Mangostin (dye)
Structural formula | |||||||||||||||||||
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General | |||||||||||||||||||
Surname | Mangosteen | ||||||||||||||||||
other names |
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Molecular formula | C 24 H 26 O 6 | ||||||||||||||||||
Brief description |
odorless, golden yellow, shiny leaves |
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properties | |||||||||||||||||||
Molar mass | 410.47 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
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Melting point |
190 ° C |
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boiling point |
The substance decomposes on heating above 190 ° C |
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solubility |
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safety instructions | |||||||||||||||||||
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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 ).
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
- ↑ a b c d e f W. Schmid: Ueber das Mangostin , in: Liebigs Ann. 1855 , 93 , 83-88; doi : 10.1002 / jlac.18550930105 .
- ↑ 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. There is not yet a
- ↑ 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 .
- 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.
- ↑ 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.