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PubMed1991

Physiological role of 3-hydroxykynurenine and xanthurenic acid upon crustacean molting.

Studies with crabs (Charybdis japonica) and crayfish (Procambarus clarkii) revealed that the tryptophan metabolites, 3-hydroxy-L-kynurenine (3-OH-K) and xanthurenic acid (XA), common secretory products of the X-organ-sinus gland complex of eyestalks from several decapods, regulated the molting of crustaceans in species-nonspecific fashion. Injection of 3-OH-K to the eyestalk-ablated crayfish delayed the onset of the first molt and lengthened the interval between the first and second molts. These lines of evidence were in accord with previous accounts of the so-called "molt inhibiting hormone" (MIH) effect. Removal of eyestalks caused a change in the conversion capacity of exogenous 3-OH-K to XA in the hemolymph. The peak in transformation capacity was followed by a peak in the titer of 20-hydroxyecdysone or molting hormone. Moreover, the seasonal profiles of the XA and ecdysone titers in Charybdis japonica exhibited a staggered relationship in the tissues tested. The ratio of XA to 3-OH-K, which is expected to indicate the apparent 3-OH-Kase activity, fluctuated seasonally and locally. When the Y-organ with the adhering tissues (Y-organ complex or YOC) was incubated during the period of high XA titer, the YOC produced 100 times more ecdysone than before incubation. It is suggested that ecdysteroidogenesis in situ was suppressed during this period by XA, but incubation of the YOC lead to a dramatic acceleration in ecdysone synthesis by overriding this inhibitory effect. XA profoundly repressed ecdysteroidogenesis in the YOC culture. Thus, XA is the ecdysone biosynthesis inhibitor (EBI) and 3-OH-K the precursor in crustaceans. An interfering effect of XA to a biocatalyst cytochrome P-450 system was postulated for the inhibition mechanism of ecdysteroidogenesis.

Animals↗
PubMed2006

The effects of blood feeding and exogenous supply of tryptophan on the quantities of xanthurenic acid in the salivary glands of Anopheles stephensi (Diptera: Culicidae).

Xanthurenic acid (XA), produced as a byproduct during the biosynthesis of insect eye pigment (ommochromes), is a strong inducer of Plasmodium gametogenesis at very low concentrations. In previous studies, it was shown that XA is present in Anopheles stephensi (Diptera: Culicidae) mosquito salivary glands and that during blood feeding the mosquitoes ingested their own saliva into the midgut. Considering these two facts together, it is therefore likely that XA is discharged with saliva during blood feeding and is swallowed into the midgut where it exerts its effect on Plasmodium gametocytes. However, the quantities of XA in the salivary glands and midgut are unknown. In this study, we used high performance liquid chromatography with electrochemical detection to detect and quantify XA in the salivary glands and midgut. Based on the results of this study, we found 0.28+/-0.05 ng of XA in the salivary glands of the mosquitoes, accounting for 10% of the total XA content in the mosquito whole body. The amounts of XA in the salivary glands reduced to 0.13+/-0.06 ng after mosquitoes ingested a blood meal. Approximately 0.05+/-0.01 ng of XA was detected in the midgut of nonblood fed An. stephensi mosquitoes. By adding synthetic tryptophan as a source of XA into larval rearing water (2 mM) or in sugar meals (10 mM), we evaluated whether XA levels in the mosquito (salivary glands, midgut, and whole body) were boosted and the subsequent effect on infectivity of Plasmodium berghei in the treated mosquito groups. A female specific increase in XA content was observed in the whole body and in the midgut of mosquito groups where tryptophan was added either in the larval water or sugar meals. However, XA in the salivary glands was not affected by tryptophan addition to larval water, and surprisingly it reduced when tryptophan was added to sugar meals. The P. berghei oocyst loads in the mosquito midguts were lower in mosquitoes fed tryptophan treated sugar meals than in mosquitoes reared on tryptophan treated larval water. Our results suggest that mosquito nutrition may have a significant impact on whole body and midgut XA levels in mosquitoes. We discuss the observed parasite infectivity results in relation to XA's relationship with malaria parasite development in mosquitoes.

Animals↗
PubMed2006

The tryptophan oxidation pathway in mosquitoes with emphasis on xanthurenic acid biosynthesis.

Oxidation of tryptophan to kynurenine and 3-hydroxykynurenine (3-HK) is the major catabolic pathway in mosquitoes. However, 3-HK is oxidized easily under physiological conditions, resulting in the production of reactive radical species. To overcome this problem, mosquitoes have developed an efficient mechanism to prevent 3-HK from accumulating by converting this chemically reactive compound to the chemically stable xanthurenic acid. Interestingly, 3-HK is a precursor for the production of compound eye pigments during the pupal and early adult stages; consequently, mosquitoes need to preserve and transport 3-HK for compound eye pigmentation in pupae and adults. This review summarizes the tryptophan oxidation pathway, compares and contrasts the mosquito tryptophan oxidation pathway with other model species, and discusses possible driving forces leading to the functional adaptation and evolution of enzymes involved in the mosquito tryptophan oxidation pathway.

Alanine Transaminase↗
PubMed2001

Both mosquito-derived xanthurenic acid and a host blood-derived factor regulate gametogenesis of Plasmodium in the midgut of the mosquito.

Gametogenesis of Plasmodium in vitro can be induced by the combined stimulus of a 5 degrees C fall in temperature and the presence of xanthurenic acid (XA). In-vitro experiments showed that P. gallinaceum (EC(50)=80 nM) is much more sensitive to XA than P. berghei (9 microM), P. yoelii (8 microM), and P. falciparum (2 microM). However, in the mosquito vector, we do not know whether the temperature shift and XA are the only gametocyte-activating factors (GAF), nor do we know with certainty the true source(s) of XA in the mosquito blood meal. Previous studies indicate that XA is the only source of GAF in the mosquito. By defining, and then contrasting, the ability of an XA-deficient mutant of Aedes aegypti, with the wild-type mosquito to support exflagellation and ookinete formation in vivo, we determined the roles of parasite-, mosquito- and host blood-derived GAF in the regulation of gametogenesis of P. gallinaceum. Removal of both host and vector sources of GAF totally inhibited both exflagellation and ookinete production, whilst the lack of either single source resulted in only a partial reduction of exflagellation and ookinete formation in the mosquito gut. Both sources can be effectively replaced/substituted by synthetic XA. This suggests (1) both mosquito- and vertebrate-derived factors act as GAF in the mosquito gut in vivo; (2) the parasite itself is unable to produce any significant GAF activity. Studies are underway to determine whether vertebrate-derived GAF is XA. These data may form the basis of further studies of the development of new methods of interrupting malarial transmission.

Aedes↗
PubMed1998

Xanthurenic acid induces gametogenesis in Plasmodium, the malaria parasite.

A small, heat stable chromophore extracted from mosquitoes has recently been implicated as the signal that induces mating of Plasmodium, the malaria parasite. We have used high resolution electrospray mass spectrometry to determine that this gamete activation factor (GAF) has a m/z = 205.0450, suggesting a molecular species composition of C10H7NO4. Xanthurenic acid (XA), a product of tryptophan catabolism, was determined to have an elemental composition, ultraviolet absorbance maxima, and mass spectrum consistent with those characteristics of GAF. XA activated gametogenesis of Plasmodium gallinaceum and P. falciparum in vitro at concentrations lower than 0.5 microM in saline buffered to pH 7.4. A structural analog of XA, kynurenic acid (C10H6NO3), also activated gametogenesis but only at higher concentrations and with less effect. We propose that XA is GAF. This is the first evidence that XA has induction activity.

Animals↗
PubMed1984

Quantitation of xanthurenic acid in rabbit serum using high performance liquid chromatography.

Xanthurenic acid (XA) has been quantified in the serum of normal and vitamin B6-deficient rabbits using high performance liquid chromatography. The concentration of XA in the serum of normal and B6-deficient rabbits was 141 and 2275 ng/ml, respectively. The coefficient of variation for a series of dilutions of standard XA (3.9 to 1000 ng) ranged from 45.5% at the lower limit of the curve to 10.9% at the higher range of the curve. The minimum detectable level was 3.9 ng/ml. Serum samples spiked with reference XA exhibited a parallel dose response. The percentage recovery of XA from serum samples was 80.8%. The procedure, which requires 1 to 2 ml of serum, is sensitive and may be a useful tool for assessing B6 nutritional parameters as well as the physiological role of XA. It offers advantages over urinary procedures because it is more sensitive, more specific, and allows the study of blood levels of XA.

Animals↗
PubMed1975

The physiological significance of the xanthurenic acid-insulin comples.

The xanthurenic acid-insulin complex was found to have similar immunological properties to native Zn-insulin. This complex showed less hormonal activity on glucose metabolism in adipose tissue than native An-insulin, but its activity was increased by addition of Zn2+ ions.

Adipose Tissue↗
PubMedDate not supplied

Kynurenic acid and xanthurenic acid excretion after tryptophan loading in actinic reticuloid.

The metabolism of L-tryptophan (TRP) before and after an oral loading dose of 20 mg/kg body weight was studied in three patients with actinic reticuloid (AR) and four healthy male volunteers. The preload mean plasma TRP concentrations and mean 24-hour urinary excretions of TRP in the AR group were significantly lower than in the control group. After oral TRP administration, plasma TRP concentrations increased normally in AR, thereby excluding defective intestinal absorption. The mean preload and postload excretions of kynurenic acid (KA), xanthurenic acid (XA), 5-hydroxyindoleacetic acid (5HIAA), and 3-indoleacetic acid (3IAA) were not significantly different between the two groups. We conclude that KA, which has been shown to have phototoxic properties in vitro, is not altered primarily in AR, and that the reported abnormalities of TRP metabolism are most likely the consequence of the severe photosensitivity in this disorder.

Aged↗
PubMed1994

Colorimetric determination of urinary xanthurenic acid using an oxidative coupling reaction with N,N-diethyl-p-phenylenediamine.

A simple enzymatic method for the spectrophotometric determination of xanthurenic acid (XA) in urine is described. The method is based on the formation of a pigment derived from an oxidative coupling reaction with XA and N,N-diethyl-p-phenylenediamine (DE-PPD) in the presence of hydrogen peroxide and horseradish peroxidase. The color of the reaction mixture was developed with a peak absorbance at 750 nm. The recoveries against XA added to urine ranged from 91.0 to 96.5%. With this method, XA can be determined within 5 min, without a time-consuming sample preparation. The detection range of this method was between 5 and 150 microM, with a coefficient of variation of 2.7% or less. The correlation between this and the fluorometric method was good.

Calibration↗
PubMed2000

Photochemical studies on xanthurenic acid .

The tryptophan metabolite xanthurenic acid (Xan) has been isolated from aged human cataractous lenses. The photophysical properties of Xan were examined to determine if it is a potential chromophore for age-related cataractogenesis. We found that Xan produces singlet oxygen (psi delta = 0.17 in CD3OD) with the same efficiency as the lenticular chromophore N-formyl kynurenine and quenches singlet oxygen at a rate similar (2.1 x 10(7); CD3OD) to other tryptophan metabolites found in the eye. As the mechanisms of induction of cataracts may also involve redox reactions, the interactions of hydrated electrons (e(aq)-), the azide radical (N3*) and hydroxyl radical (OH*) with Xan were studied using the technique of pulse radiolysis. The reaction rate constants of e(aq)-, N3* and OH* with Xan were found to be of the same order of magnitude as other tryptophan metabolites. The rate constant for reaction of Xan with e(aq)- solvated electrons was found to be diffusion controlled (k = 1.43 x 10(10) M(-1) s(-1); the reaction with N3* was very fast (k = 4.0 x 10(9) M(-1) s(-1)); and with OH* was also near diffusion controlled (k = 1.0 x 10(10) M(-1) s(-1)). Superoxide O2*- production by irradiated Xan in methanol was detected by electron paramagnetic resonance and substantiated by determining that the enhanced rate of oxygen consumption of Xan irradiated in the presence of furfuryl alcohol was lowered by superoxide dismutase.

Cataract↗
PubMed2001

Photooxidation of lens proteins with xanthurenic acid: a putative chromophore for cataractogenesis.

The tryptophan metabolite, xanthurenic acid (Xan), is produced through a transamination reaction in high concentrations in human lenses with age and has been isolated from aged human cataractous lenses. It has appreciable absorption between 300 and 400 nm (lambda max = 334 nm), the range absorbed by the human lens. Our recent studies have shown that unlike most tryptophan metabolites in the eye, Xan is photochemically active, producing both superoxide and singlet oxygen. To determine if Xan could act as a photosensitizer and photooxidize cytosolic lens proteins, alpha-, beta- and gamma-crystallins were irradiated (lambda > 300 nm, 12 mW/cm2) in the presence and absence of Xan. Upon irradiation and in the presence of Xan, lens proteins polymerized in the order alpha > beta > gamma as assessed by sodium dodecyl sulfate polyacrylamide gel electrophoresis. Further analysis of the photolyzed alpha-crystallin by mass spectrometry indicated that histidine, tryptophan and methionine residues were oxidized at specific positions in a dose-dependent (irradiation time) manner. In alpha A-crystallin two forms of oxidized histidine 154 were observed, 2-imidazolone and 2-oxohistidine. Our results suggest that naturally occurring Xan is a chromophore capable of photosensitization and photooxidation of lens proteins. Furthermore, this compound could play a role in age-related cataractogenesis.

Cataract↗
PubMed2002

Role of xanthurenic acid 8-O-beta-D-glucoside, a novel fluorophore that accumulates in the brunescent human eye lens.

We have been able to identify a blue fluorophore from the low-molecular weight soluble fraction of human adult nondiabetic brunescent cataract lenses as xanthurenic acid 8-O-beta-D-glucoside (XA8OG) (excitation = 338 nm and emission = 440 nm). To determine the role of this fluorophore in the lens, we have examined its photophysical and photodynamic properties. We found XA8OG to have a fluorescence quantum yield (phi) of 0.22 and a major emission lifetime of 12 ns. We found it to be a UVA-region sensitizer, capable of efficiently generating singlet oxygen species but little of superoxide. We also demonstrated that XA8OG oxidizes proteins when irradiated with UVA light, causing photodynamic covalent chemical damage to proteins. Its accumulation in the aging human lens (and the attendant decrease of its precursor O-beta-D-glucoside of 3-hydroxykynurenine) can, thus, add to the oxidative burden on the system. XA8OG, thus, appears to be an endogenous chromophore in the lens, which can act as a cataractogenic agent.

Electrophoresis, Polyacrylamide Gel↗
PubMed1975

Purification of xanthurenic acid-insuline complex.

Tritium labeled xanthurenic acid (XA)-insulin complexes A and B were obtained. These were shown to be one component by the disc electrophoresis, and bound XA was not liberated by the electrophoresis from the paper electrophoresis experiment. The result of the gel filtration showed that the molecular weight of the complex A and B was 24,000. But there is still a possibility that complex B might be contaminated with free insulin.

Chemical Phenomena↗
PubMedDate not supplied

The clinical significance of an elevated excretion of xanthurenic acid in psychiatric patients.

This study investigations whether the synthesis of nicotinamide out of L-tryptophan is disordered in depression or in anxiety. To this end the excretion of xanthurenic acid (XA) in 24 hours urine was measured after administration of an oral loading dose of 5 grams L-tryptophan. The subjects were depressive, anxious, and alcoholic patients, while other psychiatric patients, served as control group. Anxiety and not depression is the clinical correlate of an elevated excretion of XA. Liver disorder and vitamin B-6 deficiency have to be excluded. A psychiatric control group is necessary.

Adult↗
PubMedDate not supplied

Xanthurenic acid flow in 24-hour urine following L-tryptophan loading in depressive patients.

The xanthurenic acid (XA) flow in 24-hour urine following L-tryptophan loading was determined in a control group and in depressive patients divided into two DSM-III categories: minor depression (dysthymic disorder, atypical depression, adaptation disorder with depressive mood), and major depression. The XA flow is not significantly (p = 0.15) different in these categories of depression and in the control group. The number of patients with an abnormal XA flow (cut-off value greater than or equal to 106.8 mu mol/24 hours) is not significantly different among these groups (p = 0.40). The XA flow is therefore not relevant whether for depression or major depression. The XA flow in 24-hour urine following L-tryptophan loading decreases with age (p = 0.006) and increases with the 24-hour urinary output (p = 0.02). Women excrete significantly more XA (p = 0.02) than men. One must take age, 24-hour urinary output and sex into account for the interpretation of the XA data.

Adjustment Disorders↗
PubMed1984

[Determination of urinary xanthurenic acid after oral loading of L-tryptophan in 88 cases of photodermatosis].

Disturbances in the kynurenine pathway are present in pellagra and pellagroid syndromes. In 88 photodermatoses, the authors found increased urinary excretion of xanthurenic acid after oral load of tryptophan in a number of light-induced eruptions, i.e. benign summer photodermatosis (40%), polymorphous light eruptions (37%), and persistent light reactions (36%) as well as in patients with acute alcoholic intoxication. These biochemical abnormalities in the kynurenine pathway allow for a pathogenetic approach in some photodermatoses.

Administration, Oral↗
PubMed1984

Studies on the urinary excretion of xanthurenic acid in diabetics.

Xanthurenic acid (XA), kynurenic acid (KA) and creatinine in fasting urine were determined by reversed phase high pressure liquid chromatography in order to investigate the distortion of tryptophan metabolites in diabetes mellitus. The results of ten patients with non-insulin dependent diabetes mellitus and ten normal healthy subjects were compared. No tryptophan load test was performed in this study, because tryptophan loading produces further latent shortage of active vitamin B6 which results in exacerbation of the disease. The ratios of XA to KA and to creatinine were 0.35 +/- 0.099 (mean +/- S.D.) and 0.99 +/- 0.321 in the diabetic patients. The corresponding figures in the normal subjects were 0.17 +/- 0.064 and 0.55 +/- 0.22. Both ratios were significantly higher in the diabetic patients than in normal subjects (p less than 0.001 and p less than 0.01, respectively). This means that XA was excessively excreted in diabetic patients resulting in distortion of tryptophan metabolism. Our findings indicated that the ratios are useful to monitor excess XA excretion and also for detection of diabetes.

Adult↗