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: 1.44). 02/2011; 91(5):789-96. DOI:10.1002/jsfa.4330 pp.789-96
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.

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    Article: Comparison of the triterpenoid content of berries and leaves of lingonberry Vaccinium vitis-idaea from Finland and Poland.
    Anna Szakiel, Cezary Pączkowski, Heini Koivuniemi, Satu Huttunen
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    ABSTRACT: Triterpenoid compounds extracted from fruits and leaves of lingonberry ( Vaccinium vitis-idaea L.) collected in Finland and Poland were identified and quantitated by GC-MS/FID. The main lingonberry triterpenoid profile consisted of α-amyrin, β-amyrin, betulin, campesterol, cycloartanol, erythrodiol, fern-7-en-3β-ol, friedelin, lupeol, sitosterol, stigmasterol, stigmasta-3,5-dien-7-one, swert-9(11)-en-3β-ol, taraxasterol, urs-12-en-29-al, uvaol, oleanolic acid, and ursolic acid. To our knowledge, this is the first thorough description of triterpenoid compounds in this species. Ursolic acid was identified as a principal triterpene in lingonberry fruit. The influence of geographical origin on the level of individual triterpenoid compounds was examined, and considerable variations in triterpenoid profile between berries and leaves obtained from the two locations were observed. The most striking difference concerned the occurrence of fernenol and taraxasterol, which were found to be the major triterpenol in lingonberry leaves of Finnish and Polish origin, respectively.
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    Anna Szakiel, Cezary Pączkowski, Satu Huttunen
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    ABSTRACT: Triterpenoid compounds found in free and ester forms in extracts of entire fruits and leaves, and in fruit and leaf cuticular waxes of bilberry (Vaccinium myrtillus L.) collected in Finland and Poland were identified and quantitated by GC-MS/FID. The main bilberry triterpenoid profile consisted of α- and β-amyrin, α- and β-amyrenone, campesterol, cholesterol, citrostadienol (in berries), cycloartanol, erythrodiol, lupeol, 24-methylenecycloartanol, sitosterol, sitostanol, stigmasterol, stigmasta-3,5-dien-7-one, uvaol, oleanolic and ursolic aldehydes, and oleanolic, ursolic, 2α-hydroxyoleanolic, and 2α-hydroxyursolic acids. Friedelin, and D:A-friedooleanan-3β-ol were found only in Finnish plants, whereas D:C-friedours-7-en-3β-ol, and taraxasterol were found only in Polish plants. To our knowledge, this is the first thorough description of triterpenoid compounds in this species. The presented results revealed that the triterpenoid profile of bilberry varied considerably between different organs of the plant regardless of the plant origin, as well as between plant samples obtained from the two geographical locations.
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Keywords

American cranberries
 
berry anticancer properties
 
cranberries
 
cranberry polyphenolics
 
DU145 prostate tumor cells
 
esters inhibited tumor cell growth
 
highest content
 
inhibit tumor cell proliferation
 
inhibited MMP-2
 
liquid chromatography-mass spectroscopy
 
macrocarpon berries
 
matrix metalloproteinase inhibition
 
MMP-9 activity
 
tumor cell lines
 
tumor invasion
 
ursolic acid
 
Ursolic acid content
 
Vaccinium macrocarpon
 
Vaccinium species
 
whole fruit
 

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