alloin and aloe-emodin

Aloe is a genus of medicinal plants with a notable history of medical use. Basic research over the past couple of decades has begun to reveal the extent of Aloe's pharmaceutical potential, particularly against neoplastic disease. This review looks at Aloe, both the genus and the folk medicine, often being called informally "aloes", and delineates their chemistry and anticancer pharmacognosy. Structures of key compounds are provided, and their pharmacological activities reviewed. Particular attention is given to their free radical scavenging, antiproliferative, and immunostimulatory properties. This review highlights major research directions on aloes, reflecting the enormous potential of natural sources, and of the genus Aloe in particular, in preventing and treating cancer.

Topics: Adjuvants, Immunologic; Aloe; Animals; Anthraquinones; Antineoplastic Agents, Phytogenic; Antioxidants; Emodin; Humans; Mannans; Medicine, Traditional; Plant Extracts; Plant Lectins; Plants, Medicinal

Aloe barbadensis Mill. (Aloe vera), is a homology of medicine and food plant, widely applied in functional food, cosmetics, and medicine. Aloe vera whole leaf extract, one of the most popular traditional Chinese medicines (TCMs), is mainly used in China to treat functional constipation.. To elucidate the active constituents of Aloe vera for treating functional constipation.. Prototype constituents and metabolites in rat plasma and excreta after oral administration of Aloe vera whole leaf extract were identified by UPLC-Q-TOF/MS, and the pharmacokinetics (PK) properties of its key anti-constipation constituents speculated by network pharmacology were investigated via the established UFLC-MS/MS method.. A total of 13 prototype constituents and 56 metabolites were identified in rat plasma, urine, and feces after oral administration of Aloe vera. Among them, aloesin, aloenin, aloin B, aloin A, and aloe-emodin were intimately connected to the core targets of constipation in network pharmacology analysis, and recognized as major anti-constipation constituents in Aloe vera. The validated quantitative method of the six active constituents in rat plasma exhibited good linearity, and lower limits of quantification (0.64-1.95 ng/mL). Aloin A, aloin B, aloeresin D and aloe-emodin exhibited better absorption and slower elimination rate, whereas the others, including aloesin and aloenin showed fast absorption and elimination in rat plasma after oral administration of Aloe vera. Aloin A and its isomer aloin B present similar T. This study will benefit understanding the contributions of those constituents for the anti-constipation effect of Aloe vera and also provide valuable information for its application in functional food development and clinics.

Topics: Aloe; Animals; Constipation; Emodin; Network Pharmacology; Plant Extracts; Rats; Tandem Mass Spectrometry

Although the approved hepatitis B virus (HBV)-polymerase inhibitors (e.g., lamivudine) often lead to drug-resistance, several natural products have shown promising efficacies. Though Aloe vera (AV) gel and its constituents are shown inhibitors of many viruses, their anti-HBV activity still remains elusive. We therefore, tested the anti-HBV potential of AV extract and its anthraquinones in hepatoma cells, including molecular docking, high-performance thin layer chromatography (HPTLC), and cytochrome P450 (CYP3A4) activation analyses. Our anti-HBV assays (HBsAg/HBeAg Elisa) showed maximal inhibition of viral antigens production by aloe-emodin (~83%) > chrysophanol (~62%) > aloin B (~61%) > AV extract (~37%) in HepG2.2.15 cells. Interestingly, the effect of aloe-emodin was comparable with lamivudine (~86%). Moreover, sequential treatment with lamivudine (pulse) followed by aloe-emodin (chase) enhanced the efficacy of monotherapy by ~12%. Docking (AutoDock Vina) of the anthraquinones indicated strong interactions with HBV-polymerase residues that formed stable complexes with high Gibbs's free energy. Further, identification of aloe-emodin and aloin B by validated HPTLC in AV extract strongly endorsed its anti-HBV potential. In addition, our luciferase-reporter gene assay of transfected HepG2 cells showed moderate induction of CYP3A4 by aloe-emodin. In conclusion, this is the first report on anti-HBV potential of AV-derived anthraquinones, possibly via HBV-polymerase inhibition. Of these, although aloin B exhibits novel antiviral effect, aloe-emodin appears as the most promising anti-HBV natural drug with CYP3A4 activating property towards its enhanced therapeutic efficacy.

Topics: Aloe; Anthraquinones; Antiviral Agents; Cell Line; Emodin; Hep G2 Cells; Hepatitis B; Hepatitis B virus; Humans; Phytotherapy; Plant Extracts

Topics: Aloe; Anthraquinones; Biphenyl Compounds; Cell Survival; Emodin; Flavonoids; Glycosylation; HT29 Cells; Humans; Hypoglycemic Agents; Methanol; Phenols; Phytochemicals; Picrates; Plant Extracts

Aloe vera (AV) is popular and has been commercialized as a beauty product, laxative, herbal medicine, the antimicrobial activity of AV is proven. The antiviral activity of AV however, has not been well documented except for a handful reports. Till date extraction of AV compounds is popularized using organic solvents, since the active components are effectively extracted in methanol. In the current work, we have employed a 5 min ultrasound based extraction for the effective extraction of aloin and aloe-emodin compounds from AV in water. This rapid, one-pot extraction process resulted in enhanced extraction of flavonoids and phenolics and enrichment of the aloin and aloe-emodin moieties in the ulrasonicated water extracts. The extracts were tested for their anti-influenza activity and, the results showed that the ultrasound extraction enabled the water extracts to show excellent anti influenza activity comparable to that seen in the methanolic extracts. Compared to the methanolic extracts which showed high cytotoxicity, the water extracts showed zero cytotoxicity. Spectrophotometric scans of the extracts confirmed the enrichment of the aloin and aloe emodin peaks in the ultrasonicated extracts of AV, suggesting their handiwork behind the anti-influenza activity. The demonstrated technique if appropriately implicated, would lead to promising solutions in the pharmaceutical pursuit against influenza virus.

Topics: Aloe; Animals; Anthraquinones; Antiviral Agents; Cell Line; Dogs; Emodin; Flavonoids; Madin Darby Canine Kidney Cells; Orthomyxoviridae; Phenol; Plant Extracts; Plant Leaves; Plants, Medicinal; Solvents; Ultrasonic Waves

There is an urgent need for the development of new, cheap, safe and highly effective drugs against African trypanosomiasis that affects both man and livestock in sub-Saharan Africa including Ethiopia. In the present study the exudate of Aloe gilbertii, an endemic Aloe species of Ethiopia, aloin, aloe-emodin and rhein were tested for their in vitro and in vivo antitrypanosomal activities against Trypanosoma congolense field isolate. Aloin was prepared from the leaf exudate of A. gilbertii by acid catalyzed hydrolysis. Aloe-emodin was obtained by oxidative hydrolysis of aloin, while rhein was subsequently derived from aloe-emodin by oxidation. In vitro trypanocidal activity tests were conducted on parasites obtained from infected mice, while mice infected with T. congolense were used to evaluate in vivo antitrypanosomal activity of the test substances.. Results of the study showed that all the test substances arrested parasites motility at effective concentration of 4.0 mg/ml within an incubation period ranging from 15 to 40 min. Moreover, the same concentration of the test substances caused loss of infectivity of the parasites to mice during 30 days observation period. Among the tested substances, rhein showed superior activity with minimum inhibitory concentration (MIC) of 0.4 mg/ml. No adverse reactions were observed when the test substances were administered at a dose of 2000 mg/kg. Rhein at doses of 200 and 400 mg/kg, and the exudate, aloin and aloe-emodin at a dose of 400 mg/kg reduced the level of parasitaemia significantly (P < 0.05) and improved anaemia.. The results obtained in this investigation indicate that aloin and its derivatives particularly rhein have the potential to be used as a scaffold for the development of safe and cost effective antitrypanosomal drugs that can be useful in the continuing fight against African trypanosomiasis.

Topics: Animals; Anthraquinones; Diminazene; Dose-Response Relationship, Drug; Emodin; Female; Mice; Molecular Structure; Random Allocation; Trypanocidal Agents; Trypanosoma congolense; Trypanosomiasis, African

By using transmission electron microscopy and high performance liquid chromatography, this paper studied the effects of enhanced UV-B radiation on the leaf anthraquinones content and cell ultrastructure of Aloe vera L. After treated with enhanced UV-B radiation 6 hours per day for 20 days, the total anthraquinone content, barbaloin content, and aloe-emondin content in A. vera leaves increased by 31.8%, 11.3%, and 22.0%, respectively, chloroplast envelope membrane was slightly damaged, but the structure of other organelles had no significant change. It was suggested that UV-B radiation could promote the accumulation of anthraquinone in A. vera leaves, but had less effects on the leaf cell ultrastructure.

Topics: Aloe; Anthracenes; Anthraquinones; Plant Leaves; Ultraviolet Rays

The aloe ingredients responsible for physiological effects and the concentrations required to exert their biological activities are not fully understood. This study compares the anti-inflammatory effects of aloin and aloe-emodin with other polyphenols. Our results demonstrated that aloe-emodin dose-dependently inhibited inducible nitric oxide synthase (iNOS) mRNA expression and nitric oxide (NO) production at 5-40 microM. In addition, the levels of cyclooxygenase-2 (COX-2) mRNA and prostaglandin E2 (PGE2) production were suppressed by 40 microM aloe-emodin. Aloin also suppressed the production of NO at 5-40 microM, although it did not suppress PGE2 production. The present results indicate that aloin and aloe-emodin possibly suppress the inflammatory responses by blocking iNOS and COX-2 mRNA expression. The anti-inflammatory effect of aloe-emodin was comparable to that of kaempferol and quercetin, indicating aloe-emodin as a possible key constituent responsible for the anti-inflammatory activity of aloe.

Topics: Aloe; Animals; Anthraquinones; Anti-Inflammatory Agents; Cell Line; Cell Survival; Cyclooxygenase 2; Dinoprostone; Emodin; Flavonols; Gene Expression Regulation, Enzymologic; Isoflavones; Lipopolysaccharides; Macrophages; Mice; Nitric Oxide; Nitric Oxide Synthase Type II; RNA, Messenger

The interactions of serum albumins such as human serum albumin (HSA) and bovine serum albumin (BSA) with emodin, rhein, aloe-emodin and aloin were assessed employing fluorescence quenching and absorption spectroscopic techniques. The results obtained revealed that there are relatively strong binding affinity for the four anthraquinones with HSA and BSA and the binding constants for the interactions of anthraquinones with HSA or BSA at 20 degrees C were obtained. Anthraquinone-albumin interactions were studied at different temperatures and in the presence of some metal ions. And the competition binding of anthraquinones with serum albumins was also discussed. The Stern-Volmer curves suggested that the quenching occurring in the reactions was the static quenching process. The binding distances and transfer efficiencies for each binding reactions were calculated according to the Föster theory of non-radiation energy transfer. Using thermodynamic equations, the main action forces of these reactions were also obtained. The reasons of the different binding affinities for different anthraquinone-albumin reactions were probed from the point of view of molecular structures.

Topics: Anthraquinones; Binding Sites; Drugs, Chinese Herbal; Emodin; Humans; Models, Molecular; Molecular Structure; Serum Albumin; Serum Albumin, Bovine

A procedure was developed for the determination of low levels of the anthraquinones aloe-emodin and aloin A (barbalin) in aloe products based on gas chromatography/mass spectrometry (GC/MS) of the trimethyl silyl (TMS) derivatives of these analytes in the presence of Chrysophanol used as internal standard. The method was used to analyze several aloe based commercial products (liquids, gels and solids). Wide variation in the level of these anthraquinones was observed among the different products. The method had a sensitivity of 0.005 ppm of aloe-emodin and 0.05 ppm of aloin.

Topics: Aloe; Anthraquinones; Emodin; Gas Chromatography-Mass Spectrometry; Indicators and Reagents; Reference Standards; Reproducibility of Results

Plants containing aloin A, aloe emodin, and structurally related anthraquinones have long been used as traditional medicines and in the formulation of retail products such as laxatives, dietary supplements, and cosmetics. Since a recent study indicated that topically applied aloe emodin increases the sensitivity of skin to UV light, we examined the events following photoexcitation of aloin A and aloe emodin. We determined that incubation of human skin fibroblasts with 20 microM aloe emodin for 18 h followed by irradiation with UV or visible light resulted in significant photocytotoxicity. This photocytotoxicity was accompanied by oxidative damage in both cellular DNA and RNA. In contrast, no photocytotoxicity was observed following incubation with up to 500 microM aloin A and irradiation with UVA light. In an attempt to explain the different photobiological properties of aloin A and aloe emodin, laser flash photolysis experiments were performed. We determined that the triplet state of aloe emodin was readily formed following photoexcitation. However, no transient intermediates were formed following photoexcitation of aloin A. Therefore, generation of reactive oxygen species and oxidative damage after irradiation of aloin A is unlikely. Although aloin A was not directly photocytotoxic, we found that human skin fibroblasts can metabolize aloin A to aloe emodin.

Topics: Animals; Anthraquinones; Cattle; Cells, Cultured; Dermatitis, Phototoxic; DNA; DNA Damage; Emodin; Fibroblasts; Humans; Light; Oxidative Stress; Photosensitivity Disorders; Ultraviolet Rays

To investigate the relationship between the antibacterial activity of aloe and its contents of anthaquinone compounds, measure and compale antibacterial activities of aloin and aloe-emodin, and analyse the effect of glycoside on the antibacterial activity of aloin.. The antibacterial activities of the extracts from the outer leaf of Aloe saponaria Haw, aloin and aloe-emodin against three Gram-negative and two Gram-positive bacteria were investigated with the method of agar diffusion. The antibacterial effect of aloin on E. coli was further studied with scanning electron microscopy.. The antibacterial activities of aloe showed to be dependent on the dose of anthraquinone, aloin (1 g x L(-1)) exhibited higher antibacterial activity [inhibition diameter > (7. 1 +/- 0.15) mm] than Aloe-emodin (inhibition diameter < 5.0 mm), and aloin changed the morphology of E. coli and damaged the outer cell structrue.. Anthraquinone compounds are the active antibacterial components in aloe and aloin is the main active compound. The glycoside makes it easy for aloin to invade cells and enhances its activity.

Topics: Aloe; Anthraquinones; Anti-Bacterial Agents; Bacillus subtilis; Drugs, Chinese Herbal; Emodin; Escherichia coli; Plant Leaves; Plants, Medicinal; Proteus vulgaris; Pseudomonas aeruginosa; Staphylococcus aureus

The contents of barbaloin (BA), isoBA, aloin-dimers A, B, C, D and aloe-emodin (AE) in aloe drinks were investigated. BA and isoBA were detected in 30 of the 31 samples at the levels of 120-570 micrograms/mL and 120-580 micrograms/mL, respectively. Aloin-dimers A, B, C and D were detected in 8 of the 31 samples at the levels of 12-38 micrograms/mL, 13-39 micrograms/mL, 11-36 micrograms/mL and 16-69 micrograms/mL, respectively. AE was detected in all of the 31 samples at the levels of 0.03-1.3 micrograms/mL. When aloe drinks were stored for 4 weeks at 5 degrees C after opening the bottle, decrease of BA and isoBA, and increase of AE and aloin-dimers A, B, C and D were observed in most cases. However, in a few aloe drinks, all of BA, isoBA, aloin-dimers A, B, C, D and AE decreased. In these drinks, the existence of aloin-trimer was elucidated by LC/MS analyses. These data suggested that BA in aloe drinks is converted to the dimer and then to the trimer during storage.

Topics: Aloe; Anthracenes; Anthraquinones; Emodin; Food Analysis; Food Preservation; Temperature; Time Factors

It has been proved that the Chinese herb Aloe vera L. var. chinensis (Haw.) Berger as well as its active components showed many important pharmacology activities. In order to find an easy and low-cost method to control the quality of the herb, a CZE method for the determination of the active components aloin and aloe-emodin in Aloe vera L. var. chinensis (Haw.) Berger was developed in this work. Under the buffer conditions of 24 mmol/L phosphate (pH 10.52), applied voltage of 15 kV and detector wavelength of 254 nm, baseline separation of the active compounds in Aloe vera L. var. chinensis (Haw.) Berger was achieved and the active components were quantitatively analyzed. The linear calibration equations of the two components are: Y= -0.140 + 57.2X (r = 0.997) for aloin and Y = -0.393 + 1.08 x 10(2) X (r = 0.999) for aloe-emodin respectively. In addition, the effects of buffer pH value and organic modifier on the migration behavior of the solutes were also investigated.

Topics: Aloe; Anthraquinones; Electrophoresis, Capillary; Emodin

Aloe contains abundant aloin, a C-glycoside derivative of anthraquinone. Based on recent reports indicating that the water extract of Aloe enhances the ethanol oxidation rate and also that quinones, in general, have a functional role in elevating the alcohol oxidation rate in vivo, we have attempted to identify the quinone derivative contained in Aloe that could increase the alcohol oxidation rate. Upon oral administration of aloin (300 mg/kg) given 12 hr prior to the administration of alcohol (3.0 g/kg), the blood alcohol area under the curve (AUC) was found to be decreased significantly (by 40%). This was supported by increases in the rates of blood alcohol elimination and the disappearance of alcohol from the body by 45 and 50%, respectively. Analysis of hepatic triglyceride (TG) levels revealed that both the ethanol and the aloin treatment alone significantly increased the TG levels in a comparable manner; however, the level obtained by the combined treatment of aloin and ethanol was not statistically different from that produced by either treatment alone. The levels of serum L-aspartate:2-oxoglutarate aminotransferase (AST) and L-alanine:2-oxoglutarate aminotransferase (ALT) activities were not increased by acute alcohol intoxication, aloin alone, or by the combined treatment of alcohol and aloin. Pretreatments with aloe-emodin, the anthraquinone aglycone of aloin, resulted in a significantly decreased blood alcohol AUC and an increase in the rate of ethanol disappearance. These results suggested that when the aloin localized primarily in the skin of Aloe is ingested, aloe-emodin (the quinone aglycone) may be released, and the released quinone may produce acceleration of the ethanol metabolism rate in vivo.

Topics: Alanine Transaminase; Alcoholic Intoxication; Aloe; Animals; Anthraquinones; Aspartate Aminotransferases; Emodin; Ethanol; Female; Kinetics; Liver; Metabolic Clearance Rate; Oxidation-Reduction; Plants, Medicinal; Rats; Rats, Sprague-Dawley; Triglycerides

Orally administered barbaloin (100 mg/kg) did not induce any diarrhea in male Wistar rats, in spite of severe diarrhea with sennoside B (40 mg/kg). Also, in gnotobiote rats mono-associated with Peptostreptococcus intermedius, a human intestinal anaerobe capable of reducing sennidins to rhein anthrone, barbaloin did not induce diarrhea; the faecal water content (71.9%) 8 h after the administration of barbaloin was not increased, compared with that (73.9%) just before the treatment. However, severe diarrhea was induced with barbaloin in gnotobiote rats mono-associated with Eubacterium sp. strain BAR, another human intestinal anaerobe capable of transforming barbaloin to aloe-emodin anthrone; the faecal water content was significantly increased to 85.5% 8 h after the administration, from 73.2% before the treatment. At this time, barbaloin was transformed to aloe-emodin anthrone in the feces from the gnotobiote rats mono-associated with the strain BAR, but not in feces from the conventional rats or the gnotobiote rats mono-associated with P. intermedius. These facts indicate that barbaloin is inactive as a laxative itself but is activated to aloe-emodin anthrone, a genuine purgative component, by Eubacterium sp. strain BAR.

Topics: Animals; Anthracenes; Anthraquinones; Cathartics; Culture Media; Diarrhea; Emodin; Eubacterium; Feces; Intestines; Male; Rats; Rats, Wistar

Aloe-emodin-9-anthrone(AE-anthrone), produced from barbaloin in the rat large intestine, caused not only an increase in the intestinal water content but also stimulated mucus secretion. This might play an important role in the occurrence of diarrhea. It was demonstrated that the amount of AE-anthrone produced in the rat large intestine(maximal amount: 568 micrograms/rat at 4 h after injection) was enough to cause both of these effects, which were observed following intracecal administration of barbaloin (31.1 mg/kg). These results together with our previous data, which showed a relationship between increase in the intestinal water content and the stimulation of peristalsis, confirm that AE-anthrone is the principal agent responsible for the cathartic effect of barbaloin. We also propose that the increase in water content is a more important factor than stimulation of peristalsis in the induction of diarrhea by barbaloin.

Topics: Aloe; Animals; Anthracenes; Anthraquinones; Body Water; Cathartics; Chromatography, Thin Layer; Densitometry; Emodin; Feces; Intestinal Mucosa; Male; Mucus; Peristalsis; Plants, Medicinal; Rats; Rats, Wistar

Topics: Aloe; Anthracenes; Anthraquinones; Emodin; Humans