Pinitol

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Pinitol
Chemical structure of D-pinitol D-Pinitol.svg
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
PubChem CID
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 Yes check.svgY
    Key: DSCFFEYYQKSRSV-KLJZZCKASA-N Yes check.svgY
  • 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. [1] [2] Gall plant tannins can be differentiated by their content of pinitol. [3] It was first identified in the sugar pine ( Pinus lambertiana ). [4] It is also found in other plants, such as in the pods of the carob tree. [5]

Contents

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. [6]

Glycosides

Ciceritol is a pinitol digalactoside that can be isolated from seeds of chickpea, lentil and white lupin. [7]

A cyclitol derivative can be found in the marine sponge Petrosia sp. [8]

Biosynthesis

D-pinitol is the most widely distributed inositol ether in plants. [9] 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. [10]

Biosynthesis of D-Pinitol Pinitol biosynthesis.svg
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. 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. 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. 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. 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. 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.
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