The Chemistry of Plant LifeThatcher, Roscoe Wilfred
Science
The Chemistry of Plant Life
Thatcher, Roscoe Wilfred
Botanical chemistry
the fatty acid radicals may be attached either in one (1) position and one
(2) position, or in the two (1) positions; hence, two forms of
glycero-phosphoric acid are possible, thus
fatty acid fatty acid
/ /
(A) glycerol--fatty acid (B) glycerol--phosphoric acid
\ \
phosphoric acid fatty acid
Again, the choline may be attached to the phosphoric acid either through
its alcoholic (OH) group or through its basic (N) group, thus
OH OH
/ /
-P=O C_{2}H_{4} -P=O
\ / \ \
O N[trb](CH_{3})_{3} or, O-N[trb](CH_{3})_{3}
/ \
HO C_{2}H_{4}OH
The facts that in the arrangement (B) the central carbon atom of the
glycerol would be asymmetric, and that both lecithin and the
glycero-phosphoric acid derived from it by hydrolysis are optically active,
prove that formula (B) correctly represents the arrangement of that part of
the lecithin molecule; and there is ample theoretical and experimental
evidence to prove that the choline linkage is through the alcoholic (OH)
group. Hence the formula for lecithin indicating the linkage as shown above
is the correct one.
The fatty acids in the lecithin molecule may be different in lecithins from
different sources, just as they are different in fats from different
sources. Both oleic acid and a solid fatty acid have been found in the
hydrolysis products of lecithin from leguminous seeds. In certain lupine
seeds, the fatty acids present in the lecithin appear to be palmitic and
stearic.
OTHER PLANT PHOSPHATIDES
Phosphatides other than lecithin are common in plants. In these, various
sugars replace part or all of the glycerol as the alcoholic part of the
ester. Percentages of sugar varying from mere traces up to 17 per cent of
the weight of material taken, have been found in the products of hydrolysis
of phosphatides prepared from vetch seeds, potato tubers, plant pollens,
and whole wheat meal.
Furthermore, betaine
CH_{2}
/ \
(tri-methyl glycocoll, OC N[trb](CH_{3})_{3})
\ /
O
and perhaps other vegetable amines (see Chapter XII) sometimes replace
choline as the basic group in the phosphatides.
PLANT CEREBROSIDES
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