Oleanolic acid and related derivatives as medicinally important compounds

PCSIR Laboratories Complex, Pharmaceutical Research Center, Karachi, Pakistan.
Journal of Enzyme Inhibition and Medicinal Chemistry (Impact Factor: 2.38). 08/2008; 23(6):739-56. DOI: 10.1080/14756360701633187
Source: PubMed

ABSTRACT Oleanolic acid has been isolated from chloroform extract of Olea ferruginea Royle after removal of organic bases and free acids. The literature survey revealed it to be biologically very important. In this review the biological significance of oleanolic acid and its derivatives has been discussed. The aim of this review is to update current knowledge on oleanolic acid and its natural and semisynthetic analogs, focussing on its cytotoxic, antitumer, antioxidant, anti-inflamatory, anti-HIV, acetyl cholinesterase, alpha-glucosidase, antimicrobial, hepatoprotective, anti-inflammatory, antipruritic, spasmolytic activity, anti-angiogenic, antiallergic, antiviral and immunomodulatory activities. We present in this review, for the first time, a compilation of the most relevant scientific papers and technical reports of the chemical, pre-clinical and clinical research on the properties of oleanolic acid and its derivatives.

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    ABSTRACT: Oleanolic acid (OA), a pentacyclic triterpene acid widely distributed in food and traditional herbal remedies, exhibits diverse therapeutic effects. OA has been subjected to various chemical modifications to optimize its anticancer effect. Among other analogs, 3-O-[N-(p-fluorobenzenesulfonyl)-carbamoyl]-oleanolic acid (PFOA) was semisynthesized from OA. This study evaluates the cytotoxic effects of PFOA on MDA-MB-231, MCF-7, BT-474, and T-47D human breast cancer cells. Acute treatment of PFOA inhibited breast cancer cell viability in a dose-dependent manner. Treatment of PFOA at cytotoxic doses significantly induced apoptosis in cancer cells as shown by flow cytometry analysis. Activation of apoptosis in MCF-7 and BT-474 cells seemed to be initiated through induction of Fas ligand, which resulted in activation of caspase-8 and PARP-1, whereas apoptosis in MDA-MB-231 cells was initiated by the activation of caspase-9, caspase-3 and PARP-1. The mechanism of apoptosis induction in T-47D involves activation of PARP-1. PFOA decreased the expression of EGFR, HER-2, MET and ERα in human breast cancer cell lines. These findings suggest that PFOA inhibits cell growth, activates apoptosis, and decreases the expression of key proteins involved in progression of breast cancer.
    European Journal of Pharmacology 07/2014; DOI:10.1016/j.ejphar.2014.07.011 · 2.68 Impact Factor
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    ABSTRACT: Pakistan is lacking in edible oils and large amounts of resources are being used to import these. Olea ferruginea Royle (Oleaceae), locally known as Kahu, is native to Northern part of the country, and the fruit of this tree is currently not being utilized for any useful purpose. The present study was conducted to exploit a new source of virgin olive oil (OWOT) based on chemical composition and quality parameters. The fruits from wild olive trees were collected from different locations in Pakistan (i.e. Bhara Kahu, Kotli Sattian and Dir Swat); whereas a reference sample (OCOT) of a local variety (Zaitoon II) Olea europaea L. was collected from Barani Agricultural Research Institute, Chakwal (BARIC) for comparison. The basic quality characteristics of oils such as free acidity, peroxide value, specific UV absorptions and sensory analysis demonstrated that the oils belong to the “lampante olive oil” commercial category due to low quality of processed olives. Some minor discrepancies with respect to the standard olive oil composition (linoleic acid slight exceeding 1% and traces of erucic acid and brassicasterol) were found that should be further studied to understand their etiology. Concerning minor compounds, tocopherols were found in low quantities whereas higher amounts of β-carotene and lutein were observed in OWOT compared to OCOT. Finally, OWOTs showed a relatively low quantity of hydrophilic phenols that proportionally expressed three times less antioxidant activity compared with OCOT. Careful control of fruit quality and good practices before olive milling could improve not only quality of the product, but also provide a new promising source of edible virgin oils.
    Food Research International 12/2013; DOI:10.1016/j.foodres.2013.09.029 · 3.05 Impact Factor
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    ABSTRACT: The mosquito larvicidal activities of different solvent extracts (chloroform, ethyl acetate, and methanol) from the leaves of Coccinia indica were studied. Among the extracts tested, the methanol extract showed the highest larvicidal activity against early fourth instar larvae of Culex quinquefasciatus (LC50 = 142 mg L), Aedes aegypti (LC50 = 158 mg L) and Anopheles stephensi (LC50 = 161 mg L) after 24 h of exposure period. The lowest larval mortality was observed with the ethyl acetate extract with the LC50 values of 927, 872, and 730 mg L against Cx. quinquefasciatus, Ae. aegypti, and An. stephensi, respectively. The chloroform extract showed the moderate larvicidal activity against the mosquito species tested with the LC50 values from 446 to 546 mg L. A new triterpene was isolated from the methanol extract using bio-assay guided separation and identified as an oleanolic acid derivative by NMR, IR and mass spectral studies. The compound showed prominent larvicidal activity against Cx. quinquefasciatus, Ae. aegypti and An. stephensi with the LC50 values of 5.6, 5.0, and 4.8 mg L, respectively. The results of the present investigation offer an opportunity for developing alternatives to rather expensive and environmentally hazardous organic insecticides.
    Toxicological and Environmental Chemistry 08/2012; 94(7):1-8. DOI:10.1080/02772248.2012.705288 · 0.72 Impact Factor