Chemical profile of the Anatolian Sideritis species with bioactivity studies.

CONTEXT: The genus Sideritis L. (Lamiaceae) is represented by 46 species in Turkey with an 79% endemism ratio, 42 of 46 belonging to the section Empodoclia. OBJECTIVE: In this review article, Sideritis species growing in Turkey have been evaluated for phytochemical constituents and biological activities. METHODS: The data for the isolates, components and extracts of the Anatolian Sideritis species and their bioactivity studies were retrieved from the main databases WoS, Scopus and PubMed from 1975 until 31 December 2022. RESULTS: In this review article, terpenoids, flavonoids, phenolics and other secondary metabolites isolated from Turkish Sideritis species were reported. Anatolian Sideritis species, which primarily consist of monoterpenes and sesquiterpenes, were studied in detail. Sideritis plants are represented by 46 species in Turkey, and 25 of them were investigated for their diterpenoids through isolation or LC-MS studies. Most of the diterpenoids of Turkish Sideritis species have ent-kaurene skeleton, among them linearol, siderol, 7-epicandicandiol and sideridiol were found to be the main compounds. Exceptionally, labdane, pimarane and beyerene diterpenoids were only found in a few species. For phenolics and flavonoids, only 12 species were investigated until now, and they were found to be rich in phenylethanoid glycosides and flavonoid glycosides. In terms of activity, most of the species were tested for antioxidant activity, followed by antimicrobial and anti-ulcer/anti-inflammatory activities. Their cytotoxic, enzyme inhibitory, antinociceptive and antistress activities were less frequently studied. CONCLUSIONS: Sideritis species should be considered promising therapeutic agents in the treatment of upper respiratory tract and ulcer/inflammatory diseases.

African Mountain Thistles: Three New Genera in the Carduus-Cirsium Group.

The floras on the highest mountains in tropical eastern Africa are among the most unique floras in the world. Despite the exceptionally high concentration of endemic species, these floras remain understudied from an evolutionary point of view. In this study, we focus on the Carduus-Cirsium group (subtribe Carduinae) to unravel the evolutionary relationships of the species endemic to the tropical Afromontane and Afroalpine floras, aiming to improve the systematics of the group. We applied the Hyb-Seq approach using the Compositae1061 probe set on 190 samples (159 species), encompassing representatives of all genera of Carduinae. We used two recently developed pipelines that enabled the processing of raw sequence reads, identification of paralogous sequences and segregation into orthologous alignments. After the implementation of a missing data filter, we retained sequences from 986 nuclear loci and 177 plastid regions. Phylogenomic analyses were conducted using both concatenated and summary-coalescence methods. The resulting phylogenies were highly resolved and revealed three distinct evolutionary lineages consisting of the African species traditionally referred to as Carduus and Cirsium. Consequently, we propose the three new genera Afrocarduus, Afrocirsium and Nuriaea; the latter did notably not belong to the Carduus-Cirsium group. We detected some incongruences between the phylogenies based on concatenation vs. coalescence and on nuclear vs. plastid datasets, likely attributable to incomplete lineage sorting and/or hybridization.

East Asian-North American disjunctions and phylogenetic relationships within subtribe Nepetinae (Lamiaceae).

Biogeographic disjunctions, including intercontinental disjunctions, are frequent across plant lineages and have been of considerable interest to biologists for centuries. Their study has been reinvigorated by molecular dating and associated comparative methods. One of the "classic" disjunction patterns is that between Eastern Asia and North America. It has been speculated that this pattern is the result of vicariance following the sundering of a widespread Acrto-Teritary flora. Subtribe Nepetinae in the mint family (Lamiaceae) is noteworthy because it contains three genera with this disjunction pattern: Agastache, Dracocephalum, and Meehania. These disjunctions are ostensibly the result of three separate events, allowing for concurrent testing of the tempo, origin, and type of each biogeographic event. Using four plastid and four nuclear markers, we estimated divergence times and analyzed the historical biogeography of Nepetinae, including comprehensive sampling of all major clades for the first time. We recover a well-supported and largely congruent phylogeny of Nepetinae between genomic compartments, although several cases of cyto-nuclear discordance are evident. We demonstrate that the three disjunctions are pseudo-congruent, with unidirectional movement from East Asia at slightly staggered times during the late Miocene and early Pliocene. With the possible exception of Meehania, we find that vicariance is likely the underlying driver of these disjunctions. The biogeographic history of Meehania in North America may be best explained by long-distance dispersal, but a more complete picture awaits deeper sampling of the nuclear genome and more advanced biogeographical models.

Cytotoxic Effects of Some Nepeta Species against Breast Cancer Cell Lines and Their Associated Phytochemical Properties.

Nepeta is one of the largest genera of the Lamiaceae family. Nepeta species are commonly employed in traditional medicine for a variety of ailments, as well as food additives. In addition, they also come to the fore with their rich phytochemical content. In the present study, the quantitative phytochemical content of methanolic extracts and infusions prepared from the aerial parts of 14 Nepeta taxa collected from Turkey and their cytotoxic effects on two breast cancer cell lines, MCF-7 and MDA-MB-231, were investigated by using the MTT (3-(4,5-dimethylthiazol-2-yl))-2,5-diphenyltetrazolium-bromide) test. According to HPLC-PDA analysis, N. racemosa methanolic extract had the highest ursolic acid content with 165.9 mg/g extract. Total sterol, total iridoid, and total triterpenoid content were determined to be greatest in the methanolic extracts of N. meyeri, N. trichocalyx and N. phyllochlamys. The MTT experiment demonstrated that certain Nepeta species suppressed the growth of MCF-7 and MDA-MB-231 cells in a dose-dependent manner. Statistical analysis revealed a strong correlation between the cytotoxic effects of the extracts and their triterpene content. In conclusion, the data obtained from this study are important in terms of forming a basis for advanced anticancer activity studies on breast cancer with Nepeta sp.

Biological activities of some Salvia species.

In this study, total phenolic, flavonoid and protein contents, antiradical capacities, antibacterial and cytotoxic properties of five different Salvia species (Salvia macrochlamys Boiss., Salvia kronenburgii Rech.f., Salvia euphratica Montbret. ex Aucher var. euphratica, Salvia huberi Hedge and Salvia kurdica Benth) were investigated. The total phenolic content of the species was in the range of 59.6 ± 20 to 150.1 ± 1.1 mg/g, total flavonoid content in the range of 20.4 ± 2.2 to 38.9 ± 4.1 mg/g, and total protein content in the range of 14.0 ± 0.5 to 22.0 ± 1.1 mg/g. Radical scavenging capacities of the Salvia species were determined in the range of 84.1 ± 4.5 to 96.8 ± 0.1%. Moreover, Salvia extracts showed powerful antibacterial activity against Escherichia coli and Staphylococcus aureus bacteria. Cytotoxic effects of the samples on human lymphocytes were determined by MTS assay and S. kronenburgii and S. euphratica var. euphratica decreased the harmful effects of 2-hydroperoxy-2-methylpropane (tert-butyl hydroper-oxide, t-BOOH) at all time points tested. The highest amounts of rutin hydrate belong to S. kronenburgii and S. euphratica var. euphratica, and the highest amounts of luteolin-7-glucoside belong to S. huberi and S. kronenburgii. Vanillic acid was present only in S. huberi and S. kurdica.

Composition of the essential oil of Satureja metastasiantha: a new species for the flora of Turkey.

The aerial parts of Satureja metastasiantha were hydrodistilled for 3 h using a Clevenger-type apparatus. The essential oils were analyzed by gas chromatography/flame ionization detector and gas chromatography/mass spectrometry, simultaneously, the main compounds of which were characterized as p-cymene (22.3%), thymol (21.0%), carvacrol (18.4%), and γ-terpinene (12.1%). Antioxidant capacity, acetylcholinesterase and butyrylcholinesterase inhibition effects, and antimicrobial and antifungal properties of the species were evaluated. The anticholinesterase activity of the essential oil of S. metastasiantha was observed with 30% inhibition at 200 µg/mL. The essential oil of the species showed activity against Staphylococcus aureus with 128 µg/mL minimum inhibitory concentration value.

Rosmarinic and carnosic acid contents and correlated antioxidant and antidiabetic activities of 14 Salvia species from Anatolia.

Herbal medicine has been used worldwide as an alternative treatment. Salvia genus is one of the most remarked herbs which is traditionally used in the treatment of many diseases. Therefore, it is a crucial issue to reveal the chemical and biological profiles of different Salvia species. Rosmarinic and carnosic acid are the most well-known bioactive components generally accepted as the main antioxidant compounds in Salvia. This study firstly aims the determination of rosmarinic and carnosic acid contents of 14 Anatolian Salvia species by a simple and rapid capillary electrophoresis method. Moreover, the antioxidant activities and total phenolic contents of the Salvia samples were investigated. α-Glucosidase enzyme inhibitory effects of the samples were tested concerning their antidiabetic activities. The rosmarinic acid contents in the samples were well-correlated with the bioactivities.

Comparative anatomical studies of some Teucrium sect. Teucrium species: Teucrium alyssifolium Stapf, Teucrium brevifolium Schreb. and Teucrium pestalozzae Boiss. (Lamiaceae).

Teucrium alyssifolium Stapf (endemic), Teucrium pestalozzae Boiss. (endemic) and Teucrium brevifolium Schreb. are three closely related taxa in Teucrium sect. Teucrium. The obtained data from the anatomical studies revealed that these three taxa represent the general anatomical characteristics of the Lamiaceae family. Leaves, anatomical features such as thick cuticle, abundant trichomes, rich palisade parenchyma layer in the mesophyll provide evidence that these three species are xeromorphic structures. Leaf and stem anatomy showed that the taxa have generally similar anatomical features. However, cuticle layers, epidermis cells size, indumentum density, mesophyll types, palisade parenchyma occupied in the mesophyll, presence of spherocrystals in leaves and parenchyma, collenchyma and sclerenchyma layers in stems show differences amongst the taxa. Anatomical characters of leaf and stem of these taxa are examined for the first time in this study.

α-Glucosidase enzyme inhibitory effects and ursolic and oleanolic acid contents of fourteen Anatolian Salvia species.

During the last decade, ursolic and oleanolic acids have been of considerable interest because of their α-glucosidase inhibitory activities and potential effects for treatment of type 2 diabetes. A simple and sensitive reversed-phase HPLC method was developed for the simultaneous determination of ursolic acid and oleanolic acid. The optimal mobile phase was selected as 85% acetonitrile solution. The limit of detection of the method for ursolic acid and oleanolic acid were 14 ng mL-1 and 13 ng mL-1, respectively. The method showed good precision and accuracy with intra-day and inter-day variations of 0.54% and 7.33% for ursolic acid, intra-day and inter-day variations of 0.51% and 5.26% for oleanolic acid, and overall recoveries of 97.8% and 98.5% for ursolic acid and oleanolic acid, respectively. Application of the method to determine the ursolic acid and oleanolic acid contents in the Salvia species revealed both compounds, with varying amounts between 0.21-9.76 mg g-1 ursolic acid and 0.20-12.7 mg g-1 oleanolic acid, respectively, among 14 Salvia species analyzed. Additionally, the plant extracts were analyzed for their inhibitory activities on α-glucosidase. According to the results of this assay, the extracts showed considerable activity on α-glucosidase with IC50 values from 17.6 to 173 µg mL-1. A strong negative correlation was detected between the amounts of both acids and IC50 values of extracts. Anatolian Salvia species have great potential as functional plants in the management of diabetes.

Bioactive constituents of Salvia chrysophylla Stapf.

The dichloromethane extract of the aerial parts of Salvia chrysophylla Stapf (Lamiaceae), which is an endemic species to south-western Anatolia, was studied for non-volatile secondary metabolites for the first time in this study. Structures of the isolated compounds were elucidated as sclareol, ß-sitosterol, salvigenin, oleanolic acid and ursolic acid. The lipid peroxidation inhibitory activity and the DPPH free radical scavenging activity of the pure isolates were investigated to establish their antioxidant potential. Their anticholinesterase activity was carried out by the Ellman assay against both enzymes, acetylcholinesterase (AChE) and butyrylcholinesterase, and diterpene sclareol exhibited fairly good activity against both the enzymes while the two triterpenoids oleanolic and ursolic acids exhibited selective activity against AChE.

A novel isopimarane diterpenoid with acetylcholinesterase inhibitory activity from Nepeta sorgerae, an endemic species to the Nemrut Mountain.

From the dichloromethane extract of Nepeta sorgerae, the isolation and structure elucidation are now reported of a new isopimarane diterpenoid, named sorgerolone, and two known triterpenoids, oleanolic acid and ursolic acid. Antioxidant activity of the extracts and the isolated terpenoids was determined by the DPPH free radical scavenging and lipid peroxidation inhibition (beta-carotene bleaching) methods. Anticholinesterase activity of the extracts and isolates was investigated by Ellman's method against AChE and BChE enzymes. Although the antioxidant activity results were low, the AChE enzyme inhibition of the extracts and terpenoids was very promising.

Fatty acid composition and chemotaxonomic evaluation of species of Stachys.

The fatty acid composition of the seed oil of 23 Stachys taxa was analysed by GC/MS. The main compounds were found to be linoleic (27.1-64.3%), oleic (20.25-48.1%), palmitic (4.3-9.1%), stearic (trace to 5.2%) and 6-octadecynoic (2.2-34.1%) acids. The latter compound could be used as a chemotaxonomic marker of the genus Stachys. A cluster analysis was performed for comparison and characterisation of the seed oil from Stachys species.

Fatty acid composition of seeds of some species of Nepeta L.

The fatty acid compositions of Nepeta viscida, N. cilicica, N. crinita, N. nuda ssp. glandulifera and N. aristata were analyzed by GC/MS. The main free fatty acids were found as linolenic acid (49.8-58.5%), linoleic acid (10.9-23.5%), oleic acid (11.5-19.2%), palmitic acid (5.2-6.8%) and stearic acid (2.0-3.7%) and, total fatty acid compositions of species were analyzed and results were found as 36.2-49.8%, 17.1-25.8%, 15.4-25.8%, 6.4-7.8%, and 2.7-4.1%, respectively.

Fatty acid and tocochromanol patterns of some Salvia L. species.

In the course of our investigations of new sources of higher plant lipids, seed fatty acid compositions and the tocochromanol contents of Salvia bracteata, S. euphratica var. euphratica, S. aucherii var. canascens, S. cryptantha, S. staminea, S. limbata, S. virgata, S. hypargeia, S. halophylla, S. syriaca and S. cilicica were investigated using GLC and HPLC systems. Some of the species are endemic to Turkey. All the Salvia sp. showed the same pattern of fatty acids. Linoleic, linolenic and oleic acid were found as the abundant components. Tocochromanol derivatives of the seed oil showed differences between Salvia species. gamma-Tocopherol was the abundant component in most of the seed oils except of S. cilicica. The total tocopherol contents of the seed oils were determined to be more than the total of tocotrienols.

Fatty acid composition of seeds of Satureja thymbra and S. cuneifolia.

The chemical composition of fatty acid methyl esters (FAMEs) from seeds of S. thymbra and S. cuneifolia were analyzed by GC/MS. 7 FAMEs were identified from the seeds of S. thymbra mainly as 9-octadecenoic acid methyl ester (43.9%), hexadecanoic acid methyl ester (11.4%), 9,12,15-octadecatrienoic acid methyl ester (Z,Z,Z) (30.2%), and octadecanoic acid methyl ester (14.1%), while from the seed of S. cuneifolia 10 FAMEs were obtained with the main components, similar to S. thymbra. These were identified as 9-octadecenoic acid methyl ester (10.1%), hexadecanoic acid methyl ester (methyl palmitate, 34.6%), 9,12,15-octadecatrienoic acid methyl ester (Z,Z,Z) (6.3%) and octadecanoic acid methyl ester (1.8%).