Aminosaurs, Biological Pigments, Bugs, Cattle, Tryptophan
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Ommochrome (visual pigment) and Kynurenine (a metabolite of the amino acid l-tryptophan used in the production of niacin)

Ommochrome (or visual pigment) refers to several biological pigments that occur in the eyes of crustaceans and insects. The eye color is determined by the ommochromes. Ommochromes are also found in the chromatophores of cephalopods, and in spiders.

Ommochromes are metabolites of tryptophan, via kynurenine and 3-hydroxykynurenine. They are responsible for a wide variety of colors, ranging from yellow over red and brown to black. Lighter colors tend to be generated by ommatins, while mixtures of ommatin and ommins are responsible for darker colors.

In spiders, ommochromes are usually deposited as pigment granules within the cells of the hypodermis, immediately beneath the cuticle.

A study on various insects showed that ommochromes in their eyes have high antioxidant activity. The ommochromes were found to have the ability to suppress the Maillard reaction.

The Kynurenine pathway, which connects quinolinic acid to tryptophan. The pathway is named for the first intermediate, kynurenine, which is a precursor to kynurenic acid and 3-hydroxykynurenine.

3-Hydroxykynurenine is a metabolite of tryptophan, which filters UV light in the human lens. It is one of two pigments identified as responsible for the goldenrod crab spider‘s (Misumena vatia) yellow coloration.

l-Kynurenine is a metabolite of the amino acid l-tryptophan used in the production of niacin.

Kynurenine is synthesized by the enzyme tryptophan dioxygenase, which is made primarily but not exclusively in the liver, and indoleamine 2,3-dioxygenase, which is made in many tissues in response to immune activation.

Kynurenine and its further breakdown products carry out diverse biological functions, including dilating blood vessels during inflammation and regulating the immune response.

Some cancers increase kynurenine production, which increases tumor growth.

Evidence suggests that increased kynurenine production may precipitate depressive symptoms associated with interferon treatment for hepatitis C.

Cognitive deficits in schizophrenia are associated with imbalances in the enzymes that break down kynurenine.

Blood levels of kynurenine are reduced in people with bipolar disorder.

  • Bartoli, F; Misiak, B; Callovini, T; Cavaleri, D; Cioni, RM; Crocamo, C; Savitz, JB; Carrà, G (19 October 2020). “The kynurenine pathway in bipolar disorder: a meta-analysis on the peripheral blood levels of tryptophan and related metabolites”. Molecular Psychiatry. 26 (7): 3419–3429. doi:10.1038/s41380-020-00913-1. PMID 33077852. S2CID 224314102.

Kynurenine production is increased in Alzheimer’s disease and cardiovascular disease where its metabolites are associated with cognitive deficits and depressive symptoms.

  • Guillemin GJ, Brew BJ, Noonan CE, Takikawa O, Cullen KM (2005). “Indoleamine 2,3 dioxygenase and quinolinic acid Immunoreactivity in Alzheimer’s disease hippocampus”. Neuropathology and Applied Neurobiology. 31 (4): 395–404. doi:10.1111/j.1365-2990.2005.00655.x. PMID 16008823. S2CID 7754894.
  • Wirleitner B, Rudzite V, Neurauter G, Murr C, Kalnins U, Erglis A, Trusinskis K, Fuchs D (2003). “Immune activation and degradation of tryptophan in coronary heart disease”. European Journal of Clinical Investigation. 33 (7): 550–4. doi:10.1046/j.1365-2362.2003.01186.x. PMID 12814390. S2CID 10300941.
  • Gulaj E, Pawlak K, Bien B, Pawlak D (2010). “Kynurenine and its metabolites in Alzheimer’s disease patients”. Advances in Medical Sciences. 55 (2): 204–11. doi:10.2478/v10039-010-0023-6. PMID 20639188.
  • Swardfager W, Herrmann N, Dowlati Y, Oh PI, Kiss A, Walker SE, Lanctôt KL (2009). “Indoleamine 2,3-dioxygenase activation and depressive symptoms in patients with coronary artery disease”. Psychoneuroendocrinology. 34 (10): 1560–6. doi:10.1016/j.psyneuen.2009.05.019. PMID 19540675. S2CID 36687413.

Kynurenine is also associated with tics.

Kynureninase catabolizes the conversion of kynurenine into anthranilic acid while kynurenine-oxoglutarate transaminase catabolizes its conversion into kynurenic acid. Kynurenine 3-hydroxylase converts kynurenine to 3-hydroxykynurenine.

Kynurenine has also been identified as one of two compounds that makes up the pigment that gives the goldenrod crab spider its yellow color.

Kynurenine pathway dysfunction

Dysfunctional states of distinct steps of the kynurenine pathway (such as kynurenine, kynurenic acid, quinolinic acid, anthranilic acid, 3-hydroxykynurenine) have been described for a number of disorders, including:

Downregulation of kynurenine-3-monooxygenase (KMO) can be caused by genetic polymorphisms, cytokines, or both.

KMO deficiency leads to an accumulation of kynurenine and to a shift within the tryptophan metabolic pathway towards kynurenine acid and anthranilic acid.

Kynurenine-3-monooxygenase deficiency is associated with disorders of the brain (e.g. major depressive disorder, bipolar disorder, schizophrenia, tic disorders) and of the liver.

See also

References

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