Mangostin (dye)

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Structural formula
Structural formula of α-Mangostin
General
Surname Mangosteen
other names
  • 1,3,6-trihydroxy-7-methoxy-2,8-bis (3-methyl-2-butenyl) -9 H -xanthene-9-one
  • α-mangosteen
  • Mangosteen
  • Mangosteen
Molecular formula C 24 H 26 O 6
Brief description

odorless, golden yellow, shiny leaves

External identifiers / databases
CAS number 6147-11-1
EC number 683-120-1
ECHA InfoCard 100.208.637
PubChem 5281650
ChemSpider 4444969
Wikidata Q909638
properties
Molar mass 410.47 g mol −1
Physical state

firmly

Melting point

190 ° C

boiling point

The substance decomposes on heating above 190 ° C

solubility
safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 301
P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mangostin (also mangosteen ) is a plant pigment from the group of xanthones , which can be obtained from different parts of the tropical tree species mangosteen ( Garcinia mangostana ) as well as from some Achariaceae (such as Hydnocarpus octandra or H. venenata ).

Mangosteen tree ( Garcinia mangostana )

Chemistry and properties

The yellow crystalline substance has a 9 H - xanthone skeleton which is substituted several times with hydroxyl , 3-methyl-2-butenyl and one methoxy group; it is therefore a natural polyphenol . Mangostin is one of the substances that gives components of the mangosteen tree its yellow color. The odorless and tasteless, golden-yellow, shiny platelets do not dissolve in water, but dissolve well in ether, ethanol and diluted acids and alkalis. The reducing effect - for example on metal oxides - was already described when it was published in Justus Liebig's Annalen der Chemie in 1855 .

Medicinal properties and uses

In recent years, mangosteen, like other natural polyphenols, has been said to have positive health effects, which is why it is available in the form of additives in health drinks and as a powder. The mangostin and similar xanthones are then examined for a variety of biological effects, such as B. Antioxidant, antibacterial and anti-inflammatory properties. According to studies from 2007, the anti- inflammatory effect is based on the inhibition of the cyclooxygenases COX-1 and COX-2 . In the suspected effect on cancer , the α-mangostin triggers cell death in the cancer cells , the so-called apoptosis . In cell and organ cultures of mice, α-mangostin suppressed the formation of carcinomas using the carcinogen 7,12-dimethylbenzo [ a ] anthracene in concentrations from 1 μg · ml −1 .

Individual evidence

  1. a b c d e f W. Schmid: Ueber das Mangostin , in: Liebigs Ann. 1855 , 93 , 83-88; doi : 10.1002 / jlac.18550930105 .
  2. Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 1,3,6-trihydroxy-7-methoxy-2,8-bis (3-methyl-2-butenyl) -9H-xanthene- in the Classification and Labeling Inventory of the European Chemicals Agency is reproduced from a self-classification by the distributor (ECHA), accessed January 13, 2020.
  3. a b Jung, HA et al. (2006): Antioxidant xanthones from the pericarp of Garcinia mangostana (Mangosteen). In: J Agric Food Chem . Vol. 54, pp. 2077-2082, PMID 16536578 .
  4. Jump up ↑ YW Chin, HA Jung, H. Chai, WJ Keller, AD Kinghorn: Xanthones with quinone reductase-inducing activity from the fruits of Garcinia mangostana (Mangosteen). In: Phytochemistry 20071106.
  5. Y. Nakagawa, M. Iinuma, T. Naoe, Y. Nozawa, Y. Akao: Characterized mechanism of alpha-mangostin-induced cell death: caspase-independent apoptosis with release of endonuclease-G from mitochondria and increased miR-143 expression in human colorectal cancer DLD-1 cells. In: Bioorganic & Medicinal Chemistry ; VOL: 15 (16); Pp. 5620-8.