Article

Cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside as primary phenolic antioxidants in black raspberry.

Department of Horticulture and Crop Science, The Ohio State University, Ohio Agricultural Research and Development Center, Wooster, OH 44691, USA.
Journal of Agricultural and Food Chemistry (impact factor: 2.82). 04/2008; 56(6):1880-8. DOI:10.1021/jf072313k pp.1880-8
Source: PubMed

ABSTRACT Anthocyanin constituents in black raspberries (Rubus occidentalis L.) were investigated by HPLC-DAD, and their involvement as potent, significant antioxidants in black raspberries was demonstrated by three common antioxidant assays (FRAP, DPPH, ABTS) in this study. Five anthocyanins were present in black raspberries: cyanidin 3-sambubioside, cyanidin 3-glucoside, cyanidin 3-xylosylrutinoside, cyanidin 3-rutinoside, and pelargonidin 3-rutinoside. Their identities and structures, with particular emphasis on cyanidin 3-xylosylrutinoside, were confirmed by NMR spectroscopy. Two of these anthocyanins, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside, predominated, comprising 24-40 and 49-58%, respectively, of the total anthocyanins in black raspberries. On the basis of both potency and concentration, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside were found to be the significant contributors to the antioxidant systems of black raspberries. These findings indicate that these two anthocyanin compounds may function as the primary phenolic antioxidants in black raspberries. These two compounds exhibit potential biological activities that may be exploited in conjunction with other naturally occurring bioactive compounds in black raspberry fruit-based products used in clinical trials for the treatment of various types of cancer.

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Keywords

Anthocyanin constituents
 
anthocyanins
 
antioxidant systems
 
black raspberries
 
black raspberry fruit-based products
 
clinical trials
 
common antioxidant assays
 
cyanidin 3-glucoside
 
cyanidin 3-rutinoside
 
cyanidin 3-xylosylrutinoside
 
occurring bioactive compounds
 
particular emphasis
 
pelargonidin 3-rutinoside
 
primary phenolic antioxidants
 
Rubus occidentalis L
 
significant antioxidants
 
total anthocyanins
 
two anthocyanin compounds
 
two compounds exhibit potential biological activities
 
various types