Phytochemical screening and evaluation of the antimicrobial and antioxidant activities of Ferula caspica M. Bieb. extracts.

Chloroform, ethyl acetate and methanol extracts from the aerial parts of Ferula caspica M. Bieb. were tested for their antioxidant capacities by CUPRAC, ABTS, FRAP, Folin-Ciocalteu and aluminum chloride methods and for antimicrobial activities by the broth microdilution method. Chloroform and ethyl acetate extracts showed the highest antioxidant capacity and antimicrobial activity. Three known sesquiterpene derivatives; 1-(2',4'-dihydroxyphenyl)-3,7,11-trimethyl-3-vinyl-6(E),10-dodecadien-1-one (1), 2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4',8'-dimethyl-3',7'-nonadienyl]-furo[3,2,c]coumarin (2), 2,3-dihydro-7-hydroxy-2,3-dimethyl-3-[4',8'-dimethyl-3',7'-nonadienyl]-furo[3,2,c]coumarin(3); phenylpropanoid; laserine/2-epilaserine (4/5) and steroid mixtures; stigmasterol and ß-sitosterol (6/7) were isolated from chloroform extract; three known flavonoids; kaempferol-3-O-ß-glucopyranoside (8), kaempferol-3-O-α-rhamnopyranoside (9), quercetin-3-O-ß-glucopyranoside (10), and one benzoic acid derivative; 2,4-dihydroxybenzoic acid (11) were isolated from the ethyl acetate extract. The structures were elucidated by spectroscopic methods.

The evaluation of sterile solutions of Ilwensisaponin A and C from Verbascum pterocalycinum var. mutense Hub.-Mor. on antiviral, antinociceptive and anti-inflammatory activities.

Antiviral, antinociceptive and anti-inflammatory activities of the 1% sterile solutions of Ilwensisaponin A and C isolated from the methanolic extract of the flowers of Verbascum pterocalycinum var. mutense Hub.-Mor. were investigated. Antiviral activities of sterile solutions were evaluated against Bovine Herpes Virus Type-1 (BHV-1) (Cooper strain). Both solutions showed cytotoxic effects. However, none of the sterile solutions showed antiviral activity with CPE values. Anti-inflammatory and antinociceptive response were obtained at doses of 100 mg/kg. The results of the evaluation of the anti-inflammatory activities induced by carrageenan showed that these sterile solutions possess active constituents and diminish cyclooxygenase activitiy. In addition, antinociceptive activities using p-benzoquinone-induced writhing model in mice of tested solutions were found to show notable activity in statistical analysis without inducing any apparent acute toxicity as well as gastric damage. To the best of our knowledge, this study is the first investigation of antiviral, anti-inflammatory and antinociceptive activities of sterile solutions of Ilwensisaponin A and C isolated from Verbascum pterocalycinum var. mutense Hub.-Mor. growing in Turkey.

Structure Elucidation and Antimicrobial Activities of Secondary Metabolites from the Flowery Parts of Verbascum mucronatum Lam.

OBJECTIVES: To determine the secondary metabolites from Verbascum mucronatum Lam. and evaluate their antimicrobial activity. MATERIALS AND METHODS: Antimicrobial activities of the isolated metabolites were determined using broth microdilutions against the bacteria (Escherichia coli ATCC 25922, Enterococcus faecalis ATCC 29212, Pseudomonas aeruginosa ATCC 27853, Staphylococcus aureus ATCC 29213) and fungi (Candida albicans ATCC 90028, Candida krusei ATCC 6258, Candida parapsilosis ATCC 90018). RESULTS: Four iridoid glycosides; ajugol (1), aucubin (2), lasianthoside I (3), catalpol (4), two triterpenic saponins; ilwensisaponin C (5), ilwensisaponin A (=mimengoside A) (6), and one phenylethanoid glycoside; verbascoside (=acteoside) (7) were isolated from the water soluble parts of the methanolic extract gained flowery parts of V. mucronatum Lam. CONCLUSION: Within the obtained compounds, ajugol and ilwensisaponin A showed moderate antimicrobial activity, especially against fungi.

Inhibitory effect of the methanolic extract of Verbascum latisepalum Hub.-Mor. on endothelium-dependent relaxation in rat thoracic aorta.

The leaves and flowers of Verbascum species are used to treat respiratory disorders, haemorrhoids, rheumatic pain, and wounds as well as for the treatment of eczema and other types of inflammatory skin conditions in traditional Turkish medicine. We examined the effect of the methanolic extract of the aerial parts of Verbascum latisepalum Hub.-Mor. on the endothelium-dependent relaxation response in rat aortic rings which is mediated by nitric oxide (NO). Six fractions, A-F, were obtained from the methanolic extract through bioassay-guided fractionation procedures. The phenylethanoid glycoside verbascoside was isolated from fraction D and its structure elucidated by spectral techniques. The inhibitory effects of the extract, its fractions, and verbascoside on the acetylcholine-induced relaxation response in phenylephrine-precontracted aorta was examined in the absence and presence of L-arginine, a precursor in the synthesis of NO. The observation that the effects of the methanolic extract, of fraction D, and of verbascoside were reversed by L-arginine, indicates that verbascoside has an inhibitory effect on the synthesis of NO. This effect should be taken into consideration in view of the wide range of uses of Verbascum species in Turkish folk medicine.

The in vivo anthelmintic efficacy of some Verbascum species growing in Turkey.

Verbascum L. (Scrophulariaceae) species are used for desiccating wounds and as a fish poison in Anatolia as well as for diarrhea and dysentery of animals in several countries. To further evaluate their activity, methanolic extracts obtained from 13 Verbascum species growing in Turkey, including V. chionophyllum Hub.-Mor., V. cilicicum Boiss., V. dudleyanum (Hub.-Mor.) Hub.-Mor., V. lasianthum Boiss., V. latisepalum Hub.-Mor., V. mucronatum Lam., V. olympicum Boiss., V. pterocalycinum var. mutense Hub.-Mor., V. pycnostachyum Boiss. & Heldr., V. salviifolium Boiss., V. splendidum Boiss., V. stachydifolium Boiss. & Heldr. and V. uschackense (Murb.) Hub.-Mor. were evaluated for their in vivo anthelmintic activity. The extracts from V. lasianthum, V. latisepalum, V. mucronatum and V. salviifolum showed the highest inhibitory rates against Aspiculuris tetraptera at 100mg/kg in mice. Additionally, extracts from V. dudleyanum and V. pterocalycinum var. mutense were found generally highly effective. The remaining species did not show any activity. Results of the present study support the utilization of these plant species employed in Turkish folk medicine.

Bioassay-guided isolation of anti-inflammatory, antinociceptive and wound healer glycosides from the flowers of Verbascum mucronatum Lam.

ETHNOPHARMACOLOGICAL RELEVANCE: The leaves, flowers and whole aerial parts of Verbascum L. species have been used to treat respiratory problems, haemorrhoids and other types of inflammatory conditions in traditional Turkish medicine. AIM OF THE STUDY: In order to evaluate this traditional information, the anti-inflammatory, antinociceptive and wound healing activities of Verbascum mucronatum Lam. which is used as haemostatic in Turkish folk medicine were investigated. MATERIALS AND METHODS: In vivo inhibitory effect of the extracts on the carrageenan-induced hind paw edema model in mice was studied for the assessment of anti-inflammatory activity. Moreover, the wound healing potential of the plant were evaluated by using in vivo wound healing experimental models, i.e. incision and excision models on mice and rats, were comparatively assessed with a reference ointment Madecassol(®). Skin samples were also evaluated histopathologically. RESULTS: The results of these experimental studies exhibited that Verbascum mucronatum displays anti-inflammatory, antinociceptive and wound healing activities. Through bioassay-guided fractionation and isolation procedures four iridoid glucosides, ajugol (1), aucubin (2), lasianthoside I (3), catalpol (4), two saponins, ilwensisaponin A (5) and C (6) and a phenylethanoid glycoside, verbascoside (7) were isolated and their structures were elucidated by spectral techniques. Verbascoside (7) was found to possess significant wound healing activity as well as antinociceptive and anti-inflammatory potentials, per os without inducing any apparent acute toxicity or gastric damage. CONCLUSION: The experimental study revealed that Verbascum mucronatum displays remarkable antinociceptive, anti-inflammatory and wound healing activities.

An ethnopharmacological study on Verbascum species: from conventional wound healing use to scientific verification.

AIM OF THE STUDY: The leaves, flowers, and whole aerial parts of Verbascum L. (Scrophulariaceae) species are used to treat eczema and other types of inflammatory skin conditions and as a desiccant for wounds in Turkish traditional medicine. In the present study, the methanolic extracts of 13 Verbascum species growing in Turkey, including Verbascum chionophyllum Hub.-Mor., Verbascum cilicicum Boiss., Verbascum dudleyanum (Hub.-Mor.) Hub.-Mor., Verbascum lasianthum Boiss., Verbascum latisepalum Hub.-Mor., Verbascum mucronatum Lam., Verbascum olympicum Boiss., Verbascum pterocalycinum var. mutense Hub.-Mor., Verbascum pycnostachyum Boiss. & Heldr., Verbascum salviifolium Boiss., Verbascum splendidum Boiss., Verbascum stachydifolium Boiss. & Heldr and Verbascum uschackense (Murb.) Hub.-Mor. were assessed for their in vivo wound healing activity. MATERIAL AND METHODS: In vivo wound healing activity of the plants were evaluated by linear incision and circular excision experimental models subsequently histopathological analysis. The healing potential was comparatively assessed with a reference ointment Madecassol(®), which contains 1% extract of Centella asiatica. RESULTS: The methanolic extracts of Verbascum olympicum, Verbascum stachydifolium and Verbascum uschackense demonstrated the highest activities on the both wound models. Moreover, the methanolic extracts of Verbascum latisepalum, Verbascum mucronatum, and Verbascum pterocalycinum var. mutense were found generally highly effective. On the other hand, the rest of the species did not show any remarkable wound healing effect. Results of the present study support the continued and expanded utilization of these plant species employed in Turkish folk medicine. CONCLUSION: The experimental study revealed that Verbascum species display remarkable wound healing activity.

Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites.

The aqueous extract of Verbascum mucronatum Lam. along with its fractions and secondary metabolites were assessed for their antioxidant, acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) inhibitory activities. The antioxidant activity was evaluated by three methods: as 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, ferrous ion-chelating effect, and ferric-reducing antioxidant power (FRAP) tests. The AChE activity was determined by the Ellman method using an ELISA microplate reader. Phytochemical investigations revealed the presence of four iridoid glucosides, ajugol (1), aucubin (2), lasianthoside I (3) and catalpol (4), two saponins, ilwensisaponin A (5) and C (6), and a phenylethanoid glycoside, verbascoside (7), in Verbascum mucronatum. Their structures were elucidated by spectral techniques. The aqueous extract and fractions including the phenylethanoid glycoside 7 showed DPPH scavenger effect and had the best FRAP. Besides these results, one of the phenylethanoid fractions displayed the highest ferrous ion-chelating effect. While only 7 was found to possess moderate AChE inhibition, the extract, fractions, and all other tested compounds did not inhibit AChE and BChE.

Anti-inflammatory and antinociceptive potential of major phenolics from Verbascum salviifolium Boiss.

The potential effects of flavonoids, phenylethanoid and neolignan glycosides from the aerial parts of Verbascum salviifolium Boiss. were studied in the p-benzoquinone-induced writhing reflex, for the assessment of the antinociceptive activity, and in carrageenan- and PGE1-induced hind paw edema and 12-O-tetradecanoyl-13-acetate (TPA)-induced ear edema models in mice, for the assessment of the anti-inflammatory activity. Through bioassay-guided fractionation and isolation procedures ten compounds from the aqueous extract of the plant, luteolin 7-O-glucoside (1), luteolin 3'-O-glucoside (2), apigenin 7-O-glucoside (3), chrysoeriol 7-O-glucoside (4), beta-hydroxyacteoside (5), martynoside (6), forsythoside B (7), angoroside A (8), dehydrodiconiferyl alcohol-9'-O-beta-D-glucopyranoside (9) and dehydrodiconiferyl alcohol-9-O-beta-D-glucopyranoside (10), were isolated and their structures were elucidated by spectral techniques. Results have shown that 1, 2, 3 and 5 significantly inhibited carrageenan-induced paw edema at a 200 mg/kg dose, while 1, 2 and 5 also displayed anti-inflammatory activity against the PGE1-induced hind paw edema model. However, all the compounds showed no effect in the TPA-induced ear edema model. The compounds 1 and 2 also exhibited significant antinociceptive activity.

Screening for free radical scavenging and cell aggregation inhibitory activities by secondary metabolites from Turkish Verbascum species.

Free radical scavenging and cell aggregation inhibitory activities of 36 secondary metabolites isolated from the methanolic extracts of Verbascum cilicicum Boiss., V. lasianthum Boiss. ex Bentham, V pterocalycinum var. mutense Hub.-Mor., and V. salviifolium Boiss. (Scrophulariaceae) were investigated. The isolated compounds, 6-O-vaniloyl ajugol (1), ilwensisaponin A (2), ilwensisaponin C (3), verbascoside (4), beta-hydroxyacteoside (5), martynoside (6), poliumoside (7), forsythoside B (8), angoroside A (9), dehydrodiconiferyl alcohol-9-O-beta-D-glucopyranoside (10), dehydrodiconiferyl alcohol-9'-O-beta-D-glucopyranoside (11), apigenin 7-O-beta-glucopyranoside (12), luteolin 7-O-beta-glucopyranoside (13), luteolin 3'-O-beta-glucopyranoside (14) and chrysoeriol 7-O-beta-glucopyranoside (15), exhibited a dose-dependent inhibition of bioautographic and spectrophotometric DPPH activities. Verbascoside (4) was the most active (IC50 4.0 microg/ml) comparing it to vitamin C (IC50 4.4 microg/ml) to inhibit phorbol 12-myristate 13-acetate (PMA)-induced peroxide-catalyzed oxidation of 2',7'-dichlorofluorescein (DCFH) by reactive oxygen species (ROS) within human promyelocytic HL-60 cells. Ilwensisaponin A (2) (MIC 6.9 microg/ml) showed moderate in vitro activity on lymphocyte-associated antigen-1 (LFA-1)/intercellular adhesion molecule-1 (ICAM-1)-mediated aggregation using the HL-60 cell line [positive control was cytochalasin B (MIC 2.3 microg/ml)]. None of the other compounds showed free radical scavenging and cell aggregation inhibitory activities.

Estimation of antinociceptive and anti-inflammatory activity on Geranium pratense subsp. finitimum and its phenolic compounds.

To obtain experimental evidence on the therapeutic efficacy of Geranium species and its phenolic compounds for inflammatory diseases, we examined the effects of the aqueous extract of the aerial parts of Geranium pratense subsp. finitimum (Woronow) Knuth, its fractions and isolated compounds, the mixture of quercetin 3-O-alpha-arabinopyranoside, kaempferol 3-O-beta-galactopyranoside (1), the mixture of quercetin 3-O-beta-glucopyranoside, quercetin 3-O-beta-galactopyranoside (2), kaempferol 3-O-beta-glucopyranoside (3), (-)-6-chloroepicatechin (4), the mixture of quercetin 3-O-(2''-O-galloyl)-beta-glucopyranoside, quercetin 3-O-(2''-O-galloyl)-beta-galactopyranoside (5) and myricetin 3-O-(2''-O-galloyl)-beta-glucopyranoside (6), on carrageenan-, PGE(2)- and TPA-induced inflammation in mice and p-benzoquinone-induced writhing reflex to assess anti-inflammatory and antinociceptive activities. The effective dose of materials for the inhibition of carragenan-induced hind paw edema assay was determined to be 100 mg/kg, which was also used in the assays with the extract, its fractions and isolated compounds in all other experiments. The aqueous extract, 1, 2 (100 mg/kg), as well as indomethacin (10 mg/kg) inhibited significantly the formation of the carrageenan-induced hind paw edema. There was also a significant reduction in PGE(2)-induced hind paw edema and TPA-induced ear edema models with 5, in addition to the aqueous extract and the other active components 1 and 2. In the antinociceptive assay, the aqueous extract and its fractions, as well as 1, 2, and 5 diminished significantly the number of writhings. Based on the results obtained it is suggested that the aqueous extract of Geranium pratense subsp. finitimum and its phenolic compounds display anti-inflammatory activity, supporting the folkloric use.

Bioassay-guided isolation of anti-inflammatory and antinociceptive glycoterpenoids from the flowers of Verbascum lasianthum Boiss. ex Bentham.

Infusions of Verbascumlasianthum flowers have been used for hemorrhoids in Turkish folk medicine. In order to evaluate the scientific basis for this practice, in vivo anti-inflammatory and antinociceptive activities of Verbascum lasianthum Boiss. ex Bentham flowers were investigated. A methanolic extract of the flowers was shown to possess significant inhibitory activity in the carrageenan-induced hind paw edema model and in p-benzoquinone-induced writhings in mice. Through bioassay-guided fractionation and isolation procedures eight compounds, 6-O-(4'''-O-trans-p-coumaroyl)-alpha-L-rhamnopyranosylaucubin (1), 6-O-(4'''-O-trans-p-methoxycinnamoyl)-alpha-L-rhamnopyranosylaucubin (2), sinuatol (3), aucubin (4), geniposidic acid (5), catalpol (6), ajugol (7) and ilwensisaponin A (8) were isolated and their structures were elucidated by spectral techniques. An iridoid glucoside, aucubin (4) and a triterpenoid saponin, ilwensisaponin A (8) were found to possess significant antinociceptive and anti-inflammatory activities, per os without inducing any apparent acute toxicity or gastric damage. Results of the present study support the continued and expanded utilization of plants employed in Turkish folk medicine.

Antinociceptive and anti-inflammatory effects of saponin and iridoid glycosides from Verbascum pterocalycinum var. mutense Hub.-Mor.

The anti-inflammatory and antinociceptive properties of four major compounds from the flowers of Verbascum pterocalycinum var. mutense were investigated. Saponin glycosides called ilwensisaponin A and C and iridoid glycosides known as ajugol and picroside IV were isolated from the methanolic extract. A dose-related anti-inflammatory and antinociceptive response were obtained in this study at doses of 100 and 200 mg/kg. The results of the evaluation of the anti-inflammatory activity induced by carrageenan and PGE1 showed that this species possesses active constituents that could diminish the cyclooxygenase activitiy. No effects were observed in the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema model. Our results support the anti-inflammatory and analgesic effects of Verbascum pterocalycinum var. mutense. Ilwensisaponins A and C could explain in part the anti-inflammatory and analgesic activities of this species. Although antinociceptive and anti-inflammatory activities of ajugol and picroside IV were found insignificant in the statistical analysis, ilwensisaponin A and C showed notable activity without inducing any apparent acute toxicity as well as gastric damage.