Mangostin

Mangostin is a natural xanthonoid, a type of organic compound isolated from various parts of the mangosteen tree (Garcinia mangostana). It is a yellow crystalline solid with a xanthone core structure. Mangostin and a variety of other xanthonoids from mangosteen have been investigated for biological properties including antioxidant, anti-bacterial, anti-inflammatory, and anticancer activities.[1]

Mangostin
Names
Preferred IUPAC name
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
Other names
alpha-mangostin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.208.637
UNII
  • InChI=1S/C24H26O6/c1-12(2)6-8-14-16(25)10-19-21(22(14)27)23(28)20-15(9-7-13(3)4)24(29-5)17(26)11-18(20)30-19/h6-7,10-11,25-27H,8-9H2,1-5H3 checkY
    Key: GNRIZKKCNOBBMO-UHFFFAOYSA-N checkY
  • InChI=1/C24H26O6/c1-12(2)6-8-14-16(25)10-19-21(22(14)27)23(28)20-15(9-7-13(3)4)24(29-5)17(26)11-18(20)30-19/h6-7,10-11,25-27H,8-9H2,1-5H3
    Key: GNRIZKKCNOBBMO-UHFFFAOYAL
  • CC(=CCC1=C(C=C2C(=C1O)C(=O)C3=C(C(=C(C=C3O2)O)OC)CC=C(C)C)O)C
Properties
C24H26O6
Molar mass 410.45 g/mol
Appearance Yellow crystalline solid
Density 1.265 g/ml
Melting point 182 °C (360 °F; 455 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

In animal studies, mangostin has been found to be a central nervous system depressant which causes sedation, decreased motor activity, and ptosis.[2]

The rind of partially ripe mangosteen fruit yields mangostin and also the related compound β-mangostin. Researchers conducted the optimization steps in order to increase the yield of α-Mangostin extraction from the pericarp of the mangosteen and was able to achieve 9.2 g/kg DW. [3] The rind of fully ripe fruits contains the xanthonoids gartanin, 8-disoxygartanin and normangostin. A derivative of mangostin, mangostin-3,6-di-O-glucoside, is a central nervous system depressant and causes a rise in blood pressure.

References
  1. Jung H, Su B, Keller W, Mehta R, Kinghorn A (2006). "Antioxidant xanthones from the pericarp of Garcinia mangostana (Mangosteen)". J. Agric. Food Chem. 54 (6): 2077–82. doi:10.1021/jf052649z. PMID 16536578.
  2. Shankaranarayan D, Gopalakrishnan C, Kameswaran L (1979). "Pharmacological profile of mangostin and its derivatives". Arch Int Pharmacodyn Ther. 239 (2): 257–269. PMID 314790.
  3. Khaw, Kooi Yeong; Ong, Yong Sze; Goh, Bey-Hing (2020). "A Rapid Method for the Retrieval of Bioactive Xanthone from Garcinia Mangostana: A Case Study of α-Mangostin". Progress in Drug Discovery & Biomedical Science. 3 (1). doi:10.36877/pddbs.a0000072.
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