Fucoxanthin

Last updated
Fucoxanthin
Fucoxanthin.svg
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
3D model (JSmol)
3DMet
6580822
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.212.315 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 686-524-6
KEGG
PubChem CID
UNII
  • 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 X mark.svgN
    Key: SJWWTRQNNRNTPU-XJUZQKKNSA-N X mark.svgN
  • 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
  • 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
C42H58O6
Molar mass 658.920 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H319
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).
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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.

Contents

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]

Potential therapeutic applications

Fucoxanthin has been shown to induce G1 cell-cycle arrest and apoptosis in various cancer cell lines and tumor growth in animal models of cancer. [10] [11] Fucoxanthin also reduces weight, improves blood lipid profiles, and decreased insulin resistance in animal models of obesity. [12] [13] [14] In a human clinical trial Fucoxanthin was shown to improve weight parameters in slightly obese Japanese subjects. [15] Applications regarding diabetes are suggested by some research. [16] In nonclinical assessments, fucoxanthin showed the capacity to notably inhibit the growth of Mycobacterium tuberculosis. Its mechanism of action was found to be correlated to the ability to inactivate two vital enzymes that play a significant role in mycobacterial cell wall biosynthesis namely UDP-galactopyranose mutase (UGM) and arylamine-N-acetyltransferase (TBNAT). [17]

Bioavailability and safety

Limited studies of the bioavailability of fucoxanthin in humans suggest that it is low but might be improved through formulation. [18] In rodents, fucoxanthin displays low toxicity when administered orally. [18] While human safety data is limited, the FDA has acknowledged the use of Fucoxanthin as a dietary supplement and filled a New Dietary Ingredient (NDI) notification of Fucoxanthin derived from the microalgae Phaeodactylum tricornutum . [19]

See also

Related Research Articles

<span class="mw-page-title-main">Chloroplast</span> Plant organelle that conducts photosynthesis

A chloroplast is a type of membrane-bound organelle known as a plastid that conducts photosynthesis mostly in plant and algal cells. The photosynthetic pigment chlorophyll captures the energy from sunlight, converts it, and stores it in the energy-storage molecules ATP and NADPH while freeing oxygen from water in the cells. The ATP and NADPH is then used to make organic molecules from carbon dioxide in a process known as the Calvin cycle. Chloroplasts carry out a number of other functions, including fatty acid synthesis, amino acid synthesis, and the immune response in plants. The number of chloroplasts per cell varies from one, in unicellular algae, up to 100 in plants like Arabidopsis and wheat.

<span class="mw-page-title-main">Carotenoid</span> Class of chemical compounds; yellow, orange or red plant pigments

Carotenoids are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, archaea, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, and daffodils. Over 1,100 identified carotenoids can be further categorized into two classes – xanthophylls and carotenes.

<span class="mw-page-title-main">Chloroplast membrane</span>

Chloroplasts contain several important membranes, vital for their function. Like mitochondria, chloroplasts have a double-membrane envelope, called the chloroplast envelope, but unlike mitochondria, chloroplasts also have internal membrane structures called thylakoids. Furthermore, one or two additional membranes may enclose chloroplasts in organisms that underwent secondary endosymbiosis, such as the euglenids and chlorarachniophytes.

<span class="mw-page-title-main">Chromoplast</span> Pigment-bearing organelle in plant cells

Chromoplasts are plastids, heterogeneous organelles responsible for pigment synthesis and storage in specific photosynthetic eukaryotes. It is thought that like all other plastids including chloroplasts and leucoplasts they are descended from symbiotic prokaryotes.

<span class="mw-page-title-main">Xanthophyll</span> Chemical compounds subclass

Xanthophylls are yellow pigments that occur widely in nature and form one of two major divisions of the carotenoid group; the other division is formed by the carotenes. The name is from Greek: xanthos (ξανθός), meaning "yellow", and phyllon (φύλλον), meaning "leaf"), due to their formation of the yellow band seen in early chromatography of leaf pigments.

<span class="mw-page-title-main">Astaxanthin</span> Chemical compound

Astaxanthin is a keto-carotenoid within a group of chemical compounds known as terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups. It is a lipid-soluble pigment with red coloring properties, which result from the extended chain of conjugated double bonds at the center of the compound.

<span class="mw-page-title-main">Zeaxanthin</span> Chemical compound

Zeaxanthin is one of the most common carotenoids in nature, and is used in the xanthophyll cycle. Synthesized in plants and some micro-organisms, it is the pigment that gives paprika, corn, saffron, goji (wolfberries), and many other plants and microbes their characteristic color.

<span class="mw-page-title-main">Light-harvesting complexes of green plants</span> Component of photosynthesis

The light-harvesting complex is an array of protein and chlorophyll molecules embedded in the thylakoid membrane of plants and cyanobacteria, which transfer light energy to one chlorophyll a molecule at the reaction center of a photosystem.

A light-harvesting complex consists of a number of chromophores which are complex subunit proteins that may be part of a larger super complex of a photosystem, the functional unit in photosynthesis. It is used by plants and photosynthetic bacteria to collect more of the incoming light than would be captured by the photosynthetic reaction center alone. The light which is captured by the chromophores is capable of exciting molecules from their ground state to a higher energy state, known as the excited state. This excited state does not last very long and is known to be short-lived.

<span class="mw-page-title-main">Chlorosome</span>

A chlorosome is a photosynthetic antenna complex found in green sulfur bacteria (GSB) and many green non-sulfur bacteria (GNsB), together known as green bacteria. They differ from other antenna complexes by their large size and lack of protein matrix supporting the photosynthetic pigments. Green sulfur bacteria are a group of organisms that generally live in extremely low-light environments, such as at depths of 100 metres in the Black Sea. The ability to capture light energy and rapidly deliver it to where it needs to go is essential to these bacteria, some of which see only a few photons of light per chlorophyll per day. To achieve this, the bacteria contain chlorosome structures, which contain up to 250,000 chlorophyll molecules. Chlorosomes are ellipsoidal bodies, in GSB their length varies from 100 to 200 nm, width of 50-100 nm and height of 15 – 30 nm, in GNsB the chlorosomes are somewhat smaller.

<i>Phaeodactylum tricornutum</i> Species of single-celled organism

Phaeodactylum tricornutum is a diatom. It is the only species in the genus Phaeodactylum. Unlike other diatoms, P. tricornutum can exist in different morphotypes and changes in cell shape can be stimulated by environmental conditions. This feature can be used to explore the molecular basis of cell shape control and morphogenesis. Unlike most diatoms, P. tricornutum can grow in the absence of silicon and can survive without making silicified frustules. This provides opportunities for experimental exploration of silicon-based nanofabrication in diatoms.

Tetraterpenes are terpenes consisting of eight isoprene units and have the molecular formula C40H64. Tetraterpenoids (including many carotenoids) are tetraterpenes that have been chemically modified, as indicated by the presence of oxygen-containing functional groups.

<span class="mw-page-title-main">Biological pigment</span> Substances produced by living organisms

Biological pigments, also known simply as pigments or biochromes, are substances produced by living organisms that have a color resulting from selective color absorption. Biological pigments include plant pigments and flower pigments. Many biological structures, such as skin, eyes, feathers, fur and hair contain pigments such as melanin in specialized cells called chromatophores. In some species, pigments accrue over very long periods during an individual's lifespan.

<span class="mw-page-title-main">Peridinin</span> Chemical compound

Peridinin is a light-harvesting apocarotenoid, a pigment associated with chlorophyll and found in the peridinin-chlorophyll-protein (PCP) light-harvesting complex in dinoflagellates, best studied in Amphidinium carterae.

<i>Micromonas</i> Genus of algae

Micromonas is a genus of green algae in the family Mamiellaceae.

Chlorophyll c refers to forms of chlorophyll found in certain marine algae, including the photosynthetic Chromista and dinoflagellates. These pigments are characterized by their unusual chemical structure, with a porphyrin as opposed to the chlorin as the core; they also do not have an isoprenoid tail. Both these features stand out from the other chlorophylls commonly found in algae and plants.

<span class="mw-page-title-main">Diadinoxanthin</span> Chemical compound

Diadinoxanthin is a pigment found in phytoplankton. It has the formula C40H54O3. It gives rise to the xanthophylls diatoxanthin and dinoxanthin.

<span class="mw-page-title-main">Peridinin-chlorophyll-protein complex</span>

The peridinin-chlorophyll-protein complex is a soluble molecular complex consisting of the peridinin-chlorophyll a-protein bound to peridinin, chlorophyll, and lipids. The peridinin molecules absorb light in the blue-green wavelengths and transfer energy to the chlorophyll molecules with extremely high efficiency. PCP complexes are found in many photosynthetic dinoflagellates, in which they may be the primary light-harvesting complexes.

Aureochromes are blue light photoreceptors as well as transcription factors found only in stramenopiles so far.

<span class="mw-page-title-main">Marine primary production</span> Marine synthesis of organic compounds

Marine primary production is the chemical synthesis in the ocean of organic compounds from atmospheric or dissolved carbon dioxide. It principally occurs through the process of photosynthesis, which uses light as its source of energy, but it also occurs through chemosynthesis, which uses the oxidation or reduction of inorganic chemical compounds as its source of energy. Almost all life on Earth relies directly or indirectly on primary production. The organisms responsible for primary production are called primary producers or autotrophs.

References

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Other studies