1D-chiro-Inositol

1D-chiro-Inositol[1]
D-chiro-Inositol
Names
IUPAC name
1D-chiro-Inositol[2]
Systematic IUPAC name
(1R,2R,3S,4S,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexol
Other names
DCI
cis-1,2,4-trans-3,5,6-Cyclohexanehexol
1D-1,2,4/3,5,6-Cyclohexanehexol[2]
1,2,4/3,5,6-Hexahydroxycyclohexane
(+)-inositol[2]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.359 Edit this at Wikidata
UNII
  • InChI=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 checkY
    Key: CDAISMWEOUEBRE-LKPKBOIGSA-N checkY
  • O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O
Properties
C6H12O6
Molar mass 180.156 g·mol−1
Melting point 230 °C (446 °F; 503 K)
[α]23/D +55°, c = 1.2 in H2O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1D-chiro-Inositol[2] or D-chiro-inositol[3] (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.[4][5]

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.[6][7][8][9][10]

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.[4] In clinical practice, it improves insulin signaling, thus restoring physiological insulin levels in resistant subjects.[3]

Hormonal treatment

D-chiro-inositol has been used to induce ovulation in women with polycystic ovary syndrome.[3]

DCI depresses the expression of the steroidogenic enzyme aromatase, which is responsible for the conversion of androgens to estrogens.[3] One pilot study found males taking DCI had increased androgens and reduced estrogen.[5]

References

  1. ^ Merck Index, 11th Edition, 4883
  2. ^ a b c d IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-104.2.1". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.
  3. ^ a b c d 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
  4. ^ a b 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. doi:10.1080/15604280212528. ISSN 1560-4284. PMC 2478565. PMID 11900279.
  5. ^ a b Monastra G, Vazquez-Levin M, Bezerra Espinola MS, Bilotta G, Laganà AS, Unfer V (June 2021). "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. doi:10.1186/s12610-021-00131-x. PMC 8173878. PMID 34078260.
  6. ^ 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. doi:10.3389/fphar.2017.00341. ISSN 1663-9812. PMC 5463048. PMID 28642705.
  7. ^ Kalra, Bharti; Kalra, Sanjay; Sharma, J. B. (2016). "The inositols and polycystic ovary syndrome". Indian Journal of Endocrinology and Metabolism. 20 (5): 720–724. doi:10.4103/2230-8210.189231. ISSN 2230-8210. PMC 5040057. PMID 27730087.
  8. ^ Nestler, John E.; Unfer, Vittorio (July 2015). "Reflections on inositol(s) for PCOS therapy: steps toward success". Gynecological Endocrinology. 31 (7): 501–505. doi:10.3109/09513590.2015.1054802. ISSN 1473-0766. PMID 26177098. S2CID 207490049.
  9. ^ 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. ISSN 2284-0729. PMID 25010620.
  10. ^ 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. doi:10.1507/endocrj.ej13-0423. ISSN 1348-4540. PMID 24189751.