α-, γ-mangostin, also known as α-, γ-mangosteen brass, is a class of compounds containing oxygen xanthone structures widely used in food and medicine. Now there are three main types of mangostins whose structures have been determined, α-, β-, and γ-mangostin. The number of oxy substitutions varies. Because the content of β-mangostin in plants is extremely low, it is difficult to purify, and many biological activities are not as good as α-, γ-mangostin.
Extraction source: Mangosteen (Garcinia mangostana L.), Garcinia, Garcinia, evergreen tree mangosteen fruit shell.
CAS number: 6147-11-1
Molecular formula: C24H26O6
Molecular weight: 410.46
Solubility: Insoluble in water, easily soluble in medium and low polarity solvents such as n-hexane, chloroform, ethyl acetate, etc.
Melting point: 180-182°C
Appearance: yellow powder
Production process: select raw materials, clean raw materials, extract three times, concentrate, spray dry into powder, sieve and sterilize, and pack.
Synthetic process of high-purity natural product α-mangostin:
1) On the acetyl group:
Weigh 250g of α-mangostin crude product SM_1 (purity>70%) into a 5L three-neck flask, add 1L of pyridine under the condition of stirring in an ice bath, slowly add acetic anhydride (1.25L), and control the temperature in the kettle at 10 below the degree. After dropping, heat to reflux for 3h. Concentrate the excess pyridine, add 1.2L of dichloromethane to the concentrate, wash the organic phase twice with 5% dilute hydrochloric acid 600mL×2, back-extract the dilute hydrochloric acid layer with 300mL×2 dichloromethane, and combine the organic phases. The organic phase was washed with 300 mL of saturated brine, dried over anhydrous sodium sulfate, and spin-dried to obtain 326 g of a brown oil, which became solid after cooling at room temperature. The crude product was recrystallized twice with dichloromethane/petroleum ether=1/1, and dried to obtain 220 g of light yellow solid SM_2 with a yield of 67.2%.
2) Deacetylation:
Weigh 2200 g of triacetylated α-mangostin SM_2, add 2 L of ethanol, and stir. Then weigh 149.3g of sodium hydroxide to make 2mol/L and add it to a three-neck flask, heat to reflux, and react for 1 hour. 2), concentrated and dried to obtain 150g of crude product. Add 600 mL of dichloromethane to 150 g of the crude product to dissolve it completely, decolorize with activated carbon, filter, and concentrate to obtain a yellow solid. Dichloromethane/petroleum ether=1/1 recrystallized three times to obtain a large amount of yellow solid, which was filtered under reduced pressure and dried to obtain 96 g of yellow solid with a yield of 57.1%. Purity>99.9%.
Natural Extracts:
The method for separating and purifying α-mangostin from mangosteen, the specific preparation steps are:
(1) Take 8 to 10 freshly picked mangosteens, peel them, put the obtained mangosteen skins into an ultrasonic cleaner, add 3% sodium percarbonate, the liquid level is higher than the mangosteen skins, turn on the ultrasonic cleaner and wash for 3 to 5 minutes , take it out, and clean it with distilled water to obtain clean mangosteen bark;
(2) Put the mangosteen bark obtained above into a drying oven, dry it at room temperature for 1-2 days, take it out, put it into a small ball mill and pulverize it, and pass the mangosteen bark powder through a 250-mesh sieve;
(3) Add distilled water to the mangosteen bark powder until it is submerged 2-3cm above the mangosteen bark powder, heat at a controlled temperature of 70-80°C until the water boils, then add 5-7g of carbon black loaded with hydrophilic organic matter to obtain adsorbed The loaded hydrophilic organic matter carbon black of mangosteen bark powder;
(4) Take out the loaded hydrophilic organic carbon black adsorbed with mangosteen bark powder, immerse in an ethanol solution with a mass fraction of 95%, soak for 15-20min, separate and filter to obtain the precipitate A;
(5) Add 0.2-0.3mol/L dilute hydrochloric acid to the precipitated substance A, carry out acid analysis, adjust the pH to 6-7, and obtain the precipitate;
(6) After washing the precipitate obtained above with deionized water, perform supercritical CO2 extraction for 40-50 minutes, the extraction temperature is 60-70°C, and the extraction pressure is 10-15MPa, and the pure α-mangostin can be obtained .
The main pharmacological activities of mangostin from mangosteen extract:
1. It has good effects on inhibiting fat synthesis, suppressing appetite and reducing body weight.
2. It has the functions of analgesic, antibacterial, antiviral and antimutagenic.
3. The activity of anti-oxidation and elimination of oxygen free radicals has a good protective effect on the cardiovascular system.
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