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From: "Steve Harris" <>
Subject: Re: Has cranberry juice helped anyone?
Date: Sat, 6 Apr 2002 16:44:10 -0700
Message-ID: <a8o18o$2ru$>

<> wrote in message
> Anthocyanosides
> one of the main kinds of ingredients in cranberries (bilberries,
> blueberries, etc.), that are thought to be helpful, are the
> anthocyanosides.
> i read somewhere, that these are condensed tannins.
> --------------
> Spelling?
> so many long words are misspelled, as i am trying to read more about
> this!
> would someone please clarify which spellings are correct?
> anthocyanidins, anthrocyanidins ?
> proanthocyanidins, proanthrocyanidins ?


There is no "r"-- it's always antho not anthro. Anthro means "human"
(anthropology), whereas the chemicals we're talking about are named for
being flower pigments. Though they are not ALL flower pigments, so you also
occasionally see them called "procyanidins" or even "cyanidins."

There are no "proanthocyanins" either (you didn't list these, but somebody
might think of it). The anthocyanIDINs ARE, in a sense, the
"pro"anthocyanINs (and also much more), so that's the name that is used
instead. The "pro" refers to the compounds that are the parents.

I'll get you started. These things are all quasi "phenols" (OH attached to
an aromatic ring) and that gives them all an antioxidant capability a bit
like that of vitamin E. Electrons and sacrificed to some rapacious molecule
that wants them, and the quinone form is generated in the phenol. Some of
them also chelate iron, and thus inhibit iron's Fenton antioxidant type
reactions. They aren't, in general, spin-traps.

The condensed "tannin" like forms that you see in bark and grapeseeds are
the pro-anthocyanidins, or procyanidins, which are POLY-phenols. The phenols
are repeated in chains. These are uncolored and often water soluble.
Apparently they can't be absorbed by the gut without being broken up into at
least small multimers.  Grapeseed extract and pine bark extracts
("Pycnogenol") are two commonly encountered commercial forms.

The anthocyanidins (this name with the antho is usually used as the class
because there is an explicit "cyanidin" compound) are the monomers, and
these are sometimes colored and sometimes not. When they are explicitly
colored and are being used by the plant as a fruit or flower pigment (always
red, blue, or purple), then the "cyanin" ending is used (cyan is Greek for
blue, but as noted these things are also red, and this can vary even with
pH, as in blueberries vs. the more acidic cranberries, which are both
colored with delphinidin). Again, "anthocyanin" is usually used for the
class, because there is a particular compound called cyanin. The pigments
are usually much more heavily conjugated with sugars, which assists the dye
function (don't ask). The ending "inidin" also identifies a characteristic
inner ring structure, and is more of a chemical name, whereas the mere
"idin" is more functional, and refers to a dye.  "Anthocyanosides" refers
explicitly to these same anthocyanidin compounds (the suffix "-oside"
referring to the sugar moiety add-ons).

Some of the anthocyanidin or anthocyanin names reveal flower origins like
delphinidin or petunidin.  Also you'll see the specific base compounds
cyanidin (red beans), pelargonidin (strawberries) and malvidin (grapes).
Most red or blue colored fruits have several of these pigments, and
delphinidin and cyanidin are actually probably the most common dietary

Which of these things is good for you?  I can't say for sure. Probably most
of them, in some mild sense. They all have anticancer properties in various
systems, but so what else is new; most antioxidants do. Mild antioxidants
probably also keep your arteries clean. The question of what does what in
vivo is still being answered. Strawberries and blueberries look good in
rodents <g>.  It is known that the body can and does absorb the entire
sugared forms intact, and excrete them that way, much like other classes of
flavonoids. That's kind of funny, and suggests the human body has some use
for them all, though perhaps does not absolutely require any of them up to
"vitamin" standards.


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