Ursolic acid and its esters: occurrence in cranberries and other Vaccinium fruit and effects on matrix metalloproteinase activity in DU145 prostate tumor cells.
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.
- [Show abstract] [Hide abstract]
ABSTRACT: The chemical composition of the lipohilic extracts of the inner and outer barks of Eucalyptus grandis x globulus, cultivated in Portugal, was studied by gas chromatography–mass spectrometry. The two bark fractions show different chemical compositions. b-Sitosterol is the most abundant compound in the inner bark (82 mg kg−1), while long chain aliphatic alcohols are the main family of components accounting for 208 mg kg−1. In the outer bark fraction, triterpenic compounds (8.5 g kg−1) are the most abundant ones from which methyl morolate (methyl 3-hydroxyolean-18-en-28-oate) is the chief component (3 g kg−1). This oleanane type tritepenic acid methyl ester was identiﬁed here for the ﬁrst time as a component of Eucalyptus bark tissues using GC–MS and NMR. Other high value triterpenic acids such as ursolic, oleanolic and betulinic acids, accounting for 1.3, 0.9 and 0.6 g kg−1, respectively, were also detected in this fraction. Finally, the extraction of methyl morolate with supercritical CO2 was also carried out aiming at designing an environmentally friendly extraction alternative for this abundant compound. At 20 MPa and 333 K, the methyl morolate extraction attained a plateau at 6 h. In the whole, the acetylated triterpenic acids were more signiﬁcantly extracted when compared to their free acids, which is directly related with the less polar nature of the former molecules.Industrial Crops and Products 02/2013; 43(1):340-348. · 3.21 Impact Factor
- Central-European Journal of Immunology 12/2013; 38(4):480-485. · 0.38 Impact Factor
- [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