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1.
Biomed Pharmacother ; 176: 116851, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38838506

ABSTRACT

Glinus oppositifolius L., a member of the Molluginaceae family, has a long-standing history of utilization as both a vegetable and a medicinal agent across numerous countries. This plant possesses a diverse range of pharmacological activities and attracts scientific interest in studying its chemical profile. The present phytochemical investigation of the plant resulted in the isolation of eleven new triterpenoid saponins, accompanied by three known compounds. Their structures were elucidated by intensive spectroscopic analysis, DFT calculations, and comparison with previously reported data. The isolates were evaluated for their anti-adipogenic effect and cytotoxicity against human cancer cell lines, namely, colorectal carcinoma HCT116, hepatoblastoma cell HepG2, breast cancer cell MDA-MB-231, and human lung adenocarcinoma cell A549. Compounds 5, 7, and 13 exhibited a potent inhibitory effect against the differentiation of preadipocyte 3T3-L1. In addition, compound 13 displayed inhibitory effects against the growth of A549 cancer cells.


Subject(s)
3T3-L1 Cells , Plant Components, Aerial , Saponins , Triterpenes , Saponins/pharmacology , Saponins/isolation & purification , Saponins/chemistry , Humans , Triterpenes/pharmacology , Triterpenes/isolation & purification , Triterpenes/chemistry , Animals , Mice , Plant Components, Aerial/chemistry , Adipogenesis/drug effects , A549 Cells , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Hep G2 Cells , Cell Line, Tumor , Plant Extracts/pharmacology , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Cell Differentiation/drug effects , HCT116 Cells
2.
Molecules ; 29(10)2024 May 15.
Article in English | MEDLINE | ID: mdl-38792176

ABSTRACT

Utilizing online gradient pressure liquid extraction (OGPLE) coupled with a high-performance liquid chromatography antioxidant analysis system, we examined the antioxidative active components present in both the aerial parts and roots of dandelion. By optimizing the chromatographic conditions, we identified the ferric reducing-antioxidant power system as the most suitable for online antioxidant reactions in dandelion. Compared to offline ultrasonic extraction, the OGPLE method demonstrated superior efficiency in extracting chemical components with varying polarities from the samples. Liquid chromatography-mass spectrometry revealed twelve compounds within the dandelion samples, with nine demonstrating considerable antioxidant efficacy. Of these, the aerial parts and roots of dandelion contained nine and four antioxidant constituents, respectively. Additionally, molecular docking studies were carried out to investigate the interaction between these nine antioxidants and four proteins associated with oxidative stress (glutathione peroxidase, inducible nitric oxide synthase, superoxide dismutase, and xanthine oxidase). The nine antioxidant compounds displayed notable binding affinities below -5.0 kcal/mol with the selected proteins, suggesting potential receptor-ligand interactions. These findings contribute to enhancing our understanding of dandelion and provide a comprehensive methodology for screening the natural antioxidant components from herbs.


Subject(s)
Antioxidants , Molecular Docking Simulation , Plant Extracts , Taraxacum , Antioxidants/chemistry , Chromatography, High Pressure Liquid/methods , Taraxacum/chemistry , Plant Extracts/chemistry , Plant Roots/chemistry , Plant Components, Aerial/chemistry
3.
Phytochemistry ; 224: 114145, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38759829

ABSTRACT

Eleven previously undescribed abietane-type diterpenoids, named caryopincanoids A-K (1-11), together with five known compounds, were isolated from the EtOH extract of the aerial parts of Caryopteris incana (Thunb.) Miq. Their structures were elucidated on the basis of comprehensive spectroscopic data, NMR calculations, and ECD calculations. The inhibitory activities of all compounds against HIF-2α gene expression in 786-O cells were tested by luciferase assay. Compounds 7, 9, 15, and 16 showed significant inhibitory effects with IC50 values ranging from 12.73 to 23.80 µM. The preliminary structure-activity relationship of these compounds was also discussed.


Subject(s)
Abietanes , Basic Helix-Loop-Helix Transcription Factors , Abietanes/chemistry , Abietanes/pharmacology , Abietanes/isolation & purification , Structure-Activity Relationship , Humans , Basic Helix-Loop-Helix Transcription Factors/antagonists & inhibitors , Basic Helix-Loop-Helix Transcription Factors/metabolism , Molecular Structure , Plant Components, Aerial/chemistry , Dose-Response Relationship, Drug
4.
Fitoterapia ; 176: 106034, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38795853

ABSTRACT

Ten diterpenoids including six unreported abietane-type diterpenoids Glecholmenes A-F (1-6) and an undescribed labdane-type diterpenoid Glecholmene G (9), together with three known diterpenoids (7,8,10), were firstly isolated from the aerial part of G. longituba. Their structures were established mainly by nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) methods. Electronic circular dichroism (ECD) calculations and X-ray crystallographic analyses were used for the determination of their absolute configurations. The anti-inflammatory activity of all compounds was evaluated using the classical LPS-induced NO release model in RAW264.7 cells. Compound 2 displayed significant anti-inflammatory activities with IC50 values of 29.08 ± 1.40 µM (Aminoguanidine hydrochloride as the positive control, IC50 = 21.84 ± 0.48 µM).


Subject(s)
Anti-Inflammatory Agents , Diterpenes , Phytochemicals , Plant Components, Aerial , Animals , Mice , Plant Components, Aerial/chemistry , Molecular Structure , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/isolation & purification , RAW 264.7 Cells , Diterpenes/pharmacology , Diterpenes/isolation & purification , Diterpenes/chemistry , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Nitric Oxide/metabolism , Abietanes/pharmacology , Abietanes/isolation & purification , Lamiaceae/chemistry , China
5.
Fitoterapia ; 176: 106042, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38801898

ABSTRACT

Thymus daenensis Celak (Lamiaceae family), known as denaian thyme, is an Iranian endemic plant, commonly used for its carminative, expectorant, antibacterial and antifungal properties. Previous studies report the chemical profile of the essential oil of T. daenensis aerial parts, but little is known about its non volatile constituents. Herein, phytochemical and biological investigation of the polar extract of T. daenensis aerial parts to provide further insight into traditional use of this plant has been accomplished. High-performance liquid chromatography coupled to linear ion-trap and orbitrap high-resolution mass spectrometry (LC-ESI/LTQOrbitrap/MS/MS) analysis of MeOH extract was performed to guide the isolation of specialized metabolites and successive characterization by NMR analysis. MeOH extract displayed antioxidant activity evaluated by DPPH (EC50 = 48.99 ± 1.47 µg/mL) and TEAC assay (1.37 mg/mL). Successively, the biofilm inhibitory activity of extract and isolated compounds against mature biofilms of Escherichia coli, Pseudomonas aeruginosa, Acinetobacter baumannii, Listeria monocytogenes, and Staphylococcus aureus, and their influence on the metabolism of sessile bacterial cells were evaluated. Two previously unreported thymol derivatives have been identified. The biofilm inhibitory activity of isolated compounds highlighted a promising antimicrobial action for the tested compounds. In particular, vanillic acid, (3S,5R,6R,7E,9S)-megastigm-7-ene-3,5,6,9-tetrol 3-O-ß-D-glucopyranoside, thymoquinol-2-O-ß-D-glucopyranoside and the never reported compound daenol resulted capable of exerting inhibitory activity vs all pathogenic strains. All compounds tested at a concentration of 10 µg/mL inhibited the metabolism of the sessile cells of E. coli at a percentage ranging between 37.7% and 77.39%, and of L.monocytogenes at a percentage ranging between 21.79% and 71.17%.


Subject(s)
Antioxidants , Phytochemicals , Plant Components, Aerial , Plant Extracts , Thymus Plant , Thymus Plant/chemistry , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Iran , Plant Extracts/pharmacology , Plant Extracts/chemistry , Antioxidants/pharmacology , Antioxidants/isolation & purification , Plant Components, Aerial/chemistry , Biofilms/drug effects , Plants, Medicinal/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/chemistry , Molecular Structure , Microbial Sensitivity Tests
6.
Nat Prod Res ; 38(11): 1918-1923, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38739564

ABSTRACT

Blumea eriantha D.C is a weed from Asteraceae family and is reported to have anticancer activity. The essential oil from the aerial parts was extracted by steam distillation method with the yield of 0.36%. Through GC-MS analysis of the oil, seventeen compounds could be identified by comparing with linear retention indices with the library. Out of the seventeen compounds ß-Caryophylline oxide was isolated by column chromatography with gradient elution and the structure was determined through FT-IR, MS, 1HNMR, 13 C NMR and DEPT. The oil was evaluated for its effect on angiogenesis using Chorioallantoic Membrane Assay (CAM Assay). The concentration dependent antiangiogenic effect was observed with IC 50 value of 19.28 ppm.


Subject(s)
Angiogenesis Inhibitors , Asteraceae , Gas Chromatography-Mass Spectrometry , Oils, Volatile , Oils, Volatile/chemistry , Oils, Volatile/pharmacology , Angiogenesis Inhibitors/pharmacology , Angiogenesis Inhibitors/chemistry , Asteraceae/chemistry , Animals , Chorioallantoic Membrane/drug effects , Chorioallantoic Membrane/blood supply , Plant Components, Aerial/chemistry , Sesquiterpenes/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Molecular Structure , Spectroscopy, Fourier Transform Infrared , Polycyclic Sesquiterpenes
7.
Pak J Pharm Sci ; 37(1): 163-171, 2024 Jan.
Article in English | MEDLINE | ID: mdl-38741413

ABSTRACT

Medicinal plants contain a wide variety of bioactive phytoconstituents which can serve as new therapeutic agents for several diseases. This study examines the antidiabetic potential of Aitchisonia rosea in alloxan-induced diabetic rats and identifies its bioactive phytoconstituents using GC-MS. In vitro, antidiabetic potential was established using the α-amylase inhibition assay. In vivo, antidiabetic potential was investigated by employing the oral glucose tolerance test (OGTT). GC-MS analysis was used to identify the bioactive phytoconstituents. The in vitro and in vivo tests showed that the aqueous extract of A. rosea possesses better antidiabetic potential. The α-amylase inhibition assay highlighted an IC50 value of 134.87µg/ml. In an oral glucose tolerance test, rats given an aqueous A. rosea extract significantly lowered their blood sugar levels significant reduction in the blood glucose concentration was observed in the oral glucose tolerance test in rats treated with the aqueous A. rosea extract. GC-MS investigation revealed many phytoconstituents, with serverogenin acetate and cycloheptasiloxane tetradecamethyl being important antidiabetic agents. This study found anti-diabetic properties in A. rosea extract. The phytochemical and GC-MS investigation also found serverogenin acetate and cycloheptasiloxane tetradecamethyl, which could be used to develop new antidiabetic drugs.


Subject(s)
Blood Glucose , Diabetes Mellitus, Experimental , Gas Chromatography-Mass Spectrometry , Hypoglycemic Agents , Plant Components, Aerial , Plant Extracts , Animals , Hypoglycemic Agents/pharmacology , Hypoglycemic Agents/isolation & purification , Hypoglycemic Agents/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Diabetes Mellitus, Experimental/drug therapy , Diabetes Mellitus, Experimental/blood , Diabetes Mellitus, Experimental/chemically induced , Plant Components, Aerial/chemistry , Male , Blood Glucose/drug effects , Rats , Glucose Tolerance Test , alpha-Amylases/antagonists & inhibitors , alpha-Amylases/metabolism , Rats, Wistar , Phytochemicals/pharmacology , Phytochemicals/analysis , Alloxan
8.
Fitoterapia ; 175: 105951, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38583637

ABSTRACT

Four undescribed amide alkaloids hongkongensines A-C and 1-(1-oxo-6-hydroxy-2E,4E-dodecadienyl)-piperidine, five known amide alkaloids, and three known neolignans were isolated from the aerial part of Piper hongkongense. The planar structures of these compounds were determined by detailed analyses of HR-ESI-MS and NMR data. The absolute configurations of hongkongensines A-C were elucidated by single-crystal X-ray diffraction analysis and ECD calculations. Moreover, the inhibitory activities of PCSK9 expression in vitro for all compounds were assessed by PCSK9 AlphaLISA screening. Kadsurenone (10) displayed a significant inhibitory activity at 5 µM with an inhibition rate of 51.98%, compared with 55.55% of berberine (BBR 5 µM).


Subject(s)
Alkaloids , Lignans , PCSK9 Inhibitors , Phytochemicals , Piper , Plant Components, Aerial , Piper/chemistry , Molecular Structure , Alkaloids/pharmacology , Alkaloids/isolation & purification , Alkaloids/chemistry , Lignans/pharmacology , Lignans/isolation & purification , Humans , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Plant Components, Aerial/chemistry , Amides/pharmacology , Amides/isolation & purification , Amides/chemistry , Proprotein Convertase 9/metabolism , China
9.
J Ethnopharmacol ; 331: 118271, 2024 Sep 15.
Article in English | MEDLINE | ID: mdl-38688356

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: The use of medicinal plants for central nervous system (CNS)-related ailments, such as epilepsy and anxiety, is prevalent in South Africa. Plants from the Lamiaceae family are commonly used for their therapeutic benefits. Leonotis leonurus (L.) R.Br. has been reported in ethnobotanical literature to have anticonvulsant and anxiolytic effects through the inhalation of pyrolysis products obtained by combustion of the aerial parts. AIM AND OBJECTIVES: To explore the chemical profiles and CNS activity of the smoke extract and isolated constituents of L. leonurus in zebrafish larvae, through anticonvulsive and anxiolytic activity assays. MATERIALS AND METHODS: The smoke extract of L. leonurus was obtained through the combustion of the aerial parts of the plant using a custom-built smoke recovery apparatus. The chemical profile of the smoke constituents was determined using Ultra-Performance Liquid Chromatography coupled with Mass Spectrometry (UPLC-MS). Targeted compounds were subjected to preparative High-Performance Liquid Chromatography for separation before structure elucidation using Nuclear Magnetic Resonance (NMR). The maximum tolerated concentrations, as well as the anxiolytic activity of the smoke extract were determined in five days post fertilisation zebrafish larvae. Reverse-thigmotaxis and locomotor activity of larvae in the light/dark transition assay were used to determine anxiolytic activity. Zebrafish larvae at six days post fertilisation (dpf) were subjected to several concentrations of the smoke constituents of L. leonurus. The baseline locomotor activity of the larvae was tracked for 30 min, prior to addition of pentylenetetrazole (PTZ) to induce seizure-like behaviour in the larvae, after which the locomotor activity of the larvae was once again tracked for an additional 30 min. RESULTS: The UPLC-MS profiles of the smoke extract revealed the presence of two main compounds, leoleorin A and leoleorin B, which were targeted and isolated. Upon subjection to NMR spectroscopy for structure elucidation, the compounds were confirmed to be labdane diterpenoids. Both leoleorin A and leoleorin B, and the smoke extract displayed suppression of the PTZ induced seizure-like behaviour in zebrafish larvae. Under light and dark conditions, the smoke extract and compounds displayed potential anxiolytic activity at different concentrations. CONCLUSION: Our results suggest that the smoke constituents of L. leonurus may exert anticonvulsant and anxiolytic effects which align with the traditional indications and the mode of administration.


Subject(s)
Anti-Anxiety Agents , Anticonvulsants , Plant Extracts , Seizures , Smoke , Zebrafish , Animals , Anti-Anxiety Agents/pharmacology , Anti-Anxiety Agents/isolation & purification , Anti-Anxiety Agents/chemistry , Smoke/adverse effects , Plant Extracts/pharmacology , Plant Extracts/chemistry , Anticonvulsants/pharmacology , Anticonvulsants/isolation & purification , Seizures/drug therapy , Seizures/chemically induced , Larva/drug effects , Lamiaceae/chemistry , Pentylenetetrazole , Plant Components, Aerial/chemistry , South Africa , Behavior, Animal/drug effects
10.
Chem Biodivers ; 21(6): e202400399, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38634752

ABSTRACT

Four undescribed prenylated flavonoids, sophoratones A-D (1-4), and 17 known flavonoids, were obtained from the aerial parts of Sophora tonkinensis. Their structures with absolute configurations were elucidated by detailed interpretation of NMR spectroscopy, mass spectrometry, and ECD calculations. Meanwhile, the ability of these compounds to inhibit the release of nitric oxide (NO) by a lipopolysaccharide induced mouse in RAW 264.7 cells was assayed. The results indicated that some compounds exhibited clear inhibitory effects, with IC50 ranging from 19.91±1.08 to 35.72±2.92 µM. These results suggest that prenylated flavonoids from the aerial parts of S. tonkinensis could potentially be used as a latent source of anti-inflammatory agents.


Subject(s)
Flavonoids , Lipopolysaccharides , Nitric Oxide , Plant Components, Aerial , Sophora , Sophora/chemistry , Animals , Mice , Flavonoids/pharmacology , Flavonoids/isolation & purification , Flavonoids/chemistry , RAW 264.7 Cells , Plant Components, Aerial/chemistry , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/metabolism , Nitric Oxide/biosynthesis , Lipopolysaccharides/pharmacology , Lipopolysaccharides/antagonists & inhibitors , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Structure-Activity Relationship , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Molecular Structure , Dose-Response Relationship, Drug , Cell Survival/drug effects
11.
Biomolecules ; 14(4)2024 Apr 11.
Article in English | MEDLINE | ID: mdl-38672484

ABSTRACT

A detailed phytochemical investigation has been carried out on the aerial parts of G. foetida leading to the isolation of 29 pure compounds, mainly belonging to the amorfrutin and polyphenol classes. Among them, the new amorfrutin N (5) and exiguaflavone L (21) were isolated and their structures elucidated by means of HR-ESIMS and NMR. All the isolated compounds were investigated for modulation of mitochondrial activity and stimulation of glucose uptake via GLUT transporters, two metabolic processes involved in intracellular glucose homeostasis, which, therefore, correlate with the incidence of metabolic syndrome. These experiments revealed that amorfrutins were active on both targets, with amorfrutin M (17) and decarboxyamorfrutin A (2) emerging as mitochondrial stimulators, and amorfrutin 2 (12) as a glucose uptake promoter. However, members of the rich chalcone/flavonoid fraction also proved to contribute to this activity.


Subject(s)
Glucose , Metabolic Syndrome , Plant Components, Aerial , Metabolic Syndrome/metabolism , Metabolic Syndrome/drug therapy , Plant Components, Aerial/chemistry , Humans , Glucose/metabolism , Glycyrrhiza/chemistry , Mitochondria/metabolism , Mitochondria/drug effects , Plant Extracts/pharmacology , Plant Extracts/chemistry , Flavonoids/chemistry , Flavonoids/pharmacology , Flavonoids/isolation & purification , Glucose Transport Proteins, Facilitative/metabolism , Glucose Transport Proteins, Facilitative/genetics
12.
Chin J Nat Med ; 22(4): 375-384, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38658100

ABSTRACT

The aerial parts of Mosla chinensis Maxim. and Mosla chinensis cv. 'Jiangxiangru' (MCJ) are widely utilized in traditional Chinese medicine (TCM), known collectively as Xiang-ru. However, due to clinical effectiveness concerns and frequent misidentification, the original plants have increasingly been substituted by various species within the genera Elsholtzia and Mosla. The challenge in distinguishing between these genera arises from their similar morphological and metabolic profiles. To address this issue, our study introduced a rapid method for metabolic characterization, employing high-resolution mass spectrometry-based metabolomics. Through detailed biosynthetic and chemometric analyses, we pinpointed five phenolic compounds-salviaflaside, cynaroside, scutellarein-7-O-D-glucoside, rutin, and vicenin-2-among 203 identified compounds, as reliable chemical markers for distinguishing Xiang-ru from closely related Elsholtzia species. This methodology holds promise for broad application in the analysis of plant aerial parts, especially in verifying the authenticity of aromatic traditional medicinal plants. Our findings underscore the importance of non-volatile compounds as dependable chemical markers in the authentication process of aromatic traditional medicinal plants.


Subject(s)
Drugs, Chinese Herbal , Lamiaceae , Phenols , Phenols/analysis , Phenols/chemistry , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/analysis , Lamiaceae/chemistry , Lamiaceae/classification , Medicine, Chinese Traditional , Metabolomics/methods , Mass Spectrometry/methods , Plant Components, Aerial/chemistry
13.
Fitoterapia ; 175: 105954, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38583638

ABSTRACT

Six previously undescribed diterpenoid glucosides, along with four known compounds, were isolated from the aerial parts of Sigesbeckia glabrescens. The structures and absolute configurations of undescribed compounds were elucidated using extensive spectroscopic techniques, ECD calculations and chemical methods. Compounds 1 and 8 exhibited anti-inflammatory activity against LPS-induced NO production in RAW 264.7 macrophages, with compound 8 demonstrating significant inhibitory activity compared to positive control minocycline, boasting an IC50 value at 14.20 µM.


Subject(s)
Anti-Inflammatory Agents , Diterpenes , Glucosides , Nitric Oxide , Phytochemicals , Plant Components, Aerial , Animals , RAW 264.7 Cells , Mice , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/isolation & purification , Molecular Structure , Glucosides/pharmacology , Glucosides/isolation & purification , Diterpenes/pharmacology , Diterpenes/isolation & purification , Nitric Oxide/metabolism , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Plant Components, Aerial/chemistry , China , Macrophages/drug effects , Asteraceae/chemistry , Sigesbeckia
14.
Fitoterapia ; 175: 105948, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38588904

ABSTRACT

Four new undescribed halimane- and labdane-type diterpenoids, named zeylleucapenoids E-H (1-4), along with four known analogues (5-8), were isolated from the aerial parts of Leucas zeylanica (L.) R. Br. Their structures were determined by comprehensive spectroscopic analysis and computational calculations. Compounds 1 and 2 are the highly modified halimane diterpenoids featuring a 6/6/6-fused tricyclic system with an unusual six-membered 6,11-ether ring. Compound 8 exhibits nontoxic effects for zebrafish embryo, while it displays efficient reduction against NO production in a dose-dependent manner and strongly suppresses the secretion of LPS-induced TNF-α and IL-6 cytokines in RAW264.7 macrophages. In addition, marked reductions of iNOS and COX-2 expression were observed. Molecular docking analysis indicated that 8 has high affinities with the target amino acid residues on protein-binding sites, which may be a possible mechanism contributing to the anti-inflammatory potential of this molecule.


Subject(s)
Anti-Inflammatory Agents , Diterpenes , Molecular Docking Simulation , Plant Components, Aerial , Zebrafish , Animals , Mice , RAW 264.7 Cells , Plant Components, Aerial/chemistry , Molecular Structure , Diterpenes/pharmacology , Diterpenes/isolation & purification , Diterpenes/chemistry , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/chemistry , Fabaceae/chemistry , Nitric Oxide/metabolism , Cyclooxygenase 2/metabolism , Nitric Oxide Synthase Type II/metabolism , Tumor Necrosis Factor-alpha/metabolism , China , Interleukin-6/metabolism , Phytochemicals/pharmacology , Phytochemicals/isolation & purification
15.
J Ethnopharmacol ; 330: 118252, 2024 Aug 10.
Article in English | MEDLINE | ID: mdl-38663782

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: Atractylis aristata batt., as an endemic plant from the Asteraceae family, holds a significant position in the Ahaggar region of southern Algeria's traditional medicine. The aerial parts of Atractylis aristata was used to cure inflammation, fever, and stomach disorders. AIM OF THE STUDY: The objective of the present investigation was to ascertain the overall bioactive components and phytochemical components and examine the antioxidant, antidiabetic, anti-inflammatory, acute toxicity, and sedative properties of the crude extract obtained from the aerial portions of Atractylis aristata (AaME). MATERIALS AND METHODS: The AaME's antioxidant activity was assessed by the use of pyrogallol autoxidation, (1,1 diphenyl-2-picrylhydrazyl) (DPPH), 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), and reducing power (RP) techniques. 1 mg/mL of AaME was used to evaluate the antidiabetic activity by applying the enzyme α-amylase inhibitory power test. At the same time, the bovine serum albumin (BSA) denaturation method was employed to quantify the in vitro anti-inflammatory activity at different concentrations (1.5625, 0.78125, 0.390625, 0.1953125 and 0.09765625 mg/mL). In contrast, following the Organization for Economic Co-operation and Development (OECD) guideline No. 423, which covers acute oral toxicity testing protocols, the limit dosage test was employed to assess in vivo acute toxicity. At the dose of 0.08 mg/mL, the carrageenan-induced paw edema approach was used to assess the anti-inflammatory efficacy in vivo, and the sedative activity was carried out at the dose of 0.08 mg/mL using the measurement of the locomotor method. Different bioactive compounds were identified within AaME using LC-MS/MS and HPLC-UV analysis. RESULTS: The acute toxicity study showed no fatalities or noticeable neurobehavioral consequences at the limit test; this led to their classification in Globally Harmonized System (GHS) category Five, as the OECD guideline No 423 recommended. At a concentration of 0.08 mg/mL (2000 mg/kg), AaME showed apparent inhibition of paw edema and a significant (p = 0.01227) reduction in locomotor activity compared to the control animals. Our findings showed that AaME exhibited considerable antioxidant (IC50 = 0.040 ± 0.003 mg/mL (DPPH), IC50 = 0.005 ± 5.77 × 10-5 mg/mL (ABTS), AEAC = 91.15 ± 3.921 mg (RP) and IR% = 23.81 ± 4.276 (Inhibition rate of pyrogallol) and rebuts antidiabetic activities (I% = 57.6241% ± 2.81772). Our findings revealed that the maximum percentage of BSA inhibition (70.84 ± 0.10%) was obtained at 1.562.5 mg/mL. Thus, the AaME phytochemical profile performed using phytochemical screening, HPLC-UV, and LC-MS/MS analysis demonstrated that A. aristata can be a valuable source of chemicals with biological activity for pharmaceutical manufacturers. CONCLUSION: The phytochemical profiling, determined through HPLC-UV and LC-MS/MS applications, reveals this plant's therapeutic value. The aerial parts of Atractylis aristata contain bioactive molecules such as gallic acid, ascorbic acid, and quercetin, contributing to its significant antioxidant capabilities. Furthermore, identifying alizarin, the active compound responsible for its anti-inflammatory properties, could provide evidence supporting the anti-inflammatory capabilities of this subspecies.


Subject(s)
Anti-Inflammatory Agents , Antioxidants , Hypnotics and Sedatives , Hypoglycemic Agents , Phenols , Plant Extracts , Animals , Antioxidants/pharmacology , Antioxidants/isolation & purification , Antioxidants/chemistry , Hypoglycemic Agents/pharmacology , Hypoglycemic Agents/isolation & purification , Hypoglycemic Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Plant Extracts/toxicity , Male , Phenols/pharmacology , Phenols/analysis , Phenols/isolation & purification , Hypnotics and Sedatives/pharmacology , Hypnotics and Sedatives/isolation & purification , Hypnotics and Sedatives/toxicity , Mice , Asteraceae/chemistry , Rats, Wistar , Rats , Edema/drug therapy , Edema/chemically induced , Female , Plant Components, Aerial/chemistry
16.
J Asian Nat Prod Res ; 26(7): 788-794, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38469737

ABSTRACT

Two previously undescribed iridoid glycosides, 6'-O-trans-feruloyl-(4S,6R)-3,4-dihydro-3ß-ethoxypaederoside (1) and 6'-O-trans-caffeoyl-(4S,6R)-3,4-dihydro-2'-O-3α-paederoside (2), were isolated from the 90% EtOH extract of the air dried aerial parts of Paederia Foetida. Structural elucidation of all the compounds was performed by spectral methods such as 1D and 2D (1H-1H COSY, HMQC, and HMBC) NMR spectroscopy. The two isolated iridoid glycosides were tested in vivo for their antinociceptive properties. As a result, 2 showed potent antinociceptive effect and its ID50 value (53.4 µmol/kg) was 2-fold less than those of the positive control drugs aspirin and acetaminophen.


Subject(s)
Analgesics , Iridoid Glycosides , Plant Components, Aerial , Molecular Structure , Animals , Analgesics/chemistry , Analgesics/pharmacology , Analgesics/isolation & purification , Iridoid Glycosides/pharmacology , Iridoid Glycosides/chemistry , Iridoid Glycosides/isolation & purification , Plant Components, Aerial/chemistry , Mice , Nuclear Magnetic Resonance, Biomolecular , Acetaminophen , Aspirin/pharmacology , Aspirin/chemistry , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Drugs, Chinese Herbal/isolation & purification , Male , Stereoisomerism
17.
Fitoterapia ; 175: 105894, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38461867

ABSTRACT

Thrombosis is currently among the major causes of morbidity and mortality in the World. New prevention and therapy alternatives have been increasingly sought in medicinal plants. In this context, we have been investigating parsley, Petroselinum crispum (Mill.) Nym, an aromatic herb with two leaf varieties. We report here the in vitro, in vivo, and ex vivo anti-hemostatic and antithrombotic activities of a parsley curly-leaf variety. Aqueous extracts of aerial parts (PCC-AP), stems (PCC-S), and leaves (PCC-L) showed significant in vitro antiplatelet activity. PCC-AP extract exhibited the highest activity (IC50 2.92 mg/mL) when using ADP and collagen as agonists. All extracts also presented in vitro anticoagulant activity (APTT and PT) and anti-thrombogenic activity. PCC-S was the most active, with more significant interference in the factors of the intrinsic coagulation pathway. The oral administration of PCC-AP extract in rats caused a greater inhibitory activity in the deep vein thrombi (50%; 65 mg/kg) than in arterial thrombi formation (50%; 200 mg/kg), without cumulative effect after consecutive five-day administration. PCC-AP extract was safe in the induced bleeding time test. Its anti-aggregating profile was similar in ex vivo and in vitro conditions but was more effective in the extrinsic pathway when compared to in vitro results. Apiin and coumaric acid derivatives are the main compounds in PCC-AP according to the HPLC-DAD-ESI-MS/MS profile. We demonstrated for the first time that extracts from different parts of curly parsley have significant antiplatelet, anticoagulant, and antithrombotic activity without inducing hemorrhage, proving its potential as a source of antithrombotic compounds.


Subject(s)
Fibrinolytic Agents , Petroselinum , Plant Extracts , Plant Leaves , Animals , Petroselinum/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Plant Leaves/chemistry , Rats , Male , Fibrinolytic Agents/pharmacology , Fibrinolytic Agents/isolation & purification , Fibrinolytic Agents/chemistry , Rats, Wistar , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Thrombosis/drug therapy , Platelet Aggregation Inhibitors/pharmacology , Platelet Aggregation Inhibitors/isolation & purification , Plant Components, Aerial/chemistry , Plant Stems/chemistry , Hemostatics/pharmacology , Hemostatics/isolation & purification , Anticoagulants/pharmacology , Anticoagulants/isolation & purification , Anticoagulants/chemistry , Plants, Medicinal/chemistry
18.
Fitoterapia ; 175: 105903, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38479620

ABSTRACT

A phytochemical study of the aerial parts of Piper mutabile C. DC. revealed seven undescribed compounds [two (2-7')-neolignans and five polyoxygenated cyclohexene glycosides] and six known propenylcatechol derivatives. The chemical structures of the isolated compounds were elucidated by extensive HR-ESI-MS and NMR analyses, as well as comparison with the literature. The absolute configurations of the (2-7')-neolignans were confirmed by GIAO 13C NMR calculations with a sorted training set strategy and TD-DFT calculation ECD spectra. The (2-7')-neolignans and polyoxygenated cyclohexene glycosides are unusual in natural sources. Undescribed neolignans 1 and 2 inhibited NO production in RAW 264.7 cells, with respective IC50 values of 14.4 and 9.5 µM.


Subject(s)
Cyclohexenes , Glycosides , Lignans , Nitric Oxide , Phytochemicals , Piper , Plant Components, Aerial , Nitric Oxide/biosynthesis , Nitric Oxide/metabolism , Nitric Oxide/antagonists & inhibitors , RAW 264.7 Cells , Mice , Piper/chemistry , Molecular Structure , Plant Components, Aerial/chemistry , Animals , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Lignans/pharmacology , Lignans/isolation & purification , Lignans/chemistry , Glycosides/pharmacology , Glycosides/isolation & purification , Glycosides/chemistry , Cyclohexenes/pharmacology , Cyclohexenes/isolation & purification , China
19.
J Nat Prod ; 87(4): 1179-1186, 2024 Apr 26.
Article in English | MEDLINE | ID: mdl-38528772

ABSTRACT

A comprehensive phytochemical investigation of aerial parts obtained from Centaurea sicula L. led to the isolation of 14 terpenoids (1-14) and nine polyphenols (15-23). The sesquiterpenoid group (1-11) included three structural families, namely, elemanolides (1-6), eudesmanolides (7 and 8), and germacranolides (9-11) with four unreported secondary metabolites (5-8), whose structure has been determined by extensive spectroscopic analysis, including 1D/2D NMR, HR-MS, and chemical conversion. Moreover, an unprecedented alkaloid, named siculamide (24), was structurally characterized, and a possible biogenetic origin was postulated. Inspired by the traditional use of the plant and in the frame of ongoing research on compounds with potential activity on metabolic syndrome, all the isolated compounds were evaluated for their stimulation of glucose uptake, disclosing remarkable activity for dihydrocnicin (10) and the lignan salicifoliol (15).


Subject(s)
Centaurea , Glucose , Plant Components, Aerial , Plant Components, Aerial/chemistry , Centaurea/chemistry , Molecular Structure , Glucose/metabolism , Terpenes/chemistry , Terpenes/isolation & purification , Terpenes/pharmacology , Polyphenols/chemistry , Polyphenols/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Sesquiterpenes/isolation & purification
20.
Chem Biodivers ; 21(5): e202400302, 2024 May.
Article in English | MEDLINE | ID: mdl-38454878

ABSTRACT

This study isolated pure compounds from Canna edulis aerial parts and assessed their antiplatelet and anticoagulant potential. Structural elucidation resulted in the identification of two new compounds: caneduloside A (1) and caneduloside B (2), and eleven known compounds: 6'-acetyl-3,6,2'-tri-p-coumaroyl sucrose (3), 6'-acetyl-3,6,2'-triferuloyl sucrose (4), tiliroside (5), afzelin (6), quercitrin (7), 2-hydroxycinnamaldehyde (8), cinnamic acid (9), 3,4-dimethoxycinnamic acid (10), dehydrovomifoliol (11), 4-hydroxy-3,5-dimethoxybenzaldehyde (12), and (S)-(-)-rosmarinic acid (13). Compounds 3, 4, 6-9, 13 were previously reported for antithrombotic properties. Hence, antithrombotic tests were conducted for 1, 2, 5, 10-12. All tested compounds demonstrated a dose-dependent antiaggregatory effect, and 10 and 12 were the most potent for both ADP and collagen activators. Additionally, 10 and 12 showed anticoagulant effects, with prolonged prothrombin time and activated partial thromboplastin time. The new compound 1 displayed antiplatelet and anticoagulant activity, while 2 mildly inhibited platelet aggregation. C. edulis is a potential source for developing antithrombotic agents.


Subject(s)
Anticoagulants , Plant Components, Aerial , Platelet Aggregation Inhibitors , Sucrose , Anticoagulants/pharmacology , Anticoagulants/chemistry , Anticoagulants/isolation & purification , Platelet Aggregation Inhibitors/pharmacology , Platelet Aggregation Inhibitors/chemistry , Platelet Aggregation Inhibitors/isolation & purification , Sucrose/chemistry , Sucrose/pharmacology , Sucrose/metabolism , Plant Components, Aerial/chemistry , Plant Components, Aerial/metabolism , Humans , Esters/chemistry , Esters/pharmacology , Esters/isolation & purification , Platelet Aggregation/drug effects , Myristicaceae/chemistry , Dose-Response Relationship, Drug , Molecular Structure , Structure-Activity Relationship , Animals
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