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Fulltext Establishing GPCR Targets of hMAO Active Anthraquinones from Cassia obtusifolia Linn Seeds Using In Silico and In Vitro Methods

Paudel P, Seong SH, Fauzi FM, Bender A, Jung HA, Choi JS

ACS Omega, 2020 Apr 07;5(13):7705-7715.
PMID: 32280914 DOI: 10.1021/acsomega.0c00684

The present study examines the effect of human monoamine oxidase active anthraquinones emodin, alaternin (=7-hydroxyemodin), aloe-emodin, and questin from Cassia obtusifolia Linn seeds in modulating human dopamine (hD1R, hD3R, and hD4R), serotonin (h5-HT1AR), and vasopressin (hV1AR) receptors that were predicted as prime targets from proteocheminformatics modeling via in vitro cell-based functional assays, and explores the possible mechanisms of action via in silico modeling. Emodin and alaternin showed a concentration-dependent agonist effect on hD3R with EC50 values of 21.85 ± 2.66 and 56.85 ± 4.59 μM, respectively. On hV1AR, emodin and alaternin showed an antagonist effect with IC50 values of 10.25 ± 1.97 and 11.51 ± 1.08 μM, respectively. Interestingly, questin and aloe-emodin did not have any observable effect on hV1AR. Only alaternin was effective in antagonizing h5-HT1AR (IC50: 84.23 ± 4.12 μM). In silico studies revealed that a hydroxyl group at C1, C3, and C8 and a methyl group at C6 of anthraquinone structure are essential for hD3R agonist and hV1AR antagonist effects, as well as for the H-bond interaction of 1-OH group with Ser192 at a proximity of 2.0 Å. Thus, based on in silico and in vitro results, hV1AR, hD3R, and h5-HT1AR appear to be prime targets of the tested anthraquinones.

Matched MeSH terms: Anthraquinones
Fulltext Involvement of intracellular calcium and MAPK in aloe emodin induced anti-proliferative in MCF-7

Indah M Amin, Mohd Ridzuan Hamid, Dayang Zahidah A. Othman, Rosfaiizah Siran, Siti Hamimah S.A. Kadir, Narimah AH Hasani

ASM Science Journal, 2014;8(2):165-173.
MyJurnal

Aloe emodin, an anthraquinone of Aloe barbadensis Miller has been shown to have more cytotoxic effect in
different kinds of human cancer cell lines compared to normal. Accordingly, we found it to selectively inhibit
the proliferation of oestrogen-receptor-positive-(ER+)-breast cancer cells, MCF-7; but not controls cells,
MCF-10A. However, its precise mechanism is not well understood. Several studies have shown that there is
evidence of increased intracellular calcium (Ca2+), both at early and late stage of apoptosis which associated
with the down-regulation of ERK1/2 proliferative pathway. Therefore, we aim to elucidate the involvement
of intracellular Ca2+ in aloe emodin induced apoptosis on MCF-7. Apoptotic morphological changes were
observed under fluorescence microscope. The involvement of cytoplasmic Ca2+ and MAPKs were investigated
using Fluo-4 intracellular Ca2+ imaging and QuantiGene 2.0 Plex assay, respectively. IC50 of aloe emodin
(80 μM) at 72 hours incubation was used. Data were evaluated using the one-way or two-way ANOVA tests.
Our results indicated that aloe emodin at IC50 80µM induced apoptosis on MCF-7 through the association of
intracellular Ca2+ signalling. This observation include a significant increased (p

Matched MeSH terms: Anthraquinones
Damnacanthal: a promising compound as a medicinal anthraquinone

Abu N, Ali NM, Ho WY, Yeap SK, Aziz MY, Alitheen NB

Anticancer Agents Med Chem, 2014 Jun;14(5):750-5.
PMID: 24164045

The Noni fruit, or scientifically known as Morinda citrifolia can be found in various parts of the world, especially in the pacific region. It is a small evergreen bushy-like tree originated from the Rubiaceae family. The plant has been used by polynesians as a medicinal herb for more than 2000 years. A substantial amount of phytochemicals can be found in the roots of this plant. Among all, damnacanthal has been found to be the most interesting, versatile and potent compound. Damnacanthal or chemically known as,3- hydroxy-1-methoxyanthraquinone-2-caboxaldehyde (C16H10O5), appears as pale yellow crystals with a melting point of 210-211 °C. This compound is of particular interest due to its striking pharmacological properties. Damnacanthal was shown to inhibit the oncogene Ras, p56lck tyrosine kinase, NF-KB pathway and induce apoptosis in vitro. This review aims to discuss the biological properties of damnacanthal, specifically on its anti-cancer activity that has been reported.

Matched MeSH terms: Anthraquinones/pharmacology; Anthraquinones/therapeutic use*; Anthraquinones/chemistry
Fulltext Confocal laser scanning microscopy study of dentinal tubules in dental caries stained with alizarin red

Marzuki, A.F., Masudi, S.M.

Archives of Orofacial Sciences, 2008;3(1):2-6.
MyJurnal

Dentin morphology and the lesion found in dental caries have been studied for many years. It was first observed under optical microscopy, and later using electron microscopy. Confocal laser scanning microscopy (CLSM) applied with several fluorescent dyes such as alizarin red to see normal dentinal tubules. However, as far as authors aware, the CLSM studies of dentinal tubules in human caries using alizarin red is rare. The aim of this study is to examine histopathological and morphological changes in dentinal tubules of dentin caries stained with alizarin red using CLSM. Fifteen extracted carious teeth (premolar or molar) was collected and fixed in neutral formalin solution buffered with phosphate buffer, rinsed and stored in calcium free phosphate buffer saline (PBS) at 4°C. The specimens were dehydrated and embedded in resin. Longitudinal or cross sections were cut and polished and then stained with alizarin red S (100 μg/ml) in 0.5 M HCl solution for 24-48 hour at 37°C. After dehydration specimens were mounted on glass slide and examined under CLSM using epi-flourescent mode or transmission light mode with wave length of 512 nm. The images of dentinal tubules were taken serially and optimum images of three-dimensional structures were reconstructed using software of CLSM. Histopathological changes of dentinal tubules in human caries showed area of demineralized dentin, translucent zone, and normal area. The dentinal tubules were thin and had numerous branches. In conclusion, confocal microscopy revealed Study shows that confocal microscopy revealed histopathological changes in dentinal tubules affected by carious lesions.

Matched MeSH terms: Anthraquinones
Expression profile of genes modulated by Aloe emodin in human U87 glioblastoma cells

Haris K, Ismail S, Idris Z, Abdullah JM, Yusoff AA

Asian Pac J Cancer Prev, 2014;15(11):4499-505.
PMID: 24969876

Glioblastoma, the most aggressive and malignant form of glioma, appears to be resistant to various chemotherapeutic agents. Hence, approaches have been intensively investigated to targeti specific molecular pathways involved in glioblastoma development and progression. Aloe emodin is believed to modulate the expression of several genes in cancer cells. We aimed to understand the molecular mechanisms underlying the therapeutic effect of Aloe emodin on gene expression profiles in the human U87 glioblastoma cell line utilizing microarray technology. The gene expression analysis revealed that a total of 8,226 gene alterations out of 28,869 genes were detected after treatment with 58.6 μg/ml for 24 hours. Out of this total, 34 genes demonstrated statistically significant change (p<0.05) ranging from 1.07 to 1.87 fold. The results revealed that 22 genes were up-regulated and 12 genes were down-regulated in response to Aloe emodin treatment. These genes were then grouped into several clusters based on their biological functions, revealing induction of expression of genes involved in apoptosis (programmed cell death) and tissue remodelling in U87 cells (p<0.01). Several genes with significant changes of the expression level e.g. SHARPIN, BCAP31, FIS1, RAC1 and TGM2 from the apoptotic cluster were confirmed by quantitative real-time PCR (qRT-PCR). These results could serve as guidance for further studies in order to discover molecular targets for the cancer therapy based on Aloe emodin treatment.

Matched MeSH terms: Anthraquinones/pharmacology*
Effects of Damnacanthal and Nordamnacanthal on Proliferation, Apoptosis, and Migration of Oral Squamous Cell Carcinoma Cells

Shaghayegh G, Alabsi AM, Ali-Saeed R, Ali AM, Vincent-Chong VK, Ismail NH, et al.

Asian Pac J Cancer Prev, 2017 Dec 29;18(12):3333-3341.
PMID: 29286228

Cancer is one of the most common causes of death in the developed world, with one-third of people diagnosed with
cancer during their lifetime. Oral cancer commonly occurs involving the buccal mucosa (cheeks), tongue, floor of the
mouth and lip. It is one of the most devastating and disfiguring of malignancies. Morinda citrifolia L., commonly known
as ‘noni’, belongs to the Rubiaceae family. It is native to the Pacific islands, Hawaii, Caribbean, Asia and Australia.
The plant displays broad curative effects in pharmacological studies. Damnacanthal (DAM) and Nordamnacanthal
(NDAM), anthraquinone compounds isolated from the roots of Morinda citrifolia L., has been used for the treatment
of several chronic diseases including cancer. The objectives of this study were to evaluate cytotoxicity, morphological
changes, cell death mode (apoptosis/necrosis), and cell migration induced by DAM and NDAM on the most common
type of oral cancer, oral squamous cell carcinoma (OSCC)cells. Anti-proliferative effects of these compounds against
OSCC cell lines were determined by MTT assay. The mode of cell death was analysed by phase contrast and fluorescent
microscopy as well as flow cytometry. In addition, cell migration was assessed. The results showed that DAM and
NDAM exerted cytotoxicity against OSCC cells with IC50 values of 1.9 to >30 μg/ml after 72 h treatment. Maximum
growth inhibition among the tested cell lines for both compounds was observed in H400 cells, and thus it was selected
for further study. The study demonstrated inhibition of H400 OSCC cell proliferation, marked apoptotic morphological
changes, induction of early apoptosis, and inhibition of cell migration by DAM and NDAM. Therefore, this information
suggests that these compounds from noni have potential for used as anti tumor agents for oral cancer therapy.

Matched MeSH terms: Anthraquinones/pharmacology*
Fulltext Subchronic toxicity, immunoregulation and anti-breast tumor effect of Nordamnacantal, an anthraquinone extracted from the stems of Morinda citrifolia L

Abu N, Zamberi NR, Yeap SK, Nordin N, Mohamad NE, Romli MF, et al.

BMC Complement Altern Med, 2018 Jan 27;18(1):31.
PMID: 29374471 DOI: 10.1186/s12906-018-2102-3

BACKGROUND: Morinda citrifolia L. that was reported with immunomodulating and cytotoxic effects has been traditionally used to treat multiple illnesses including cancer. An anthraquinone derived from fruits of Morinda citrifolia L., nordamnacanthal, is a promising agent possessing several in vitro biological activities. However, the in vivo anti-tumor effects and the safety profile of nordamnacanthal are yet to be evaluated.
METHODS: In vitro cytotoxicity of nordamnacanthal was tested using MTT, cell cycle and Annexin V/PI assays on human MCF-7 and MDA-MB231 breast cancer cells. Mice were orally fed with nordamnacanthal daily for 28 days for oral subchronic toxicity study. Then, the in vivo anti-tumor effect was evaluated on 4T1 murine cancer cells-challenged mice. Changes of tumor size and immune parameters were evaluated on the untreated and nordamnacanthal treated mice.
RESULTS: Nordamnacanthal was found to possess cytotoxic effects on MDA-MB231, MCF-7 and 4T1 cells in vitro. Moreover, based on the cell cycle and Annexin V results, nordamnacanthal managed to induce cell death in both MDA-MB231 and MCF-7 cells. Additionally, no mortality, signs of toxicity and changes of serum liver profile were observed in nordamnacanthal treated mice in the subchronic toxicity study. Furthermore, 50 mg/kg body weight of nordamncanthal successfully delayed the progression of 4T1 tumors in Balb/C mice after 28 days of treatment. Treatment with nordamnacanthal was also able to increase tumor immunity as evidenced by the immunophenotyping of the spleen and YAC-1 cytotoxicity assays.
CONCLUSION: Nordamnacanthal managed to inhibit the growth and induce cell death in MDA-MB231 and MCF-7 cell lines in vitro and cease the tumor progression of 4T1 cells in vivo. Overall, nordamnacanthal holds interesting anti-cancer properties that can be further explored.

Matched MeSH terms: Anthraquinones/pharmacology*; Anthraquinones/toxicity; Anthraquinones/chemistry
Fulltext Decolourisation Capabilities of Ligninolytic Enzymes Produced by Marasmius cladophyllus UMAS MS8 on Remazol Brilliant Blue R and Other Azo Dyes

Sing NN, Husaini A, Zulkharnain A, Roslan HA

Biomed Res Int, 2017;2017:1325754.
PMID: 28168194 DOI: 10.1155/2017/1325754

Marasmius cladophyllus was examined for its ability to degradatively decolourise the recalcitrant dye Remazol Brilliant Blue R (RBBR) and screened for the production of ligninolytic enzymes using specific substrates. Monitoring dye decolourisation by the decrease in absorbance ratio of A592/A500 shows that the decolourisation of RBBR dye was associated with the dye degradation. Marasmius cladophyllus produces laccase and lignin peroxidase in glucose minimal liquid medium containing RBBR. Both enzyme activities were increased, with laccase activity recorded 70 times higher reaching up to 390 U L-1 on day 12. Further in vitro RBBR dye decolourisation using the culture medium shows that laccase activity was correlated with the dye decolourisation. Fresh RBBR dye continuously supplemented into the decolourised culture medium was further decolourised much faster in the subsequent round of the RBBR dye decolourisation. In vitro dye decolourisation using the crude laccase not only decolourised 76% of RBBR dye in just 19 hours but also decolourised 54% of Orange G and 33% of Congo red at the same period of time without the use of any exogenous mediator. This rapid dye decolourisation ability of the enzymes produced by M. cladophyllus thus suggested its possible application in the bioremediation of dye containing wastewater.

Matched MeSH terms: Anthraquinones/metabolism*
Cytochrome P450 2C9-natural antiarthritic interactions: Evaluation of inhibition magnitude and prediction from in vitro data

Tan BH, Ahemad N, Pan Y, Palanisamy UD, Othman I, Yiap BC, et al.

Biopharm Drug Dispos, 2018 Apr;39(4):205-217.
PMID: 29488228 DOI: 10.1002/bdd.2127

Many dietary supplements are promoted to patients with osteoarthritis (OA) including the three naturally derived compounds, glucosamine, chondroitin and diacerein. Despite their wide spread use, research on interaction of these antiarthritic compounds with human hepatic cytochrome P450 (CYP) enzymes is limited. This study aimed to examine the modulatory effects of these compounds on CYP2C9, a major CYP isoform, using in vitro biochemical assay and in silico models. Utilizing valsartan hydroxylase assay as probe, all forms of glucosamine and chondroitin exhibited IC50 values beyond 1000 μM, indicating very weak potential in inhibiting CYP2C9. In silico docking postulated no interaction with CYP2C9 for chondroitin and weak bonding for glucosamine. On the other hand, diacerein exhibited mixed-type inhibition with IC50 value of 32.23 μM and Ki value of 30.80 μM, indicating moderately weak inhibition. Diacerein's main metabolite, rhein, demonstrated the same mode of inhibition as diacerein but stronger potency, with IC50 of 6.08 μM and Ki of 1.16 μM. The docking of both compounds acquired lower CDOCKER interaction energy values, with interactions dominated by hydrogen and hydrophobic bondings. The ranking with respect to inhibition potency for the investigated compounds was generally the same in both in vitro enzyme assay and in silico modeling with order of potency being diacerein/rhein > various glucosamine/chondroitin forms. In vitro-in vivo extrapolation of inhibition kinetics (using 1 + [I]/Ki ratio) demonstrated negligible potential of diacerein to cause interaction in vivo, whereas rhein was predicted to cause in vivo interaction, suggesting potential interaction risk with the CYP2C9 drug substrates.

Matched MeSH terms: Anthraquinones/pharmacology
Rapid bioremediation of Alizarin Red S and Quinizarine Green SS dyes using Trichoderma lixii F21 mediated by biosorption and enzymatic processes

Adnan LA, Sathishkumar P, Yusoff AR, Hadibarata T, Ameen F

Bioprocess Biosyst Eng, 2017 Jan;40(1):85-97.
PMID: 27663440 DOI: 10.1007/s00449-016-1677-7

In this study, a newly isolated ascomycete fungus Trichoderma lixii F21 was explored to bioremediate the polar [Alizarin Red S (ARS)] and non-polar [Quinizarine Green SS (QGSS)] anthraquinone dyes. The bioremediation of ARS and QGSS by T. lixii F21 was found to be 77.78 and 98.31 %, respectively, via biosorption and enzymatic processes within 7 days of incubation. The maximum biosorption (ARS = 33.7 % and QGSS = 74.7 %) and enzymatic biodegradation (ARS = 44.1 % and QGSS = 23.6 %) were observed at pH 4 and 27 °C in the presence of glucose and yeast extract. The laccase and catechol 1,2-dioxygenase produced by T. lixii F21 were involved in the molecular conversions of ARS and QGSS to phenolic and carboxylic acid compounds, without the formation of toxic aromatic amines. This study suggests that T. lixii F21 may be a good candidate for the bioremediation of industrial effluents contaminated with anthraquinone dyes.

Matched MeSH terms: Anthraquinones/metabolism*
Iridoids and anthraquinones from the Malaysian medicinal plant, Saprosma scortechinii (Rubiaceae)

Ling SK, Komorita A, Tanaka T, Fujioka T, Mihashi K, Kouno I

Chem Pharm Bull (Tokyo), 2002 Aug;50(8):1035-40.
PMID: 12192133

A further investigation of the leaves and stems of Saprosma scortechinii afforded 13 compounds, of which 10 are new compounds. These were elucidated as the bis-iridoid glucosides, saprosmosides G (1) and H (2), the iridoid glucoside, 6-O-epi-acetylscandoside (3), and the anthraquinones, 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone (4), 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-beta-primeveroside (5), 1,3-dihydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-beta-primeveroside (6), 1,3,6-trihydroxy-2-methoxymethyl-9,10-anthraquinone (7), 1-methoxy-3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (8), 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone 3-O-beta-primeveroside (9), and 3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (10). Structure assignments for all compounds were established by means of mass and NMR spectroscopies, chemical methods, and comparison with published data. The new anthraquinones were derivatives of munjistin and lucidin.

Matched MeSH terms: Anthraquinones/isolation & purification*; Anthraquinones/chemistry
Morindone as a potential therapeutic compound targeting TP53 and KRAS mutations in colorectal cancer cells

Chee CW, Mohd Hashim N, Nor Rashid N

Chem Biol Interact, 2024 Apr 01;392:110928.
PMID: 38423379 DOI: 10.1016/j.cbi.2024.110928

There is an increasing demand for anticancer agent in treating colorectal cancer (CRC) with frequently mutated TP53 and KRAS genes. Phytochemical compounds are suitable as chemoprevention for CRC since dietary factor is a major risk factor. Anthraquinones from Morinda citrifolia L. were previously reported with various pharmacological properties. Various in vitro experiments were conducted to investigate the effects of two anthraquinones: damnacanthal and morindone on the cell proliferation, cell cycle, apoptosis, gene expression and protein expression in two CRC cells: HCT116 and HT29. Real-time monitoring of CRC cells showed that both anthraquinones exerted significant anti-proliferative effects in a dose- and time-dependent manner. Next, cell cycle analysis revealed an increase in the percentage of CRC cells in the G1 phase under anthraquinones treatment. Fluorescence microscopy also showed an increment of apoptotic cells under anthraquinones' treatment. siRNA transfection was conducted to evaluate the mediating effect of gene knockdown on mutated TP53 and KRAS in CRC cells. Before transfection, qRT-PCR analysis showed that only morindone downregulated the gene expression of mutated TP53 and KRAS and then further downregulated them after transfection. Both damnacanthal and morindone treatments further downregulated the expression of these two genes but upregulated at the protein expression level. Furthermore, gene knockdown also sensitised CRC cells to both damnacanthal and morindone treatments, resulting in lowered IC50 values. The accumulation of cells at the G1 phase was reduced after gene knockdown but increased after damnacanthal and morindone treatments. In addition, gene knockdown has increased the number of apoptotic cells in both cell lines and further increment was observed after anthraquinone treatment. In conclusion, morindone could be a competitive therapeutic agent in CRC by exhibiting multiple mechanism of anti-cancer actions.

Matched MeSH terms: Anthraquinones/pharmacology; Anthraquinones/chemistry
Fulltext Chemistry, Biosynthesis, Physicochemical and Biological Properties of Rubiadin: A Promising Natural Anthraquinone for New Drug Discovery and Development

Watroly MN, Sekar M, Fuloria S, Gan SH, Jeyabalan S, Wu YS, et al.

Drug Des Devel Ther, 2021;15:4527-4549.
PMID: 34764636 DOI: 10.2147/DDDT.S338548

Anthraquinones (AQs) are found in a variety of consumer products, including foods, nutritional supplements, drugs, and traditional medicines, and have a wide range of pharmacological actions. Rubiadin, a 1,3-dihydroxy-2-methyl anthraquinone, primarily originates from Rubia cordifolia Linn (Rubiaceae). It was first discovered in 1981 and has been reported for many biological activities. However, no review has been reported so far to create awareness about this molecule and its role in future drug discovery. Therefore, the present review aimed to provide comprehensive evidence of Rubiadin's phytochemistry, biosynthesis, physicochemical properties, biological properties and therapeutic potential. Relevant literature was gathered from numerous scientific databases including PubMed, ScienceDirect, Scopus and Google Scholar between 1981 and up-to-date. The distribution of Rubiadin in numerous medicinal plants, as well as its method of isolation, synthesis, characterisation, physiochemical properties and possible biosynthesis pathways, was extensively covered in this review. Following a rigorous screening and tabulating, a thorough description of Rubiadin's biological properties was gathered, which were based on scientific evidences. Rubiadin fits all five of Lipinski's rule for drug-likeness properties. Then, the in depth physiochemical characteristics of Rubiadin were investigated. The simple technique for Rubiadin's isolation from R. cordifolia and the procedure of synthesis was described. Rubiadin is also biosynthesized via the polyketide and chorismate/o-succinylbenzoic acid pathways. Rubiadin is a powerful molecule with anticancer, antiosteoporotic, hepatoprotective, neuroprotective, anti-inflammatory, antidiabetic, antioxidant, antibacterial, antimalarial, antifungal, and antiviral properties. The mechanism of action for the majority of the pharmacological actions reported, however, is unknown. In addition to this review, an in silico molecular docking study was performed against proteins with PDB IDs: 3AOX, 6OLX, 6OSP, and 6SDC to support the anticancer properties of Rubiadin. The toxicity profile, pharmacokinetics and possible structural modifications were also described. Rubiadin was also proven to have the highest binding affinity to the targeted proteins in an in silico study; thus, we believe it may be a potential anticancer molecule. In order to present Rubiadin as a novel candidate for future therapeutic development, advanced studies on preclinical, clinical trials, bioavailability, permeability and administration of safe doses are necessary.

Matched MeSH terms: Anthraquinones/isolation & purification; Anthraquinones/pharmacology*; Anthraquinones/chemistry
Thiadiazole-, selenadiazole- and triazole-fused anthraquinones as G-quadruplex targeting anticancer compounds

Andreeva DV, Vedekhina TS, Gostev AS, Dezhenkova LG, Volodina YL, Markova AA, et al.

Eur J Med Chem, 2024 Mar 15;268:116222.
PMID: 38387333 DOI: 10.1016/j.ejmech.2024.116222

G-quadruplex (G4) ligands attract considerable attention as potential anticancer therapeutics. In this study we proposed an original scheme for synthesis of azole-fused anthraquinones and prepared a series of G4 ligands carrying amino- or guanidinoalkylamino side chains. The heterocyclic core and structure of the terminal groups strongly affect on binding to G4-forming oligonucleotides, cellular accumulation and antitumor potency of compounds. In particular, thiadiazole- and selenadiazole- but not triazole-based ligands inhibit the proliferation of tumor cells (e.g. K562 leukemia) and stabilize primarily telomeric and c-MYC G4s. Anthraselenadiazole derivative 11a showed a good affinity to c-MYC G4 in vitro and down-regulated expression of c-MYC oncogene in cellular conditions. Further studies revealed that anthraselenadiazole 11a provoked cell cycle arrest and apoptosis in a dose- and time-dependent manner inhibiting K562 cells growth. Taken together, this work gives a valuable example that the closely related heterocycles may cause a significant difference in biological properties of G4 ligands.

Matched MeSH terms: Anthraquinones/chemistry
Fulltext Cytotoxic effect of damnacanthal, nordamnacanthal, zerumbone and betulinic acid isolated from Malaysian plant sources

International Food Research Journal, 2010;17(3):711-719.
MyJurnal

The present study was to evaluate the toxicity of damnacanthal, nordamnacanthal, betulinic acid and zerumbone isolated from local medicinal plants towards leukemia cell lines and immune cells by using MTT assay and flow cytometry cell cycle analysis. The results showed that damnacanthal significantly inhibited HL-60 cells, CEM-SS and WEHI-3B with the IC50 value of 4.0 µg/mL, 8.0 µg/mL and 3.3 µg/mL, respectively. Nordamnacanthal and betulinic acid showed stronger inhibition towards CEM-SS and HL-60 cells with the IC50 value of 5.7 µg/mL and 5.0 µg/mL, respectively. In contrast, Zerumbone was demonstrated to be more toxic towards those leukemia cells with the IC50 value less than 10 µg/mL. Damnacanthal, nordamnacanthal and betulinic acid were not toxic towards 3T3 and PBMC compared to doxorubicin which showed toxicity effects towards 3T3 and PBMC with the IC50 value of 3.0 µg/mL and 28.0 µg/mL, respectively. The cell cycle analysis exhibited that damnacanthal exerted its toxicity effect towards HL-60 cells by inducing apoptosis with value of 25% after 72 hours treatment. Thus, these compounds could be the potential anticancer drug with less toxic side effect.

Matched MeSH terms: Anthraquinones
Fulltext Melanosis coli

Kew, Siang-Tong

International e-Journal of Science, Medicine & Education, 2012;6(10):0-0.
MyJurnal

Melanosis coli denotes brownish discoloration of the colonic mucosa found on endoscopy
or histopathologic examination. The condition has no specific symptom on its own. It is a fairly frequent incidental finding of colonic biopsies and resection specimens. The pigmentation is caused by apoptotic cells which are ingested by macrophages and subsequently transported into the lamina propria, where lysosomes use them to produce lipofuscin pigment, not melanin as the name suggests. Melanosis coli develops in over 70% of persons who use anthraquinone laxatives (eg cascara sagrada, aloe, senna, rhubarb, and frangula), often within 4 months of use. Long-term use is generally believed to be necessary to cause melanosis coli.The condition is widely regarded as benign and reversible, and disappearance of the pigment generally occurs within a year of stopping laxatives. Although
often due to prolonged use of anthraquinone, melanosis can probably result from other factors or exposure to other laxatives. It has been reported as a consequence of longstanding inflammatory bowel disease. Some investigators suggested that increase in apoptosis of
colonic mucosa by anthraquinone laxatives increased the risk of colonic cancer. Recent data, including those from large-scale retrospective, prospective and experimental studies, did not show any increased cancer risk.

Matched MeSH terms: Anthraquinones
Functional properties of chitosan built nanohydrogel with enhanced glucose-sensitivity

Ullah F, Othman MB, Javed F, Ahmad Z, Akil HM, Rasib SZ

Int J Biol Macromol, 2016 Feb;83:376-84.
PMID: 26597568 DOI: 10.1016/j.ijbiomac.2015.11.040

A new approach to design multifunctional chitosan based nanohydrogel with enhanced glucose sensitivity, stability, drug loading and release profile are reported. Two approaches were followed for functionalization of chitosan based nanohydrogel with 3-APBA via EDC and 3-APTES. The effective functionalization, structure and morphology of Chitosan based IPN respectively were confirmed by FTIR, SEM and AFM. At physiological conditions, the glucose-induced volume phase transition and release profile of the model drug Alizarin Red with 1,2-diol structure (comparative to insulin as a drug as well as a dye for bio separation) were studied at various glucose concentrations, pH and ionic strengths. The results suggested a new concept for diabetes treatment and diols sensitivity in view of their potential hi-tech applications in self-regulated on-off response to the treatment (drug delivery and bio separation concurrently).

Matched MeSH terms: Anthraquinones/chemistry
Organically modified montmorillonite composited with magnetic glyoxal-chitosan Schiff base for reactive blue 19 dye removal: Process optimization and adsorptive mechanism

Abdulhameed AS, Hapiz A, Musa SA, Kashi E, Wu R, ALOthman ZA, et al.

Int J Biol Macromol, 2024 Jan;256(Pt 2):128463.
PMID: 38029908 DOI: 10.1016/j.ijbiomac.2023.128463

In this study, a new biocomposite magnetic adsorbent (magnetic glyoxal-chitosan Schiff base/organically modified montmorillonite (MCTS-GOX/OMMT)) was synthesized and employed for the adsorption of reactive blue 19 dye (RB19) from aqueous environment. The physicochemical properties of the MCTS-GOX/OMMT were confirmed by using various characterization techniques such as BET, XRD, FTIR, SEM-EDX, VSM, and pHpzc. The adsorption key variables were statistically optimized via Box-Behnken design (BBD) And accordingly the best operational conditions to achieve maximum RB19 removal were recorded at MCTS-GOX/OMMT dosage = 0.1 g/0.1 L, solution pH = 4, and working temperature = 25 °C. The adsorption process for RB19 appeared to follow the pseudo-second-order kinetic and the Langmuir isotherm models, according to the findings of the adsorption kinetics and equilibrium investigations. The maximum adsorption capacity of the MCTS-GOX/OMMT towards RB19 was 122.3 mg/g, demonstrating its preferable adsorption capability. The successful development of this novel magnetic bioadsorbent with excellent adsorption ability towards organic dyes and efficient separation ability opens possibilities for its practical application in wastewater treatment and dye removal processes.

Matched MeSH terms: Anthraquinones*
Removal of Acid Blue25 from aqueous solutions using Bengal gram fruit shell (BGFS) biomass

Krishna LS, Yuzir A, Yuvaraja G, Ashokkumar V

Int J Phytoremediation, 2017 May 04;19(5):431-438.
PMID: 27739901 DOI: 10.1080/15226514.2016.1244161

The feasibility for the removal of Acid Blue25 (AB25) by Bengal gram fruit shell (BGFS), an agricultural by-product, has been investigated as an alternative for high-cost adsorbents. The impact of various experimental parameters such as dose, different dye concentration, solution pH, and temperature on the removal of Acid Blue25 (AB25) has been studied under the batch mode of operation. pH is a significant impact on the sorption of AB25 onto BGFS. The maximum removal of AB25 was achieved at a pH of 2 (83.84%). The optimum dose of biosorbent was selected as 200 mg for the removal of AB25 onto BGFS. Kinetic studies reveal that equilibrium reached within 180 minutes. Biosorption kinetics has been described by Lagergren equation and biosorption isotherms by classical Langmuir and Freundlich models. Equilibrium data were found to fit well with the Langmuir and Freundlich models, and the maximum monolayer biosorption capacity was 29.41 mg g(-1) of AB25 onto BGFS. The kinetic studies indicated that the pseudo-second-order (PSO) model fitted the experimental data well. In addition, thermodynamic parameters have been calculated. The biosorption process was spontaneous and exothermic in nature with negative values of ΔG° (-1.6031 to -0.1089 kJ mol(-1)) and ΔH° (-16.7920 kJ mol(-1)). The negative ΔG° indicates the feasibility of physical biosorption process. The results indicate that BGFS could be used as an eco-friendly and cost-effective biosorbent for the removal of AB25 from aqueous solution.

Matched MeSH terms: Anthraquinones/metabolism*
Fulltext Dihydrotestosterone, a robust promoter of osteoblastic proliferation and differentiation: understanding of time-mannered and dose-dependent control of bone forming cells

Thu HE, Mohamed IN, Hussain Z, Shuid AN

Iran J Basic Med Sci, 2017 Aug;20(8):894-904.
PMID: 29085581 DOI: 10.22038/IJBMS.2017.9111

OBJECTIVES: The present study was aimed to evaluate the time-mannered and dose-dependent effects of 5α-dihydrotestosterone (5α-DHT) on the proliferation and differentiation of bone forming cells using MC3T3-E1 cells.
MATERIALS AND METHODS: Cell proliferation was analyzed using MTS and phase contrast microscopic assays. Osteogenic differentiation was assessed through a series of in vitro experiments including crystal violet staining, alkaline phosphatase (ALP) activity, and Van Gieson (VG) staining. Taken together, the efficiency of bone mineralization was examined by using alizarin red s (ARS) staining, Von Kossa staining, scanning electron microscopy (SEM) and energy dispersive x-ray (EDX) analysis.
RESULTS: The resulting data revealed that 5α-DHT exhibits promising potential particularly at a dose of 0.1 ng/ml, in promoting the growth of MC3T3-E1 cells compared to the control group (CN). Moreover, a significantly higher ALP activity was evident in the experimental group treated with 5α-DHT compared to the CN group at various time intervals. MC3T3-E1 cells treated with 5α-DHT also expressed a remarkably higher collagen deposition and mineralization (calcium and phosphate contents) compared to the CN group at various time intervals.
CONCLUSION: Conclusively, we suggest that 5α-DHT exhibits outstanding potential of promoting proliferation and differentiation in osteoblasts which could be the in vitro basis for the efficacy of 5α-DHT in the treatment of androgen-deficient male osteoporosis.

Matched MeSH terms: Anthraquinones

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