Dihydroisocoumarins and Phenylglycosides from Scorzonera longiana, Their Antimicrobial Activities and Molecular Docking Studies.

Five new phenyl dihydroisocoumarin glycosides (1-5) and two known compounds (6-7) were identified from the butanol fraction of Scorzonera longiana. The structures of 1-7 were elucidated based on spectroscopic methods. Antimicrobial, antitubercular, and antifungal evaluation of compounds 1-7 were carried out using the microdilution method against nine microorganisms. Compound 1 was active only against Mycobacterium smegmatis (Ms) with a MIC value of 14.84 µg/mL. All tested compounds (1-7) were active against Ms but only compounds 3-7 were active against fungi (C. albicans, S. cerevisiae) with MIC values of 25.0-125 µg/mL. In addition, molecular docking studies were conducted against Ms DprE1 (PDB ID: 4F4Q), Mycobacterium tuberculosis (Mbt) DprE1 (PDB ID: 6HEZ), and arabinosyltransferase C (EmbC, PDB ID: 7BVE) enzymes. Compounds 2, 5, and 7 are the most effective Ms 4F4Q inhibitors. Compound 4 was the most promising inhibitory activity on Mbt DprE with the lowest binding energy of -9,9 kcal/mol.

Two new dihydroisocoumarins and terpenoids from Scorzonera longiana Sümbül an endemic species to Turkey and their antimicrobial activity.

Two new dihydroisocoumarins (scorzolongin I (1), and scorzolongin II (2)) and nine known compounds (3',5'-dimethoxy hydrangenol (scorzolongin III, 3), cladantholide (4), dammar-24-ene-3ß-ol (5), taraxasterol (6), ß-sitosterol (7), mangifgerursanone (8), and a mixture of α-amyrenone (9a), ß-amyrenone (9b), and dammar-24-ene-3-one (9c) in about 1:1:2 ratio) were identified from the dichloromethane fraction of Scorzonera longiana. The structure of all compounds (1-9a-c) were elucidated by extensive 1D and 2D NMR (1H, 13C/APT, COSY, HMBC, HSQC, and NOESY) spectroscopy, UV, FT-IR, and LC-QTOF-MS data and by comparison of their NMR data with the literature. These compounds have been isolated from S. longiana for the first time. An antimicrobial assay against eight microorganisms was applied to isolated compounds 1-3. Scorzolongin I, and scorzolongin II, and scorzolongin III showed notable activity against gram (-) (Escherichia coli and Yersinia pseudotuberculosis) and fungi (Candida albicans, Saccharomyces cerevisiae) with 20 mm inhibition zone each. Scorzolongin II (2) exhibited strong activity against E. coli, Y. pseudotuberculosis, Mycobacterium smegmatis C. albicans, S. cerevisiae with MIC value of 33.8 µg/mL.

Assessment of Correlation Analysis, Phytochemical Profile, and Biological Activities of Endemic Scorzonera Species from Turkey.

Scorzonera species belong to the Asteraceae family comprising more than 25000 species. The present study aimed to examine the phytochemical profiles and biological activities of S. sandrasica Hartvig et Strid, S. coriacea A. Duran&Aksoy, and S. ahmet-duranii Makbul&Coskuncelebi which are endemic species to Turkey. Flavonoids such as hyperoside, isoquercitrin, rutin, isoorientin, orientin, 7-O-methyl isoorientin, luteolin-7-O-ß-glycoside, apigenin-7-O-ß-glucoside, vitexin, isovitexin as well as caffeoylquinic acid derivatives including chlorogenic acid, 4,5-O-dicaffeoylquinic acid, and 1,5-O-dicaffeoylquinic acid contents were analyzed to clarify phytochemical content of the extracts. Aerial parts of the investigated extracts were determined as contain flavonoids in high amounts. Chlorogenic acid and its derivatives were detected in all investigated species, in varying amounts, both in the roots and aerial parts. S. coriacea aerial parts contained the highest total phenolic and flavonoids. The strongest inhibitory activities on ABTS and DPPH radicals were also observed with S. coriacea aerial parts by 8.07±0.28 and 13.94±0.53 µg/ml of IC50 values, respectively. Total phenolic contents of the extracts were significantly correlated with DPPH (r=-0.9842, p=0.0004) and ABTS free radical scavenging (r=-0.9870, p=0.0003) and total antioxidant capacity (r=0.8173, p=0.0470), as well as total flavonoid contents (r=0.8820, p=0.0201). S. sandrasica aerial parts and S. ahmet-duranii roots exhibited the greatest red blood cell membrane protection and protein denaturation inhibition, respectively. From the phytochemical point of view, all the selected species were analyzed for the first time.

Phytochemical Composition and Biological Activities of Scorzonera Species.

The genus Scorzonera comprises nearly 200 species, naturally occurring in Europe, Asia, and northern parts of Africa. Plants belonging to the Scorzonera genus have been a significant part of folk medicine in Asia, especially China, Mongolia, and Turkey for centuries. Therefore, they have become the subject of research regarding their phytochemical composition and biological activity. The aim of this review is to present and assess the phytochemical composition, and bioactive potential of species within the genus Scorzonera. Studies have shown the presence of many bioactive compounds like triterpenoids, sesquiterpenoids, flavonoids, or caffeic acid and quinic acid derivatives in extracts obtained from aerial and subaerial parts of the plants. The antioxidant and cytotoxic properties have been evaluated, together with the mechanism of anti-inflammatory, analgesic, and hepatoprotective activity. Scorzonera species have also been investigated for their activity against several bacteria and fungi strains. Despite mild cytotoxicity against cancer cell lines in vitro, the bioactive properties in wound healing therapy and the treatment of microbial infections might, in perspective, be the starting point for the research on Scorzonera species as active agents in medical products designed for miscellaneous skin conditions.

Hypolipidemic, Antioxidant and Cardioprotective Effects of the Aqueous Extract from Scorzanera Undulata Tubers in Streptozotocin-Induced Diabetic Rats.

AIMS: This study aimed to assess the effect of Scorzanera undulata on plasma lipid profile. BACKGROUND: Scorzanera undulata (S. undulata) is a medicinal plant popularly used in the Moroccan pharmacopeia as traditional medicine, particularly to treat diabetes mellitus. OBJECTIVE: The purpose of this study was to explore the effects of aqueous extract of Scorzanera undulata tubers (AERSU) on lipid profile and atherogenic indices in Wistar rats. Biochemical parameters such as Total Cholesterol (TC), triglycerides (TG), and low-and high-density lipoproteins-cholesterol (LDL and HDL) were assessed. Furthermore, the in vitro antioxidant activity of AERSU was also evaluated. METHODS: The effect of tubers aqueous extract (AERSU) of S. undulata (20 mg/kg) on plasma lipid profile was investigated in normal and streptozotocin (STZ)-induced diabetic rats. The aqueous extract was tested for its in vitro antioxidant activity. Besides, cardiovascular parameters were estimated. RESULTS: Treatment with AERSU significantly improved the weight in diabetic rats and decreased plasma cholesterol, triglycerides, and LDL lipoproteins levels. Furthermore, the extract had a favorable impact on the Atherogenic Index (AI) and Coronary Risk Index (CRI). In addition, AERSU seems to possess a potent in vitro antioxidant activity. CONCLUSION: The study demonstrates that aqueous Scorzanera undulate extract exhibits antidyslipidemic and antioxidant activities.

Antihyperglycemic Activity and Safety Assessment of the Aqueous Extract of Aerial Parts of Scorzonera undulata ssp deliciosa in Rat.

AIMS: The aim of this study was to evaluate the antidiabetic effect of Scorzonera undulata. BACKGROUND: Scorzonera undulata ssp deliciosa, locally known as "Guiz", is used as a phytomedicine in Morocco and Algeria to treat different health problems. Interestingly, it is used in the Moroccan pharmacopeia to treat diabetes. To our knowledge, this medicinal herb has never been investigated for any pharmacological activity. OBJECTIVE: This study aimed to evaluate the antihyperglycemic effect of the aqueous extract of the aerial part of Scorzonera undulata (SUAP) in normal and STZ-induced diabetic rats and to assess the acute toxicity of this extract in Wistar rats. METHODS: This study investigated the effects of SUAP at a dose of 20 mg/kg on blood glucose levels in normal and streptozotocin(STZ)-induced diabetic rats. The acute toxicity of SUAP was examined according to the OECD test guideline; rats were divided into four groups of each sex and orally received the SUAP (1000, 2000, or 3000 mg/kg BW). Post-treatment, body weight, signs of toxicity, and/or mortality were observed during 14 days. Other assays such as histopathological examination, preliminary phytochemical investigation, determination of glycogen content and evaluation of α-amylase were performed according to standard protocols. RESULTS: The findings of the current study depicted that both single and repeated oral administration of SUAP (20 mg/kg) generated a significant fall in the blood glucose levels in diabetic rats. A single oral administration of SUAP (at the highest dose of 3000 mg/kg BW) had no significant acute toxicological effects, and oral LD50 of SUAP was greater than 3000 mg/kg. Furthermore, repeated oral administration of SUAP during 15 days led to an increase in the liver glycogen content in diabetic rats to improve the histopathological structure of the liver and pancreas in SUAPtreated diabetic rats and to ameliorate some biochemical parameters such as ALT and creatinine. SUAP had no effect on α-amylase activity. In addition, the preliminary phytochemical investigation showed the richness of the roots of SUAP in some phytochemicals, particularly the polyphenols. CONCLUSION: The present study demonstrates the antihyperglycemic effect of Scorzonera undulata in diabetic rats which could be involved through the improvement of liver structure and function. In addition, the dose used is not toxic. Finally, the extract contains large amounts of bioactive compounds, mainly polyphenols.

Antibacterial and antibiofilm activities of Scorzonera mackmeliana.

Scorzonera have been confirmed to have potent bioactivity. Scorzonera mackmeliana (Asteraceae), the endemic plant to Lebanon, has not yet been investigated. In the present study, we assessed the antibacterial activity of S. mackmeliana extracts against referenced bacterial strains. Extracts from different parts of the plant were evaluated against Staphylococcus, Enterococcus, Escherichia and Pseudomonas species. Phytochemical screening was done by standard biochemical tests and minimal inhibitory concentration (MIC), minimal bactericidal concentration (MBC) and minimal biofilm eradication concentration (MBEC) were determined by micro dilution method. The extracts possessed mainly alkaloids, phenols, flavonoids and coumarins. Gram-negative bacteria were most sensitive, whose MICs ranged between 48.98 and 341.85 mg/ml. Water stems extract, rich in phenols, was the most active with an MIC of 48.98 mg/ml. MBC was only recorded for water flowers extract, rich in resins, against P. aeruginosa and ethanolic roots extract, rich in terpenoids, against S. epidermidis with values of 160.85 mg/ml and 284.35 mg/ml, respectively. Furthermore, antibiofilm activity showed that the lowest MBEC was 0.1 mg/ml for water stems extract with an eradication ability of 91% (p <0.0001). Hence, this study suggests S. mackmeliana as a promising candidate for future investigations to elucidate the major bioactive compound behind the antibacterial and antibiofilm effect.

Two new phenolic compounds and some biological activities of Scorzonera pygmaea Sibth. & Sm. subaerial parts.

Phytochemical composition of ethyl acetate fraction and total phenolic content, in vitro antioxidant, anti-inflammatory, antimicrobial activities of petroleum ether, chloroform, ethyl acetate and n-butanol fractions of the ethanol extract obtained from the subaerial parts of Scorzonera pygmaea Sibth. & Sm. (Asteraceae) were investigated. Nine compounds; scorzopygmaecoside (1), scorzonerol (2), cudrabibenzyl A (3), thunberginol C (4), scorzocreticoside I (5) and II (6), chlorogenic acid (7), chlorogenic acid methyl ester (8), 3,5-di-O-caffeoylquinic acid (9) were isolated and identified using spectroscopic methods. All substances were isolated for the first time from this species. Compounds 1 and 2 are new. The fractions showed high antioxidant capacity correlated with their phenolic content and no significant antimicrobial activity against tested bacteria and fungi. COX inhibition test was used to evaluate the anti-inflammatory activity and all the fractions showed low inhibition in comparison with indomethacin.

Inhibitory activity of Podospermum canum and its active components on collagenase, elastase and hyaluronidase enzymes.

Present study is aimed to investigate in vitro inhibitory effects of the extract prepared from the aerial parts of Podospermum canum (syn: Scorzonera cana var. jacquiniana) (Asteraceae) on hyaluronidase, collagenase, and elastase enzymes using a bioassay-guided fractionation. Inhibitory effects of the extract, sub-extracts, fractions obtained by column chromatography, and isolated compounds on collagenase, elastase, and hyaluronidase were performed by using in vitro enzyme inhibitory assays based on spectrophotometric evaluation. The methanolic extract obtained from P. canum exhibited strong inhibitory activities on elastase and collagenase while the insignificant activity was observed on hyaluronidase. Through bioactivity-guided fractionation, the ethyl acetate and remaining water sub-extracts obtained from the methanolic extract displayed significant inhibitory activities on collagenase and elastase, while petroleum ether and chloroform extracts did not show any inhibitory activity. Eleven known compounds: arbutin, 6́-O-caffeoylarbutin, cichoriin, 3,5-dicaffeoylquinic acid methyl ester, apigenin 7-O-ß-glucoside, luteolin 7-O-ß-glucoside, apigenin 7-O-ß-rutinoside, isoorientin, orientin, vitexin, procatechuic acid, and new compound 4-hydroxy-benzoic acid 4-(6-O-α-rhamnopyranosyl-ß-glucopyranosyl) benzyl ester have been obtained from ethyl acetate sub-extract. Results of the present study have revealed that apigenin 7-O-ß-glucoside, luteolin 7-O-ß-glucoside, apigenin 7-O-ß-rutinoside, and isoorientin showed potent enzyme inhibitory activities. However, methanolic extract of P. canum displayed a greater inhibitory activity than fractions and isolated compounds both on collagenase and elastase.

Phytochemical Analysis of Podospermum and Scorzonera n-Hexane Extracts and the HPLC Quantitation of Triterpenes.

Previously tested n-hexane extracts of the Scorzonera latifolia showed promising bioactivity in vivo. Because triterpenes could account for this activity, n-hexane extracts were analyzed by HPLC to identify and quantify the triterpenes as the most abundant constituents. Other Scorzonera and Podospermum species, potentially containing triterpenic aglycones, were included in the study. An HPLC method for simultaneous determination of triterpene aglycones was therefore developed for analysis of Podospermum and Scorzonera species. n-Hexane extracts of root and aerial parts of S. latifolia, ten other Scorzonera species and two Podospermum species were studied to compare the content of triterpenes. HPLC was used for the qualitative and quantitative analysis of α-amyrin, lupeol, lupeol acetate, taraxasteryl acetate, 3-ß-hydroxy-fern-7-en-6-one acetate, urs-12-en-11-one-3-acetyl, 3-ß-hydroxy-fern-8-en-7-one acetate, and olean-12-en-11-one-3-acetyl. Limits of detection and quantification were determined for each compound. HPLC fingerprinting of n-hexane extracts of Podospermum and Scorzonera species revealed relatively large amounts of triterpenes in a majority of investigated taxa. Lupeol, lupeol acetate, and taraxasteryl acetate were found in a majority of the species, except S. acuminata. The presence of α-amyrin, 3ß-hydroxy-fern-7-en-6-one-acetate, urs-12-en-11-one-3-acetyl, 3ß-hydroxy-fern-8-en-7-one-acetate, and olean-12-en-11-one-3-acetyl was detected in varying amounts. The triterpene content could correlate with the analgesic and anti-inflammatory activity of Scorzonera, which was previously observed and Scorzonera species that have been determined to contain triterpenes in large amounts and have not yet been tested for their analgesic activity should be tested for their potential analgesic and anti-inflammatory potential. The presented HPLC method can be used for analysis of triterpene aglycones, for example dedicated to chemosystematic studies of the Scorzonerinae.

Two novel bioactive sulfated guaiane sesquiterpenoid salt alkaloids from the aerial parts of Scorzonera divaricata.

Extracts of the aerial parts of Scorzonera divaricata afforded sulfoscorzonin D (1) and sulfoscorzonin E (2), two novel pyrrolidine inner salt alkaloids with a sulfated guaiane sesquiterpene lactone nucleus, along with 22 known compounds. Especially, sulfoscorzonin D containing a unusual monoterpene moiety is very rare. The structures of new compounds were established using spectroscopic analysis including one- and two-dimensional NMR and HRESIMS. The cytotoxicities of compounds 1-4 and 10 against three tumor cell lines (K562, Hela, and HepG2) were evaluated using the MTT assay. Compounds 2 and 10 exhibited moderate cytotoxic activity. The biological properties of 1-3, 5-8, 10-14, and 16-24, were screened against nine different gram-positive and gram-negative bacteria. Compounds 1, 5-8, 10, and 18, showed potent antibacterial activities. CHEMICAL COMPOUNDS STUDIED IN THIS ARTICLE: Glucozaluzanin C (PubChem CID: 442320); 1ß,4α-dihydroxy-5α,6ß,7α,11ßH-eudermn-12; 6-olide (CID: 11119093); oleanolic acid (CID: 10494); lup-20(29)-ene-3ß,28-diol (CID: 72326); (22E)-5α,8α-epidioxyergosta-6,22-dien-3ß-ol (CID: 5469431); ergosta-3ß,5α, 6ß-trialcohol (CID: 44558918); stigma-5-en-3-O-ß-glucoside (CID: 5742590); vomifoliol (CID: 12444927); trans-caffeic acid (CID: 689043); trans-p-hydroxy coumaric acid (CID: 637542); 4-hydroxy-3-methoxyphenyl ferulate (CID: 11500646); 7,3',4'-trihydroxyflavonol (CID: 5281614); tricin (ID: 5281702); luteolin (CID: 5280445); diosmetin (CID: 5281612); 5,7-dihydroxy-8-methoxyflavone (CID: 5281703); 5,7-dihydroxy-6-methoxyflavone (CID: 5320315); methyl-3,4-dihydroxy benzoate (CID: 287064); m-hydroxy benzoic acid (CID: 7420); 7-hydroxy-coumarin (CID: 5281426); and scopoletin (CID: 5280460).

Flavonoid Glycosides and Their Derivatives from the Herbs of Scorzonera austriaca Wild.

Five flavonoid glycosides and two derivatives were isolated from the herbs of Scorzonera austriaca Wild by silica gel column chromatography and preparative HPLC. Their structures were identified, using chemical and spectroscopic methods, as 5,7,4'-trihydroxyflavone 6-C-(2''-O-ß-d-glucopyranosyl ß-d-glucopyranoside) (1), 5,7,3',4'-tetrahydroxyflavone 6-C-(2''-O-ß-d-glucopyranosyl ß-d-glucopyranoside) (2), quercetin 3-O-rutinoside (3), 5,7,4'-trihydroxyflavone 6-C-ß-d-glucopyranoside (4), 3'-methoxy-5,7,4'-trihydroxyflavone 6-C-ß-d-glucopyranoside (5), 5,7,4'-trihydroxyflavone 8-C-(6''-O-trans-caffeoyl ß-d-glucopyranoside) (6), and 5,7,3',4'-tetrahydroxyflavone 8-C-(6''-O-trans-caffeoyl ß-d-glucopyranoside) (7). Compounds 6 and 7 are new flavonoid glycoside derivatives, and compounds 1-5 were isolated from the herbs of Scorzonera austriaca for the first time. Compounds 6 and 7 were also assayed for their hepatoprotective activities with rat hepatocytes in vitro.

Preparative Separation and Purification of the Total Flavonoids in Scorzonera austriaca with Macroporous Resins.

The use of macroporous resins for the separation and purification of total flavonoids to obtain high-purity total flavonoids from Scorzonera austriaca was studied. The optimal conditions for separation and purification of total flavonoids in S. austriaca with macroporous resins were as follows: D4020 resin columns were loaded with crude flavonoid extract solution, and after reaching adsorptive saturation, the columns were eluted successively with 5 bed volumes (BV) of water, 5 BV of 5% (v/v) aqueous ethanol and 5 BV of 30% (v/v) aqueous ethanol at an elute flow rate of 2 BV·h(-1). Total flavonoids were obtained from the 30% aqueous ethanol eluate by vacuum distillation recovery. The content of flavonoid compounds in the total flavonoids was 93.5%, which represents an improvement by about 150%. In addition, five flavonoid compounds in the product were identified as 2″-O-ß-d-xylopyranosyl isoorientin, 6-C-α-l-arabipyranosyl orientin, orientin, isoorientin and vitexin by LC-ESI-MS analysis and internal standard methods. The results in this study could represent a method for the large-scale production of total flavonoids from S. austriaca.

Sesquiterpenoids and tirucallane triterpenoids from the roots of Scorzonera divaricata.

A sulfated guaiane sesquiterpene lactone, an unusual pyridinium alkaloid with a sulfated guaiane sesquiterpene lactone nucleus, an amino conjugate of a sulfated guaiane sesquiterpene lactone, a bisabolane sesquiterpene, three tirucallane triterpenes, and six known compounds, were isolated from roots of Scorzonera divaricata. Their structures and absolute configurations were established based on chemical and spectroscopic methods, X-ray single crystal crystallography, and also by comparison with experimental and calculated ECD spectra. One of the tirucallane triterpenes exhibited significant cytotoxic activities against four human cancer cell lines (HL60, HeLa, HepG2, and SMMC-7721) in vitro. Two of sulfated guaiane sesquiterpenoids also exhibited antioxidant activities by scavenging ABTS cation free radicals. Tirucallane-type and dammarane-type triterpenes were not previously known in the genus Scorzonera. The study suggests that sulfated guaiane-type sesquiterpenoids are a valuable marker for systematic chemical studies in the Lactuceae tribe of the Asteraceae.

Qualitative and quantitative analyses of secondary metabolites in aerial and subaerial of Scorzonera hispanica L. (black salsify).

Scorzonera hispanica commonly known as black salsify is a perennial herbaceous plant belonging to the Asteraceae family. The subaerial parts of black salsify are cultivated in Central and Southern Europe as a vegetable. There are only few reports on the chemical composition of S.hispanica. The aim of the present study was to determine the chemical composition of subaerial and aerial parts of this species. In total, twelve compounds were isolated and identified with spectroscopic methods, including a series of seven rare sesquiterpenoids - five bisabolane and two curcumenal derivatives. Furthermore, a fully validated HPLC-DAD-CAD method for the quantification of phenolic compounds of S. hispanica was developed. The cytotoxicities of lignan [(-)-syringaresinol (1)] and bisabolane derivatives from S. hispanica against several cancer cell lines were studied. (-)-Syringaresinol was the only compound active against myeloma cell lines and was also active against colon cancer cell lines. However, this lignan was also found to be cytotoxic for normal peripheral blood mononuclear cells (PBMCs). Two bisabolane derivatives were active against colon cancer cell lines and may be interesting as lead structures for the development of new anti-colon cancer agents.

Effect of extraction solvents on the biomolecules and antioxidant properties of Scorzonera undulata (Asteraceae): Application of factorial design optimization phenolic extraction.

BACKGROUND: Phenolic compounds were extracted and isolated from S. undulata roots. METHODS: Sample of roots from E. hirta was tested for phenolic compounds, and in vitro antioxidant activity by diphenyl-1-picrylhydrazyl (DPPH) assay, ABTS, FRAP and reducing power was measured using cyano- ferrate method. RESULTS: The methanolic fraction exhibited the highest total phenol content (6.12 ±0.11 mg AGE/g DW). On the other hand, the highest flavonoids concentration was observed in ethyl acetate fraction (2.90 ±0.05 mg CE/g DW) in addition to anthocyanins (28.56 ±3.96 mg/l). Besides, the highest level of tannins content was measured in the polar aprotic solvent ethyl acetate extract (3.25 ±0.06 mg CE/g DW). The different extracts of S. undulata were evaluated for their radical scavenging activities by means of the DPPH assay. The strongest scavenging activity was observed in methanolic fraction scavenged radicals effectively with IC   values of 0.14 ±0.02 mg/ml. Similarly, the potassium ferricyanide reduction (FRAP) and ABTS•+ of methanol extract. On the other hand, the total reducing power of ethyl acetate extract was found higher than of other extracts. This paper presents the application of the design-of experiment method for optimizing the extraction of phenolic content using methanol solvent. The resulting regression model has shown that the effect of temperature is not statistically significant (with >95% certainty), while that of agitation speed is. The two main effects are contributed by the solvent concentration and the maceration period. CONCLUSIONS: Our results clearly showed that the extraction of phenolic compounds and their antioxidant capacity is significantly affected by solvent combinations. S. undulata presented the highest total phenolic content, total flavonoids content and antioxidant capacity values. The resulting regression model has shown that the effect of temperature is not statistically significant (with >95% certainty), while that of agitation speed is.

Turkish Scorzonera Species Extracts Attenuate Cytokine Secretion via Inhibition of NF-κB Activation, Showing Anti-Inflammatory Effect in Vitro.

Scorzonera species are used in different folk medicines to combat many diseases, including the illnesses connected with inflammation. Previous experiments showed anti-inflammatory activity of Scorzonera extracts in vivo. S. latifolia, S. cana var. jacquiniana, S. tomentosa, S. mollis ssp. szowitsii, S. eriophora, S. incisa, S. cinerea, and S. parviflora extracts were, therefore, evaluated for their inhibitory activities of TNF-α and IL-1ß production, and NF-κB nuclear translocation in THP-1 macrophages. The HPLC analysis was carried out to elucidate and to compare the composition of these extracts. Major compounds of the tested extracts have been isolated using different chromatographic techniques and further tested for their inhibitory activities on TNF-α and IL-1ß production. Several extracts showed promising anti-inflammatory activity in these in vitro tests. Results of HPLC analysis revealed chlorogenic acid as a compound present in all tested extracts. Hyperoside, quercetin-3-O-ß-d-glucoside and rutin were also present in varying amount in some Scorzonera species analyzed. Furthermore, eight phenolics which were identified as quercetin-3-O-ß-d-glucoside (1), hyperoside (2), hydrangenol-8-O-glucoside (3), swertisin (4), 7-methylisoorientin (5), 4,5-O-dicaffeoyl-quinic acid (6), 3,5-di-O-caffeoyl-quinic acid (7), and chlorogenic acid (8) have been isolated as major phenolic compounds of the tested extracts and, together with eight terpenoids (9-16) previously obtained from different Scorzonera species, have been tested for the inhibition of TNF-α production, unfortunately with no activity comparable with standard.

Bioassay-guided isolation of the antinociceptive compounds motiol and beta-sitosterol from Scorzonera latifolia root extract.

Scorzonera latifolia (Asteraceae) is a plant widely distributed in Central and East Anatolia. A mastic, named yaki sakizi, is prepared from the latex and roots of S. latifolia and similar species. This latex is used in Turkish folk medicine for its analgesic activity, as anthelmintic and against infertility. The aim of this study was to isolate the compounds responsible for the antinociceptive activity of S. latifolia using bioassay-guided fractionation. The methanolic extract of the S. latifolia roots was prepared and subjected to chromatographic purification. Isolated active compounds were identified by means of MS and NMR techniques. Writhing and tail-flick tests were used to determine antinociceptive activity. Motiol and beta-sitosterol were isolated as compounds with promising antinociceptive activity. It is suggested that antinociceptive activity of the plant extract is probably caused by the synergic interaction of the isolated compounds.

Prospective neurobiological effects of the aerial and root extracts and some pure compounds of randomly selected Scorzonera species.

CONTEXT: Scorzonera L. species (Asteraceae) are edible and as medicinal plants are used for various purposed in folk medicine. OBJECTIVE: The methanol extracts of the aerial parts and roots from 27 Scorzonera taxa were investigated for their possible neurobiological effects. MATERIALS AND METHODS: Inhibitory potential of the Scorzonera species was tested against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and tyrosinase (TYRO) at 100 µg mL(-1) using ELISA microtiter assay. Antioxidant activity of the extracts was tested with radical scavenging activity, metal-chelation capacity, ferric- (FRAP), and phosphomolibdenum-reducing antioxidant power (PRAP) assays. Chlorogenic acid, hyperoside, rutin, and scorzotomentosin-4-O-ß-glucoside were also screened in the same manner. Total phenol and flavonoid quantification in the extracts were determined spectrophotometrically. RESULTS: The aerial parts of Scorzonera pisidica (40.25 ± 0.74%) and chlorogenic acid (46.97 ± 0.82%) displayed the highest TYRO inhibition, while the remaining samples showed only trivial inhibition against cholinesterases (2.08 ± 1.35%-25.32 ± 1.37%). The same extract of S. pisidica was revealed to be the most potent in scavenging of all three radicals and FRAP assay. DISCUSSION AND CONCLUSION: Out of 27 taxa, S. pisidica, in particular, may deserve further investigation for its neuroprotective potential.

Antioxidant and free radical-scavenging activity of constituents from two Scorzonera species.

The aim of this study was to investigate the secondary metabolites content of Scorzonera papposa DC., an edible plant eaten in the desert region of Jordan and to assess its antioxidant and free radical-scavenging activity. By using this bioassay-oriented approach nine compounds, including the new natural compounds (6-trans-p-coumaroyl)-3-O-ß-D-glucopyranosyl-2-deoxy-D-riburonic acid (1), (6-cis-p-coumaroyl)-3-O-ß-D-glucopyranosyl-2-deoxy-D-riburonic acid (2a), (6-trans-p-coumaroyl)-3-O-ß-D-glucopyranosyl-2-deoxy-D-riburonic acid methyl ester (3), and (6-trans-p-coumaroyl)-3-O-ß-D-glucopyranosyl-(5-acetyl)-2-deoxy-D-riburonic acid (4), having the rare deoxy-D-riburonic acid moiety, were isolated. Their structures were elucidated by UV, MS, (1)H and (13)C NMR and 2D NMR. The antioxidant activity of the S. papposa pure compounds and of related derivatives isolated from another Scorzonera species (S. judaica Eig.) was also tested. The Relative Antioxidant Capacity Index (RACI) was applied as an integrated method to compare the antioxidant activities obtained using different chemical methods.