Pinitol is a
cyclitol, a cyclic
polyol
In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups (). The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, thr ...
. It is a known
anti-diabetic agent isolated from ''
Sutherlandia frutescens'' leaves.
Gall plant tannins can be differentiated by their content of pinitol. It was first identified in the sugar pine (''
Pinus lambertiana
''Pinus lambertiana'' (commonly known as the sugar pine or sugar cone pine) is the tallest and most massive pine tree, and has the longest cones of any conifer. The species name ''lambertiana'' was given by the Scottish botanist David Douglas, ...
''). It is also found in other plants, such as in the pods of the
carob tree.
Certain variants of the bacteria ''
Pseudomonas putida
''Pseudomonas putida'' is a Gram-negative, rod-shaped, saprotrophic soil bacterium.
Based on 16S rRNA analysis, ''P. putida'' was taxonomically confirmed to be a ''Pseudomonas'' species (''sensu stricto'') and placed, along with several other ...
'' have been used in
organic synthesis, the first example being the oxidation of
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...
, employed by
Steven Ley
Steven Victor Ley (born 10 December 1945) is Professor of Organic Chemistry in the Department of Chemistry at the University of Cambridge, and is a Fellow of Trinity College, Cambridge. He was President of the Royal Society of Chemistry (2000� ...
in the synthesis of (±)-pinitol.
Glycosides
Ciceritol
Ciceritol is a cyclitol. It is a pinitol digalactoside that can be isolated from seeds of chickpea, lentil
The lentil (''Lens culinaris'' or ''Lens esculenta'') is an edible legume. It is an annual plant known for its lens-shaped seeds ...
is a pinitol
digalactoside that can be isolated from seeds of
chickpea,
lentil
The lentil (''Lens culinaris'' or ''Lens esculenta'') is an edible legume. It is an annual plant known for its lens-shaped seeds. It is about tall, and the seeds grow in pods, usually with two seeds in each. As a food crop, the largest pro ...
and
white lupin.
A cyclitol derivative can be found in the marine sponge ''
Petrosia'' sp.
Biosynthesis
D-pinitol is the most widely distributed inositol ether in plants. In Angiosperms, D-pinitol has a relatively straight forward and short biosynthesis which proceeds via the Loewus pathway. The precursor to the biosynthesis pathway is glucose-6-phosphate, which is converted to D-ononitol (1-D-4-O-methyl-myo-inositol) via myo-inositol. Ononitol is epimerized to yield D-pinitol via a D-ononitol epimerase using NADPH as a cofactor.
References
{{reflist
External links
Pinitol on Sigma Aldrich website
Cyclitols