Pinitol Explained

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]

External links

Notes and References

  1. Narayanan CR, Joshi DD, Mujumdar AM, Dhekne VV . 1987 . Pinitol—A new anti-diabetic compound from the leaves of Bougainvillea spectabilis . Current Science . 56 . 3 . 139–141 . 24091051 . free.
  2. Web site: Introduction Sutherlandia frutesoens—Kankerbossie . . 2005-08-04 . Afrikaanse Kruiden . https://web.archive.org/web/20060914123611/http://www.africanherbs.info/docs/Intro_Sutherlandia-kankerbossie.pdf . 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 . 10.1016/j.foodchem.2008.04.050 . 84922451.
  4. Anderson AB, MacDonald DL, Fischer HO . 1952 . The structure of pinitol . Journal of the American Chemical Society . 74 . 6 . 1479–1480 . 10.1021/ja01126a036 . 101698212.
  5. Tetik N, Yüksel E . Ultrasound-assisted extraction of D-pinitol from carob pods using Response Surface Methodology . Ultrasonics Sonochemistry . 21 . 2 . 860–865 . March 2014 . 24090831 . 10.1016/j.ultsonch.2013.09.008 . free . 28123933 . free .
  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 . 10.1016/S0040-4039(00)95692-2 . 83944164.
  7. Quemener B, Brillouet JM . 1983 . Ciceritol, a pinitol digalactoside from seeds of chickpea, lentil and white lupin . Phytochemistry . 22 . 8 . 1745–1751 . 10.1016/S0031-9422(00)80263-0 . 84765529.
  8. Kim DK, Lim YJ, Kim JS, Park JH, Kim ND, Im KS, Hong J, Jung JH . 6 . A cyclitol derivative as a replication inhibitor from the marine sponge Petrosia sp . Journal of Natural Products . 62 . 5 . 773–776 . May 1999 . 10346968 . 10.1021/np9804785 . 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 . en . 20 . 1 . 211–224 . 10.1007/s11101-020-09677-6 . 1572-980X.
  10. Dumschott K, Dechorgnat J, Merchant A . Water Deficit Elicits a Transcriptional Response of Genes Governing d-pinitol Biosynthesis in Soybean (Glycine max) . International Journal of Molecular Sciences . 20 . 10 . 2411 . May 2019 . 31096655 . 6566849 . 10.3390/ijms20102411 . free .

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