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1.
Mini Rev Med Chem ; 24(19): 1784-1798, 2024.
Article in English | MEDLINE | ID: mdl-38639277

ABSTRACT

Aloe-emodin (AE) is an anthraquinone derivative and a biologically active component sourced from various plants, including Rheum palmatum L. and Aloe vera. Known chemically as 1,8-dihydroxy-3-hydroxymethyl-anthraquinone, AE has a rich history in traditional medicine and is esteemed for its accessibility, safety, affordability, and effectiveness. AE boasts multiple biochemical and pharmacological properties, such as strong antibacterial, antioxidant, and antitumor effects. Despite its array of benefits, AE's identity as an anthraquinone derivative raises concerns about its potential for liver and kidney toxicity. Nevertheless, AE is considered a promising drug candidate due to its significant bioactivities and cost efficiency. Recent research has highlighted that nanoformulated AE may enhance drug delivery, biocompatibility, and pharmacological benefits, offering a novel approach to drug design. This review delves into AE's pharmacological impacts, mechanisms, pharmacokinetics, and safety profile, incorporating insights from studies on its nanoformulations. The goal is to outline the burgeoning research in this area and to support the ongoing development and utilization of AE-based therapies.


Subject(s)
Anthraquinones , Anthraquinones/chemistry , Anthraquinones/pharmacology , Humans , Animals , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Aloe/chemistry , Drug Compounding
2.
Fitoterapia ; 175: 105961, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38626855

ABSTRACT

Two unprecedented quinone compounds Rubiaxylm A (1) and Rubiaxylm B (2), along with fifteen known anthraquinones (3-17) were isolated and characterized from the roots of Rubia tibetica in Tibetan medicine. Their structures were identified through comprehensive analyses of 1D/2D NMR as well as HR-ESIMS data. Furthermore, all separated compounds were evaluated for their cytotoxic activity on A549, Caco-2, MDA-MB-231 and Skov-3 cell lines. In particular, compound 2 effectively inhibited MDA-MB-231 cells with an IC50 value of 8.15 ± 0.20 µM. Subsequently, the anti-tumor mechanism of 2 was investigated by flow cytometry, JC-1 staining, cell scratching and cell colony. These results indicated that compound 2 could inhibit the proliferation of MDA-MB-231 cells by arresting cells in the G1 phase.


Subject(s)
Antineoplastic Agents, Phytogenic , Medicine, Tibetan Traditional , Phytochemicals , Plant Roots , Rubia , Humans , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Molecular Structure , Cell Line, Tumor , Rubia/chemistry , Plant Roots/chemistry , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Anthraquinones/pharmacology , Anthraquinones/isolation & purification , Anthraquinones/chemistry , Tibet , Quinones/pharmacology , Quinones/isolation & purification , Quinones/chemistry
3.
Adv Healthc Mater ; 13(19): e2304674, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38501303

ABSTRACT

Ulcerative colitis (UC) is a chronic inflammatory disease with uncontrolled inflammation and demage to the intestinal barrier. Rhein, a bioactive compound in traditional Chinese medicine, has anti-inflammatory and intestinal repair effect. However, their clinical application is limited by their hydrophobicity and poor bioavailability. L-arginine, as a complement to NO, has synergistic and attenuating effects. In this paper, red/NIR-I fluorescent carbon dots based on rhein and doped with L-arginine (RA-CDs), which are synthesized by a hydrothermal process without any organic solvents, are reported. RA-CDs preserve a portion of the functional group of the active precursor, increase rhein solubility, and emit red/NIR-I light for biological imaging. In vitro experiments show that RA-CDs scavenge excessive reactive oxygen species (ROS), protect cells from oxidative stress, and enable the fluorescence imaging of inflamed colons. In a DSS-induced UC mouse model, both delayed and prophylactic treatment with RA-CDs via intraperitoneal and tail vein injections alleviate UC severity by reducing intestinal inflammation and restoring the intestinal barrier. This study highlights a novel strategy for treating and imaging UC with poorly soluble small-molecule drugs.


Subject(s)
Anthraquinones , Carbon , Colitis, Ulcerative , Reactive Oxygen Species , Anthraquinones/chemistry , Anthraquinones/pharmacology , Animals , Mice , Carbon/chemistry , Colitis, Ulcerative/drug therapy , Colitis, Ulcerative/metabolism , Humans , Reactive Oxygen Species/metabolism , Quantum Dots/chemistry , Mice, Inbred C57BL , Dextran Sulfate , Arginine/chemistry , Fluorescent Dyes/chemistry , Disease Models, Animal , Male
4.
BMC Plant Biol ; 24(1): 226, 2024 Mar 28.
Article in English | MEDLINE | ID: mdl-38539101

ABSTRACT

BACKGROUND: Plant growth and quality are often affected by environmental factors, including geographical location, climate, and soil. In this study, we describe the effect of altitudinal differences on the growth and active ingredients in Rheum tanguticum Maxim. ex Balf. (R. tanguticum), a traditional Chinese medicinal herb known for its laxative properties. RESULTS: The results showed that plants grown at lower altitudes had better growth performances than those in higher altitude areas. The yield varied by 2.45-23.68 times with altitude, reaching a maximum of 102.01 t/ha. In addition, total anthraquinone and total sennoside contents decreased with increasing altitude, whereas total tannins increased with increasing altitude. The total anthraquinone content of the indicator compound reached 5.15% at five experimental sites, which exceeded the Chinese Pharmacopoeia standard by 70.87%. The content of the other two categories of active ingredients reached a maximum value of 0.94% (total sennosides) and 2.65% (total tannins). Redundancy analysis revealed that annual rainfall, annual average temperature, annual sunshine hours, and pH significantly affected growth and active ingredients. Moreover, key metabolites, such as flavonoids, amino acids and their derivatives, phenolic acids, lipids, and terpenes, were differentially expressed between samples from low- and high-altitude cultivation areas. These metabolites were enriched in the flavonoid and flavonol biosynthetic pathway and the monoterpene biosynthetic pathway. CONCLUSIONS: These results suggest that high anthraquinone content was observed in the lowest-latitude cultivation area due to low rainfall and alkaline soil pH. Key metabolites were significantly upregulated in high-latitude cultivation areas. These results provide a scientific basis for quality control and the systematic cultivation of R. tanguticum.


Subject(s)
Rheum , Rheum/chemistry , Tannins/metabolism , Anthraquinones/chemistry , Anthraquinones/metabolism , Soil
5.
J Chromatogr Sci ; 62(6): 534-553, 2024 Jul 10.
Article in English | MEDLINE | ID: mdl-38251765

ABSTRACT

Shen-Wu-Yi-Shen tablets (SWYST) is a traditional Chinese medicine prescription used for treating chronic kidney disease (CKD). This study aims to characterize the constituents in SWYST and evaluate the quality based on the quantification of multiple bioactive components. SWYST samples were analyzed with ultra-high-performance liquid chromatography quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS) and a data-processing strategy. As a result, 215 compounds in SWYST were unambiguously identified or tentatively characterized, including 14 potential new compounds. Meanwhile, strategies based on characteristic fragments for rapid identification were summarized, indicating that the qualitative method is accurate and feasible. Notably, the glucose esters of laccaic acid D-type anthraquinone were first found and their fragmentation patterns were described by comparing that of O-glycoside isomers. Besides, based on comparisons of the cleavage ways of mono-acyl glucose with different acyl groups or acylation sites, differences in fragmentation pathways between 1,2-di-O-acyl glucose and 1,6-di-O-acyl glucose were proposed for the first time and verified by reference substances. In addition, a validated UPLC-DAD was established for the determination of 11 major bioactive components related to treatment of CKD (albiflorin, paeoniflorin, 2,3,5,4'-tetrahydroxy-stilbene-2-O-ß-d-glucoside (TSG), 1-O-galloyl-2-O-cinnamoyl-ß-d-glucose, emodin-8-O-ß-d-glucoside, chrysophanol-O-ß-d-glucoside, aloe-emodin, rhein, emodin, chrysophanol and physcion). Moreover, TSG and 1-O-galloyl-2-O-cinnamoyl-ß-d-glucose were found as the quality markers related to the origins of SWYST based on multivariate statistical analysis. Conclusively, the findings in this work provide a feasible reference for further studies on quality research and mechanisms of action in treating CKD.


Subject(s)
Drugs, Chinese Herbal , Tandem Mass Spectrometry , Chromatography, High Pressure Liquid/methods , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/analysis , Tandem Mass Spectrometry/methods , Multivariate Analysis , Tablets/chemistry , Reproducibility of Results , Anthraquinones/analysis , Anthraquinones/chemistry , Linear Models
6.
Nat Prod Res ; 38(1): 91-96, 2024.
Article in English | MEDLINE | ID: mdl-35921492

ABSTRACT

Two new anthraquinone derivatives sapranquinones A and B (1 and 2) together with two known biogenetically related anthraquinone derivatives (3 and 4) were isolated from the stems of Saprosma crassipes H. S. Lo. The structures of these compounds were elucidated using comprehensive spectroscopic methods. Compounds 1-4 were evaluated for their antibacterial activities and compounds 1 and 3 had a broad spectrum antibacterial activity against Staphylococcus albus, Escherichia coli, Bacillus cereus, Micrococcus tetragenus, and Micrococcus luteus with MIC values ranging from 1.25 to 5 µg/mL.


Subject(s)
Anthraquinones , Rubiaceae , Anthraquinones/chemistry , Anti-Bacterial Agents/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Spectrum Analysis , Rubiaceae/chemistry , Escherichia coli , Microbial Sensitivity Tests
7.
Molecules ; 28(24)2023 Dec 17.
Article in English | MEDLINE | ID: mdl-38138627

ABSTRACT

Anthraquinones are bioactive natural products, which are often found in medicinal herbs. These compounds exert antioxidant-related pharmacological actions including neuroprotective effects, anti-inflammation, anticancer, hepatoprotective effects and anti-aging, etc. Considering the benefits from their pharmacological use, recently, there was an upsurge in the development and utilization of anthraquinones as reactive oxygen species (ROS) regulators. In this review, a deep discussion was carried out on their antioxidant activities and the structure-activity relationships. The antioxidant mechanisms and the chemistry behind the antioxidant activities of both natural and synthesized compounds were furtherly explored and demonstrated. Due to the specific chemical activity of ROS, antioxidants are essential for human health. Therefore, the development of reagents that regulate the imbalance between ROS formation and elimination should be more extensive and rational, and the exploration of antioxidant mechanisms of anthraquinones may provide new therapeutic tools and ideas for various diseases mediated by ROS.


Subject(s)
Anthraquinones , Antioxidants , Humans , Antioxidants/pharmacology , Reactive Oxygen Species , Anthraquinones/pharmacology , Anthraquinones/chemistry , Structure-Activity Relationship
8.
J AOAC Int ; 106(6): 1598-1607, 2023 Nov 02.
Article in English | MEDLINE | ID: mdl-37471690

ABSTRACT

BACKGROUND: Rubia cordifolia L., Rubiaceae, is globally reported to treat skin-related problems. The study aimed to assess the antityrosinase potential of Rubia cordifolia (ARC) and the development of gel formulation. METHODS: The AutoDock Vina (version V.1.2.0) program package was used for molecular docking to check for the binding affinity of ligands with protein. Response surface methodology (RSM) software was used to optimize extraction parameters for an alcoholic extract of Rubia cordifolia (ARC). The developed HPTLC method for the quantification of purpurin in ARC was validated as per the International Conference on Harmonization (ICH) guidelines. A bioautographic study for the evaluation of antityrosinase effects was performed; an anthraquinone-enriched fraction (AEF)-loaded gel formulation developed and evaluated physicochemically which could be used to reduce skin pigmentation. RESULTS: Purpurin showed optimum binding affinity (-7.4 kcal/mol) with the molecular target (tyrosinase) when compared to that of standard kojic acid (-5.3 kcal/mol). Quantification of purpurin in ARC, optimized by RSM software, was validated and physiologically significant results were observed for the antityrosinase potential of an AEF, along with TLC-MS-bioautographic identification for antityrosinase compounds: purpurin (m/z 256.21) and ellagic acid (m/z 302.19). Evaluation of an AEF-loaded gel formulation by in vitro and ex vivo permeation studies was performed. CONCLUSION: ARC extraction parameters optimized by RSM, and a bioautographic study helped identify antityrosinase compounds. The development of a gel formulation could be a cost-effective option for the treatment of depigmentation in the future. HIGHLIGHTS: A TLC-MS-Bioautography-based Identification of Antityrosinase Compounds and development of AEF-loaded Topical Gel formulation from a Bioactive Fraction of an RSM-Optimized Alcoholic Extract of Rubia Cordifolia L. stem, which could help with promising results in reducing skin pigmentation and maintaining even tone.


Subject(s)
Rubia , Rubia/chemistry , Rubia/metabolism , Molecular Docking Simulation , Plant Extracts/chemistry , Anthraquinones/chemistry , Anthraquinones/metabolism
9.
Molecules ; 28(5)2023 Mar 03.
Article in English | MEDLINE | ID: mdl-36903594

ABSTRACT

The composition of an ethanol extract from the roots of Rumex tianschanicus Losinsk of the Trans-Ili Alatau wild flora was studied in order to determine its antiulcer activity. The phytochemical composition of the anthraquinone-flavonoid complex from (AFC) R. tianschanicus revealed the presence of numerous polyphenolic compounds, the most abundant of which are anthraquinones (1.77%), flavonoids (6.95%), and tannins (13.39%). The use of column chromatography (CC) and thin-layer chromatography (TLC) in conjunction with UV, IR, NMR spectroscopy, and mass spectrometry data allowed the researchers to isolate and identify the major components of the anthraquinone-flavonoid complex's polyphenol fraction: physcion, chrysophanol, emodin, isorhamnetin, quercetin, and myricetin. The gastroprotective effect of the polyphenolic fraction of the anthraquinone-flavonoid complex (AFC) of R. tianschanicus roots was examined in an experimental model of rat gastric ulcer induced by indomethacin. The preventive and therapeutic effect of the anthraquinone-flavonoid complex at a dose of 100 mg/kg was analyzed using intragastric administration per day for 1 to 10 days, followed by a histological examination of stomach tissues. It has been demonstrated that prophylactic and prolonged use of the AFC R. tianschanicus in laboratory animals resulted in significantly less pronounced hemodynamic and desquamative changes in the epithelium of gastric tissues. The acquired results thus offer fresh insight into the anthraquinone and flavonoid metabolite component composition of R. tianschanicus roots, and they imply that the examined extract can be used to develop herbal medicines with antiulcer activity.


Subject(s)
Anti-Ulcer Agents , Rumex , Stomach Ulcer , Rats , Animals , Rumex/chemistry , Anthraquinones/chemistry , Plant Extracts/chemistry , Flavonoids/therapeutic use , Anti-Ulcer Agents/chemistry , Stomach Ulcer/chemically induced
10.
J Agric Food Chem ; 71(14): 5721-5732, 2023 Apr 12.
Article in English | MEDLINE | ID: mdl-36971230

ABSTRACT

Safety issues of the controversial anthraquinones from Cassia obtusifolia seed water extracts (CWEs) limit its application. This work aimed to remove the anthraquinones of CWEs by baking treatment (BT), stir-frying treatment (ST), and adsorption treatment (AT). Effects of these treatments on the chemical composition, physicochemical properties of polysaccharides, and antioxidant activities of CWEs were analyzed and compared. Results indicated that AT exhibited the best removal effect on the total anthraquinone among the three treatments. After AT, the contents of rhein, emodin, aloe-emodin, and aurantio-obtusin of the CWE were below the limit of detection. In addition, AT increased the contents of neutral sugars in CWEs in comparison to BT and ST. None of the treatments had an obvious influence on the structural characteristics of polysaccharides. However, AT decreased the antioxidant activity of CWEs due to their lower anthraquinone content. In summary, AT was considered as an efficient and simple method to remove anthraquinones, while retaining the features of polysaccharides.


Subject(s)
Anthraquinones , Cassia , Plant Extracts , Seeds , Adsorption , Anthraquinones/chemistry , Antioxidants/analysis , Cassia/chemistry , Cooking/methods , Emodin/analysis , Plant Extracts/chemistry , Polysaccharides/analysis , Seeds/chemistry
11.
Appl Microbiol Biotechnol ; 107(7-8): 2061-2071, 2023 Apr.
Article in English | MEDLINE | ID: mdl-36847855

ABSTRACT

Since ancient times, Morinda species, particularly Morinda citrifolia, have been used for their therapeutic benefits. Iridoids, anthraquinones, coumarins, flavonoids, lignans, phytosterols, and carotenoids are examples of natural substances with bioactivity. Anthraquinone derivatives are the most significant of these chemicals since they are utilized as natural coloring agents and have a wide range of medicinal functions. Utilizing cell and organ cultures of Morinda species, various biotechnological methods have been developed for the bioproduction of anthraquinone derivatives. The generation of anthraquinone derivatives in cell and organ cultures is summarized in this article. The methods used to produce these chemicals in bioreactor cultures have also been examined. KEY POINTS: • This review investigates the potential of cell and organ cultures for anthraquinone synthesis. • The overproduction of anthraquinones has been addressed using a variety of techniques. • The use of bioreactor technologies for anthraquinone manufacturing is highlighted.


Subject(s)
Lignans , Morinda , Organ Culture Techniques , Morinda/chemistry , Anthraquinones/chemistry , Plant Extracts/chemistry
12.
Chem Biodivers ; 20(3): e202200901, 2023 Mar.
Article in English | MEDLINE | ID: mdl-36788177

ABSTRACT

Rheum tanguticum (Rh. tanguticum) is a Chinese medicinal plant traditionally used in the treatment of constipation. As a byproduct, the seeds of this plant are rich in nutrients and phytochemicals. This study aimed to determine and assess seed germination ability, seed physical characteristics, soluble protein content, chemical constituents and antioxidant capacity from different breeding lines, to promote the development and utilization of seed resources. Significant differences were observed for the soluble protein content and antioxidant assays among the ten lines. The contents of aloe-emodin, rhein and catechins accumulated in seeds were extremely low and significantly different from those in roots. In contrast, emodin and chrysophanol were abundant in seeds, and significant differences were observed between seeds and roots. It was found that associations between gallic acid and catechins were not significant for either soluble protein or antioxidant capacity. There was a significantly positive correlation between the contents of four anthraquinones (aloe-emodin, rhein, emodin and chrysophanol) and soluble protein. Seeds have potent antioxidative capacity and relatively high levels of soluble protein content. The rich chemical composition of seeds can be widely used in the medical industry for further development.


Subject(s)
Antioxidants , Rheum , Anthraquinones/pharmacology , Anthraquinones/chemistry , Antioxidants/pharmacology , Emodin , Rheum/chemistry , Seeds/chemistry , Tibet
13.
Nat Prod Res ; 37(9): 1456-1462, 2023 May.
Article in English | MEDLINE | ID: mdl-34894893

ABSTRACT

The phytochemical investigation on the fruits of Morinda citrifolia led to the isolation and characterization of a new anthraquinone, moricitrifone (1), along with seven known anthraquinones (2-8). The chemical structure of 1 was elucidated by extensive spectral analyses. The known compounds (2-8) were identified by comparing their spectral data with those reported in the literature. The antiproliferative activities of all isolated anthraquinones (1-8) against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 were evaluated in vitro. Compounds 1-8 exhibited remarkable antiproliferative activities with IC50 values ranging from 0.26 ± 0.05 to 16.58 ± 0.18 µM, which were comparable to those of doxorubicin.


Subject(s)
Morinda , Humans , Morinda/chemistry , Molecular Structure , Fruit/chemistry , Plant Extracts/chemistry , Anthraquinones/chemistry
14.
Nat Prod Res ; 37(9): 1511-1517, 2023 May.
Article in English | MEDLINE | ID: mdl-35021945

ABSTRACT

In connection with our continuous efforts in the synthesis of derivatives from major compounds isolated from traditional medicinal plants, in the present study we have attempted to synthesize the furan-conjugated aloe-emodin derivatives (5a-j) using a three-component reaction. The synthesized derivatives were assessed for anticancer activity against five different cancer cell lines using the in vitro MTT assay and the results showed that most of the derivatives are potent against cancer cells comparing with the control. Compounds 5a and 5e showed excellent activity against all the cancer cells with less than 12.5 µM and arrested the cell cycle at the G0/G1 phase in both CAL27 and SCC9 cells. Compound 5e induces the early apoptosis in CAL27 cells and compounds 5a and 5e induce early and late apoptosis, respectively, in SCC9 cells. Moreover, compounds 5b, 5c, 5i, and 5j showed excellent anti-inflammatory activity in LPS-stimulated RAW 264.7 cells by inhibiting IL-6 production. The molecular docking studies revealed that compound 5e has strong interaction with the CLK kinase and protein kinase II through hydrogen binding Asp325 and Lys290.


Subject(s)
Aloe , Antineoplastic Agents , Emodin , Rheum , Rheum/chemistry , Aloe/chemistry , Rhizome , Molecular Docking Simulation , Anthraquinones/pharmacology , Anthraquinones/chemistry , Antineoplastic Agents/pharmacology , Anti-Inflammatory Agents/pharmacology
15.
Toxicology ; 478: 153293, 2022 08.
Article in English | MEDLINE | ID: mdl-35995123

ABSTRACT

Cassiae semen (CS), a traditional Chinese medicine, has various bioactivities in preclinical and clinical practice. Aurantio-obtusin (AO) is a major anthraquinone (AQ) ingredient derived from CS, and has drawn public concerns over its potential hepatotoxicity. We previously found that AO induces hepatic necroinflammation by activating NOD-like receptor protein 3 inflammasome signaling. However, the mechanisms contributing to AO-motivated hepatotoxicity remain unclear. Herein, we evaluated hepatotoxic effects of AO on three liver cell lines by molecular and biochemical analyses. We found that AO caused cell viability inhibition and biochemistry dysfunction in the liver cells. Furthermore, AO elevated reactive oxygen species (ROS), followed by mitochondrial dysfunction (decreases in mitochondrial membrane potential and adenosine triphosphate) and apoptosis (increased Caspase-3, Cleaved caspase-3, Cytochrome c and Bax expression, and decreased Bcl-2 expression). We also found that AO increased the lipid peroxidation (LPO) and enhanced ferroptosis by activating cyclic adenosine monophosphate (cAMP)-protein kinase A (PKA)-cAMP response element-binding (CREB) pathway (increases in PKA, p-CREB, acyl-CoA synthetase long chain family member 4). Based on these results, we used an AOP framework to explore the mechanisms underlying AO's hepatotoxicity. It starts from molecular initiating event (ROS), and follows two critical toxicity pathways (i.e., mitochondrial dysfunction-mediated apoptosis and LPO-enhanced ferroptosis) over a series of key events (KEs) to the adverse outcome of hepatotoxicity. The results of an assessment confidence in the adverse outcome pathway (AOP) framework supported the evidence concordance in dose-response, temporal and incidence relationships between KEs in AO-induced hepatotoxicity. This study's findings offer a novel toxicity pathway network for AO-caused hepatotoxicity.


Subject(s)
Adverse Outcome Pathways , Chemical and Drug Induced Liver Injury , Anthraquinones/chemistry , Anthraquinones/pharmacology , Caspase 3 , Chemical and Drug Induced Liver Injury/etiology , Humans , Reactive Oxygen Species
16.
Molecules ; 27(4)2022 Feb 10.
Article in English | MEDLINE | ID: mdl-35208994

ABSTRACT

Rumex confertus belongs to the genus Rumex and is classified as an invasive parasitic plant in agriculture. Despite other Rumex species being widely used in herbal medicine due to their antimicrobial, antioxidant, antitumor, and anti-inflammatory effects, there are almost no information about the potential of Rumex confertus for the treatment of various diseases. In this review we analyzed scientific articles revealing properties of Rumex plant's substances against cancer, diabetes, pathogenic bacterial invasions, viruses, inflammation, and oxidative stress for the past 20 years. Compounds dominating in each composition of solvents for extraction were discussed, and common thin layer chromatography(TLC) and high performance liquid chromatography(HPLC) methods for efficient separation of the plant's extract are included. Physico-chemical properties such as solubility, hydrophobicity (Log P), pKa of flavonoids, anthraquinones, and other derivatives are very important for modeling of pharmacokinetic and pharmacodynamics. An overview of clinical studies for abounded selected substances of Rumex species is presented.


Subject(s)
Anthraquinones/therapeutic use , Flavonoids/therapeutic use , Rumex/chemistry , Anthraquinones/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/therapeutic use , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/therapeutic use , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/therapeutic use , Antioxidants/chemistry , Antioxidants/therapeutic use , Flavonoids/chemistry
17.
Int J Mol Sci ; 23(3)2022 Jan 23.
Article in English | MEDLINE | ID: mdl-35163169

ABSTRACT

The antioxidant/pro-oxidant activity of drugs and dietary molecules and their role in the maintenance of redox homeostasis, as well as the implications in health and different diseases, have not yet been fully evaluated. In particular, the redox activity and other interactions of drugs with essential redox metal ions, such as iron and copper, need further investigation. These metal ions are ubiquitous in human nutrition but also widely found in dietary supplements and appear to exert major effects on redox homeostasis in health, but also on many diseases of free radical pathology. In this context, the redox mechanistic insights of mainly three prototype groups of drugs, namely alpha-ketohydroxypyridines (alpha-hydroxypyridones), e.g., deferiprone, anthraquinones, e.g., doxorubicin and thiosemicarbazones, e.g., triapine and their metal complexes were examined; details of the mechanisms of their redox activity were reviewed, with emphasis on the biological implications and potential clinical applications, including anticancer activity. Furthermore, the redox properties of these three classes of chelators were compared to those of the iron chelating drugs and also to vitamin C, with an emphasis on their potential clinical interactions and future clinical application prospects in cancer, neurodegenerative and other diseases.


Subject(s)
Antioxidants/pharmacology , Chelating Agents/chemistry , Transition Elements/chemistry , Anthraquinones/chemistry , Anthraquinones/pharmacology , Antioxidants/chemistry , Chelating Agents/pharmacology , Coordination Complexes/chemistry , Copper/chemistry , Doxorubicin/chemistry , Doxorubicin/pharmacology , Free Radicals/chemistry , Iron/chemistry , Iron Chelating Agents/chemistry , Iron Chelating Agents/pharmacology , Oxidation-Reduction/drug effects , Pyridines/chemistry , Pyridines/pharmacology , Reactive Oxygen Species/chemistry , Thiosemicarbazones/chemistry , Thiosemicarbazones/pharmacology
18.
Biomed Chromatogr ; 36(5): e5324, 2022 May.
Article in English | MEDLINE | ID: mdl-34993982

ABSTRACT

Da-Huang-Xiao-Shi decoction (DHXSD) is a traditional Chinese medicine formula and is used to treat cholestasis. In this study, we developed a reliable and comprehensive HPLC coupled with a linear ion trap-Orbitrap mass spectrometry method for the separation and determination of 21 components including six alkaloids, five anthraquinones, three tannins, three terpenes, two iridoid glycosides, one organic acid and one flavonoid in DHXSD. A C18 column was eluted using a gradient mobile phase at a flow rate of 1 ml/min. Detection was operated with an electrospray ionization source in positive and negative ion modes using selective ion monitoring. The calibration curves for all analytes showed good linearity (r > 0.9901), and the inter- and intra-day precision did not exceed 4.98%. The recovery, repeatability and stability were also within the acceptable limits. The method was successfully applied to determine multiple active constituents in DHXSD and its constituent herbs. Compared with Da Huang, the total contents of the five anthraquinones were significantly higher in DHXSD. However, the changes in the components from Zhi Zi/Huang Bo were complicated in DHXSD. The study could serve as a fundamental reference for establishing comprehensive DHXSD quality control measures and be helpful to understand some compatibility laws of DHXSD.


Subject(s)
Drugs, Chinese Herbal , Anthraquinones/chemistry , Chromatography, High Pressure Liquid/methods , Drugs, Chinese Herbal/chemistry , Mass Spectrometry/methods
19.
Article in English | MEDLINE | ID: mdl-35032891

ABSTRACT

In traditional Chinese medicine (TCM), components with identical nuclei often share structural similarity, indicating the possibility of similar second-level mass spectrometry (MS/MS) fragments. High-resolution product-ion filter (HRPIF) technique can be utilized to identify metabolites, with similar fragments, in vivo. In principle, this technique applies to TCM; however, its application has been restricted due to the limitations of traditional MS/MS data acquisition. Therefore, a novel analysis strategy, based on data-dependent acquisition (DDA) and data-independent acquisition (DIA) datasets, has been developed for the determination of template product ions and efficient non-targeted identification of TCM-related components in vivo by HRPIF and background subtraction (BS). This DDA-DIA combination strategy, taking Rhei Radix et Rhizoma as a test case, identified 71 anthraquinone prototype components in vitro (36 of which were discovered for the first time), and 45 related components in vivo, confirming glucuronidation and sulfation as the main reactions. The developed strategy could rapidly identify TCM-related components in vivo with high sensitivity, indicating the immense importance of this novel HRPIF data mining technology in TCM analysis.


Subject(s)
Data Mining/methods , Drugs, Chinese Herbal/metabolism , Rheum/chemistry , Rhizome/chemistry , Administration, Oral , Animals , Anthraquinones/administration & dosage , Anthraquinones/blood , Anthraquinones/chemistry , Anthraquinones/metabolism , Drugs, Chinese Herbal/administration & dosage , Drugs, Chinese Herbal/chemistry , Male , Molecular Structure , Plasma/chemistry , Rats , Rats, Sprague-Dawley , Tandem Mass Spectrometry
20.
J Sep Sci ; 45(4): 938-944, 2022 Feb.
Article in English | MEDLINE | ID: mdl-34932273

ABSTRACT

Traditional bioassay-guided investigation of bioactive compounds from natural products comprises critical steps, such as extraction, repeated column separation, and activity assay. Thus, the development of facile, rapid, and efficient technology is critically important. Here, a HepG2 cell-based extraction method was first developed to rapidly screen potential antitumor compounds from the seeds ofCassia obtusifolia. Then, an online extraction and enrichment-high-speed counter-current chromatography (HSCCC) strategy was fabricated to facilely and efficiently isolate target antitumor compounds, which included direct extraction from solid C. obtusifolia, removal of polar interferences, enrichment of target compounds, and preparative isolation by HSCCC using flow rate stepwise increasing mode. After further purification by Sephadex LH-20 column, five antitumor anthraquinones, aurantio-obtusin, 1-desmethylaurantio-obtusin, chryso-obtusin, obtusin, and questin, were obtained for structural characterization and bioassay verification. The results may not only provide new perspectives for facile and rapid investigation of bioactive compounds from complex natural products, but also offer a scientific basis for the potential applications of C. obtusifolia.


Subject(s)
Cassia , Anthraquinones/chemistry , Cassia/chemistry , Countercurrent Distribution , Plant Extracts/chemistry , Seeds/chemistry
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