[Isolation and structure elucidation of secondary metabolites from aerial part of hippomarathrum microcarpum]

Apiaceae family is one of the largest plant families with wide distribution all around the world. The genus Hippomarathrum has 28 species around the world which among them the species H. microcarpum outspread in the North, Northwest, West and Central of Iran, and also Turkey, Caucasus and Iraq. In this study, the main compounds in ethyl acetate extract from aerial parts of the plant Hippomarathrum microcarpum have been studied. The isolation and purification of the compounds were carried out using column chromatography. The structure of isolated compound established according 1H-NMR and 13C-NMR spectral data. Two coumarins [osthole and isoimperatorin] and one sterol [beta-sitosterol] have been isolated and identified from ethyl acetate extract. The presence of coumarines like osthole and isoimperatorin in H. microcarpum cause of the importance of this plant. This coumarines have verity of usages in traditional medicine and recent studies have supported most of these usages and revealed new effects of these coumarines. As regard that more research haven't been done about this plant and also because of significance effects of isolated coumarines, it seems necessary to perform further studies on biological effects of this plant

review on phytochemistry and medicinal properties of the genus Achillea

Achillea L. [Compositae or Asteraceae] is a widely distributed medicinal plant throughout the world and has been used since ancient time. Popular indications of the several species of this genus include treatment of wounds, bleedings, headache, infammation, pains, spasmodic diseases, fatulence and dyspepsia. Phytochemical investigations of Achillea species have revealed that many components from this genus are highly bioactive. There are many reports on the mentioned folk and traditional effects. Although, the medicinal properties of Achillea plants are recognized worldwide, there are only one review article mainly about the structures of the phytochemical constituents of Achillea. The present paper reviews the medicinal properties of various species of Achillea, which have been examined on the basis of the scientifc in vitro, in vivo or clinical evaluations. Various effects of these plants may be due to the presence of a broad range of secondary active metabolites such as favonoids, phenolic acids, coumarins, terpenoids [monoterpenes, sesquiterpenes, diterpenes, triterpenes] and sterols which have been frequently reported from Achillea species

Sterols and flavonoids of lomatopodium staurophyllum

The genus Lomatopodium Fisch. And amp; C.A.Mey., belongs to Apiaceae family and contains one herbaceous species growing wildly in Iran. There are only a few papers about the chemical constituents of these plants. Here, we focused on the isolation and identification of the main flavonoid glycosides and sterols from the aerial parts of L. staurophyllum, which has not been previously reported. Flowered aerial parts of the plant were dried and cut into small pieces, then extracted with ethyl acetate and methanol by percolation at room temperature. The separation process was carried out using several chromatographic methods. Structural elucidation was based on NMR and MS data, in comparison with those reported in the literature. The isolated compounds from ethyl acetate and methanol extracts of L. staurophyllum were identified as nonanal [1], stigmasterol acetate [2], beta-sitosterol [3], quercetin 3-O-glucoside [4] and quercetin 3 - O - rhamnoglucoside [5] by comparison of their NMR spectral data with those reported in the literature. Ethyl acetate and methanol extracts of L. staurophyllum contain various flavonol glycosides and sterols as the main components. Pelargonic aldehyde [nonanal], a growth promoting factor in plant cells, is found to be occurred in this species and might be a cause of anti -diarrhea activity

Tryptophan and sterols from salvia limbata

Salvia limbata is an aromatic herbaceous plant and grows widely in Iran Turkey and Afghanistan. In the previous study, six flavones together with rosmarinic acid were isolated from the ethyl acetate and methanol extracts of S. limbata. In this report, we focused on the isolation and identification of the glycosylated sterols and the main accumulated amino acid of the species S. limbata, which has not been previously reported. Aerial parts of the plant were dried, cut into small pieces and extracted with ethyl acetate and methanol by percolation at room temperature. The separation process was carried out using several chromatographic methods. Structural elucidation was based on NMR data, in comparison with those reported in the literature. The isolated compounds [Figure 1] from the ethyl acetate and MeOH extracts of S. limbata were identified as beta-sitosterol [1], stigmasterol [2], daucosterol [3], stigmasterol 3- O-glucoside [4] and tryptophan [5] by comparison of their NMR spectral data with those reported in the literature S. limbata can accumulate the tryptophan as a major free amino acid together with sterols and their glucosides. Therefore, consumption of S. limbata [as a herbal tea or other preparations], which contains the essential amino acid tryptophan, might be useful for dietary deficiency of tryptophan

Antioxidant activity of some medicinal species using FRAP assay

Medicinal plants [especially belong to Lamiaceae family] are potential sources of new drugs to improve the treatment of diseases whose treatment is associated to anti-oxidative agents. In this paper, the Ferric Reducing Ability of Plasma [FRAP] activity of some Lamiaceae and Apiaceae species, has been evaluated. Aerial parts of the plants were dried, cut into small pieces and extracted with ethyl acetate and methanol, respectively, by percolation at room temperature. Different concentrations of the plant extracts were investigated for antioxidant power using FRAP assay. The extracts showed a considerable antioxidant effect from 16.36 mmol of FeSO[4]/100 g dry plant equivalents in Scutellaria tornefortii [AcOEt extract] to 404.12 mmol of FeSO[4]/100 g dried plant in Salvia macrosiphon [MeOH extract]. All the plant samples possessed antioxidant activity, while Salvia macrosiphon [MeOH extract], Pimpinella tragioides [MeOH extract] and Salvia limbata [AcOEt extract] showed significantly the highest results and Scutellaria tornefortii [AcOEt extract] showed the lowest power. Antioxidant activity of these species might be due to the presence of flavonoids, rosmarinic acid, coumarins even monoterpenes [like myrcene] in the plant extracts

Lignans and neolignans from Stelleropsis antoninae

Stelleropsis antoninae Pobed. [Family: Thymelaeaceae] grows wildly as an herbaceous plant in Iran. Most of the Thymelaeaceous plants contain lignans and neolignans, which have important pharmacologically properties. In the present study, the isolation and identification of the main lignans and neolignans of S. antoninae, which has not been previously reported is described and compared to other species. Column [CC] and High Performance Liquid Chromatographic [HPLC] methods were used for the isolation and purification, and 1H-NMR, 13C-NMR, HMBC, HMQC, H-H COSY and MS were employed for the identification of the compounds isolated from the methanol extract. From the methanol extract of the aerial parts of S. antoninae four lignans, syringaresinol [1], syringaresinol 4-O-beta-D-glucopyranoside [4], syringaresinol 4-O-beta-D-glucopyranosyl-[1-6]-beta-D-glucopyranoside [5], liriodendrin [6], and two neolignans, 5-methoxylariciresinol 4'-O-beta-D-glucopyranoside [3] and dehydrodiconiferyl alcohol 4-O-beta-D-glucopyranoside [2] were isolated and identified. The results of this study show that siringaresinol, a well-known bioavtive compound, and its glucosides are the main lignans, and lariciresinol and coniferyl alcohol derivatives are the main neolignans of S. antoninae

Brine shrimp cytotoxicity of some medicinal plants Belongs to Lamiaceae, Asteracea, Rosaceae and Boraginaceae Families

In this report, we evaluated the cytotoxic activity of the hexane, ethyl acetate, methanol and aqueous methanol extracts of the aerial parts of some species belongs to Lamiaceae, Boraginaceae, Asteraceae and Rosaceae families. In order to examine the cytotoxicity of the plant extracts, Brine Shrimp Cytotoxicity Assay was used against Artemia salina larva. Results showed that Scutellaria Tornefortii indicated cytotoxic activity against the larva of Artemia salina. The minimum lethal concentration of its aqueous methanol extract, as the most effective extract, was 6 g/ml compared to berberine hydrochloride as the positive control [LC[50]=26 microg/ml]. EtOAc extract of Rubus hyrcanus was also a potent cytotoxic extract [LC[50]=28 microg/ml]. In addition to those mentioned plants, Echium amoenum, Onosma bulbotrichum, Stachys byzanthina and Rubus discolor could be the potential sources of cytotoxic components. Some of the medicinal plants, growing widely in north part of Iran, are effective against the larvae of A. salina, so they could be a promising source of anti-cancer and anti-tumor compounds

Cytotoxic flavonoid from Achillea talagonica Bioss

Achillea talagonica [Asteraceae] is an endemic herbaceous plant in Iran with small yellow flowers and several times pinnately divided leaves in worm shape. The plant was found to be cytotoxic in our previous studies. A. talagonica was collected in May 2005 from Talegan in north of Iran during the full flowering stage. Dried aerial parts of the plant were reduced in to small pieces and percolated with ethyl acetate for 72 hours. The extract obtained was filtered and then concentrated under reduced pressure and completely dried by a freeze dryer. Column chromatography of the extract on silica gel and sephadex LH-20 yielded in isolation of three main components. Cytotoxic activity was evaluated against the Artemia salina larvae by the Brine Shrimp Cytotoxicity Bioassay. Isolated compounds were identified as alpha-sitosterol [1], salvigenin [5- hydroxy 4', 6, 7- three methoxy flavone] [2] and santoflavon [5- hydroxy 4', 3', 6, 7- tetra methoxy flavone] [3]. NMR data of all the isolated compounds showed good agreement with literature data. In our previous studies ethyl acetate extract of A. talagonica showed cytotoxic activity in brine shrimp lethality assay. The results of BST assay indicated that only santoflavone [3] showed a good cytotoxic activity [LC[50]=15 micro g/ml] against A. salina larvae so this compound seems to be responsible for the extract toxicity of A. talagonica against Artemia nauplii

Isolation and quantificative analysis of oleanolic acid from Satureja mutica fisch and C.A. Mey

Satureja mutica [Lamiaceae] is an herbaceous plant which grows in North- West of Iran. Oleanolic acid has been previously isolated from some Lamiaceae genus and showed a broad range of biological activities. Besides Silphium spp., Panax quinquefolium root and Calendula officinalis flower as the interesting source of oleanolic acid used in the herbal industry, here we report the isolation and quantitative evaluation of oleanolic acid, as one of the major constituents in S. mutica. Dried aerial parts of S. mutica were successively extracted with diethyl ether. This extract was used for further isolation on silica gel column chromatography to obtain compound 1. Isolated compound was identified based on the spectral data of 1H- NMR, [13]CNMR and Mass spectroscopy. Densitometric analysis of the developed plate of TLC was carried out to quantify the oleanolic acid using TLC scanner. Isolated compound [1] was structural elucidated as oleanolic acid and its NMR data showed good agreement with the reference data mentioned in literature. Spectrodensitometric analysis showed that the band characterized by absorption maximum of oleanolic acid was placed at lambda max = 270 nm without derivatization. The contents of oleanolic acid are calculated 17.5 mg in 100 g of S. mutica leaves based on dry weight. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is integral part of the human diet. Densitometric analysis is the accurate, selective, and precise method which can be used for routine quality control analysis and quantitative determination of oleanolic acid in Lamiaceae plants specially Satureja species, as one of the industrial source of this compound

Trypanocidal activity of some medicinal plants against the epimastigotes of Trypanosoma cruzi

Some of medicinal plants are a potential source of new drugs to improve the treatment of Chagase disease whose treatment is still a challenge. Here in this screening, the in vitro trypanocidal activity of some fractions for 16 medicinal plants, collected from the northern part of Iran, has been reported. Aerial parts of the plants were dried carefully and followed by extraction with hexane and methanol, successively, by maceration at room temperature. Different concentrations of the plant extracts in ethanol were investigated against the epimastigotes of T. cruzi. The movement of epimastigotes was observed under a microscope. We assumed that immobilized organisms were died. The negative control contained ethanol in the same proportion utilized to dissolve the drugs. Each assay was performed in duplicate together with gentian violet as a positive control Results show that hexane extracts of Rubus hyrcanus and Salvia sclerae have been observed the most activity against the epimastigotes of T. cruzi [MLC = 12.5 micro g/ml]. None of methanol fractions shows trypanocidal activity except Salvia sclerae [MLC = 50 micro g/ml]. Echium amoenum, Satureja macrantha, S. atropatana and Stachys laxa did not display activity lower than 100 micro g/ml in both hexane and methanol extracts. Some of Iranian medicinal plants [Salvia sclerae, Marrubium vulgare and Rubus hyrcanus] could be the promising source of active components against the epimastigotes of T. cruzi and need to further phytochemical and pharmacological studies

Trypanocidal activity of oil of the young leaves of Nepeta cataria L. obtained by solvent extraction

Trypanocidal activity was found in the volatile oil of the Young leaves of Nepeta cataria L. which has been extracted by diethyl ether and analyzed by GC and GC/MS. Four compounds in the oil of N. cataria, representing 97.53% of the oil were identified. The oil was enriched of monoterpenes with - citral [51.95%] as the major compound. Other main compounds were - citronellol [9.03%], geraniol [4.31%] and nerol [32.24%]. Nepetalactone was not detected in that oil

[Isolation and identification of four sterols from Oud]

The English common name of Aqularia sinensis [Lour.] Gilg. IV. [Thymelaeaceae] is Incense Tree, which is known as Oud in Persian. Aquilaria species produce a resin-deposited part of the trunk. The species was once widely planted in Hong Kong as the raw material of incense exported to China, Southeast Asia and places as far away as Arabia. Investigation of the chemical constituents of the injured or uninjured wood of the plant can offers valuable information in order to know the bioorganic process of resin formation. Methanolic extracts of the uninjured wood of plant was used in order to isolation of sterols components. Separation and purification of the compounds was carried on silica gel column chromatography and gel permeation chromatography [GPC]. Structural elucidation of the constituents was based on the data obtained from H-NMR, 13C-NMR, HMBC, HMQC, DEPT and H-H COSY. Four sterols, stigmast-4-ene-3-one, stigmast-4-ene-3,6-dione, beta-daucosterol and beta-sitosterol were identified based on spectral data which have never been reported from this plant until now. Methanol extract of Aqularia sinensis consists of sterols, of which stigmast-4-ene-3-one, stigmast-4-ene-3, 6-dione, beta-daucosterol and beta-sitosterol [with Stigmastan skeleton] are the main compounds and is reported for the first time

Isolation and identification of Flavonoid constituents from of Achillea conferta DC

Achillea [Asteraceae] comprises 115 species, which are mainly distributed in Europe, Asia and North Africa and also is an introduced plant in the New World. Nineteen species of the genus were described in the Flora Iranica, of which Achillea conferta DC. is found in the central and western regions of Iran as well as Iraq. However, a survey of the literature revealed that only a few works deal with the composition of flavonoid constituents of A. conferta and there is no report on the Iranian one. Here we aim to describe the isolation and identification of flavonoid aglycons in Achillea conferta collected from Talegan mountain in Iran in order to compare with the flavonoid constituents of other samples of A. conferta. The top flowers of Achillea conferta DC. [Compositae] were collected from Taleghan area in spring 2000. The powdered plant was extracted by percolation method with methanol. This crud extract was washed with petroleum ether and chloroform. The resulted extract was concentrated in vacuum distillator and then subjected to paper chromatography [whatman NO: 1], using acetic acid 2%, 15% and BAW as solvents. The spots were detected under UV lamp at 366 nm. Three main flavonoid aglycons were identified as luteolin, chrysoeriol and quercetin by using UV spectra [shift reagents], H- NMR data and Mass spectra in comparison with those reported in references. In this species, highly methoxylated flavonoids could not be observed. Chrysoeriol is the only methoxylated flavon separated from methanol extract of Iranian Achillea conferta

[Phylogenetic analysis of badrashbu species using DNA polymorphism]

The name "badrashbu" has been applied to some species of Dracocephalum [Labiatae] in Iran. Dracocephalum kotschyi is an indigenous herbaceous plant, used in folk medicine as a flavor in Iran. D. subcapitatum grows in both Iran and Turkmenistan. D. arguense is another species of Badrashbu found in Japan. In this study we aimed to examine the phylogenetic relationship between some Dracocephalum species. Randomly amplified polymorphic DNA analysis [RAPD], a molecular biological method, and analysis of volatile extracts [GC] were used. Genetic distances were calculated to construct phylogenetic dendrograms of closely related samples. Based on the results the genetic distance between two samples of D. kotschyi was fond to be short and their RAPD banding patterns were quite similar, also there was a close relationship between two samples of D. arguense. Gas chromatography analysis supported the taxonomic classification. Iranian samples of D. subcapitatum and D. kotschyi contained of limonene- 10- al which could not be detected in Japanese samples of D. arguense. D. subcapitatum show very close relationship to D. kotschyi rather than D. arguense in both phylogenetic and chemotaxonomic aspects