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PHYTOCHEMICALS
MECHANISMS OF ACTION
Edited by
Mark S. Meskin
Wayne R. Bidlack
Audra J. Davies
Douglas S. Lewis
R. Keith Randolph
CRC PRESS
Boca Raton London New York Washington, D.C.
This edition published in the Taylor & Francis e-Library, 2005.
“To purchase your own copy of this or any of Taylor & Francis or Routledge’s
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ISBN 0-203-50633-2 Master e-book ISBN
ISBN 0-203-58762-6 (Adobe eReader Format)
CHAPTER
1
Absorption and Metabolism of
Anthocyanins: Potential Health Effects
Ronald L. Prior
CONTENTS
Abstract ..................................................................................................................... 1
Introduction .............................................................................................................. 2
Anthocyanins in Foods ............................................................................................. 3
Antioxidant and Other Biological Effects of Anthocyanins
In Vitro
...................... 5
Anthocyanins and a-Glucosidase Activity ..................................................... 7
Anthocyanin Absorption/Metabolism ...................................................................... 7
Gut Metabolism of Anthocyanins ................................................................... 9
In Vivo
Antioxidant and Other Effects of Anthocyanins — Animal Studies .......... 9
Antioxidant Effects ......................................................................................... 9
Vasoprotective Effects ................................................................................... 13
In Vivo
Antioxidant and Other Side Effects of Anthocyanins — Human Clinical
Studies .................................................................................................................... 13
Antioxidant Effects ....................................................................................... 13
Vascular Permeability ................................................................................... 15
Effects on Vision ........................................................................................... 15
Conclusions ............................................................................................................ 16
References .............................................................................................................. 16
ABSTRACT
This manuscript reviews literature on anthocyanins in foods and their metabolism
and absorption and possible relationships to human health. Of the various classes
of flavonoids, the potential dietary intake of anthocyanins is perhaps the greatest
0-8493-1672-3/04/$0.00+$1.50
© 2004 by CRC Press LLC
1
2
PHYTOCHEMICALS: MECHANISMS OF ACTION
(100+ mg/day). The content in fruits varies considerably between 0.25 to 700 mg/100
g fresh weight. Not only does the concentration vary, the individual specific antho-
cyanins present also are quite different in various fruits. Anthocyanins are absorbed
intact without cleavage of the sugar to form the aglycone. The proportion of the dose
that appears in the urine is quite small (<0.1%). Plasma levels of anthocyanins are
in the range of 1–120 nM following a meal high in anthocyanins, but fasting plasma
levels are generally nondetectable. Information is limited as to possible metabolites
of anthocyanins in the human. A number of antioxidant-related responses are reviewed
in animal models as well as in the human. Anthocyanins can provide protection
against various forms of oxidative stress in animal models, however, most of the
health-related responses have been observed at relatively high intakes of anthocya-
nins (2-400 mg/kg BW).
INTRODUCTION
Anthocyanins (Figure 1.1) are water soluble plant secondary metabolites responsible
for the blue, purple, and red color of many plant tissues. They occur primarily as
glycosides of their respective anthocyanidin-chromophores. The common anthocy-
anidin aglycones are cyanidin (cy), delphinidin (dp), petunidin (pt), peonidin (pn),
pelargonidin (pg), and malvidin (mv). The differences in chemical structure of these
six common anthocyanidins occur at the 3¢ and 5¢ positions (Figure 1.1). The
aglycones are rarely found in fresh plant material. There are several hundred known
anthocyanins. They vary in 1) the number and position of hydroxyl and methoxyl
groups on the basic anthocyanidin skeleton; 2) the identity, number and positions
at which sugars are attached; and 3) the extent of sugar acylation and the identity
of the acylating agent. Common acylating agents are the cinnamic acids (caffeic, r-
coumaric, ferulic, and sinapic). Acylated anthocyanins occur in some of the less
common foodstuffs such as red cabbage, red lettuce, garlic, red-skinned potato, and
purple sweet potato.
1
3'
R
1
4'
OH
+
O
B
HO
5'
7
A
R
2
5
3
OH
OH
R
1
R
2
Pelargonidin H H
Cyanidin OH H
Delphinidin OH OH
Peonidin OCH
3
H
Petunidin OCH
3
OH
Malvidin OCH
3
OCH
3
Figure 1.1
Common anthocyanin structures. Sugar moieties are generally on position 3 of
the C-ring.
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