Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds

Abstract Background: Ethnomedicinally, the family Polygonaceae is famous for the management of cancer. Various species of this family have been reported with anticancer potentials. This study was designed to isolate anticancer compounds from ethnomedicinally important species Polygonum barbatum. M...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Farooq,Umar, Naz,Sadia, Shams,Afshan, Raza,Yasir, Ahmed,Ayaz, Rashid,Umer, Sadiq,Abdul
Lenguaje:	English
Publicado:	Sociedad de Biología de Chile 2019
Materias:	Dihydrobenzofuran Polygonum barbatum Ethnomedicine Oral and lungs carcinoma Antiangiogenesis Anticancer
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0716-97602019000100201
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:scielo:S0716-97602019000100201
record_format	dspace
spelling	oai:scielo:S0716-976020190001002012019-10-10Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compoundsFarooq,UmarNaz,SadiaShams,AfshanRaza,YasirAhmed,AyazRashid,UmerSadiq,Abdul Dihydrobenzofuran Polygonum barbatum Ethnomedicine Oral and lungs carcinoma Antiangiogenesis Anticancer Abstract Background: Ethnomedicinally, the family Polygonaceae is famous for the management of cancer. Various species of this family have been reported with anticancer potentials. This study was designed to isolate anticancer compounds from ethnomedicinally important species Polygonum barbatum. Methods: The column chromatography was used for the isolation of compounds from the solvent fraction of P. barbatum. The characterization of isolated compounds was performed by various spectroscopic techniques like UV, IR, mass spectrometry and 1D-2D NMR spectroscopy. Keeping in view the ethnomedicinal importance of the family, genus and species of P barbatum, the isolated compounds (1–3) were screened for anticancer potentials against oral cancer (CAL-27) and lungs cancer (NCI H460) cell lines using MTT assay. Active compound was further investigated for apoptosis by using morphological changes and flow cytometry analysis. In vivo anti-angiogenic study of the isolated compounds was also carried using chorioallantoic membrane assay. Docking studies were carried out to explore the mechanism of anticancer activity. Results: Three dihydrobenzofuran derivatives (1–3) have been isolated from the ethyl acetate fraction of P. barbatum. The structures of isolated compounds were elucidated as methyl (2S,3S)-2-(3,4-dimethoxyphenyl)-4-((E)-3-ethoxy-3-oxoprop-1-en-1-yl)-7-methoxy-2,3-dihydrobenzo-furan-3-carboxylate (1), (E)-3-((2S,3S)-2-(3,4-dimethoxyphenyl)-7-methoxy-3-(methoxy carbonyl)-2,3-dihydrobenzofuran-4-yl)acrylic acid (2) and (2S,3 S)-4-((E)-2-carboxyvinyl)-2-(3,4-dimethoxyphenyl)-7-hydroxy-2,3-dihydrobenzofuran-3-carboxylic acid (3). The compound 1 was found to be more potent with IC50 of 48.52 ± 0.95 and 53.24 ± 1.49 against oral cancer cells as compared to standard drug (IC50 = 97.76 ± 3.44 μM). Both compound also inhibited lung cancer cells but at higher concentrations. Morphological and flow cytometry analysis further confirms that compound 1 induces apoptosis after 24 to 48 h treatment. In antiangiogenesis assay, compounds 1, 2 and 3 exhibited IC50 values of 8.2 ± 1.1,13.4 ± 1.1 and 57.7 ± 0.3 μM respectively. The docking studies revealed that the compounds under study have the potential to target the DNA and thymidylate synthase (TS). Conclusion: Based on its overwhelming potency against the tested cell lines and in angiogenesis assay, compound 1 can be further evaluated mechanistically and can be developed as anticancer drug candidate.info:eu-repo/semantics/openAccessSociedad de Biología de ChileBiological Research v.52 20192019-01-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0716-97602019000100201en10.1186/s40659-018-0209-0
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Dihydrobenzofuran Polygonum barbatum Ethnomedicine Oral and lungs carcinoma Antiangiogenesis Anticancer
spellingShingle	Dihydrobenzofuran Polygonum barbatum Ethnomedicine Oral and lungs carcinoma Antiangiogenesis Anticancer Farooq,Umar Naz,Sadia Shams,Afshan Raza,Yasir Ahmed,Ayaz Rashid,Umer Sadiq,Abdul Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds
description	Abstract Background: Ethnomedicinally, the family Polygonaceae is famous for the management of cancer. Various species of this family have been reported with anticancer potentials. This study was designed to isolate anticancer compounds from ethnomedicinally important species Polygonum barbatum. Methods: The column chromatography was used for the isolation of compounds from the solvent fraction of P. barbatum. The characterization of isolated compounds was performed by various spectroscopic techniques like UV, IR, mass spectrometry and 1D-2D NMR spectroscopy. Keeping in view the ethnomedicinal importance of the family, genus and species of P barbatum, the isolated compounds (1–3) were screened for anticancer potentials against oral cancer (CAL-27) and lungs cancer (NCI H460) cell lines using MTT assay. Active compound was further investigated for apoptosis by using morphological changes and flow cytometry analysis. In vivo anti-angiogenic study of the isolated compounds was also carried using chorioallantoic membrane assay. Docking studies were carried out to explore the mechanism of anticancer activity. Results: Three dihydrobenzofuran derivatives (1–3) have been isolated from the ethyl acetate fraction of P. barbatum. The structures of isolated compounds were elucidated as methyl (2S,3S)-2-(3,4-dimethoxyphenyl)-4-((E)-3-ethoxy-3-oxoprop-1-en-1-yl)-7-methoxy-2,3-dihydrobenzo-furan-3-carboxylate (1), (E)-3-((2S,3S)-2-(3,4-dimethoxyphenyl)-7-methoxy-3-(methoxy carbonyl)-2,3-dihydrobenzofuran-4-yl)acrylic acid (2) and (2S,3 S)-4-((E)-2-carboxyvinyl)-2-(3,4-dimethoxyphenyl)-7-hydroxy-2,3-dihydrobenzofuran-3-carboxylic acid (3). The compound 1 was found to be more potent with IC50 of 48.52 ± 0.95 and 53.24 ± 1.49 against oral cancer cells as compared to standard drug (IC50 = 97.76 ± 3.44 μM). Both compound also inhibited lung cancer cells but at higher concentrations. Morphological and flow cytometry analysis further confirms that compound 1 induces apoptosis after 24 to 48 h treatment. In antiangiogenesis assay, compounds 1, 2 and 3 exhibited IC50 values of 8.2 ± 1.1,13.4 ± 1.1 and 57.7 ± 0.3 μM respectively. The docking studies revealed that the compounds under study have the potential to target the DNA and thymidylate synthase (TS). Conclusion: Based on its overwhelming potency against the tested cell lines and in angiogenesis assay, compound 1 can be further evaluated mechanistically and can be developed as anticancer drug candidate.
author	Farooq,Umar Naz,Sadia Shams,Afshan Raza,Yasir Ahmed,Ayaz Rashid,Umer Sadiq,Abdul
author_facet	Farooq,Umar Naz,Sadia Shams,Afshan Raza,Yasir Ahmed,Ayaz Rashid,Umer Sadiq,Abdul
author_sort	Farooq,Umar
title	Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds
title_short	Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds
title_full	Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds
title_fullStr	Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds
title_full_unstemmed	Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds
title_sort	isolation of dihydrobenzofuran derivatives from ethnomedicinal species polygonum barbatum as anticancer compounds
publisher	Sociedad de Biología de Chile
publishDate	2019
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0716-97602019000100201
work_keys_str_mv	AT farooqumar isolationofdihydrobenzofuranderivativesfromethnomedicinalspeciespolygonumbarbatumasanticancercompounds AT nazsadia isolationofdihydrobenzofuranderivativesfromethnomedicinalspeciespolygonumbarbatumasanticancercompounds AT shamsafshan isolationofdihydrobenzofuranderivativesfromethnomedicinalspeciespolygonumbarbatumasanticancercompounds AT razayasir isolationofdihydrobenzofuranderivativesfromethnomedicinalspeciespolygonumbarbatumasanticancercompounds AT ahmedayaz isolationofdihydrobenzofuranderivativesfromethnomedicinalspeciespolygonumbarbatumasanticancercompounds AT rashidumer isolationofdihydrobenzofuranderivativesfromethnomedicinalspeciespolygonumbarbatumasanticancercompounds AT sadiqabdul isolationofdihydrobenzofuranderivativesfromethnomedicinalspeciespolygonumbarbatumasanticancercompounds
_version_	1718441583514222592

Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds

Ejemplares similares