Antioxidant and Antimicrobial Properties of Stachys maritima via Quantum Dots and Molecular Docking.

Stachys maritima is a species of plant belonging to the Lamiaceae, commonly known as common sea lavender. The extraction of S. maritima involves drying the aerial parts, grinding them into powder, followed by extraction with methanol. ST-CQDs (S. maritima carbon quantum dots) were synthesized from S. maritima extract via pyrolysis. An optimal synthesis condition of 7 hours of pyrolysis was determined to yield ST-CQDs with high absorption in the visible-UV range. Characterization techniques such as UV-visible spectroscopy and TEM (Transmission Electron Microscopy) confirmed the spherical and homogeneous nature of the carbon quantum dots. S. maritima methanol extract exhibited strong antioxidant activity with a DPPH (2,2-Diphenyl-1-picrylhydrazyl) IC50 value of 0.114±0.001 mg/mL. Similarly, ST-CQDs showed strong antioxidant properties with a DPPH IC50 value of 0.69±0.03 mg/mL. Moreover, the methanol extract of S. maritima demonstrated antimicrobial activity against E. coli ATCC 25922 and S. aureus ATCC 25923, with effective MIC values of 25 mg/mL and 6.25 mg/mL, respectively. However, ST-CQDs did not show antimicrobial effects against the tested microorganisms (E. coli ATCC 25922, S. aureus ATCC 25923, K. pneumoniae ATCC 13883, and C. albicans ATCC 10231). Molecular docking simulations suggested that compounds derived from S. maritima (such as 9,12,15-octadecatrienoic acid and palmitic acid) could interact effectively with TNF-α (Tumor Necrosis Factor Alpha), indicating potential anti-inflammatory properties. This study highlights that the methanol extract of S. maritima possesses potent antioxidant and antimicrobial activities, and ST-CQDs exhibit similar antioxidant properties. However, ST-CQDs did not demonstrate antimicrobial activity against the tested pathogens. Molecular docking simulations also suggest potential anti-inflammatory properties of compounds derived from the plant.

Uncovering chemical profiles, biological potentials, and protection effect against ECM destruction in H2 O2 -treated HDF cells of the extracts of Stachys tundjeliensis.

The genus Stachys L., one of the largest genera of the Lamiaceae family, is highly represented in Turkey. This study was conducted to determine the bio-pharmaceutical potential and phenolic contents of six different extracts from aerial parts of Stachys tundjeliensis. The obtained results showed that the ethanol extract exhibited the highest antioxidant activity in the antioxidant assays. Meanwhile, the ethanol extract displayed strong inhibitory activity against α-tyrosinase, the dichloromethane extract exhibited potent inhibition against butyrylcholinesterase, and the n-hexane extract against α-amylase. Based on ultra-high performance liquid chromatography coupled to high-resolution mass spectrometry analysis, more than 90 secondary metabolites, including hydroxybenzoic acid, hydroxycinnamic acid, and their glycosides, acylquinic acids, phenylethanoid glycosides, and various flavonoids were identified or tentatively annotated in the studied S. tundjeliensis extracts. It was observed that the application of S. tundjeliensis eliminated H2 O2 -induced oxidative stress. It was determined that protein levels of phospho-nuclear factor kappa B (NF-κB), receptor for advanced glycation endproducts, and activator protein-1, which are activated in the nucleus, decreased, and the synthesis of matrix metalloproteinase (MMP)-2 and MMP-9 also decreased to basal levels. Overall, these findings suggest that S. tundjeliensis contains diverse bioactive compounds for the development of nutraceuticals or functional foods with potent biological properties.

Isolation and Purification of Harpagogenin as an Nrf2-ARE Activator from the Tubers of Chinese Artichoke (Stachys sieboldii).

Chinese artichoke tuber (Stachys sieboldii Miq.) is used as an herbal medicine as well as edible food. This study examined the effect of the Chinese artichoke extracts on the nuclear factor erythroid 2-related factor 2 (Nrf2)-antioxidant response element (ARE) pathway that induces the expression of antioxidant enzymes to explore its novel characteristics. Hot water extracts exhibited relatively high ARE activity. ARE activity was observed in two fractions when the hot water extracts were separated in the presence of trifluoroacetic acid using HPLC. Conversely, the highly active fraction disappeared when the hot water extracts were separated in the absence of trifluoroacetic acid. These results indicate that acidic degradation produces active ingredients. The structural analysis of the two active fractions identified harpagide, which is an iridoid glucoside, and harpagogenin. In vitro experiments revealed that harpagide was converted into harpagogenin under acidic conditions and that harpagogenin, but not harpagide, had potent ARE activity. Therefore, this study identified harpagogenin, which is an acid hydrolysate of harpagide, as an ARE activator and suggests that Nrf2-ARE pathway activation by Chinese artichoke contributes to the antioxidative effect.

Untargeted metabolomics study and identification of potential biomarkers in the six sections of the genus Stachys L. (Lamiaceae) using HPLC-MQ-API-MS/MS.

INTRODUCTION: The genus Stachys L., belonging to the family Lamiaceae, is one of the largest genera with remarkable medicinal properties. Plants of this genus produce a broad range of secondary metabolites. OBJECTIVES: Due to the incomplete comprehensive assessment of chemical profiles in Stachys species, we conducted an untargeted metabolomics study and identified potential biomarkers in the six sections of Stachys with chemotaxonomic importance. MATERIAL AND METHODS: Dried leaves of 17 taxa were utilized for analysis of all the constituents using HPLC-MQ-API-MS. The obtained data were processed and analyzed using multivariate statistical methods, including heatmaps, PLS-DA score plots, functional analysis of metabolic pathways, metabolite set enrichment analysis, and biomarker and network analysis. RESULTS: Among the 129 metabolites, 111 flavonoids and 18 non-flavonoids were recognized. The most represented flavonoids, including 41 flavones and 20 flavonols, displayed remarkable abundance. In non-flavonoid compounds, a total of six coumarins and six phenolic acids were present at high levels. In terms of approved markers in six sections, 76 chemical compounds, mainly flavonoids, coumarins, quinic acids, and cinnamic acids, were identified as potential biomarkers or chemotaxonomic indicators. Accordingly, the taxonomic complexities of some Stachys species in sections Fragilicaulis, Aucheriana, and Setifolia were properly resolved. CONCLUSION: An HPLC-MS/MS-based metabolomics approach integrated with multivariate statistical methods was employed to identify (1) valuable markers and analyze metabolic diversity and (2) predict the pharmaceutical properties of Stachys species. The obtained chemical profiles provide a new perspective for investigation of the Stachys genus.

Isolation of bioactive components with soluble epoxide hydrolase inhibitory activity from Stachys sieboldii MiQ. by ultrasonic-assisted extraction optimized using response surface methodology.

Stachys sieboldii MiQ (SSM) is an important food and medicinal herb in Korea, used to improve memory of patients with senile dementia and cardiovascular diseases. However, little information on bioactive components from SSM or standardized extraction methods for these components is available. This study isolated and purified major components from SSM for the first time, and assessed their ability to inhibit soluble epoxide hydrolase (sEH). The results showed that acteoside is the most potent inhibitor of sEH, with an IC50 of 33.5 ± 0.5 µM. Additional active components, including harpagide, tryptophan, and 8-acetate-harpagide, along with acteoside, were tentatively identified using high-performance liquid chromatography photodiode array tandem mass spectrometry (HPLC-PDA-MS/MS) and quantified using an ultraviolet detector at 210 nm. Further, an ultrasonic-assisted extraction technique for extraction of four bioactive compounds in SSM was developed and optimized using response surface methodology (RSM). The optimal extraction conditions were: extraction time, 30.46 minutes; extraction temperature, 67.95 °C, and methanol concentration 53.85%. The prediction model of RSM was validated with laboratory experiments. The similarity between predicted and actual values was 97.84%. The extraction method is thus a rapid, environment-friendly, energy-saving method can be applied to extract bioactive components from SSM in large quantities.

New Rare Ent-Clerodane Diterpene Peroxides from Egyptian Mountain Tea (Qourtom) and Its Chemosystem as Herbal Remedies and Phytonutrients Agents.

Genus Stachys, the largest genera of the family Lamiaceae, and its species are frequently used as herbal teas due to their essential oils. Tubers of some Stachys species are also consumed as important nutrients for humans and animals due to their carbohydrate contents. Three new neo-clerodane diterpene peroxides, named stachaegyptin F-H (1, 2, and 4), together with two known compounds, stachysperoxide (3) and stachaegyptin A (5), were isolated from Stachys aegyptiaca aerial parts. Their structures were determined using a combination of spectroscopic techniques, including HR-FAB-MS and extensive 1D and 2D NMR (1H, 13C NMR, DEPT, 1H-1H COSY, HMQC, HMBC and NOESY) analyses. Additionally, a biosynthetic pathway for the isolated compounds (1-5) was discussed. The chemotaxonomic significance of the isolated diterpenoids of S. aegyptiaca in comparison to the previous reported ones from other Stachys species was also studied.

Ultrasound combined with manganese-oxide nanoparticles loaded on activated carbon for extraction and pre-concentration of thymol and carvacrol in methanolic extracts of Thymus daenensis, Salvia officinalis, Stachys pilifera, Satureja khuzistanica, and mentha, and water samples.

A dispersive micro solid-phase extraction (DMSPE) technique was developed using manganese-oxide nanoparticles loaded on activated carbon (Mn3O4-NPs-AC) as an effective sorbent combined with ultrasound for the extraction and determination of a trace amount of thymol and carvacrol in methanolic extracts of Thymus daenensis, Salvia officinalis, Stachys pilifera, Satureja khuzistanica and mentha, and water samples. Thymol and carvacrol phenolic compounds were extracted from real samples using acetonitrile (ACN) as the desorption solvent. Using central composite design (CCD), the effects of pH, ionic strength (NaCl), nano-sorbent mass, contact time, and desorption volume were investigated. Additionally, based on five-level variables, response surface methodology was used to determine the individual and interactive effects between factors on the process. The optimized extraction conditions included 12 mg of Mn3O4-NPs-AC as the sorbent, 300 µL of ACN as the desorption solvent, pH 3.0, 0.5 w/v% of NaCl, and 4.5 min sonication time. Under the optimized conditions, for all the samples, the limits of detection were 0.054-0.104 ng mL-1 and the limits of quantification were 0.178-0.345 ng mL-1. The correlation coefficients of the calibration curves were >0.985, i.e. in the range of 0.4-6000 ng mL-1. To validate the effects of the matrix, the recovery, reproducibility, repeatability, and overall uncertainty were calculated for the five methanolic extracts, at 50, 100, and 500 ng mL-1. The recovery ranged between 94.5% and 109.0% with a relative standard deviation of <8.0% for the repeatability and reproducibility precision, which strongly supports the favorable repeatability and reproducibility of the method. The presented method also has the excellent sorbent features of NPs for the sorption of the analyte, which is due to the use of ultrasound for dispersion of the material in the sample matrix.

Antiangiogenic Iridoids from Stachys ocymastrum and Premna resinosa.

In this paper, the isolation of one new iridoid glucoside, 6ß-acetoxyipolamiide (1: ), and thirteen (2:  - 14: ) known congeners from two Lamiaceae species, Stachys ocymastrum and Premna resinosa, leaf extracts is reported. The structural determination of the isolated compounds was performed by mono- and bidimensional NMR spectroscopic analysis as well as MS experiments. The isolates were assayed for their antiangiogenic activity by two in vivo models, zebrafish embryos and chick chorioallantoic membrane assays. The compounds with a significant antiangiogenic activity in both assays were ß-hydroxyipolamiide (2: ), ipolamiide (3: ), and buddlejoside A5 (8: ). 6-O-α-l-(3″-O-p-Methoxycinnamoyl-4″-O-acetyl)rhamnopyranosyl catalpol (13: ) and 6-O-α-l-(2″-trans-caffeoyl)rhamnopyranosyl catalpol (6: ) showed the best antiangiogenic response on blood vessel growth in zebrafish embryos, whereas saccatoside (10: ) and 6-O-α-l-(2″-O - : p-methoxycinnamoyl-3″-O-acetyl)rhamnopyranosyl catalpol (14: ) resulted in a strong reduction of capillary formation in the chorioallantoic membrane assay.

Fingerprinting, Antimicrobial, Antioxidant, Anticancer, Cyclooxygenase and Metabolic Enzymes Inhibitory Characteristic Evaluations of Stachys viticina Boiss. Essential Oil.

The present study aimed to identify the chemical constituents and to assess the in-vitro, antimicrobial, anticancer, antioxidant, metabolic enzymes and cyclooxygenase (COX) inhibitory properties of essential oil (EO) of Stachys viticina Boiss. leaves. The S. viticina EO was isolated and identified using microwave-ultrasonic and GC-MS techniques, respectively. Fifty-two compounds were identified, of which endo-borneol was the major component, followed by eucalyptol and epizonarene. The EO was evaluated against a panel of in-vitro bioassays. The EO displayed antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli and Epidermophyton floccosum, with MIC values of 0.039, 0.078 and 0.78 mg/mL, respectively. The EO exhibited cytotoxicity against HeLa (cervical adenocarcinoma) and Colo-205 (colon) cancer cell lines with percentages of inhibition of 95% and 90%, for EO concentrations of 1.25 and 0.5 mg/mL, respectively. Furthermore, it showed metabolic enzyme (α-amylase, α-glucosidase, and lipase) inhibitory (IC50 = 45.22 ± 1.1, 63.09 ± 0.26, 501.18 ± 0.38 µg/mL, respectively) and antioxidant activity, with an IC50 value of 19.95 ± 2.08 µg/mL. Moreover, the S. viticina EO showed high cyclooxygenase inhibitory activity against COX-1 and COX-2 with IC50 values of 0.25 and 0.5 µg/mL, respectively, similar to those of the positive control (the NSAID etodolac). Outcomes amassed from this investigation illustrate that S. viticina EO represents a rich source of pharmacologically active molecules which can be further validated and explored clinically for its therapeutic potential and for the development and design of new natural therapeutic preparations.

Chemical composition, cytotoxic effect and antimicrobial activity of Stachys koelzii Rech.f. essential oil against periodontal pathogen Prevotella intermedia.

Prevotella intermedia is associated with periodontal diseases and endodontic infections. Periodontitis can be suppressed by utilizing the antiseptics, which target the infectious bacteria. The member of Stachys sp. has been used traditionally in the form of decoction or infusion for management of infectious diseases. The subject of this article was to evaluate the chemical composition, antimicrobial and cytotoxic effect of Stachys koelzii essential oil and its main components against Prevotella intermedia. GC-FID and GC-MS analysis were used to determine the chemical composition. The antimicrobial effects of S. koelzii essential oil was evaluated by micro-broth dilution assay. Time kill curve assays, leakage of cytoplasmic materials and anti-biofilm effects were determined. Its cytotoxic effect was evaluated by MTT assay. Essential oil with main components of α-pinene, trans-caryophyllene and 1,8-cineole inhibited P. intermedia with MIC and MBC values of 0.1 and 0.2 mg/mL. Its biofilm formation was higher than α-pinene, followed by trans-caryophyllene and 1,8-cineole. Essential oil and its main components increased the leakage of cytoplasmic components. Essential oil showed cytotoxic effect on HeLa cell lines with IC50 0.06 mg/mL. The cytotoxic effect of α-pinene on healthy cell lines was higher than essential oil. S. koelzii essential oil can be used in mouthwash formulations and its efficacy should be evaluated in large clinical studies.

Nutritional Evaluation of Non-Conventional Vegetables in Brazil.

The objective of this study was to characterize the nutritional compounds of interest present in vegetables known as non-conventional, in Brazil. The following evaluations were carried out: antioxidant activity, phenolic compounds, vitamin C, calories, carbohydrates, humidity, lipids, proteins, fiber, acidity and quantification of minerals (P, K, Ca, Mg, S, Cu, Fe, Mn, Zn and B). The species studied were Amaranthus hybridus L., Amaranthus viridis L., Basella alba L., Eryngium campestre L., Hibiscus sabdariffa L., Lactuca canadensis L., Rumex acetosa L., Stachys byzantina K. Koch, Tropaeolum majus L. and Xanthosoma sagittifolium L. Representative samples of plant structures of interest were harvested from each species suitable for human consumption such as leaves, flowers and flower buds. The results were submitted to multivariate analysis - principal components analysis (PCA). All the species present nutritional compounds of interest in different levels among the evaluated structures.

Identification of Insecticidal Constituents from the Essential Oil from the Aerial Parts Stachys riederi var. japonica.

The essential oil of Stachys riederi var. japonica (Family: Lamiaceae) was extracted by hydrodistillation and determined by GC and GC-MS. A total of 40 components were identified, representing 96.01% of the total oil composition. The major compounds in the essential oil were acetanisole (15.43%), anisole (9.43%), 1,8-cineole (8.07%), geraniol (7.89%), eugenol (4.54%), caryophyllene oxide (4.47%), caryophyllene (4.21%) and linalool (4.07%). Five active constituents (acetanisole, anisole, 1,8-cineole, eugenol and geraniol) were identified by bioactivity-directed fractionation. The essential oil possessed fumigant toxicity against maize weevils (Sitophilus zeamais) and booklice (Liposcelis bostrychophila), with LC50 values of 15.0 mg/L and 0.7 mg/L, respectively. Eugenol and anisole exhibited stronger fumigant toxicity than the oil against booklice. 1,8-Cineole showed stronger toxicity, and anisole as well as eugenol exhibited the same level of fumigant toxicity as the essential oil against maize weevils. The essential oil also exhibited contact toxicity against S. zeamais adults and L. bostrychophila, with LC50 values of 21.8 µg/adult and 287.0 µg/cm², respectively. The results indicated that the essential oil of S. riederi var. japonica and its isolates show potential as fumigants, and for their contact toxicity against grain storage insects.

Polar Constituents, Essential Oil and Antioxidant Activity of Marsh Woundwort (Stachys palustris L.).

Stachys palustris, well-known as marsh woundwort, is a perennial herb growing in wet environments of Europe. Its tubers, leaves and seeds are eaten raw or cooked. Alike other Stachys species, the plant is also used as a traditional remedy. Despite S. palustris has been consumed for centuries, little is known about its chemical constituents. In this work the main secondary metabolites of S. palustris from Hungary and France have been analysed. From the plant ethanolic extracts, ethanoid glucosides, isoscutellarein derivatives, caffeoyl-quinic acids and iridoids have been isolated and structurally characterized by NMR. The essential oils were analysed by GC/MS and showed (E)-phytol, fatty acids and carbonylic compounds as the most abundant compounds. The radical scavenging capacity of plant ethanolic extracts, as evaluated by the DPPH assay, was noteworthy, with IC50 values of 92.08 - 105.42 µg/ml.

Antioxidant, anticholinesterase and antibacterial activities of Stachys guyoniana and Mentha aquatica.

CONTEXT: Stachys guyoniana Noë ex. Batt. and Mentha aquatica L. are two Algerian Lamiaceae used in folk medicine. OBJECTIVE: To investigate their antioxidant, anticholinesterase and antibacterial activities. MATERIAL AND METHODS: n-Butanol (BESG), ethyl acetate (EESG) and chloroform (CESG) extracts of S. guyoniana and methanol (MEMA) and chloroform (CEMA) aerial part extracts of M. aquatica and methanol (MERMA) and acetone (AERMA) roots extracts of M. aquatica were evaluated for their antioxidant activity by the ß-carotene-linoleic acid, DPPH• and ABTS•+ scavenging, CUPRAC and metal chelating assays. The anticholinesterase activity was tested against AChE and BChE. The antibacterial activity was assessed by MICs determination against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella heidelberg, Klebsiella pneumoniae, Enterobacter aerogenes and Morganella morganii strains. RESULTS: In the ß-carotene test, the CESG (IC50: 2.3 ± 1.27 µg/mL) exhibited the highest activity. The BESG was the best scavenger of DPPH• (IC50: 2.91 ± 0.14 µg/mL). In the ABTS test, AERMA was the most active (IC50: 4.21 ± 0.28 µg/mL). However, with the CUPRAC, the BESG exhibited the best activity (A0.50: 0.15 ± 0.05 µg/mL) and was active in metal chelating assay with 48% inhibition at 100 µg/mL. The BESG was the best AChE inhibitor (IC50: 5.78 ± 0.01 µg/mL) however, the AERMA showed the highest BChE inhibitory activity (IC50: 19.23 ± 1.42 µg/mL). The tested extracts exhibited a good antibacterial activity. CONCLUSION: This study demonstrated good antioxidant, anticholinesterase and antibacterial potential of S. guyoniana and M. aquatica, which fits in well with their use in folk medicine.

Hepatoprotective effect of Stachys pilifera ethanol extract in carbon tetrachloride-induce hepatotoxicity in rats.

CONTEXT: Stachys pilifera Benth (Lamiaceae) has long been used to treat infectious diseases, respiratory and rheumatoid disorders in Iranian folk medicine. Antitumor and antioxidant activity of the plant have been reported. OBJECTIVE: The study was designed to assess the hepatoprotective activity of ethanol extract of Stachys pilifera in carbon tetrachloride (CCl4)-induced hepatotoxicity in rats. MATERIALS AND METHODS: The rats were randomly divided into six equal groups (n = 7). Group I was treated with normal saline; Group II received CCl4 (1 mL/kg. i.p., twice a week) for 60 consecutive days; Groups III, IV and V were given CCl4 plus Stachys pilifera (100, 200 and 400 mg/kg/d,p.o.); Group VI received the extract (400 mg/kg/d, p.o.). Histopathological analysis and measurement of serum aspartate aminotransferase (AST), alanine aminotransferase (ALT), alkaline phosphatase (ALP), malondialdehyde (MDA), total protein (TP) and albumin (ALB) were performed. RESULTS: CCl4 caused a significant increase in the serum levels of AST, ALT, ALP and MDA as well as decreased ALB, and TP serum levels (p < 0.001). The extract (200 and 400 mg/kg/d) significantly normalized the CCl4-elevated levels of ALT, AST, ALP and MDA (p < 0.001). The extract (200 and 400 mg/kg/d) also increased the serum levels of TP compared to CCl4 group (p< 0.01). The extract (200 and 400 mg/kg/d) also decreased the histological injuries (inflammation and fatty degeneration) by CCl4. DISCUSSION: The results revealed that the Stachys pilifera extract could provide considerable protection against CCl4 hepatotoxicity in rats that may be related to its antioxidant properties.

Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: in silico, in vitro, and in vivo studies.

Fractionation of the bioactive dichloromethane extract from the aerial parts of Stachys glutinosa led to the isolation of four flavones, xanthomicrol (1), sideritoflavone (2), 8-methoxycirsilineol (3), and eupatilin (4), along with two neo-clerodane diterpenes, roseostachenone (8) and a new compound, 3α,4α-epoxyroseostachenol (7). In order to study structure-activity relationships, two methoxyflavones [5-demethyltangeretin (5) and tangeretin (6)] were synthesized by the methoxylation of xanthomicrol. The isolated compounds (1-4, 7, and 8) as well as the xanthomicrol semisynthetic derivatives (5 and 6) were evaluated for their binding affinity to the µ and δ opioid receptors. Xanthomicrol was the most potent binder to both µ and δ receptors, with a Ki value of 0.83 and 3.6 µM, respectively. Xanthomicrol administered intraperitoneally in mice at a dose of 80 mg/kg significantly reduced morphine-induced antinociception in the tail flick test. Our results suggested that xanthomicrol is a µ opioid receptor antagonist. Docking experiments were carried out to acquire a deeper understanding about important structural aspects of binding of xanthomicrol. In summary, these data suggest that xanthomicrol is a valuable structure for further development into a potential µ opioid receptor antagonist.

Phytochemical Analysis, Biological Activity, and Secretory Structures of Stachys annua (L.) L. subsp. annua (Lamiaceae) from Central Italy.

Stachys annua subsp. annua, well-known in central Italy as 'stregona annuale', is an annual, small, slightly-scented herb, commonly found in fields and uncultivated areas in almost all regions of Italy. In folk medicine, its aerial parts were used as anti-catarrhal, febrifuge, tonic, and vulnerary. In the present work, the chemical composition of the flowering aerial parts was studied. The hydrodistilled volatile oil, analysed by GC/MS, showed sesquiterpenoids as the major fraction (42.5%); phytol (9.8%), germacrene D (9.2%), and spathulenol (8.5%) were the most abundant constituents. The volatile oil was assayed for antioxidant and cytotoxic activity by DPPH, ABTS, FRAP, and MTT methods. The cytotoxicity results against HCT116, A375, and MDA-MB 231 human tumor cell lines were significant, with IC50 values of 23.5, 37.2, and 41.5 µg/ml, respectively, whereas the antioxidant power was negligible. The EtOH extract was composed mainly of three glycosidic flavonoids, namely 7-{[2-O-(6-O-acetyl-ß-D-allopyranosyl)-ß-D-glucopyranosyl]oxy}-5,8-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one (1), 7-{[6-O-acetyl-2-O-(6-O-acetyl-ß-D-allopyranosyl)-ß-D-glucopyranosyl]oxy}-2-(3,4-dihydroxyphenyl)-5,8-dihydroxy-4H-1-benzopyran-4-one (2), and 7-{[6-O-acetyl-2-O-(ß-D-allopyranosyl)-ß-D-glucopyranosyl]oxy}-2-(3-hydroxy-4-methoxyphenyl)-5,8-dihydroxy-4H-1-benzopyran-4-one (3). On the contrary, iridoids, considered chemotaxonomic markers of the genus Stachys, were absent in this species. Finally, the morphological and histochemical survey showed that glandular trichomes were composed of two main types, i.e. peltate type A and capitate types B and C giving positive response for both lipids and polyphenols.

Cytotoxic, antioxidant and antimicrobial effects of nine species of woundwort (Stachys) plants.

CONTEXT: Woundwort (Stachys) plants from the Lamiaceae family have been used in folk medicine for various purposes. OBJECTIVE: This study was designed to analyze cytotoxic, antioxidant and antimicrobial activities of Stachys plants, because these fields have extensively benefited of drug discovery from natural sources. MATERIALS AND METHODS: Nine Stachys plants were collected from different regions of Iran. Cytotoxic activities of methanol, 80% methanol and dichloromethane (DCM) extracts of these plants were assessed on three human cancer cell lines (HL-60, K562 and MCF-7 cells) with the MTT assay, while antioxidant and antimicrobial activities were determined on methanol extracts by DPPH and nutrient broth micro-dilution assays, respectively. RESULTS: DCM extract of St. pilifera Benth. had the lowest IC50 in three cancer cell lines ranging from 33.1 to 48.2 µg/ml, followed by the 80% methanol extract of St. persica S.G.Gmel. ex C.A.Mey. (IC50 range: 62.1-104.1 µg/ml) and DCM extract of St. byzantina C. Koch (IC50 range: 62.7-131.0 µg/ml). St. byzantina. St. lavandulifolia Vahl., St. acerosa Boiss., St. obtusicrena Boiss. and St. persica showed lowest IC50 values in the DPPH scavenging assay (135.1, 162.6, 164.7, 169.4 and 172.4 µg/ml, respectively), while their total phenolic contents were 23.9, 18.2, 18.6, 20.4, 27.8 mg equivalent of gallic acid in 1 g dry plant, respectively. The methanol extracts of St. byzantina and St. persica inhibited all six tested Gram-negative and Gram-positive bacterial strains. CONCLUSION: Various Stachys species (especially St. byzantina and St. persica) are valuable sources of natural compounds with important biological properties.

Carthamus, Salvia and Stachys species protect neuronal cells against oxidative stress-induced apoptosis.

CONTEXT: Finding effective therapies for neurodegenerative diseases is of utmost importance for the aging population. Plants growing in Iran are rich sources of antioxidants and active phytochemicals. OBJECTIVE: The protective capacity of plants, with a special focus on those with reported antioxidant or neuroprotective potential or nervous system-related applications in folk medicine, was tested against oxidative stress-induced apoptosis. MATERIALS AND METHODS: Aerial parts of 20 plants including Carthamus, Salvia, and Stachys species were extracted with 80% methanol and dichloromethane and preincubated with neuronal PC12 cells for 3 h. Oxidative stress and apoptosis were induced by hydrogen peroxide (75 µM, 1 h exposure). Cell viability and intracellular reactive oxygen species (ROS) were measured by MTT and 2',7'-dichlorofluorescein-diacetate (DCFH-DA) assays, respectively, while apoptosis was determined by annexin V-FITC/propidium iodide staining by a flow cytometer. RESULTS: Eighty percent methanol extracts of Carthamus oxyacantha Bieb. (Asteraceae), Salvia santolinifolia Boiss. (Lamiaceae), and Salvia sclarea L. (Lamiaceae) at the concentration of 100 µg/ml showed significant neuroprotection in the MTT assay by 38.7, 34.7, and 39.5%, respectively, and inhibited intracellular ROS by 48.6, 61.9, and 61.4%, respectively. The first two extracts also significantly inhibited apoptosis. Dichloromethane extracts of C. oxyacantha and Stachys pilifera Benth. (Lamiaceae) at the concentration of 25 µg/ml showed neuroprotection by 27.5 and 26.5%, respectively, and inhibited ROS by 44.5 and 39.4%, respectively. CONCLUSION: The above-mentioned plants seem to have important biological activities and their further study may lead to the discovery of new natural therapeutics useful against disorders such as Alzheimer and Parkinson diseases.

Two new glycosides from Stachys geobombycis C.Y.Wu.

Two new compounds geobomlin A (1) and geobomlin B (2) were isolated from the roots of Stachys geobombycis C. Y. Wu. Structural determinations were established principally by two-dimensional NMR and MS data analyses. Geobomlin B showed moderate inhibitory activity against α-glucosidase with IC50 = 248.77 µM. We have also determined the mechanism by which geobomlin B elicit its inhibitory effect on α-glucosidase, for which we have established a competitive inhibition mode. Docking studies confirmed our results on geobomlin B α-glucosidase inhibitory properties.