D-chiro-inositol

Chembox new
Name = "D-chiro"-Inositol
Reference = ["Merck Index", 11th Edition, 4883.]
ImageFile = D-chiro-inositol.png ImageSize = 125px
ImageName = "D-Chiro"-Inositol
IUPACName = "cis"-1,2,4-"trans"-3,5,6
-Cyclohexanehexol
OtherNames = DCI
1,2,4/3,5,6-Hexahydroxycyclohexane
Section1 = Chembox Identifiers
CASNo = 643-12-9
Section2 = Chembox Properties
Formula = C₆H₁₂O₆
MolarMass = 180.16 g/mol
OpticalActivity = [α] 23/D +55°, c = 1.2 in H2O
MeltingPt = 230 °C

D-chiro-inositol (commonly abbreviated DCI) is a member of a family of related substances often referred to collectively as "inositol," although that term encompasses several isomers of questionable biological relevance. It is known to be an important secondary messenger in insulin signal transduction. [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=]

DCI is not abundant in most diets although it can be found in significant quantities in buckwheat farinetta and some other foods. It is possible that in higher vertebrates DCI is made from myo-inositol via the action of an epimerase.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] 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.

DCI appears to have substantial beneficial effects for PCOS, an observation rationalized by the apparent role of DCI in the etiology of PCOS.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=] 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=] cite journal |author=Nestler JE, Jakubowicz DJ, Iuorno MJ |title=Role of inositolphosphoglycan mediators of insulin action in the polycystic ovary syndrome |journal=J. Pediatr. Endocrinol. Metab. |volume=13 Suppl 5 |issue= |pages=1295–8 |year=2000 |pmid=11117673 |doi=] 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. 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=] 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=]

References