Pinitol

Pinitol
Chemical structure of pinitol
Chemical structure of D-pinitol
Names
IUPAC name
1D-chiro-Inositol
Systematic IUPAC name
(1R,2S,3R,4S,5S,6S)-6-Methoxycyclohexane-1,2,3,4,5-pentol
Other names
3-O-Methyl-D-chiro-inositol
D-(+)-chiro-Inositol
D-Pinitol
Inzitol
D-(+)-Pinitol
(+)-Pinitol
Sennitol
Pinnitol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5-,6+,7+/m0/s1 checkY
    Key: DSCFFEYYQKSRSV-KLJZZCKASA-N checkY
  • CO[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O
Properties
C7H14O6
Molar mass 194.183 g·mol−1
Melting point 179 to 185 °C (354 to 365 °F; 452 to 458 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
Biosynthesis of D-Pinitol

References

  1. ↑ Narayanan CR, Joshi DD, Mujumdar AM, Dhekne VV (1987). "Pinitol—A new anti-diabetic compound from the leaves of Bougainvillea spectabilis" (PDF). Current Science. 56 (3): 139–141. JSTOR 24091051.
  2. ↑ "Introduction Sutherlandia frutesoens—Kankerbossie" (PDF). Afrikaanse Kruiden. 2005-08-04. Archived from the original (PDF) on 2006-09-14.
  3. ↑ Sanz ML, Martínez-Castro I, Moreno-Arribas MV (2008). "Identification of the origin of commercial enological tannins by the analysis of monosaccharides and polyalcohols". Food Chemistry. 111 (3): 778–783. doi:10.1016/j.foodchem.2008.04.050. S2CID 84922451.
  4. ↑ Anderson AB, MacDonald DL, Fischer HO (1952). "The structure of pinitol". Journal of the American Chemical Society. 74 (6): 1479–1480. Bibcode:1952JAChS..74.1479A. doi:10.1021/ja01126a036. S2CID 101698212.
  5. ↑ Tetik N, Yüksel E (March 2014). "Ultrasound-assisted extraction of D-pinitol from carob pods using Response Surface Methodology". Ultrasonics Sonochemistry. 21 (2): 860–865. Bibcode:2014UltS...21..860T. doi:10.1016/j.ultsonch.2013.09.008. PMID 24090831. S2CID 28123933.
  6. ↑ Ley SV, Sternfeld F, Taylor S (1987). "Microbial oxidation in synthesis: A six step preparation of (±)-pinitol from benzene". Tetrahedron Letters. 28 (2): 225–226. doi:10.1016/S0040-4039(00)95692-2. S2CID 83944164.
  7. ↑ Quemener B, Brillouet JM (1983). "Ciceritol, a pinitol digalactoside from seeds of chickpea, lentil and white lupin". Phytochemistry. 22 (8): 1745–1751. Bibcode:1983PChem..22.1745Q. doi:10.1016/S0031-9422(00)80263-0. S2CID 84765529.
  8. ↑ Kim DK, Lim YJ, Kim JS, Park JH, Kim ND, Im KS, et al. (May 1999). "A cyclitol derivative as a replication inhibitor from the marine sponge Petrosia sp". Journal of Natural Products. 62 (5): 773–776. Bibcode:1999JNAtP..62..773K. doi:10.1021/np9804785. PMID 10346968. S2CID 20297208.
  9. ↑ Sánchez-Hidalgo M, León-González AJ, Gálvez-Peralta M, González-Mauraza NH, Martin-Cordero C (2021-02-01). "d-Pinitol: a cyclitol with versatile biological and pharmacological activities". Phytochemistry Reviews. 20 (1): 211–224. Bibcode:2021PChRv..20..211S. doi:10.1007/s11101-020-09677-6. ISSN 1572-980X.
  10. ↑ Dumschott K, Dechorgnat J, Merchant A (May 2019). "Water Deficit Elicits a Transcriptional Response of Genes Governing d-pinitol Biosynthesis in Soybean (Glycine max)". International Journal of Molecular Sciences. 20 (10): 2411. doi:10.3390/ijms20102411. PMC 6566849. PMID 31096655.