{{DISPLAYTITLE:1<small>D</small>-''chiro''-Inositol}} {{chembox | verifiedrevid = 443555991 | Name = 1<small>D</small>-''chiro''-Inositol | Reference =<ref>''[[Merck Index]]'', 11th Edition, '''4883'''</ref> | ImageFile = D-chiro-inositol.png | ImageSize = 125px | ImageName = <small>D</small>-''chiro''-Inositol | IUPACName = 1<small>D</small>-''chiro''-Inositol<ref name=bb/> | SystematicName = (1''R'',2''R'',3''S'',4''S'',5''S'',6''S'')-Cyclohexane-1,2,3,4,5,6-hexol | OtherNames = DCI <br /> ''cis''-1,2,4-''trans''-3,5,6<wbr />-Cyclohexanehexol <br /> 1<small>D</small>-1,2,4/3,5,6-Cyclohexanehexol<ref name="bb" /> <br /> 1,2,4/3,5,6-Hexahydroxycyclohexane <br /> (+)-inositol<ref name="bb" /> | Section1 = {{Chembox Identifiers | IUPHAR_ligand = 4645 | CASNo_Ref = {{cascite|correct|??}} | CASNo = 643-12-9 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 6R79WV4R10 | PubChem = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 10254647 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 27372 | SMILES = O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI=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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = CDAISMWEOUEBRE-LKPKBOIGSA-N }} | Section2 = {{Chembox Properties | C=6|H=12|O=6 | SpecRotation = [α]23/D +55°, c = 1.2 in H<sub>2</sub>O | MeltingPtC = 230 }} }}
'''1<small>D</small>-''chiro''-Inositol'''<ref name=bb/> or '''<small>D</small>-''chiro''-inositol'''<ref name=arag2021/> (often abbreviated '''DCI''') is a [[chemical substance]] with formula {{chem2|C6H12O6}}, one of the nine [[isomer]]s 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 [[chirality (chemistry)|chiral]], hence its name. Its [[enantiomer]] (mirror compound) is [[1L-chiro-inositol|1<small>L</small>-''chiro''-inositol]].
Compared to its more common isomer [[inositol|''myo''-inositol]], DCI seems to have relatively minor roles in [[biochemistry]] and medicine, mostly connected to the biochemistry of [[insulin]] and other [[hormone]]s.<ref name=larn2002/><ref name=vasq2021/>
==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]].<ref name=sort2017/><ref name=kalr2016/><ref name=nest2015/><ref name=bizz2014/><ref name=heim2014/>
===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.<ref name=larn2002/> In clinical practice, it improves insulin signaling, thus restoring physiological insulin levels in resistant subjects.<ref name=arag2021/>
===Hormonal treatment===
D-''chiro''-inositol has been used to induce ovulation in women with polycystic ovary syndrome.<ref name=arag2021/>
DCI depresses the expression of the [[steroidogenic enzyme]] [[aromatase]], which is responsible for the conversion of [[androgens]] to [[estrogens]].<ref name=arag2021/> One pilot study found males taking DCI had increased androgens and reduced estrogen.<ref name=vasq2021/>
== References == <references>
<ref name=bb>{{BlueBook2013|rec=104.2.1}}</ref>
<ref name=vasq2021>{{cite journal |vauthors=Monastra G, Vazquez-Levin M, Bezerra Espinola MS, Bilotta G, Laganà AS, Unfer V |title=D-chiro-inositol, an aromatase down-modulator, increases androgens and reduces estrogens in male volunteers: a pilot study |journal=[[Basic and Clinical Andrology]] |volume=31 |issue=1 |article-number=13 |date=June 2021 |pmid=34078260 |pmc=8173878 |doi=10.1186/s12610-021-00131-x |url= |issn= |doi-access=free }}</ref>
<ref name=arag2021>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. {{doi|10.26355/eurrev_202101_24412}}</ref>
<ref name=larn2002>{{Cite journal|last=Larner|first=Joseph|date=2002|title=D-''chiro''-inositol—its functional role in insulin action and its deficit in insulin resistance|journal=International Journal of Experimental Diabetes Research|volume=3|issue=1|pages=47–60|doi=10.1080/15604280212528|issn=1560-4284|pmc=2478565|pmid=11900279}}</ref>
<ref name=heim2014>{{Cite journal|last1=Heimark|first1=Douglas|last2=McAllister|first2=Jan|last3=Larner|first3=Joseph|date=2014|title=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|journal=Endocrine Journal|volume=61|issue=2|pages=111–117|doi=10.1507/endocrj.ej13-0423|issn=1348-4540|pmid=24189751|doi-access=free}}</ref>
<ref name=bizz2014>{{Cite journal|last1=Bizzarri|first1=M.|last2=Carlomagno|first2=G.|date=July 2014|title=Inositol: history of an effective therapy for Polycystic Ovary Syndrome|journal=European Review for Medical and Pharmacological Sciences|volume=18|issue=13|pages=1896–1903|issn=2284-0729|pmid=25010620}}</ref>
<ref name=kalr2016>{{Cite journal|last1=Kalra|first1=Bharti|last2=Kalra|first2=Sanjay|last3=Sharma|first3=J. B.|date=2016|title=The inositols and polycystic ovary syndrome|journal=Indian Journal of Endocrinology and Metabolism|volume=20|issue=5|pages=720–724|doi=10.4103/2230-8210.189231|issn=2230-8210|pmc=5040057|pmid=27730087 |doi-access=free }}</ref>
<ref name=nest2015>{{Cite journal|last1=Nestler|first1=John E.|last2=Unfer|first2=Vittorio|date=July 2015|title=Reflections on inositol(s) for PCOS therapy: steps toward success|journal= Gynecological Endocrinology|volume=31|issue=7|pages=501–505|doi=10.3109/09513590.2015.1054802|issn=1473-0766|pmid=26177098|s2cid=207490049}}</ref>
<ref name=sort2017>{{Cite journal|last1=Sortino|first1=Maria A.|last2=Salomone|first2=Salvatore|last3=Carruba|first3=Michele O.|last4=Drago|first4=Filippo|date=2017-06-08|title=Polycystic Ovary Syndrome: Insights into the Therapeutic Approach with Inositols|journal=Frontiers in Pharmacology|volume=8|article-number=341|doi=10.3389/fphar.2017.00341|issn=1663-9812|pmc=5463048|pmid=28642705|doi-access=free}}</ref>
</references>
{{DEFAULTSORT:Inositol, D-chiro-}} [[Category:Inositol]]