D-chiro-Inositol

D-chiro-Inositol^[1]

Names
IUPAC names cis-1,2,4-trans-3,5,6 -Cyclohexanehexol
Other names DCI 1,2,4/3,5,6-Hexahydroxycyclohexane
Identifiers
CAS Number	643-12-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27372 Y
ChemSpider	10254647 Y
ECHA InfoCard	100.010.359
IUPHAR/BPS	4645
InChI 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 Y Key: CDAISMWEOUEBRE-LKPKBOIGSA-N Y
SMILES O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O
Properties
Chemical formula	C6H12O6
Molar mass	180.16 g·mol−1
Melting point	230 °C (446 °F; 503 K)
Chiral rotation ([α]D)	[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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Infobox references

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.^[2]

DCI is not abundant in most diets. It can be found in carob tree (Cearatonia siliqua L.) pods.^[3] It is likely that in higher vertebrates DCI is made from myo-inositol via the action of an epimerase.^[4] DCI is commercially available to the public as a nutritional supplement in several countries. Caronositol^® is natural D-chiro-Inositol obtained from carob extract by a patented process. Caronositol^® is used in treatment of metabolic and hormonal polycystic ovarian syndrome.^[5]

D-chiro-Inositol deficiency and Insulin Resistance

DCI appears to have substantial beneficial effects for PCOS, an observation rationalized by the apparent role of DCI in the etiology of PCOS.^[6][7][8] In non-human primates and in humans, insulin resistance may be related to a deficiency in a putative D-chiro-inositol–containing phosphoglycan mediator of insulin action. Recent clinical research findings confirmed that D-chiro-Inositol (DCI) level reduces to almost half from the normal level, while there is no change in myo-inositol level. Hence, DCI deficiency may contribute to the insulin resistance and leads to PCOS.^[9]

D-chiro-Inositol and PCOS treatment

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.^[6][7] D-chiro-inositol improved several endocrine parameters like improved (luteinizing hormone [LH], LH/follicle stimulating hormone [FSH], androstenedione and insulin), insulin response to oral glucose tolerance test reported the significant improvement of insulin sensitivity as well as the gonadotropin-releasing hormone (GnRH)-induced (10 µg, in bolus) LH response. BMI decreased, though no lifestyle modification was requested. PCOS patients with diabetic relatives showed greater improvement after DCI administration. DCI administration is effective in restoring better insulin sensitivity and an improved hormonal pattern in obese hyperinsulinemic PCOS patients.^[10] D-Chiro-Inositol significantly reduced systolic blood pressure, Ferriman-Gallwey score, LH, LH/FSH ratio, total Testosterone, free Testosterone, ∆-4-Androstenedione, Prolactin, HOMA Index, and increased SHBG and Glycemia/IRI ratio in PCOS patients. D-Chiro-Inositol improved menstrual cycle regularization. D-Chiro-Inositol is effective in improving ovarian function and metabolism of patients affected by PCOS.^[11] DCI treatment significantly improved percentage of women reporting regular menstrual cycles, decreased serum AMH levels and indexes of insulin resistance. DCI is associated to clinical benefits for many women affected by PCOS including the improvement in insulin resistance and menstrual cycle regularity.^[12]

References