Tyrosine, wine

Phenylalanine and tyrosine also give rise to many commercially significant natural products, including the tannins that inhibit oxidation in wines alkaloids such as morphine, which have potent physiological effects and the flavoring of cinnamon oil (Fig. 22-28b), nutmeg, cloves, vanilla, cayenne pepper, and other products. 

Among the materials which may be dangerous in combination with MAO inhibitors are sedatives, tranquilizers, antihistamines, narcotics, and alcohol -- any of which can cause hypotensive crisis (severe blood pressure drop) and amphetamines (even diet pills), mescaline, asarone, nutmeg (active doses), macromerine, ephedrine oils of dill, parsely or wild fennel beer, wine, cocoa, aged cheeses, and other tyrosine-containing foods (tyrosine is converted into tyramine by bacteria in the bowel) -- any of which can cause hypotensive or hypertensive (severe blood pressure rise) crises. 

Tyramine [teye ra meen] is not a clinically useful drug, but it is found in fermented foods, such as ripe cheese and Chianti wine (see MAO inhibitors, p. 123). It is a normal by-product of tyrosine metabolism. Normally, it is oxidized by MAO, but if the patient is taking MAO inhibitors, it can precipitate serious vasopressor episodes. Like amphetamine, tyramine can enter the nerve terminal and displace stored norepinephrine. The released catecholamine acts on adrenoceptors. 

Tyrosine decarboxylase (EC.4.1.1.25), responsible for the production of tyramine from tyrosine, was first investigated in a wine lactic acid bacteria by... 

Moreno-Arribas and Lonvaud-Funel (1999). Moreno-Arribas et al. (2000) isolated and identified a number of tyramine-producing lactic acid bacteria in wine that had undergone malolactic fermentation all belonging to the lactobacilli. Tyrosine decarboxylase was then purified (Moreno-Arribas and Lonvaud-Funel 2001) and the corresponding gene was purified and sequenced (Lucas and Lonvaud-Funel 2002 Lucas et al. 2003). As far as the literature suggests, no tyramine-producing 0. oeni strain has yet been reported, with the exception of one strain (O. oeni DSM 2025) that was shown to be able to produce tyramine in a laboratory medium (Choudhury etal. 1990). 

Moreno-Arribas, V. Lonvaud-Funel, A. (1999). Tyrosine decarboxylase activity of Lactobacillus brevis lOEB 9809 isolated from wine and L. brevis ATCC 367. FEMS Microbiol. Lett., 180, 55-60. 

Peptides are commonly detected by absorbance at 200-220 nm. However, most of the compounds present in wine may interfere in the ultraviolet detection of peptides when low wavelengths are used. Thus, for the analysis of these compounds it is useful to apply sensitive and selective detection methods. To this end, it is possible to form derivates of the peptides that can be detected at higher and more specific wavelengths. Detection by fluorescence can also be used to detect peptides containing fluorescence amino acids (tyrosine and tryptophan). For peptides without this property, the formation of derivates with derivatizing agents have been proved to be very useful (Moreno-Arribas et al. 1998a). 

It is interesting to note that aspartic acid and/or asparagine and glutamic acid and/or glutamine form part of the peptides of all the wine fractions of different studies, independently of the type of wine or the analytical methodology employed in the analysis. Serine, threonine, alanine and glycine appear in most of the fractions studied while, lysine, tyrosine, valine, leucine, histidine and isoleucine has been found in a minor extent in these fractions. 

There are not many wine peptide sequences described in the literature. Table 6B.3 shows those that have been described. It can also be seen that in peptides with 2-10 amino acids, the amino acids that appear most frequently are tyrosine, proline, and isoleucine. 

NE secretion can be effectively decreased by administration of reseipine, an alkaloid isolated from a small woody perennial found in India (Rauwolfia), which has a high affinity for the vesicular monoamine h ansporter-2 (VMAT-2) and as such prevents NE storage. Alternatively, NE secretion can be increased by administration of tyramine (decarboxylated tyrosine), which is a constituent of a variety of foods including red wine, pickled herring and cheese. Amphetamine has a similar effect, which is most prominently manifested in the CNS. The termination of NE effects can be circumvented by the administration of cocaine, which blocks NE transport into presynaptic nerve endings (NET) an effect, which is also shared by some of the first generation antidepressants, such as imipramine. 

Tyrosine can be decarboxylated to tyramine by aromatic L-amino acid decarboxylase of intestinal bacteria. Tyramine, which is present in large amounts in certain foods (e.g., aged cheeses, red wines), is converted by monoamine oxidase (MAO) to the aldehyde derivatives. However, individuals who are receiving MAO inhibitors for the treatment of depression can accumulate high levels of tyramine, causing release of norepinephrine from sympathetic nerve endings and of epinephrine from the adrenal medulla. This results in peripheral vasoconstriction and increased cardiac output, which lead to hypertensive crises that can cause headaches, palpitations, subdural hemorrhage, stroke, or myocardial infarction. 

Foods containing tyramine (e.g., wine, cheese) and amino acids such as tyrosine and tryptophan... 

Tyrosol (Figure 6.5) or j9-hydroxy-phenyl-ethyl alcohol may be included in this group of compounds (Ribereau-Gayon and Sapis, 1965). It is always present in both red and white wine (20-30 mg/1) and is formed during alcoholic fermentation from tyrosine (j -hydroxyphenyl-alanine), in turn synthesized by yeast. This compound, which remains at relatively constant concentrations throughout aging, is accompanied by other non-phenolic alcohols like tryptophol (0-1 mg/1) and phenyl-ethyl alcohol (10-75 mg/1). 

The aromatic BA, tyramine and (3-phenylethylamine are prodnced, respectively, by decarboxylation of tyrosine and phenylalanine by the enzyme tyrosine decarboxylase (TDC) (Landete, De las Rivas, Marcobal, Munoz, 2007 Pessione et al, 2009). TDC was purified from the strain L brevis lOEB 9809 isolated from wine (Moreno-Arribas Lonvaud-Funel, 2001 Russo et al, 2012). Lucas and Lonvaud-Funel (2002) described that in L. brevis lOEB 9809, the tyramine biosynthetic pathway is encoded by a cluster of four genes (Figure 12.2). All strains carrying the TDC cluster produce both tyramine and 3-phenylethylamine, but the levels of the latter are four to... 

Using this procedure. Red wine et al. obtained an upper limit for the temperature of 10-16 K for their 22-pole ion trap, consistent with what we measured in our 22-pole trap [46] as well as in a newly constructed cold octupole trap. In contrast, the 3-D quadrupole ion trap employed by Choi et al. attained temperatures of 45-54 K for protonated tyrosine [138], which is likely to reflect RF heating of the ions. 

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