The chemical structure of cryptoxanthin

Xanthophylls (originally phylloxanthins) are yellow pigments from the carotenoid group. Their molecular structure is based on carotenes; contrary to the carotenes, some hydrogen atoms are substituted by hydroxyl groups and/or some pairs of hydrogen atoms are substituted by oxygen atoms. They are found in the leaves of most plants and are synthesized within the plastids. They are involved in photosynthesis along with green chlorophyll, which typically covers up the yellow except in autumn, when the chlorophyll is denatured by the cold.

In plants, xanthophylls are considered accessory pigments, along with anthocyanins, carotenes, and sometimes phycobiliproteins. Xanthophylls, along with carotenic pigments are seen when leaves turn orange in the autumn season.

Animals cannot produce xanthophylls, and thus xanthophylls found in animals (e.g. in the eye) come from their food intake. The yellow color of chicken egg yolks also comes from ingested xanthophylls.

Xanthophylls are oxidized derivatives of carotenes. They contain hydroxyl groups and are more polar than carotenes; therefore, carotenes travel further than xanthophylls in paper chromatography.

The group of xanthophylls includes lutein, zeaxanthin, neoxanthin, violaxanthin, and α- and β-cryptoxanthin.

Xanthophyll has a chemical formula of C₄₀H₅₆O₂.

Xanthophyll cycle

The xanthophyll cycle involves the enzymatic removal of epoxy groups from xanthophylls (e.g. violaxanthin, antheraxanthin, diadinoxanthin) to create so-called de-epoxidised xanthophylls (e.g. diatoxanthin, zeaxanthin). These enzymatic cycles were found to play a key role in stimulating energy dissipation within light harvesting antenna proteins by non-photochemical quenching- a mechanism to reduce the amount of energy that reaches the photosynthetic reaction centers. Non-photochemical quenching is one of the main ways of protecting against photoinhibition.¹ In higher plants there are three carotenoid pigments that are active in the xanthophyll cycle: violaxanthin, antheraxanthin and zeaxanthin. During light stress violaxanthin is converted to zeaxanthin via the intermediate antheraxanthin, which plays a direct photoprotective role acting as a lipid-protective anti-oxidant and by stimulating non-photochemical quenching within light harvesting proteins. This conversion of violaxanthin to zeaxanthin is done by the enzyme violaxanthin de-epoxidase, while the reverse reaction is performed by zeaxanthin epoxidase²

In diatoms and dinoflagellates the xanthophyll cycle consists of the pigment diadinoxanthin, which is transformed into diatoxanthin (diatoms) or dinoxanthin (dinoflagellates), at high light. ³

References

1. ^ Falkowski, P. G. & J. A. Raven, 1997, Aquatic photosynthesis. Blackwell Science, 375 pp
2. ^ Taiz, Lincoln and Eduardo Zeiger. 2006. Plant Physiology. Sunderland, MA: Sinauer Associates, Inc. Publishers, Fourth edition, 764 pp
3. ^ Jeffrey, S. W. & M. Vesk, 1997. Introduction to marine phytoplankton and their pigment signatures. In Jeffrey, S. W., R. F. C. Mantoura & S. W. Wright (eds.), Phytoplankton pigments in oceanography, pp 37-84. – UNESCO Publishing, Paris.

• Demmig-Adams, B & W. W. Adams, 2006. Photoprotection in an ecological context: the remarkable complexity of thermal energy dissipation, New Phytologist, 172: 11–21.

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• MeSH Xanthophylls