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R-Lipoic Acid benefits

R-Lipoic Acid & R-Dihydrolipoic Acid - The naturally occurring forms of alpha lipoic acid

R-Lipoic Acid (RLA) and its reduced form, R-Dihydrolipoic Acid (R-DHLA) may prove to be the most important nutraceutical compounds on the market today. The redox couple has powerful antioxidant functions, serves as a critical co-factor in ATP production, regulates lipid and carbohydrate metabolism, signal transduction, gene transcription and cellular proliferation.

RLA/R-DHLA is also neuroprotective, chelates heavy metals, can reverse enzyme and DNA oxidative damage and crosses the blood brain barrier. R-Lipoic Acid has been shown to be more effective by a factor of 8-10 over the commercially available alpha lipoic acid for reducing inflammation, and with R-Dihydro Lipoic Acid, regulates the pro-inflammatory COX-2 and LOX pathways. This indicates the unnatural SLA is interfering with the body's utilization of the R form. Like natural sugars, (D-form) and amino acids, (L form) the R (+), or dextro (d) form is the natural form of lipoic acid.

Alpha-Lipoic Acid Occurs In 3 Different Forms

  1. R-Lipoic Acid (the R (+) enantiomer) is the pure form found in nature and the human body that is responsible for most of alpha-lipoic acid's beneficial effects.
  2. S-Lipoic acid (The S (-) enantiomer) is a by-product from chemical synthesis.
  3. Alpha-lipoic acid consists of 50/50 racemic mixture of the R and S enantiomers and is the normal commercially available form of lipoic acid.

For a definition and explanation of the meaning of R and S and + and - relative to chiral molecules, see Chirality.

R-Lipoic Acid is the only naturally-occurring form of alpha-lipoic acid.

What are the Benefits of R-Lipoic Acid?

R-Lipoic Acid significantly reduces inflammation, an underlying cause of the degenerative diseases of aging and is more potent by a factor of 10 over commercial Alpha Lipoic Acid. (1)

R-Lipoic acid was found to be more bioavailable than S-lipoic acid when taken orally in a human study. (2)

R-Lipoic Acid protects body fats against oxidative damage and reverses stress damage in the heart. (3)

R-Lipoic Acid was more effective than the S form in a battery of metal chelation tests. One hypothesis of the cause of diabetic complications involves overloading by transition metals which could explain the stereospecific effect of the R-form. (4)

R-Lipoic Acid is the only form of lipoic acid found in nature and therefore the only form recognized by the critical mitochondrial enzymes. (5)

R-Lipoic acid was more effective than S-lipoic acid in enhancing insulin-stimulated glucose transport and metabolism in insulin-resistant rat skeletal muscle. (6)

R-Lipoic Acid increases cellular and mitochondrial antioxidant activity and prevents mitochondrial decay. This effectively attenuates the reported increase in oxidative stress with aging. (8)

R-Lipoic acid was more effective than racemic alpha-lipoic acid and S -alpha-lipoic acid in preventing cataracts in rats. (11)

R-Lipoic Acid improves memory, reverses cognitive dysfunction, and protects the brain from neurodegeneration associated with aging. (8-10) (23)

R-Lipoic Acid supplementation improves metabolic activity and lowers oxidative stress and damage evident in aging. (11)

R-Lipoic Acid significantly increase insulin sensitivity, enhances glucose transport, increases metabolic rate and reduces the gain in body fat from aging. (12, 13)

R-Lipoic Acid has insulin-mimetic effects in glucose uptake in insulin resistant cells and may have therapeutic implications in restoring glucose availability in tissues such as the skeletal muscle. (14)

R-Lipoic Acid significantly increases or maintain levels of other antioxidants including Coenzyme Q10, vitamin C, vitamin E and glutathione. (15-17)

R-Lipoic Acid prevents depletion of the glutathione pool within the cytoplasm and mitochondria. Pre-treatment of PC12 cells with RLA leads to the preservation of mitochondrial complex I activity lost due to glutathione depletion. (18)

The R-(+) enantiomer is much more effective than the S-(-) enantiomer at enhancing insulin-stimulated glucose transport and non-oxidative and oxidative glucose metabolism. (21)

R-Lipoic Acid, through its positive effects on cellular energy metabolism, attenuates metabolic dysfunction associated with advanced glycation endproducts (AGEs). AGEs accumulate on long-lived proteins, including beta-amyloid plaques in Alzheimer's disease and contributes to neuronal dysfunction and cell death. (21, 22)

R-Lipoic Acid, a membrane permeable antioxidant, prevents the up-regulation of the AGE -induced gene expression responsible for regulating nitric oxide (NO) production. NO oxidizes and nitrates proteins which are markers of a chronic neuroinflammatory condition. This mechanism is relevant for Alzheimer's disease and for many chronic inflammatory conditions. (23)

The dihydrolipoamide dehydrogenase component has a clear preference for R-lipoic acid, a substrate which reacts 24 times faster than the S-enantiomer. (24)

R-lipoic acid and R-Dihydrolipoic acid is available in stabilized capsules and liquid at our store.

Does your lipoic acid supplement contain only the form found in nature?

Or does it also include a synthetic by-product that may interfere with the natural form's beneficial effects?

References

  1. Pharmaceutical composition containing R-.alpha.-lipoic acid or S-.alpha.-lipoic acid as active ingredient. Ulrich H, Weischer CH, et al. US Patent 5,728,735, 1998.
  2. Enantioselective pharmacokinetics and bioavailability of different racemic a-lipoic acid formulations in healthy volunteers. Hermann R, Niebch G, Borbe HO, et al. Eur J Pharm Sci. 1996;4:167-174.
  3. Oxidative stress in the aging rat heart is reversed by dietary supplementation with (R)-(alpha)-lipoic acid. Suh JH, Shigeno ET, et al. FASEB J 2001 Mar; 15(3): 700-6.
  4. Thioctic (lipoic) acid: a therapeutic metal-chelating antioxidant? Ou P, Tritschler HJ, Wolff SP. Biochem Pharmacol 1995; 50:123-126.
  5. Influence of selegiline and lipoic acid on the life expectancy of immunosuppressed mice. Freisleben HJ, Neeb A, et al. Arzneimittelforschung 1997 Jun; 47(6): 776-80.
  6. Differential effects of lipoic acid stereoisomers on glucose metabolism in insulin-resistant skeletal muscle. Streeper RS, Henriksen EJ, et al.Am J Physiol. 1997;273(1 Pt 1):E185-191.
  7. Stereospecific effects of R-lipoic acid on buthionine sulfoximine-induced cataract formation in newborn rats. Maitra I, Serbinova E, Tritschler HJ, Packer L. Biochem Biophys Res Commun. 1996;221(2):422-429.
  8. Memory loss in old rats is associated with brain mitochondrial decay and RNA/DNA oxidation: partial reversal by feeding acetyl-L-carnitine and/or R-alpha -lipoic acid. Liu , Head E, et al. Proc Natl Acad Sci U S A 2002 Feb 19; 99(4): 2356-61.
  9. Mitochondrial decay in the aging rat heart: evidence for improvement by dietary supplementation with acetyl-L-carnitine and/or lipoic acid. Hagen TM, Moreau R, et al. Ann N Y Acad Sci. 2002 Apr;959:491-507.
  10. Oxidative stress in the aging rat heart is reversed by dietary supplementation with (R)-(alpha)-lipoic acid. Suh JH, Shigeno ET, et al. FASEB J 2001 Mar; 15(3): 700-6.
  11. (R)-alpha-Lipoic acid-supplemented Old Rats Have Improved Mitochondrial Function, Decreased Oxidative Damage, and Increased Metabolic Rate. Hagen TM, Ingersoll RT, et al. FASEB J 1999 13:411-418.
  12. Oral administration of RAC-alpha-lipoic acid modulates insulin sensitivity in patients with type-2 diabetes mellitus: a placebo-controlled pilot trial. Jacob S, Ruus P, et al. Free Rad Biol Med 1999 Aug;27(3-4):309-14.
  13. R-alpha-Lipoic Acid Action on Cell Redox Status, the Insulin Receptor, and Glucose Uptake in 3T3-L1 Adipocytes. Moines H, Trios O, et al. Arch Biochem Biophys 2002 Jan 15; 397(2): 384-91.
  14. Cytokine-induced glucose uptake in skeletal muscle: redox regulation and the role of alpha-lipoic acid. Khanna S, Packer L, et al. Am J Physiol. 1999 May;276(5 Pt 2):R1327-33.
  15. Age-associated decline in ascorbic acid concentration, recycling, and biosynthesis in rat hepatocytes--reversal with (R)-alpha-lipoic acid supplementation. Lykkesfeldt J, Ames BN et al. FASEB J 1998 Sep; 12(12): 1183-9.
  16. Pre-treatment with R-lipoic acid alleviates the effects of GSH depletion in PC12 cells: implications for Parkinson's disease therapy. Bharat S, Cochran BC, et al. Neurotoxicology. 2002 Oct;23(4-5):479-86.
  17. Stereospecific effects of lipoic acids on mammalian pyruvate dehydrogenase complex. Hong YS, Jacobia SJ, et al. Free Radic Biol Med. 1999 Mar;26(5-6):685-94.
  18. Differential effects of lipoic acid stereoisomers on glucose metabolism in insulin-resistant skeletal muscle. Streeper RS, Henriksen EJ, Tritschler HJ, et al. Am J Physiol 1997 Jul; 273(1 Pt 1): E185-91.
  19. Cytosolic and mitochondrial systems for NADH- and NADPH-dependent reduction of alpha-lipoic acid. Haramaki N, Han D, et al. Free Radic Biol Med 1997; 22(3): 535-42.
  20. Stereospecific effects of R-lipoic acid on buthionine sulfoximine-induced cataract formation in newborn rats. Maitra I, Serbinova E, et al. Biochem Biophys Res commun 1996; 221:422-429.
  21. Advanced glycation endproducts induce changes in glucose consumption, lactate production, and ATP levels in SH-SY5Y neuroblastoma cells by a redox-sensitive mechanism. de Arriba SG, Loske C, et al. J Cereb Blood Flow Metab. 2003 Nov;23(11):1307-13.
  22. Anti-inflammatory antioxidants attenuate the expression of inducible nitric oxide synthase mediated by advanced glycation endproducts in murine microglia. Wong A, Dukic-Stefanovic S, et al. Eur J Neurosci. 2001 Dec;14(12):1961-7.
  23. Neuroprotection by the metabolic Antioxidant alpha Lipoic Acid. Packer, L, Tritschler, H; Wessel K, 1997 Free Rad Biol Med 22, Nos 1/2, 359-378.
  24. Interaction of alpha-lipoic acid enantiomers and homologues with the enzyme components of the mammalian pyruvate dehydrogenase complex. Loffelhardt S, Bonaventura C, et al. Biochem Pharmacol. 1995 Aug 25;50(5):637-46.

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