fucoxanthin

Carotenoids are pigments produced by plants and algae and play a role in light harvesting as part of the photosynthesis process. Xanthophylls are a subset of carotenoids, identified by the fact that they are oxygenated either as hydroxyl groups or as epoxide bridges. This makes them more water soluble than carotenes such as beta-carotene. Fucoxanthin is a xanthophyll that contributes more than 10% of the estimated total production of carotenoids in nature.{{cite journal | vauthors = Dembitsky VM, Maoka T | title = Allenic and cumulenic lipids | journal = Progress in Lipid Research | volume = 46 | issue = 6 | pages = 328–75 | date = November 2007 | pmid = 17765976 | doi = 10.1016/j.plipres.2007.07.001 }} It is an accessory pigment found in the chloroplasts of many brown macroalgae, such as Fucus spp., and the golden-brown unicellular microalgae, the diatoms. It absorbs blue and green light at bandwidth 450-540 nm, imparting a brownish-olive color to algae.

Fucoxanthin has a highly unique structure that contains both an epoxide bond and hydroxyl groups along with an allenic bond (two adjacent carbon-carbon double bonds) and a conjugated carbonyl group (carbon-oxygen double bond) in the polyene chain. All of these features provide fucoxanthin with powerful antioxidant activity.{{cite journal | vauthors = Hu T, Liu D, Chen Y, Wu J, Wang S | title = Antioxidant activity of sulfated polysaccharide fractions extracted from Undaria pinnitafida in vitro | journal = International Journal of Biological Macromolecules | volume = 46 | issue = 2 | pages = 193–8 | date = March 2010 | pmid = 20025899 | doi = 10.1016/j.ijbiomac.2009.12.004 }}

In macroalgal plastids, fucoxanthin acts like an antenna for light harvesting and energy transfer in the photosystem light harvesting complexes.{{cite journal | vauthors = Owens TG, Wold ER | title = Light-Harvesting Function in the Diatom Phaeodactylum tricornutum: I. Isolation and Characterization of Pigment-Protein Complexes | journal = Plant Physiology | volume = 80 | issue = 3 | pages = 732–8 | date = March 1986 | pmid = 16664694 | pmc = 1075192 | doi=10.1104/pp.80.3.732}} In diatoms like Phaeodactylum tricornutum, fucoxanthin is protein-bound along with chlorophyll to form a light harvesting protein complex.{{cite journal | vauthors = Guglielmi G, Lavaud J, Rousseau B, Etienne AL, Houmard J, Ruban AV | title = The light-harvesting antenna of the diatom Phaeodactylum tricornutum. Evidence for a diadinoxanthin-binding subcomplex | journal = The FEBS Journal | volume = 272 | issue = 17 | pages = 4339–48 | date = September 2005 | pmid = 16128804 | doi = 10.1111/j.1742-4658.2005.04846.x | url = https://hal.archives-ouvertes.fr/hal-01094626/file/Guglielmi_FEBS-J_Modif.pdf | doi-access = free }} Fucoxanthin is the dominant carotenoid, responsible for up to 60% of the energy transfer to chlorophyll a in diatoms {{cite journal | vauthors = Papagiannakis E, van Stokkum IH, Fey H, Büchel C, van Grondelle R | title = Spectroscopic characterization of the excitation energy transfer in the fucoxanthin-chlorophyll protein of diatoms | journal = Photosynthesis Research | volume = 86 | issue = 1–2 | pages = 241–50 | date = November 2005 | pmid = 16172942 | doi = 10.1007/s11120-005-1003-8 }} When bound to protein, the absorption spectrum of fucoxanthin expands from 450-540 nm to 390-580 nm, a range that is useful in aquatic environments.{{cite journal | vauthors = Premvardhan L, Sandberg DJ, Fey H, Birge RR, Büchel C, van Grondelle R | title = The charge-transfer properties of the S2 state of fucoxanthin in solution and in fucoxanthin chlorophyll-a/c2 protein (FCP) based on stark spectroscopy and molecular-orbital theory | journal = The Journal of Physical Chemistry B | volume = 112 | issue = 37 | pages = 11838–53 | date = September 2008 | pmid = 18722413 | pmc = 2844098 | doi = 10.1021/jp802689p }}

Fucoxanthin is present in brown seaweeds and diatoms and was first isolated from Fucus, Dictyota, and Laminaria by Willstätter and Page in 1914.{{cite journal | vauthors = Peng J, Yuan JP, Wu CF, Wang JH | title = Fucoxanthin, a marine carotenoid present in brown seaweeds and diatoms: metabolism and bioactivities relevant to human health | journal = Marine Drugs | volume = 9 | issue = 10 | pages = 1806–28 | date = 2011-10-10 | pmid = 22072997 | pmc = 3210606 | doi = 10.3390/md9101806 | doi-access = free }} Seaweeds are commonly consumed in south-east Asia and certain countries in Europe, while diatoms are single-cell planktonic microalgae characterized by a golden-brown color, due to their high content of fucoxanthin. Generally, diatoms contain up to 4 times more fucoxanthin than seaweed, making diatoms a viable source for fucoxanthin industrially.{{cite journal | vauthors = Wang LJ, Fan Y, Parsons RL, Hu GR, Zhang PY, Li FL | title = A Rapid Method for the Determination of Fucoxanthin in Diatom | journal = Marine Drugs | volume = 16 | issue = 1 | pages = 33 | date = January 2018 | pmid = 29361768 | pmc = 5793081 | doi = 10.3390/md16010033 | doi-access = free }} Diatoms can be grown in controlled environments (such as photobioreactors). Brown seaweeds are mostly grown in the open sea, often exposed to metals and metalloids.{{cite journal | vauthors = Li H, Ji H, Shi C, Gao Y, Zhang Y, Xu X, Ding H, Tang L, Xing Y | title = Distribution of heavy metals and metalloids in bulk and particle size fractions of soils from coal-mine brownfield and implications on human health | journal = Chemosphere | volume = 172 | pages = 505–515 | date = April 2017 | pmid = 28104559 | doi = 10.1016/j.chemosphere.2017.01.021 }}

Limited studies of fucoxanthin in humans indicate low bioavailability.

• Chlorophyll

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{{Carotenoids}}

Category:Carotenoids

Category:Epoxides

Category:Brown algae

Category:Diatom biology

Category:Cumulated dienes