Hasan Kırmızıbekmez

Yeditepe University · Faculty of Pharmacy

Qualitative and quantitative differences in the chemical composition between bee pollen originated from Castanea sativa (Türkiye and Slovenia), Salix spp. (Türkiye and Slovenia), and Quercus spp. (Türkiye) and androecia of Castanea sativa, Salix alba, and Quercus pubescens (apetalous trees) were evaluated for the first time by new high-performance...

Determination of the botanical origin of plant-originated bee products like propolis is a highly crucial task especially for the standardization of the extract and prediction of its health benefits. While there are various propolis types across globe, the existence of two main propolis types originating from black poplar and Eurasian aspen poplar h...

Inula viscosa L. has a well-documented history of therapeutic use, particularly in the Mediterranean region, where its medicinal properties have been recognized for centuries by local populations. This study aimed to evaluate the safety and biological activities of methanolic and aqueous extracts drived from I. viscosa. The total phenolic content (...

Etnobotanik çalışmalarda, Michauxia campanuloides L'Hérit. ex Aiton bitkisinin Güney Anadolu'da yara iyileştirici olarak kullanıldığı tespit edilmiştir. Michauxia türleri üzerinde yapılan çalışmalarda, in vitro antioksidan, antienflamatuvar, antimikrobiyal, sitotoksik ve in vivo yara iyileştirici etkilere sahip olduğu ortaya konulmuştur. M. campanu...

Bee pollen, known as a ‘life-giving dust’, is a product of honeybees using flower pollen grains and combining them with their saliva secretions. Thus, flower pollen could be an indicator of the bee pollen botanical source. Identification of bee pollen sources is a highly crucial process for the evaluation of its health benefits, as chemical composi...

Cytotoxic activity-guided isolation studies on the underground parts of Valeriana sisymbriifolia Vahl. led to the isolation of 12 secondary metabolites including two undescribed iridoids, sisymbriifolivaltrate and sisymbriifolioside, and two unreported sesquiterpene lactones, sisymbriifolins A and B. Chemical structures of the isolates were establi...

Cytotoxic activity-guided fractionation studies on Glycyrrhiza echinata roots led to the isolation of eight compounds (1–8). Chemical structures of the isolates were identified by NMR and MS analysis. Among the tested molecules, retrochalcones namely echinatin (3) (IC50=23.45–41.83 μM), licochalcone B (4) (IC50=36.04–39.53 μM) and tetrahydroxylmeth...

A previously unreported secoiridoid glycoside, cruciatoside (1) was isolated from the aerial parts of Gentiana cruciata L. along with ten known compounds eustomoside (2), eustomorusside (3), gentiopicroside (4), 6'-O-β-D-glucopyranosyl gentiopicroside (5), loganic acid (6), isoorientin (7), isovitexin (8), isovitexin 2''-(E)-ferulate (9), mangiferi...

Myrtus communis L. (Myrtle) plant parts have been traditionally used to treat various disorders. Herein, we aimed to compare the chemical compositions, antioxidant, anticancer, and anti/-mutagenic activities of the hydroalcoholic extracts prepared from floral buds, flowers, leaves, and fruits of Myrtle. Quercitrin, myricitrin, and myricetin 3-O-β-g...

The aim of this study was to isolate the cytotoxic compounds from V. alliariifolia via activity‐guided isolation and to determine the mechanism of actions of the most potent ones. The crude EtOH extract as well as CHCl3 and AcOEt subextracts demonstrated remarkable cytotoxic activities against A549, MCF7, HGC27 and PC3 cancer cells. Sequential chro...

Two unreported neolignans, speluncarins A (1) and B (2) together with seven known compounds (3–8, 13) were isolated from the underground parts of Valeriana speluncaria Boiss through cytotoxic activity-guided fractionation method. The crude extract, subextracts, main fractions and isolates were evaluated for their in vitro cytotoxic activities again...

Anthocyanins are pigments in the polyphenol class, which are found in high amounts especially in dark colored fruits and have high antioxidant properties, but Vaccinium fruit extract has low oral bioavailability and chemical instability. The purpose of this study was to develop a fast dissolving orodispersible film (FDOF) formulation containing ant...

The species belonging to Scrophularia genus grow mainly in Irano-Turanian and Mediterranean regions and have been used as folk remedy for inflammatory-related diseases since ancient times. The present study was aimed to evaluate the anti-inflammatory activity of the extracts of Scrophularia kotschyana as well as the isolated compounds. The aerial p...

The antioxidant and mutagenic/antimutagenic activities of the fixed oils from Nigella sativa (NSO) and Nigella damascena (NDO) seeds, obtained by cold press-extraction from the cultivar samples, were comparatively investigated for the first time. The antimutagenicity test was carried out using classical and modified Ames tests. The fatty acid compo...

From the MeOH extract of the aerial parts of Scutellaria brevibracteata subsp. subvelutina 12 secondary metabolites including eight iridoid glycosides (1-8), three flavonoids (9-11) and one phenylethanoid glycoside (12) were isolated. Their structures were elucidated as catalpol (1), globularin (2), scutellarioside II (3), picroside III (4), penste...

Bisabolol is one of the bioactive constituents of chamomile. It was aimed to biotransform (–)-α-bisabolol by different fungi for the production of new bioactive metabolites, which was converted to α-bisabolol oxide A and B by Thamnidium elegans. Additionally, the biotransformation by Penicillium neocrassum yielded a new metabolite, which was charac...

Propolis shows a great variation in its chemical content depending on the vegetation around the beehive. Determination of its botanical origin and the chemical characterization are the most important issues for the standardization and the quality evaluation for propolis samples that are intended to be used in the pharmaceutical industry. This study...

Sideritis congesta, an endemic plant to Turkey, is extensively consumed as energizing herbal tea and used as a remedy in folk medicine. This study was designed to comparatively evaluate the phytochemical composition and antioxidant potentials of different extracts (methanol, infusion) and fractions (chloroform, ethyl acetate, and remaining water) o...

A new depside, olivieridepside (1), and a new secoiridoid, olivierigenin (2) were isolated from the aerial parts of Gentiana olivieri Griseb. along with four known compounds, gentiopicroside (3), olivierosides A (4) and B (5) and isoorientin (6). The structures of the isolates were determined by extensive 1 D and 2 D NMR spectroscopy and HR-MS anal...

Herbal products as supplements and therapeutic intervention have been used for centuries. However, their toxicities are not completely evaluated and the mechanisms are not clearly understood. Dried rhizome of the plant kava (Piper methysticum) is used for its anxiolytic, and sedative effects. The drug is also known for its hepatotoxicity potential....

Five iridoid glycosides catalpol (1), specioside (2), ajugol (3), ajugoside (4), 8-O-acetylharpagide (5), two phenylethanoid glycosides, verbascoside (6) and glucopyranosyl-(1→Gi-6)-martynoside (7), four flavonoids, luteolin (8), luteolin 7-O-β-glucopyranoside (9), luteolin 7-O-rutinoside (10), apigenin 7-O-rutinoside (11), quercetin 3-O-rutinoside...

This study was undertaken to analyse the phenolic profiles of 19 propolis samples from Turkey by using an high‐performance thin‐layer chromatographic (HPTLC) method in order to identify their plant origins. Furthermore, their antioxidant and antimicrobial activity profiles were comparatively evaluated. For the appraisal of antioxidant potential tot...

This study was designed to comparatively evaluate the phytochemical composition and antioxidant potentials of fruit extracts from five Crataegus taxa (C. monogyna, C. orientalis, C. pontica, C. rhipidophylla and C. turcicus) growing wild in the flora of Turkey. Antioxidant activities of the samples were investigated using DPPH radical scavenging, F...

The aim of this study was to evaluate the ethanolic extract of propolis originated from northern Turkey for its antiproliferative, apoptotic and cell cycle arrest promoting effects on MCF7, HGC27, A549 cancer cell lines and a healthy cell line (HUVEC) in terms of DNA content, morphological features, expression of cell cycle checkpoint proteins p21,...

Three iridoid glycosides, 5-allosyloxy-aucubine (1), melittoside (2), ajugol (3), five phenylethanoid glycosides, verbascoside (4), martynoside (5), leucoseptoside A (6), lamalboside (7), decaffeoylverbascoside (8), four flavonoids, xanthomicrol (9), isoscutellarein 7-O-[6'''-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (10), 4'-O-methylisoscu...

Fourteen compounds (Fig.1) were isolated from the aerial parts of Scutellaria albida L. ssp. velenovskyi (Rech. f.) Greuter & Burdet, including four iridoids (1–4) catalpol, macfadienoside, mussaenosidic acid, albidoside; four flavonoids (5–8) hispidulin 7-Ο-β-D-glucuronide, scutellarin, xanthomicrol, eriodictyol; four phenylethanoid glycosides (9–...

Background Glycyrrhiza (licorice) species are rich in bioactive secondary metabolites and their roots are used traditionally for the treatment of several diseases. In recent years, secondary metabolites of licorice are gaining popularity, especially due to their significant cytotoxic and antitumor effects. However, Glycyrrhiza iconica, an endemic s...

Licorice (Glycyrrhiza glabra L.) is one of the most widely used plants worldwide for its various pharmacological activities. The aim of this study was to isolate the potential cytotoxic secondary metabolites from the MeOH extract prepared from the roots of Glycyrrhiza glabra through bioactivity-guided isolation procedure and to elucidate their mech...

The objective of this study was to develop and validate a new HPLC method to quantify several flavonoids in the methanol extract prepared from the aerial parts of four Scutellaria L. taxa from flora of Turkey. A simple, sensitive and precise reversed phase HPLC-DAD method was developed and validated for simultaneous determination of six main flavon...

Four new iridoids (1-4), together with three known iridoids (5-7), one known flavonoid glycoside, three phenolic acids and one phytosterol were isolated from the roots of Valeriana dioscoridis. Their structures were elucidated by means of NMR spectroscopy and mass spectrometry. This is the first report on the phytochemical composition of the non-vo...

The fruits of Olea europaea L. is widely consumed as food, and olive pits are utilized in folk medicine to relieve gastric disturbances. In the present study, the possible anti-inflammatory, analgesic and antioxidant activities of aqueous extracts of black (BP) and green olive (GP) pit prepared at gastric fed state pH were evaluated in vitro. Moreo...

A new HPLC-DAD method was developed and validated for simultaneous determination of six main phenylethanoid glycosides (calceolarioside D, neocalceolarioside D, verbascoside, isoverbascoside, leucoseptoside A and martynoside) in the aerial parts of four Scutellaria L. taxa from flora of Turkey. All standard compounds showed a good linearity (R² > 0...

Phytochemical investigations on the EtOH extract of Clematis viticella led to the isolation of six flavonoid glycosides, isoorientin (1), isoorientin 3′-O-methyl ether (2), quercetin 7-O-α-L-rhamnopyranoside (3), quercetin 3,7-di-O-α-L-rhamnopyranoside (4), manghaslin (5) and chrysoeriol 7-O-β-D-glucopyranoside (6), one phenylethanol derivative, hy...

The in vitro anti-inflammatory activity profile of the Nerium oleander flower EtOH extract/its subextracts (n-hexane, CH2Cl2, EtOAc, remaining H2O) were evaluated on LPS induced Raw 264.7 macrophages. The effects of the crude EtOH extract and its subextracts on nitric oxide (NO) production and cell viability were determined. The most active subextr...

Oleander (Nerium oleander L., fam: Apocynaceae) is an evergreen shrub. Although it is known to be poisonous to humans, a large number of utilizations in folk medicine have been reported against diabetes, rheumatic pain and skin diseases. The present study aimed to investigate the cholinesterase inhibitory activities of oleander flower extracts and...

The components of the essential oil obtained from the dried aerial parts of Sideritis trojana Bornm. by hydrodistillation was analyzed both by GC-FID and GC-MS, simultaneously. Overall 57 compounds were identified representing 83.8% of the oil. The major components of the oil were identified as valeranone (11.3%), α-bisabolol (10.9%) and β-caryophy...

The present study was undertaken to evaluate the in vivo analgesic activities of the extracts prepared from the aerial parts and roots of Scrophularia kotscyhana and to isolate the bioactive metabolites from the most active extract. Analgesic activities of all extracts and subextracts at the doses of 5, 10 and 30 mg/kg (i.p.) were examined using ho...

A new phenylethanoid glycoside, named digiviridifloroside (1), was isolated from the leaves of Digitalis viridiflora Lindley along with a known phenylethanoid glycoside, calceolarioside A (2), two flavonoid glycosides, scutellarein 7-O-beta-D-glucopyranoside (3) and hispidulin 7-O-beta-D-glucopyranoside (4), two cleroindicins, cleroindicins B (5) a...

Three new iridoid glycosides, named involucratosides A-C (1-3) were isolated from the H2O subextract of crude MeOH extract prepared from the aerial parts of Asperula involucrata along with a known iridoid glycoside (adoxoside), three flavone glycosides (apigenin 7-O-β-glucopyranoside, luteolin 7-O-β-glucopyranoside, apigenin 7-O-rutinoside) as well...

A new and rare type of iridoid glycoside, agnusoside (1), a new caffeoylquinic acid derivative, castusic acid (2), and a new sugar ester, 1,2-di-(4-hydroxybenzoyl)--glucopyranose (3), along with ten known compounds belonging to iridoid glycosides (agnuside, trans-eurostoside), caffeoylquinic acid derivatives (chlorogenic acid and isochlorogenic aci...

Context Some Ajuga L. (Lamiaceae) species are traditionally used for the treatment of malaria, as well as fever, which is a common symptom of many parasitic diseases. Objective In the continuation of our studies on the identification of antiprotozoal secondary metabolites of Turkish Lamiaceae species, we have investigated the aerial parts of Ajuga...

Context: Natural products can present remarkable biological and pharmacological activities. In traditional medicine, plants have been used historically in treating cancer, infections, and other inflammatory conditions. Objective: Verbascoside and catechin are widespread polyphenolic plant compounds that could play a role in the anti-inflammatory...

The in vitro anti-inflammatory effects of subextracts (n-hexane, chloroform, ethyl acetate, n-butanol, remaining water) of the methanol extract of the leaves of Sambucus ebulus L. (Adoxaceae) were investigated for their inhibitory activities on the activation of Nuclear factor kappa B (NF-κB) on lipopolysaccharide induced Raw 264.7 cells. The n-hex...

Cistus laurifolius L. (Cistaceae) is known as 'laden' in Anatolia and the leaves of the plant are used against rheumatismal diseases traditionally [1]. The ethanol extract of the leaves were submitted to solvent-solvent extractions and n-hexane, chloroform, ethyl acetate, n-butanol, remaining water subextracts were obtained. The extract and subextr...

From the MeOH extract of the leaves of Digitalis viridiflora Five phenylethanoid glycosides (1-5) including a new one were isolated. The structure of the new compound was established as 3,4-dihydroxy-beta-phenylethoxy-O-beta-quinovopyranosyl-(1 -> 6)-4-O-caffeoyl-beta-glucopyranoside (viridifloroside, 1) based on extensive 1D- and 2D-NMR spectrosco...

A new nonglycosidic iridoid, sambulin B (1), was isolated from the methanol extract of Sambucus ebulus L. leaves along with a recently reported new nonglycosidic iridoid, 10-O-acetylpatrinoside aglycone (sambulin A) (2); 2 flavonoids, isorhamnetin-3-O-beta-D-glucopyranoside (3) and isorhamnetin-3-O-rutinoside (4); and a mixture of 2 flavonoids (5),...

Rosmarinic acid (RA), which is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid, is one of the most significant phenolic compound in the family Lamiaceae, which is restricted to the subfamily Nepetoideae, including Salvia species. Since various biological effects have been attributed to RA content of medicinal plants, has recently gained...

A new flavonol glycoside, quercetin 3‐O‐[6′′′‐O‐3,5‐dihydroxycinnamoyl‐β‐glucopyranosyl‐(1→2)]‐β‐galactopyranoside (named lilacifloroside; 1) and a new iridoid 2 (named asperulogenin), were isolated from the aerial parts of Asperula lilaciflora in addition to eight known secondary metabolites, i.e., quercetin, kaempferol, quercetin 3‐O‐β‐glucopyran...

From the methanolic extract of the underground parts of Globularia cordifolia, a new iridoid glycoside, 5-hydroxydavisioside (1) and a new bisiridoid glycoside, globuloside C (2) were isolated along with six known iridoid glycosides, aucubin, melampyroside, monomelittoside, globularifolin, alpinoside and asperuloside. The structures of the isolates...

Two new iridoids, 10-O-benzoylglobularigenin (1) and dumuloside (2) were isolated from the aerial parts of Globularia dumulosa together with seven known iridoid glucosides, davisioside (3), aucubin (4), melampyroside (5), catalpol (6), 10-O-benzoylcatalpol (7), alpinoside (8) and deacetylalpinoside (9). Three phenylethanoid glycosides, verbascoside...

From the methanolic extract of the underground parts of Globularia orientalis, a new antioxidant sugar ester was isolated. The structure of the new compound, globularitol (1), was identified as 6-O-feruloyl-beta-D-glucopyranosyl-(1-->6)-glucitol by spectroscopic methods (1D and 2D NMR, ESI- and FAB-MS) and confirmed by chemical means.

From the aerial parts of the plant Phlomis chimerae, a new neolignan glucoside, (-)-4-O-methyldihydrodehydrodiconiferyl alcohol-9'-O-beta-D-glucopyranoside (1) was characterized along with the known neolignan glucosides, (-)-4-O-methyldehydrodiconiferyl alcohol-9'-O-beta-D-glucopyranoside (= longifloroside A) (2) and (-)-dihydrodehydrodiconiferyl a...

From the aerial parts of Phlomis tuberosa a new iridoid glucoside, chlorotuberoside was isolated together with five known iridoid glucosides, lamalbide, shanzhiside methyl ester, 7-epi-phlomiol (= phloyoside I), sesamoside and 5-deoxysesamoside. Two known phenylethanoid glycosides, forsythoside B, and decaffeoylacteoside, three known neolignan glyc...

From the aerial parts of Calendula arvensis a new triterpene saponin arvensoside C (1) was isolated together with four known triterpene saponins. The aglycon moieties had the oleanane skeleton for all of them. Three known flavonol glycosides, isorhamnetin 3-O-β -D-glucopyranoside, quercetin 3-O-β -D-glucopyranoside and quercetin 3-O-β -D-galactopyr...

Together with ten well known compounds, the quinic acid derivative chlorogenic acid, the nucleoside adenosine, two amino acids, tryptophan and phenylalanine, the anthraquinone derivatives, aloemodin, aloemodin acetate and chyrosphanol 1-O-gentiobioside, the flavon C-glycosides, isovitexin, isoorientin and isoorientin 4’-O-β -glucopyranoside, as wel...

A new flavone glycoside, 6-hydroxyluteolin 7-O-[6m-benzoyl-β -D-glucopyranosyl-(1 → 2)]-β - D-glucopyranoside (aphyllanthoside, 1) was isolated from the MeOH extract of the aerial parts of Globularia aphyllanthes. Besides this new compound, two flavonoid glycosides (6-hydroxyluteolin 7-O-[6m-(E)-caffeoyl-β -D-glucopyranosyl-(1 → 2)]-β -D-glucopyran...

The phytochemical investigation of Digitalis trojana led to the isolation of two cardiac glycosides (1, 2), one pregnane glycoside (3), three furostanol type saponins (4-6), along with three cleroindicins (7-9), four phenylethanoid glycosides (10-13), two flavonoids (14, 15) and two phenolic acid derivatives (16, 17). The structure elucidation of t...

The potential effects of globularifolin, an acylated iridoid glucoside, on cell survival, inflammation markers and free radicals scavenging were investigated. Viability assay on human myelomomonocytic cell line THP-1 and human peripheral blood mononuclear cells (PBMC) using the Cell-Titer Blue assay proved that globularifolin had no toxic effect at...

The antioxidant activity of the 80% methanolic extract of Cornus mas L. leaves (CMM) was evaluated by various methods both in vitro and in vivo. In vitro screening tests indicated that CMM had high antioxidant activity in terms of free radical scavenging and metal reducing activity. In vivo antioxidant activity studies in normal healthy rats demons...

Some members of the genus Asperula are consumed as diuretic, for constipation as well as tonic [1]. Flavonoids, anthraquinones, iridoids, phenolic acids as well as phytosterols have been reported from various Asperula species [2,3]. In this study, we have examined the constituents of Asperula lilaciflora, endemic to Turkey, as contribution to the c...