Pinitol is a
cyclitol
In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is or where 3 ≤ ''x'' ≤ ''n''.
The name is also used for c ...
, a cyclic
polyol. It is a known
anti-diabetic
Drugs used in diabetes treat diabetes mellitus by altering the glucose level in the blood. With the exceptions of insulin, most GLP receptor agonists (liraglutide, exenatide, and others), and pramlintide, all are administered orally and are thu ...
agent isolated from ''
Sutherlandia frutescens
''Sutherlandia frutescens'' (cancer bush, balloon pea, sutherlandia, phetola ("it changes") in seTswana, and insiswa ("the one that drives away the darkness") in isiZulu; syn. ''Colutea frutescens'' L., ''Lessertia frutescens'' (L.) Goldblatt & ...
'' leaves.
Gall
Galls (from the Latin , 'oak-apple') or ''cecidia'' (from the Greek , anything gushing out) are a kind of swelling growth on the external tissues of plants, fungi, or animals. Plant galls are abnormal outgrowths of plant tissues, similar to be ...
plant tannins can be differentiated by their content of pinitol. It was first identified in the sugar pine (''
Pinus lambertiana''). It is also found in other plants, such as in the pods of the
carob tree.
Certain variants of the bacteria ''
Pseudomonas putida'' have been used in
organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
, the first example being the oxidation of
benzene, employed by
Steven Ley in the synthesis of (±)-pinitol.
Glycosides
Ciceritol is a pinitol
digalactoside
A galactoside is a glycoside containing galactose. The H of the OH group on carbon-1 of galactose is replaced by an organic moiety.
Depending on whether the glycosidic bond lies "above" or "below" the plane of the galactose molecule, galactosides ...
that can be isolated from seeds of
chickpea
The chickpea or chick pea (''Cicer arietinum'') is an annual legume of the family Fabaceae, subfamily Faboideae. Its different types are variously known as gram" or Bengal gram, garbanzo or garbanzo bean, or Egyptian pea. Chickpea seeds are high ...
,
lentil and
white lupin
''Lupinus albus'', commonly known as the white lupin or field lupine, is a member of the genus ''Lupinus'' in the family Fabaceae. It is a traditional pulse cultivated in the Mediterranean region.
Description
The white lupin is annual, more ...
.
A cyclitol derivative can be found in the marine sponge ''
Petrosia
''Petrosia'' is a genus of sponges belonging to the family Petrosiidae.
The genus has almost cosmopolitan distribution
In biogeography, cosmopolitan distribution is the term for the range of a taxon that extends across all or most of the wor ...
'' 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