P.0293 Analgesic effect of the dry extract of satureja montana and the active compounds rosmarinic acid and carvacrol

Abstract: Novel 1,2,3-triazole-tethered N-norbuprenorphine derivatives with an OMe or OH group at the C3 position were synthesized alongside with evaluation of their analgesic properties. The analgesic activities of the resulting library were investigated via tail flick test in mice. Our results indicated that 10b and 10e were as effective as the starting compounds 8 and 9 with ED50 equal to 16.59 and 19.44 mg/kg, respectively. To investigate the effect of a methyl group at C3 on biological properties, the most active compounds were O-demethylated and their anti-nociceptive effects were assessed. The new O-demethylated derivatives (11b and 11e) showed better analgesic properties than the parent compounds with ED50 of 14.73 and 15.80 mg/kg, respectively. Naloxone prevented the analgesic effect of the synthesized compounds, indicating that the opioid receptors are highly involved in the anti-nociceptive effects of these. The potential dependency effects of the most potent derivatives were studied by condition place preference test in mice and compared to morphine and buprenorphine. Interestingly, 10b, 10e, 11b, and 11e did not show any dependency effect, similar to buprenorphine.

Download Full-text

Application of Deep Eutectic Solvents for the Extraction of Rutin and Rosmarinic Acid from Satureja montana L. and Evaluation of the Extracts Antiradical Activity

Plants ◽

10.3390/plants9020153 ◽

2020 ◽

Vol 9 (2) ◽

pp. 153 ◽

Cited By ~ 4

Author(s):

Martina Jakovljević ◽

Jelena Vladić ◽

Senka Vidović ◽

Kristian Pastor ◽

Stela Jokić ◽

...

Keyword(s):

Rosmarinic Acid ◽

High Performance ◽

Antiradical Activity ◽

Choline Chloride ◽

Extraction Procedure ◽

Principal Component ◽

Deep Eutectic Solvents ◽

Array Detector ◽

Specific Chemical ◽

Satureja Montana

Satureja montana L. was used in the current research as the plant exhibits numerous health-promoting benefits due to its specific chemical composition. The extraction method based on deep eutectic solvents (DESs) was used for the extraction of rutin and rosmarinic acid from this plant. Five different choline chloride-based DESs with different volumes of water (10%, 30%, and 50% (v/v)) were used for the extraction at different temperatures (30, 50, and 70 °C) to investigate the influence on rosmarinic acid and rutin content obtained by high-performance liquid chromatography with diode-array detector (HPLC-DAD) in the obtained extracts. A principal component analysis was employed to explore and visualize the influence of applied parameters on the efficiency of the extraction procedure of rutin and rosmarinic acid. Among the tested DESs, choline chloride:lactic acid (mole ratio 1:2) and choline chloride:levulinic acid (mole ratio 1:2) were the most suitable for the extraction of rutin, while for rosmarinic acid choline chloride:urea (mole ratio 1:2) was the most effective solvent. The extract showing the best antiradical activity was obtained with choline chloride:urea (mole ratio 1:1) at 30 °C and 50% H2O (v/v).

Download Full-text

Impact of Gelatin Supplemented with Gum Arabic, Tween 20, and β-Cyclodextrin on the Microencapsulation of Turkish Oregano Extract

Molecules ◽

10.3390/molecules24010176 ◽

2019 ◽

Vol 24 (1) ◽

pp. 176 ◽

Cited By ~ 4

Author(s):

Juste Baranauskaite ◽

Dalia M. Kopustinskiene ◽

Jurga Bernatoniene

Keyword(s):

Rosmarinic Acid ◽

Encapsulation Efficiency ◽

In Vitro Release ◽

Gum Arabic ◽

Product Yield ◽

Wall Material ◽

Tween 20 ◽

Active Compounds ◽

Vitro Release

Microencapsulation protects core materials from deteriorating due to environmental conditions, such as moisture or oxidation, and improves the bioavailability of active compounds, allowing one to make solid formulations from oils and increase their solubility. Wall and core material properties determine the microencapsulation efficiency and the best results are achieved when a wall material mixture is used to prepare the microcapsules. In this work, we optimized the wall material composition (gelatin supplemented with gum Arabic, Tween 20, and β-cyclodextrin) of Turkish oregano microcapsules prepared by spray-drying technology to increase the product yield, the encapsulation efficiency, and to achieve narrower particle size distribution. When the wall material solution contained 10 g of gelatin, 7.5 g of gum Arabic, 1.99 g of Tween 20, 1.98 g of β-cyclodextrin, and 20 g of ethanolic oregano extract, the encapsulation efficiency of oregano’s active compounds, rosmarinic acid and carvacrol, were 96.7% and 99.8%, respectively, and the product yield was 85.63%. The physicochemical properties, microscopic morphology, and in vitro release of the prepared microcapsules were characterized in the study. The use of gelatin as the main coating material, in supplementation with gum Arabic, Tween 20, and β-cyclodextrin, not only improved the encapsulation efficiency, but also increased the in vitro release of both main active compounds of Turkish oregano extract—rosmarinic acid and carvacrol.

Download Full-text

CHEMICAL COMPOSITION AND BIOLOGICAL ACTIVITY OF THE DRY EXTRACT "ROSMATIN" FROM THE HERB OF DRACOCEPHALUM MOLDAVICA L.

chemistry of plant raw material ◽

10.14258/jcprm.2021039161 ◽

2021 ◽

pp. 253-264

Author(s):

Olga Petrovna Sheychenko ◽

Vladimir Ivanovich Sheychenko ◽

Sergey Vladimirovich Goryainov ◽

Ekaterina Vladimirovna Zvezdina ◽

Elena Nikolaevna Kurmanova ◽

...

Keyword(s):

Rosmarinic Acid ◽

Quantitative Composition ◽

Standard Samples ◽

New Variety ◽

Dry Extract ◽

Annual Herb ◽

Anti Inflammatory ◽

Ferulic Acids ◽

Dose Dependent ◽

Inflammatory Effect

Moldavian Dragonhead (Dracocephalum moldavica L.) is an annual herb. In FGBNU VILAR a new variety of Moldavian Dragonhead «Nezhnost» has been developed. From the herb of the Moldavian Dragonhead, a technology has been developed for obtaining a dry purified extract, which has received the code name «Rozmatin». By NMR (1H and 13C) and HPLC-DAD-MS using standard samples and literature data, the qualitative and quantitative composition of the dry extract "Rozmatin" from the herb of the Dracocephalum moldavica was established. Rosmarinic, caffeic and ferulic acids, rosmarinic acid 3-O-glucoside, luteolin-7-O-β-D-glucuronide, acacetin-7-O-β-D-glucopyranoside (tilianin), apigenin-7-O-β-D-glucoside (Cosmosiin), apigenin-7-O-β-D-glucuronide, chrysoeryol-7-O-β-D-glucuronide, apigenin-7-O-β-D-(6ʺ-O-malonyl) glucoside, acacetin-7-O-β-D-glucuronide, acacetin-7-O-β-D-(6ʺ-malonyl) glucoside, schizotenuin F were identified. It was found that the content of rosmarinic acid in "Rosmatin" is 56.6%, the amount of flavonoids - about 27%. The study of anti-inflammatory and gastroprotective activity of "Rozmatin" in doses of 10 mg/kg, 100 mg/kg was carried out. A dose-dependent anti-inflammatory effect with suppression of the development of the exudative phase of inflammation, as well as a dose-dependent gastroprotective effect of "Rozmatin"", significantly exceeding the similar effect of the referent drug omeprazole, was revealed. Earlier it was found that "Rozmatin" has a tonic effect on the cardiovascular and nervous systems.

Download Full-text

Antimicrobial Effects of Alginate-Based Films Containing Essential Oils on Listeria monocytogenes and Salmonella Typhimurium Present in Bologna and Ham

Journal of Food Protection ◽

10.4315/0362-028x-70.4.901 ◽

2007 ◽

Vol 70 (4) ◽

pp. 901-908 ◽

Cited By ~ 52

Author(s):

MOUNIA OUSSALAH ◽

STÉPHANE CAILLET ◽

STÉPHANE SALMIÉRI ◽

LINDA SAUCIER ◽

MONIQUE LACROIX

Keyword(s):

Listeria Monocytogenes ◽

Essential Oils ◽

Salmonella Typhimurium ◽

Edible Films ◽

Active Compounds ◽

Sensitive Bacterium ◽

Type C ◽

And Migration ◽

Cacl2 Solution ◽

Satureja Montana

Bologna and ham slices (300 of each) were inoculated with Salmonella Typhimurium or Listeria monocytogenes at 103 CFU/cm2. Alginate-based edible films that had been immersed in a 2 or 20% (wt/vol) CaCl2 solution and contained 1% (wt/vol) essential oils of Spanish oregano (O; Corydothymus capitatus), Chinese cinnamon (C; Cinnamomum cassia), or winter savory (S; Satureja montana) were then applied to slices to control pathogen growth. On bologna, C-based films pretreated with 20% CaCl2 were the most effective against the growth of Salmonella Typhimurium and L. monocytogenes. L. monocytogenes was the more sensitive bacterium to O-, C-, and S-based films. L. monocytogenes concentrations were below the detection level (<10 CFU/ml) after 5 days of storage on bologna coated with O-, C-, or S-based films pretreated with 20% CaCl2. On ham, a 1.85 log CFU/cm2 reduction of Salmonella Typhimurium (P ≤ 0.05) was found after 5 days of storage with C-based films regardless of the type of pretreatment used (2 or 20% CaCl2) or when coated with O-based films pretreated with 20% CaCl2. L. monocytogenes was highly resistant in ham, even in the presence of O-, C-, or S-based films. However, C-based films pretreated with 20% CaCl2 were the most effective against the growth of L. monocytogenes. Evaluation of the availability of active compounds in films revealed a significantly higher release of active compounds in C-based films (P ≤ 0.05) regardless of pretreatment or meat tested (bologna or ham). O-based films had the lowest release level of active compounds. The release of active compounds from O- and S-based films pretreated with 20% CaCl2 was faster than that in the same respective films pretreated with 2% CaCl2 regardless of the meat type. C-based film pretreated by immersion in a 20% CaCl2 solution was most efficient against both pathogens, and migration of active compounds was higher in C-based films than in O- and S-based films.

Download Full-text

Rosmarinic Acid and Its Methyl Ester as Antimicrobial Components of the Hydromethanolic Extract ofHyptis atrorubensPoit. (Lamiaceae)

Evidence-based Complementary and Alternative Medicine ◽

10.1155/2013/604536 ◽

2013 ◽

Vol 2013 ◽

pp. 1-11 ◽

Cited By ~ 38

Author(s):

Amin Abedini ◽

Vincent Roumy ◽

Séverine Mahieux ◽

Murielle Biabiany ◽

Annie Standaert-Vitse ◽

...

Keyword(s):

Rosmarinic Acid ◽

Pathogenic Bacteria ◽

Antimicrobial Agents ◽

Synergistic Effects ◽

Isolation And Identification ◽

Traditional Use ◽

Active Compounds ◽

Different Temperatures

Primary biological examination of four extracts of the leaves and stems ofHyptis atrorubensPoit. (Lamiaceae), a plant species used as an antimicrobial agent in Guadeloupe, allowed us to select the hydromethanolic extract of the stems for further studies. It was tested against 46 microorganismsin vitro. It was active against 29 microorganisms. The best antibacterial activity was found against bacteria, mostly Gram-positive ones. Bioautography enabled the isolation and identification of four antibacterial compounds from this plant: rosmarinic acid, methyl rosmarinate, isoquercetin, and hyperoside. The MIC and MBC values of these compounds and their combinations were determined against eight pathogenic bacteria. The best inhibitory and bactericidal activity was found for methyl rosmarinate (0.3 mg/mL). Nevertheless, the bactericidal power of rosmarinic acid was much faster in the time kill study. Synergistic effects were found when combining the active compounds. Finally, the inhibitory effects of the compounds were evaluated on the bacterial growth phases at two different temperatures. Our study demonstrated for the first time antimicrobial activity ofHyptis atrorubenswith identification of the active compounds. It supports its traditional use in French West Indies. Although its active compounds need to be further evaluatedin vivo, this work emphasizes plants as potent sources of new antimicrobial agents when resistance to antibiotics increases dramatically.

Download Full-text

Antifungal Activity of the Extract of a Macroalgae, Gracilariopsis persica, against Four Plant Pathogenic Fungi

Plants ◽

10.3390/plants10091781 ◽

2021 ◽

Vol 10 (9) ◽

pp. 1781

Author(s):

Latifeh Pourakbar ◽

Sina Siavash Moghaddam ◽

Hesham Ali El Enshasy ◽

R. Z. Sayyed

Keyword(s):

Phenolic Compounds ◽

Antifungal Activity ◽

Palmitic Acid ◽

Rosmarinic Acid ◽

Mycelial Growth ◽

Pathogenic Fungi ◽

Hplc Method ◽

Biologically Active ◽

Plant Pathogenic Fungi ◽

Active Compounds

Nowadays, the extract of seaweeds has drawn attention as a rich source of bioactive metabolites. Seaweeds are known for their biologically active compounds whose antibacterial and antifungal activities have been documented. This research aimed to study the profile of phenolic compounds using the HPLC method and determine biologically active compounds using the GC-MS method and the antifungal activity of Gracilariopsis persica against plant pathogenic fungi. G. persica was collected from its natural habitat in Suru of Bandar Abbas, Iran, dried, and extracted by methanol. The quantitative results on phenolic compounds using the HPLC method showed that the most abundant compounds in G. persica were rosmarinic acid (20.9 ± 0.41 mg/kg DW) and quercetin (11.21 ± 0.20 mg/kg DW), and the least abundant was cinnamic acid (1.4 ± 0.10 mg/kg DW). The GC-MS chromatography revealed 50 peaks in the methanolic extract of G. persica, implying 50 compounds. The most abundant components included cholest-5-en-3-ol (3 beta) (27.64%), palmitic acid (17.11%), heptadecane (7.71%), and palmitic acid methyl ester (6.66%). The antifungal activity of different concentrations of the extract was determined in vitro. The results as to the effect of the alga extract at the rates of 200, 400, 600, 800, and 1000 μL on the mycelial growth of four important plant pathogenic fungi, including Botrytis cinerea, Aspergillus niger, Penicillium expansum, and Pyricularia oryzae, revealed that the mycelial growth of all four fungi was lower at higher concentrations of the alga extract. However, the extract concentration of 1000 μL completely inhibited their mycelial growth. The antifungal activity of this alga may be related to the phenolic compounds, e.g., rosmarinic acid and quercetin, as well as compounds such as palmitic acid, oleic acid, and other components identified using the GC-MS method whose antifungal effects have already been confirmed.

Download Full-text

Water Extract of Mentha × villosa: Phenolic Fingerprint and Effect on Ischemia-Reperfusion Injury

Natural Product Communications ◽

10.1177/1934578x1501000636 ◽

2015 ◽

Vol 10 (6) ◽

pp. 1934578X1501000 ◽

Cited By ~ 3

Author(s):

Silvia Fialova ◽

Lucia Veizerova ◽

Viera Nosalova ◽

Katarina Drabikova ◽

Daniela Tekelova ◽

...

Keyword(s):

Liquid Chromatography ◽

Rosmarinic Acid ◽

Ischemia Reperfusion Injury ◽

Tissue Injury ◽

Ex Vivo ◽

Ischemia Reperfusion ◽

Water Extract ◽

Flavonoid Glycosides ◽

Photodiode Array Detection ◽

Dry Extract

Qualitative analysis of the water extract of Mentha x villosa Huds. leaves was performed by liquid chromatography mass spectrometry (LC-MS/MS) and quantitative analysis was made by reverse-phase liquid chromatography coupled with photodiode array detection (LC-DAD). Sixteen phenolic compounds were identified and quantified consisting of 8 phenolic acids/derivatives and 8 flavonoid glycosides (quinic acid, chlorogenic acid, coumaroyl-hexoside, caffeic acid, coumaroylquinic acid, lithospermic acid, rosmarinic acid, salvianolic acid A, luteolin-7- O-glucuronide, luteolin-7- O-glucoside, luteolin-7- O-rutinoside, eriodictyol-7- O-rutinoside, apigenin-7- O-glucuronide, kaempferol-3- O-glucuronide, chrysoeriol-7- O-rutinoside, and hesperetin-7- O-rutinoside). Luteolin-7- O-rutinoside (25.6 ± 0.7 mg/g dry extract) and rosmarinic acid (17.9 ± 0.4 mg/g dry extract) were the most abundant. High antioxidant activity of this phenolic-rich water extract was confirmed in vitro by DPPH and ABTS tests and ex vivo in the ischemia-reperfusion injured rat superior mesenteric artery. Thus, the water extract of M. x villosa leaves seems to be a promising agent in prevention of tissue injury caused by oxidative stress.

Download Full-text