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.

New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana.

Chromatographic separation ofn-hexane and ethyl acetate fraction of a crude methanol extract obtained from aerial parts of theScorzonera aucherianaDC collected from Sivas province of Turkey yielded nine natural compounds; two new 3-caffeoyl-quinic acid analogs (1-2), one new taraxasterol oleate (3), and six known triterpenoids taraxasterol (4), taraxasterol acetate (5), ptiloepoxide (6), lupeol (7), lupeol acetate (8), andß-sitosterol (9) were characterized. The structures of the isolated compounds were elucidated on the basis of NMR (1H,13C, COSY, HMBC, HSQC, and TOCSY), UV, FT-IR and LC-Q-TOF-MS spectrometric data.

Anatomical properties of Epilobium and Chamaenerion from a taxonomical perspective in Turkey.

In the present study, the anatomical features of stem, leaf, and fruit of 22 Epilobium L. and 4 Chamaenerion Séguier taxa were studied using light microscopy with the aim to find out taxonomically significant characters for the examined taxa. Principal component analysis indicated that the row number of collenchyma, presence of periderma and phloem fibers in the stem, the shape of midrib and idioblast, leaf type, and the shape of fruit in cross section are the most valuable anatomical traits delimiting the investigated taxa at generic and partly specific level. Additionally, the dendrograms resulted from unweighted pair-group method supported to describe members of Chamaenerion with circular or cordate midrib, equifacial leaf, cylindrical idioblast, and pericarp composed of T-form lobes and circular or rectangular central column and Epilobium with semicircular midrib, bifacial leaf, circular idioblast, and pericarp composed of m-form lobes and rectangular central column.

Altitude Variation in the Composition of Essential Oils, Fatty Acid Methyl Esters, and Antimicrobial Activities of Two Subspecies of Primula vulgaris Grown in Turkey.

In this study, the changes caused by variation of altitude to the essential oils (EOs), fatty acid methyl esters (FAMEs), and antimicrobial activities of Primula vulgaris Huds. subsp. vulgaris (Pvv) and P. vulgaris Huds. subsp. sibthorpii (Hoffmanns) W.W.Sm. & Forrest (Pvs)) grown in Turkey were investigated. Major fluctuations in the composition of Pvv and Pvs oils included methyl-4-methoxy salicylate (4.5-35.3%; Pvv and 3.2-37.2%; Pvs), (Z,Z,Z)-7,10,13- hexadecatrienal (5.1-21.8%; Pvv and 4.4-15.2%; Pvs ) and flavone (5.5-14.9%; Pvv and 1.6-18.0%; Pvs). Fatty acid profile (C60-CI6o) changes were noted in .Pvv and Pvs. Methyl hexadecanoate (2.4-9.3%) and methyl octadecanoate (1.0-4.7%) were present in all the FAME samples of the plants. The antimicrobial activity of the EOs of Pvv and Pvs were tested against nine bacterial species, which showed activity against Mycobacterium smegmatis with minimum inhibitory concentrations (MIC) varying from 8.5 to 59.2 pg/mL in all samples, respectively, depending on the altitude at which the oils were obtained.

Chemical constituents and antimicrobial activities of the essential oils from Sedum pallidum var. bithynicum and S. spurium grown in Turkey.

Chemical compositions of the essential oil of Sedum pallidum Bieb. var. bithynicum (Boiss.) and S. spurium Bieb. (Crassulaceae) from Turkey were investigated by GC-MS, and antimicrobial activity of the oil samples were assessed against Gram-positive/negative bacteria and yeast-like fungi. Thirty-eight and thirty-five components were identified in the essential oils and the main components of these species were found to be caryophyllene oxide from S. pallidum var. bithynicum and hexahydrofarnesyl acetone from S. spurium in the ratios of 12.8% and 15.7%, respectively. The isolated essential oils of the plants showed low antimicrobial activity against Gram-negative/positive bacteria and yeast-like fungi, having the MIC values of 500-2000 microg/mL. Antibacterial activity was not observed against Bacillus cereus.

Composition and antimicrobial activity of essential oils from Centaurea sessilis and Centaurea armena.

The essential oils of air-dried Centaurea sessilis and Centaurea armena obtained by hydrodistillation were analyzed by gas chromatography-mass spectrometry (GC-MS). Forty and twenty components were identified in the essential oils and the main component of these taxons was beta-eudesmol in the ratios of 12.4% and 19.3% from C. sessilis and C. armena, respectively. The antimicrobial activity of the isolated essential oil of the plants was also investigated. They showed moderate antibacterial activity against Gram-positive and Gram-negative bacteria, but no antifungal activity was observed against two yeastlike fungi.