Arugosin C

Last updated
Arugosin C
Arugosin C.svg
Names
IUPAC name
7,11-Dihydroxy-17-(2-hydroxypropan-2-yl)-13-methyl-6-(3-methylbut-2-enyl)-2,15-dioxatetracyclo[8.7.1.03,8.014,18]octadeca-3(8),4,6,10,12,14(18)-hexaen-9-one
Identifiers
  • 50875-10-0 Yes check.svgY
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C25H28O6/c1-12(2)6-7-14-8-9-17-19(21(14)27)22(28)18-16(26)10-13(3)23-20(18)24(31-17)15(11-30-23)25(4,5)29/h6,8-10,15,24,26-27,29H,7,11H2,1-5H3
    Key: MYJGUMZTENHAAQ-UHFFFAOYSA-N
  • CC1=CC(=C2C3=C1OCC(C3OC4=C(C2=O)C(=C(C=C4)CC=C(C)C)O)C(C)(C)O)O
Properties
C25H28O6
Molar mass 424.493 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Arugosin C is an anthraquinone derivative isolated from a species of Aspergillus found in the Red Sea. [1]

Related Research Articles

Anthraquinone Chemical compound

Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
14
H
8
O
2
. Isomers include various quinone derivatives. The term anthraquinone, however refers to the isomer, 9,10-anthraquinone wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite.

<i>Aspergillus</i> Genus of fungi

Aspergillus is a genus consisting of a few hundred mould species found in various climates worldwide.

Anthraquinones

For the parent molecule 9,10-anthraquinone, see anthraquinone

Emodin Chemical compound

Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a chemical compound, of the anthraquinone family, that can be isolated from rhubarb, buckthorn, and Japanese knotweed. Emodin is particularly abundant in the roots of the Chinese rhubarb, knotweed and knotgrass as well as Hawaii ‘au‘auko‘i cassia seeds or coffee weed. It is specifically isolated from Rheum Palmatum L. It is also produced by many species of fungi, including members of the genera Aspergillus, Pyrenochaeta, and Pestalotiopsis, inter alia. The common name is derived from Rheum emodi, a taxonomic synonym of Rheum australe, and synonyms include emodol, frangula emodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schuttgelb, and Persian Berry Lake.

In enzymology, a questin monooxygenase (EC 1.14.13.43) is an enzyme that catalyzes the chemical reaction

Solamargine Chemical compound

Solamargine is a poisonous chemical compound that occurs in plants of the family Solanaceae, such as potatoes, tomatoes, and eggplants. It has been also isolated from Solanum nigrum fungal endophyte Aspergillus flavus. It is a glycoalkaloid derived from the steroidal alkaloid solasodine.

Glyceollin III Chemical compound

Glyceollin III is a glyceollin, a type of pterocarpan, found in the soybean. It has an antiestrogenic effect. In soil, it has an antifungal activity against Aspergillus sojae.

Disperse dye is a category of synthetic dye intended for polyester and related hydrophobic fibers. Disperse dyes are polar molecules containing anthraquinone or azo groups. It is estimated that 85% of disperse dyes are azos or anthraquinone dyes.

Aspergillus sydowii is a pathogenic fungus that causes several diseases in humans. It has been implicated in the death of sea fan corals in the Caribbean Sea.

El Ikhwa Islands Two islands in the Egyptian Red Sea

El Ikhwa Islands, commonly known as Brothers Islands, are two small Red Sea islands in the Red Sea Governorate of Egypt.

Spiculisporic acid Chemical compound

Spiculisporic acid is a bioactive γ-butenolide. It was originally isolated from Penicillium spiculisporum. Structural variants have been isolated from a marine Aspergillus.

Siderin Chemical compound

Siderin is a bio-active coumarin derivative produced by Aspergillus versicolor, an endophytic fungus found in the green alga Halimeda opuntia in the Red Sea.

Evariquinone Chemical compound

Evariquinone is a chemical compound of the anthraquinone class which has been isolated from a sponge-derived strain of the fungus Emericella variecolor and from Aspergillus versicolor.

<i>Aspergillus versicolor</i> Species of fungus

Aspergillus versicolor is a slow-growing filamentous fungus commonly found in damp indoor environments and on food products. It has a characteristic musty odor associated with moldy homes and is a major producer of the hepatotoxic and carcinogenic mycotoxin sterigmatocystin. Like other Aspergillus species, A. versicolor is an eye, nose, and throat irritant.

Fungal isolates have been researched for decades. Because fungi often exist in thin mycelial monolayers, with no protective shell, immune system, and limited mobility, they have developed the ability to synthesize a variety of unusual compounds for survival. Researchers have discovered fungal isolates with anticancer, antimicrobial, immunomodulatory, and other bio-active properties. The first statins, β-Lactam antibiotics, as well as a few important antifungals, were discovered in fungi.

Aspergillus austroafricanus is a species of fungus in the genus Aspergillus. It is from the Versicolores section. The species was first described in 2012. It has been isolated in South Africa.

Aspergillus bicolor is a species of fungus in the genus Aspergillus. It is from the Aenei section. The species was first described in 1978. It has been reported to produce sterigmatocystin, versicolorins, and some anthraquinones.

Aspergillus christenseniae is a species of fungus in the genus Aspergillus. It is from the Cervini section. The species was first described in 2016. It has been reported to produce 4-hydroxymellein, terremutin, orange-red anthraquinone, and chlorflavonin. The species was named for Martha Christensen.

Aspergillus carneus is a fast-growing, filamentous fungus found on detritus and in fertile soil worldwide. It is characterized by its yellow, thick-walled hyphae and biseriate sterigmata. The fungus produces citrinin and 5 unique depsipeptides, Aspergillicins A-E.

Terrein Chemical compound

Terrein is a fungal metabolite of Aspergillus species. Terrein forms pale yellow crystal needles. Terrein has a strong cytotoxic activity against cells with colorectal carcinoma. The strain S020 from the fungus Aspergillus terreus has the highest rate in producing terrein.

References

  1. Hawas, U. W.; El-Beih, A. A.; El-Halawany, A. M. (2012). "Bioactive anthraquinones from endophytic fungus Aspergillus versicolor isolated from red sea algae". Archives of Pharmacal Research. 35 (10): 1749–56. doi:10.1007/s12272-012-1006-x. PMID   23139125. S2CID   25106490.