US EPA

1133328 

Journal Article 

Antimicrobial constituents of Thompson seedless raisins (Vitis vinifera) against selected oral pathogens 

Rivero-Cruz, JF; Zhu, M; Kinghorn, AD; Wu, CD 

2008 

0 

Phytochemistry Letters
ISSN: 1874-3900
EISSN: 1876-7486 

ELSEVIER SCIENCE BV 

AMSTERDAM 

1 

3 

151-154 

English 

10.1016/j.phytol.2008.07.007 

WOS:000263033900006 

As a part of a project directed toward the discovery of oral antimicrobial compounds from plants, eight known compounds, oleanolic acid (1), oleanolic aldehyde (2), linoleic acid (3), linolenic acid (4), betulin (5), betulinic acid (6), 5-(hydroxymethyl)-2-furfural (7), and β-sitosterol were isolated from an hexane-soluble partition of a methanol extract of Thompson seedless raisins (Vitis vinifera). From an EtOAc-soluble partition rutin (8) and β-sitosterol glycoside were isolated. In an attempt to increase the resultant antimicrobial activity of oleanolic acid (1), a series of acylation and etherification reactions were performed on oleanolic acid to obtain derivatives 1a-1f. All the compounds isolated and the derivatives 1a-1f were evaluated for their antimicrobial activity against two oral pathogens, Streptococcus mutans and Porphyromonas gingivalis associated with caries and periodontal disease, respectively. Compounds 1, 2, 7 and 1f inhibited the growth of the test bacteria with concentrations ranging from 3.9 to 500 μg/mL. Derivative 1f showed greatly enhanced antimicrobial activity when compared with oleanolic acid (1). 

Thompson seedless raisins; "Vitis vinifera"; Triterpenes; Oleanolic acid; 5-(Hydroxymethyl)-furfural; Oleanolic acid sodium salt; Natural oral antimicrobials; Oral pathogens