acid biosynthesis, the introduction of the aromatic 3- and 3′-hydroxyl groups, are catalysed by cytochrome P450-dependent hydroxylases. The cDNAs encoding CYP98A14 as well as a NADPH:cytochrome P450 reductase (CPR) were isolated from Coleus blumei and actively expressed in Saccharomyces cerevisiae . The CYP98A14-cDNA showed an open reading frame of 1521 nucleotides with high similarities to 4-coumaroylshikimate/quinate 3-hydroxylases. Yeast microsomes harbouring the CYP98A14 protein catalysed the 3-hydroxylation of 4-coumaroyl-3′,4′-dihydroxyphenyllactate and the 3′-hydroxylation of caffeoyl-4′-hydroxyphenyllactate, in both cases forming Rosmarinic Acid. Apparent K _m-values for 4-coumaroyl-3′,4′-dihydroxyphenyllactate and caffeoyl-4′-hydroxyphenyllactate were determined to be at 5 μM and 40 μM, respectively. CYP98A14 differs from CYP98s from other plants, since 4-coumaroylshikimate or -quinate were not accepted as substrates. Coexpression of the Coleus blumei CPR and CYP98A14 in the same yeast cells increased the hydroxylation activity up to sevenfold. CYP98A14 from Coleus blumei is a novel bifunctional cytochrome P450 specialised for Rosmarinic Acid biosynthesis.
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production of Rosmarinic Acid and a new Rosmarinic Acid 3 o beta d glucoside in suspension cultures of the hornwort anthoceros agrestis paton
Planta, 2006Co-Authors: Katharina Vogelsang, Bernd Schneider, Maike PetersenAbstract:Cell suspension cultures of the hornwort Anthoceros agrestis Paton (Anthocerotaceae) were cultivated and characterized in CB-media containing 2 and 4% sucrose. The suspension cells accumulated Rosmarinic Acid up to 5.1% of the cell dry weight as well as caffeoyl-4′-hydroxyphenyllactate. Moreover, a more hydrophilic compound was detected which was isolated and identified as Rosmarinic Acid 3′-O-β-D-glucoside, a new Rosmarinic Acid derivative. This new Rosmarinic Acid derivative was found up to 1.0% of the cell dry weight in suspension cells of A. agrestis.
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Fungal elicitor preparations and methyl jasmonate enhance Rosmarinic Acid accumulation in suspension cultures of Coleus blumei
Plant Cell Reports, 1999Co-Authors: E. Szabo, A. Thelen, Maike PetersenAbstract:Suspension cultures of Coleus blumei (Lamiaceae) treated with either an elicitor preparation from the culture medium of the phytopathogenic oomycete Pythium aphanidermatum or with methyl jasmonate enhanced accumulation of Rosmarinic Acid approximately threefold. The specific activities of phenylalanine ammonia lyase and Rosmarinic Acid synthase were also enhanced after addition of the fungal elicitor. The addition of methyl jasmonate transiently increased activities of phenylalanine ammonia lyase and hydroxyphenylpyruvate reductase, whereas the activity of Rosmarinic Acid synthase was not stimulated and the activity of tyrosine aminotransferase was slightly and constantly enhanced. Methyl jasmonate stimulated Rosmarinic Acid accumulation not only when added directly to the culture medium, but also when it could reach the cells only via the gas phase.
Saleh Alwasel - One of the best experts on this subject based on the ideXlab platform.
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Rosmarinic Acid inhibits some metabolic enzymes including glutathione s transferase lactoperoxidase acetylcholinesterase butyrylcholinesterase and carbonic anhydrase isoenzymes
Journal of Enzyme Inhibition and Medicinal Chemistry, 2016Co-Authors: Ilhami Gulci, Andrea Scozzafava, Claudiu T Supura, Zeynep Koksal, Fikre Turka, Songul Cetinkaya, Zeynebe Ingol, Zubeyi Huyu, Saleh AlwaselAbstract:Rosmarinic Acid (RA) is a natural polyphenol contained in many aromatic plants with promising biological activities. Carbonic anhydrases (CAs, EC 4.2.1.1) are widespread and intensively studied metalloenzymes present in higher vertebrates. Acetylcholinesterase (AChE, E.C. 3.1.1.7) is intimately associated with the normal neurotransmission by catalysing the hydrolysis of acetylcholine to acetate and choline and acts in combination with butyrylcholinesterase (BChE) to remove acetylcholine from the synaptic cleft. Lactoperoxidase (LPO) is an enzyme involved in fighting pathogenic microorganisms, whereas glutathione S-transferases (GSTs) are dimeric proteins present both in prokaryotic and in eukaryotic organisms and involved in cellular detoxification mechanisms. In the present study, the inhibition effects of Rosmarinic Acid on tumour-associated carbonic anhydrase IX and XII isoenzymes, AChE, BChE, LPO and GST enzymes were evaluated. Rosmarinic Acid inhibited these enzymes with Kis in the range between micromolar to picomolar. The best inhibitory effect of Rosmarinic Acid was observed against both AChE and BChE.
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Rosmarinic Acid inhibits some metabolic enzymes including glutathione s transferase lactoperoxidase acetylcholinesterase butyrylcholinesterase and carbonic anhydrase isoenzymes
Journal of Enzyme Inhibition and Medicinal Chemistry, 2016Co-Authors: Ilhami Gulcin, Andrea Scozzafava, Zeynep Koksal, Songul Cetinkaya, Claudiu T Supuran, Fikret Turkan, Zeynebe Bingol, Zubeyir Huyut, Saleh AlwaselAbstract:AbstractRosmarinic Acid (RA) is a natural polyphenol contained in many aromatic plants with promising biological activities. Carbonic anhydrases (CAs, EC 4.2.1.1) are widespread and intensively studied metalloenzymes present in higher vertebrates. Acetylcholinesterase (AChE, E.C. 3.1.1.7) is intimately associated with the normal neurotransmission by catalysing the hydrolysis of acetylcholine to acetate and choline and acts in combination with butyrylcholinesterase (BChE) to remove acetylcholine from the synaptic cleft. Lactoperoxidase (LPO) is an enzyme involved in fighting pathogenic microorganisms, whereas glutathione S-transferases (GSTs) are dimeric proteins present both in prokaryotic and in eukaryotic organisms and involved in cellular detoxification mechanisms. In the present study, the inhibition effects of Rosmarinic Acid on tumour-associated carbonic anhydrase IX and XII isoenzymes, AChE, BChE, LPO and GST enzymes were evaluated. Rosmarinic Acid inhibited these enzymes with Kis in the range betw...
Sang Un Park - One of the best experts on this subject based on the ideXlab platform.
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Molecular cloning and characterization of Rosmarinic Acid biosynthetic genes and Rosmarinic Acid accumulation in Ocimum basilicum L.
'Elsevier BV', 2019Co-Authors: Do Yeon Kwon, Jae Kwang Kim, Sang Un ParkAbstract:We have aimed to investigate the expression of genes related to Rosmarinic Acid (RA) synthesis and Rosmarinic Acid content in 2 Ocimum basilicum cultivars, green (cinnamon) and purple (red rubin) basil. Specifically, genes related to Rosmarinic Acid biosynthesis were cloned and characterized for O. basilicum. We obtained partial cDNAs of tyrosine aminotransferase (TAT) and 4-hydroxyphenylpyruvate reductase (HPPR), which were of 323 bp and 616 bp in size, respectively. The transcription levels of most genes related to Rosmarinic Acid synthesis were higher in green basil compared to purple basil, except for ObPAL and Ob4CL in the root. The highest expression was obtained in the leaves of green basil for all genes and the roots of purple basil for all genes, except for TAT. The highest Rosmarinic Acid content was obtained in the leaves of both cultivars, with higher RA accumulating in green basil compared to purple basil. The leaves had the highest RA content out of all plant organs, with the RA accumulation in the leaves of green basil being 1.64 times higher compared to purple basil. Further study is required to investigate whether a similar trend is observed across O. basilicum cultivars of different color types. Keywords: Rosmarinic Acid, Ocimum basilicum, Gene expression, Different organ
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yeast extract and silver nitrate induce the expression of phenylpropanoid biosynthetic genes and induce the accumulation of Rosmarinic Acid in agastache rugosa cell culture
Molecules, 2016Co-Authors: Woo Tae Park, Sook Young Lee, Mariadhas Valan Arasu, Naif Abdullah Aldhabi, Sun Kyung Yeo, Jin Jeon, Jongseok Park, Sang Un ParkAbstract:The present study aimed to investigate the role of yeast extract and silver nitrate on the enhancement of phenylpropanoid pathway genes and accumulation of Rosmarinic Acid in Agastache rugosa cell cultures. The treatment of cell cultures with yeast extract (500 mg/L) and silver nitrate (30 mg/L) for varying times enhanced the expression of genes in the phenylpropanoid pathway and the production of Rosmarinic Acid. The results indicated that the expression of RAS and HPPR was proportional to the amount of yeast extract and silver nitrate. The transcript levels of HPPR under yeast extract treatment were 1.84-, 1.97-, and 2.86-fold higher than the control treatments after 3, 6, and 12 h, respectively, whereas PAL expression under silver nitrate treatment was 52.31-fold higher than in the non-treated controls after 24 h of elicitation. The concentration of Rosmarinic Acid was directly proportional to the concentration of the applied elicitors. Yeast extract supplementation documented the highest amount of Rosmarinic Acid at 4.98 mg/g, whereas silver nitrate addition resulted in a comparatively lower amount of Rosmarinic Acid at 0.65 mg/g. In conclusion, addition of yeast extract to the cell cultures enhanced the accumulation of Rosmarinic Acid, which was evidenced by the expression levels of the phenylpropanoid biosynthetic pathway genes in A. rugosa.
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molecular cloning and characterization of tyrosine aminotransferase and hydroxyphenylpyruvate reductase and Rosmarinic Acid accumulation in scutellaria baicalensis
Natural Product Communications, 2014Co-Authors: Youngjung Kim, Yong Kyoung Kim, M R Uddina, C G Park, Sang Un ParkAbstract:Rosmarinic Acid (α-O-caffeoyl-3,4-dihydroxyphenylacetic Acid, RA) is a caffeoyl ester widely distributed in plants. cDNA clones encoding tyrosine aminotransferase (TAT1 and 2) and hydroxyphenylpyru...
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Accumulation of Tilianin and Rosmarinic Acid and Expression of Phenylpropanoid Biosynthetic Genes in Agastache rugosa
2012Co-Authors: Pham Anh Tuan, Woo Tae Park, Nam Il Park, Sang Un ParkAbstract:Korean mint (Agastache rugosa), a perennial, medicinal plant of the Labiatae family, has many useful constituents, including monoterpenes and phenylpropanoids. Among these, tilianin and Rosmarinic Acid, 2 well-known natural products, have many pharmacologically useful properties. Chalcone synthase (CHS) and chalcone isomerase (CHI) catalyze the first and second committed steps in the phenylpropanoid pathway of plants, leading to the production of tilianin. In this study, cDNAs encoding CHS (ArCHS) and CHI (ArCHI) were isolated from A. rugosa using rapid amplification of cDNA ends (RACE)-PCR. Amino Acid sequence alignments showed that ArCHS and ArCHI shared high sequence identity and active sites with their respective orthologous genes. Quantitative real-time PCR analysis was used to determine the expression levels of genes involved in tilianin and Rosmarinic Acid biosyntheses in the flowers, leaves, stems, and roots of A. rugosa. High-performance liquid chromatography (HPLC) revealed that the accumulation pattern of tilianin matched the expression patterns of ArCHS and ArCHI in different organs of A. rugosa. Moreover, acacetin, the precursor of tilianin, also demonstrated an accumulation pattern congruent with the expression of these 2 genes. The transcription levels of ArPAL, ArC4H, and Ar4CL were the highest in the leaves or flowers of the plant, which also contained a relatively high amount of Rosmarinic Acid. However, the roots showed a significant content of Rosmarinic Acid, although the transcription of ArPAL, ArC4H, and Ar4CL were low. The findings of our study support the medicinal usefulness of A. rugosa and indicate targets for increasing tilianin and Rosmarinic Acid production in this plant
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Rosmarinic Acid production in hairy root cultures of agastache rugosa kuntze
World Journal of Microbiology & Biotechnology, 2008Co-Authors: Sook Young Lee, Yong Kyung Kim, Sang Un ParkAbstract:Rosmarinic Acid, an important phenolic active compound, is one of the main active constituents of Agastache rugosa Kuntze and has astringent properties, antioxidant capacity, anti-inflammatory activity, antimutagenic ability, antimicrobial capacity, and antiviral properties. To investigate in vitro production of Rosmarinic Acid, we established a hairy root culture of A. rugosa by infecting leaf and stem explants with Agrobacterium rhizogenes R1000, and tested the growth and Rosmarinic Acid production of these cultures. Hairy roots were cultured in Murashige and Skoog liquid medium and maximum growth (14.1 g dry wt/l) was attained after 14 days of culture, at which time the content of Rosmarinic Acid was 116 mg/g dry wt. The present results demonstrate that hairy root culture of A. rugosa is a valuable alternative approach for the production of Rosmarinic Acid.
Bruno Sarmento - One of the best experts on this subject based on the ideXlab platform.
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Chitosan-based nanoparticles for Rosmarinic Acid ocular delivery--In vitro tests.
International Journal of Biological Macromolecules, 2015Co-Authors: Sara Baptista Da Silva, Manuela Pintado, Domingos Ferreira, Bruno SarmentoAbstract:Abstract In this study, chitosan nanoparticles were used to encapsulate antioxidant Rosmarinic Acid, Salvia officinalis (sage) and Satureja montana (savory) extracts as Rosmarinic Acid natural vehicles. The nanoparticles were prepared by ionic gelation using chitosan and sodium tripolyphosphate (TPP) in a mass ratio of 7:1, at pH 5.8. Particle size distribution analysis and transmission electron microscopy (TEM) confirmed the size ranging from 200 to 300 nm, while surface charge of nanoparticles ranged from 20 to 30 mV. Nanoparticles demonstrate to be safe without relevant cytotoxicity against retina pigment epithelium (ARPE-19) and human cornea cell line (HCE-T). The permeability study in HCE monolayer cell line showed an apparent permeability coefficient Papp of 3.41 ± 0.99 × 10−5 and 3.24 ± 0.79 × 10−5 cm/s for Rosmarinic Acid loaded chitosan nanoparticles and free in solution, respectively. In ARPE-19 monolayer cell line the Papp was 3.39 ± 0.18 × 10−5 and 3.60 ± 0.05 × 10−5 cm/s for Rosmarinic Acid loaded chitosan nanoparticles and free in solution, respectively. Considering the mucin interaction method, nanoparticles indicate mucoadhesive proprieties suggesting an increased retention time over the ocular mucosa after instillation. These nanoparticles may be promising drug delivery systems for ocular application in oxidative eye conditions.
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characterization of solid lipid nanoparticles produced with carnauba wax for Rosmarinic Acid oral delivery
RSC Advances, 2015Co-Authors: Ana Raquel Madureira, Bruno Sarmento, Debora A Campos, Pedro Fonte, Sara Nunes, Flavio Reis, A Gomes, Maria Manuela PintadoAbstract:In the last decade, research studies have increased on the development of delivery systems for polyphenols, for protection, improvement of stability and increase of their bioavailability. Rosmarinic Acid is a polyphenol with described bioactivities, such as antioxidant, anti-mutagenic, anti-bacterial and anti-viral capabilities. Thus, the aim of this research work was to produce stable solid lipid nanoparticles (SLN) using carnauba wax as lipidic matrix, for delivery of Rosmarinic Acid, to be further incorporated into food matrices. Hence, different concentrations of wax (0.5, 1 and 1.5%, w/v) and percentages of surfactant (1, 2 and 3%, v/v) were tested. Physical properties, surface morphology and association efficiencies were studied at time of production and after 28 day at refrigerated storage. Thermal properties and the nature of the chemical interactions between the lipids waxes and Rosmarinic Acid were also evaluated. The particles showed range size between 35–927 nm and zeta potentials of ca. −38 to 40, showing high stability, with no risk of aggregation due to electric repulsion of SLN. High association efficiencies % (ca. 99%) were obtained. FTIR analyses proved the association of Rosmarinic Acid and lipidic matrix. The low lipid and high surfactant concentrations leads to small SLN. The surfactant, polysorbate 80 decreases the interfacial tension in the SLN surfaces, preventing aggregation, leading to the development of small particles. These properties were maintained throughout the 28 day of refrigerated storage, and no Rosmarinic Acid was released by the particles during refrigeration, indicating good compatibility between Rosmarinic Acid and the waxy core of SLN. The optimum range values to obtain the desirable features for incorporation in a functional food suggest formulations containing 1.0 and 1.5% (w/v) of lipid and 2% (v/v) of surfactant.
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protective effects of lavandula viridis l her extracts and Rosmarinic Acid against h2o2 induced oxidative damage in a172 human astrocyte cell line
Industrial Crops and Products, 2013Co-Authors: Patricia Costa, Bruno Sarmento, Sandra Goncalves, Anabela RomanoAbstract:Abstract We investigated the neuroprotective effect of Lavandula viridis extracts (infusion, water:ethanol and methanol) and Rosmarinic Acid, the major compound present in the extracts, against oxidative damage induced by hydrogen peroxide (H 2 O 2 ) in A172 human astrocyte cell line regarding the neurotoxic effect, intracellular reactive oxygen species (ROS) production and the activity of the antioxidant enzyme catalase (CAT). We found that L. viridis extracts and Rosmarinic Acid protected A172 astrocytes against H 2 O 2 and reduced intracellular ROS accumulation. Furthermore, the protection effect was not caused by modulation of CAT suggesting that other intracellular mechanisms are involved in the neuroprotective effect. Our results highlight that L. viridis extracts and Rosmarinic Acid have beneficial effects against oxidative damage associated with neurodegenerative diseases.
Marisa Freitas - One of the best experts on this subject based on the ideXlab platform.
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anti inflammatory effect of Rosmarinic Acid and an extract of rosmarinus officinalis in rat models of local and systemic inflammation
Basic & Clinical Pharmacology & Toxicology, 2015Co-Authors: Joao Rocha, Maria Eduardofigueira, Andreia Barateiro, Adelaide Fernandes, Dora Brites, Rosario Bronze, Catarina M M Duarte, Ana Teresa Serra, Rui Pinto, Marisa FreitasAbstract:Rosmarinic Acid is a polyphenolic compound and main constituent of Rosmarinus officinalis and has been shown to possess antioxidant and anti-inflammatory properties. We aimed to evaluate the anti-inflammatory properties of Rosmarinic Acid and of an extract of R. officinalis in local inflammation (carrageenin-induced paw oedema model in the rat), and further evaluate the protective effect of Rosmarinic Acid in rat models of systemic inflammation: liver ischaemia-reperfusion (I/R) and thermal injury models. In the local inflammation model, Rosmarinic Acid was administered at 10, 25 and 50 mg/kg (p.o.), and the extract was administered at 10 and 25 mg/kg (equivalent doses to Rosmarinic Acid groups) to male Wistar rats. Administration of Rosmarinic Acid and extract at the dose of 25 mg/kg reduced paw oedema at 6 hr by over 60%, exhibiting a dose-response effect, suggesting that Rosmarinic was the main contributor to the anti-inflammatory effect. In the liver I/R model, Rosmarinic Acid was administered at 25 mg/kg (i.v.) 30 min. prior to the induction of ischaemia and led to the significant reduction in the serum concentration of transaminases (AST and ALT) and LDH. In the thermal injury model, Rosmarinic Acid was administered at 25 mg/kg (i.v.) 5 min. prior to the induction of injury and significantly reduced multi-organ dysfunction markers (liver, kidney, lung) by modulating NF-κB and metalloproteinase-9. For the first time, the anti-inflammatory potential of Rosmarinic Acid has been identified, as it causes a substantial reduction in inflammation, and we speculate that it might be useful in the pharmacological modulation of injuries associated to inflammation.
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anti inflammatory effect of Rosmarinic Acid and an extract of rosmarinus officinalis in rat models of local and systemic inflammation
Basic & Clinical Pharmacology & Toxicology, 2015Co-Authors: Joao Rocha, Maria Eduardofigueira, Andreia Barateiro, Adelaide Fernandes, Dora Brites, Rosario Bronze, Catarina M M Duarte, Ana Teresa Serra, Rui Pinto, Marisa FreitasAbstract:Rosmarinic Acid is a polyphenolic compound and main constituent of Rosmarinus officinalis and has been shown to possess antioxidant and anti-inflammatory properties. We aimed to evaluate the anti-inflammatory properties of Rosmarinic Acid and of an extract of R. officinalis in local inflammation (carrageenin-induced paw oedema model in the rat), and further evaluate the protective effect of Rosmarinic Acid in rat models of systemic inflammation: liver ischaemia-reperfusion (I/R) and thermal injury models. In the local inflammation model, Rosmarinic Acid was administered at 10, 25 and 50 mg/kg (p.o.), and the extract was administered at 10 and 25 mg/kg (equivalent doses to Rosmarinic Acid groups) to male Wistar rats. Administration of ros- marinic Acid and extract at the dose of 25 mg/kg reduced paw oedema at 6 hr by over 60%, exhibiting a dose-response effect, suggesting that Rosmarinic was the main contributor to the anti-inflammatory effect. In the liver I/R model, Rosmarinic Acid was administered at 25 mg/kg (i.v.) 30 min. prior to the induction of ischaemia and led to the significant reduction in the serum con- centration of transaminases (AST and ALT) and LDH. In the thermal injury model, Rosmarinic Acid was administered at 25 mg/ kg (i.v.) 5 min. prior to the induction of injury and significantly reduced multi-organ dysfunction markers (liver, kidney, lung) by modulating NF-jB and metalloproteinase-9. For the first time, the anti-inflammatory potential of Rosmarinic Acid has been identified, as it causes a substantial reduction in inflammation, and we speculate that it might be useful in the pharmacological modulation of injuries associated to inflammation. Rosmarinus officinalis L., popularly named rosemary, has been used in folk medicine with several pharmacological effects being associated to its consumption, including its anti- inflammatory effects (1,2), and Rosmarinic Acid (RA) is one of its main phenolic compounds (3). Two studies have evaluated the kinetics of Rosmarinic Acid when administered orally to rats (4,5). These studies showed that Rosmarinic Acid was readily absorbed in the gastrointestinal tract (according to Konishi and Kobayashi (6), it crosses intestinal epithelium by passive diffusion) and reaches the peak plasma concentration at 0.5 hr post-admin- istration. Metabolites formed are a result of glucuronidation, sulphation and methylation of Rosmarinic Acid and are then eliminated in the urine. The effect of R. officinalis and ros- marinic Acid on metabolizing enzymes was also studied in Wistar rats (7). This study demonstrated that the extract of R. officinalis was able to induce the enzymes CYP1A1, CYP2B1/2, CYP2E1, glutathione S-transferase and UDP-glu- curonosyl transferase, but this effect was not observed when Rosmarinic Acid was administered alone. The authors have attributed this effect to the presence of flavones and
