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1.
Molecules ; 29(11)2024 Jun 03.
Article En | MEDLINE | ID: mdl-38893502

Callus cultures of the Iranian medicinal plant Salvia atropatana were initiated from three-week-old seedlings on Murashige and Skoog (MS) medium supplemented with α-naphthaleneacetic acid (NAA) and various cytokinins. Although all tested hormonal variants of the medium and explant enabled callus induction, the most promising growth was noted for N-(2-chloro-4-pyridyl)-N'-phenylurea (CPPU)-induced calli. Three lines obtained on this medium (cotyledon line-CL, hypocotyl line-HL, and root line-RL) were preselected for further studies. Phenolic compounds in the callus tissues were identified using UPLC-MS (ultra-performance liquid chromatography-mass spectrometry) and quantified with HPLC (high-performance liquid chromatography). All lines exhibited intensive growth and contained twelve phenolic acid derivatives, with rosmarinic acid predominating. The cotyledon-derived callus line displayed the highest growth index values and polyphenol content; this was exposed to different light-emitting diodes (LED) for improving biomass accumulation and secondary metabolite yield. Under LED treatments, all callus lines exhibited enhanced RA and total phenolic content compared to fluorescent light, with the highest levels observed for white (48.5-50.2 mg/g dry weight) and blue (51.4-53.9 mg/g dry weight) LEDs. The selected callus demonstrated strong antioxidant potential in vitro based on the 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and ferric reducing antioxidant power (FRAP) tests. Our findings confirm that the S. atropatana callus system is suitable for enhanced rosmarinic acid production; the selected optimized culture provide high-quality plant-derived products.


Polyphenols , Salvia , Polyphenols/metabolism , Salvia/metabolism , Salvia/chemistry , Antioxidants/metabolism , Antioxidants/chemistry , Chromatography, High Pressure Liquid , Cinnamates/metabolism , Cinnamates/chemistry , Rosmarinic Acid , Depsides/metabolism , Cotyledon/metabolism , Cotyledon/chemistry , Naphthaleneacetic Acids/pharmacology , Naphthaleneacetic Acids/chemistry , Naphthaleneacetic Acids/metabolism , Plant Growth Regulators/pharmacology , Plant Growth Regulators/metabolism , Seedlings/metabolism , Seedlings/growth & development , Seedlings/drug effects
2.
J Ethnopharmacol ; 329: 118133, 2024 Jul 15.
Article En | MEDLINE | ID: mdl-38580187

ETHNOPHARMACOLOGICAL RELEVANCE: Angelica roots are a significant source of traditional medicines for various cultures around the northern hemisphere, from indigenous communities in North America to Japan. Among its many applications, the roots are used to treat type 2 diabetes mellitus; however, this application is not mentioned often. Ethnopharmacological studies have reported the use of A. japonica var. hirsutiflora, A. furcijuga, A. shikokiana, and A. keiskei to treat diabetes symptoms, and further reports have demonstrated the three angelica roots, i.e., A. japonica var. hirsutiflora, A. reflexa, and A. dahurica, exhibit insulin secretagogue activity. AIM OF THE STUDY: This study aimed to phytochemically characterize and compare angelica roots monographed in the European Pharmacopeia 11th, isolate major plant metabolites, and assess extracts and isolates' capability to modulate pancreatic ß-cell function. MATERIALS AND METHODS: Root extracts of Angelica archangelica, Angelica dahurica, Angelica biserrata, and Angelica sinensis were phytochemically profiled using liquid chromatography method coupled with mass spectrometry. Based on this analysis, simple and furanocoumarins were isolated using chromatography techniques. Extracts (1.6-50 µg/mL) and isolated compounds (5-40 µmol/L) were studied for their ability to modulate insulin secretion in the rat insulinoma INS-1 pancreatic ß-cell model. Insulin was quantified by the homogeneous time-resolved fluorescence method. RESULTS: Forty-one secondary metabolites, mostly coumarins, were identified in angelica root extracts. A. archangelica, A. dahurica, and A. biserrata root extracts at concentration of 12.5-50 µg/mL potentiated glucose-induced insulin secretion, which correlated with their high coumarin content. Subsequently, 23 coumarins were isolated from these roots and screened using the same protocol. Coumarins substituted with the isoprenyl group were found to be responsible for the extracts' insulinotropic effect. CONCLUSIONS: Insulinotropic effects of three pharmacopeial angelica roots were found, the metabolite profiles and pharmacological activities of the roots were correlated, and key structures responsible for the modulation of pancreatic ß-cell function were identified. These findings may have implications for the traditional use of angelica roots in treating diabetes. Active plant metabolites may also become lead structures in the search for new antidiabetic treatments.


Angelica , Insulin-Secreting Cells , Phytochemicals , Plant Extracts , Plant Roots , Angelica/chemistry , Insulin-Secreting Cells/drug effects , Insulin-Secreting Cells/metabolism , Plant Extracts/pharmacology , Plant Extracts/chemistry , Animals , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Phytochemicals/analysis , Rats , Insulin/metabolism , Insulin Secretion/drug effects , Coumarins/pharmacology , Coumarins/isolation & purification , Hypoglycemic Agents/pharmacology , Hypoglycemic Agents/isolation & purification , Hypoglycemic Agents/chemistry
3.
Int J Mol Sci ; 24(4)2023 Feb 13.
Article En | MEDLINE | ID: mdl-36835169

Inflammation is the first physiological defence mechanism against external and internal stimuli. The prolonged or inappropriate response of the immune system may lead to the persistent inflammatory response that can potentially become a basis for chronic diseases e.g., asthma, type II diabetes or cancer. An important role in the alleviation of inflammatory processes, as an adjunct to traditional pharmacological therapy, is attributed to phytotherapy, especially to raw materials with a long tradition of use, e.g., ash leaves. Despite their long-term use in phytotherapy, the specific mechanisms of action have not been confirmed in a sufficient number of biological or clinical studies. The aim of the study is a detailed phytochemical analysis of infusion and its fractions, isolation of pure compounds from the leaves of Fraxinus excelsior and evaluation of their effect on the secretion of anti-inflammatory cytokines (TNF-α, IL-6) and IL-10 receptor expression in an in vitro model of monocyte/macrophage cells isolated from peripheral blood. Methods: Phytochemical analysis was carried out by the UHPLC-DAD-ESI-MS/MS method. Monocytes/macrophages were isolated from human peripheral blood using density gradient centrifugation on Pancoll. After 24 h incubation with tested fractions/subfractions and pure compounds, cells or their supernatants were studied, respectively, on IL-10 receptor expression by flow cytometry and IL-6, TNF-α, IL-1ß secretion by the ELISA test. Results were presented with respect to Lipopolysaccharide (LPS) control and positive control with dexamethasone. Results: The infusion, 20% and 50% methanolic fractions and their subfractions, as well as their dominating compounds, e.g., ligstroside, formoside and oleoacteoside isolated from the leaves, show the ability to increase the IL-10 receptor expression on the surface of monocyte/macrophage cells, stimulated by LPS, and to decrease the secretion of pro-inflammatory cytokines, e.g., TNF-α, IL-6.


Anti-Inflammatory Agents , Fraxinus , Phytochemicals , Humans , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Cytokines/metabolism , Diabetes Mellitus, Type 2/drug therapy , Fraxinus/chemistry , Fraxinus/metabolism , Interleukin-6 , Lipopolysaccharides , Phytochemicals/chemistry , Phytochemicals/pharmacology , Plant Extracts/pharmacology , Tandem Mass Spectrometry , Tumor Necrosis Factor-alpha/metabolism , Leukocytes, Mononuclear/drug effects , Leukocytes, Mononuclear/metabolism , Macrophages/drug effects , Macrophages/metabolism
4.
Molecules ; 28(2)2023 Jan 04.
Article En | MEDLINE | ID: mdl-36677535

Plants of the genus Pulicaria are known for providing traditional medicines, spices, herbal teas, and insect deterrents. Pulicaria inuloides (Poir.). DC. is one of the less chemically studied species within the genus. Hydroalcoholic extracts from roots and aerial parts of P. inuloides were analyzed using the UHPLC-PAD-MSn technique and revealed the presence of six caffeoylquinic and eleven caffeoylhexaric conjugates together with hydroxykaempferol dimethyl ether and quercetagetin trimethyl ether. Moreover, constituents of chloroform extract from the whole P. inuloides plants were isolated and identified by spectroscopic methods. One new and four known caryophyllene derivatives, three thymol derivatives, and four polymethoxylated flavonols were found in the analyzed extract. The structure of the new compound was established by spectroscopic methods (HRESIMS, 1H NMR, 13C NMR, COSY, HSQC, HMBC, NOESY). The cytotoxicity of 6-Hydroxykaempferol 3,7-dimethyl ether and quercetagetin 3,7,3'-trimethyl ether (chrysosplenol C), which are major flavonols isolated from the plant, were tested on prostate epithelial cells (PNT2), prostate cancer cells (DU145 and PC3), human keratinocytes (HaCaT), and melanoma cells (HTB140 and A375). Both flavonols demonstrated moderate cytotoxic activity against PC3 cells (IC50 = 59.5 µM and 46.6 µM, respectively). The remaining cell lines were less affected (IC50 > 150 µM).


Antineoplastic Agents , Methyl Ethers , Pulicaria , Humans , Flavonols/pharmacology , Pulicaria/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry
5.
Cells ; 11(20)2022 10 21.
Article En | MEDLINE | ID: mdl-36291197

Many species from the Pinaceae family have been recognized as a rich source of lignans, flavonoids, and other polyphenolics. The great common occurrence of conifers in Europe, as well as their use in the wood industry, makes both plant material and industrial waste material easily accessible and inexpensive. This is a promising prognosis for both discovery of new active compounds as well as for finding new applications for wood and its industry waste products. This study aimed to analyze and phytochemically profile 13 wood extracts of the Pinaceae family species, endemic or introduced in Polish flora, using the LC-DAD-ESI-MS/MS method and compare their respective metabolite profiles. Branch wood methanolic extracts were phytochemically profiled. Lignans, stilbenes, flavonoids, diterpenes, procyanidins, and other compounds were detected, with a considerable variety of chemical content among distinct species. Norway spruce (Picea abies (L.) H.Karst.) branch wood was the most abundant source of stilbenes, European larch (Larix decidua Mill.) mostly contained flavonoids, while silver fir (Abies alba Mill.) was rich in lignans. Furthermore, 10 lignans were isolated from the studied material. Our findings confirm that wood industry waste materials, such as conifer branches, can be a potent source of different phytochemicals, with the plant matrix being relatively simple, facilitating future isolation of target compounds.


Lignans , Proanthocyanidins , Stilbenes , Tracheophyta , Proanthocyanidins/analysis , Wood , Tandem Mass Spectrometry/methods , Industrial Waste/analysis , Phytochemicals/chemistry , Flavonoids , Plant Extracts/chemistry
6.
Plants (Basel) ; 11(17)2022 Sep 05.
Article En | MEDLINE | ID: mdl-36079704

Lignans are a group of natural polyphenols present in medicinal plants and in plants which are a part of the human diet for which more and more pharmacological activities, such as antimicrobial, anti-inflammatory, hypoglycemic, and cytoprotective, are being reported. However, it is their cytotoxic activities that are best understood and which have shed light on this group. Two anticancer drugs, etoposide, and teniposide, were derived from a potent cytotoxic agent-podophyllotoxin from the roots of Podophyllum peltatum. The evidence from clinical and observational studies suggests that human microbiota metabolites (enterolactone, enterodiol) of dietary lignans (secoisolariciresinol, pinoresinol, lariciresinol, matairesinol, syringaresinol, medioresinol, and sesamin) are associated with a reduced risk of some hormone-dependent cancers. The biological in vitro, pharmacological in vivo investigations, and clinical studies demand significant amounts of pure compounds, as well as the use of well-defined and standardized extracts. That is why proper extract preparation, optimization of lignan extraction, and identification are crucial steps in the development of lignan use in medicine. This review focuses on lignan extraction, purification, fractionation, separation, and isolation methods, as well as on chromatographic, spectrometric, and spectroscopic techniques for their qualitative and quantitative analysis.

7.
Molecules ; 24(8)2019 Apr 24.
Article En | MEDLINE | ID: mdl-31022860

Carpesium divaricatum Sieb. & Zucc. has a long history of use as both a medicinal and a food plant. However, except for terpenoids, its chemical constituents have remained poorly investigated. The composition of hydroalcoholic extract from aerial parts of C. divaricatum was analyzed by HPLC-DAD-MSn, revealing the presence of numerous caffeic acid derivatives that were formerly unknown constituents of the plant. In all, 17 compounds, including commonly found chlorogenic acids and rarely occurring butyryl and methylbutyryl tricaffeoylhexaric acids, were tentatively identified. Fractionation of lipophilic extract from cultivated shoots led to the isolation of 12-oxo-phytodienoic acid (12-OPDA), which is a newly identified constituent of the plant. The compound, at concentrations of 0.5, 1.0, and 2.5 µM, significantly reduced IL-8, IL-1ß, TNFα, and CCL2 excretion by lipopolysaccharide (LPS)-stimulated human neutrophils. Reactive oxygen species (ROS) production induced by f-MLP was also significantly diminished in the neutrophils pretreated by 12-OPDA. The newly identified constituents of the plant seem to be partly responsible for its pharmacological activity and elevate the value of C. divaricatum as a potential functional food.


Asteraceae/chemistry , Caffeic Acids/chemistry , Chlorogenic Acid/chemistry , Fatty Acids, Unsaturated/chemistry , Caffeic Acids/isolation & purification , Caffeic Acids/pharmacology , Chemokine CCL2/genetics , Chlorogenic Acid/isolation & purification , Chromatography, High Pressure Liquid , Fatty Acids, Unsaturated/isolation & purification , Fatty Acids, Unsaturated/pharmacology , Gene Expression Regulation/drug effects , Humans , Interleukin-8/genetics , Lipopolysaccharides/pharmacology , Neutrophils/drug effects , Plant Components, Aerial/chemistry , Plant Shoots/chemistry , Reactive Oxygen Species/chemistry , Tumor Necrosis Factor-alpha/genetics
8.
Nat Prod Res ; 26(17): 1584-93, 2012.
Article En | MEDLINE | ID: mdl-22085305

Taking into account the role of reactive oxygen species in the development of inflammation, and the application of the plants of genus Galinsoga Ruiz & Pav. in folk medicines for inflammatory states, we investigated and compared the antioxidant activities of particular Galinsoga extracts and fractions. The compositions of the most active fractions were studied using thin layer chromatography (TLC) and high-performance liquid chromatography (HPLC) methods. The extracts and fractions from Galinsoga parviflora Cav. and Galinsoga quadriradiata Ruiz et Pav. possess dose-dependent free radical-scavenging ability against DPPH• and superoxide radicals, as well as inhibitory effects on linoleic acid peroxidation in a manner comparable to gallic acid. In the most active fractions, flavonoids, patulitrin, quercimeritrin, quercitagetrin and caffeoyl derivatives were detected. Our research demonstrates that the investigated herbs are an interesting source of preparations with significant antioxidant effects. Our results justify the use of both raw materials in inflammatory diseases, among others, due to their ability to prevent free radical-induced deleterious effects.


Antioxidants/chemistry , Asteraceae/chemistry , Chromatography, High Pressure Liquid/methods , Chromatography, Thin Layer/methods
9.
Acta Pharm ; 60(1): 119-28, 2010 Mar.
Article En | MEDLINE | ID: mdl-20228046

Acetylcholinesterase (AChE) inhibitors are widely used for the symptomatic treatment of Alzheimer's disease (AD) to enhance central cholinergic transmission. On the other hand, butyrylcholinesterase (BuChE) inhibitors were reported to produce a significant increase in brain extracellular AChE without triggering severe peripheral or central side effects. In the present study, we selected twelve plants used in traditional European medicine to treat different central nervous system (CNS) disorders or to improve memory. Methanolic and hexane extracts of these plants were tested for the AChE and BuChE inhibitory activity using Ellman's colorimetric method. The most potent AChE and BuChE inhibition was observed in the hexane extracts of the flowers of Arnica chamissonis Less. subs. foliosa and Ruta graveolens L. herb at a concentration of 400 microg mL(-1). However, methanolic extracts of the flowers of Arnica chamissonis Less. subs. foliosa and the Hypericum perforatum L. herb demonstrated at the same concentration, selective inhibition only against AChE but not against BuChE. The other extracts did not show any significant AChE or BuChE inhibitory activity. Our results show that further investigations of the extracts of arnica, rue and St. John's Wort are needed to identity the compounds responsible for the AChE and BuChE inhibitory activity.


Acetylcholinesterase , Butyrylcholinesterase , Cholinesterase Inhibitors/pharmacology , Medicine, Traditional , Plant Extracts/pharmacology , Acetylcholinesterase/metabolism , Animals , Butyrylcholinesterase/metabolism , Cattle , Cholinesterase Inhibitors/chemistry , Drug Evaluation, Preclinical/methods , Electrophorus , Europe , Horses , Medicine, Traditional/methods , Plant Extracts/chemistry , Plant Preparations/chemistry , Plant Preparations/pharmacology
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