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Antitumoral Properties of Natural Products Ⅱ

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 December 2021) | Viewed by 47698

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Dr. Roberto Fabiani

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Department of Chemistry, Biology and Biotechnology, University of Perugia, Via del Giochetto, 06126 Perugia, Italy
Interests: cancer chemoprevention; nutrition; olive oil; polyphenols; natural bioactive compounds; antioxidants; oxidative stress; genotoxicity; mutagenicity; apoptosis; cell cycle regulation
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Dear Colleagues,

Cancer is a major public health concern, being one of the main causes of morbidity and mortality worldwide. Carcinogenesis is a complex multistage process in which normal cells, through an alteration of DNA structure/function, are transformed into malignant cells acquiring several properties, such as abnormal proliferation and reduced apoptosis. Studies have demonstrated both in vitro and in vivo that many bioactive compounds, from different natural sources, are able to influence a number of pathways related to tumor development. Many different cancer-specific molecular mechanisms and targets have been identified, making it possible to use such compounds as alternative therapeutic or adjuvant treatments, or as chemopreventive agents. In 2019, we launched the first issue of “Antitumoral Properties of Natural Products”, which published a total of 42 manuscripts, all of them high-quality pubilications, marking the issue as a great success.

It is for this reason that we have now decided to launch a second edition, to which I cordially invite you to contribute and share your recent research results.

Prof. Dr. Roberto Fabiani
Guest Editor

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Keywords

Cancer
Chemoprevention
Bioactive compounds
Natural products
DNA damage
Apoptosis
Proliferation

Published Papers (13 papers)

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Research

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20 pages, 3382 KiB

Open AccessArticle

Analysis of Plant–Plant Interactions Reveals the Presence of Potent Antileukemic Compounds

by David E. Mery, Amanda J. Compadre, Paola E. Ordóñez, Edward J. Selvik, Vladimir Morocho, Jorge Contreras, Omar Malagón, Darin E. Jones, Philip J. Breen, Michael J. Balick, Flavio G. Gaudio, Monica L. Guzman and Cesar M. Compadre

Molecules 2022, 27(9), 2928; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27092928 - 04 May 2022

Cited by 1 | Viewed by 1878

Abstract

A method to identify anticancer compounds in plants was proposed based on the hypothesis that these compounds are primarily present in plants to provide them with an ecological advantage over neighboring plants and other competitors. According to this view, identifying plants that contain compounds that inhibit or interfere with the development of other plant species may facilitate the discovery of novel anticancer agents. The method was developed and tested using Magnolia grandiflora, Gynoxys verrucosa, Picradeniopsis oppositifolia, and Hedyosmum racemosum, which are plant species known to possess compounds with cytotoxic activities. Plant extracts were screened for growth inhibitory activity, and then a thin-layer chromatography bioautography assay was conducted. This located the major antileukemic compounds 1, 2, 4, and 5 in the extracts. Once the active compounds were located, they were extracted and purified, and their structures were determined. The growth inhibitory activity of the purified compounds showed a significant correlation with their antileukemic activity. The proposed approach is rapid, inexpensive, and can easily be implemented in areas of the world with high biodiversity but with less access to advanced facilities and biological assays. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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16 pages, 3186 KiB

Open AccessArticle

Effects of 2′,4′-Dihydroxy-6′-methoxy-3′,5′-dimethylchalcone from Syzygium nervosum Seeds on Antiproliferative, DNA Damage, Cell Cycle Arrest, and Apoptosis in Human Cervical Cancer Cell Lines

by Kraikrit Utama, Nopawit Khamto, Puttinan Meepowpan, Paitoon Aobchey, Jiraporn Kantapan, Korawan Sringarm, Sittiruk Roytrakul and Padchanee Sangthong

Molecules 2022, 27(4), 1154; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27041154 - 09 Feb 2022

Cited by 9 | Viewed by 2768

Abstract

2′,4′-Dihydroxy-6′-methoxy-3′,5′-dimethylchalcone (DMC), a natural product derived from Syzygium nervosum A. Cunn. ex DC., was investigated for its inhibitory activities against various cancer cell lines. In this work, we investigated the effects of DMC and available anticervical cancer drugs (5-fluorouracil, cisplatin, and doxorubicin) on three human cervical cancer cell lines (C-33A, HeLa, and SiHa). DMC displayed antiproliferative cervical cancer activity in C-33A, HeLa, and SiHa cells, with IC₅₀ values of 15.76 ± 1.49, 10.05 ± 0.22, and 18.31 ± 3.10 µM, respectively. DMC presented higher antiproliferative cancer activity in HeLa cells; therefore, we further investigated DMC-induced apoptosis in this cell line, including DNA damage, cell cycle arrest, and apoptosis assays. As a potential anticancer agent, DMC treatment increased DNA damage in cancer cells, observed through fluorescence inverted microscopy and a comet assay. The cell cycle assay showed an increased number of cells in the G₀/G₁ phase following DMC treatment. Furthermore, DMC treatment-induced apoptosis cell death was approximately three- to four-fold higher compared to the untreated group. Here, DMC represented a compound-induced apoptosis for cell death in the HeLa cervical cancer cell line. Our findings suggest that DMC, a phytochemical agent, is a potential candidate for antiproliferative cervical cancer drug development. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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11 pages, 5563 KiB

Open AccessArticle

The Fruits of Paris polyphylla Inhibit Colorectal Cancer Cell Migration Induced by Fusobacterium nucleatum-Derived Extracellular Vesicles

by Liang-Tzung Lin, Yeu-Ching Shi, Chen-Yen Choong and Chen-Jei Tai

Molecules 2021, 26(13), 4081; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26134081 - 04 Jul 2021

Cited by 22 | Viewed by 3393

Abstract

Colorectal cancer (CRC) is one of the most common cancers worldwide. Gut microbiota are highly associated with CRC, and Fusobacterium nucleatum was found to be enriched in CRC lesions and correlated with CRC carcinogenesis and metastases. Paris polyphylla is a well-known herbal medicine that showed anticancer activity. The present study demonstrates that P. polyphylla inhibited the growth of CRC cells. In addition, treating with active compounds pennogenin 3-O-beta-chacotrioside and polyphyllin VI isolated from P. polyphylla inhibited the growth of F. nucleatum. We also found that extracellular vesicles (EVs) released from F. nucleatum could promote mitochondrial fusion and cell invasion in CRC cells, whereas active components from P. polyphylla could dampen such an impact. The data suggest that P. polyphylla and its active ingredients could be further explored as potential candidates for developing complementary chemotherapy for the treatment of CRC. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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13 pages, 2907 KiB

Open AccessFeature PaperArticle

Tetracyclic Thioxanthene Derivatives: Studies on Fluorescence and Antitumor Activity

by Fernando Durães, Patrícia M. A. Silva, Pedro Novais, Isabel Amorim, Luís Gales, Cátia I. C. Esteves, Samuel Guieu, Hassan Bousbaa, Madalena Pinto and Emília Sousa

Molecules 2021, 26(11), 3315; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26113315 - 31 May 2021

Cited by 2 | Viewed by 2932

Abstract

Thioxanthones are bioisosteres of the naturally occurring xanthones. They have been described for multiple activities, including antitumor. As such, the synthesis of a library of thioxanthones was pursued, but unexpectedly, four tetracyclic thioxanthenes with a quinazoline–chromene scaffold were obtained. These compounds were studied for their human tumor cell growth inhibition activity, in the cell lines A375-C5, MCF-7 and NCI-H460. Photophysical studies were also performed. Two of the compounds displayed GI₅₀ values below 10 µM for the three tested cell lines, and structure–activity relationship studies were established. Three compounds presented similar wavelengths of absorption and emission, characteristic of dyes with a push-pull character. The structures of two compounds were elucidated by X-ray crystallography. Two tetracyclic thioxanthenes emerged as hit compounds. One of the two compounds accumulated intracellularly as a bright fluorescent dye in the green channel, as analyzed by both fluorescence microscopy and flow cytometry, making it a promising theranostic cancer drug candidate. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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15 pages, 21154 KiB

Open AccessArticle

Anti-Ageing Potential of S. euboea Heldr. Phenolics

by Ekaterina-Michaela Tomou, Christina D. Papaemmanouil, Dimitrios A. Diamantis, Androniki D. Kostagianni, Paschalina Chatzopoulou, Thomas Mavromoustakos, Andreas G. Tzakos and Helen Skaltsa

Molecules 2021, 26(11), 3151; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26113151 - 25 May 2021

Cited by 9 | Viewed by 2886

Abstract

In recent years, the use of Sideritis species as bioactive agents is increasing exponentially. The present study aimed to investigate the chemical constituents, as well as the anti-ageing potential of the cultivated Sideritis euboea Heldr. The chemical fingerprinting of the ethyl acetate residue of this plant was studied using 1D and 2D-NMR spectra. Isomeric compounds belonging to acylated flavone derivatives and phenylethanoid glycosides were detected in the early stage of the experimental process through 2D-NMR techniques. Overall, thirty-three known compounds were isolated and identified. Some of them are reported for the first time not only in S. euboea, but also in genus Sideritis L. The anti-ageing effect of the ethyl acetate residue and the isolated specialized products was assessed as anti-hyaluronidase activity. In silico docking simulation revealed the interactions of the isolated compounds with hyaluronidase. Furthermore, the in vitro study on the inhibition of hyaluronidase unveiled the potent inhibitory properties of ethyl acetate residue and apigenin 7-O-β-d-glucopyranoside. Though, the isomers of apigenin 7-O-p-coumaroyl-glucosides and also the 4′-methyl-hypolaetin 7-O-[6′′′-O-acetyl-β-d-allopyranosyl]-(1→2)-β-d-glucopyranoside exerted moderate hyaluronidase inhibition. This research represents the first study to report on the anti-hyaluronidase activity of Sideritis species, confirming its anti-inflammatory, cytotoxic and anti-ageing effects and its importance as an agent for cosmetic formulations as also anticancer potential. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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12 pages, 3122 KiB

Open AccessArticle

Protective Role of Vanillic Acid against Diethylnitrosamine- and 1,2-Dimethylhydrazine-Induced Hepatocarcinogenesis in Rats

by Charatda Punvittayagul, Arpamas Chariyakornkul, Kanokwan Jarukamjorn and Rawiwan Wongpoomchai

Molecules 2021, 26(9), 2718; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092718 - 05 May 2021

Cited by 25 | Viewed by 2443

Abstract

This study aimed to evaluate the cancer chemopreventive activity of vanillic acid (VA) in diethylnitrosamine- and 1,2-dimethylhydrazine-induced liver and colon carcinogenesis in rats. VA did not induce the formation of hepatic glutathione S-transferase placental form (GST-P) positive foci and colonic aberrant crypt foci, demonstrating no carcinogenic activity. VA (75 mg kg⁻¹ body weight) could significantly reduce the number and areas of hepatic GST-P positive foci when administered before carcinogen injections, but no such effect was seen when it was administered after carcinogen injection. No protection was seen in the colon when VA was treated before or after carcinogen injection. Immunohistochemical studies demonstrated the decreased expression of proliferating cell nuclear antigen and the induction of apoptosis. Mechanistic studies showed that VA significantly induced the expression of GSTA-5 and Nrf-2 genes, which are associated with the detoxification system. Likewise, the antiproliferative effect was noticed by the reduction of Cyclin D1 expression. The apoptotic activity may be due to the upregulation of Caspase-3 and Bad levels and downregulation of the Bcl-2 level. These data suggest that VA exhibited significant protection against diethylnitrosamine- and 1,2-dimethylhydrazine-induced hepatocarcinogenesis, which might be related to the induction of the detoxifying enzyme, the reduction of proliferation and the induction of apoptosis. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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13 pages, 2027 KiB

Open AccessFeature PaperArticle

Crosstalk of Cancer Signaling Pathways by Cyclic Hexapeptides and Anthraquinones from Rubia cordifolia

by Premalatha Balachandran, Mohamed Ali Ibrahim, Jin Zhang, Mei Wang, David S. Pasco and Ilias Muhammad

Molecules 2021, 26(3), 735; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26030735 - 31 Jan 2021

Cited by 8 | Viewed by 3314

Abstract

The anticancer activities of Rubia cordifolia and its constituents have been reported earlier, but their influence on the crosstalk of complex cancer-related signaling metabolic pathways (i.e., transcription factors; TF) has not yet been fully investigated. In this study, R. cordifolia root extract was subjected to the cancer signaling assay based bioactivity-guided fractionation, which yielded the following compounds viz., three anthraquinones, namely alizarin (1), purpurin (2), and emodin (3); two lignans, namely eudesmin (4) and compound 5; and two cyclic hexapeptides, namely deoxybouvardin RA-V (6), and a mixture of 6+9 (RA-XXI). The structures of the isolated compounds were determined by NMR spectroscopy and HRESIMS. The isolated compounds 1, 2, 3, 6, and a mixture of 6+9 were tested against a panel of luciferase reporter genes that assesses the activity of a wide-range of cancer-related signaling pathways. In addition, reference anthraquinones viz., chrysophanol (11), danthron (12), quinizarin (13), aloe-emodin (14), and α-lapachone (15) were also tested. Among the tested compounds, the cyclic hexapeptide 6 was found to be very active against several signaling pathways, notably Wnt, Myc, and Notch with IC₅₀ values of 50, 75, and 93 ng/mL, respectively. Whereas, the anthraquinones exhibited very mild or no inhibition against these signaling pathways. Compound 6 being the most active, we tested it for stability in simulated intestinal (SIF) and gastric fluids (SGF), since the stability in biological fluid is a key short-coming of cyclic hexapeptides. The anticancer activity of 6 was found to remain unchanged before and after the treatment of simulated gastric/intestinal fluids, indicating that RA-V was stable. As a result, it could be bioavailable when orally used in therapeutics and possibly a drug candidate for cancer treatment. The mechanism for the preferential inhibition of these pathways and the possible crosstalk effect with other previously reported signaling pathways has been discussed. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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16 pages, 4011 KiB

Open AccessArticle

Bombyx batryticatus Protein-Rich Extract Induces Maturation of Dendritic Cells and Th1 Polarization: A Potential Immunological Adjuvant for Cancer Vaccine

by Ha-Yeon Song, Jeong Moo Han, Eui-Hong Byun, Woo Sik Kim, Ho Seong Seo and Eui-Baek Byun

Molecules 2021, 26(2), 476; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26020476 - 18 Jan 2021

Cited by 11 | Viewed by 2864

Abstract

Bombyx batryticatus, a protein-rich edible insect, is widely used as a traditional medicine in China. Several pharmacological studies have reported the anticancer activity of B. batryticatus extracts; however, the capacity of B. batryticatus extracts as immune potentiators for increasing the efficacy of cancer immunotherapy is still unverified. In the present study, we investigated the immunomodulatory role of B. batryticatus protein-rich extract (BBPE) in bone marrow-derived dendritic cells (BMDCs) and DC vaccine-immunized mice. BBPE-treated BMDCs displayed characteristics of mature immune status, including high expression of surface molecules (CD80, CD86, major histocompatibility complex (MHC)-I, and MHC-II), increased production of proinflammatory cytokines (tumor necrosis factor-α and interleukin-12p70), enhanced antigen-presenting ability, and reduced endocytosis. BBPE-treated BMDCs promoted naive CD4⁺ and CD8⁺ T-cell proliferation and activation. Furthermore, BBPE/ovalbumin (OVA)-pulsed DC-immunized mice showed a stronger OVA-specific multifunctional T-cell response in CD4⁺ and CD8⁺ T cells and a stronger Th1 antibody response than mice receiving differently treated DCs, which showed the enhanced protective effect against tumor growth in E.G7 tumor-bearing mice. Our data demonstrate that BBPE can be a novel immune potentiator for a DC-based vaccine in anticancer therapy. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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20 pages, 2153 KiB

Open AccessReview

Anti-Cancer Properties of Stevia rebaudiana; More than a Sweetener

by Nikos Iatridis, Anastasia Kougioumtzi, Katerina Vlataki, Styliani Papadaki and Angeliki Magklara

Molecules 2022, 27(4), 1362; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27041362 - 17 Feb 2022

Cited by 29 | Viewed by 6736

Abstract

Stevia rebaudiana Bertoni is a perennial shrub from Paraguay that is nowadays widely cultivated, since it is increasingly being utilized as a sugar substitute in various foodstuffs due to its sweetness and minimal caloric content. These properties of the plant’s derivatives have spurred research on their biological activities revealing a multitude of benefits to human health, including antidiabetic, anticariogenic, antioxidant, hypotensive, antihypertensive, antimicrobial, anti-inflammatory and antitumor actions. To our knowledge, no recent reviews have surveyed and reported published work solely on the latter. Consequently, our main objective was to present a concise, literature-based review of the biological actions of stevia derivatives in various tumor types, as studied in in vitro and in vivo models of the disease. With global cancer estimates suggesting a 47% increase in cancer cases by 2040 compared to 2020, the data reviewed in this article should provide a better insight into Stevia rebaudiana and its products as a means of cancer prevention and therapy within the context of a healthy diet. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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18 pages, 747 KiB

Open AccessReview

Natural Compounds as Metabolic Modulators of the Tumor Microenvironment

by Ana S. Dias, Luisa Helguero, Catarina R. Almeida and Iola F. Duarte

Molecules 2021, 26(12), 3494; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26123494 - 08 Jun 2021

Cited by 15 | Viewed by 2930

Abstract

The tumor microenvironment (TME) is a heterogenous assemblage of malignant and non-malignant cells, including infiltrating immune cells and other stromal cells, together with extracellular matrix and a variety of soluble factors. This complex and dynamic milieu strongly affects tumor differentiation, progression, immune evasion, and response to therapy, thus being an important therapeutic target. The phenotypic and functional features of the various cell types present in the TME are largely dependent on their ability to adopt different metabolic programs. Hence, modulating the metabolism of the cells in the TME, and their metabolic crosstalk, has emerged as a promising strategy in the context of anticancer therapies. Natural compounds offer an attractive tool in this respect as their multiple biological activities can potentially be harnessed to ‘(re)-educate’ TME cells towards antitumoral roles. The present review discusses how natural compounds shape the metabolism of stromal cells in the TME and how this may impact tumor development and progression. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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29 pages, 3300 KiB

Open AccessReview

Polyphenols of the Mediterranean Diet and Their Metabolites in the Prevention of Colorectal Cancer

by Aline Yammine, Amira Namsi, Dominique Vervandier-Fasseur, John J. Mackrill, Gérard Lizard and Norbert Latruffe

Molecules 2021, 26(12), 3483; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26123483 - 08 Jun 2021

Cited by 28 | Viewed by 5261

Abstract

The Mediterranean diet is a central element of a healthy lifestyle, where polyphenols play a key role due to their anti-oxidant properties, and for some of them, as nutripharmacological compounds capable of preventing a number of diseases, including cancer. Due to the high prevalence of intestinal cancer (ranking second in causing morbidity and mortality), this review is focused on the beneficial effects of selected dietary phytophenols, largely present in Mediterranean cooking: apigenin, curcumin, epigallocatechin gallate, quercetin-rutine, and resveratrol. The role of the Mediterranean diet in the prevention of colorectal cancer and future perspectives are discussed in terms of food polyphenol content, the effectiveness, the plasma level, and the importance of other factors, such as the polyphenol metabolites and the influence of the microbiome. Perspectives are discussed in terms of microbiome-dependency of the brain-second brain axis. The emergence of polyphenol formulations may strengthen the efficiency of the Mediterranean diet in the prevention of cancer. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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30 pages, 1274 KiB

Open AccessReview

Sweet Cherries as Anti-Cancer Agents: From Bioactive Compounds to Function

by Lara R. S. Fonseca, Gonçalo R. Silva, Ângelo Luís, Henrique J. Cardoso, Sara Correia, Cátia V. Vaz, Ana P. Duarte and Sílvia Socorro

Molecules 2021, 26(10), 2941; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26102941 - 15 May 2021

Cited by 14 | Viewed by 3529

Abstract

Sweet cherries (Prunus avium L.) are among the most appreciated fruits worldwide because of their organoleptic properties and nutritional value. The accurate phytochemical composition and nutritional value of sweet cherries depends on the climatic region, cultivar, and bioaccessibility and bioavailability of specific compounds. Nevertheless, sweet cherry extracts are highly enriched in several phenolic compounds with relevant bioactivity. Over the years, technological advances in chemical analysis and fields as varied as proteomics, genomics and bioinformatics, have allowed the detailed characterization of the sweet cherry bioactive phytonutrients and their biological function. In this context, the effect of sweet cherries on suppressing important events in the carcinogenic process, such as oxidative stress and inflammation, was widely documented. Interestingly, results from our research group and others have widened the action of sweet cherries to many hallmarks of cancer, namely metabolic reprogramming. The present review discusses the anticarcinogenic potential of sweet cherries by addressing their phytochemical composition, the bioaccessibility and bioavailability of specific bioactive compounds, and the existing knowledge concerning the effects against oxidative stress, chronic inflammation, deregulated cell proliferation and apoptosis, invasion and metastization, and metabolic alterations. Globally, this review highlights the prospective use of sweet cherries as a dietary supplement or in cancer treatment. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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29 pages, 2307 KiB

Open AccessReview

The Anti-Leukemic Activity of Natural Compounds

by Coralia Cotoraci, Alina Ciceu, Alciona Sasu, Eftimie Miutescu and Anca Hermenean

Molecules 2021, 26(9), 2709; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092709 - 05 May 2021

Cited by 14 | Viewed by 4353

Abstract

The use of biologically active compounds has become a realistic option for the treatment of malignant tumors due to their cost-effectiveness and safety. In this review, we aimed to highlight the main natural biocompounds that target leukemic cells, assessed by in vitro and in vivo experiments or clinical studies, in order to explore their therapeutic potential in the treatment of leukemia: acute myeloid leukemia (AML), chronic myeloid leukemia (CML), acute lymphocytic leukemia (ALL), and chronic lymphocytic leukemia (CLL). It provides a basis for researchers and hematologists in improving basic and clinical research on the development of new alternative therapies in the fight against leukemia, a harmful hematological cancer and the leading cause of death among patients. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)

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