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Pinitol

Pinitol

D-(+)-chiro-Inositol D-Pinitol Inzitol D-(+)-Pinitol (+)-Pinitol Sennitol Pinnitol

Pinitol is a cyclitol, a cyclic polyol. 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). 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, the first example being the oxidation of benzene, employed by Steven Ley in the synthesis of (±)-pinitol.

Glycosides

Ciceritol is a pinitol digalactoside that can be isolated from seeds of chickpea, lentil 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.

Biosynthesis of D-Pinitol

References

References

  1. (1987). "Pinitol—A new anti-diabetic compound from the leaves of ''Bougainvillea spectabilis''". Current Science.
  2. . (2005-08-04). ["Introduction Sutherlandia frutesoens—Kankerbossie"](http://www.africanherbs.info/docs/Intro_Sutherlandia-kankerbossie.pdf).
  3. (2008). "Identification of the origin of commercial enological tannins by the analysis of monosaccharides and polyalcohols". Food Chemistry.
  4. (1952). "The structure of pinitol". Journal of the American Chemical Society.
  5. (March 2014). "Ultrasound-assisted extraction of D-pinitol from carob pods using Response Surface Methodology". Ultrasonics Sonochemistry.
  6. (1987). "Microbial oxidation in synthesis: A six step preparation of (±)-pinitol from benzene". Tetrahedron Letters.
  7. (1983). "Ciceritol, a pinitol digalactoside from seeds of chickpea, lentil and white lupin". Phytochemistry.
  8. (May 1999). "A cyclitol derivative as a replication inhibitor from the marine sponge Petrosia sp". Journal of Natural Products.
  9. (2021-02-01). "d-Pinitol: a cyclitol with versatile biological and pharmacological activities". Phytochemistry Reviews.
  10. (May 2019). "Water Deficit Elicits a Transcriptional Response of Genes Governing d-pinitol Biosynthesis in Soybean (''Glycine max'')". International Journal of Molecular Sciences.
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