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{{DISPLAYTITLE:<small>D</small>-''chiro''-Inositol}} |
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{{DISPLAYTITLE:1<small>D</small>-''chiro''-Inositol}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 430389778 |
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| verifiedrevid = 443555991 |
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| Name = <small>D</small>-''chiro''-Inositol |
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| Name = 1<small>D</small>-''chiro''-Inositol |
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| Reference =<ref>'']'', 11th Edition, '''4883'''</ref> |
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| Reference =<ref>'']'', 11th Edition, '''4883'''</ref> |
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| ImageFile = D-chiro-inositol.png |
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| ImageFile = D-chiro-inositol.png |
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| ImageSize = 125px |
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| ImageSize = 125px |
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| ImageName = ''D-Chiro''-Inositol |
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| ImageName = <small>D</small>-''chiro''-Inositol |
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| IUPACName = ''cis''-1,2,4-''trans''-3,5,6<br />-Cyclohexanehexol |
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| IUPACName = 1<small>D</small>-''chiro''-Inositol<ref name=bb/> |
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| SystematicName = (1''R'',2''R'',3''S'',4''S'',5''S'',6''S'')-Cyclohexane-1,2,3,4,5,6-hexol |
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| OtherNames = DCI <br /> 1,2,4/3,5,6-Hexahydroxycyclohexane |
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| 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" /> |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| IUPHAR_ligand = 4645 |
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| CASNo = 643-12-9 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| PubChem = |
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| CASNo = 643-12-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 6R79WV4R10 |
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| PubChem = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10254647 |
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| ChemSpiderID = 10254647 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 27372 |
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| ChEBI = 27372 |
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| SMILES = O1(O)(O)(O)(O)1O |
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| SMILES = O1(O)(O)(O)(O)1O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=6|H=12|O=6 |
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| C=6|H=12|O=6 |
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| OpticalActivity = 23/D +55°, c = 1.2 in H<sub>2</sub>O |
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| SpecRotation = 23/D +55°, c = 1.2 in H<sub>2</sub>O |
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| MeltingPtC = 230 |
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| MeltingPtC = 230 |
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'''1<small>D</small>-''chiro''-Inositol'''<ref name=bb/> or '''<small>D</small>-''chiro''-inositol'''<ref name=arag2021/> (often abbreviated '''DCI''') is a ] with formula {{chem2|C6H12O6}}, one of the nine ]s of ] (which may be collectively called "inositol"). The molecule has a ring of six ] atoms, each bound to one ] atom and one ] (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 ], hence its name. Its ] (mirror compound) is ]. |
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'''<small>D</small>-''chiro''-Inositol''' (commonly abbreviated '''DCI''') is a member of a family of related substances often referred to collectively as "]," although that term encompasses several ]s of questionable biological relevance. It is known to be an important ] in ] ].<ref>{{cite journal |author=Larner J |title=D-chiro-inositol--its functional role in insulin action and its deficit in insulin resistance |journal=Int. J. Exp. Diabetes Res. |volume=3 |issue=1 |pages=47–60 |year=2002 |pmid=11900279 |doi=10.1080/15604280212528 |pmc=2478565}}</ref> |
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Compared to its more common isomer ], DCI seems to have relatively minor roles in ] and medicine, mostly connected to the biochemistry of ] and other ]s.<ref name=larn2002/><ref name=vasq2021/> |
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DCI is not abundant in most diets although it can be found in significant quantities in ] ], and some other foods. It is possible that in higher vertebrates DCI is made from myo-inositol via the action of an ].<ref name="pmid12051772">{{cite journal |author=Sun TH, Heimark DB, Nguygen T, Nadler JL, Larner J |title=Both myo-inositol to chiro-inositol epimerase activities and chiro-inositol to myo-inositol ratios are decreased in tissues of GK type 2 diabetic rats compared to Wistar controls |journal=Biochem. Biophys. Res. Commun. |volume=293 |issue=3 |pages=1092–8 |year=2002 |pmid=12051772 |doi=10.1016/S0006-291X(02)00313-3}}</ref> Contrary to common claims of the non-availability of DCI, it is in fact commercially available to the public as a nutritional supplement in the US. |
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==Biochemistry and physiology == |
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DCI appears to have substantial beneficial effects for ], an observation rationalized by the apparent role of DCI in the etiology of PCOS.<ref name="pmid10219066">{{cite journal |author=Nestler JE, Jakubowicz DJ, Reamer P, Gunn RD, Allan G |title=Ovulatory and metabolic effects of D-chiro-inositol in the polycystic ovary syndrome |journal=N. Engl. J. Med. |volume=340 |issue=17 |pages=1314–20 |year=1999 |pmid=10219066 |doi=10.1056/NEJM199904293401703}}</ref><ref name="pmid15251831">{{cite journal |author=Iuorno MJ, Jakubowicz DJ, Baillargeon JP, ''et al.'' |title=Effects of d-chiro-inositol in lean women with the polycystic ovary syndrome |journal=Endocrine practice |volume=8 |issue=6 |pages=417–23 |year=2002 |pmid=15251831 |doi=}}</ref><ref name="pmid11117673">{{cite journal |author=Nestler JE, Jakubowicz DJ, Iuorno MJ |title=Role of inositolphosphoglycan mediators of insulin action in the polycystic ovary syndrome |series=13 |journal=J. Pediatr. Endocrinol. Metab. |volume=Suppl 5 |issue= |pages=1295–8 |year=2000 |pmid=11117673 |doi=}}</ref> In double-blind studies, women with PCOS who received DCI experienced the following statistically significant benefits when compared with a control group: lowered free and total testosterone, lowered blood pressure, increased insulin sensitivity and a corresponding improvement in glucose disposal, and increased frequency of ovulation. <ref name="pmid10219066"/><ref name="pmid15251831"/> |
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==Dietary sources== |
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=== Occurrence === |
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The common isomer ''myo''-inositol is converted into DCI in the human body by an ] dependent ], ].<ref name=sort2017/><ref name=kalr2016/><ref name=nest2015/><ref name=bizz2014/><ref name=heim2014/> |
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Significant dietary sources include; ] (particularly buckwheat farinetta), ], and '']'' (fig leaf melon). |
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===Insulin interactions=== |
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==See also== |
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*] |
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D-''chiro''-inositol is known to be an important ] in ] ]. 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/> |
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==References== |
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{{reflist}} |
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===Hormonal treatment=== |
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{{DEFAULTSORT:Inositol, D-chiro-}} |
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] |
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D-''chiro''-inositol has been used to induce ovulation in women with polycystic ovary syndrome.<ref name=arag2021/> |
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] |
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DCI depresses the expression of the ] ], which is responsible for the conversion of ] to ].<ref name=arag2021/> One pilot study found males taking DCI had increased androgens and reduced estrogen.<ref name=vasq2021/> |
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== References == |
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<references> |
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<ref name=bb>{{BlueBook2013|rec=104.2.1}}</ref> |
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<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=] |volume=31 |issue=1 |pages=13 |date=June 2021 |pmid=34078260 |pmc=8173878 |doi=10.1186/s12610-021-00131-x |url= |issn= |doi-access=free }}</ref> |
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<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> |
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<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> |
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<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> |
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<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> |
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<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> |
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<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> |
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<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|page=341|doi=10.3389/fphar.2017.00341|issn=1663-9812|pmc=5463048|pmid=28642705|doi-access=free}}</ref> |
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</references> |
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{{DEFAULTSORT:Inositol, D-chiro-}} |
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] |