Literature DB >> 21351105

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

Miwako Kondo1, Shawna L MacKinnon, Cheryl C Craft, Michael D Matchett, Robert A R Hurta, Catherine C Neto.   

Abstract

BACKGROUND: 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.
RESULTS: 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.
CONCLUSION: 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.
Copyright © 2011 Society of Chemical Industry.

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Year:  2011        PMID: 21351105     DOI: 10.1002/jsfa.4330

Source DB:  PubMed          Journal:  J Sci Food Agric        ISSN: 0022-5142            Impact factor:   3.638


  15 in total

1.  Ursolic acid protects diabetic mice against monocyte dysfunction and accelerated atherosclerosis.

Authors:  Sarah L Ullevig; Qingwei Zhao; Debora Zamora; Reto Asmis
Journal:  Atherosclerosis       Date:  2011-06-17       Impact factor: 5.162

2.  The first genetic map of the American cranberry: exploration of synteny conservation and quantitative trait loci.

Authors:  Laura Georgi; Jennifer Johnson-Cicalese; Josh Honig; Sushma Parankush Das; Veeran D Rajah; Debashish Bhattacharya; Nahla Bassil; Lisa J Rowland; James Polashock; Nicholi Vorsa
Journal:  Theor Appl Genet       Date:  2012-12-08       Impact factor: 5.699

Review 3.  Lead Phytochemicals for Anticancer Drug Development.

Authors:  Sukhdev Singh; Bhupender Sharma; Shamsher S Kanwar; Ashok Kumar
Journal:  Front Plant Sci       Date:  2016-11-08       Impact factor: 5.753

Review 4.  Fruit-Derived Polysaccharides and Terpenoids: Recent Update on the Gastroprotective Effects and Mechanisms.

Authors:  Mohammed Safwan Ali Khan; Syeda Umme Kulsoom Khundmiri; Syeda Rukhaiya Khundmiri; Mohammad M Al-Sanea; Pooi Ling Mok
Journal:  Front Pharmacol       Date:  2018-06-22       Impact factor: 5.810

5.  Enhanced Antioxidant Activity of Ursolic Acid by Complexation with Copper (II): Experimental and Theoretical Study.

Authors:  Mariola Samsonowicz; Monika Kalinowska; Kamila Gryko
Journal:  Materials (Basel)       Date:  2021-01-07       Impact factor: 3.623

6.  Proanthocyanidin-enriched cranberry extract induces resilient bacterial community dynamics in a gnotobiotic mouse model.

Authors:  Catherine C Neto; Benedikt M Mortzfeld; John R Turbitt; Shakti K Bhattarai; Vladimir Yeliseyev; Nicholas DiBenedetto; Lynn Bry; Vanni Bucci
Journal:  Microb Cell       Date:  2021-04-29

7.  Fruit cuticular waxes as a source of biologically active triterpenoids.

Authors:  Anna Szakiel; Cezary Pączkowski; Flora Pensec; Christophe Bertsch
Journal:  Phytochem Rev       Date:  2012-06-26       Impact factor: 5.374

Review 8.  Cranberries and their bioactive constituents in human health.

Authors:  Jeffrey B Blumberg; Terri A Camesano; Aedin Cassidy; Penny Kris-Etherton; Amy Howell; Claudine Manach; Luisa M Ostertag; Helmut Sies; Ann Skulas-Ray; Joseph A Vita
Journal:  Adv Nutr       Date:  2013-11-06       Impact factor: 8.701

Review 9.  Cranberries and Cancer: An Update of Preclinical Studies Evaluating the Cancer Inhibitory Potential of Cranberry and Cranberry Derived Constituents.

Authors:  Katherine M Weh; Jennifer Clarke; Laura A Kresty
Journal:  Antioxidants (Basel)       Date:  2016-08-18

10.  Variation of ursolic acid content in flowers of ten Iranian pomegranate (Punica granatum L.) cultivars.

Authors:  Fatemeh Sharifiyan; Seyed Abbas Mirjalili; Mohammad Fazilati; Elahe Poorazizi; Saeed Habibollahi
Journal:  BMC Chem       Date:  2019-07-03
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