New coumarin glycosides from endemic Prangos heyniae H. Duman & M.F. Watson.

Two new coumarin glycosides, named 7-methoxy isoarnottinin 4'-O-ß-ᴅ-glucopyranoside and 7-methoxy isoarnottinin 4'-O-rutinoside (1 and 2) along with six known compounds (3-8) were isolated from the roots of Prangos heyniae, an endemic plant of Turkey. 1-methylethyl 6-O-D-apio-ß-ᴅ-furanosyl-ß-ᴅ-glucopyranoside (7) and cnidioside A (8) have been obtained from the genus Prangos for the first time. Structures of isolated compounds were established using spectroscopic methods (1 D and 2 D NMR, HR-MS, UV and IR). Moreover, all extracts and isolated compounds were evaluated for their cytotoxic activity against NIH/3T3, HK-2, A-549, MCF-7, PC-3 and SH-SY5Y cell lines by WST-1 method. One of the new coumarin glycosides, 7-methoxy isoarnottinin 4'-O-ß-ᴅ-glucopyranoside (1) exhibited selective cytotoxic activity against SH-SY5Y cells with IC50 value of 31.41 ± 1.04 µM.

Investigation of microwave extraction of red cabbage and its neurotherapeutic potential.

In the pursuit of bioactive compounds with health benefits from food and medicinal plants, optimization of process to reduce solvent, raw material, energy and time consumption has been a valuable research objective. Sustainable management and efficient use of natural resources are of critical importance for sustainability goals. In this manner, microwave extraction of red cabbage which has been a mass cultivated plant for food purposes, was optimized for maximizing acetylcholinesterase, butyrylcholinesterase, tyrosinase inhibitory activity and bioactive content. Quantitative analysis of total phenol, flavonoid and anthocyanin content were performed using spectrophotometry and UPLC-DAD-ESI-MS/MS. Optimum conditions were determined as 600 W, 100% ethanol, 12 min for butyrylcholinesterase inhibitory and 800 W, 50% ethanol, 4 min for tyrosinase inhibitory activity. Microwave extraction outperformed conventional solvent extracts (hexane, dichloromethane, 2-methyl tetrahydrofuran, ethanol, 70% ethanol and water) in terms of activity and content. The isolated fraction containing major anthocyanins as cyanidin-3-sophoroside-5-glucoside and cyanidin-3-(sinapoyl)-sophoroside-5-glucoside was identified as the responsible portion for tyrosinase inhibitory activity. The dominant anthocyanins rich fraction of the optimum microwave extract can be considered for the production of antityrosinase products, while the identification of inhibitor metabolites for acetylcholinesterase and butyrylcholinesterase can be targeted for future studies considering red cabbage as a valuable source.

Anticholinesterase Compounds from Endemic Prangos uechtritzii.

In this study, the anticholinesterase effects of the extracts and isolated compounds from the roots of endemic Prangos uechtritzii Boiss & Hausskn (Apiaceae) are reported. A novel polyacetylenic compound; (+)-8-O-methyloplopantriol A along with two known polyacetylenes; (-)-panaxynol, (+)-falcarindiol and fifteen known coumarin derivatives; umbelliferone, 6-formylumbelliferone, suberosin, 7-demethylsuberosin, (+)-ulopterol, tamarin, psoralen, imperatorin, (+)-oxypeucedanin, (+)-oxypeucedanin hydrate, (+)-oxypeucedanin methanolate, (+)-marmesin, (-)-prantschimgin, (+)-decursinol, and (-)-adicardin were isolated from the hexane (Pu-HE), chloroform (Pu-CE), and methanol (Pu-ME) extracts of P. uechtritzii roots. (-)-Panaxynol, (+)-falcarindiol, 6-formylumbelliferone, (+)-decursinol, and (-)-adicardin were obtained from the genus Prangos for the first time. (+)-8-O-Methyloplopantriol A inhibited both AChE (IC50 =194.5±5.8 µM) and BChE (IC50 =51.9±2.96 µM) enzymes. (+)-Falcarindiol, 6-formylumbelliferone, 7-demethylsuberosin, tamarin, and imperatorin also exhibited BChE-specific inhibitory activities (IC50 =27.88-93.86 µM). (+)-Falcarindiol (IC50 =27.88±0.91 µM) and imperatorin (IC50 =30.89±1.40 µM) as the most active components could be led compounds to develop new BChE inhibitors with further research against Alzheimer's disease.

Comparative evaluation of relaxant effects of three prangos species on mouse corpus cavernosum: Chemical characterization and the relaxant mechanisms of action of P. pabularia and (+)-oxypeucedanin.

ETHNOPHARMACOLOGICAL RELEVANCE: Erectile dysfunction (ED) is the most common form of sexual dysfunction which has been the topic of great interest through the history by all cultures. It is now among the most treated health problems in men of all ages that develop under the influence of lifestyle factors and some diseases. Plants are extensively used to cure sexual dysfunction for centuries. Roots of Prangos sp. have been used to improve sexual performance in Anatolian traditional medicine and are rich of coumarin, furanocoumarin and their derivatives. Scientific research is necessary to support and validate the ethno-traditional uses of these plants. AIM OF THE STUDY: The aim of this study is to investigate the effects of the root extracts of P. pabularia, P. uechtritzii and P. heyniae on erectile function and to isolate and identify the chemical compounds of the most active extract and reveal possible pharmacological mechanism of the major compound of the extract with the strongest relaxant effect in mouse corpus cavernosum (MCC). MATERIALS AND METHODS: The roots of plants were extracted with chloroform, n-hexane and methanol. The compounds were isolated from the extract by column chromatography and structures were identified by NMR and MS. The relaxant effects of extracts (10-7-10-4 g/mL), (+)-oxypeucedanin (10-7-10-4 M) and Na2S (10-7-3 × 10-3 M) were tested in MCC strips by DMT myograph. To investigate the mechanism, the synthesis inhibitors of aminooxyacetic acid (AOAA, 10-2 M) and nitro-L-arginine methyl ester (L-NAME, 10-4 M) were used, respectively. H2S formation was evaluated basal and L-cysteine (L-cyst)-stimulated conditions by H2S microsensor. RESULTS: All extracts relaxed MCC in a concentration dependent manner. The maximum relaxing effects were achieved with chloroform extracts. Chloroform extract of P. pabularia (Pp-CE) was more potent than the others. Pp-CE-induced relaxations were significantly decreased by AOAA and L-NAME. (+)-Oxypeucedanin, the major compound of Pp-CE, induced relaxant responses and this effect was inhibited by AOAA, but not L-NAME. The relaxation of (+)-oxypeucedanin was found to be similar in view of Emax to positive control H2S donor Na2S. (+)-Oxypeucedanin increased L-cyst-stimulated H2S formation. Augmentation of H2S synthesis with (+)-oxypeucedanin was inhibited by AOAA. CONCLUSIONS: Pp-CE has the strongest effect on relaxation of MCC and this result supports the traditional aphrodisiac use of P. pabularia root extract in Anatolia. The pharmacological mechanisms of Pp-CE to relax MCC involve NO and H2S formation. (+)-Oxypeucedanin could be responsible for the H2S-mediated relaxations of Pp-CE in MCC.

Optimization of microwave assisted extraction of Morus nigra L. fruits maximizing tyrosinase inhibitory activity with isolation of bioactive constituents.

Morus nigra L. is a beneficial food due to rich phenolic components. While aiming higher yields for bioactive constituents, reduction in terms of raw material, solvent, time and energy gained more importance to provide a sustainable life for human and nature. Microwave assisted extraction (MAE) of Morus nigra fruits was optimized in order to elicit process parameters maximizing bioactive metabolites and tyrosinase inhibitory activity. Spectrophotometry and UPLC-DAD-ESI-MS/MS systems were utilized for quantitative analysis of total phenol, flavonoid and anthocyanin contents. Optimum conditions for MAE were determined as 500 W, 35% ethanol, 10 min yielding 12.63 mg/g cya-3-glu equiv. anthocyanin and IC50 value of 1.60 mg/ml for tyrosinase inhibitory activity. Microwave extracts prevailed better outcomes compared to conventional extraction methods (10.93 mg/g content with IC50 of 2.81 mg/ml). MAE could be considered as an advanced technique to obtain extracts from Morus nigra fruits with higher bioactive content and activity.

Specialized metabolites from the aerial parts of Centaurea polyclada DC.

The genus Centaurea L. (Asteraceae) is represented by 200 taxa in the flora of Turkey and several Centaurea species are used as herbal remedies against different conditions. Previous phytochemical investigations on this genus generally revealed the isolation of sesquiterpene lactones and flavonoid derivatives. In our continuous search on Centaurea genus, a phytochemical study was performed on Centaurea polyclada DC., an endemic of West Anatolia. Previously undescribed two sesquiterpene-amino acid conjugates, an elemane and an eudesmane derivative were isolated from the aerial parts of Centaurea polyclada, together with eight known compounds; two elemane derivatives, three flavonoids, a lignan, a phenolic glucoside and a phenylpropanoid glucoside. Structural elucidation of the compounds was based on spectroscopic evidence, including 1D and 2D NMR and high-resolution mass spectrometry, chemical degradation results and reference data comparison. Sesquiterpene-amino acid conjugates are representatives of an unusual group of sesquiterpenes, and elemane-amino acid conjugates are herein reported for the first time in nature.

Bioactivity screening of five Centaurea species and in vivo anti-inflammatory activity of C. athoa.

CONTEXT: Centaurea L. (Asteraceae) species used as herbal remedies in Turkish traditional medicine have shown several biological properties. OBJECTIVE: Extracts obtained from the aerial parts of Centaurea aphrodisea Boiss., Centaurea athoa DC., Centaurea hyalolepis Boiss., Centaurea iberica Trev. and Centaurea polyclada DC. were evaluated for their antioxidant, cytotoxic and anti-inflammatory activities. MATERIALS AND METHODS: Extracts of Centaurea species were tested for their antioxidant activity in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS) screening assays and for in vitro anti-inflammatory activity by Nf-κB and iNOS inhibition assays. The extracts were tested for their in vitro cytotoxicities against a panel of human solid tumor cell lines (SK-MEL: malignant melanoma, KB: oral epidermal carcinoma, BT-549: breast ductal carcinoma and SK-OV-3: ovary carcinoma) as well as non-cancerous kidney fibroblast (Vero) and kidney epithelial cells (LLC-PK1) by Neutral Red assay. In vivo anti-inflammatory activity of C. athoa was evaluated by the carrageenan-induced paw edema test in rats. RESULTS: Antioxidant activities were observed for methanol extracts of plants. C. polyclada had the strongest effect on BT-549, KB and SK-OV-3 cell lines (30, 33 and 47 µg/ml, respectively). Nf-κB inhibition of chloroform extract of C. athoa was determined equivalent to positive control parthenolide (IC50: 6 µg/ml). This extract also showed anti-inflammatory activity by the carrageenan-induced paw edema test in rats, in all hours at a dose of 50 mg/kg compared to the control group. DISCUSSION AND CONCLUSION: C. athoa is suggested to be a potential source of lead compounds for inflammatory diseases due to the significant in vitro and in vivo anti-inflammatory results.