Fucosterol

Last updated
Fucosterol
Fucosterol.svg
Names
IUPAC name
[24(241)E]-Stigmasta-5,24(241)-dien-3β-ol
Systematic IUPAC name
(1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-Dimethyl-1-[(2R,5E)-5-(propan-2-yl)hept-5-en-2-yl]-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH C015896
PubChem CID
UNII
  • InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7+/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1
    Key: OSELKOCHBMDKEJ-JUGJNGJRSA-N
  • InChI=1/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7+/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1
    Key: OSELKOCHBMDKEJ-JUGJNGJRBM
  • C/C=C(\CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)/C(C)C
Properties
C29H48O
Molar mass 412.702 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fucosterol is a sterol isolated from algae such as Ecklonia cava or Ecklonia stolonifera . [1]

Related Research Articles

<span class="mw-page-title-main">Phytosterol</span> Class of steroids derived from plants

Phytosterols are phytosteroids, similar to cholesterol, that serve as structural components of biological membranes of plants. They encompass plant sterols and stanols. More than 250 sterols and related compounds have been identified. Free phytosterols extracted from oils are insoluble in water, relatively insoluble in oil, and soluble in alcohols.

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

Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed polyphenols.

<span class="mw-page-title-main">Arame</span> Species of edible kelp

Arame, sea oak is a species of kelp, of the brown algae, best known for its use in Japanese cuisine.

<i>beta</i>-Sitosterol Chemical compound

β-sitosterol (beta-sitosterol) is one of several phytosterols with chemical structures similar to that of cholesterol. It is a white, waxy powder with a characteristic odor, and is one of the components of the food additive E499. Phytosterols are hydrophobic and soluble in alcohols.

<span class="mw-page-title-main">CYP27A1</span> Protein-coding gene in the species Homo sapiens

CYP27A1 is a gene encoding a cytochrome P450 oxidase, and is commonly known as sterol 27-hydroxylase. This enzyme is located in many different tissues where it is found within the mitochondria. It is most prominently involved in the biosynthesis of bile acids.

<span class="mw-page-title-main">Sterol regulatory element-binding protein 1</span> Protein-coding gene in the species Homo sapiens

Sterol regulatory element-binding transcription factor 1 (SREBF1) also known as sterol regulatory element-binding protein 1 (SREBP-1) is a protein that in humans is encoded by the SREBF1 gene.

<span class="mw-page-title-main">Red algae</span> Division of plant life

Red algae, or Rhodophyta, are one of the oldest groups of eukaryotic algae. The Rhodophyta comprises one of the largest phyla of algae, containing over 7,000 currently recognized species with taxonomic revisions ongoing. The majority of species (6,793) are found in the Florideophyceae (class), and mostly consist of multicellular, marine algae, including many notable seaweeds. Red algae are abundant in marine habitats but relatively rare in freshwaters. Approximately 5% of red algae species occur in freshwater environments, with greater concentrations found in warmer areas. Except for two coastal cave dwelling species in the asexual class Cyanidiophyceae, there are no terrestrial species, which may be due to an evolutionary bottleneck in which the last common ancestor lost about 25% of its core genes and much of its evolutionary plasticity.

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

Desmosterol (Cholesta-5,24-dien-3β-ol) is a lipid present in the membrane of phytoplankton and an intermediate product in cholesterol synthesis in mammal cells. Structurally, desmosterol has a similar backbone to cholesterol, with the exception of an additional double bond in the structure of desmosterol.

<i>Ecklonia cava</i> Species of seaweed

Ecklonia cava, is an edible marine brown alga species found in the ocean off Japan and Korea.

<i>Ecklonia</i> Genus of seaweeds

Ecklonia is a genus of kelp belonging to the family Lessoniaceae.

<span class="mw-page-title-main">Phlorotannin</span> Class of chemical compounds

Phlorotannins are a type of tannins found in brown algae such as kelps and rockweeds or sargassacean species, and in a lower amount also in some red algae. Contrary to hydrolysable or condensed tannins, these compounds are oligomers of phloroglucinol (polyphloroglucinols). As they are called tannins, they have the ability to precipitate proteins. It has been noticed that some phlorotannins have the ability to oxidize and form covalent bonds with some proteins. In contrast, under similar experimental conditions three types of terrestrial tannins apparently did not form covalent complexes with proteins.

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

Eckol is a phlorotannin isolated from brown algae in the family Lessoniaceae such as species in the genus Ecklonia such as E. cava or E. kurome or in the genus Eisenia such as Eisenia bicyclis.

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

Phlorofucofuroeckol A is a phlorotannin isolated from brown algae species such as Eisenia bicyclis, Ecklonia cava, Ecklonia kurome or Ecklonia stolonifera.

Ecklonia stolonifera is a brown alga species in the genus Ecklonia found in the Sea of Japan. It is an edible species traditionally eaten in Japan.

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

Dieckol is a phlorotannin that can be found in arame, in Ecklonia cava or in Ecklonia stolonifera.

<span class="mw-page-title-main">8,8′-Bieckol</span> Chemical compound

8,8'-Bieckol is an eckol-type phlorotannin found in the brown algae Ecklonia cava and Ecklonia kurome.

<span class="mw-page-title-main">6,6'-Bieckol</span> Chemical compound

6,6'-Bieckol is an eckol-type phlorotannin found in the brown algae Ecklonia cava and Ecklonia stolonifera.

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

Eckstolonol is a phlorotannin found in the edible brown algae arame and turuarame.

<span class="mw-page-title-main">7-Phloroeckol</span> Chemical compound

7-Phloroeckol is a phlorotannin found in the edible brown algae arame and turuarame.

<i>Cochlodinium polykrikoides</i> Species of single-celled organism

Cochlodinium polykrikoides is a species of red tide producing marine dinoflagellates known for causing fish kills around the world, and well known for fish kills in marine waters of Southeast Asia. C. polykrikoides has a wide geographic range, including North America, Central America, Western India, Southwestern Europe and Eastern Asia. Single cells of this species are ovoidal in shape, 30-50μm in length and 25-30μm in width.

References

  1. Zhen, Xing-Hua; Quan, Ying-Chun; Jiang, Hai-Ying; Wen, Zheng-Shun; Qu, You-Le; Guan, Li-Ping (2015). "Fucosterol, a sterol extracted from Sargassum fusiforme, shows antidepressant and anticonvulsant effects". European Journal of Pharmacology. 768: 131–8. doi:10.1016/j.ejphar.2015.10.041. PMID   26515446.