HCV Protease Inhibitory, Cytotoxic and Apoptosis-Inducing Effects of Oleanolic Acid Derivatives

Ma, Cui; Wu, Xiu-Hong; Hattori, Masao; Wang, Xijun; Kano, Yoshihiro

doi:10.18433/j3dw2d

Cited by 29 publications

(22 citation statements)

References 13 publications

(20 reference statements)

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“…The major compound of L. salicaria, oleanolic acid (8), is a signifi cant antitumour agent against the HCT15 cell line (Li et al, 2002). Finally, triterpene derivatives were found to inhibit the growth of HepG2 cells in a concentration-dependent manner (Ma et al, 2009). Antiproliferative and apoptosis-inducing activities of β-sitosterol (11) in human leuke- (Park et al, 2007).…”

Section: Resultsmentioning

confidence: 99%

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Chemical Constituents and Cytotoxic Effect of the Main Compounds of Lythrum salicaria L.

Manayi

Saeidnia

Ostad

et al. 2013

Zeitschrift Für Naturforschung C

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Lythrum salicaria L. (Lythraceae), a herbaceous plant growing widely in Iran, has been well known for many centuries for its astringent and styptic properties. A phytochemical investigation of this plant, based on spectroscopic analysis, identifi ed fourteen compounds: 5-hydroxypyrrolidin-2-one (1), umbelliferone-6-carboxylic acid (2), 3,3',4'-tri-O-methylellagic acid-4-O-β-D-(2"-acetyl)-glucopyranoside (3), 3,3',4'-tri-O-methylellagic acid-4-O-β-D-glucopyranoside (4), daucosterol (5), phytol (6), dodecanoic acid (7), oleanolic acid (8), 3,3',4'-tri-O-methylellagic acid (9), corosolic acid (10), β-sitosterol (11), peucedanin (12), buntansin (13), and erythrodiol (14). All compounds, except for 8 and 11, have been isolated from L. salicaria for the fi rst time. Cytotoxic activities of the compounds were examined against three cancerous cell lines, colon carcinoma (HT-29), leukemia (K-562), and breast ductal carcinoma (T47D), and Swiss mouse embryo fi broblast (NIH-3T3) cells using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and methotrexate as positive control. Compounds 5, 10, 11, and 14 were the most active against the HT-29 cell line with IC 50 values of 192.7, 36.8, 38.2, and 12.8 μg/mL, respectively. Compounds 14, 11, 5, and 10 were 6.4, 2.8, 2.6, and 1.4 times, respectively, more selective than methotrexate. Compound 5 was the most active against the K-562 cell line (IC 50 = 50.2 μg/mL), with a selectivity exceeding that of methotrexate 13.3 times. The results of the cytotoxic assay confi rmed that growth and proliferation of the cancer cell lines are predominantly infl uenced by triterpene derivatives and sterols of this plant. ., 2003;Lopez et al., 2008;Tunalier et al., 2007). The plant extract decreases the blood glucose level in both hyperglycaemic and normoglycemic rats and rabbits (Lamela et al., 1986;Torres and Suarez, 1980). Flowering aerial parts of the plant have been traditionally used for the treatment of diarrhea, chronic intestinal catarrh, haemorrhoids, eczema, varicose veins, bleeding of the gums, and vaginitis (Mantle et al., 2000;Rauha et al., 2000). Evaluation of the antidiarrheal effect of Salicairine ® , a formulated medication, demonstrated that there was either a signifi cant increase in the colon net fl uid absorption or a decrease in the net fl uid secretion (Brun et al., 1997).We have previously analysed the extract and fractions of L. salicaria for cytotoxic activity against cancer cell lines using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Ethyl acetate and chloroform fractions of the plant exhibited cytotoxicity toward the T47D cancer cell line with IC 50 values of 63.1 and 108.2 μg/mL, respectively (Khanavi et al., 2011). The objective of the present study was the isolation and characterization of major constituents of L. salicaria through chromatographic and spectroscopic methods, respectively. We also demonstrated cytotoxic effects of the purifi ed compounds using the MTT assay against the three cancerous c...

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Section: Resultsmentioning

confidence: 99%

“…Cancer has become one of the most devastating diseases of humankind in the world (Ma et al, 2009). Natural products or their related components constitute more than half of the drugs used in cancer therapy (Newman and Cragg, 2007).…”

Section: Introductionmentioning

confidence: 99%

Chemical Constituents and Cytotoxic Effect of the Main Compounds of Lythrum salicaria L.

Manayi

Saeidnia

Ostad

et al. 2013

Zeitschrift Für Naturforschung C

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“…OA (17) was also found to be an HCV protease inhibitor. 91 Based on this lead compound, 29 OA derivatives were synthesized and tested for their inhibitory activity on hepatitis C viral protease. The derivatives of dicarboxylic acid hemiesters showed potent activity against HCV protease.…”

Section: Hcv Protease Inhibitorsmentioning

confidence: 99%

Recent progress in the antiviral activity and mechanism study of pentacyclic triterpenoids and their derivatives

Xiao

Tian

Wang

et al. 2018

Medicinal Research Reviews

162

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Viral infections cause many serious human diseases with high mortality rates. New drug-resistant strains are continually emerging due to the high viral mutation rate, which makes it necessary to develop new antiviral agents. Compounds of plant origin are particularly interesting. The pentacyclic triterpenoids (PTs) are a diverse class of natural products from plants composed of three terpene units. They exhibit antitumor, anti-inflammatory, and antiviral activities. Oleanolic, betulinic, and ursolic acids are representative PTs widely present in nature with a broad antiviral spectrum. This review focuses on the recent literatures in the antiviral efficacy of this class of phytochemicals and their derivatives. In addition, their modes of action are also summarized.

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“…This compound is reported to have a wide array of biological properties including anti-nociceptive, anti-inflammatory, anti-cancer, anti-diabetic, hepatoprotective, antioxidant, and immunomodulatory properties [5][6][7]. Indeed in countries such as China, OA is sold as a dietary supplement and is supplied as an over-the-counter drug for treatment of liver diseases [8]. However, although OA seems to have much therapeutic potential, the use of this compound has been limited by its poor solubility in aqueous solutions [9] and its low bioavailability on oral treatment [10].…”

Section: Introductionmentioning

confidence: 99%

“…This has led to the search for semisynthetic derivatives of the compound which might have improved solubility and bioavailability on oral treatment as well as better effects. Indeed, some amino acid derivatives of OA have shown potent cytotoxic and apoptosis-inducing effects on Hep G2 cells compared to OA [8]. In a recent paper, Habila et al [11] showed that C-3 modification of OA was accompanied by improved anti-microbial properties compared to the parent compound indicating that molecular modification of compounds obtained from natural products could provide more potent molecules for therapeutic use [12,13].…”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory and Membrane-Stabilizing Properties of Two Semisynthetic Derivatives of Oleanolic Acid

Nkeh-Chungag¹,

Oyedeji

Oyedeji³

et al. 2014

Inflammation

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Acetylation and methylation semisynthesis of oleanolic acid (OA) isolated from Syzygium aromaticum L. yielded two compounds: 3-acetoxyoleanolic acid (3-AOA) and 3-acetoxy, 28-methylester oleanolic acid (3-A,28-MOA). Anti-inflammatory properties of these compounds were assessed using the serotonin and fresh egg albumin-induced inflammatory test models in male Wistar rats weighing 250-300 g. Furthermore, erythrocyte membrane-stabilizing property of these compounds was evaluated in the heat- and hypotonicity-induced in vitro hemolysis test models. The two semisynthetic compounds significantly (p < 0.05) inhibited albumin-induced inflammation better than OA and indomethacin from 1-5 h post administration. Both compounds were membrane stabilizing in heat-induced hemolysis test while only 3-AOA showed membrane-stabilizing effects in a hypotonic milieu. Semisynthesis of OA yielded two compounds which had better in vivo anti-inflammatory and in vitro membrane-stabilizing properties.

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HCV Protease Inhibitory, Cytotoxic and Apoptosis-Inducing Effects of Oleanolic Acid Derivatives

Cited by 29 publications

References 13 publications

Chemical Constituents and Cytotoxic Effect of the Main Compounds of Lythrum salicaria L.

Chemical Constituents and Cytotoxic Effect of the Main Compounds of Lythrum salicaria L.

Recent progress in the antiviral activity and mechanism study of pentacyclic triterpenoids and their derivatives

Anti-Inflammatory and Membrane-Stabilizing Properties of Two Semisynthetic Derivatives of Oleanolic Acid

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