Gamma-mangostin CAS 31271-07-5

Introduction：Basic information about Gamma-mangostin CAS 31271-07-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Gamma-mangostin Basic information

• Product Name: Gamma-mangostin
• Synonyms: Gamma-mangostin;1,3,6,7-Tetrahydroxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one;Normangostin;r-Mangostin;1,3,6,7-Tetrahydroxy-2,8-bis(3-Methylbut-2-en-1-yl)-9H-xanthen-9-one;1,3,6,7-Tetrahydroxy-2,8-bis(3,3-dimethylallyl)xanthone;gamma-Mangostin (r-Mangostin);Nomangostin
• CAS: 31271-07-5
• MF: C23H24O6
• MW: 396.43
• Mol File: 31271-07-5.mol

Gamma-mangostin Chemical Properties

• Melting point: 206-208 °C
• Boiling point: 648.4±55.0 °C(Predicted)
• density: 1.326±0.06 g/cm3(Predicted)
• storage temp.: 2-8°C
• solubility: methanol: soluble1mg/mL, colorless to yellow
• form: powder
• pka: 7.05±0.20(Predicted)
• color: off-white to yellow
• Major Application: metabolomics vitamins, nutraceuticals, and natural products
• InChI: InChI=1S/C23H24O6/c1-11(2)5-7-13-15(24)9-18-20(22(13)27)23(28)19-14(8-6-12(3)4)21(26)16(25)10-17(19)29-18/h5-6,9-10,24-27H,7-8H2,1-4H3
• InChIKey: VEZXFTKZUMARDU-UHFFFAOYSA-N
• SMILES: C1(=O)C2=C(C=C(O)C(O)=C2C/C=C(/C)\C)OC2=C1C(O)=C(C/C=C(/C)\C)C(O)=C2
• LogP: 5.744 (est)

Safety Information

• Hazard Codes: Xn
• Risk Statements: 22
• WGK Germany: 3
• RTECS: ZD6122330
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Acute Tox. 4 Oral

Gamma-mangostin Usage And Synthesis

Background

Garcinia mangostana L., commonly known as mangosteen, is a tree mainly found in India, Myanmar, Sri Lanka and Thailand. The pericarp of mangosteen has been used in Thailand as an indigenous medicine for treating skin infections, wounds and diarrhea. The major bioactive compounds in mangosteen are xanthone derivatives, with α-mangostin (1, α-M) and Gamma-mangostin (4, γ-M) being the main derivatives isolated. α-M and γ-M possess not only antioxidant activity but also a wide range of biological activities, such as tumour cell-selective apoptosis and the attenuation of amyloid-β neurotoxicity and anti-inflammation. Gamma-mangostin strongly inhibited human colorectal adenocarcinoma cell proliferation. It was shown that γ-mangostin may mediate cytotoxicity via apoptosis in HT29 cells. Hence, it is a strong lead compound candidate in treating colon cancer cell growth and may directly affect colorectal adenocarcinoma cancer susceptibility through its modulation of cell proliferation and apoptosis[1].

Chemical Properties

It is soluble in organic solvents such as methanol, ethanol, and DMSO, and is derived from mangosteen shell.

Uses

Gamma-Mangostin is a xanthones which displays anti-oxidant properties and could be a promising compound for the therapy of AlzheimerтАЩs disease.

Definition

ChEBI: A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3, 6 and 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense/ital>, it exhibits antitumour activity.

Biological Activity

Xanthone derivative isolated from the mangosteen hull (Garcinia mangostana). Exhibits antioxidant and anticancer properties. Mangosteen xanthones inhibit inflammation in human adipocytes which is important in understanding obesity-associated inflammation and the development of insulin resistance.

in vivo

Gamma-Mangostin (0.5, 1, 2 mg/kg; Oral gavage (p.o.); 14 days) significantly reduces fasting blood glucose, cholesterol, serum glutamic oxaloacetic transaminase (SGOT), serum glutamic pyruvic transaminase (SGPT), and ameliorates damaged hepatocytes, primarily swelling, hydropic changes, and necrotic cells in the streptozotocin (STZ) (HY-13753) (30 mg/kg) induced diabetic BALB/C mouse model^[3].
Gamma-Mangostin (1, 2, 4 mg/kg; Oral gavage (p.o.); 14 days) significantly reduces blood urea nitrogen (BUN) and creatinine in plasma, and ameliorates the damage to renal proximal tubular cells in BALB/C mice with streptozotocin (STZ) (HY-13753) (30 mg/kg) induced diabetes^[4].
Gamma-Mangostin (0.1, 0.2, 0.4 mg; Oral gavage (p.o.); 4 weeks) can reduce fasting blood glucose levels and oral glucose tolerance tests in diabetic ICR mice^[5].

• Animal Model: STZ (HY-13753) (30 mg/kg)-induced BALB/C diabetic mouse model^[3]
• Dosage: 0.5 mg/kg, 1 mg/kg, 2 mg/kg
• Administration: Oral gavage (p.o.); 14 days
• Result: Significantly reduced fasting blood glucose, cholesterol, serum glutamic oxaloacetic transaminase (SGOT), and serum glutamate-pyruvate transaminase (SGPT) in diabetic mice. Improved damaged liver cells, primarily those exhibiting swelling, water accumulation, and cell necrosis.

IC 50

5-HT_2A Receptor; COX-2

References

[1] Takeshi Yokoyama. “Discovery of γ-Mangostin as an Amyloidogenesis Inhibitor.” Scientific Reports (2015): 13570.