Fatty acid composition and chemotaxonomic evaluation of species of Stachys

The fatty acid composition of the seed oil of 23 Stachys taxa was analysed by GC/MS. The main compounds were found to be linoleic (27.1-64.3%), oleic (20.25-48.1%), palmitic (4.3-9.1%), stearic (trace to 5.2%) and 6-octadecynoic (2.2-34.1%) acids. The latter compound could be used as a chemotaxonomic marker of the genus Stachys. A cluster analysis was performed for comparison and characterisation of the seed oil from Stachys species.     

Monoterpenoids from Stachys glutinosa L

The iridoidic composition of Stachys glutinosa L. was examined in comparison with the results obtained in the phytochemical studies on S. corsica Pers. The presence of the known harpagide and acetyl-harpagide were showed together with that of a new di-glycosidic iridoid. The structure of this new compound, the 5-allosyloxy-aucubin, was demonstrated by comparison with the spectroscopical data of monomelittoside and of its 5-O-glucosyl-derivative, the melittoside. The presence of allose in Stachys genus seems to be a chemotaxonomical character.     

Lavandulifolioside B: a new phenylethanoid glycoside from the aerial parts of Stachys lavandulifolia Vahl

Reversed-phase preparative HPLC analyses of the methanol extract of the aerial parts of Stachys lavandulifolia afforded a new phenylethanoid glycoside, 4,3',4'-trimethoxy-lavandulifolioside A, named lavandulifolioside B, together with three other known phenylethanoid glycosides, lavandulifolioside A, verbascoside and leucosceptoside A, and an iridoid glycoside 5-O-β-allopyranosyloxy-aucubin (5-O-β-allopyranosyl-monomelittoside). While the structures of the known compounds, except the iridoid glycoside, were established by direct comparison of their spectroscopic data with respective literature data, lavandulifolioside B and 5-O-β-allopyranosyloxy-aucubin were identified comprehensively by extensive 1D and 2D NMR analyses. The distribution of the isolated compounds within the genus Stachys has been discussed.     

Iridoids of Stachys Species Growing in Hungary

JPC – Journal of Planar Chromatography – Modern TLC - Stachys species contain iridoids, for example harpagide, acetylharpagide, aucubin, harpagoside, and ajugoside. The iridoid...     

Determination of Stachys palustris Iridoids by a Combination of Chromatographic Methods

JPC – Journal of Planar Chromatography – Modern TLC - Stachys palustris L. (Lamiaceae) contains the iridoids harpagide and acetylharpagide. The presence of other components, for example...     

TLC and GC Analysis of the Essential Oils of Stachys Species

JPC – Journal of Planar Chromatography – Modern TLC - Species of the Lamioideae subfamily of the family Lamiaceae, including Stachys species, do not contain much essential oil. The...     

HPTLC Determination of Flavonoids and Phenolic Acids in Some Croatian Stachys Taxa

JPC – Journal of Planar Chromatography – Modern TLC - Stachys is a large genus belonging to the family Lamiaceae. In common with many other representatives of this family, the aerial...     

Chemistry of plants from Crete: stachyspinoside, a new flavonoid glycoside and iridoids from Stachys spinosa

The new flavonoid glycoside stachyspinoside (1), and the three iridoids, 7-O-acetyl-8-epi-loganic acid (2), ajugol (3) and harpagide (4) were isolated from Stachys spinosa. The structures of these compounds were established on the basis of mass spectrometry (ESMS and tandem MS), one- and two-dimensional nuclear magnetic resonance experiments (COSY, COSY LR, HMQC, TOCSY and HMBC) as well as simple chemical derivatization.     

Determination of the volatile constituents and total phenolic contents of some endemic Stachys taxa from Turkey

The total phenolic contents and the essential oil compositions of the previously unknown Stachys taxa (Labiatae), including Stachys pinardii Boiss, Stachys cretica L. subsp. mersinaea (Boiss.) Rech., and Stachys aleurites Boiss. & Heldr., all endemic to Turkey, were studied. Their essential oil compositions were investigated by GC-MS. It was found that the main constituents were α-curcumene (34.10%) for S. cretica, cedrandiol (25.26%) and caryophyllene dioxide (22.15%) for S. pinardii, and (Z)-β-caryophyllene (31.60%) for S. aleurites. The total phenolic contents, by the Folin-Ciocalteu colorimetric method, of the S. pinardii, S. cretica subsp. mersinaea, and S. aleurites methanolic extract were found to be 600.74±0.23, 1200.94±0.11, and 900.61±0.06 mg gallic acid equivalent (GAE)/100 g in dried herb, respectively. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 141–143, March–April, 2006.     

Lavandulifolioside: A New Phenylpropanoid Glycoside from Stachys lavandulifolia

A new phenlypropanoid glycoside has been isolated from the methanolic extract of the aerial parts of Stachys lavandulifolia (Lamiaceae), lavandulifolioside (1) . On the basis of chemical and spectral data the structure of the new compound 1 has been elucidated as β-(3,4-dihydroxyphenyl)ethyl O-α-L -arabinopyranosyl-(1→2)-α-L -rhamnopyranosyl-(1→3)-4-O-caffeoyl-β-D -glucopyranoside.     

Structure of stachysolone

Summary It has been shown that stachysolone — a bitter substance fromStachys annua L. — is a diterpenoid with a rearranged labdane hydrocarbon skeleton of the kolavane type. Structural formula (I) has been established for stachysoloneInstitute of Chemistry, Academy of Sciences of the Moldavian SSR. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czechoslovakian SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 295–299, May–June, 1972.     

Composition of the essential oils and antibacterial activities of Hymenocrater yazdianus, Stachys obtusicrena and Nepeta asterotricha three Labiatae herbs growing wild in Iran

Water-distilled essential oils from leaves of Hymenocrater yazdianus Rech.f., flowers of Stachys obtusicrena Boiss., and stems and flowers of Nepeta asterotricha Rech.f., which are endemic to Iran, were analyzed by GC and GC/MS. Fifty-five components of the leaf oil of H. yazdianus were characterized, representing 95.1% of the total components detected. The major constituents were identified as 1,8-cineole (17.6%), beta-caryophyllene (13.9%), alpha-pinene (10.6%) and caryophyllene oxide (10.4%). Germacrene-D (37.5%) and alpha-bisabolol (23.5%) were the main components among the twenty constituents characterized in the flower oil of S. obtusicrena, representing 90.8% of the total components detected. Thirty-five compounds representing 93.0% of the stem oil of N. asterotrica were identified among which terpinen-4-ol (22.8%) and gamma-terpinene (14.1%) were the major ones. The flower oil of the species was characterized by higher amounts of terpinen-4-ol (24.8%), 4a alpha, 7a beta-nepetalactone (18.2%) and 1,8-cineole (11.6%) among the thirty-three components comprising 98.5% of the total oil detected. The antibacterial activity of the stem, leaf and flower oils of Hymenocrater yazdianus, Stachys obtusicrena and Nepeta asterotricha against seven Gram-positive and Gram-negative bacteria were determined using the MIC method. The growth inhibitory zone (mm) was also measured.     

New terpenoids from Stachys parviflora Benth

Two new triterpenoidal saponins were isolated from the n-butanolic extract of Stachys parviflora (Lamiaceae). Their structures were elucidated on the basis of spectral data as stachyssaponin A; 3beta, 15alpha, 19alpha, 21beta, 22alpha-pentahydroxyolean-12-ene-28-oic acid 3-O-{alpha-L-rhamnopyranosyl-(1 --> 3)-beta-D-glucopyranoside}-22-O-{alpha-L-arabinofuranosyl-(1 --> 3)-beta-D-glucopyranoside} (1) and stachyssaponin B; 2beta, 3beta, 15alpha, 21beta-tetrahydroxyolean-12-ene-28-oic acid 2-O-[alpha-L-arabinofuranoside]-3, 21-bis-O-[beta-D-glucopyranoside] (2).     

The Composition of the Essential Oil of Stachys iberica Subsp. Stenostachya Growing In Turkey

The water distilled essential oil from dried aerial parts ofStachys ibericasubsp.stenostachya(Lamiaceae) was analyzed by GC/MS. Seventy-one compounds were characterized representing 96% of the oil. The main constituents were found as linalyl acetate (42.2%), linalool (18.9%), geranyl acetate (8.2%), and -terpineol (5.3%).     

Structure and absolute configuration of new acidic metabolites from Stachys ehrenbergii

Two novel metabolites have been isolated from the aerial parts of Stachys ehrenberiigii. Their structures and stereochemistry were elucidated using a combination of ¹³C and ¹H homo and heteronuclear 2D NMR experiments and mass analysis. The development of an enantioselective synthesis of 3-(2′-acetoxy-4-phenylbut-3′-enoylamino)propionic acid allowed to confirm the structure and assign the (R) absolute configuration at C-2′ of the natural product.     

Composition of the essential oil of Stachys benthamiana Boiss. from the south of Iran

The chemical composition of the essential oil (EO) obtained from the aerial parts of Stachys benthamiana Boiss. was analysed by using GC and GC/MS. Thirty-three components were identified in the oil. β-Bisabolene (19.2%), humulene epoxide II (10.7%), epi-α-bisabolol (7.2%), (E)-γ-bisabolene (6.9%), n-decanal (6.8%) and caryophyllene oxide (6.6%), were the main compounds in the EOs. This is the first report on the different chemical compositions of S. benthamiana EOs from the south of Iran.     

A new rosane-type diterpenoid from Stachys parviflora and its density functional theory studies

A new rosane-type diterpenoid (1) has been isolated from the chloroform fraction of Stachys parviflora. Structure of 1 was proposed based on 1D and 2D NMR techniques including correlation spectroscopy, heteronuclear multiple quantum coherence, heteronuclear multiple bond correlation and nuclear Overhauser effect spectroscopy. A theoretical model for the electronic and spectroscopic properties of compound 1 is also developed. The geometries and electronic properties were modelled at B3LYP/6-31G^* and the theoretical scaled spectroscopic data correlate nicely with the experimental data.     

Acetylspectabiflaside fromStachys atherocalyx

From the herbage ofStachys atherocalyx C. Koch, a new flavonoid glycoside has been isolated — acetylspectabiflaside, with mp 237–242°C. On the basis of acetylation, the formation of a hydroxamic acid, alkaline, and enzymatic hydrolysis, and oxidative degradation, and also the results of UV, IR, and PMR spectroscopy, the structure of 4′,5,7,8-tetrahydroxy-3′-methoxyflavone 7-O-{acetyl-[O-β-D-glucopyranosyl-(1→2)-β-D-mannopyranoside]} has been proposed for acetylspectrabiflaside.     

Essential Oil Composition and Antibacterial Activity of the Leaves of <Emphasis Type="Italic">Stachys schtschegleevii</Emphasis> from Iran

The composition of the essential oil obtained by hydrodistillation from the leaves of Stachys schtschegleevii Sosn. before the flowering stage was analyzed by GC and GC-MS. Forty-five compounds representing 98.7% of the total oil were identified, of which α-pinene (36.4%), germacrene-D (18.6%), limonene (8.2%), and piperitone (6.2%) were the major constituents. Furthermore, antibacterial activity of the entire oil and its two main monoterpenes was evaluated against six Gram-positive and Gram-negative bacteria. The oil exhibited moderate activity against the tested bacteria.__________Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 138–140, March–April, 2005.     

Essential oil composition and antioxidant activity of Stachys sylvatica L. (Lamiaceae) from different wild populations in Kosovo

Leaves and inflorescences of Stachys sylvatica L. (Lamiaceae) were collected from three different wild populations in Kosovo to study the natural variation of the chemical composition of essential oils, total flavonoids, total phenolics and the antioxidant activity. Essential oils were obtained by steam distillation and analysed by GC-FID and GC-MS, whereas total flavonoids, total phenolics and antioxidant activities were determined by spectrophotometric methods. Yields of essential oils ranged from 0.001% to 0.007% (v per dry weight). Twenty-eight volatile constituents were identified. The main constituents were α-pinene, β-pinene and germacrene-D. Total phenolics ranged from 39.3 to 70.8?mg?g?1 dry mass, whereas total flavonoid content ranged from 30.44 to 70.63?mg?g?1 dm. The antioxidant activity, as measured by the DPPH method, exhibited a rather high degree of activity ranging from 25.5% to 57.2%, whereas the FRAP antioxidant activity showed a lower variability and ranged from 93 to 133.4?mg?g?1 dm.