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: 2.33). 08/2008; 23(6):739-56. DOI: 10.1080/14756360701633187
Source: PubMed


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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    • "Oleanolic acid and its derivatives possess several promising pharmacological effects, such as antioxidant, anti-inflammatory, hepatoprotective , cardioprotective, antipruritic, spasmolytic, antiallergic, antimicrobial and antiviral activities (Somova et al. 2003; Dzubak et al. 2006; Sultana and Ata 2008; Wang et al. 2010). Emerging studies indicate that oleanolic acid and other oleanane triterpenoids influence multiple intracellular signaling pathways and exert chemopreventive and antitumor activities in various in vitro and in vivo model systems (Ovesná et al. 2004; Sultana and Ata 2008; Sogno et al. 2009; Zhang and Popovich 2009; Kuttan et al. 2011; Shanmugam et al. 2012). Several animal and human studies have indicated systemic absorption, bioavailability and tissue distribution of oleanolic acid following oral administration (Song et al. 2006; Jeong et al. 2007; Yin et al. 2012). "
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    ABSTRACT: Breast cancer is one of the most frequently diagnosed cancers and major cause of death in women in the world. Emerging evidence underscores the value of dietary and non-dietary phytochemicals, including triterpenoids, in the prevention and treatment of breast cancer. Oleanolic acid, an oleanane-type pentacyclic triterpenoid, is present in a large number of dietary and medicinal plants. Oleanolic acid and its derivatives exhibit several promising pharmacological activities, including antioxidant, anti-inflammatory, hepatoprotective, cardioprotective, antipruritic, spasmolytic, antiallergic, antimicrobial and antiviral effects. Numerous studies indicate that oleanolic acid and other oleanane triterpenoids modulate multiple intracellular signaling pathways and exert chemopreventive and antitumor activities in various in vitro and in vivo model systems. A series of novel synthetic oleanane triterpenoids have been prepared by chemical modifications of oleanolic acid and some of these compounds are considered to be the most potent anti-inflammatory and anticarcinogenic triterpenoids. Accumulating studies provide extensive evidence that synthetic oleanane derivatives inhibit proliferation and induce apoptosis of various cancer cells in vitro and demonstrate cancer preventive or antitumor efficacy in animal models of blood, breast, colon, connective tissue, liver, lung, pancreas, prostate and skin cancer. This review critically examines the potential role of oleanolic acid, oleanane triterpenoids and related synthetic compounds in the chemoprevention and treatment of mammary neoplasia. Both in vitro and in vivo studies on these agents and related molecular mechanisms are presented. Several challenges and future directions of research to translate already available impressive preclinical knowledge to clinical practice of breast cancer prevention and therapy are also presented.
    No preview · Article · Dec 2014 · Phytochemistry Reviews
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    • "Oleanolic acid (OA), a pentacyclic triterpene acid, is widely distributed in food and traditional medicinal herbs. Recently it has attracted considerable attention due to its different therapeutic activities including its anti-inflammatory, antioxidant, immunomodulatory , antiviral, and anticancer properties (Sultana and Ata, 2008). OA has been shown to mediate its anticancer effect through modulation of multiple molecular targets. "
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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.
    Full-text · Article · Jul 2014 · European Journal of Pharmacology
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    • "Locally, fruits are consumed raw (Ahmad, Ali, Bibi, Marwat, & Hassan, 2006; Zabihullah et al., 2006). Sultana and Ata (2008) have recently isolated, oleanolic acid, a biologically important compound, from the chloroform extract of O. ferruginea oil. Since the production of olive oil is much lower than demand due to a steady increase in population growth, it is very difficult to maintain a balance between demand and supply. "
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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.
    Full-text · Article · Dec 2013 · Food Research International
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