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L-Tryptophan 2008 368/L-THEANINE PDR FOR NUTRITIONAL SUPPLEMENTS Sugiyama T, Sadzuka' Y. Enhancing effects of green tea death. Pellagra is a vitamin B3 deficiency disease caused by components on the antitumor activity of adriamycin against dietary lack of niacin and protein, especially proteins M5076 ovarian carcinoma. Cancer Lef(. 1998; 133: 19-26 ... containing the essential amino acid L-tryptophan., Because Sugiyama T, Sadzuka Y. Theanine, a specific glutamate L-tryptophan can be converted into niacin, foods with L­ derivative in green tea, reduces the adverse reactions of tryptophan but without niacin, such as 'milk, prevent pellagra. doxorubicin by changing the glutathione level. Cancer Lett .. However, if dietary L-tryptophan is diverted into the 2004;212(2): 177 -184. production of protein, niacin deficiency may still exist, Sugiyama T, Sadzuka Y, Sonobe T: Theanine, a major amino leading to pell_agra. acid in green tea,' inhibits leukopenia and enhances antitumor activity induce by idarubicin. Proc Am Assoc Cancer Res. By the end of the 1980s, some millions of people, mainly 1999;40: \O(Abstract 63). ' women 'and mainly in the United States, were using Yamada T, Terashima T, Honma H, et al. Effects of theanine, supplemental, L-tryptophan for a variety of reasons-pre­ a unique amino acid in tea leaves, on memory in a rat menstrual sY!1drome (PMS), sleep disorders, anxiety, depres­ behavioral test.. Biosci Biotechnol Biochem. 2008;72(~): I ~56- sion, fibromyalgia, seasonal affective disorder (SAD) and 1359. ' chronic pain syndromes. Supplemental L-tryptophan was Yamada T, Terashima T, Kawano S, et al. Theanine, gamma­ also used ,as an adjunct in the treatment of cocaine, glutamylethyl~mide, a unique amino acid in tea leav~s, amphetamirie, alcohol and other drug abuse and for jet lag. modulates neurotransmitter concentrations in the brain striatum, In the context of the intensive 'care unit,' some physicians interstitium in conscious rats. Amino Acids. Epub: 2008 Jan 15. used it as a sedative to help relax their intensive c~e unit Yokogoshi H, Kato Y, Sages aka YM, et al. Reducti'on effect 'of patients with a substance that was less likely to suppress theanine on blood pressure and brain 5-hydroxyindoles in their respiration than a pharmaceutical sedative might. The spontaneous hypertensive rats. Biosci Biotechnol Biochem. physicians thought that this .was particularly useful for those 1995;59:615-618. patients who had compromised respiration to begin with. Yokogo~hi H, Kobayashi·M. Hypotensive effect of gamma­ In fact, there were even some clinical studies that appeared glutamylmethylamide in spontaneously hypertensive rats.' Life to support some of the above uses of L-tryptophan. Sci. 1998;62: 1065-1068. YokogoshiH, Kobaya~hi M; Mochizuki M, et ~i: Effect of In the fall of 1989, L-tryptophan supplementation was to see theanine, r-glutamylethylamide on brain monoillllines' and striatal its darkest days. In October 1989, Dr. Philip Herzman and dopamine release in conscious rats. Neurochem Res. his colleagues in New Mexico met to compare notes on three 1998;23:667-673. female patients with unusual clinical presentations involving myalgia (muscle pain), weakn'ess, oral ulcers, abdominal pain, skin rash and' a striking increase in eosinophils (a subset of white blood cells) in their blood. These physicians L-Tryptophan, recognized that all three patients developed these symptoms after using supplemental L-tryptophan, and they thought that DESCRIPTION L-tryptophan is one of the eight essential amino acids for the. supplementa!. L-tryptophan might have caused the problem. They r~ported the illnesses and their suspected humans (10 for children). It is the, least abundant essential as~ociation of the illnesses to supplemental L-tryptophan to amino acid. An essential af11ino acid is an amino acid that the the New Mexico Health and Environment Department and body can not make, or if it can, it does not make it in the CDC' (Centers for Disease Control and Prevention). The sufficient amounts for all of its biological needs, (for N'ew Mexico Health and Environmental Department discov­ example, L-histidine and L-arginine for children). L-trypto­ ered several similar cases, almost all of which involved phan is a protein amino acid, meaning that it isa building supplemental L-tryptophan. As awareness of the problem block of proteins. L-tryptophan also has other important grew-the CDC notified all state health departments about a functions. It is the precursor of the neurotransmitter seroto­ nin, the pineal gland hormone melatonin (see Melatonin), the health problem possibly due to ingestion of supplemental L~ possible neuroprotectant kynurenic acid, vitamin' B3 (niacin tryptophan-a number of cases were reported from other states. In November 1989, the CDC proposed the name of or nicotinic acid and niacinamide or nicotinamide), and the eosinophilia-myalgia syndrome, or EMS, for the disease, coenzymes NADH (nicotinamide adenine dinucleotide) and NADPH (nicotinamide adenine dinucleotide phosphate). since all the presumptive cases had both eosinophilia (elevation of eosinophils in their blood) and severe myalgia A deficiency of niacin and/or L-tryptophan causes pellagra~ (muscle pain). Since trichinosis also causes eosinophilia and which is characterized by the three Ds of dermatitis, diarrhea myalgia, the initial CDC surveillance definition of an EMS and dementia, and, if untreated for some time, a fourth D, case required serological testing or a muscle biopsy to rule 2008 SUPPLEMENT MONOGRAPHS L·TRYPTOPHAN 1369 out trichinosis. However, since the clinical presentation of its CAS Registry Number is 73-23-3. The minimum daily EMS was sufficiently distinct from trichinosis, the initial requirement for L-tryptophan is said to be 0.25 grams daily requirement of negative testing for trichinosis was dropped for males and 0.15 grams for females. The average Western from the surveillance defmition. diet contains about one to three grams daily. L-tryptophan is represented by the following chemical structure. The association between use of supplemental L-tryptophan and EMS was a strong one and on November 11, 1989, the FDA issued a nationwide warning advising consumers to discontinue the use of L-tryptophan supplements and subse­ quently requested a nationwide recall of all L-tryptophan products sold over-the-counter. With the removal of L­ tryptophan supplements from the marketplace, the number of reported new cases of EMS dropped rapidly. As of June 1993, 1,511 cases of EMS had been reported to the CDC, L-Tryptophan including 37 deaths. Although the preponderance of EMS cases came from the United States, 97 cases were reported ACTIONS AND PHARMACOLOGY from Germany, 24 from France, 16 from Canada, three each ACTIONS from Switzerland and Belgium, two each from the UK, and L-tryptophan may have antidepressant activIty, activity Japan and one each from Spain and Australia. In the United against premenstrual syndrome (PMS) and sleep-promoting States, 84% of the cases were women and 97% non-Hispanic activity. white, and the highest incidence of EMS cases was in the MECHANISM OF ACTION Western states. In terms of risk factors, the number one risk Antidepressant activity: A Cochrane Collaboration meta­ factor for EMS was the use of L-tryptophan supplements. analysis concluded that although a number of studies were The dose of supplemental L-tryptophan and the age of the performed to determine if L-tryptophan and 5-hydroxytryp­ user were also considered risk factors for EMS. Older users tophan (5-HT, see 5-Hydroxytryptophan) possessed antide­ of L-tryptophan were more likely to develop EMS than pressant activity, only a few were of sufficient quality to be younger users and the risk of developing EMS increased reliable. However, those few did suggest that both L­ with larger doses of L-tryptophan. A 50% attack rate was tryptophan and 5-hydroxytryptophan were better than place­ demonstrated in those who ingested more than four grams of bo at alleviating depression. The authors also stated that L-tryptophan on a regular basis, suggesting that the EMS "further studies are needed to evaluate the efficacy and agent was a toxicant safety of 5-HT and tryptophan before their widespread use The hunt for possible toxicants and contaminants in the can be recommended." The possible antidepressant effect is suspected L-tryptophan supplements that could be identified accounted for by the conversion of L-tryptophan and 5- as causing EMS immediately began, but, although some hydroxy tryptophan to the neurotransmitter serotonin. suspects were identified, none was positively identified that In a double-bind placebo-controlled trial of L-tryptophan could have caused EMS. combined with the selective serotonin reuptake inhibitor (SSRI) fluoxetine, it was found that combining 20 milli­ In 1991, the FDA banned L-tryptophan supplements from grams of fluoxetine with two to four grams of L-tryptophan sale in the U.S. In 2001, the FDA loosened the restriction on the marketing of L-tryptophan supplements, but did ban its daily for a group diagnosed with major depressive disorder importation except under certain circumstances. As of May produced a more rapid antidepressant effect when compared 2, 2005, the FDA completely cancelled the import ban alert with those patients who just used fluoxetine alone. The tryptophan group also seemed to have a protective effect on for L-tryptophan. Following this, L-tryptophan supplements began again appearing on the nutritional supplement market­ slow-wave sleep. The four gram per day dose of L-trypto­ phan, but not the two gram per day dose, produced daytime place, including in health food stores, compounding pharma­ drowsiness. Again, the mechanism of action of the L­ cies and over the Internet, where they continue to be found. tryptophan was most likely due to its conversion to the L-tryptophan is chemically described as (2S)-2-amino-3- neurotransmitter serotonin in the brain. (IH-indol-3-yl)propanoic acid.
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