A new triterpene and protective effect ofPeriploca somaliensisBrowicz fruits against CCl₄-induced injury on human hepatoma cell line (Huh7)

Abstract

The potential hepatoprotective effect of the methanolic extract of Periploca somaliensis Browicz fruits, its different fractions (n-hexane, chloroform and n-butanol) and the major isolated compound ursolic acid was evaluated using the human hepatoma cell line (Huh7) based on the changes in the activity of aspartate aminotransferase, alanine transaminase, glutathione and superoxide dismutase. Each sample was tested at three different concentrations (1000, 100 and 10 μg/mL). All tested samples exhibited a potent concentration-independent cytoprotective effect relative to silymarin as a reference standard. Chromatographic fractionation of the chloroform-soluble fraction of the methanol extract of P. somaliensis Browicz fruits afforded two known triterpenes, namely ursolic acid, and 11α,12α-epoxy-3β-hydroxy-olean-13β,28-olide, and a newly discovered one, namely 3β-hydroxy-urs-11-en-13β,28-olide. The structures of the isolated compounds were elucidated by the analysis of 1D and 2D NMR spectral data.

Ursolic Acid Derivatives Induced Apoptosis and Reduces the NF-<i>κ</i>B in Human Lung Adenocarcinoma Cells

“…Ursolic acid is a pentacyclic triterpene extracted and purified from many plant species that presents considerable pharmacological effects [5]- [11] [16]. In the present study, some of the UA derivative compounds were able to reduce the viability of A549 cells and, among these, the UAD1 showed better results.…”

“…Despite the advances in the chemotherapy, the results of the lung cancer treatment are not good enough; being necessary the seeking of new therapeutic strategies and the development of new drugs [4]. In this context, the ursolic acid (UA), a triterpene widely distributed in plant species, becomes the target of studies that investigate its antitumor potential [5] [6] [7] [8]. Moreover, structural modifications in the carbons 3, 12 and 28, and the rings A, C and D (Figure 1) are the potential target to increase the antimicrobial, antioxidant, anti-inflammatory or antitumor activities of the ursolic acid [9] [10] [11].…”

A chemically characterized ethanolic extract of Thai Perilla frutescens (L.) Britton fruits (nutlets) reduces oxidative stress and lipid peroxidation in human hepatoma (HuH7) cells

“…We hypothesized that differential extracts of Thai perilla nutlets would vary in their chemical composition and therefore also in their potency of biological activities. This study chemically characterizes different extracts of Thai perilla nutlets and investigates both their antioxidant activity using a suite of assays including the 2,2′‐azinobis‐(3‐ethylbenzothiazoline‐6‐sulphonic acid) diammonium salt (ABTS) and 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) radical scavenging assays, the 2,2′‐azo‐bis(2‐amidinopropane) dihydrochloride (AAPH)‐induced hemolysis assay; a cell‐based model in the study of free‐radical‐induced disruption of cell membranes (Pervin et al, ; Sekiya et al, ), and their protective effects against iron‐induced oxidative stress in human hepatocellular carcinoma (HuH7) cells; an established model to investigate the hepatoprotective effects of plant extracts (Abdel‐Monem, Kandil, Abdel‐Naim, & Abdel‐Sattar, ; Torres‐Gonzalez et al, ).…”

Genus Periploca (Apocynaceae): A Review of Its Classification, Phytochemistry, Biological Activities and Toxicology

“…In 1971, oleanolic acid ( 172 ), together with maslinic acid ( 175 ), was first isolated from the genus Periploca [70]. Two known triterpenes ( 177 , 178 ) [10,87] characterized by a 13,28-lactone ring were discovered from P. laevigata and P. somaliensis , respectively. Additionally, three new triterpenoid acids of the oleanane series, named P1, P2, P3 ( 183 – 185 ), were isolated from the twigs of P. calophylla , without definite chemical structures [89].…”

“…Its mechanism of promoting wound healing was intensely associated with the activation of the Src/ERK and PI3K/Akt pathways mediated by Na/K-ATPase [200]. Moreover, Abdel-Monem and co-workers [10] reported that ursolic acid played an important role in the protective effect against CCl 4 -induced injury on human hepatoma cell line (Huh7). Additionally, the antiacetylcholinesterase activities of triterpenes 199 and 198 with esterification of the alcohol function at C-3 were lower than that of lupeol ( 197 ).…”