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Absolute Configuration and Anti-Cancer Effect of Prenylated Flavonoids and Flavonostilbenes From Sophora Pachycarpa: Possible Involvement of Wnt Signaling Pathway Publisher Pubmed



Boozari M1 ; Nejad Ebrahimi S2 ; Soltani S3 ; Tayaraninajaran Z4 ; Emami SA1 ; Asili J1 ; Iranshahi M5
Authors
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Authors Affiliations
  1. 1. Department of Pharmacognosy, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran
  2. 2. Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G.C., Evin, Tehran, Iran
  3. 3. Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Medical Toxicology Research Center, Mashhad University of Medical Sciences, Mashhad, Iran
  5. 5. Biotechnology Research Center, Pharmaceutical Technology Institute, Mashhad University of Medical Sciences, Mashhad, Iran

Source: Bioorganic Chemistry Published:2019


Abstract

A new prenylated flavonostilbene, namely, alopecurone P together with three known compounds sophoraflavanone G, 2-(4-hydroxyphenyl)-2,3-dihydrobenzo[b]furan-3,4,6-triol and alopecurone J were characterized from the roots of Sophora pachycarpa. The absolute configuration of alopecurones J and P were characterized by comparison of experimental electronic circular dichroism (ECD) spectroscopy and simulated data using time-dependent density functional theory (TDDFT) for possible stereoisomers. The cytotoxic properties of isolated compounds have also been evaluated on two breast cancer cell lines (MCF-7 and MDA-MB-231) and normal cell line (NIH/3T3) using AlamarBlue®, flowcytometry and western blot assays. Alopecurone J and P showed cytotoxic effect on MCF-7 cell line through Wnt signaling pathway. It seems that the presence of lavandulyl substitution in C-8 position of flavanone structure increased the cytotoxic effect. © 2019 Elsevier Inc.
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