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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*
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 Anthraquinones with antiplasmodial activity from the roots of Rennellia elliptica Korth. (Rubiaceae)

Osman CP, Ismail NH, Ahmad R, Ahmat N, Awang K, Jaafar FM

Molecules, 2010;15(10):7218-26.
PMID: 20966871 DOI: 10.3390/molecules15107218

Dichloromethane root extract of Rennellia elliptica Korth. showed strong inhibition of Plasmodium falciparum growth in vitro with an IC₅₀ value of 4.04 µg/mL. A phytochemical study of the dichloromethane root extract has led to the isolation and characterization of a new anthraquinone, 1,2-dimethoxy-6-methyl-9,10-anthraquinone (1), and ten known anthraquinones: 1-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone (2), nordamnacanthal (3), 2-formyl-3-hydroxy-9,10-anthraquinone (4), damnacanthal (5), lucidin-ω-methyl ether (6), 3-hydroxy-2-methyl-9,10-anthraquinone (7), rubiadin (8), 3-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone (9), rubiadin-1-methyl ether (10) and 3-hydroxy-2-hydroxymethyl-9,10-anthraquinone (11). Structural elucidation of all compounds was accomplished by modern spectroscopic methods, notably 1D and 2D NMR, IR, UV and HREIMS. The new anthraquinone 1, 2-formyl-3-hydroxy-9,10-anthraquinone (4) and 3-hydroxy-2-methyl-9,10-anthraquinone (7) possess strong antiplasmodial activity, with IC₅₀ values of 1.10, 0.63 and 0.34 µM, respectively.

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/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/chemistry
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
Fulltext Indian jujuba seed powder as an eco-friendly and a low-cost biosorbent for removal of acid blue 25 from aqueous solution

Krishna LS, Reddy AS, Zuhairi WY, Taha MR, Reddy AV

ScientificWorldJournal, 2014;2014:184058.
PMID: 25383360 DOI: 10.1155/2014/184058

Indian jujuba seed powder (IJSP) has been investigated as a low-cost and an eco-friendly biosorbent, prepared for the removal of Acid Blue 25 (AB25) from aqueous solution. The prepared biomaterial was characterized by using FTIR and scanning electron microscopic studies. The effect of operation variables, such as IJSP dosage, contact time, concentration, pH, and temperature on the removal of AB25 was investigated, using batch biosorption technique. Removal efficiency increased with increase of IJSP dosage but decreased with increase of temperature. The equilibrium data were analyzed by the Langmuir and the Freundlich isotherm models. The data fitted well with the Langmuir model with a maximum biosorption capacity of 54.95 mg g(-1). The pseudo-second-order kinetics was the best for the biosorption of AB25 by IJSP, with good correlation. Thermodynamic parameters such as standard free energy change (ΔG(0)), standard enthalpy changes (ΔH(0)), and standard entropy changes (ΔS(0)) were analyzed. The removal of AB25 from aqueous solution by IJSP was a spontaneous and exothermic adsorption process. The results suggest that IJSP is a potential low-cost and an eco-friendly biosorbent for the AB25 removal from synthetic AB25 wastewater.

Matched MeSH terms: Anthraquinones/chemistry*
Fulltext Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions

Nor SM, Sukari MA, Azziz SS, Fah WC, Alimon H, Juhan SF

Molecules, 2013 Jul 08;18(7):8046-62.
PMID: 23884135 DOI: 10.3390/molecules18078046

Aminoanthraquinones were successfully synthesized via two reaction steps. 1,4-Dihydroxyanthraquinone (1) was first subjected to methylation, reduction and acylation to give an excellent yield of anthracene-1,4-dione (3), 1,4-dimethoxyanthracene-9,10-dione (5) and 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate (7). Treatment of 1, 3, 5 and 7 with BuNH2 in the presence of PhI(OAc)2 as catalyst produced seven aminoanthraquinone derivatives 1a, b, 3a, and 5a-d. Amination of 3 and 5 afforded three new aminoanthraquinones, namely 2-(butylamino)anthracene-1,4-dione (3a), 2-(butylamino)anthracene-9,10-dione (5a) and 2,3-(dibutylamino)anthracene-9,10-dione (5b). All newly synthesised aminoanthraquinones were examined for their cytotoxic activity against MCF-7 (estrogen receptor positive human breast) and Hep-G2 (human hepatocellular liver carcinoma) cancer cells using MTT assay. Aminoanthraquinones 3a, 5a and 5b exhibited strong cytotoxicity towards both cancer cell lines (IC50 1.1-13.0 µg/mL).

Matched MeSH terms: Anthraquinones/chemistry
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
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/chemistry*
Microwave-assisted synthesis of Zn/Al layered double hydroxide-(anthraquinone-2,6-disulfonate) nanocomposite

bin Hussein MZ, Zainal Z, Hin TY, Tat OW

J Microw Power Electromagn Energy, 2001;36(2):113-9.
PMID: 15040529

Nanocomposites of Zn/Al-layered double hydroxide(anthraquinone-2,6-disulfonate) were synthesized by spontaneous direct assembly of inorganic and organic phases from aqueous solution. Powder X-ray diffraction patterns showed that a pure, single nanocomposite phase of good crystallinity was obtained using 1.0 M antraquinone-2,6-disulfonate ion (AQ26) and aging at 80 degrees C using conventional heating for 7 days or 0.5 h under microwave radiation, and these samples are denoted as ZAAN26C or ZAAN26MH, respectively. Zn/Al-nitrate-layered double hydroxide synthesized by a conventional method (ZANLC) showed a basal spacing of 8.3 A while both the nanocomposites showed 18.8 A as a result of AQ26 intercalation. FTIR study showed that the resulting nanocomposites are free from nitrate, the co-anion present in the mother liquor, indicating that only AQ26 is preferred during intercalation for the formation of the nanocomposite. The Brunauer, Emmet and Teller (BET) and micropore surface areas for ZAAN26C decreased relative to the ZANLC from 16.2 to 4.7 and 1.6 to 1.3 m2/g, respectively. These results indicate that AQ26 can be rapidly interdcalated in layered double hydroxide using microwave-aging resulting in a nanocomposite.

Matched MeSH terms: Anthraquinones/chemistry*
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/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/chemistry
Enhanced induction of cell cycle arrest and apoptosis via the mitochondrial membrane potential disruption in human U87 malignant glioma cells by aloe emodin

Ismail S, Haris K, Abdul Ghani AR, Abdullah JM, Johan MF, Mohamed Yusoff AA

J Asian Nat Prod Res, 2013 Sep;15(9):1003-12.
PMID: 23869465 DOI: 10.1080/10286020.2013.818982

Aloe emodin, one of the active compounds found in Aloe vera leaves, plays an important role in the regulation of cell growth and death. It has been reported to promote the anti-cancer effects in various cancer cells by inducing apoptosis. However, the mechanism of inducing apoptosis by this agent is poorly understood in glioma cells. This research is to investigate the apoptosis and cell cycle arrest inducing by aloe emodin on U87 human malignant glioma cells. Aloe emodin showed a time- and dose-dependent inhibition of U87 cells proliferation and decreased the percentage of viable U87 cells via the induction of apoptosis. Characteristic morphological changes, such as the formation of apoptotic bodies, were observed with confocal microscope by Annexin V-FITC/PI staining, supporting our viability study and flow cytometry analysis results. Our data also demonstrated that aloe emodin arrested the cell cycle in the S phase and promoted the loss of mitochondrial membrane potential in U87 cells that indicated the early event of the mitochondria-induced apoptotic pathway.

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/chemistry
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/chemistry
Development of biodegradable sustained-release damnacanthal nanocapsules for potential application in in-vitro breast cancer studies

Mohd MR, Ariff TM, Mohamad N, Abdul Latif AZ, Wan Nik WMN, Mohamed A, et al.

Pak J Pharm Sci, 2019 Sep;32(5):2155-2162.
PMID: 31813882

The "noni" species of Morinda citrifolia L., is using in traditional medicine in the tropical country for over 2000 years. Noni fruit has come from the Morinda citrifolia tree which is called Rubiaceae, and it is from the coffee family. It is a perennial herb whose ripe fruit has a robust butyric acid smell and flavor. Recently scientists have proven that this fruit has antioxidant and antibiotic properties in vitro. An anthraquinone, damnacanthal, is one of the constituents of Morinda citrifolia. It has been demonstrated to have anti-cancer properties. Damnacanthal has low water solubility and low bioavailability. Formulating of damnacanthal into the biodegradable nanocapsule drug delivery system may increase its bioavailability. Various formulations of damnacanthal would be developed to enable the selection of a dosage form that could offer the provision of the anti-cancer bioactive substance with suitable sustained- or controlled release properties. The efficiency of extraction of damnacanthal will be compared using both conventional and traditional method. Both the damnacanthal and an anthraquinone active compounds extracted from noni roots, are currently being studied in the context of anti-cancer study. Soon, the medical values, bioactivities and nutritional of this fruit can be assessed, especially its anti-cancer activity, this fruit extract could play an outstanding economic role in Malaysia and other tropical countries.

Matched MeSH terms: 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/chemistry

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