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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*
Growth and anthraquinone production of Morinda elliptica cell suspension cultures in a stirred-tank bioreactor

Abdullah MA, Ariff AB, Marziah M, Ali AM, Lajis NH

J Agric Food Chem, 2000 Sep;48(9):4432-8.
PMID: 10995375

The effects of medium strategy, number of impellers, aeration mode, and mode of operation on Morinda elliptica cell suspension cultures in a stirred-tank bioreactor are described. A lower number of impellers and continuous aeration contributed toward high cell growth rate, whereas a higher number of impellers reduced cell growth rate, although not anthraquinone yield. The semicontinuous mode could indirectly imitate the larger scale version of production medium strategy and improved anthraquinone production even with 0. 012% (v/v) antifoam addition. Production medium promoted both growth (maximum dry cell weight of 24.6 g/L) and anthraquinone formation (maximum content of 19.5 mg/g of dry cell weight), without any necessity for antifoam addition. Cultures in production medium or with higher growth rate and anthraquinone production were less acidic than cultures in growth medium or with lower growth rate and anthraquinone production. Using the best operating variables, growth of M. elliptica cells (24.6 g/L) and anthraquinone yield (0.25 g/L) were 45% and 140%, respectively, lower than those using a shake flask culture after 12 days of cultivation.

Matched MeSH terms: Anthraquinones/metabolism*
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 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 3-Bromo-1-hydroxy-9,10-anthraquinone (BHAQ) inhibits growth and migration of the human breast cancer cell lines MCF-7 and MDA-MB231

Abu N, Akhtar MN, Ho WY, Yeap SK, Alitheen NB

Molecules, 2013 Aug 27;18(9):10367-77.
PMID: 23985955 DOI: 10.3390/molecules180910367

Breast cancer is becoming more prominent in women today. As of now, there are no effective treatments in treating metastatic breast cancer. We have tested the cytotoxic and anti-migration effects of BHAQ, a synthesized anthraquinone, on two breast cancer cell lines, MCF-7 and MDA-MB231. Anthraquinones are an interesting class of molecules that display a wide spectrum of biological applications, including anticancer properties. Cellular inhibition was tested through a MTT assay, double acridine orange/propidium iodide staining and FACS cell cycle analysis. Inhibition of migration was tested by the wound healing method, and migration through a Boyden chamber. BHAQ was cytotoxic towards both cell lines in a dose dependent and possibly cell-dependent manner. Additionally, BHAQ also inhibited the migration of the highly metastatic MDA-MB231 cell line.

Matched MeSH terms: Anthraquinones/chemical synthesis; 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*
Anthraquinones from Hedyotis capitellata

Ahmad R, Shaari K, Lajis NH, Hamzah AS, Ismail NH, Kitajima M

Phytochemistry, 2005 May;66(10):1141-7.
PMID: 15924918

Four new furanoanthraquinones, 2-hydroxymethyl-3,4-[2'-(1-hydroxy-1-methylethyl)-dihydrofurano]-8-hydroxyanthraquinone, 2-hydroxymethyl-3,4-[1'-hydroxy-2'-(1-hydroxy-1-methylethyl)-dihydrofurano]-8-hydroxyanthraquinone, 2-hydroxymethyl-3,4-[2'-1-hydroxy-1-methylethyl)-dihydrofurano]anthraquinone and 2-methyl-3,4-[2'-(1-hydroxy-1-methylethyl)-dihydrofurano] anthraquinone or capitellataquinone A-D and four known anthraquinones, rubiadin, anthragallol 2-methyl ether, alizarin 1-methyl ether and digiferruginol, together with scopoletin were isolated from the stems of Hedyotis capitellata Wall (Rubiaceae). Lucidin-3-O-beta-glucoside was isolated from the roots of the plant. Characterization of the new compounds was carried out by extensive NMR studies using FGCOSY, FGHMQC, FGHMBC and DEPT-135 in addition to other spectroscopic methods.

Matched MeSH terms: Anthraquinones/chemistry*
Fulltext Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues

Akhtar MN, Zareen S, Yeap SK, Ho WY, Lo KM, Hasan A, et al.

Molecules, 2013 Aug 20;18(8):10042-55.
PMID: 23966087 DOI: 10.3390/molecules180810042

Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC50 = 5.70 ± 0.21 and 8.50 ± 1.18 mg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.

Matched MeSH terms: Anthraquinones/pharmacology; Anthraquinones/chemistry*
Immunomodulatory effects of damnacanthal isolated from roots of Morinda elliptica

Alitheen NB, Manaf AA, Yeap SK, Shuhaimi M, Nordin L, Mashitoh AR

Pharm Biol, 2010 Apr;48(4):446-52.
PMID: 20645725 DOI: 10.3109/13880200903168031

Morinda elliptica Ridley (Rubiaceae) has been used traditionally as a medicine to treat various diseases in Malaysia and southeast Asia. In the present study we investigated the immunomodulatory effects of damnacanthal isolated from the roots of Morinda elliptica. The immunomodulatory effect of this compound was evaluated by using the lymphocyte proliferation assay with mouse thymocytes and human peripheral blood mononuclear cells (PBMC). In addition, the effect of the compound on PBMC cell cycle progression was studied by using flow cytometry. The production of human interleukin-2 and human inteleukin-12 cytokines was also assessed using the enzyme linked immunosorbent assay (ELISA) technique. The lymphocyte proliferation assay showed that damnacanthal was able to activate mouse thymocytes and PBMC at a low concentration (0.468 microg/mL). Moreover, the production of human interleukin-2 and human interleukin-12 cytokines in the culture supernatant from damnacanthal activated lymphocytes was markedly up-regulated at 24 h and sustained until 72 h with a slight decrease with time. A positive correlation was found between the level of these two cytokines and the MTT-based proliferation assay. Based on the above results, damnacanthal can act as an immunomodulatory agent which may be very useful for maintaining a healthy immune system.

Matched MeSH terms: Anthraquinones/isolation & purification; Anthraquinones/pharmacology*
Fulltext Aloe emodin enhances tamoxifen cytotoxicity effect on ER a-positive breast cancer cells, MCF-7, through downregulation of MEK1 and MEK2

Amin, I.M., Sheikh Abdul Kadir, S.H., Isa, M.R., Rosdy. N.M.M.N.M., Hasani NAH

JUMMEC, 2016;19(1):1-10.
MyJurnal

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.

Matched MeSH terms: Anthraquinones
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 Combinatorial Cytotoxic Effects of Damnacanthal and Doxorubicin against Human Breast Cancer MCF-7 Cells in Vitro

Aziz MY, Abu N, Yeap SK, Ho WY, Omar AR, Ismail NH, et al.

Molecules, 2016 Sep 14;21(9).
PMID: 27649120 DOI: 10.3390/molecules21091228

Despite progressive research being done on drug therapy to treat breast cancer, the number of patients succumbing to the disease is still a major issue. Combinatorial treatment using different drugs and herbs to treat cancer patients is of major interest in scientists nowadays. Doxorubicin is one of the most used drugs to treat breast cancer patients. The combination of doxorubicin to other drugs such as tamoxifen has been reported. Nevertheless, the combination of doxorubicin with a natural product-derived agent has not been studied yet. Morinda citrifolia has always been sought out for its remarkable remedies. Damnacanthal, an anthraquinone that can be extracted from the roots of Morinda citrifolia is a promising compound that possesses a variety of biological properties. This study aimed to study the therapeutic effects of damnacanthal in combination with doxorubicin in breast cancer cells. Collectively, the combination of both these molecules enhanced the efficacy of induced cell death in MCF-7 as evidenced by the MTT assay, cell cycle, annexin V and expression of apoptosis-related genes and proteins. The effectiveness of doxorubicin as an anti-cancer drug was increased upon addition of damnacanthal. These results could provide a promising approach to treat breast cancer patients.

Matched MeSH terms: Anthraquinones/pharmacokinetics; Anthraquinones/chemistry
Damnacanthal is a potent inducer of apoptosis with anticancer activity by stimulating p53 and p21 genes in MCF-7 breast cancer cells

Aziz MY, Omar AR, Subramani T, Yeap SK, Ho WY, Ismail NH, et al.

Oncol Lett, 2014 May;7(5):1479-1484.
PMID: 24765160

Damnacanthal, an anthraquinone compound, is isolated from the roots of Morinda citrifolia L. (noni), which has been used for traditional therapy in several chronic diseases, including cancer. Although noni has long been consumed in Asian and Polynesian countries, the molecular mechanisms by which it exerts several benefits are starting to emerge. In the present study, the effect of damnacanthal on MCF-7 cell growth regulation was investigated. Treatment of MCF-7 cells with damnacanthal for 72 h indicated an antiproliferative activity. The MTT method confirmed that damnacanthal inhibited the growth of MCF-7 cells at the concentration of 8.2 μg/ml for 72 h. In addition, the drug was found to induce cell cycle arrest at the G1 checkpoint in MCF-7 cells by cell cycle analysis. Damnacanthal induced apoptosis, determined by Annexin V-fluorescein isothiocyanate/propidium iodide (PI) dual-labeling, acridine-orange/PI dyeing and caspase-7 expression. Furthermore, damnacanthal-mediated apoptosis involves the sustained activation of p21, leading to the transcription of p53 and the Bax gene. Overall, the present study provided significant evidence demonstrating that p53-mediated damnacanthal induced apoptosis through the activation of p21 and caspase-7.

Matched MeSH terms: Anthraquinones
Chitosan and chemically modified chitosan beads for acid dyes sorption

Azlan K, Wan Saime WN, Lai Ken L

J Environ Sci (China), 2009;21(3):296-302.
PMID: 19634439

The capabilities of chitosan and chitosan-EGDE (ethylene glycol diglycidyl ether) beads for removing Acid Red 37 (AR 37) and Acid Blue 25 (AB 25) from aqueous solution were examined. Chitosan beads were cross-linked with EGDE to enhance its chemical resistance and mechanical strength. Experiments were performed as a function of pH, agitation period and concentration of AR 37 and AB 25. It was shown that the adsorption capacities of chitosan for both acid dyes were comparatively higher than those of chitosan-EGDE. This is mainly because cross-linking using EGDE reduces the major adsorption sites -NH3+ on chitosan. Langmuir isotherm model showed the best conformity compared to Freundlich and BET. The kinetic experimental data agreed very well to the pseudo second-order kinetic model. The desorption study revealed that after three cycles of adsorption and desorption by NaOH and HCl, both adsorbents retained their promising adsorption abilities. FT-IR analysis proved that the adsorption of acid dyes onto chitosan-based adsorbents was a physical adsorption. Results also showed that chitosan and chitosan-EGDE beads were favourable adsorbers and could be employed as low-cost alternatives for the removal of acid dyes in wastewater treatment.

Matched MeSH terms: Anthraquinones/chemistry
Diacerein-mediated inhibition of IL-6/IL-6R signaling induces apoptotic effects on breast cancer

Bharti R, Dey G, Ojha PK, Rajput S, Jaganathan SK, Sen R, et al.

Oncogene, 2016 Jul 28;35(30):3965-75.
PMID: 26616855 DOI: 10.1038/onc.2015.466

Interleukin-6 (IL-6) signaling network has been implicated in oncogenic transformations making it attractive target for the discovery of novel cancer therapeutics. In this study, potent antiproliferative and apoptotic effect of diacerein were observed against breast cancer. In vitro apoptosis was induced by this drug in breast cancer cells as verified by increased sub-G1 population, LIVE/DEAD assay, cell cytotoxicity and presence of terminal deoxynucleotidyl transferase dUTP nick end labeling (TUNEL)-positive cells, as well as downregulation of antiapoptotic proteins Bcl-2 and Bcl-xL and upregulation of apoptotic protein Bax. In addition, apoptosis induction was found to be caspase dependent. Further molecular investigations indicated that diacerein instigated apoptosis was associated with inhibition of IL-6/IL-6R autocrine signaling axis. Suppression of STAT3, MAPK and Akt pathways were also observed as a consequence of diacerein-mediated upstream inhibition of IL-6/IL-6R. Fluorescence study and western blot analysis revealed cytosolic accumulation of STAT3 in diacerein-treated cells. The docking study showed diacerein/IL-6R interaction that was further validated by competitive binding assay and isothermal titration calorimetry. Most interestingly, it was found that diacerein considerably suppressed tumor growth in MDA-MB-231 xenograft model. The in vivo antitumor effect was correlated with decreased proliferation (Ki-67), increased apoptosis (TUNEL) and inhibition of IL-6/IL-6R-mediated STAT3, MAPK and Akt pathway in tumor remnants. Taken together, diacerein offered a novel blueprint for cancer therapy by hampering IL-6/IL-6R/STAT3/MAPK/Akt network.

Matched MeSH terms: Anthraquinones/pharmacology*
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
Anthraquinones production, hydrogen peroxide level and antioxidant vitamins in Morinda elliptica cell suspension cultures from intermediary and production medium strategies

Chong TM, Abdullah MA, Fadzillah NM, Lai OM, Lajis NH

Plant Cell Rep, 2004 Jul;22(12):951-8.
PMID: 15067428

The effects of medium strategies [maintenance (M), intermediary (G), and production (P) medium] on cell growth, anthraquinone (AQ) production, hydrogen peroxide (H2O2) level, lipid peroxidation, and antioxidant vitamins in Morinda elliptica cell suspension cultures were investigated. These were compared with third-stage leaf and 1-month-old callus culture. With P medium strategy, cell growth at 49 g l(-1), intracellular AQ content at 42 mg g(-1) DW, and H2O2 level at 9 micromol g(-1) FW medium were the highest as compared to the others. However, the extent of lipid peroxidation at 40.4 nmol g(-1) FW and total carotenoids at 13.3 mg g(-1) FW for cultures in P medium were comparable to that in the leaf, which had registered sevenfold lower AQ and 2.2-fold lower H2O2 levels. Vitamin C content at 30-120 microg g(-1) FW in all culture systems was almost half the leaf content. On the other hand, vitamin E content was around 400-500 microg g(-1) FW in 7-day-old cultures from all medium strategies and reduced to 50-150 microg g(-1) FW on day 14 and 21; as compared to 60 microg g(-1) FW in callus and 200 microg g(-1) FW in the leaf. This study suggests that medium strategies and cell growth phase in cell culture could influence the competition between primary and secondary metabolism, oxidative stresses and antioxidative measures. When compared with the leaf metabolism, these activities are dynamic depending on the types and availability of antioxidants.

Matched MeSH terms: Anthraquinones/metabolism*
Fulltext Insights into the computer-aided drug design and discovery based on anthraquinone scaffold for cancer treatment: A protocol for systematic review

Chua HM, Moshawih S, Goh HP, Ming LC, Kifli N

PLoS One, 2023;18(9):e0290948.
PMID: 37656730 DOI: 10.1371/journal.pone.0290948

There is still unmet medical need in cancer treatment mainly due to drug resistance and adverse drug events. Therefore, the search for better drugs is essential. Computer-aided drug design (CADD) and discovery tools are useful to streamline the lengthy and costly drug development process. Anthraquinones are a group of naturally occurring compounds with unique scaffold that exert various biological properties including anticancer activities. This protocol describes a systematic review that provide insights into the computer-aided drug design and discovery based on anthraquinone scaffold for cancer treatment. It was prepared in accordance with the "Preferred reporting items for systematic review and meta-analysis protocols (PRISMA-P) 2015 guidelines, and published in the "International prospective register of systematic reviews" database (PROSPERO: CRD42023432904). Search strategies will be developed based on the combination of relevant keywords and executed in PubMed, Scopus, Web of Science and MedRxiv. Only original studies that employed CADD as primary tool in virtual screening for the purpose of designing or discovering anti-cancer drugs involving anthraquinone scaffold published in English language will be included. Two independent reviewers will be involved to screen and select the papers, extract the data and assess the risk of bias. Apart from exploring the trends and types of CADD methods used, the target proteins of these compounds in cancer treatment will also be revealed in this review. It is believed that the outcome of this study could be utilized to support the ongoing research in similar area with better quality and greater probability of success, consequently optimizing the resources in subsequent in vitro, in vivo, non-clinical and clinical development. It will also serve as an evidence based scientific guide for new research to design novel anthraquinone-derived drug with improved efficacy and safety profile for cancer treatment.

Matched MeSH terms: Anthraquinones/pharmacology
A new anthraquinone from Morinda citrifolia roots

Ee GC, Wen YP, Sukari MA, Go R, Lee HL

Nat Prod Res, 2009;23(14):1322-9.
PMID: 19735047 DOI: 10.1080/14786410902753138

An investigation of Morinda citrifolia roots afforded a new anthraquinone, 2-ethoxy-1-hydroxyanthraquinone (1), along with five other known anthraquinones: 1-hydroxy-2-methylanthraquinone (2), damnacanthal (3), nordamnacanthal (4), 2-formyl-1-hydroxyanthraquinone (5) and morindone-6-methyl-ether (6). This is the first report on the isolation of morindone-6-methyl-ether (6) from this plant. The structures of these compounds were elucidated based on spectroscopic analyses such as NMR, MS and IR. Biological evaluation of five pure compounds and all the extracts against the larvae of Aedes aegypti indicated 1-hydroxy-2-methylanthraquinone (2) and damnacanthal (3) were the extracts to exhibit promising larvicidal activities.

Matched MeSH terms: Anthraquinones/pharmacology; Anthraquinones/chemistry*
Fulltext Anthraquinones from Cratoxylum Aborescens (Guttiferae)

Ee, G.C.L., Jong, V.Y.M., Sukari, M.A., Lee, T.K., Tan, A.

Pertanika Journal of Science & Technology, 2010;18(1):-.
MyJurnal

Our continuing interest in anthraquinones from the Guttiferae family has led us to look at the genus Cratoxylum. A detailed chemical study on Cratoxylum aborescens resulted in the isolation of three anthraquinones, namely 1,8-dihydroxy-3-methoxy-6-methylanthraquinone (1), vismiaquinone (2) and vismione (3). These compounds were identified using 1D and 2D NMR spectroscopy. This is the first report on the chemistry of Cratoxylum aborescens.

Matched MeSH terms: Anthraquinones

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