Ursolic Acid from <i>Plantago</i> <i>major</i>, a Selective Inhibitor of Cyclooxygenase-2 Catalyzed Prostaglandin Biosynthesis

Ringbom, Therese; Segura, Laura; Noreen, Ylva; Perera, Premila; Bohlin, Lars

doi:10.1021/np980088i

Cited by 157 publications

(109 citation statements)

References 28 publications

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“…A number of fatty acids occurring in the human diet, including a-linolenic acid, linoleic acid, docosahexaenoic acid and eicosapentaenoic acid as well as ursolic acid have previously been shown to inhibit COX-2 catalysed prostaglandin biosynthesis and markedly inhibited COX-2 in mice and in in vitro experiments. 33,[44][45][46] In line with this, olive oil and fish oil, which are complex mixtures of fatty acids have been reported to inhibit COX-2 protein expression. 47) Short chain fatty acids are known to modulate different molecular mechanisms of importance in colon cancer cells 48,49) and have been extensively studied for their ability to affect colonic function.…”

Section: )mentioning

confidence: 68%

NMR Metabolomic Analysis of Fecal Water from Subjects on a Vegetarian Diet

Pettersson

Karlsson

Choi

et al. 2008

Biological & Pharmaceutical Bulletin

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Plant based food contains a multiplicity of bioactive phytochemicals. These compounds are believed to contribute to the cancer protective effect of a diet high in fruit and vegetables.1,2) One group of phytochemicals is the cyclooxygenase-2 (COX-2) inhibitors, which potentially can act as preventive agents against colon cancer. Such compounds and their derivatives may pass through the digestive system and reach the colon where they exert chemopreventive effects.The water fraction of feces (fecal water) is believed to be in direct contact with the colonocytes, and its composition appears to be important for a healthy environment in the colon.3) It is believed that the fecal water composition roughly reflects the food intake and that it contains a mixture of compounds that may prevent and promote cancer development. A favorable change in the composition of fecal water would consequently decrease the risk of developing colon cancer.4) Fecal water is nowadays a common tool used in human intervention studies. It is used to test cellular responses in vitro in cell systems. [5][6][7][8] Such studies have shown that fecal water can modulate several cellular parameters such as genotoxicity, proliferation and apoptosis, all of which are relevant for tumorigenesis. [9][10][11] Other human intervention studies have indicated that it is possible to alter the pH and the composition of bile acids in fecal water with a change in the diet. 3,12) Another parameter that can be modulated by fecal water is the colonic COX-2 enzyme. We have recently shown that fecal waters from human volunteers inhibit COX-2 protein expression and prostaglandin E 2 (PGE 2 ) production in colonic cells. 13)COX-2 is the inducible form of two isoforms of cyclooxygenases, and it catalyzes the production of prostaglandins. This enzyme is not normally expressed in the colon, but it can be induced by growth factors, cytokines, tumor necrosis factor and lipopolysaccharides in situations of stress. [14][15][16] An over expression of COX-2 protein and an increased production of prostaglandins have been reported in patients with colon cancer, [17][18][19] and inhibition of the COX-2 enzyme has been a drug target over the past fifteen years. Today, there are several specific COX-2 inhibitors available on the market, but some of these synthetic drugs were recently reported to have severe side effects on the cardiovascular system. 20,21) To characterize a complex mixture of metabolites such as fecal water, a comprehensive metabolite profiling method is required. Metabolomic profiling of complex extracts is not an easy task to perform since they usually display a wide range of structural diversity. Of the possible analytical methods used in metabolomics, NMR provides a rapid, reproducible method well suited for identification of many metabolites and it has several advantages compared to other methods. It is not only the high information content of the resulting spectra for chemical structures but also the convenience in practical aspects such as high reproducibilit...

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Section: )mentioning

confidence: 68%

NMR Metabolomic Analysis of Fecal Water from Subjects on a Vegetarian Diet

Pettersson

Karlsson

Choi

et al. 2008

Biological & Pharmaceutical Bulletin

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“…Oleanolic acid (83) inhibited human leukocyte elastase (Facino et al, 1995;Safayhi and Sailer, 1997). It also inhibited COX-2, and COX-1 in one study (Ringborn et al, 1998) but not in another (Zhang et al, 2004b). Oleanolic acid (83) is a good inhibitor of adenosine deaminase (EC 3.5.4.4) (Koch et al, 1994), one isoform of which is increased in many cancers and immune diseases.…”

Section: Proinflammatory Enzymesmentioning

confidence: 99%

Medicinal chemistry and pharmacology of genus Tripterygium (Celastraceae)

et al. 2007

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Plants in the genus Tripterygium, such as Tripterygium wilfordii Hook. f., have a long history of use in traditional Chinese medicine. In recent years there has been considerable interest in the use of Tripterygium extracts and of the main bioactive constituent, the diterpene triepoxide triptolide (1), to treat a variety of autoimmune and inflammation-related conditions. The main mode of action of the Tripterygium extracts and triptolide (1) is the inhibition of expression of proinflammatory genes such as those for interleukin-2 (IL-2), inducible nitric oxide synthase (iNOS), tumor necrosis factor-α (TNF-α), cyclooxygenase-2 (COX-2) and interferon-gamma (IFN-γ). The efficacy and safety of certain types of Tripterygium extracts were confirmed in human clinical trials in the US and abroad. Over 300 compounds have been identified in the genus Tripterygium, and many of these have been evaluated for biological activity. The overall activity of the extract is based on the interaction between its components. Therefore, the safety and efficacy of the extract cannot be fully mimicked by any individual constituent. This review discusses the biochemical composition and biological and pharmacological activities of Tripterygium extracts, and their main bioactive components.

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“…Significantly improved the hyperglycemia, polydipsia, polyphagia, and also compensated weight loss of diabetic rats, in addition to treatment of candidiasis in normal and diabetic rats [179]. Ursolic acid [181]. Polysaccharides, lipids, caffeic acid derivatives, iridoid glycosides, terpenoids, alkaloids [182].…”

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confidence: 99%