Terpenoids and sterols from Nepeta cataria L. var. citriodora (Lamiaceae)

Isolation and GC/MS quantitative determination of ursolic acid in the herb of Nepeta cataria var. citriodora have been performed. The content of this compound was in the range 0.95-1.30%. Daucosterol (beta-sitosterol 3-O-beta-D-glucoside) was also isolated from the plant, in addition to small amounts of beta-sitosterol, campesterol, alpha-amyrin and beta-amyrin. The content and composition of essential oil in samples of the Nepeta cataria var. citriodora herb have been analysed as well.     

Flavonoids and free phenolic acids from Phytolacca americana L. leaves

In the leaves of Phytolacca americana L. flavonoid compounds: kaempferol 3-O-beta-D-glucopyranoside, kaempferol 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranoside, kaempferol 3-O-alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranoside, kaempferol 3-O-diglucoside and quercetin 3-O-glucoside were identified by chemical and spectroscopic methods and using co-chromatography, phenolic acids: p-hydroxybenzoic, vanillic, synapic, p-coumaric ferulic and caffeic were also confirmed.     

Flavonoids from lemon balm (Melissa officinalis L., Lamiaceae)

Six flavonoids have been isolated from the leaves of lemon balm (Melissa officinalis L., Lamiaceae). Their structures were determined on the basis of spectral data (UV, 1R, 1H NMR, 13C NMR and FAB MS) as luteolin, luteolin 7-O-beta-D-glucopyranoside, apigenin 7-O-beta-D-glucopyranoside, luteolin 7-O-beta-D-glucuronopyranoside, luteolin 3'-O-beta-D-glucuronopyranoside and luteolin 7-O-beta-D-glucopyranoside-3'-Obeta-D-glucuronopyranoside. The last three glycosides have been found in lemon balm for the first time and luteolin 7-O-beta-D-glucopyranoside-3'-O-beta-D-glucuronopyranoside is a new compound found in plants.     

Nepeta sibthorpii Bentham (Lamiaceae): micromorphological analysis of leaves and flowers

Nepeta sibthorpii Bentham (Lamiaceae) is an herbaceous aromatic plant, growing in dry, usually rocky areas of Southern Greece. In this paper, we report the study of micromorphological features of the flowers and leaves of Nepeta sibthorpii Bentham. The analysis by means of scanning electron microscopy has permitted to characterize both the covering trichomatous garment, abundantly present on the calyx and on the leaves, and the glandular hairs, distributed on the adaxial leaf surface and on the outer surfaces of calyx and corolla, showing also the peculiar features of the epidermal cells, all useful diagnostic elements for the identification of this medicinal plant.     

The effect of Nepeta cataria extract on adherence and enzyme production of Staphylococcus aureus.

Nepeta cataria L., commonly known as catnip, is a perennial herb with a considerable folkloric reputation. A diethyl ether extract of this plant has been shown to have antimicrobial activity against fungi and Gram-positive bacteria. The aim of this work was to study the activity of N. cataria extract on 44 Staphylococcus aureus strains, some resistant to methicillin, and S. aureus 6538P (American Type Culture Collection) by evaluating the effect of subminimum inhibitory concentrations on coagulase, DNAse, thermonuclease and lipase production, and on in-vitro adherence. DNAse, thermonuclease and lipase were inhibited by concentrations equal to 1/2 and 1/4 MIC. A reduction of adherence was also observed.     

Variation of free phenolic acids in medicinal plants belonging to the Lamiaceae family.

Ten species belonging to the family Lamiaceae and representing the most popular medicinal plants used in Polish phytotherapy were examined for the content of free phenolic acids (PhAs). Two depsides, rosmarinic and chlorogenic acids, as well as eight simple PhAs, protocatechuic, gentisic, p-hydroxybenzoic, caffeic, vanillic, syringic, p-coumaric and ferulic acids, in different qualitative and quantitative proportions depending on the plant examined were determined by the rapid, selective and accurate method combining solid-phase extraction and high-performance liquid chromatography.     

Flavonoids in Scutellaria immaculata and S. ramosissima (Lamiaceae) and their biological activity

Objectives The aim of this study was to investigate the flavonoid composition of Scutellaria immaculata and S. ramosissima (Lamiaceae) and the in‐vitro biological activity of their extracts and flavonoids. Methods The flavonoid composition of S. immaculata (Si) and S. ramosissima (Sr) were analysed using LC‐MS. Antimicrobial activity was studied in vitro against a range of bacteria and fungi using diffusion and microdilution methods. Anti‐trypanosomal and cell proliferation inhibitory activity of the extracts and flavonoids was assessed using MTT. The antioxidant activity of the flavonoids and extracts were evaluated using DPPH* test. Key findings LC‐MS investigation of Si and Sr plants allowed the identification, for the first time, of an additional 9 and 16 flavonoids, respectively. The methanol, chloroform and water extracts from these plants and six flavonoids (scutellarin, chrysin, apigenin, apigenin‐7‐O‐glucoside, cynaroside and pinocembrine) exhibited significant inhibition of cell growth against HeLa, HepG‐2 and MCF‐7 cells. The chloroform extract of Sr showed potent cytotoxic effects with IC50 (drug concentration which resulted in a 50% reduction in cell viability) values of 9.25 ± 1.07 µg/ml, 12.83 ± 1.49 µg/ml and 17.29 ± 1.27 µg/ml, respectively. The highest anti‐trypanosomal effect against T. b. brucei was shown by the chloroform extract of Sr with an IC50 (drug concentration which resulted in a 50% inhibition of the biological activity) of 61 µg/ml. The pure flavonoids showed an IC50 range between 3 and 29 µm , with cynaroside as the most active compound with an IC50 value of 3.961 ± 0.133 µm . The chloroform extract of Sr has potent antimicrobial activity against Streptococcus pyogenes (minimum inhibitory concentration, MIC = 0.03 mg/ml). Pinocembrine exhibited a strong activity against the all bacteria except Escherichia coli and yeasts. Water extracts of Sr and Si exhibited potent antioxidant activity with IC50 values of 5.62 ± 0.51 µg/ml and 3.48 ± 0.02 µg/ml, respectively. Scutellarin exerted stronger antioxidant activity than other flavonoids. Conclusions This is the first study reporting an in‐vitro biological investigation for Si and Sr. Especially the chloroform extract of Sr showed potent anticancer and antimicrobial activity. Cynaroside had a highly selective and strong cytotoxicity against T. b. brucei while showing only mild effects against cancer cells.     

不同采收期兴安升麻中3种酚酸类成分和总酚酸的含量测定

目的测定不同采收期兴安升麻根茎与须根中咖啡酸、阿魏酸、异阿魏酸及总酚酸的含量,考察不同采收期兴安升麻中酚酸类的含量变化。方法咖啡酸、阿魏酸和异阿魏酸的含量测定采用HPLC法。色谱柱为Thermo C18(250 mm×4.6 mm,5μm)柱,流动相为乙腈-体积分数0.1%磷酸水溶液,进行梯度洗脱,检测波长为316 nm,进样量为10μL,流速为1.0 m L·min-1,柱温为25℃。总酚酸的含量测定采用紫外-可见分光光度法,以咖啡酸为对照品,质量分数0.5%K3[Fe(CN)6]-质量分数1%Fe Cl3(体积比1∶1)混合溶液为显色剂,在745 nm波长处进行测定。结果在每年6至10月不同采收期的兴安升麻中,咖啡酸在须根中的含量较少甚至检测不到(0~0.035%),在根茎中的质量分数为0.018%~0.054%;阿魏酸在根茎与须根中的质量分数分别为0.014%~0.066%和0.013%~0.141%;异阿魏酸在根茎与须根中的质量分数分别为0.069%~0.206%和0.167%~0.785%。总酚酸的质量分数在0.87%~4.56%内。结论兴安升麻中总酚酸与3种酚酸的含量在不同采收期变化较大,总体上兴安升麻中酚酸类成分含量较高,具有较好的研究和开发价值。     

Chemical composition and larvicidal activity of essential oils from Peganum harmala,Nepeta cataria and Phellodendron amurense against Aedes aegypti (Diptera: Culicidae)

Essential oils from aerial parts of the herbs Peganum harmala and Nepeta cataria, and leaves of the tree Phellodendron amurense were analyzed by GC-FID and GC-MS, and their larvicidal activities were assayed on the early fourth instar larvae of Aedes aegypti. The major constituents of the oils were limonene (14.5%) and thymol (11.5%) in P. harmala, thymol (46.5%), 4aα,7α,7aβ-nepetalactone (18.3%) and 4aα,7β,7aα-neptalactone (19.7%) in N. cataria, eugenol (14.5%) andγ-eudesmol (9.5%) in P. amurense.The oil of N. cataria had a strong larvicidal activity (LC₅₀ < 50 µg/mL; LC₉₀ < 86.8 µg/mL) on A. aegypti while the remaining oils showed a moderated killing effect. The larvicidal activity of N. cataria oil was associated to the contents of 1,8-cineol, camphor, 4aα,7α,7aβ-Nepetalactone, 4aα,7β,7aα-Nepetalactone and thymol. Our results indicate that the oil of N. catariadeserves to be used as a source of larvicidal agents against A. aegypti.     

Flavonoids from flowers of Malva crispa L. (Malvaceae)

The following flavonoids were isolated and identified from the flowers of Malva crispa L.: kaempferol 3-O-beta-glucopyranoside, 3-O-(6"-tran-p-coumaroyl)-beta-D-glucopyranoside, 7-O-beta-D-glucopyranoside, 3-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside and 3,7-O-diglucoside as well as quercetin 3-O-beta-D-glucopyranoside, 3-O-alpha-L-rhamnopyranosyl (1-->6) -beta-D-glucopyranoside and apigenin 7-O-beta-D-glucopyranoside. Their structures were established by chemical analysis, UV, 1H and 13C NMR spectrometry.     

Free and chemically bonded phenolic acids in barks of Viburnum opulus L. and Sambucus nigra L

Liquid column chromatography, planar chromatography (TLC) on modified and unmodified silica layers, reversed-phase high-pressure liquid chromatography (HPLC), as well as ESI-TOF MS and 1H-NMR have been used for separation, purification and identification of phenolic acids in the barks of Sambucus nigra and Viburnum opulus (Caprifoliaceae). By the use of these procedures three cinnamic acid derivatives: caffeic acid, p-coumaric, and ferulic acid, four benzoic acid derivatives: gallic acid, protocatechuic acid, syringic acid, 3,4,5-trimethoxybenzoic acid, two phenylacetic acid derivatives: 3,4-dihydroxyphenylacetic acid, homogentisic acid, and two depsides: chlorogenic acid and ellagic acid were detected and identified in the bark of Viburnum opulus. Caffeic acid, p-coumaric acid, ferulic acid, gallic acid, syringic acid, 3,4,5-trimethoxybenzoic acid and chlorogenic acid were also detected and identified in the bark of Sambucus nigra. Except for chlorogenic acid, this is the first time these phenolic acids have been isolated, detected, and identified in the bark of V. opulus and S. nigra.     

In vitro screening for antitumour activity of Clinopodium vulgare L. (Lamiaceae) extracts

Aqueous extract of Clinopodium vulgare L. showed strong antitumour activity when tested in vitro on A2058 (human metastatic melanoma), HEp-2 (epidermoid carcinoma, larynx, human) and L5178Y (mouse lymphoma) cell lines-6 h after treatment disintegration of the nuclei and cell lysis started. Applied at a concentration of 80 microg/ml it reduced the cell survival to 1.0, 5.6 and 6.6%, respectively. The concentrations of aqueous extract inhibiting the growth of A2058, HEp-2 and L5178Y cells by 50% (IC50 values) were calculated to be 20, 10 and 17.8 microg/ml respectively. Two groups of active substances were detected: the first one, probably combining glycosides, influenced adhesion, while the second one caused massive cell vacuolisation. The chloroform extract, which contained ursolic acid and gentriacontan had also cytotoxic, however a little bit weaker effect. All changes observed were irreversible.     

Two new aromatic acids from Clerodendrum formicarum Gurke (Lamiaceae) of Cameroon

The ethanolic extract of the leaves of Clerodendrum formicarum, a Lameacious plant of Cameroon, afforded two new salicylic acid derivatives named formoic acids A and B along with four known constituents which have been obtained for the first time from this source. They include flemingipanic acid, martynoside, verbascoside, and seguinoside K. Structures of all the isolated constituents have been elucidated with the aid of 1D and 2D NMR spectroscopic techniques.     

Qualitative and quantitative analysis of phenolic acids in Asclepias syriaca L

TLC and HPLC was applied to qualitative and quantitative determination of phenolic acids free and liberated by acid and alkaline hydrolysis in common milkweed. The presence of phenolic acids, namely p-hydroxybenzoic, p-coumaric, protocatechuic and caffeic acids, was confirmed in the leaves and flowers. Moreover, the flowers contained gallic acid, and the leaves contained alpha-resorcylic, vanilic and chlorogenic acids. Conjugated forms of phenolic acids predominate in the plant. They hydrolyse mainly to coffeic, p-coumaric, ferulic and p-hydroxybenzoic acids.     

Gastroprotective activity of methanol extract and marrubiin obtained from leaves of Marrubium vulgare L. (Lamiaceae)

Objectives The purpose of this study was to assess the gastroprotective properties of the methanol extract and the diterpene marrubiin obtained from the leaves of M. vulgare. Methods Assays were performed using different protocols in mice. Studies focusing on mechanisms of gastroprotection were also undertaken. Key findings In the model of ethanol‐induced ulcers, we observed a significant reduction in all the parameters analysed; the curative ratios obtained were 49.31 ± 0.57, 74.31 ± 0.91 and 79.86 ± 0.59 for the groups treated with 50 and 100 mg/kg of extract of M. vulgare and omeprazole (30 mg/kg), respectively. For indomethacin‐induced ulcers, the percentages of ulcer inhibition were 50.32 ± 5.60, 66.24 ± 4.30, 82.17 ± 04.09 and 67.52 ± 4.38, for the groups treated with 25, 50 and 100 mg/kg M. vulgare and positive control (cimetidine), respectively. In both models, the marrubiin (25 mg/kg) produced a significant reduction in all the parameters when compared with the control group (P < 0.01). There was also a significant increase in pH and mucus production in the groups treated with M. vulgare extract and marubiin. The results also demonstrated that the gastroprotection induced by the extract and marubiin is related to the activity of nitric oxide and endogenous sulfhydryls, which are important gastroprotective factors. Conclusions The results of this study show that the extract of M. vulgare and marrubiin displays antiulcer activity and that this effect can be partly attributed to the isolated diterpene.