Katarzyna Szewczyk

Ethnobotany, phytochemistry, and bioactivity of the genus Turnera (Passifloraceae) with a focus on damiana—Turnera diffusa

ETHNOPHARMACOLOGICAL RELEVANCE Half a dozen of the currently accepted 135 Turnera species are used in traditional medicine, most notably Turnera diffusa Willd. ex Schult. which is one of the most highly appreciated plant aphrodisiacs. Other traditional uses of Turnera L. species include the treatment of anaemia, bronchitis, cough, diabetes, fever, fungal disease, gastrointestinal complaints, pain, pulmonary and respiratory diseases, skin disorders, and women׳s health problems. Additionally, Turnera species are used as abortives, expectorants, and laxatives. PHYTOCHEMISTRY Flavonoids (22 different compounds), maltol glucoside, phenolics, cyanogenic glycosides (7 different compounds), monoterpenoids, sesquiterpenoids, triterpenoids, the polyterpene ficaprenol-11, fatty acids, and caffeine have been found in the genus Turnera. BIOACTIVITY Bioactivities experimentally proven for members of the genus Turnera encompass antianxiety, antiaromatase, antibacterial including antimycobacterial, antidiabetic, antioxidant, adapatogenic, antiobesity, antispasmodic, cytotoxic, gastroprotective, hepatoprotective, and aphrodisiac activities. Most of these activities have so far been investigated only in chemical, cell based, or animal assays. In contrast, the antiobesity activity was also investigated in a study on healthy human subjects and with a herbal preparation containing among other ingredients Turnera diffusa leaves. Moreover, the enhancement of female sexual function was assessed in humans; again the product contained besides Turnera diffusa other potentially bioactive ingredients. However, with only few exceptions, most of the traditional uses and the experimentally verified bioactivities can currently not be related to a particular compound or compound class. A notable exception is the flavonoid apigenin, which was identified animal experiments as the antinociceptive principle of Turnera diffusa. CONCLUSION In this review, the current knowledge on ethnobotanical uses of members of the genus Turnera, the secondary metabolites reported from Turnera, and experimentally documented bioactivities from Turnera extracts and pure compounds derived from Turnera extracts are compiled. Moreover, some of the most interesting avenues for future research projects are being discussed briefly. These include in particular the aphrodisiac activity of Turnera diffusa and the antibiotic activity potentiating effect of Turnera ulmifolia L. against aminoglycoside resistant bacteria.

A New Method for the Isolation of Ergosterol and Peroxyergosterol as Active Compounds of Hygrophoropsis aurantiaca and in Vitro Antiproliferative Activity of Isolated Ergosterol Peroxide

In the present study, ergosterol peroxide and ergosterol were isolated for the first time from fresh fruit bodies of Hygrophoropsis aurantiaca (False Chanterelle). The substances were characterized mainly by spectroscopic methods (1H-NMR, 13C-NMR, DEPT-45, DEPT-90, DEPT-135, 2D-NMR). In our study, a new specific thin layer chromatographic method was developed for determination of ergosterol and ergosterol peroxide in H. aurantiaca extract. The method is based on the separation of n-hexane extract on silica gel (Silica Gel G) TLC plates using the optimized solvent system toluene/ethyl acetate (3:1; v/v). The main advantages of the developed method are the simplicity of operation and the low cost. The in vitro study results revealed the antiproliferative properties of ergosterol peroxide against LS180 human colon cancer cells. The described effect was attributed both to altered mitochondrial activity and decreased DNA synthesis. Additionally, in the same concentration range the investigated compound was not toxic to CCD 841 CoTr human colon epithelial cells. The present study suggests that fruit bodies of H. aurantiaca have great potential for producing substances and extracts with potential applications in medicine.

Densitometric HPTLC method for analysis of triterpenoids in the leaves of Jovibarba sobolifera (Sims.) Opiz (Hen and Chickens Houseleek)

High performance thin-layer chromatography (HPTLC) combined with densitometry has been used for analysis of the triterpenoid content of acetone and ethyl acetate extracts of the leaves of Jovibarba sobolifera (Sims.) Opiz. After optimization of the extraction process, HPTLC separation was successfully standardized, using silica gel plates washed with methanol and dichloromethane, dichloromethane-ethyl acetate 18.5:1.5 as mobile phase, and 8% H2SO4 in ethanol (m/m) as spray reagent. Triterpenoids in the leaves of Jovibarba sobolifera were quantified by measurement of absorbance. Three spots were observed on chromatograms - the sum of α and β-amyrin, oleanolic acid, and an unidentified compound. All of the triterpenoid components were analyzed for the first time in this plant. The triterpenoid content was calculated statistically.

Antioxidative and cytotoxic potential of some Chenopodium L. species growing in Poland.

The cytotoxic and antioxidant properties of lipophilic compounds extracted from different parts of four Chenopodium L. (Chenopodium album, Chenopodium hybridum, Chenopodium rubrum and Chenopodium urbicum) species were evaluated. The highest phenolic content was found in herb and seeds of all examined plants. Large amounts of free polyphenols were observed in herb extracts of C. album (3.36 mg/g DW), seeds of C. urbicum (3.87 mg/g DW) and roots of C. urbicum (1.52 mg/g DW). The cytotoxic activities of the extracts were assessed against human lung carcinoma A-549 and ovarian carcinoma TOV-112D and normal human fibroblast cell lines. Our study demonstrated that the extracts from the herb of C. rubrum and C. urbicum had the best antioxidant effect of all the extracts analyzed. Most of the extracts tested exhibited low cytotoxicity. However, the extracts from herb and seeds of C. album and C. hybridum showed the significant antiproliferative effect on the TOV-112 cell line. It can be concluded that antioxidant activity and phenolic composition differ mainly between plant parts and are quite similar between the plants, when the same plant part is analyzed. Thus, the Chenopodium extracts could be used as a readily accessible source of natural antioxidants, and may be used in the pharmaceutical industry and for food supplements production.

Comparison of the Essential Oil Composition of Selected Impatiens Species and Its Antioxidant Activities

The present paper describes the chemical composition of the essential oils obtained by hydrodistillation from four Impatiens species, Impatiens glandulifera Royle, I. parviflora DC., I. balsamina L. and I. noli-tangere L. The GC and GC-MS methods resulted in identification of 226 volatile compounds comprising from 61.7%–88.2% of the total amount. The essential oils differed significantly in their composition. Fifteen compounds were shared among the essential oils of all investigated Impatiens species. The majority of these constituents was linalool (0.7%–15.1%), hexanal (0.2%–5.3%) and benzaldehyde (0.1%–10.2%). Moreover, the antioxidant activity of the essential oils was investigated using different methods. The chemical composition of the essential oils and its antioxidant evaluation are reported for the first time from the investigated taxon.

UPLC-MS/MS Profile of Alkaloids with Cytotoxic Properties of Selected Medicinal Plants of the Berberidaceae and Papaveraceae Families

Cancer is one of the most occurring diseases in developed and developing countries. Plant-based compounds are still researched for their anticancer activity and for their quantity in plants. Therefore, the modern chromatographic methods are applied to quantify them in plants, for example, UPLC-MS/MS (ultraperformance liquid chromatography tandem mass spectrometry). Therefore, the aim of the present study was to evaluate the content of sanguinarine, berberine, protopine, and chelidonine in Dicentra spectabilis (L.) Lem., Fumaria officinalis L., Glaucium flavum Crantz, Corydalis cava L., Berberis thunbergii DC., Meconopsis cambrica (L.) Vig., Mahonia aquifolium (Pursh) Nutt., Macleaya cordata Willd., and Chelidonium majus L. For the first time, N,N-dimethyl-hernovine was identified in M. cambrica, B. thunbergii, M. aquifolium, C. cava, G. flavum, and C. majus; methyl-hernovine was identified in G. flavum; columbamine was identified in B. thunbergii; and methyl-corypalmine, chelidonine, and sanguinarine were identified in F. officinalis L. The richest source of protopine among all the examined species was M. cordata (5463.64 ± 26.3 μg/g). The highest amounts of chelidonine and sanguinarine were found in C. majus (51,040.0 ± 1.8 μg/g and 7925.8 ± 3.3 μg/g, resp.), while B. thunbergi contained the highest amount of berberine (6358.4 ± 4.2 μg/g).

Flavonoids from Jovibarba globifera (Crassulaceae) rosette leaves and their antioxidant activity

Seven flavonoids new for the genus Jovibarba, kaempferol 1, kaempferol 3-O-galactopyranosyl-(1 → 2)-O-α-l-rhamnopyranoside 2, kaempferol 3-O-β-d-glucoside 3, kaempferol 3-O-α-l-rhamnopyranosyl-7-O-α-d-glucofuranosyl-(1 → 2)-O-α-l-rhamnopyranoside 4, kaempferol 3-O-β-d-glucopyranoside-7-O-α-l-rhamnopyranoside 5, kaempferol 3,7,4′-O-trimethyl ether 6 and quercetin 7, were isolated from fresh and dried leaves of J.ovibarba globifera subsp. globifera. The structures of these compounds were established by analysis of their spectroscopic (1H and 13C NMR) and spectrometric (MS) data, as well as by comparison of these with those reported in the literature. All of the flavonoids are reported for the first time from the investigated taxon. In addition the antioxidant activities in DPPH test of selected compounds were evaluated.

Preliminary Characterization and Bioactivities of Some Impatiens L. Water-Soluble Polysaccharides

Preliminary characterization and bioactivity of water-soluble polysaccharides from four Impatiens species—I. glandulifera Royle, I. parviflora DC., I. balsamina L., and I. noli-tangere L.—were investigated. The yields of polysaccharides range widely from 1.97% for I. parviflora roots to 18.63% for I. balsamina aerial parts. SEC (Size exclusion chromatography) chromatograms show that all samples contained a low molecular weight part that consisted of components of similar molecular weight. The aerial parts and roots of I. balsamina, and I. glandulifera aerial parts had considerable amounts of high molecular weight components up to 2.3 MDa. The sugar composition analysis revealed that Impatiens polysaccharides consisted primarily of galactose, arabinose, rhamnose, mannose, xylose, and glucose. All polysaccharide fractions, except for I. parviflora roots, also contain galacturonic acid. Moreover, in vitro bioactivity of obtained polysaccharides were evaluated. The antioxidant activity was evaluated on the basis of 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2-azino-bis-(3-ethyl-benzthia-6-sulfonic acid) (ABTS) radical scavenging assays. The highest antioxidant activity was obtained for I. balsamina aerial parts and I. parviflora roots. Among the tested fractions, only the polysaccharides from I. glandulifera aerial parts were able to significantly decrease the production of IL-8 by 32.7 ± 10.5%. The results suggest that Impatiens species can be considered as a new source of antioxidants.

Phenolic constituents of the aerial parts of Impatiens glandulifera Royle (Balsaminaceae) and their antioxidant activities

Abstract As a continuation of investigating Impatiens L. genus, eight flavonoids, eriodyctiol, eriodyctiol 7-O-β-ᴅ-glucoside, kaempferol 3-O-β-ᴅ-glucoside, kaempferol 3-O-β-ᴅ-galactoside, kaempferol 3-rhamnosyl-di-glucoside, kaempferol 3-O-β-ᴅ-rutinoside, quercetin 3-O-β-ᴅ-glucoside and quercetin 3-O-β-ᴅ-galactoside, two phenolic acids – p-hydroxybenzoic acid and protocatechuic acid, and 2-methoxynaphthalene-1,4-dione were isolated from the aerial parts of I. glandulifera collected in Poland. The structures of the compounds were established by analysis of their spectroscopic (1H and 13C NMR) and spectrometric (MS) data, as well as by comparison of these with those reported in the literature. Quercetin 3-O-β-ᴅ-glucoside, kaempferol 3-O-β-ᴅ-galactoside and kaempferol 3-O-β-ᴅ-rutinoside were isolated for the first time from the investigated taxon. In addition, the antioxidant activities in different tests of all obtained compounds were evaluated. The results clearly showed that among analyzed constituents, quercetin 3-O-β-ᴅ-glucoside exhibited antioxidant activity comparable or better than ascorbic acid and Trolox which were used as a positive control. Graphical Abstract