Pinitol

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
CAS Number	10284-63-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28548 ;
ChEMBL	ChEMBL493737 ;
ChemSpider	10369209 ;
PubChem CID	164619 (3Ξ,6Ξ);
UNII	TF9HZN9T0M ;
CompTox Dashboard (EPA)	DTXSID50883108 ;
	InChI 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 Key: DSCFFEYYQKSRSV-KLJZZCKASA-N ;
	SMILES CO[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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]

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]

References

^ 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.
^ "Introduction Sutherlandia frutesoens—Kankerbossie" (PDF). Afrikaanse Kruiden. 2005-08-04. Archived from the original (PDF) on 2006-09-14.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

External links

Pinitol on Sigma Aldrich website

[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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