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
643-12-9 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:27372 YesY
ChemSpider 10254647 YesY
ECHA InfoCard 100.010.359
4645
Properties
C6H12O6
Molar mass 180.16 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).
YesY verify (what is YesYN ?)
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

  1. ↑ Merck Index, 11th Edition, 4883
  2. ↑ Larner J (2002). "D-chiro-inositol--its functional role in insulin action and its deficit in insulin resistance". Int. J. Exp. Diabetes Res. 3 (1): 47–60. doi:10.1080/15604280212528. PMC 2478565Freely accessible. PMID 11900279.
  3. ↑ Baumgartner, Stephanie; Genner-Ritzmann, Ruth; Haas, Johann; Amado, Renato; Neukom, Hans (1986). "Isolation and identification of cyclitols in carob pods (Ceratonia siliqua L.)". J. Agric. Food Chem. 34 (5): 827–829. doi:10.1021/jf00071a015.
  4. ↑ Sun TH, Heimark DB, Nguygen T, Nadler JL, Larner J (2002). "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". Biochem. Biophys. Res. Commun. 293 (3): 1092–8. doi:10.1016/S0006-291X(02)00313-3. PMID 12051772.
  5. ↑ PROGRAMA DEL CONGRESO LIBRO DE RESÚMENES. "8 o º CONGRESO DE FITOTERAPIA DE LA SEFIT 8 o º CURSO DE TERAPIAS NATURALES DE LA AEEM" (PDF).
  6. 1 2 Nestler JE, Jakubowicz DJ, Reamer P, Gunn RD, Allan G (1999). "Ovulatory and metabolic effects of D-chiro-inositol in the polycystic ovary syndrome". N. Engl. J. Med. 340 (17): 1314–20. doi:10.1056/NEJM199904293401703. PMID 10219066.
  7. 1 2 Iuorno MJ, Jakubowicz DJ, Baillargeon JP, et al. (2002). "Effects of d-chiro-inositol in lean women with the polycystic ovary syndrome". Endocrine Practice. 8 (6): 417–23. doi:10.4158/EP.8.6.417. PMID 15251831.
  8. ↑ Nestler JE, Jakubowicz DJ, Iuorno MJ (2000). "Role of inositolphosphoglycan mediators of insulin action in the polycystic ovary syndrome". J. Pediatr. Endocrinol. Metab. 13. Suppl 5: 1295–8. PMID 11117673.
  9. ↑ Baillargeon, JP; Diamanti-Kandarakis, E; Ostlund, RE; Apridonidze, T; Iuorno, MJ; Nestler, JE (2006). "Altered D-chiro-inositol urinary clearance in women with polycystic ovary syndrome". Diabetes Care. 29 (2): 300–305. doi:10.2337/diacare.29.02.06.dc05-1070. PMID 16443877.
  10. ↑ Genazzani, AD; Santagni, S; Rattighieri, E; Chierchia, E; Despini, G; Marini, G; Prati, A; Simoncini, T (2014). "Modulatory role of D-chiro-inositol (DCI) on LH and insulin secretion in obese PCOS patients". Gynecol Endocrinol. 30 (6): 438–43. doi:10.3109/09513590.2014.897321. PMID 24601829.
  11. ↑ Laganà, AS; Barbaro, L; Pizzo, A (2015). "Evaluation of ovarian function and metabolic factors in women affected by polycystic ovary syndrome after treatment with D-Chiro-Inositol". Arch Gynecol Obstet. 291 (5): 1181–6. doi:10.1007/s00404-014-3552-6. PMID 25416201.
  12. ↑ La Marca, A; Grisendi, V; Dondi, G; Sighinolfi, G; Cianci, A (2015). "The menstrual cycle regularization following D-chiro-inositol treatment in PCOS women: a retrospective study". Gynecol Endocrinol. 31 (1): 52–6. doi:10.3109/09513590.2014.964201. PMID 25268566.
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