Anthraquinone Glycosides Research Articles

Madhuca longifolia (Mahua): A comprehensive ethno pharmacological review

Madhuca longifolia is cultivated as well as found in wild and considered as boon for the forest dwellers for its medicinal property. It is an economic plant grows mainly in subtropical region of India and Pakistan. It is commonly known as Mahua and known for its antimicrobial, antioxidant, antipyretic, anti-inflammatory, antiulcer, cardioprotective, anti-carcinogenic, immuno-modulant, anti-rheumatic, oxytocic, anti-estrogenic, uterotonic, antiepileptic, demulcents and many other useful pharmacological activities. Its chemical ingedients include terpenoids, proteins, starch, anthraquinone glycosides, phenolic compounds, mucilage, cardiac glycosides, tannins, flavonoids and saponins. This article gives a brief description of Madhuca longifolia regarding its identification, phytochemical properties, traditional uses including anti-inflammatory, antipyretic, antihyperglycemic, antifertility, antiulcer activities. The outcome of this review will further expand the existing knowledge about Mahua and provide a convincing support to its future clinical use in modern veterinary and human medicine.

Study on antipyretic effect of rhubarb on rats and its antipyretic ingredients

A combination of LC-MS technology and activity evaluation was used to identify the antipyretic ingredients in rhubarb. The rat model of fever was established with dried yeast and then was administered ethanol extract and different polar fractions of rhubarb. Next, the anal temperature of these rats was measured and recorded at 0.5, 1, 2, 3, 4 and 5 h after administration, and the inhibition rate of each part on the rise of body temperature was calculated. The inhibition rate is higher and the antipyretic effect is better. The chemical composition of the effective fraction was analyzed with UPLC-ESI-Orbitrap-MS/MS technology. Compared with the model group, the increase of body temperature of ethanol extract group all reduced at each measurement time especially after 3 h, and the inhibition rate were 38.7%(P<0.05), 78.2%(P<0.01) and 72.4%(P<0.01) at 3 h, 4 h, and 5 h after administration, respectively. Both n-butanol and water fraction showed some antipyretic activity in the early stage, with the inhibition rate of 28.1%(P<0.01) and 24.9%(P<0.05) at 1 h after administration, respectively, while other fractions were not active. Thirty-three and twelve compounds were identified from n-butanol and water fraction by LC-MS/MS analysis, respectively, including ten tannins, fifteen anthraquinone glycosides, four anthrone glycosides, one phenolic glycoside, one naphthaline derivative, one anthraquinone and one sucrose. These results revealed that rhubarb had antipyretic activity on rats, and tannin and anthraquinone glycosides were the main active ingredients inside.

Suppressive effects of aloin on polyphosphate-mediated vascular inflammatory responses

Human endothelial cells-derived polyphosphate (PolyP) is one of the pro-inflammatory mediators as suggested by the previous reports. Aloin is the major anthraquinone glycoside obtained from the Aloe species and exhibits anti-inflammatory and anti-oxidative activities. Aloin inhibits PolyP-mediated barrier disruption, the expressions of cell adhesion molecules, and adhesion/migration of leukocyte to HUVEC. PolyP-induced NF-κB activation and the productions of TNF-α and IL-6 were inhibited by aloin in HUVECs. These anti-inflammatory functions of aloin were confirmed in PolyP-injected mice. In conclusion, based on the anti-inflammatory effects of aloin in PolyP-mediated septic response, aloin has therapeutic potential for various systemic inflammatory diseases.

Inhibitory effects of aloin on TGFBIp-mediated septic responses

Aloin is the major anthraquinone glycoside obtained from the Aloe species. Transforming growth factor β-induced protein (TGFBIp) is an extracellular matrix protein and released by primary human umbilical vein endothelial cells (HUVECs) and functions as a mediator of experimental sepsis. We hypothesized that aloin could reduce TGFBIp-mediated severe inflammatory responses in HUVECs and mice. Aloin effectively inhibited lipopolysaccharide (LPS)-induced release of TGFBIp and suppressed TGFBIp-mediated septic responses. Aloin suppressed TGFBIp-induced sepsis lethality and pulmonary injury. Therefore, aloin is a potential therapeutic agent for various severe vascular inflammatory diseases, with inhibition of the TGFBIp signaling pathway as the mechanism of action.

TIRYAQ-I-AFAYEE (A POLYHERBAL FORMULATION) OF UNANI MEDICINE USED IN THE PREVENTION OF WABĀI AMRĀD (EPIDEMIC/ PANDEMIC DISEASES) – AN APPRAISAL

BACKGROUND AND OBJECTIVE: Tiryaq-i-Afayee, a polyherbal formulation of Unani medicine used in the prevention and treatment of various wabāi amrād (epidemic/ pandemic diseases) since olden days. This review study has been carried out to explore the therapeutic efficacy of this formulation in the light of scientific studies. MATERIALS & METHODS: A total of 74 literature comprising classical Unani texts from the period of 9th – 20th century AD, and published research articles in various reputed journals from 1999 – 2020 AD were reviewed regarding immunomodulatory, antiviral, antiinfluenza, antioxidant, antitussive, antimicrobial effects of Tiryaq-iAfayee, as a whole preparation and its individual ingredients. RESULTS:Tiryaq-i-Afayee contains Sibr Zard (Aloe vera) (2 parts), Murr Makki (Commiphora myrrha) (1 part) and Zafran (Crocus sativus) (1 part). It is prepared in the form of pill, and 2 g is used in alternate day for prevention and management of epidemic diseases. All the three ingredients of this compound formulation belong to plants and individually used for various medicinal purposes. DISCUSSION: A study revealed that Tiryaq-i-Afayee possesses significant immunomodulatory effect in a small group of immuno compromised persons. An ethanol extract of Aloe vera exhibited antiinfluenza effect against influenza A virus due to presence of aloe-emodine (anthraquinone glycoside). Certain studies have reported that Commiphora myrrha possesses significant antioxidant and antimicrobial effects against Staphylococcus aureus and Pseudomonas aeruginosa. Another study has revealed that Saffron extract exhibited promising antiviral activity due to presence of crocin and picrocrocin. CONCLUSION: The aforementioned classical and modern conventional materials have given plentiful information regarding use of Tiryaq-i-Afayee in the prevention of epidemic/ pandemic diseases.

Simultaneous determination of four anthraquinones in Polygonum multiflorum by QAMS

A simple, specific and selective quantitative analysis of multi-components by single marker(QAMS) method for simultaneous determination of anthraquinones and anthraquinone glycosides in Polygonum multiflorum was developed. Four main anthraquinones and its glycosides, emodin, emodin-8-O-β-D-glucoside, physcion and physcion-8-O-β-D-glucoside were selected as analytes to evaluate the quality of P. multiflorum. Emodin was used as the internal standard, and the relative correction factors(RCFs) between emodin and the other three anthraquinones were calculated. Comparison of the contents of the four components in 30 batches of P. multiflorum from different regions and 12 batches decoction pieces from different manufacturers by QAMS and external standard method(ESM) showed that there was no significant difference between QAMS and ESM for quantification of the four main components by using relative error results, and the QAMS method was accurate and reliable, and had a good repeatability. In addition, compared with the results calculated by the difference method between total anthraquinone and free anthraquinone in the content determination of P. multiflorum in Chinese Pharmacopoeia, the results of direct determination combined anthraquinone by QAMS were very close to that by measured the external standard method. Therefore, simultaneous quantification of four main anthraquinones by using QAMS is suitable to evaluate the quality of P. multiflorum. Then the optimized assay method of the combined anthraquinone contents showed simple and feasible, which could be replaced and improved the quantification method of the combined anthraquinone in the current Chinese Pharmacopeia.

Anti-Acinetobacter baumannii activity of Rumex crispus L. and Rumex sanguineus L. extracts

Objective: To examine the effect of Rumex crispus (R. crispus) and Rumex sanguineus (R. sanguineus) plant extracts against isolates of Acinetobacter baumannii (A. baumannii) from wounds, including multidrug-resistant strains. Methods: Six prepared Rumex extracts were subjected to liquid chromatography-tandem mass spectrometry. Antimicrobial activity of extracts and pure compounds (catechin, quercetin, isoquercitrin, emodin, and gallic acid) was examined by a microtiter plate method, while for determination of compound binary combinations activity a checkerboard method was applied. Active fractions of extracts were detected by agar-overlay high-performance thin- layer chromatography-bioautography assay followed by liquid chromatography - diode array detection - mass spectrometry analysis. Results: A total of 28 compounds were detected in two extracts of R. crispus and 26 compounds in four different R. sanguineus extracts, with catechin as a dominant component. Anti-A. baumannii activity was confirmed for all six R. sanguineus and R. crispus extracts at the concentration range from 1 to 4 mg/mL. Neither examined single compounds nor their binary combinations exhibited an anti-A. baumannii activity (MIC>256 μg/mL). The bioautography showed that fractions with the most prominent anti-A. baumannii activity tended to contain more polar compounds, predominantly flavonol (quercetin and kaempherol) glycosides; but also fractions containing flavanone (eriodictyol) glycosides and anthraquinone (emodin) glycosides; and less polar eriodictyol aglycone. Conclusions: The results justify and elucidate the traditional application of R. sanguineus and R. crispus extracts for wound healing, indicating the necessity for their further examination in combat against multidrug-resistant A. baumannii isolates from wounds.

Inhibition of NOX2 contributes to the therapeutic effect of aloin on traumatic brain injury.

Traumatic brain injury (TBI) is asubset of brain injury induced by external mechanical forces to the head or neck. TBIhas been reported to be one of the leading causes of disability, and it causes ahuge financial burden around the world. Aloin is the major anthraquinone glycoside extracted from Aloe species, and has presented anti-tumour, anti-oxidative and anti-inflammatory activities. However, few studies have focused the effect of aloin in treatment of TBI. Nicotinamide adenine dinucleotide phosphate oxidase (NOX) is the only subset of enzymes which produces solely the reactive oxygen species (ROS). A recent study showed that activation of NOX might aggravate the primary TBI, and among these members, NOX2 is the key member in regulation of uncontrolled ROS expression, and thus plays acritical role in development of inflammatory diseases. Here, we noticed that inhibition of NOX2 combined with aloin treatment promoted the recovery of brain function in amice model as well as the viability rate in acell model. A further study found that the inflammation response process was also inhibited after treatment. Then, we found that these effects might be mediated by the PI3K/AKT/mTOR signalling pathway and NOX2 might be atherapeutic target for TBI.

Discovery and characterization of four glycosyltransferases involved in anthraquinone glycoside biosynthesis in Rubia yunnanensis

Four new glycosyltransferases, which were discovered from Rubia yunnanensis for mediating anthraquinone glycoside biosynthesis, were identified through the analysis of broad substrates, sugar promiscuous, and regioselective glycosylation.

CHEMICAL CONSTITUENTS AND PHARMACOLOGICAL ACTIVITIES OF LANTANA CAMARA – A REVIEW

Objective: The review was designed to investigate the traditional uses, chemical constituents and pharmacological effects of Lantana camara.
 Methods: In the current review, databases including Web Science, Pub Med, Scopus and Science Direct, were searched to investigate the chemical constituents and pharmacological effects of Lantana camara.
 Results: The plant contained alkaloids, glycosides, steroids, saponins, flavanoids, coumarins, tannins, carbohydrates, hydroxy anthraquinones, anthraquinone glycosides, proteins, phytosteroids, fixed oils, fats, and triterpinoids. Previous pharmacological studies revealed that Lantana camara possessed antimicrobial, antiparasitic, anxiolytic, gastrointestinal, hypoglycemic, cardiovascular, antioxidant, anticancer, antiinflammatory, analgesic, wound healing, antiurolithiatic, hepatoprotective, reproductive, anti–hemorrhoidal, thrombin inhibition and many other effects.
 Conclusion: Lantana camara represents a promising medicinal plant with a wide range of pharmacological activities that could be utilized in several medical applications because of its effectiveness and safety.

Hepatotoxicity and mechanism study of chrysophanol-8-O-glucoside in vitro

To better understand the hepatotoxicity of anthraquinone glycosides, the hepatotoxicity of six anthraquinone glycosides was evaluated. The results show that chrysophanol-8-O-glucoside(C8G) has strong hepatotoxicity and can lead to increased LDH leakage and ROS, decreased GSH and MMP in L-02 hepatocytes. The results of C8G hepatotoxicity proteomics shows that, a total of 773 differentially expressed proteins were screened and analyzed using GO analysis and Pathway enrichment analysis. Our results show that C8G can lead to abnormal oxidative phosphorylation by inhibiting the function of mitochondrial complexes, resulting in decreased mitochondrial membrane potential (MMP), increased reactive oxygen species (ROS), and eventually resulting in mitochondrial damage and apoptosis. Western blot results verified the accuracy of quantitative proteomic results, and also evaluated the expression of Bax, caspase-3, -8, -9, Bcl-2, Cyt C in the mitochondria and cytosolic. The mitochondrial respiratory chain complexes activity assay result also confirmed that C8G could inhibit the activity of all mitochondrial complexes. The results of this study indicate that the hepatotoxicity mechanism of C8G is related to mitochondrial dysfunction, especially the mitochondrial complex function.

Cytotoxic and cytostatic effects of four Annonaceae plants on human cancer cell lines.

Several species of the Annonaceae plants have been used as complementary medicine for cancer-associated illnesses in some ethnic groups of northern Thailand. This study investigated the cytotoxic and cytostatic activity of methanolic extracts derived from the stems of these plants, including Uvaria longipes (Craib) L.L.Zhou, Y.C.F.Su & R.M.K.Saunders, Artabotrys burmanicus A.DC, Marsypopetalum modestum (Pierre) B.Xue & R.M.K.Saunders, and Dasymaschalon sp. Cell death induction of seven human cancer cell lines and cell cycle analyses were assessed by Annexin V and/or propidium iodide (PI) staining and analyzed by flow cytometry. Treatment of cancer cell lines with the extract of four Annonaceae plants resulted in various cytotoxic activities depending on cell type. The extract of U. longipes exhibited the highest cytotoxic activity capable of inducing cell death of several cancer cell lines, particularly against hepatocellular carcinoma cell lines (HepG2 and Hep3B). This extract was capable of inducing cell cycle arrest at the SubG1 phase. Phytochemical screening of all the extracts revealed the presence of alkaloids, sterols, tannins, anthraquinone glycoside, coumarin, and flavonoids. Determination of active compounds by high-performance liquid chromatography standards revealed bullatacin and asiminecin in all the extracts. The extract of Annonaceae stem or its compounds may provide an opportunity for the development of new therapies against cancer.

Renal protective effects of aloin in a mouse model of sepsis

Aloin is the major anthraquinone glycoside obtained from the Aloe species and exhibits anti-inflammatory and anti-oxidative activities. However, the renal protective effects of aloin and underlying molecular mechanism remain unclear. This study was initiated to determine whether aloin could modulate renal functional damage in a mouse model of sepsis and to elucidate the underlying mechanisms. The potential of aloin treatment to reduce renal damage induced by cecal ligation and puncture (CLP) surgery in mice was measured by assessment of serum creatinine, blood urea nitrogen (BUN), lipid peroxidation, total glutathione, glutathione peroxidase activity, catalase activity, and superoxide dismutase activity. Post-treatment with aloin resulted in a significant reduction in the deleterious renal functions by CLP, such as elevated BUN, creatinine, and urine protein. Moreover, aloin inhibited nuclear factor-κB activation and reduced the induction of nitric oxide synthase and excessive production of nitric acid. Aloin treatment also reduced the plasma levels of interleukin-6 and tumor necrosis factor-α, reduced lethality due to CLP-induced sepsis, increased lipid peroxidation, and markedly enhanced the antioxidant defense system by restoring the levels of superoxide dismutase, glutathione peroxidase, and catalase in kidney tissues. Our study suggested that aloin protects mice against sepsis-triggered renal injury.

Secondary metabolites from the resins of Aloe vera and Commiphora mukul mitigate lipid peroxidation.

Oxidative stress is often considered detrimental for cellular processes and damaging for the lipid bi-layer. Counteracting such stresses with the aid of nature-based chemical constituents can be an ideal therapeutic approach. The current study aimed to investigate the chemical constituents of resins derived from the well-known Aloe vera and less known Commiphora mukul trees and their effect in mitigating the lipid peroxidation (LPO) process. The bio-guided isolation of bio-active fractions from both resins afforded 20 chemical constituents (17 from A. vera and 3 from C. mukul). These compounds belonged to anthraquinones, anthraquinone glycosides, quinones, coumarins, polypodane-type terpenoids and benzene derivatives. Major chemical constituents of the resins of A. vera and C. mukul were from the classes of quinones and terpenoids. Feroxidin (4, from A. vera) showed slightly higher inhibition (IC50 = 201.7 ± 0.9 µmol L-1) than myrrhanone C (18, from C. mukul: IC50 = 210.7 ± 0.0 µmol L-1) and methyl 3-(4-hydroxyphenyl) propionate from A. vera (13, IC50 = 232.9 ± 0.2 µmol L-1) compared to the other compounds. Structure-activity relationship showed that the existence of hydroxyl, methoxy and ether groups might play a major role in countering oxidative stress. To the best of our knowledge, anti-LPO activities of compounds 1-4, 14, 18 and 20 are reported for the first time. Such chemical constituents with high anti-lipid peroxidation activity could be helpful in synthesizing candidate drugs.

Phytochemical analysis and antioxidant activity of different plant parts of Pellacalyx axillaris

Pellacalyx axillaris or locally known as ‘membuloh’ is a mangrove species belonging to the Rhizophoraceae family. Till date, there has been only one phytochemical study found on this particular plant species and that without any documentation on its biological activities. Therefore, the present work aimed to reveal the phytoconstituents and the antioxidant activity of different crude extracts from different plant parts of P. axillaris. Experimentally, three organic solvents of different polarities i.e. n-hexane, ethyl acetate and methanol were used to prepare the crude extracts from the dried leaves, twigs and barks of P. axillaris. The preliminary phytochemical screening of this species indicated the presence of terpenoids, phenolic compounds, tannins, flavonoids, alkaloids, anthraquinone glycosides and carbohydrates. The in vitro antioxidant activity of the species evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay, 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical scavenging assay, and ferric reducing antioxidant power (FRAP) suggested that the methanolic bark extract contained potential source of natural antioxidants. Further research into isolation of antioxidant compounds from this species is highly recommended.

Glycosidic compounds from Cassia obtusifolia seeds and their inhibitory effects on OATs, OCTs and OATPs

Phytochemical work on water-soluble ingredients extracted from Cassia obtusifolia seeds led to the isolation of twelve glycosidic compounds including three chromone C-glycosides (1-3), two anthraquinone glycosides (4, 5), six naphthopyran glycosides (6-11), and one naphthalene glycoside (12). The structures of all compounds were identified mainly by spectroscopic data analysis; 1-3 were three new chromone C-glycosides, and 4 was a new anthraquinone glycoside. All isolates were evaluated for the inhibitory activities against human organic anion/cation transporters (OATs/OCTs) and organic anion transporting polypeptides (OATPs) The results demonstrated that compound 7 exhibited a moderate inhibitory effect on OAT3, while 5 showed a moderate effect on OCT1. Compounds 4, 6, 8 and 10 displayed a moderate inhibitory effect on OATP1B3, and 10 inhibits OATP2B1 significantly.

Determination of Sennosides A and B in Sudanese Medicinal Plant Senna alexandrina Pods and Leaves using Reverse-Phase High Performance Liquid Chromatography

Senna alexandrina pods and leaves have been used in herbal medicine since ancient times. The extracts of this plant contain mainly anthraquinone glycosides that have a significant laxative effect. In this study, the sennosides A and B, the major constituents of Senna alexandrina were calculated via a simple and accurate HPLC method. The yield of sennoside A was found 1.22 and 1.83% in the pods and leaves, respectively. Whereas the yield of sennoside B was found 2.7 and 1.83% in the pods and leaves, respectively.

Evaluation of Antimicrobial Activities of Crude Methanol Extract of Phoenix dactylifera Seeds on Clinical Isolates of Different Strains of E. coli

Aim: This study was conducted to evaluate the antimicrobial activities of seed extract of Phoenix dactylifera.
 Study Design: Extraction of active ingredients of Phoenix dactylifera seeds using methanol and its effects on selected clinical isolates and isolated strains of E. coli.
 Place and Duration of Study: `Department of Phatrmaceutical Microbiology and Biotechnology, Faculty of Pharmaceutical, University of Nigeria, Nsukka between march 2017 and October 2018.
 Methodology: The seed of phoenix dactylifera were washed thoroughly to get rid of any adhering date flesh, air dried and ground. The ground powders were subjected to extraction by cold maceration using methanol. Preliminary sensitivity test was carried out against eight microorganisms, namely: Pseudomonas aeruginosa, E. coli, Enterococcus, Klebsiella, Staph. spp, Salmonella spp, Bacillus sp and Candida albicans using agar diffusion method. Antimicrobial susceptibility tests were carried out on isolated strains of E. coli from urine samples using agar diffusion method. The minimal inhibitory concentrations of crude methanol extract of seeds of Phoenix dactylifera were determined using agar diffusion method. The phytochemical analysis was conducted to determine the secondary metabolites.
 Results: The preliminary sensitivity test performed shows that the crude methanol extract of date seed were sensitive against all organisms tested. The active ingredients of the extract showed activities against all strains of E. coli tested though their zones of inhibition vary (18-21mm). The minimum inhibitory concentration (MIC) value ranges from 10-19.9 mg/ml. The phytochemical analysis of crude methanol seed extract of P. dacterifera indicated the presence of alkaloids, flavonoids, tannins, carbohydrates, proteins, reducing sugar, sterols and Terpenes, Anthraquinone glycosides.
 Conclusion: The present study provides the scientific information about Phoenix dactylifera seed activity.

Aloin reduces inflammatory gene iNOS via inhibition activity and p-STAT-1 and NF-κB

Aloin is the major anthraquinone glycoside obtained from the Aloe species and exhibits anti-inflammatory and anti-oxidative activities. Here, we aimed to determine the effects of aloin on heme oxygenase-1 (HO-1) induction and on the expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX) 2 in lipopolysaccharide (LPS)-activated human umbilical vein endothelial cells (HUVECs). To the end, aloin was tested whether aloin reduces iNOS protein expression and inflammatory markers (interleukin (IL)-1β and tumor necrosis factor (TNF)-α) in LPS-treated mice lung tissue. The results indicated that aloin affected HO-1 induction and reduced LPS-activated NF-κB-luciferase activity showed to preferential inhibition of iNOS/NO and COX-2/PGE2 that was partly related to inhibition of STAT-1 phosphorylation. In particular, aloin induced translocation of Nrf2 from cytosol into the nucleus by an increased Nrf2-ARE binding activity, and reduced IL-1β production in LPS-activated HUVECs. The reduced expression of iNOS/NO by aloin was reversed by siHO-1RNA-transfection. In LPS-treated mice, aloin significantly reduced iNOS protein in lung tissues, and TNF-α levels in the BALF. We concluded that aloin may be beneficial for treatment of lung injury.

A comparative study of UHPLC/Orbitrap MS metabolomics profiles and biological properties of Asphodeline taurica from Bulgaria and Turkey

The present investigation attempts to compare the pharmacological properties and phytochemical profile of four extracts (ethyl acetate, dichloromethane, methanol, and water) of Asphodeline taurica (Pall.) Endl. roots from Bulgaria and Turkey. The Bulgarian ethyl acetate extract displayed the highest antioxidant activity in the DPPH, CUPRAC, and phosphomolybdenum assay, and strongest inhibition against α-amylase and α-glucosidase. The Turkish aqueous extract exhibited the strongest ABTS scavenging and ferric reducing power while its methanol extract was the most effective acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitor. On the other hand, the Turkish dichloromethane extract showed the highest lipase inhibition. UHPLC/Orbitrap MS analysis showed a wide array of individual phenolics; six free anthraquinones, two bianthraquinones, three bianthracenes, three anthraquinone glycosides and one bianthracen glycoside were identified. The present data suggest that A. taurica roots can be considered as a valuable source of biologically active phytocompounds with functional properties for the cosmetic and pharmaceutical industries.