The Chemistry of Plant LifeThatcher, Roscoe Wilfred
Science
The Chemistry of Plant Life
Thatcher, Roscoe Wilfred
Botanical chemistry
-----O------
| |
CH_{2}OH·CHOH·CH·CHOH·CH·CH
| |
O S
| /
|/
C=N[trb]C_{3}H_{5}
This compound usually breaks down into glucose and mustard oil; but by
special treatment it is possible to obtain from it thioglucose,
C_{6}H_{11}O_{5}·SH. This indicates that in the original glucoside the
glucose is linked with the mustard oil through the sulfur atom.
=Sinalbin=, C_{30}H_{42}O_{15}N_{2}S_{2}, from white mustard seeds, when
hydrolyzed by myrosin, yields glucose, sinalbin mustard oil (a
paraoxybenzyl derivative of allyl isosulfocyanide) and sinapin acid
sulfate; according to the equation
C_{30}H_{42}O_{15}N_{2}S_{2}+H_{2}O = C_{6}H_{12}O_{6}+C_{7}H_{7}O·NCS
Sinalbin Glucose Sinalbin mustard oil
+ C_{16}H_{24}O_{5}N·HSO_{4}.
Sinapin acid sulfate
The sinalbin mustard oil may be represented by the formula
____
/ \
HO-CH CH-CH_{2}NCS. Hydrolysis of the sinapin acid sulfate converts
\____/
it into sinapinic acid, C_{6}H_{2}OH·(OCH_{3})_{2}·CH=CH·COOH, choline,
N(CH_{3})_{4}C_{2}H_{4}OH (see page 152), and H_{2}SO_{4}. It is,
therefore, a very complex glucoside.
TEE DIGITALIS GLUCOSIDES
The five, or more, glucosides which are present in the leaves and seeds of
the foxglove (_Digitalis purpurea_) have been extensively studied, as they
are the active principles in the various digitalis extracts which are used
in medicine as a heart stimulant.
=Digitoxin=, C_{34}H_{54}O_{11}, which is the most active of these
glucosides in its physiological effects, when hydrolyzed, yields
digitoxigenin, C_{22}H_{32}O_{4}, and a sugar having the formula
C_{6}H_{12}O_{4}, which is known as "digitoxose" and is supposed to be a
dimethyl tetrose.
=Digitalin=, C_{35}H_{56}O_{14}, is also strongly active. When hydrolyzed,
it yields digitaligenin, C_{22}H_{10}O_{3}, glucose, and digitoxose.
=Digitonin=, C_{54}H_{92}O_{28}, constitutes about one-half of the total
glucosides in the extract which is obtained from most species of the
digitalis plants. It is much less active than the others. It is a saponin
(see page 90) in type. On hydrolysis, it yields 2 molecules of glucose, 2
of galactose, and one of digitogenin.
=Gitonin=, C_{49}H_{80}O_{23}, containing 3 molecules of galactose, one of
a pentose sugar, and one of gitogenin; and =gitalin=, C_{28}H_{48}O_{10},
containing digitoxose and gitaligenin, have also been isolated from
digitalis extracts.
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