Coumaroyl Iridoids and a Depside from Cranberry (Vaccinium macrocarpon)

• Published in: Journal of natural products (Washington, D.C.) Vol. 70; no. 2; pp. 253 - 258
• Main Authors: Turner, Allison, Chen, Shao-Nong, Nikolic, Dejan, van Breemen, Richard, Farnsworth, Norman R, Pauli, Guido F
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.02.2007; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: 10-p-cis-coumaroyl-1S-dihydromonotropein; 10-p-trans-coumaroyl-1S-dihydromonotropein; 2-O-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxyphenylmethylacetate; Biological and medical sciences; Chemistry, Medicinal; cranberries; Depsides - chemistry; Depsides - isolation & purification; Depsides - pharmacology; Escherichia coli - drug effects; Escherichia coli - pathogenicity; Food industries; fruit juices; Fundamental and applied biological sciences. Psychology; General pharmacology; human health; Humans; Iridoid Glycosides; Iridoids - chemistry; Iridoids - isolation & purification; Iridoids - pharmacology; Life Sciences & Biomedicine; Medical sciences; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; phytochemicals; Plant Sciences; Plants, Medicinal - chemistry; Research and development. New food products, dietetic foods and beverages; Science & Technology; Stereoisomerism; Vaccinium macrocarpon; Vaccinium macrocarpon - chemistry; CONDENSED TANNINS; B2 EPICATECHIN-(4-BETA-8)-EPICATECHIN; METABOLISM; INHIBIT ADHERENCE; PROCYANIDINS; FIMBRIATED ESCHERICHIA-COLI; JUICE; ABSORPTION; URINARY; BACTERIURIA; Iridoid; Urine; Terpenoid; Urinary system disease; Depside; Marker; Oligomer; Adhesion; Fruit juice; Biological activity; Vaccinium macrocarpon; Urinary tract infection; Polyphenol; Dicotyledones; Angiospermae; Isolation; Monoterpene; Spermatophyta; Glycoside; Ericaceae; Beverage; Mechanism of action; Structural analysis; Food supplement
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np060260f

Cranberry (Vaccinium macrocarpon) juice has been used for urinary tract infections for approximately 50 years. Recent research suggests that this botanical blocks adherence of pathogenic E. coli to urinary tract cells, thus preventing infection. While current evidence indicates that proanthocyanidins are responsible for this activity, these compounds may not reach the urinary tract; thus further investigation is warranted. Fractionation of cranberry juice concentrate was guided by a recently published antiadherence assay, and the resulting fractions were phytochemically characterized. Two new coumaroyl iridoid glycosides, 10-p-trans- (1) and 10-p-cis-coumaroyl-1S-dihydromonotropein (2), and a depside, 2-O-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxyphenylmethylacetate (3), were isolated, and although these compounds did not have antiadherent activity in isolation, they might constitute a new group of marker compounds for this active fraction of cranberry.