Flower morphology as a predictor of pollination mode in a biotic to abiotic pollination continuum.

BACKGROUND AND AIMS: Wind pollination has evolved repeatedly in flowering plants, yet the identification of a wind pollination syndrome as a set of integrated floral traits can be elusive. Thalictrum (Ranunculaceae) comprises temperate perennial herbs that have transitioned repeatedly from insect to wind pollination while also exhibiting mixed pollination, providing an ideal system to test for evolutionary correlation between floral morphology and pollination mode in a biotic to abiotic continuum. Moreover, the lack of floral organ fusion across this genus allows testing for specialization to pollination vectors in the absence of this feature. METHODS: We expanded phylogenetic sampling in the genus from a previous study using six chloroplast loci, which allowed us to test whether species cluster into distinct pollination syndromes based on floral morphology. We then used multivariate analyses on floral traits followed by ancestral state reconstruction of the emerging flower morphotypes and determined whether these traits are evolutionarily correlated under a Bayesian framework with Brownian motion. KEY RESULTS: Floral traits fell into five distinct clusters, which were reduced to three after considering phylogenetic relatedness and were largely consistent with flower morphotypes and associated pollination vectors. Multivariate evolutionary analyses found a positive correlation between the lengths of floral reproductive structures (styles, stigmas, filaments and anthers). Shorter reproductive structures tracked insect-pollinated species and clades in the phylogeny, whereas longer structures tracked wind-pollinated ones, consistent with selective pressures exerted by biotic vs. abiotic pollination vectors, respectively. CONCLUSIONS: Although detectable suites of integrated floral traits across Thalictrum were correlated with wind or insect pollination at the extremes of the morphospace distribution, a presumed intermediate, mixed pollination mode morphospace was also detected. Thus, our data broadly support the existence of detectable flower morphotypes from convergent evolution underlying the evolution of pollination mode in Thalictrum, presumably via different paths from an ancestral mixed pollination state.

Dimeric benzylisoquinoline alkaloids from Thalictrum delavayi and their biological activities.

A phytochemical investigation of the whole plants of T. delavayi led to the isolation of five new dimeric benzylisoquinoline alkaloids, thalidelavines A-E (1-5), together with six known congeners (6-11). The structures and absolute configurations of new compounds were established based on analyses of spectroscopic data, ECD calculations, and single crystal X-ray crystallography. Thalidelavines A-E (1-5) were structurally complex bisbenzylisoquinoline alkaloids with various configurations. These isolated alkaloids were evaluated for their cytotoxic and immunosuppressive effects. Among them, both 9 and 10 displayed significant cytotoxicities against T98G cell lines with an IC50 value of 2.1 µM, compared with the positive CPT-11 (IC50 = 3.0 µM). In addition, 5-7 showed remarkable immunosuppressive effects. These findings not only enrich the structural diversity of bisbenzylisoquinoline alkaloids, but also provide potential candidates for the further development of the antitumor and immunosuppressive agents.

Ethnobotany, botany, phytochemistry and ethnopharmacology of the genus Thalictrum L. (Ranunculaceae): A review.

ETHNOPHARMACOLOGICAL RELEVANCE: Thalictrum (Ranunculaceae) is known for its important alkaloids which have been reported to exhibit various pharmacological activities, viz. antitumor, antimicrobial, antitussive, antiamebic, hypotensive effects, HIV antiviral, etc. Throughout the world, the plant has been used as a tonic, purgative, stimulant, aperient and is utilized in various systems of medicine in the treatment of various ailments like snake bite, jaundice, rheumatism, stomachache, wounds, swellings, uterine tumors, paralysis, joints pain, nervous disorders, toothache, diarrhea, piles, fever, peptic ulcer, ophthalmic, headache, diuretic, dyspepsia, convalescence, etc. AIMS OF THIS REVIEW: To bring together all the information regarding the botany, phytochemistry, ethnobotany and ethnopharmacology of Thalictrum and identify the gaps in the existing studies so that full medicinal potential of the genus can be realized. METHODS: Available literature on botany, geography, traditional uses, phytochemicals, and pharmacology was gathered by referring to library and electronic searches in PubMed, Science Direct, Google Scholar, relevant journals and books. RESULTS: A variety of phytochemicals like alkaloids, essential oils, glycosides, phenols and terpenoids have been reported from Thalictrum species. Alkaloids are the most dominant diverse group with 178 different types. The crude extracts and isolates exhibit a gamut of pharmacological activities, namely anticancer, antimalarial, antioxidant, antipyretic, anti-tumor, ant-influenza virus, contraceptive and immunosuppressive. Northalrugosidine, an alkaloid from T. alpinum shows in vivo antileishmanial activity. So far, cytotoxic effects of only three Thalictrum species, viz. T. dasycarpum, T. foliolosum and T. simplex have been reported. Thl isolated from T. simplex is found to be 50% toxic (CC50%) at the concentration ranging from 53 to 95 µM. CONCLUSIONS: Thalictrum has tremendous medicinal values used in many traditional systems of medicine. It has multiple chemical components and still there is scope to explore more. Multiple chemical constituents and its utilization signify its high demand in the drug markets or pharmaceutical companies. In depth phytochemical studies along with in vitro studies with respect to their active principles can help in tapping the full medicinal potential of the genus.

Assessment of phytochemicals, antioxidants and in-silico molecular dynamic simulation of plant derived potential inhibitory activity of Thalictrum foliolosum DC. and Cordia dichotoma G. Forst. against jaundice.

Medicinal plants have been exploited for therapeutic purposes since the dawn of civilization and have long been acknowledged essential to human health. The purpose of this research is to examine the scientific evidence for using the therapeutic herbal plants Thalictrum foliolosum DC. and Cordia dichotoma G. Forst. to treat hepatitis illness. The fundamental explanation for the therapeutic relevance of these plants is phytochemicals, which were evaluated qualitatively and quantitatively in three separate extracts with different solvent properties (methanol-polar, chloroform-non-polar, and aqueous-polar as one of the bases of traditional use). Flavonoids, phenols, tannins, saponins, and alkaloids were all evaluated for their presence in plant extracts, and it was observed that methanolic extract had the highest content of phytochemicals among different extracts whereas, the aqueous extract showed least amount of phytochemicals. Additionally, the antioxidant activity of these plants was also evaluated and methanolic extract was revealed with potential antioxidant activity, as also evidenced by the lowest half inhibitory concentration (IC50) values in the DPPH, ABTS, and high %inhibition in µM Fe equivalent of FRAP assays. Following that, the dominant phytochemicals were investigated using ultra-high performance liquid chromatography from the selected plants. Furthermore, default docking algorithms were used to appraise the dominant phytoconstituents for their in-silico investigation, in which rutin was found with the highest binding affinity (8.2 kcal/mol) and interaction with receptor which is further involved in causing jaundice. The receptor is infact an enzyme that is sphingomyelin phosphodiesterase Leptospira interrogans (PDB: 5EBB) which is holded back in its position by rutin and do not interact with Leptospira inferrogans spp which causes jaundice. Overall, the study suggested that these herbs have significant therapeutic properties, and their in-silico analysis strongly recommends further clinical investigations to get insight into the mechanisms of action in curing variety of diseases.

[Isoquinoline alkaloids from two species of Thalictrum genus plants].

The chemical constituents from the roots of Thalictrum cultratum and T. baicalense were investigated. By various isolation methods, such as silica gel, aluminium oxide, ODS, and Sephadex LH-20 column chromatographies, and semi-preparative HPLC, 11 simple isoquinoline alkaloids were isolated from the ethanol extract of the roots of these two plants, including a new compound, named dehydrothalflavine(1), and ten known ones(2-11): N-methylcorydaline(2), N-methylthalidaldine(3), thaliflavine(4), oxyhydrastinine(5), noroxyhydrastinine(6), dimethoxyisoquinolone(7), thalactamine(8), dehydronoroxyhydrastinine(9), 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline(10), and isopicnarrhine(11). Their structures were elucidated on the basis of HR-ESI-MS and 1 D and 2 D NMR techniques. Compound 1 was a new isoquinoline alkaloid. Compound 11 was obtained from Tha-lictrum plant for the first time. All compounds did not show cytotoxic activities against HL-60, U937, HCT116, Caco-2, and HepG2 cancer cell lines.

Effects of snow on reproduction of perennial Thalictrum dioicum: Plants survive but seedlings fail to recruit with reduced snow cover.

PREMISE: Future reductions in snow cover are expected in temperate climates, likely leading to more soil-freezing events and damage to plant tissues. However, whether and how plants can compensate for this damage may depend on the timing of damage and on plant allocations to seed size and number. We need more information about how seed production, germination, and seedling recruitment might respond to changes in snow cover. METHODS: We manipulated snow cover over three seasons in a common garden experiment with four treatments: (1) "control," where snowpack was left unmanipulated throughout the winter season; (2) "late addition," where snowpack was experimentally increased at the end of the winter season in order to delay the onset of spring; (3) "late removal," where snowpack was experimentally reduced at the end of the winter season in order to advance the onset of spring; and (4) "freeze," a consistent removal treatment, where snowpack was experimentally reduced following every substantial snowfall in order to induce freeze-thaw events in the soil. In all treatments, we measured survival, growth, reproduction, and recruitment of a native perennial herb, Thalictrum dioicum. RESULTS: Reduced snow cover minimally influenced adult survival. Instead, individuals that experienced reduced snow cover throughout the winter produced more massive seeds, whereas individuals that experienced a single snow removal at the end of the season produced less massive seeds. Seedling recruitment was lower in the removal treatments than in the control, as a result of failure to germinate in the freeze treatment and seedling mortality in the late removal treatment. CONCLUSIONS: Both reduced snow cover throughout the winter and a single late snow removal in the spring reduced seedling recruitment, but for different reasons, suggesting that a holistic approach to the life cycle is needed to understand responses to shifting climates.

Cytotoxic triterpenoid saponins from Thalictrum atriplex.

Two new cycloartane glycosides, cycloatriosides A and B (1-2), and a new oleanolic acid glycoside, thaliatrioside A (3), along with 7 known triterpenoids (4-10) were isolated from Thalictrum atriplex. The structures of the new compounds were established as 3-O-ß-D-galactopyranosyl (20S, 24 R)-3ß,16ß,25,29-tetrahydroxy-20,24-epoxycycloartane-29-O-ß-D-glucopyranoside (1), 3-O-ß-D-glucopyranosyl-(1→2)-α-arabinopyranosyl-3ß,22ξ,30-trihydroxycycloart-24-en-21-oic acid α-L-arabinopyranosyl-(1→6)-ß-D-glucopyranoside (2) and 3-O-[α-L-rhamnopyranosyl-(1→3)-ß-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl]-oleanolic acid 28-O-ß-D-glucopyranosyl ester (3) on the basis of extensive NMR and HR-ESI-MS analyses, along with acid hydrolysis. Their cytotoxic activities against human lung cancer cells A549 and human breast cancer cells MDA-MB-231 were evaluated using MTT method. Compound 9 showed cytotoxicity against MDA-MB-231 cell line with the IC50 value of 72.53 ± 1.08 µM.

Cytotoxic isoquinoline alkaloids from the roots of Thalictrum foliolosum.

Phytochemical investigation on the 70% EtOH extract of the roots of Thalictrum foliolosum DC. resulted in the isolation of three new isoquinoline alkaloids, 5,6,7,12-tetramethoxy-2-methyl-13-hydroxy-11-(4'-methoxycarbonylphenoxy)benzylisoquinoline (1), 5,6,7,12-tetramethoxy-2-methyl-13-hydroxy-11-(4'-carbonylphenoxy) benzylisoquinoline (2), and 3-methoxy-10-O-acetylprodensiflorin B (3). The new structures were elucidated by using spectroscopic data (NMR, IR, UV, and MS). The isolated alkaloids were tested in vitro for cytotoxic potentials against six human lung cancer cell lines (H460, H23, HTB-58, A549, H441, and H2170). As a result, alkaloids 1 and 2 exhibited significant cytotoxic activities against all the tested tumor cell lines with IC50 values less than 20 µM.

Thalictrum minus L. ameliorates particulate matter-induced acute lung injury in mice.

ETHNOPHARMACOLOGICAL RELEVANCE: Thalictrum minus L., which is widespread across Eurasia, is utilized as a folk medicine for treating dysentery, bedsore, fungal infection and lung inflammation in China, Mongolia and Iran. AIM OF THE STUDY: A Mongolian folk medicinal plant named Thalictrum minus L. (TML) has been extensively used for the treatment of lung inflammation, bacterial and fungal infection and tuberculosis. Our present study aims to investigate the effectiveness of TML against particulate matter (PM)-induced acute lung injury (ALI) and the potential underlying mechanisms. MATERIALS AND METHODS: Initially, HPLC-Q-TOF was applied for the qualitative analysis and HPLC was used for quantitative analysis of main components in TML. Then, the mice model of ALI was induced by PM via intratracheally instilled with 50 mg/kg body weight of Standard Reference Material1648a (SRM1648a), and TML (10, 20, 40 mg/kg) were administered orally 1 h prior to PM. The efficacy and molecular mechanisms in the presence or absence of TML were elucidated. RESULTS: Eleven main ingredients were detected in TML and the contents of homoorientin and berberine were quantified. Additionally, the results demonstrated that TML profoundly inhibited weight loss in mice and ameliorated lung pathological injury induced by PM. Furthermore, we also found that TML significantly decreased the lung wet to dry weight (W/D) ratios, reduced total protein in bronchoalveolar lavage fluid (BALF), and effectively attenuated PM-induced increased leukocyte and macrophages in BALF. Meanwhile, TML could pronouncedly inhibited myeloperoxidase (MPO) activity in lung tissues, decreased the PM-induced inflammatory cytokines including tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6) and interleukin-1ß (IL-1ß), reduced nitric oxide (NO) and increased superoxide dismutase (SOD) in BALF. In addition, TML markedly facilitated the expression of p-AMPK-Nrf2 and suppressed the expression of KEAP, prohibited the activation of the MAPKs-NLRP3/caspase-1 and cyclooxygenase-2 (COX2), and inhibited apoptotic pathways. CONCLUSION: These findings indicated that TML attenuated PM-induced ALI through suppressing the release of inflammatory cytokines and alleviating oxidative damage correlated with the AMPK-Nrf2/KEAP signaling pathways, MAPKs-NLRP3/caspase-1 signaling pathways, as well as apoptotic pathways.

Baicalensines A and B, Two Isoquinoline Alkaloids from the Roots of Thalictrum baicalense.

Baicalensines A (1) and B (2) were isolated from the roots of Thalictrum baicalense and structurally characterized using spectroscopic data, 13C NMR calculations, and the CASE algorithm. Compound 1, representing a new class of alkaloid dimers, contains berberine conjugated to a ring-opened isoquinoline. Compound 2 is the first reported natural benzylisoquinoline bearing a formyl group at C-3. Plausible biosynthetic pathways are proposed. Compound 1 exerted moderate cytotoxicity against the Caco-2 and HL-60 cell lines.

[A new antiviral isoquinoline alkaloid from Thalictrum glandulosissimum].

A new isoquinoline alkaloid(1) has been isolated from the whole plant of Thalictrum glandulosissimum by using various chromatographic techniques, including silica gel, sephadex, MCI-gel resin, and RP-HPLC, and its structure was determined as 1-(6-hydroxy-7-methylisoquinolin-1-yl) ethantone by physicochemical properties and spectroscopic data. This compound was evaluated for anti-tobacco mosaic virus(TMV) activity. The results showed that it had prominent anti-TMV activity with inhibition rates of 28.4%. This rate was closed to that of positive control.

Thalictrum foliolosum: A lesser unexplored medicinal herb from the Himalayan region as a source of valuable benzyl isoquinoline alkaloids.

ETHNOPHARMACOLOGICAL RELEVANCE: Thalictrum foliolosum DC (Ranunculaceae) is a perennial flowering herb traditionally used as a tonic, antiperiodic, diuretic, febrifuge, purgative and stomachic and for the treatment of snakebite, jaundice, and rheumatism. AIM OF THE STUDY: To provide a critical assessment of the state-of-the-art related to the traditional uses, phytochemistry, and pharmacology of T. foliolosum with the ultimate objective of providing further research strategies to facilitate the exploitation of the therapeutic potential of T. foliolosum for the treatment of human disorders. MATERIALS AND METHODS: Exhaustive bibliographic research related to T. foliolosum plant was carried out using scientific research engines and databases such as Google Scholar, PubMed, Web of Science covering all retrieved relevant manuscripts written in English. RESULTS: Several alkaloids such as berberine, jatrorrhizine, palmatine, thalrugosidine, thalrugosaminine, thalisopine (thaligosine), thalirugidine, thalirugine, 8-oxyberberine (berlambine), noroxyhydrastinine, N,O,O-trimethylsparsiflorine, thalicarpine, thalidasine, thalfoliolosumines A and thalfoliolosumines B were reported from T. foliolosum. Ethnomedicinal studies revealed much wider scope of T. foliolosum in developing various drugs to solve multiple challenges in the health sector. Therapeutic effects were attributed to the bioactivities of the secondary metabolites present in T. foliolosum. CONCLUSIONS: T. foliolosum is rich in berberine and other benzylisoquinoline alkaloids. T. foliolosum can be used as an excellent and effective herbal remedy for various human ailments since there are no reports on the toxicity of this herb.

The protective effects of Thalictrum minus L. on lipopolysaccharide-induced acute lung injury.

ETHNOPHARMACOLOGICAL RELEVANCE: Thalictrum minus L., a Mongolian folk medicinal plant, was applied for the treatment of bacterial and fungal infection, tuberculosis and lung inflammation. AIM OF THE STUDY: The present work aims to elucidate the protective effects of Thalictrum minus L.(TML) against lipopolysaccharide (LPS)-induced acute lung injury and the underlying mechanisms. METHODS: The mice model of acute lung injury was induced by LPS via endotracheal drip, and TML (10, 20, 40 mg/kg) were administered orally 1 h prior to LPS. The efficacy and molecular mechanisms in the presence or absence of TML were investigated. RESULTS: We demonstrated that treatment with TML aqueous extract protected the mice from acute lung injury induced by LPS administration. TML significantly inhibited weight loss in mice, decreased the lung wet to dry weight (W/D) ratios and attenuated lung histopathological changes, such as infiltration of inflammatory cells and coagulation, pulmonary edema. Furthermore, we found that TML markedly reduced the LPS-induced inflammatory cytokines including tumor necrosis factor-α (TNF-α) and interleukin-1ß (IL-1ß), decreased nitric oxide (NO), and increased superoxide dismutase (SOD) in bronchoalveolar lavage fluid (BALF), and effectively ameliorated LPS-induced increased total protein, leukocyte and macrophages in BALF. In addition, TML pronouncedly suppressed the activation of the MAPKs p38-NLRP3/caspase-1 and COX2, increased the expression of p-AMPK-Nrf2, and suppressed the expression of KEAP, apoptotic-related protein as well as autophagy. CONCLUSIONS: These results suggested that TML ameliorated LPS-induced acute lung injury by inhibiting the release of inflammatory cytokines and reducing oxidative damage associated with the MAPKs p38-NLRP3/caspase-1 and COX2 signaling pathways, AMPK-Nrf2/KEAP signaling pathways, as well as apoptosis and autophagy.

Racemic immunosuppressive seco-aporphine derivatives from Thalictrum wangii.

Thallactones A (1) and B (2), enantiomeric aporphine alkaloids with rare cleaved rings A and B, as well as thaliglucine N-oxide (3) and their biosynthetically related precursor, northalphenine (4), were isolated from the whole plant of Thalictrum wangii. Their structures with absolute configurations were elucidated by spectral techniques and electronic circular dichroism (ECD). Moreover, compounds 1, 3, and northalphenine inhibited concanavalin A (Con A)-stimulated proliferation of mice splenocyte significantly in a dose-dependent manner.

Three new isoquinoline alkaloids from the whole plants of Thalictrum tenue with cytotoxic activities.

Three new isoquinoline alkaloids, including two aporphines (1 and 2) and one oxoaporphine (3), were isolated from the 90% EtOH extract of the whole plants of Thalictrum tenue Franch. The structures of the isolated compounds were established based on 1D and 2D (1H-1H COSY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry, respectively. The isolated alkaloids were tested in vitro for cytotoxic activity against six esophageal carcinoma cell lines. Consequently, alkaloids 1-3 exhibited some cytotoxic activities against all the tested tumor cell lines with IC50 values less than 20 µM. [Formula: see text].

Antiplasmodial potential of Thalictrum foliolosum (Ranunculaceae) against lethal murine malaria.

BACKGROUND AND OBJECTIVES: The emergence of multi-drug resistant (MDR) strains of Plasmodium falciparum highlights the need to develop novel antimalarial drugs. Present study explores the in vivo antiplasmodial activity of ethanol leaf extract of Thalictrum foliolosum (ELETF) against lethal murine malaria. METHODS: The acute toxicity of the extract was assessed by Limit test of Lorke. The suppressive activity of the extract was evaluated by Peter's 4 day test. In vivo preventive and curative activity of ELETF was assessed by Peter's method and Ryley and Peter's method respectively. Biochemical assays were carried out using standard methods. RESULTS: ELETF (1000 mg/kg) exhibited considerable in vivo schizontocidal activity with 67.11% chemosuppression on Day 5. The ED50 of the extract was 579.56 mg/kg. ELETF also showed significant repository activity with 87.70% chemosuppression at 750 mg/kg, which was greater than pyrimethamine (78.78%). ELETF exhibited dose dependent chemosuppression in the curative test with maximum 70.06% chemosuppression (750 mg/kg). Maximum Mean Survival Time (MST) was 19.2±4.60 and 22.66±4.41 days respectively in the suppressive and curative test, which was extremely statistically significant (p<0.0005) in comparison to untreated control which died by Day 9 post inoculation. Biochemical analysis revealed the safety of ELETF to the hepatic and renal functions of the rodent host. INTERPRETATION & CONCLUSION: The study reports the antiplasmodial potential of Thalictrum foliolosum (ELETF) against Plasmodium berghei infection. The extract can be developed as a phytomedicine against malaria. Alternatively, the active components can be isolated as new lead compounds against the disease.

A new antiviral isoquinoline alkaloid from Thalictrum glandulosissimum / 中国中药杂志

A new isoquinoline alkaloid(1) has been isolated from the whole plant of Thalictrum glandulosissimum by using various chromatographic techniques, including silica gel, sephadex, MCI-gel resin, and RP-HPLC, and its structure was determined as 1-(6-hydroxy-7-methylisoquinolin-1-yl) ethantone by physicochemical properties and spectroscopic data. This compound was evaluated for anti-tobacco mosaic virus(TMV) activity. The results showed that it had prominent anti-TMV activity with inhibition rates of 28.4%. This rate was closed to that of positive control.

Paenibacillus thalictri sp. nov., isolated from surface-sterilized tissue of Thalictrum simplex L.

A Gram-stain-positive, rod-shaped, aerobic, endospore-forming bacterium, designated strain N2SHLJ1T, was isolated from a surface-sterilized tissue sample of Thalictrum simplex L. in Guizhou, PR China. To determine the bacterium's taxonomic position, it was characterized by a polyphasic approach. Phylogenetic analysis based on 16S rRNA gene sequencing suggested that strain N2SHLJ1T belongs to the genus Paenibacillus and is most closely to Paenibacillus aestuarii CJ25T (94.7 % similarity). Strain N2SHLJ1T grew at 10-37 °C (optimum, 30 °C), in 0-2 % (w/v) NaCl (optimum, 0 %) and in pH 5.0-8.0 (optimum, 7.0). The cell-wall peptidoglycan contained meso-diaminopimelic acid and the predominant menaquinone was MK-7. The major fatty acids were anteiso-C15 : 0 and iso-C15 : 0. The polar lipids comprised diphosphatidylglycerol, phosphatidylglycerol, phosphatidylmonomethylethanolamine, phosphatidylethanolamine, an unidentified aminophospholipid, an unidentified phospholipid, an unidentified aminolipid, an unidentified glycolipid and two unidentified lipids. The DNA G+C content was 50.8 mol%. Based on the results of phylogenetic, phenotypic and chemotaxonomic analysis, strain N2SHLJ1T was clearly distinguished from other species with validly published names in the genus Paenibacillus and should therefore be designated as a novel species, for which the name Paenibacillus thalictri sp. nov. is proposed. The type strain is N2SHLJ1T (=JCM 33293T=CGMCC 1.13865T).

Comparison of Anticancer Activity and HPLC-DAD Determination of Selected Isoquinoline Alkaloids from Thalictrum foetidum, Berberis sp. and Chelidonium majus Extracts.

Background: Plants are an important origin of natural substances that the raw material for various pharmaceutical and therapeutic applications due to the presence of phytochemicals, such as alkaloids. Alkaloids, which are found in different plant species, possess numerous biological activities. Some alkaloids have strong cytotoxic effects on various cancer cells. The search for new drugs to treat various cancers is one of the most important challenges of modern scientific research. Objective: This study aimed to investigate of cytotoxic activity of extracts that were obtained from Chelidonium Majus; Berberis sp.; Thalictrum foetidum containing various alkaloids on selected cancer cell lines. The aim was also the quantification of selected alkaloids in the investigated extracts by HPLC. Methods: The analysis of alkaloids contents were performed while using HPLC in reversed phase (RP) mode using Polar RP column and mobile phase containing acetonitrile, water, and ionic liquid. The cytotoxic effect of the tested plant extracts and respective alkaloids' standards were examined while using human pharyngeal squamous carcinoma cells (FaDu), human tongue squamous carcinoma cells (SCC-25), human breast adenocarcinoma cell line (MCF-7), and human triple-negative breast adenocarcinoma cell line (MDA-MB-231). Conclusion: All of the investigated plant extracts possess cytotoxic activity against cancer cell lines: FaDu, SCC-25, MCF-7, and MDA-MB-231. The highest cytotoxic activity against FaDu and MDA-MB-231 cells was observed for Chelidonium majus root extract, while the highest cytotoxic activity against SCC-25 and MCF-7 cells was estimated for the Thalictrum foetidum root extract. There obtained significant differences in the cytotoxic activity of extracts that were obtained from the roots and herbs of Chelidonium majus and Thalictrum foetidum. Based on these results, investigated plant extracts can be recommended for further investigations of anticancer activity.

New aporphine alkaloids with selective cytotoxicity against glioma stem cells from Thalictrum foetidum.

Seven new isoquinoline alkaloids, 9-(2'-formyl-5', 6'-dimethoxyphenoxy)-1, 2, 3, 10-tetramethoxy dehydroaporphine (1), 9-(2'-formyl-5', 6'-dimethoxyphenoxy)-1, 2, 3, 10-tetramethoxy oxoaporphine (2), 3-methoxy-2'-formyl oxohernandalin (3), (-)-9-(2'-methoxycarbonyl-5', 6'-dimethoxyphenoxy)-1, 2, 3, 10-tetramethoxy aporphine (4), (-)-2'-methoxycarbonyl thaliadin (5), (-)-9-(2'-methoxyethyl-5', 6'-dimethoxyphenoxy)-1, 2, 3, 10-tetramethoxy aporphine (6), (-)-3-methoxy hydroxyhernandalinol (7), together with six known isoquinoline alkaloids (8-13) were isolated from the roots of Thalictrum foetidum. Their structures were elucidated by extensive spectroscopic measurements. Compounds 1 and 2 showed significant selective cytotoxicity against glioma stem cells (GSC-3# and GSC-18#) with IC50 values ranging from 2.36 to 5.37 µg·mL-1.