Alpha Lipoic Acid

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Natural versus Synthetic - Sometimes 'Natural' is Better

Alpha lipoic acid is a coin with two sides. As an antioxidant, it inhibits reactions promoted by oxygen or peroxides that destroy or corrupt cells. When taken as a supplement, alpha lipoic acid (ALA) increases the production of gluthathione which helps dissolve toxic substances in the liver by neutralizing free radicals produced in our bodies and protecting cells. ALA’s natural form can be found in tiny amounts in many protein rich foods, such as meats and spinach. It is also produced in small amounts within the human body. Manufacturers find it convenient and profitable to keep you uninformed of the risks in taking synthesized forms of this important neutraceutical. The result is your wasted money and compromised health. During attempts to produce the natural form of ALA, 50% of the effort results in a form of ALA that is an inferior yet symmetrical copy of the natural form. The symmetrical by product not only is inferior in effect, but compromises the effects of the natural form of ALA.

Your body is designed in such a way that it can usually make more efficient use of the natural isomer of a molecule than it can with that molecule's synthetic look-alike. Alpha-tocopherol (Vitamin E) is a great example milligram for milligram. The d- form of the molecule is much better utilized and retained by the body than is the dl- mixture. Still, in the case of dl-alpha-tocopherol, there's nothing particularly dangerous about having those extra, synthetic isomers in your supplement, they're just weaker, less effective imitations of the original.

Good Isomers, Bad Isomers

In other cases, however, putting the wrong isomer into your body can actually harm you. An example that's becoming well known is trans-fatty acids. Most health-conscious people know something about trans- fats, but few people understand what they are or why they're dangerous. Found in large quantities in most margarines, but also sprinkled throughout the processed food universe, synthetic trans-fatty acids are really just unnatural isomers of natural polyunsaturated fats. When you expose the natural "cis-" isomer of a polyunsaturated fat to a great deal of heat and pressure (as is done in the partial hydrogenation of vegetable oils), you can literally twist its structure, rearranging the molecule's orientation in space. Thus the synthetic trans- isomer is created. (4) Trans fatty acids are silent killers in the human body.

Many important molecules required for life exist in two forms. These two forms are non-superimposable mirror images of each other, i.e.: they are related like our left and right hands. Hence this property is called chirality, from the Greek word for hand. The two forms are called enantiomers (from the Greek word for opposite) or optical isomers, because they rotate plane-polarized light either to the right or to the left.

Whether or not a molecule or crystal is chiral is determined by its symmetry. A molecule is achiral (non-chiral) if and only if it has an axis of improper rotation, that is, an n-fold rotation (rotation by 360°/n) followed by a reflection in the plane perpendicular to this axis maps the molecule on to itself. Thus a molecule is chiral if and only if it lacks such an axis. Because chiral molecules lack this type of symmetry, they are called dissymmetric. They are not necessarily asymmetric (i.e. without symmetry), because they can have other types of symmetry. However, all amino acids (except glycine) and many sugars are indeed asymmetric as well as dissymmetric. Nearly all biological polymers must be homochiral (all its component monomers having the same handedness). Another term used is "optically pure" or "100 % optically active" to function. All amino acids in proteins are ‘left-handed’, while all sugars in DNA, RNA and in the metabolic pathways are ‘right-handed’.

A 50/50 mixture of left- and right-handed forms is called a racemate or racemic mixture. Racemic polypeptides could not form the specific shapes required for enzymes because they would have the side chains sticking out randomly. Also, a wrong-handed amino acid disrupts the stabilizing helix in proteins. DNA could not be stabilized in a helix if even a single wrong-handed monomer were present, so it could not form long chains. This means it could not store much information, so it could not support life.

Problems with Some Commercially Available ALA Supplements

Commercially produced "alpha lipoic acid" is no different. When producing ALA in a laboratory, the S- form of ALA is a waste of money and time. Your body spits it out like a fish does a hook and it comprises 50% of the mixture sold as alpha lipoic acid on the market. In the past, the R+ version was only available in small quantities for research by scientists. (1)

The S- form that is taking up 50% of your supplement is not just a weaker version of the real thing, like the alpha-tocopherol dl- product. In fact, the S- form of ALA is its negative counterpart.. When he reported his findings about the opposing effects of the two forms of lipoic acid on the energy-producing powers of mitochondrial particles, Dr. Guido Zimmer stated that the S- form of ALA, which is present as about 50%, needs to be eliminated. (2)

The differences between the two forms of ALA can completely alter the effects of the sugars in your body. When looking at the differences between the R+- and S- forms of lipoic acid in terms of their effects on the body’s metabolism of blood sugar, their protective antioxidant activities or effects on mitochondria and the preliminary evidence of their effects on the aging process itself, Dr. Zimmer and other lipoic acid researchers found that there are cases where the S- is merely less effective than the R+ or just totally ineffective. As you dig into the lipoic acid story, you’ll also see many cases in which the S- actually counteracts the benefits of R+ alpha lipoic acid! (3) In laboratory animals, the R+ entainomer caused a 34% increase in glucose uptake by skeletal muscle cells in response to insulin while those fed the S- entainomer had no improvement in blood glucose disposal. (9)

The Positive Effects of R+ ALA

As a weight training athlete, even if you are very insulin sensitive by nature, R+ ALA will enable your skeletal muscle bellies to hold more nutrients such as glycogen and amino acids.

To function properly, cells need a steady fuel supply. Blood sugar/muscle glygogen is the primary fuel for most cells in the body. The body produces the hormone insulin precisely in order to help get energy to the cells that need it such as skeletal muscle. Insulin is like a "key" that turns on the glucose transport "ignition" (insulin receptor) which is located on the surface of the cell.

When the "key" (insulin) activates the "ignition" (the insulin receptor), it turns on the engines of the "tanker trucks" (GLUcose Transporters, or GLUTs) that do the work of hauling glucose (blood sugar) out of the bloodstream and into cells. So to get bodily cells the energy they need, and to keep blood sugar from building up to dangerously high levels, insulin must tell bodily cells (skeletal muscle) to absorb blood sugar. In healthy individuals, the cells will obey the signal and mobilize the GLUT transporters.

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