Structure–activity relationships of diverse ACGs against multidrug resistant human lung cancer cell line A549/Taxol

Yuan, Fangyan; Bai, Ganggang; Chen, Yong; Miao, Yunjie; Chen, Jianwei; Li, Xiang

doi:10.1016/j.bmcl.2014.12.088

Cited by 18 publications

(8 citation statements)

References 16 publications

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“…Over 500 AAs have been described to date; these compounds are characterized by a long aliphatic chain with an α, β-unsaturated γ-lactone ring and 0–3 tetrahydrofuran (THF) rings (Yuan et al, 2015), and have shown cytotoxic activity against different human cancer cell lines (i.e., lung, breast, colon, kidney, pancreas, prostate, liver, and bladder) (reviewed in Zeng et al, 1996; Chávez and Mata, 1998; Wang et al, 2002; Yuan et al, 2003; Mangal et al, 2016; Miao et al, 2016a; Miao et al, 2016b) besides in vivo antitumor activity (Chen et al, 2012a; Chen et al, 2012b). Herein, we reviewed the most recent reports about AAs in the drug discovery–oncology field.…”

Section: Introductionmentioning

confidence: 99%

Selective Acetogenins and Their Potential as Anticancer Agents

et al. 2019

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The Kingdom Plantae has provided several successful drugs for the treatment of different diseases, including cancer, and continues to be a source of new possible therapeutic molecules. For example, the annonaceous acetogenins (AAs) are secondary metabolites found in the Annonaceae family, which are plants employed in traditional medicine for the treatment of cancer and various other diseases. These polyketides are inhibitors of Complex I in the respiratory chain of tumor cells, a process that is closely related to tumor metabolism, cell death, apoptosis, and autophagy. The goal of this review is to update readers on the role of the AAs as antitumor agents using in vitro and in vivo studies to demonstrate their importance in the area of oncology drug discovery. For this purpose, we performed a literature search in the PubMed scientific database using a range of keywords, including acetogenins and cancer, acetogenins antitumor activity, acetogenins and cytotoxicity, and acetogenins mechanism of action, among others. As a result, we found that the AAs are cytotoxic compounds that can induce apoptosis, cell cycle arrest, and autophagy in vitro , in addition to exhibiting tumor growth inhibition in vivo . The functional group related to their antineoplastic activity is suggested to be the mono or bis tetrahydrofuran ring accompanied by two or more hydroxy groups. The versatility of the AA bioactivity therefore renders them potential therapeutic agents for cancer treatment. It is therefore apparent that nature is worth further examination to aid in the discovery of more effective, accurate, and less harmful therapies in the fight against cancer.

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Section: Introductionmentioning

confidence: 99%

Selective Acetogenins and Their Potential as Anticancer Agents

et al. 2019

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“…The inhibition of complex I (NADH-ubiquinone oxidoreductase) of mitochondrial electron transport systems [ 14 , 15 , 16 ], inhibition of glucose uptake (they are potent modulators of glucose transporters) [ 17 ] and a target of the hypoxia-inducible factor-1 (HIF-1) have been well established as modes of action [ 18 ]. Furthermore, the effectiveness of ACGs against multidrug-resistant human mammary adenocarcinoma and lung cancer cell lines has been described, with better results obtained than for conventional treatments [ 5 , 19 ]. In spite of these advantages, this kind of compound has very low water solubility and their use in clinical or dietary supplement applications is therefore limited.…”

Section: Introductionmentioning

confidence: 99%

Bio-Guided Isolation of Acetogenins from Annona cherimola Deciduous Leaves: Production of Nanocarriers to Boost the Bioavailability Properties

et al. 2020

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Annonaceous acetogenins (ACGs) are lipophilic polyketides isolated exclusively from Annonaceae. They are considered to be amongst the most potent antitumor compounds. Nevertheless, their applications are limited by their poor solubility. The isolation of ACGs from Annona cherimola leaves, an agricultural waste, has not been reported to date. Molvizarin (1) cherimolin-1 (2), motrilin (3), annonacin (4) and annonisin (5) are isolated for the first time from A. cherimola deciduous leaves. Annonacin was found to be four- and two-times more potent in tumoral cells (HeLa, 23.6% live cells; IGROV-1, 40.8% live cells for 24 h) than in HEK-293 at 50 µM (24 h, 87.2% live cells). Supramolecular polymer micelles (SMPMs) were synthesized to encapsulate the major ACG isolated, annonacin, in order to improve its solubility in aqueous media. The bioavailability of this compound was increased by a factor of 13 in a simulated human digestive system when compared with free annonacin and an encapsulation efficiency of 35% was achieved. In addition, the cytotoxic activity of SMPMs that hosted annonacin (100 µM, 24 h, 5.8% live cells) was increased compared with free annonacin in water (100 µM, 24 h, 92% live cells). These results highlight the use of by-products of A. cherimola, and their pure compounds, as a promising source of anticancer agents. The use of SMPMs as nanocarriers of ACGs could be an alternative for their application in food field as nutraceutical to enhance the administration and efficacy.

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“…The sugar apple (Annona squamosa L.) has the following bioactive compounds: diterpenes, alkaloids, and acetogenins in its composition, which confer potential antioxidant, antimicrobial, cytotoxic activity, antitumor, epilepsy, pesticide, vermicide, antimicrobial, immunosuppressant, dysuria, fever, antiemetic, and antimalarial properties 2,3,4,5,6,7,8 . The sugar apple belongs to the Annonaceae family, which is represented by 120 genera with 2000 distinct species of plants.…”

Section: Introductionmentioning

confidence: 99%

Chemical characterization, antimicrobial and antioxidant activity of sugar-apple (Annona squamosa L.) pulp extract

et al. 2020

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Synthetic preservatives are widely present in processed foods, but most of them have carcinogenic potential, requiring the development of new natural alternatives such as fruit extracts, for microbial control. The objective of the study was to evaluate the chemical characterization, antioxidant, and antimicrobial activity of the sugar apple pulp (Annona squamosa L.). Physicochemical characteristics were evaluated, an extract was prepared, and its antioxidant activity by DPPH method and antimicrobial by disk diffusion. Minimal inhibitory concentration and minimum bactericidal concentration against strains of Salmonella typhimurium, Escherichia coli, Listeria monocytogenes, and Staphylococcus aureus were evaluated. The physicochemical analysis revealed that sugar apple pulp had 75.0% moisture, 3.0% ash, 4.0% protein, 0.2% lipids, 3.3% fibers, and 14.5% carbohydrates. The antioxidant activity of the extract by the DPPH method was 20.6%. The pulp extract from the sugar apple had inhibition zone for Staphylococcus aureus, satisfactory inhibitory effect against Staphylococcus aureus, Escherichia coli, Listeria monocytogenes, and Salmonella Typhimurium, but did not present a bactericidal effect. Sugar apple pulp presents adequate levels of nutrients and potential for food application due to its microbiological activity and antioxidant properties.

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Structure–activity relationships of diverse ACGs against multidrug resistant human lung cancer cell line A549/Taxol

Cited by 18 publications

References 16 publications

Selective Acetogenins and Their Potential as Anticancer Agents

Selective Acetogenins and Their Potential as Anticancer Agents

Bio-Guided Isolation of Acetogenins from Annona cherimola Deciduous Leaves: Production of Nanocarriers to Boost the Bioavailability Properties

Chemical characterization, antimicrobial and antioxidant activity of sugar-apple (Annona squamosa L.) pulp extract

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