All About Alpha Lipoic Acid
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
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
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
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.
Importance Of Insulin Sensitivity
Unfortunately, our fast paced lifestyles and highly-processed food diets cause
most of us to consume more calories and particularly, more carbohydrates than
our bodies can handle.
After years of being told by insulin to take in more glucose than they can use,
eventually the receptors stop responding properly to insulin's signal. They
become desensitized. (6) This is the beginning of insulin resistance.
Insulin resistance itself is a potential killer. One of insulin's functions is
to control the release of free fatty acids from bodily tissues into the
bloodstream. When the body doesn't respond properly to insulin, plasma levels of
free fatty acids rise higher. (7)
High levels of free fatty acids keep blood vessels constricted by interfering
with the action of nitric oxide, the molecule that helps your blood vessels to
relax. (8) As a result, high blood levels of free fatty acids cause insulin
resistant people to have high blood pressure.
Insulin sensitivity appears to be a crucial factor in achieving what we all
desire: a very favorable body composition resulting in an aesthetically pleasing
For strength training athletes, it is key in the sense that it promotes and
facilitates the uptake of vital, precious nutrients from the bloodstream to
repair damaged muscle fibers.
Also, it makes insulin's job a lot easier and this promotes a very wide array of
health benefits for anyone. It is the antithesis of insulin resistance. When
blood glucose remains high, the pancreas responds in frustration by pumping out
even more insulin in an attempt to compensate for the resistance. This works for
awhile, although the process becomes less and less efficient with time. After a
meal, a "yo yo" effect takes place.
Regarding weight training athletes in particular, the skeletal muscles may not
obey insulin and uptake the nutrients they desperately need to grow.
In response, insulin is overproduced AGAIN and forces blood sugar to drop too
low. When that happens, the liver starts over producing glucose to get blood
sugar levels back up. Then, the pancreas overcompensates by overproducing more
insulin due to high sugar levels, AGAIN. This results in high fasting blood
sugar and insulin levels 24/7, even in a fasted state due to the aforementioned
The Problem - Insulin Resistance
What happens to these nutrients without a home? They remain in the bloodstream
for prolonged periods of time. They wind up in places they do not belong. This
causes huge problems over time.
The most glaring is the accumulation of body fat in the visceral region for men
and the hips and buttocks for the ladies. This occurs because glucose, fats and
other nutrients are refusing to be cleared from the bloodstream. Of the liver,
skeletal muscle and adipose cells, the fat cells are the last to become
resistant. They become the dumping ground for excess blood fats (triglycerides)
High levels of triglycerides in the bloodstream for prolonged periods results in
the accumulation of arterial plaque. Insulin resistance facilitates the
oxidation of LDL and VLDL (the bad kind) cholesterol. This sets the stage for
atherosclerosis. (5) The narrowing of the inside of arterial walls surrounding
the heart due to the buildup sticky, fatty atherosclerotic plaque flourishes in
the insulin resistant, hyperglycemic human body.
So, you have here a situation where incoming calories are primarily stored as
bodyfat. Energy demands placed on the body derive the necessary calories to be
burned for fuel mainly from skeletal muscle (stored glycogen and amino acids).
The reason for the latter is the fact that fat cannot be used for fuel in the
presence of high blood insulin levels, whether in the fed or fasting state.
Does this sound like a bodybuilder's nightmare? You bet it does.
Solutions To The Problem
The good news is there are solutions. What I've tried to focus on in this
article is one supplement which can help throw this problem in reverse, combined
with a positive change in eating habits and exercise.
The second point I've tried to accomplish is to uncover the truth about
commercially sold "alpha lipoic acid" supplements. We need to choose the ALA
supplement with care to be sure that we are not counteracting the benefit from
the natural entainomer we need to build a better body for our health and well
Note: Regarding insulin sensitivity, I have found two publications to be
profoundly accurate in content for the hardcore bodybuilder. I regularly read
and reread "Chemical Muscle Enhancement" and "Building The Perfect Beast" by
Author L Rea.
Every time I re-read one of his books or articles, I discover a fresh nugget of
truth which brings some form of new progress. His cutting edge approach to what
works in the real world has changed my life and improved my health. I highly
recommend his work and products.
About The Author
Clarityandfocus has a Bachelor of Science in Social Work with a Minor in
Psychology with 24 years of devoted experience and a passion for the study of
bodybuilding and nutrition.
Dr. Ryan Streeper and colleagues, in The American Journal of Physiology and Dr.
Bruce Ames, in Strategies for Engineered Negligible Senescence:
Dr. Guido Zimmer and colleagues, in Methods in Enzymoogy:
Valenzuela A, Morgado N. Trans fatty acid isomers in human health and in the
food industry. Biol Res. 1999;32(4):273-87.
Hu FB, Stampfer MJ, Manson JE, Rimm E, Colditz GA, Rosner BA, Hennekens CH,
Willett WC. Dietary fat intake and the risk of coronary heart disease in women.
N Engl J Med. 1997 Nov 20;337(21):1491-9.
Packer L, Tritschler HJ. Antioxidant properties and clinical applications of
alpha-lipoic acid and dihidrolipoic acid. In Cadenas E, Packer L. Handbook of
Antioxidants. New York: Marcel Dekker, 1996: 545-91.
Kwiterovich PO Jr. The metabolic pathways of high-density lipoprotein,
low-density lipoprotein, and triglycerides: a current review. Am J Cardiol. 2000
Egan BM, Greene EL, Goodfriend TL. Nonesterified fatty acids in blood pressure
control and cardiovascular complications. Curr Hypertens Rep. 2001
Streeper RS, Henriksen EJ, Jacob S, Hokama JY, Fogt DL, Tritschler HJ.
Differential effects of lipoic acid stereoisomers on glucose metabolism in
insulin-resistant skeletal muscle. Am J Physiol. 1997 Jul;273(1 Pt 1):E185-91.
Yip J, Facchini FS, Reaven GM. Resistance to insulin-mediated glucose disposal
as a predictor of cardiovascular disease. J Clin Endocrinol Metab. 1998
Cotton, F.A. and Wilkinson, G., 1980. Advanced Inorganic Chemistry: a
Comprehensive Text, 4th Ed., John Wiley & Sons, Inc, NY, p. 47.
Morrison, R.T. and Boyd, R.N., 1987. Organic Chemistry, 5th ed. Allyn & Bacon
Cotton, F.A. and Wilkinson, G., 1980. Advanced Inorganic Chemistry: a
Comprehensive Text, 4th Ed., John Wiley & Sons, Inc, NY, p. 47.
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