Oleanonic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity

Giner-Larza, Eva M; Máñez, Salvador; Recio, M. C.; Giner, Rosa M.; Prieto, José M.; Cerdá-Nicolás, Miguel; Rı́os, José Luis

doi:10.1016/s0014-2999(01)01290-0

Cited by 174 publications

(115 citation statements)

References 14 publications

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“…Oleanolic acid (83) exhibited activity in the adjuvant-and formaldehyde-induced arthritis assays (Singh et al, 1992;Liu, 1995) and in several rodent edema models, including carrageenan-, dextran-, and phospholipase A 2 -induced paw edema (Singh et al, 1992;Liu, 1995;Recio et al, 1995;Giner-Larza et al, 2001) and croton oiland TPA-induced ear edema assays (Recio et al, 1995;Ismaili et al, 2001;Banno et al, 2004). In the last of these it was more active than indomethacin (Banno et al, 2004).…”

Section: Antiinflammatory and Autoimmune Conditionsmentioning

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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Section: Antiinflammatory and Autoimmune Conditionsmentioning

confidence: 99%

Medicinal chemistry and pharmacology of genus Tripterygium (Celastraceae)

et al. 2007

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“…Unfortunately, experiments addressing the effectiveness of astilbic acid 88 as a direct 5-LO inhibitor have not been performed yet. Similarly, the 11-keto-free PTs masticadienolic acid 84, oleanonic acid 85 and morolic acid 87 from Pistacia terebinthus (L.) [162], [163] or oleanolic acid 86 from Table 6), but data regarding 5-LO inhibition in cell-free assays are not available. Finally, the tricyclic diterpenoid abietic acid 91 was found to inhibit soybean LO (IC 50 = 29.5 mM) but the effectiveness on mammalian 5-LO and cellular LT biosynthesis remains to be determined [165].…”

Section: Pentacyclic Triterpenesmentioning

confidence: 99%

Inhibition of 5-Lipoxygenase Product Synthesis by Natural Compounds of Plant Origin

Werz¹

2007

Planta Med

153

135

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The biosynthesis of leukotrienes (LTs) is initiated by the transformation of free arachidonic acid to LTA 4 by 5-lipoxygenase (5-LO). Subsequent enzymatic conversion of LTA 4 yields LTB 4 and the cysteinyl-LTs C 4 , D 4 and E 4 . LTs have prominent functions in pathophysiology and are connected to numerous disorders including bronchial asthma, allergic rhinitis, inflammatory bowel and skin diseases, rheumatoid arthritis, cancer, osteoporosis and cardiovascular diseases. Pharmacological and genetic interruption of the 5-LO pathway or blockade of LT receptors, serving as means for intervention with LTs, may be of therapeutic value for certain related disorders. Natural or plant-derived substances were among the first 5-LO inhibitors identified in the early 1980 s. To date, a huge number of diverse plant-derived compounds have been reported to interfere with 5-LO product synthesis. However, many investigations have addressed the efficacy of a given compound solely in cellular test systems and analysis of direct interference with 5-LO has been neglected. In the first part of this review, the biology and molecular pharmacology of the 5-LO pathway is summarized in order to understand its overall regulation and complexity as well as to comprehend the possible points of attack of compounds that eventually lead to inhibition of 5-LO product formation in intact cells. In the second part, natural compounds that interfere with 5-LO product formation are compiled and grouped into structural classes, and the underlying molecular mechanisms and structureactivity relationships are discussed.

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“…Pistachio (Pistacia genus) is a member of the Anacardiaceae family native of the Mediterranean basin and of arid zones of Asia. Essential oils and lipophilic extracts of various parts of the plant including leaf, branch, stem, and seeds have been studied in vitro and in vivo for various healthy activities, with terpenoid derivatives playing a major role in the observed effects [12][13][14][15]. Among Pistacia species, P. vera L. is grown for its edible nuts.…”

Section: Introductionmentioning

confidence: 99%

Polymeric proanthocyanidins from Sicilian pistachio (Pistacia vera L.) nut extract inhibit lipopolysaccharide-induced inflammatory response in RAW 264.7 cells

et al. 2011

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Background Positive effects of pistachio nut consumption on plasma inflammatory biomarkers have been described; however, little is known about molecular events associated with these effects. Purpose We studied the anti-inflammatory activity of a hydrophilic extract from Sicilian Pistacia L. (HPE) in a macrophage model and investigated bioactive components relevant to the observed effects. Methods HPE oligomer/polymer proanthocyanidin fractions were isolated by adsorbance chromatography, and components quantified as anthocyanidins after acidic hydrolysis. Isoflavones were measured by gradient elution HPLC analysis. RAW 264.7 murine macrophages were pre-incubated with either HPE (1-to 20-mg fresh nut equivalents) or its isolated components for 1 h, then washed before stimulating with lipopolysaccharide (LPS) for 24 h. Cell viability and parameters associated with Nuclear Factor-jB (NF-jB) activation were assayed according to established methods including ELISA, Western blot, or cytofluorimetric analysis. Results HPE suppressed nitric oxide (NO) and tumor necrosis factor-a (TNF-a) production and inducible NO-synthase levels dose dependently, whereas inhibited prostaglandin E 2 (PGE 2 ) release and decreased cyclooxygenase-2 content, the lower the HPE amount the higher the effect. Cytotoxic effects were not observed. HPE also caused a dose-dependent decrease in intracellular reactive oxygen species and interfered with the NF-jB activation.Polymeric proanthocyanidins, but not isoflavones, at a concentration comparable with their content in HPE, inhibited NO, PGE 2 , and TNF-a formation, as well as activation of IjB-a. Oligomeric proanthocyanidins showed only minor effects. Conclusions Our results provide molecular evidence of anti-inflammatory activity of pistachio nut and indicate polymeric proanthocyanidins as the bioactive components. The mechanism may involve the redox-sensitive transcription factor NF-jB. Potential effects associated with pistachio nut consumption are discussed in terms of the proanthocyanidin bioavailability.

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Oleanonic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity

Cited by 174 publications

References 14 publications

Medicinal chemistry and pharmacology of genus Tripterygium (Celastraceae)

Medicinal chemistry and pharmacology of genus Tripterygium (Celastraceae)

Inhibition of 5-Lipoxygenase Product Synthesis by Natural Compounds of Plant Origin

Polymeric proanthocyanidins from Sicilian pistachio (Pistacia vera L.) nut extract inhibit lipopolysaccharide-induced inflammatory response in RAW 264.7 cells

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