1D-chiro-Inositol

{{DISPLAYTITLE:1D-chiro-Inositol}} 443555991 1D-chiro-Inositol Merck Index, 11th Edition, 4883 D-chiro-inositol.png 125px D-chiro-Inositol 1D-chiro-Inositol (1R,2R,3S,4S,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexol DCI cis-1,2,4-trans-3,5,6-Cyclohexanehexol 1D-1,2,4/3,5,6-Cyclohexanehexol 1,2,4/3,5,6-Hexahydroxycyclohexane (+)-inositol 4645 correct ?? 643-12-9 correct FDA 6R79WV4R10 correct chemspider 10254647 correct EBI 27372 O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O correct chemspider 1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5+,6+/m0/s1 correct chemspider CDAISMWEOUEBRE-LKPKBOIGSA-N 6 12 6 [α]23/D +55°, c = 1.2 in H2O 230 1D-chiro-Inositol or D-chiro-inositol (often abbreviated DCI) is a chemical substance with formula C6H12O6, one of the nine isomers of cyclohexane-1,2,3,4,5,6-hexol (which may be collectively called "inositol"). The molecule has a ring of six carbon atoms, each bound to one hydrogen atom and one hydroxyl (OH) group. The hydroxyls on atoms 1, 2, and 4, in counterclockwise order, lie above the plane of the ring. The molecule being distinct from its mirror image, the compound is chiral, hence its name. Its enantiomer (mirror compound) is 1L-chiro-inositol. Compared to its more common isomer myo-inositol, DCI seems to have relatively minor roles in biochemistry and medicine, mostly connected to the biochemistry of insulin and other hormones. Biochemistry and physiology Occurrence The common isomer myo-inositol is converted into DCI in the human body by an insulin dependent enzyme, NAD/NADH epimerase. Insulin interactions D-chiro-inositol is known to be an important secondary messenger in insulin signal transduction. It accelerates the dephosphorylation of glycogen synthase and pyruvate dehydrogenase, rate limiting enzymes of non-oxidative and oxidative glucose disposal. Exogenous DCI may act to bypass defective normal epimerization of myo-inositol to DCI associated with insulin resistance and at least partially restore insulin sensitivity and glucose disposal. In clinical practice, it improves insulin signaling, thus restoring physiological insulin levels in resistant subjects. Hormonal treatment D-chiro-inositol has been used to induce ovulation in women with polycystic ovary syndrome. DCI depresses the expression of the steroidogenic enzyme aromatase, which is responsible for the conversion of androgens to estrogens. One pilot study found males taking DCI had increased androgens and reduced estrogen. References 104.2.1 Monastra G, Vazquez-Levin M, Bezerra Espinola MS, Bilotta G, Laganà AS, Unfer V D-chiro-inositol, an aromatase down-modulator, increases androgens and reduces estrogens in male volunteers: a pilot study Basic and Clinical Andrology 31 1 13 June 2021 34078260 8173878 10.1186/s12610-021-00131-x free R. Gamboli, G. Forte, C. Aragona, A. Bevilacqua, M. Bizzarri, V. Unfer (2021): "The use of D-chiro-inositol in clinical practice". European Review for Medical and Pharmacological Sciences, volume 25, issue 1, pages 438-446. 10.26355/eurrev_202101_24412 Larner Joseph 2002 D-chiro-inositol—its functional role in insulin action and its deficit in insulin resistance International Journal of Experimental Diabetes Research 3 1 47–60 10.1080/15604280212528 1560-4284 2478565 11900279 Heimark Douglas McAllister Jan Larner Joseph 2014 Decreased myo-inositol to chiro-inositol (M/C) ratios and increased M/C epimerase activity in PCOS theca cells demonstrate increased insulin sensitivity compared to controls Endocrine Journal 61 2 111–117 10.1507/endocrj.ej13-0423 1348-4540 24189751 free Bizzarri M. Carlomagno G. July 2014 Inositol: history of an effective therapy for Polycystic Ovary Syndrome European Review for Medical and Pharmacological Sciences 18 13 1896–1903 2284-0729 25010620 Kalra Bharti Kalra Sanjay Sharma J. B. 2016 The inositols and polycystic ovary syndrome Indian Journal of Endocrinology and Metabolism 20 5 720–724 10.4103/2230-8210.189231 2230-8210 5040057 27730087 free Nestler John E. Unfer Vittorio July 2015 Reflections on inositol(s) for PCOS therapy: steps toward success Gynecological Endocrinology 31 7 501–505 10.3109/09513590.2015.1054802 1473-0766 26177098 207490049 Sortino Maria A. Salomone Salvatore Carruba Michele O. Drago Filippo 2017-06-08 Polycystic Ovary Syndrome: Insights into the Therapeutic Approach with Inositols Frontiers in Pharmacology 8 341 10.3389/fphar.2017.00341 1663-9812 5463048 28642705 free Category:Inositol