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    Features

    A Different Spin On Quality

    When searching for the heir apparent to the throne held by the 'Queen of Quality,' should we look for a chemist or a biologist?

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    Anthony Almada, BSc10.01.03
    "Four out of five nutraceutical industry professionals chose 'quality' as the most important criterion." What the interviewing agency failed to ask is "How do you spell quality?" If we reflect upon the backdrop of the nutraceutical products landscape (defined as dietary supplements, foods, beverages and chewing gum attempting to make a "soft" claim in relation to benefiting the prospective user's health or disease state), one sees "quality" very frequently defined by chemical composition and inter-batch uniformity-chemoprofiling. The adoption of and familiarity with the initialism "HPLC" is but one testament to this. A confirmatory HPLC assay for a nutraceutical ingredient or product has garnered value similar to that of a randomized double-blind, placebo-controlled clinical trial for such an ingredient's/product's on- and off-label claims. The advent and proliferation of private analytical chemistry laboratories is another sign of chemoprofiling going to prime time.

    Chemoprofiling invokes memories of the "newspaper assay" headline stories and illuminates the controversial success of ConsumerLab.com. It also explains the thrust behind the vigorous and assiduous pursuit of methodological standards by sterling organizations like AOAC and USP. Collectively, this constellation of events and entities reinforces the perceived need for chemoprofiling, magnified by recent media stories exposing the ostensibly rampant lack of label claim verity within this collective industry.

    But is chemoprofiling the ideal assessment tool of a nutraceutical product's quality? Do FDA's proposed good manufacturing practices (GMPs) for dietary supplements, if and when implemented, confer the platinum standard of "quality" upon an ingredient or finished good earning such a stamp? Stated differently, does the chemical composition of a product (and its inter-batch uniformity) directly and substantially bear upon the safety and effectiveness of the product? An emphatic "Yes" for single chemical entities and a likely "No" for heteromolecular entities, and for compositions that combine one or more of each. One can define the former class of ingredients as also being PURE or NEAR PURE chemicals. This would include items like vitamins, amino acids and purified phytochemicals and zoochemicals e.g. curcumin and lactoferrin, respectively. Heteromolecular entities include bioactives like plant extracts, aquaculture products, conjugated linoleic acid (CLA, a cocktail of various fatty acids, both conjugated and unconjugated, varying from brand to brand), bovine hydroxyapatite, colostrums, etc.

    If the claimed ingredient on a label indeed is not wholly identical in chemistry to that found in the 55 gallon drum or finished good, the product is what's considered chemically, and perhaps from the vista of the FDA towers, "regulatorially" misbranded. More importantly, said product may be biologically innocuous or hazardous, another departure from the anticipated scientific legacy of the product. One cannot exclude the remote possibility that the chemical entity that is present as a proxy for the labeled compound could display superior biological activity but this is less than likely.


    Better Living Through Stereochemistry



    Back in the early to mid 1980s, when "crystalline free form" amino acids were first marketed as dietary supplements, use of the L- designation was commonplace and even featured. It is likely that many industry participants throughout the value chain did not know the significance of this designation but equated it with the "natural" form of amino acids (despite the sales of dl-methionine and DL-phenylalanine, a "racemic" mixture of the D- and L- isomers of each amino acid). It is apparent that some still do not-the lingering number of nationally distributed nutraceuticals that still affix the L- designation to taurine and glycine illustrates such (time to hire a new R&D director or contract manufacturer for such glaring ignorance).

    Preceding the advent of L-amino acids was the sales and marketing of d-alpha-tocopherol (correctly referred to as RRR-alpha-tocopherol) and its petroleum-derived second cousin dl-alpha-tocopherol (properly referred to as all-rac-alpha-tocopherol, a mixture of eight different isomers of alpha-tocopherol). Because of the cost differential between RRR and all-rac forms, and their very similar gross physical appearance (amber-colored oil), independent analyses were advocated and promulgated by the manufacturers and marketers of the RRR form.

    That initial foray into chemoprofiling by confirmation of the isomer profile or stereochemistry-the relationship between different atoms attached on a molecule, in essence a 3-D, surround vision of how they exist in space-has had only a few successive events. When the beta-amino acid carnitine was first introduced as a dietary supplement ingredient in the U.S. in the early 1980s it was offered only as the racemate (a "racemic" dl-carnitine mixture, defined by the presence of near equal amounts of both the d- isomer and the l- isomer. The "dl-descriptor is essentially interchangeable with DL-carnitine). With the advent of improved synthesis and separation techniques, spurred by the FDA ban resultant to adverse events associated with use of the racemate (e.g. myopathy, muscle fatigue [similar to that now seen in some individuals on statin drug therapy]; e.g. Keith RE. JAMA, 1986), only the L-isomer is available, with the D-isomer (if found in commercial L-carnitine supplies) being present in trace quantities that have yet to be shown to be biologically undesirable in vivo.

    The specificity and sensitivity of certain chromatographic columns and techniques to discriminate between different isomers of bioactive molecules is remarkable. An isomer is defined as a chemical that has the same formula but one or more of the atoms comprising the compound differ in how it/they is/are attached. For example, amino acids (including carnitine) can exist in one of two forms (L- or D-isomer), which are mirror images of each other (like a left- and right-handed glove) and are thus called enantiomers (enanti-, opposite, Greek).

    One bioactive agent that has an enantiomerically-specific evidence base is the non-protein amino acid L-theanine. This relative of L-glutamine is present in abundance within all tea derived from Camellia sinensis leaves, not just green tea. Likely in response to the animal and human evidence base indicating that L-theanine has "relaxing" effects, an abundance of supply sources have emerged. In a recent study sponsored by Taiyo Kagaku, a Japanese concern that markets a patented and enzymatically produced L-theanine, Dr. Dan Armstrong at Iowa State University examined the enantiomeric profile of various commercially available "L-theanine" ingredients. Dr. Armstrong's lab previously published the only study to date examining the absolute theanine content of various teas, and their enantiomeric profiles (J Agric Food Chem, 1997). In the current study, his lab found (using an HPLC column containing a specific molecule that can "discriminate" between the L- and D- forms) that all of the ingredients ostensibly labeled as the L- isomer were indeed racemates, comprised of nearly 50-50 mixtures of L- and D-theanine enantiomers. Moreover, one of the "L-theanine" ingredients claimed to be derived from extraction of green tea. The enzymatically produced L-theanine ingredient offered by Taiyo indeed proved to be comprised solely of the L- enantiomer.

    The 1997 paper by Dr. Armstrong and his colleagues also found that very prolonged (tens of hours) "brewing" of tea leaves led to incremental "racemization" of L-theanine into D-theanine. This suggests that the chemical processing steps needed to synthetically produce L-theanine, or those required to extract pure L-theanine from tea biomass (if not cost-prohibitive) result in racemization. "Biologically conservative" methods like enzymatic synthesis are inherently stereoselective, yielding only one enantiomer/isomer, like that seen with methods of industrial production of L-carnitine and d-biotin. Chemical synthesis almost invariably lacks the stereo-discriminating power of enzymatic or biofermentation methods and thus can yield a racemate or disproportionate mix of isomers.

    Perhaps the greater question related to "quality" is the biological fate of the D-isomer. As described previously, supplementation with a racemate of carnitine can have adverse effects, which may mimic actual deficiency of carnitine, perhaps via the enantiomers competing for transport into cells (Watanabe S. Jpn Heart J, 1995). Given that the brain is very stereoselective for its "action" molecules, the impact of a racemate of theanine would be expected to have differing bioactivity. Moreover, the safety of a racemate, and of D-theanine is completely unexplored. Quality here is defined in 3-D, not just by the chemical fingerprint but also from which hand, the right or the left. A handprint.


    Whole Body Biology: The Platinum Quality Standard



    An innovative bakery opens downtown, to much fanfare and curiosity, claiming the highest QUALITY ingredients, obtained from exclusive sources. The elaborate assembly line of blenders, costly ovens and highly skilled bakers claims to produce the exact same product each time, derived from top secret, "old world" recipes. Eschewing a sampling program but favoring 50% off discounts on each purchase of bread, hundreds of loaves are sold the first day. After the initial buzz recedes, the owner/baker is dismayed by the very low sales. Worried, he himself engages in a sampling program on the sidewalk in front of his store. Lovely bread pieces in perfect cube shape are laid out on a silver platter, outstretched by his floured wrists. After a countless number of courteous declines he has one taker, who samples several pieces. After a seemingly inexorable wait the baker asks the woman, "What do you think? Is it not the highest quality bread you have ever tasted?!" "When you first opened I bought one loaf of your Cracked Up Wheat," she uttered. "A week later I bought another loaf. And then last week I bought a third loaf. They all looked, smelled, tasted, felt and even crumbled the same," she replied. "Yes, YES?" pushed the baker. "The quality of your product is remarkable, I must say," she continued. "It is as if you are cloning bread under the tutelage of the Rowett Institute [cloners of Dolly the Sheep]. But one thing was missing-they all tasted like sour sawdust. I buy bread for taste and that's how I define quality." Biology and physiology-the fascinating amalgam of sensory organs in the mouth and nose, the brain, and the nerve superhighway that connects them, a.k.a. taste sensation-overwhelm chemistry and compositional uniformity.

    Imagine a chemoprofile paragon-let's call it Ocu-Aqua, an ultra-high quality"functional water." It boasts a proprietary marigold extract (providing 5 mg of lutein + 0.5 mg of zeaxanthin from a 5% lutein + zeaxanthin extract) and a proprietary lychee fruit extract (contributing an additional 3 mg of zeaxanthin from a 6% zeaxanthin extract). Let's say it meets label claim for all the carotenoids. Its direct competitor-let's call it Ocu-Vitae-uses its own and different proprietary marigold and lychee fruit extracts, yet bearing identical lutein and zeaxanthin profiles (even the enantiomer profiles are identical-yes, these carotenoids live in stereo). Given the eye health promise that these two carotenoids offer, the National Eye Institute funds a study comparing the two using a new non-invasive device that can objectively measure visual acuity. A randomized, placebo-controlled, double-blind study is conducted with 270 subjects. Independent lab analysis confirms the identical lutein and zeaxanthin profiles of each product (and the absence of both from the placebo). However, subjects in the Ocu-Vitae group show a 46.2% greater improvement above that of the Ocu-Aqua group, a statistically significantly difference; the Ocu-Aqua group fares no better than the placebo group.

    Here the chemoprofile undertaken bears no relevance to the biological results. The heteromolecular composition of the two extracts-the marigold and lycii (lychee) fruit-is obscured by the myopic focus on but two chemical constituents. However, these extracts are comprised of a myriad of bioactives, hence the 5% and 6% by weight designations. Can one make a logic-based argument that the balance, the 94 or 95% NOT chemoprofiled in each of the proprietary extracts, is chemically identical by both presence and quantity? Nobody can from a position of logic and evidence. With near axiomatic conviction, no two heteromolecular entities claiming to be identical are indeed entirely identical.

    In the drug world chemical equivalence is a short cut to approval of a generic version of a pioneer drug but here we are dealing with PURE, single molecules, including stereospecificity (e.g. Prilosec [a racemate!] and omeprazole). Perhaps the best illustration of this is a study wherein three different Ginkgo biloba extracts, all sporting 24% flavonglycosides/6% terpenes, were compared in humans after oral dosing, using a specialized brain physiology assessment test (Itil T & Martorano D. Psychopharmacol Bull, 1995). Only one of the three extracts (the only one shown to have efficacy in Alzheimer's disease) elicited substantial brain physiology changes. Here partial chemical equivalence (some would argue identical chemoequivalence) yields differing biological responses.

    Bioequivalency in humans has NEVER been rigorously demonstrated between two different "natural bioactive" heteromolecular compositions claiming to be chemically equivalent. I posit that the innovator company, if through financially independent and rigorous systematic investigations shows their heteromolecular-containing product or ingredient (e.g. botanical extract, colostrum, aquaculture, bee propolis extract, etc.) to exhibit significant, desirable and consumer-relevant efficacy (and safety/tolerability) in humans after chronic oral dosing, can enter a realm where very few companies coexist. If they can also produce/have produced a product/ingredient identical or nearly identical to that used in the clinical trial(s), and they can potently market this "package," they have an intellectual property suite (even sans patent(s)) that can generate hundreds of millions of revenue dollars. Chemoprofiling here is a means to an end and the tool to assure reproducibility of efficacy and safety.NW


    About the author:
    Anthony Almada is president and chief scientific officer of IMAGINutrition, Laguna Niguel, CA. He can be reached at 949-363-5858; Fax: 949-363-1758; E-mail: anthony@imaginutrition.com; Website: www.imaginutrition.com.

    Disclosure: Mr. Almada of IMAGINutrition is a paid consultant to Taiyo International, marketers of Suntheanine brand of L-theanine and to Lonza U.S., manufacturers and marketers of L-Carnipure brand of L-carnitine.
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