This study sought to clarify the molecular location and the interaction between mitoxantrone and mitoxantrone transforsomes. The anthraquinone of mitoxantrone, a heterocyclic ring that intercalates in the lipid of bilayer, was determined by UV-spectrophotometry and electron probes scan microscopy. Two aminoethylamino side-chains of the drugs fit to the phosphates of lecithin were determined by 8-value, thus the interaction with lecithin was substantiated. Differential scanning calorimetry confirmed that mitoxantrone has remarkable stabilizing effect on the mitoxantrone transforsomes membrane. The mitoxantrone binds tightly to lecithin. So a high degree of encapsulation efficiency and the sustained-release character of mitoxantrone transforsomes are verified.
Anthraquinones ; chemistry ; Calorimetry, Differential Scanning ; Delayed-Action Preparations ; chemistry ; Lecithins ; chemistry ; Mitoxantrone ; chemistry ; Spectrophotometry

OBJECTIVETo probe into the influences of different granule sizes and to prepare procedures on rational clinical usage of rhubarb based on chemical equivalence.

METHODThe effects of particle size, extract solvent, extract time and repeat times, and pre-extract or pro-extract of rhubarb on the extract amounts of the anthraquinones (AQs) were compared.

RESULTThe different prepare procedures investigated in the paper revealed significant influence on the extract amounts of the AQs and those extracts were not chemical equivalent. Ethanol extracted more AQs than water did, when other conditions were same. When extracted with water, the rhubarb of piece size 0.8-1.2 cm could extract relatively high amount of AQs nearly equal to superfine grinded powders, and the former was cheap. The water extraction of AQs showed an increasing trend with the extraction time extended. And pro-extract manner with water could extract more AQs than pre-extract manner with a extraction time of 30, 60 min. The water extraction of AQs repeated two times exceeded half of the amount of totally six times. When extracted with ethanol, the rhubarb of fine powders could extract relatively high amount of AQs nearly equal to superfine grinded powders. And pre-extract manner with ethanol could extract more AQs than pro-extract manner. The ethanol extraction of AQs increased in 30 min and then increased slower. The ethanol extraction of AQs repeated two times exceeded 70% of the amount of totally six times. So, the optimal conditions for water extraction rhubarb were pro-extract, two times repeated and 30 min per time; and the optimal conditions for ethanol extract were pre-extract, two times repeated and 30 min per time.

CONCLUSIONThe different prepare procedures showed significant influence on the extraction of rhubarb AQs. There is great need to establish a good usage practice (GUP) for Chinese Materia Medica to maintain rational clinical usage.

Anthraquinones ; chemistry ; Rheum ; chemistry

The positive response to tamoxifen in ERa-positive breast cancer patients is usually of a short duration as many of the patients eventually develop resistance. Our preliminary results show that aloe emodin extracted from the leaves of the Aloe barbadensis Miller demonstrated a cytotoxicity that is selective to ERa-positive breast cancer cells (MCF-7), but not to ERa-negative breast cancer cells (MDA-MB-231) and to the control cells (MCF- 10A). The objective of this study was to test the hypothesis that aloe emodin may enhance the response of MCF-7 cells to treatment with tamoxifen. MCF-7 cells were treated with aloe emodin alone, tamoxifen alone or a combination of emodin and tamoxifen, at their respective IC50 concentrations and at different time points of 24 hours, 48 hours and 72 hours. The respective IC50s were the concentrations of aloe emodin and tamoxifen required to achieve 50% inhibition of the cells in the study. Cell viability and apoptosis were determined using trypan blue exclusion and DNA fragmentation assays, respectively. The involvement of RAS/MEKs/ERKs genes of MAPK signalling pathways with aloe emodin was determined using QuantiGene 2.0 Plex assay. Data was evaluated using the one-way ANOVA test. Our findings showed that aloe emodin enhanced the cytotoxicity of tamoxifen on MCF-7 cells through apoptosis by downregulation of MEK1/2 genes. Our research may provide a rational basis for further in vivo studies to verify the efficacy of a combination of aloe emodin and tamoxifen on the viability of ERa-positive-breast cancer cells.
Anthraquinones ; Breast Neoplasms

OBJECTIVETo establish a method for determining the content of primary chemical constituents in the leaves of Cassia angustifolia.

METHODThe HPLC with Diamonsil C18 (4.6 mm x 250 mm, 5 microm) column was used , acetonitrile-1% acetic acid (10:90-15: 85-18: 82-20: 80-25: 75) in a gradient manner was used as a mobile phase, with flow rate of 1 mL x min(-1), column temperature at 40 degrees C and detection wavelength at 270 nm.

RESULTThe results showed that 5 effective components all separated well and showed good linearity.

CONCLUSIONThe method was proved to be rapid, sensitive, accurate, credible and repeatable. It can be applied to quality control of Folium Sennae.

Anthraquinones ; chemistry ; Apigenin ; chemistry ; Chromatography, High Pressure Liquid ; methods ; Glucosides ; chemistry ; Naphthalenes ; chemistry ; Reproducibility of Results ; Senna Extract ; Senna Plant ; chemistry ; Temperature

Angucyclines/angucyclinones are a large group of polycyclic aromatic polyketides and their producers are widely distributed in nature. This family of natural products attracts great attention because of their diverse biological activities and unique chemical structures. With the development of synthetic biology and the exploitation of the actinomycetes from previously unexplored environments, angucyclines/angucyclinones-like natural products with new skeletons were continuously discovered, thus enriching the structural diversity of this family. In this review we summarize the new angucyclines/angucyclinones analogues discovered in the last decade (2010-2020) by using different strategies, such as changing cultivation conditions, genetic modification, genome mining, bioactivity-guided compound isolation, and fermentation of actinomycetes from underexplored environments. We also discuss the role of synthetic biology in the discovery and development of new compounds of the angucycline/angucyclinone family.
Anthraquinones ; Biological Products ; Polyketides ; Streptomyces

Anti-Helicobacter pylori activity guided fractionation led to the isolation of five anthraquinones, two stilbenes and one naphthoquinone from the EtOAc fraction of Polygonum cuspidatum, using silica gel column chromatography, Sephadex-LH20, MPLC and recrystallization. The chemical structures were identified to be physcion (1), emodin (2), anthraglycoside B (3), trans-resveratrol (4), anthraglycoside A (5), polydatin (6), 2-methoxy-6-acetyl-7-methyljuglone (7) and citreorosein (8) by UV, ¹H-NMR, ¹³C-NMR and mass spectrometry. Anti-Helicobacter pylori activity including MIC values of each compound was evaluated. All of the isolates exhibited anti-H. pylori activity of which MIC values were lower than that of a positive control, quercetin. Compounds 2 and 7 showed potent growth inhibitory activity. Especially, a naphthoquinone, compound 7 displayed most potent antibacterial activity with MIC₅₀ value of 0.30 µM and MIC₉₀ value of 0.39 µM. Although anti-H. pylori activity of this plant was previously reported, this is the first report on that of compounds isolated from this species. From these findings, P. cuspidatum roots or its isolates may be useful for H. pylori infection and further study is needed to elucidate mechanism of action.
Anthraquinones ; Chromatography ; Emodin ; Fallopia japonica* ; Mass Spectrometry ; Plants ; Polygonum* ; Quercetin ; Silica Gel ; Stilbenes

OBJECTIVETo identify the endophyte strain E8 with high activity from Curcuma wenyujin and study its secondary metabolites.

METHODThe strain E8 was identified by morphological observation and ITS sequence analysis. Manifold chromatographic methods were used to separate and purify the chemical constituents of fermentation broth from strain E8, and their structures were identified by physiochemical properties and spectral data.

RESULTThe strain E8 belongs to P. oxalicum. Four compounds were isolated from the fermentation broth of this strain and elucidated as chrysophanol, emodin, secalonic acid A and beta-sitosterol.

CONCLUSIONThe endophyte P. oxalicum was isolated from medicinal plant Curcuma wenyujin for the first time. Four compounds were first isolated from endophytic fungus in C. wenyujin. Thus, microbial fermentation is a new access for these compounds production.

Anthraquinones ; analysis ; Curcuma ; microbiology ; Emodin ; analysis ; Fermentation ; Penicillium ; genetics ; isolation & purification ; metabolism ; Sitosterols ; analysis ; Xanthones ; analysis

In order to study the storage and period of validity of emodin standard solution and chrysophanol standard solution in this study, the content of emodin and chrysophanol was determined by HPLC through classical constant temperature test, and the change rule of the content of the standard solution was studied, which could be applied to standardize the management of the standard substance of traditional Chinese medicine. The results showed that the content of emodin and chrysophanol standard solution matched with the first order reaction rule. Under the storage condition of 10 °C, the change rate constant of emodin and chrysophanol were Ke=4.661 7×10⁻⁷ and Kc=4.438 9×10⁻⁷, respectivedy; and the period of validity of emodin standard solution and chrysophanol standard solution were 1 806 d and 1 896 d respectively. The determination and standardization of the period of validity of the standard solution will not only help to reduce the loss of the standard substance and save the cost of drug testing, but also help to standardize the use of the standard substance, which will contrite to obtain more accurate and satisfactory experimental results, and provide a basis for the setting of the storage period and standardized management of the reference solution of Chinese medicine.
Anthraquinones ; analysis ; Chromatography, High Pressure Liquid ; Drugs, Chinese Herbal ; Emodin ; analysis

This study aims to establish an ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry(UPLC-Q-TOF-MS) method for the determination of emodin-8-O-β-D-glucoside(EG) and its metabolites in plasma, and to investigate the toxicokinetics(TK) behavior of them in rats. To be specific, the TK of EG and its metabolites from the first to the last administration in the repeated dose toxicity study was determined, and the kinetic parameters were calculated. The exposure of EG prototype and metabolites in rat plasma after oral administration of different doses of EG was evaluated. The result showed that the prototype of EG and its metabolites aloe-emodin-8-O-β-D-glucoside, emodin, aloe-emodin, and hydroxyemodin could be detected in rats after oral administration of high-, medium-, and low-dose EG. The area under the curve(AUC) of the prototype and metabolites after the first and last administration was in positive correlation with the dose. The time to the maximum concentration(T_(max)) of EG and metabolites in the three administration groups was <6 h, and the longest in vivo residence time was 12 h. The T_(max) and in vivo residence time of EG were prolonged with the increase in the dose. The metabolites emodin, aloe-emodin, and hydroxyemodin all had two peaks. Both hydroxyemodin and aloe-emodin exhibited increased plasma exposure, slow metabolism, and accumulation in vivo. In addition, aloe-emodin-8-O-β-D-glucoside and emodin disappeared with the increase in dose, suggesting the change of the metabolic pathway of EG in vivo in the case of high-dose administration. The mechanism of high-dose EG in vivo needs to be further explored. This study preliminarily elucidates the TK behavior of EG in rats, which is expected to support clinical drug use.
Animals ; Anthraquinones ; Chromatography, High Pressure Liquid/methods* ; Emodin/toxicity* ; Glucosides/toxicity* ; Mass Spectrometry ; Rats ; Toxicokinetics

Methanol total dried extract of the root of Nho dong (Morinda longissima Y.Z.Ruan, Rubiaceae) collected in Chieng An commune, Son La town, Son La province was analyzed. From the fractions n.6 and n.18 of column chromatography with Silicagel adsorption and developing solvents Chloroform/Methanol (9/1) system, by thin layer chromatography, an anthranoid substance (CP4) was isolated. Spectral analysis showed its structure as its is 1,3- dihydroxy,4-methyl ethyl ether anthraquinone, first time found in nho dong
Anthraquinones ; Medicine, Traditional ; plants, medicinal ; Plant Roots ;