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1.
Nat Prod Res ; 31(18): 2085-2090, 2017 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-28064519

RESUMEN

Two new annonaceous acetogenins squamocin P (2) and annosquatin III (3) and one new ACG precursor dieporeticenin B (1) along with five known precursors (4-8) were isolated from the seeds of Annona squamosa. Their structures were ascertained by chemical methods and various spectral evidences. These compounds showed inhibitory effects against three multidrug-resistant (MDR) cancer cell lines. Compound 2 and 3 displayed selective cytotoxicity against SMMC 7721/T (IC50 0.435 and 1.79 µM) and MCF-7/ADR (IC50 values 3.34 and 4.04 µM).


Asunto(s)
Acetogeninas/química , Acetogeninas/farmacología , Annona/química , Antineoplásicos Fitogénicos/farmacología , Acetogeninas/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Línea Celular Tumoral , Resistencia a Antineoplásicos/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales/métodos , Humanos , Concentración 50 Inhibidora , Estructura Molecular , Extractos Vegetales/química , Semillas/química
2.
J Ethnopharmacol ; 193: 362-367, 2016 Dec 04.
Artículo en Inglés | MEDLINE | ID: mdl-27566205

RESUMEN

CONTEXT: Custard apple (Annona squamosa Linn.) is an edible tropical fruit, and its seeds have been used to treat "malignant sore" (cancer) and other usage as insecticide. A comparison of extraction processes, chemical composition analysis and antitumor activity of A. squamosa seed oil (ASO) were investigated. MATERIALS AND METHODS: The optimal extraction parameters of ASO were established by comparing percolation, soxhlet, ultrasonic and SFE-CO2 extraction methods. The chemical composition of fatty acid and content of total annonaceous acetogenins (ACGs) of ASO was investigated by GC-MS and colorimetric assay, and anti-tumor activity of ASO was tested using H22 xenografts bearing mice. RESULTS: The optimal extraction parameters of ASO were obtained as follows: using soxhlet extraction method with extraction solvent of petroleum ether, temperature of 80°C, and extraction time of 90min. Under these conditions, the yield of ASO was 22.65%. GC-MS analysis results showed that the main chemical compositions of fatty acid of ASO were palmitic acid (9.92%), linoleic acid (20.49%), oleic acid (56.50%) and stearic acid (9.14%). The total ACGs content in ASO was 41.00mg/g. ASO inhibited the growth of H22 tumor cells in mice with a maximum inhibitory rate of 53.54% by oral administration. Furthermore, it was found that ASO exerted an antitumor effect via decreasing interleukin-6 (IL-6), janus kinase (Jak) and phosphorylated signal transducers and activators of transcription (p-Stat3) expression. DISCUSSION AND CONCLUSION: The results demonstrated that ASO suppressed the H22 solid tumor development may due to its main chemical constituents unsaturated fatty acid and ACGs via IL-6/Jak/Stat3 pathway. ASO may be a potential candidate for the treatment of cancer.


Asunto(s)
Annona/embriología , Antineoplásicos/farmacología , Aceites de Plantas/farmacología , Semillas/química , Animales , Colorimetría , Interleucina-6/biosíntesis , Quinasas Janus/biosíntesis , Ratones , Factor de Transcripción STAT3/biosíntesis , Ensayos Antitumor por Modelo de Xenoinjerto
3.
J Ethnopharmacol ; 184: 187-95, 2016 May 26.
Artículo en Inglés | MEDLINE | ID: mdl-26965366

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Annona squamosa Linn (Annonaceae) is a commonly used and effective traditional Chinese medicine (TCM) especially in the South China. The seeds of Annona squamosa Linn (SAS) have been used as a folk remedy to treat "malignant sores" (cancer) in South of China, but they also have high toxicity on human body. AIM OF THE STUDY: To discover the potential biomarkers in the mice caused by SAS. MATERIALS AND METHODS: We made metabonomics studies on the toxicity of SAS by ultraperformance liquid-chromatography high-definition mass spectrometry coupled with pattern recognition approach and metabolic pathways analysis. RESULTS: The significant difference in metabolic profiles and changes of metabolite biomarkers between the Control group and SAS group were well observed. 11 positive ions and 9 negative ions (P<0.05) were indicated based on UFLC-QTOF-HDMS. The metabolic pathways of SAS group are discussed according to the identified endogenous metabolites, and eight metabolic pathways are identified using Kyoto Encyclopedia of Genes and Genomes (KEGG). CONCLUSIONS: The present study demonstrates that metabonomics analysis could greatly facilitate and provide useful information for the further comprehensive understanding of the pharmacological activity and potential toxicity of SAS in the progress of them being designed to a new anti-tumor medicine.


Asunto(s)
Annona , Metaboloma/efectos de los fármacos , Extractos Vegetales/toxicidad , Animales , Biomarcadores/orina , Cromatografía Liquida/métodos , Femenino , Hígado/efectos de los fármacos , Hígado/patología , Metabolómica , Ratones Endogámicos ICR , Reconocimiento de Normas Patrones Automatizadas , Semillas , Espectrometría de Masa por Ionización de Electrospray
4.
Zhongguo Zhong Yao Za Zhi ; 41(10): 1884-1888, 2016 May.
Artículo en Chino | MEDLINE | ID: mdl-28895338

RESUMEN

10 kinds of annonaceous acetogenins were selected for antitumor activity testing against human lung cancer cell line A549/Taxol and the structure activity relationship was analyzed.MTT assay was used to detect the inhibitory activities of 10 kinds of annonaceous acetogenins and positive drugs against A549/Taxol cells, respectively uvariamicin-Ⅲ(1), uvariamicin-Ⅱ(2), annosquacin D(3), desacetyluvaricin(4), annosquatin A(5), squamostatin D(6), bullatacin(7), squamocin(8), motrilin(9), annosquatin B(10), verapamil and cisplatin. Annonaceous acetogenins showed significant inhibitory activities against A549/Taxol cells, and were more potent than the positive drug verapamil and cisplatin.The more carbon atoms between the tetrahydrofuran ring and the lactone ring of annonaceous acetogenins exhibited more potency.Besides,ACGs with two substituted hydroxyl showed more potency than the compounds with three substituted hydroxyl in the bis-adjacent-THF ACGs. Furthermore, ACGs with three substituted hydroxyl showed more potency than the compounds with four substituted hydroxyl among the no bis-adjacent-THF ACGs.


Asunto(s)
Acetogeninas/farmacología , Resistencia a Múltiples Medicamentos , Resistencia a Antineoplásicos , Células A549 , Acetogeninas/química , Humanos , Neoplasias Pulmonares/tratamiento farmacológico , Relación Estructura-Actividad
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