Fucoxanthin

Fucoxanthin

Names
IUPAC name (3S,5R,6M,3′S,5′R,6′S)-5′,6′-Epoxy-5,3′-dihydroxy-8′-oxo-6,7-didehydro-5,6,5′,6′,7′,8′-hexahydro-β,β-caroten-3-yl acetate
Systematic IUPAC name (1S,3R,4M)-3-Hydroxy-4-{(3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate
Identifiers
CAS Number	3351-86-8  Y
3D model (JSmol)	Interactive image
Beilstein Reference	6580822
ChEBI	CHEBI:5186
ChEMBL	ChEMBL1575074
ChemSpider	21864745  N
ECHA InfoCard	100.212.315
EC Number	686-524-6
KEGG	C08596
PubChem CID	5281239
UNII	06O0TC0VSM  Y
CompTox Dashboard (EPA)	DTXSID901031617
InChI InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23-,34-,35-,40+,41+,42-/m0/s1 N Key: SJWWTRQNNRNTPU-XJUZQKKNSA-N N InChI=1/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23-,34-,35-,40+,41+,42-/m0/s1 Key: SJWWTRQNNRNTPU-XJUZQKKNBP
SMILES CC(=CC=CC=C(C)C=CC=C(C)C(=O)CC12C(CC(CC1(O2)C)O)(C)C)C=CC=C(C)C=C=C3C(CC(CC3(C)O)OC(=O)C)(C)C
Properties
Chemical formula	C42H58O6
Molar mass	658.920 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P264, P280, P305+P351+P338, P337+P313
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Fucoxanthin is a xanthophyll, with formula C₄₂H₅₈O₆. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510-525 nm by various estimates and absorbing significantly in the range of 450 to 540 nm.

Function

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. ^[1] 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. ^[2]

In macroalgal plastids, fucoxanthin acts like an antenna for light harvesting and energy transfer in the photosystem light harvesting complexes. ^[3] In diatoms like Phaeodactylum tricornutum, fucoxanthin is protein-bound along with chlorophyll to form a light harvesting protein complex. ^[4] Fucoxanthin is the dominant carotenoid, responsible for up to 60% of the energy transfer to chlorophyll a in diatoms ^[5] 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. ^[6]

Sources

Fucoxanthin is present in brown seaweeds and diatoms and was first isolated from Fucus , Dictyota , and Laminaria by Willstätter and Page in 1914. ^[7] 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. ^[8] 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. ^[9]

Bioavailability

Limited studies of fucoxanthin in humans indicate low bioavailability. ^[7]

See also

• Chlorophyll

References

1. Dembitsky VM, Maoka T (November 2007). "Allenic and cumulenic lipids". Progress in Lipid Research. 46 (6): 328–75. doi:10.1016/j.plipres.2007.07.001. PMID   17765976.
2. Hu T, Liu D, Chen Y, Wu J, Wang S (March 2010). "Antioxidant activity of sulfated polysaccharide fractions extracted from Undaria pinnitafida in vitro". International Journal of Biological Macromolecules. 46 (2): 193–8. doi:10.1016/j.ijbiomac.2009.12.004. PMID   20025899.
3. Owens TG, Wold ER (March 1986). "Light-Harvesting Function in the Diatom Phaeodactylum tricornutum: I. Isolation and Characterization of Pigment-Protein Complexes". Plant Physiology. 80 (3): 732–8. doi:10.1104/pp.80.3.732. PMC   1075192 . PMID   16664694.
4. Guglielmi G, Lavaud J, Rousseau B, Etienne AL, Houmard J, Ruban AV (September 2005). "The light-harvesting antenna of the diatom Phaeodactylum tricornutum. Evidence for a diadinoxanthin-binding subcomplex" (PDF). The FEBS Journal. 272 (17): 4339–48. doi: 10.1111/j.1742-4658.2005.04846.x . PMID   16128804.
5. Papagiannakis E, van Stokkum IH, Fey H, Büchel C, van Grondelle R (November 2005). "Spectroscopic characterization of the excitation energy transfer in the fucoxanthin-chlorophyll protein of diatoms". Photosynthesis Research. 86 (1–2): 241–50. doi:10.1007/s11120-005-1003-8. PMID   16172942.
6. Premvardhan L, Sandberg DJ, Fey H, Birge RR, Büchel C, van Grondelle R (September 2008). "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". The Journal of Physical Chemistry B. 112 (37): 11838–53. doi:10.1021/jp802689p. PMC   2844098 . PMID   18722413.
7. Peng J, Yuan JP, Wu CF, Wang JH (2011-10-10). "Fucoxanthin, a marine carotenoid present in brown seaweeds and diatoms: metabolism and bioactivities relevant to human health". Marine Drugs. 9 (10): 1806–28. doi: 10.3390/md9101806 . PMC   3210606 . PMID   22072997.
8. Wang LJ, Fan Y, Parsons RL, Hu GR, Zhang PY, Li FL (January 2018). "A Rapid Method for the Determination of Fucoxanthin in Diatom". Marine Drugs. 16 (1): 33. doi: 10.3390/md16010033 . PMC   5793081 . PMID   29361768.
9. Li H, Ji H, Shi C, Gao Y, Zhang Y, Xu X, Ding H, Tang L, Xing Y (April 2017). "Distribution of heavy metals and metalloids in bulk and particle size fractions of soils from coal-mine brownfield and implications on human health". Chemosphere. 172: 505–515. doi:10.1016/j.chemosphere.2017.01.021. PMID   28104559.