The Chemistry of Plant LifeThatcher, Roscoe Wilfred
Science
The Chemistry of Plant Life
Thatcher, Roscoe Wilfred
Botanical chemistry
Cumarin itself is widely distributed in plants. No glucoside containing
cumarin as such has yet been isolated; but several glucosides of its
oxy-derivatives are known. The following are common ones:
=Skimmin=, C_{15}H_{16}O_{8} (glucose and skimmetin), is found in _Skimmia
japonica_; =æsculin=, C_{15}H_{16}O_{9} (glucose and æsculetin), is found
in the bark of the horse-chestnut, _Æsculus hippocastanum_, and its isomer,
=daphnin= (glucose and daphnetin), in several species of _Daphne_; and
fraxin, C_{16}H_{18}O_{10} (glucose and fraxetin), is found in the bark of
several species of ash.
The structural arrangement of the oxy-cumarin groups which are found in
these glucosides is shown in the following formulas. It is not known to
which OH group the sugar is attached, in each case.
Skimmetin Æsculetin
CH=CH·CO CH=CH·CO
/\ | /\ |
/ \_O_| / \_O_|
| | | |
| | HO| |
\ / \ /
\/ \/
OH OH
Daphnetin Fraxetin
CH=CH·CO CH=CH·CO
/\ | /\ |
/ \_O_| / \_O_|
| | HO| |
| |OH HO| |
\ / \ /
\/ \/
OH OCH_{3}
=Scopolin=, C_{22}H_{28}O_{14}, found in _Scopolia japonica_, contains two
glucose molecules united to a monomethyl ether of æsculin; while
=limettin=, found in certain citrus trees, is the dimethyl ether of
æsculin.
THE PIGMENT GLUCOSIDES
Many, if not all, of the red, yellow, violet, and blue pigments of plants
either exist as, or are derived from, glucosides. These are of three types:
the madder, or alizarin, reds are derivatives of various
oxy-anthraquinones; most of the soluble yellow pigments are glucosides
derived from flavones or xanthones; and the soluble red, blue, and violet
pigments of the cell-sap of plants are mostly anthocyan derivatives. The
four basic groups, or nuclei, which are present in these different types of
compounds are complex groups consisting essentially of two benzene rings
linked together through a third ring in which there are either two oxygen
atoms in the ring, or one oxygen in the ring and a second attached to the
opposite carbon in the (C=O) arrangement, as shown by the following
diagrammatic formulas:
Xanthone Anthraquinone
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