Isolation of potent antileishmanial agents from Artemisia kermanensis Podlech using bioguided fractionation.

Leishmaniasis is a major health problem worldwide with different clinical forms that depend on the parasite, the host's immune system, and immune-inflammatory responses. This study aimed to evaluate the secondary metabolites from Artemisia kermanensis Podlech by bioguided fractionation against Leishmania major. The chemical structures of the isolated compounds were determined based on analysis of mass and nuclear magnetic resonance spectra. Antileishmanial activity were determined on promastigotes and amastigotes. Chemical structures of the isolated compound were as 1-Acetoxy-3,7-dimethyl-7-hydroxy-octa-2E,5E-dien-4-one for compound 1 and 5,7-dihydroxy-3',4',6-trimethoxyflavone (Eupatilin) for compound 2, and 5,7,3'-Trihydroxy-6,4',5'-trimethoxyflavone for compound 3. Compound 2 were confirmed by significant activity with IC50 of less than 50 µg/ml for 24 and 48 h in clinical form (amastigotes). Compound 3 demonstrated high susceptibility with an IC50 of less than 30 µg/ml for promastigotes for 24 h. The bioguided fractionation of A. kermanensis resulted the isolation of potent antileishmanial agents with a low toxicity effect on macrophages. These plant metabolites can be a candidate as a drug for treating cutaneous leishmaniasis.

Diterpenoids from Euphorbia gedrosiaca as Potential Anti-Proliferative Agents against Breast Cancer Cells.

Isolated diterpenes from various species of Euphorbia are important compounds for drug discovery with a broad spectrum of structures and biological effects. In this study, Euphorbia gedrosiaca, one of the endemic species of Iran, was analyzed in terms of the presence and structural determination of diterpenoid compounds. They were extracted with dichloromethane/acetone (2:1) from aerial parts of this plant and purified by chromatographic methods such as MPLC and HPLC. Four premyrsinane compounds and one myrsinane diterpene were isolated from Euphorbia gedrosiaca. They were characterized by extensive 1D and 2D NMR and HRMS analyses. Additionally, their activities were evaluated against two breast cancer cell lines, MDA-MB-231 and MCF-7, by MTT proliferation assay. They exhibited cytotoxic effects in a dose-dependent manner with promising results, which can help to find possible therapeutic application of diterpenoids in breast cancer treatment.

Phytochemical Study of Euphorbia turcomanica Boiss.

The attraction to the Euphorbia genus, with its remarkable diversity in species, is due to its variety of chemical compositions. Euphorbia turcomanica is one of the species of the spurge family growing wildly in Iran. This research aims to investigate the presence of secondary metabolites, specially terpenoid compounds, in terms of structural determination. Samples of E. tucomanica were finely powdered and macerated with acetone/dichloromethane 2:1. Repeated column chromatography using silica gel, MPLC, and HPLC methods followed by the analysis of data obtained from spectroscopic means was carried out to purify and identify the terpenoid constituents. The chemical structures of nine known terpenoids were determined for the first time from E. turcomanica during this study. Loliolide (1), a monoterpene, and eight steroids and triterpenes, including simiarenol (2), isomultiflorenol (3), cycloart-25-ene-3ß,24-diol (4), ß-sitosterol (5), cycloart-23-ene-3ß,25-diol (6), 3α, 11α-dihydroxyurs-12-ene (7), 3ß, 24ß, 25-trihydroxycycloartane (8), and 7α-hydroxystigmasterol (9) were isolated and identified. E. tucomanica, with a rich terpenoid profile, can be one of the valuable and economic sources providing compounds for drug development.

Myrsinane-type diterpenes from Euphorbia gedrosiaca with cell growth inhibitory activity and apoptotic effects on melanoma cancer cells.

Phytochemical analysis of Euphorbia gedrosiaca Rech.f., Aellen & Esfand., an Iranian endemic spurge, afforded the isolation of four myrsinane types diterpene polyesters. Two new compounds (1-2) were based on a myrsinane skeleton while the others (3-4) were known diterpenes based on a cyclomyrsinane backbone. Their chemical structures were elucidated by spectroscopic methods, including 1D and 2D NMR and HRESIMS. The isolated compounds were tested to evaluate their cell growth inhibitory activity and apoptotic effects on melanoma cell lines, B16F10 and A375. The IC50 values for compounds 1-4 were 58.45, 55.43, 86.52 and 82.27 µM, respectively, on B16F10, and 20.66, 21.88, 36.21 and 39.87 µM, respectively, on A375 cells. Non-treated cells were used as negative control (100% cell growth) and 5 nM Taxol were considered as a positive control.

Isolation and Characterization of Methylated Flavones from Artemisia kermanensis.

BACKGROUND: Artemisia kermanensis Podl. is a green aromatic perennial shrub that belongs to the family Asteraceae and it grows widely in central deserts and south-eastern mountains of Iran such as Taftan Mountain in Sistan and Baluchestan Province. Artemisia species have been used traditionally as a remedy for various feverous diseases, including malaria, treatment of colds, infections, parasites, inflammations of the liver, as well as dyspepsia, diabetes, hypertension, and so many other conditions. MATERIALS AND METHODS: Air-dried A. kermanensis extraction from all parts of the plant was done using different organic solvents. The methanolic extract was selected for isolation of flavonoids, using thin-layer chromatography. The chemical structures of the isolated compounds were determined based on analysis of mass and nuclear magnetic resonance spectra. RESULTS: Two flavone aglycones were isolated and identified for the first time from this plant's methanolic extract, including 5,7-dihydroxy-3',4',6-trimethoxyflavone (eupatilin) and 5,7,3'-Trihydroxy-6,4',5'-trimethoxyflavone. CONCLUSIONS: Eupatilin is known for its anticancer, antioxidant, and anti-inflammatory activities. In future researches on A. kermanensis, as a rich source of these flavone compounds, it is wise to investigate for the proven eupatilin's biological activities that have been mentioned.

Cinnamic acid derivatives from welsh onion (Allium fistulosum) and their antibacterial and cytotoxic activities.

INTRODUCTION: Cinnamic acids are a class of compounds based on phenyl propanoid backbone (C6-C3) isolated from plants and microorganisms, exhibiting interesting biological activities. OBJECTIVE: To characterise cinnamic acids through the phytochemical study of welsh onion, Allium fistulosum, and to evaluate their antibacterial and cytotoxic properties. MATERIAL AND METHODS: The phytochemical study of A. fistulosum was performed through chromatographic techniques, including reversed phase medium-pressure liquid chromatography (MPLC) and high-pressure liquid chromatography (HPLC). Preliminary analysis of crude chromatographic fractions from the organic extracts was carried out by proton nuclear magnetic resonance (1 H-NMR) in order to prioritise the study of those having phenyl propanoid skeleton. The structural identification of the isolated compounds was performed through analysis of spectroscopic data, mainly one-dimensional (1D) and two-dimensional (2D) NMR. The antibacterial activity was assessed against gram negative (Escherichia coli) and gram positive (Staphylococcus aureus) bacteria while the cytotoxic property was evaluated on breast cancer cell line (MCF-7). RESULTS: The 1 H-NMR study of crude fractions and application of a straightforward method to purify the phenyl propanoid compounds by reversed phase MPLC and HPLC, allowed the effortless isolation of several cinnamic acids, including two new rare phenolic imidates (1 and 2). The use of an entirely NMR approach for structural elucidation of the isolated metabolites allowed the isolated material to be kept for further pharmacological tests. CONCLUSION: These results corroborate the importance of the use of 1D and 2D NMR to the identification of new phenyl propanoids, potential lead compounds against bacteria and cancer cells.

Furostanol Saponins from the Bulbs of Welsh Onion, Allium fistulosum L.

An extensive phytochemical analysis of the polar extracts from bulbs of Welsh onion Allium fistulosum L. led to the isolation of nine saponins, four of them, named fistulosaponins G (1a/1b), H (2), I (3a/3b), and J (4), have never been reported previously. Fistulosaponins G and I were isolated as a couple of isomers in equilibrium. On the basis of 2D NMR and mass spectrometry data, the structure of the novel compounds were elucidated as (25R)-26-[(ß-D-glucopyranosyl)oxy]-3ß,22ß-dihydroxyfurost-5-en-1ß-yl O-α-L-rhamnopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranoside (1a) with its 22α epimer (1b), (25R)-26-[(ß-D-glucopyranosyl)oxy]-3ß-hydroxyfurost-5,20-dien-1ß-yl O-α-L-rhamnopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranoside (2), (25R)-26-[(ß-D-glucopyranosyl)oxy]-3ß,22ß-dihydroxyfurost-5-en-1ß-yl O-α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranoside (3a) with its 22α epimer (3b), and (25R)-26-[(ß-D-glucopyranosyl)oxy]-3ß-hydroxyfurost-5,20-dien-1ß-yl O-α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranoside (4). This is the first report of furostanol saponins in A. fistulosum bulbs. In addition, data on the antibacterial tests of the isolated saponins against Escherichia coli and Enterococcus faecalis are reported.

Obtusifoliol related steroids from Euphorbia sogdiana with cell growth inhibitory activity and apoptotic effects on breast cancer cells (MCF-7 and MDA-MB231).

From the aerial parts of Euphorbia sogdiana Popov, obtusifoliol (1) and two related steroids (2-3) have been isolated and characterized along with a known cycloartane derivative (4). The chemical structure of the obtusifoliol-related compounds, obtained by 1D and 2D NMR, and MS measurements, have been determined as: 3ß,7α-dihydroxy-4α,14α-dimethyl-5α-ergosta-8,24(28)-diene-11-one (2) and 3ß-hydroxy-4α,14α-dimethyl-5α-ergosta-8,24(28)-diene-1-one (3). Compound 2 has been previously isolated from Euphorbia chamaesyce while compound 3 was never reported before. The isolated compounds 1-4 were subjected to cytotoxic tests on the breast cancer cells, MCF-7 and MDA-MB231. Further pharmacological tests on the more active compounds 2 and 3 indicated their action to be related to cell growth inhibitory activity and apoptotic effects on the tested cells.

6(17)-Epoxylathyrane diterpenes from Euphorbia sogdiana Popov with cytotoxic activity.

Phytochemical analysis of Euphorbia sogdiana Popov, Euphorbiaceae, afforded the isolation of three new diterpenes based on the rare 6(17)-epoxylathyrane skeleton (1-3), along with a lathyrane (4), a myrsinane (5) and a tigliane (6) diterpenoids, previously isolated from Euphorbia aellenii. Their chemical structures were established through a combination of nuclear magnetic resonance spectroscopy and mass spectrometric methods. The epoxylathyranes 1-4 were tested to evaluate their cytotoxic activity against Jurkat T-leukemia and EJ-138 bladder cancer cells and their chemical analogy allowed to propose some structure activity relationships.