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 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 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 ''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 The carob ( ; ''Ceratonia siliqua'') is a flowering evergreen tree or shrub in the Caesalpinioideae sub-family of the legume family, Fabaceae. It is widely cultivated for its edible fruit pods, and as an ornamental tree in gardens and lands ...

. 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 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 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 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 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 ''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'' 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