Article

Ursolic acid and its esters: occurrence in cranberries and other Vaccinium fruit and effects on matrix metalloproteinase activity in DU145 prostate tumor cells.

Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, MA 02747, USA.
Journal of the Science of Food and Agriculture (Impact Factor: 1.88). 02/2011; 91(5):789-96. DOI: 10.1002/jsfa.4330
Source: PubMed

ABSTRACT Ursolic acid and its cis- and trans-3-O-p-hydroxycinnamoyl esters have been identified as constituents of American cranberries (Vaccinium macrocarpon), which inhibit tumor cell proliferation. Since the compounds may contribute to berry anticancer properties, their content in cranberries, selected cranberry products, and three other Vaccinium species (V. oxycoccus, V. vitis-idaea and V. angustifolium) was determined by liquid chromatography-mass spectroscopy. The ability of these compounds to inhibit growth in a panel of tumor cell lines and inhibit matrix metalloproteinase (MMP) activity associated with tumor invasion and metastasis was determined in DU145 prostate tumor cells.
The highest content of ursolic acid and esters was found in V. macrocarpon berries (0.460-1.090 g ursolic acid and 0.040-0.160 g each ester kg(-1) fresh weight). V. vitis-idaea and V. angustifolium contained ursolic acid (0.230-0.260 g kg(-1) ), but the esters were not detected. V. oxycoccus was lowest (0.129 g ursolic acid and esters per kg). Ursolic acid content was highest in cranberry products prepared from whole fruit. Ursolic acid and its esters inhibited tumor cell growth at micromolar concentrations, and inhibited MMP-2 and MMP-9 activity at concentrations below those previously reported for cranberry polyphenolics.
Cranberries (V. macrocarpon) were the best source of ursolic acid and its esters among the fruit and products tested. These compounds may limit prostate carcinogenesis through matrix metalloproteinase inhibition.

0 Bookmarks
 · 
64 Views
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Recent observational and clinical studies have raised interest in the potential health effects of cranberry consumption, an association that appears to be due to the phytochemical content of this fruit. The profile of cranberry bioactives is distinct from that of other berry fruit, being rich in A-type proanthocyanidins (PACs) in contrast to the B-type PACs present in most other fruit. Basic research has suggested a number of potential mechanisms of action of cranberry bioactives, although further molecular studies are necessary. Human studies on the health effects of cranberry products have focused principally on urinary tract and cardiovascular health, with some attention also directed to oral health and gastrointestinal epithelia. Evidence suggesting that cranberries may decrease the recurrence of urinary tract infections is important because a nutritional approach to this condition could lower the use of antibiotic treatment and the consequent development of resistance to these drugs. There is encouraging, but limited, evidence of a cardioprotective effect of cranberries mediated via actions on antioxidant capacity and lipoprotein profiles. The mixed outcomes from clinical studies with cranberry products could result from interventions testing a variety of products, often uncharacterized in their composition of bioactives, using different doses and regimens, as well as the absence of a biomarker for compliance to the protocol. Daily consumption of a variety of fruit is necessary to achieve a healthy dietary pattern, meet recommendations for micronutrient intake, and promote the intake of a diversity of phytochemicals. Berry fruit, including cranberries, represent a rich source of phenolic bioactives that may contribute to human health.
    Advances in Nutrition 01/2013; 4(6):618-632. · 3.20 Impact Factor
  • Source
    Central-European Journal of Immunology 12/2013; 38(4):480-485. · 0.38 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Breast cancer is the second leading cause of death from cancer in women in the United States. A growing emphasis is being placed on alternative medicine and dietary approaches toward prevention of potential diseases. Phytochemicals are bioactive compounds that are naturally present in foods that, when acting in synergy, bestow potential anti-cancer properties. Resveratrol, a phytoalexin, and ursolic acid, a pentacyclic triterpenoid, are two bioactive compounds that are at the forefront in scientific research. Previous animal studies have documented the anti-cancer properties of resveratrol on breast cancer cells and research groups have recently been able to identify the anti-cancer, anti-inflammatory and induction of apoptosis properties of resveratrol along with the signal transduction pathways that the compound affects. Ursolic acid has been cast into the limelight with the recent discovery documenting its anti-inflammation and anti-cancer activities by targeting signal pathways, especially in the prevention of breast cancer.
    Food Science and Human Wellness. 12/2012; 1(1):1–13.