The Chemistry of Plant LifeThatcher, Roscoe Wilfred
Science
The Chemistry of Plant Life
Thatcher, Roscoe Wilfred
Botanical chemistry
=Quercitrin=, C_{21}H_{20}O_{11}, is found in oak bark, in the leaves of
horse-chestnut, and in many other plants, often associated with other
pigments. It is a brilliant yellow crystalline powder. Industrially, it
ranks next to indigo and alizarin in importance as a natural dye stuff. It
is a glucoside of rhamnose with 1,3,3',4', tetraoxyflavonol (i.e., the
flavone nucleus with five OH groups replacing the hydrogens in the 1, 3, 5,
3', and 4' positions). =Quercetin=, C_{15}H_{10}O_{7}, which is the
tetraoxyflavonol itself, without any sugar in combination with it, is found
in the leaves of several species of tropical plants and in the bark of
others. =Isoquercitrin=, C_{21}H_{20}O_{12}, is derived from the same
flavone, but contains glucose instead of rhamnose, as the sugar constituent
of the glucoside.
=Apiin=, C_{26}H_{20}O_{9}, the yellow glucoside found in the leaves of
parsley, celery, etc., contains apiose (a pentose sugar of very unusual
structure, represented by the formula,
CH_{2}OH
\
COH·CHOH·CHO), and apigenin, which is a 1,3,4',trioxyflavone.
/
CH_{2}OH
=Xanthorhamnin=, C_{34}H_{42}O_{20}, is a very complex glucoside containing
two rhamnose and one galactose groups, united with rhamnetin, which is
quercitin with the H of the OH in either the 1, or 3, position replaced by
a methyl group. There are several similar pigments which differ from
xanthorhamnin only in the number or position of the methoxy groups (i.e.,
the OH groups with a CH_{3} replacing the H), or in the nature of the sugar
which is present in the compound. Rhamnetin itself is found in the fruits
of certain species of _Rhamnus_, and is used in dyeing cotton.
The structural arrangement of the characteristic groups of these flavone
pigments will be dealt with more in detail in the chapter dealing with
Pigments (Chapter VIII).
The best-known yellow pigment which is a _xanthone_ derivative is
=euxanthic acid=, known as "Indian yellow," which is a "paired" compound of
glucuronic acid (see page 42) and euxanthone. The latter is a 2, 3',
dioxyxanthone. The pigment is found in the urine of cattle which have been
fed on mango leaves.
The soluble red, blue, and violet pigments are glucosides of various
hydroxy-derivatives of the anthocyan nucleus. Their constitution and
properties will be discussed in detail in the chapter dealing with the
Pigments. These compounds are isomeric with similar flavone and xanthone
derivatives, and the transition from one color to the other in plants takes
place very easily under the action of oxidizing or reducing enzymes. This
accounts for the change of reds and blues to yellows and browns, and vice
versa, under changing temperature conditions.
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