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Process for preparing corosolic acid and crataegolic acid

A technology of corosolic acid and maslinic acid, applied in the field of synthesis that can be applied industrially, can solve the problems of high production cost, complex extraction process, conversion of maslinic acid methyl ester, etc., achieve short reaction time, simple reaction conditions, and high yield high effect

Inactive Publication Date: 2005-07-06
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the limited source of olives, complex extraction process and high production cost, the plant extraction and preparation of maslinic acid is limited, which also limits the application of maslinic acid in medicine and health care.
Caglioti etc. have reported the semi-synthetic preparation of maslinic acid methyl ester, but due to adopting conventional acid or alkali hydrolysis method can not effectively convert maslinic acid methyl ester into maslinic acid, therefore, Caglioti etc. have not realized the effective preparation of maslinic acid ( Caglioti et al., TETRAHEDRON, 1962, 1061)

Method used

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  • Process for preparing corosolic acid and crataegolic acid
  • Process for preparing corosolic acid and crataegolic acid
  • Process for preparing corosolic acid and crataegolic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Preparation of benzyl ursolic acid (7a, R = benzyl)

[0059] Suspend ursolic acid (10.0g) in 100mL of anhydrous DMF, heat at 100°C to dissolve completely, let stand for a little cooling, then add K 2 CO 3 (6.04g) and benzyl chloride (3.0mL). The mixture was heated at 100°C with stirring until the starting material disappeared (ca. 3 hours). After cooling, filter with suction, and wash the solid with DMF 3 times, 15 mL each time. Pour the mother liquor into 500mL of water, shake while pouring to disperse the precipitated solids, let stand until the solids are completely precipitated, collect the solids by suction filtration, and wash them thoroughly with water. After drying, 11.54 g of white benzyl ursolic acid crude product was obtained (crude yield 96.4%). This crude product was directly used in the next reaction without purification. A pure analytical sample was obtained by column chromatography (eluent, petroleum ether: ethyl acetate = 5:1).

[0060] 1 HNMR (C...

Embodiment 2

[0062] Preparation of methyl ursolic acid (7a, R = methyl)

[0063] Ursolic acid (1.0g) was suspended in 10mL of anhydrous DMF, adding K 2 CO 3 (0.6g) and MeI (0.15mL), stirred at room temperature for 4 hours. After dilution with water, it was extracted with ethyl acetate, and the combined ethyl acetate layer was washed with 1% aqueous hydrochloric acid solution and saturated aqueous sodium chloride solution successively, and dried over anhydrous sodium sulfate. After distilling off the solvent, 1.06 g of a white crude product of methyl ursolic acid was obtained. This crude product was directly used in the next reaction without purification. 0.13 g of the crude product was subjected to silica gel column chromatography (eluent, petroleum ether: ethyl acetate = 6: 1) to obtain 0.12 g of pure methyl ursolic acid.

[0064] 1 HNMR (CDCl 3 , 500MHz): δ0.75, 0.80, 0.93, 1.00, 1.08(each, 3H, s), 0.87(3H, d, J=6.5Hz), 0.95(3H, d, J=6.2Hz), 2.24(1H , d, J=10.5Hz, H-18), 3.22 (1H,...

Embodiment 3

[0066] Preparation of benzyl oleanate (7b, R = benzyl)

[0067] Oleanolic acid (10.0g) was suspended in 100mL of anhydrous DMF, heated at 100°C to dissolve completely, and then added K 2 CO 3 (6.04g) and benzyl chloride (3.0mL). The mixture was heated at 100°C with stirring until the starting material disappeared (ca. 3 hours). After cooling, filter with suction, and wash the solid with DMF 3 times, 15 mL each time. Pour the mother liquor into 500mL of water, shake while pouring to disperse the precipitated solids, let stand until the solids are completely precipitated, collect the solids by suction filtration, and wash them thoroughly with water. After drying, 11.51 g of white crude benzyl oleanate was obtained (crude yield 96%). This crude product was directly used in the next reaction without purification. Pure analytical samples were obtained by recrystallization from ethanol twice.

[0068] 1 HNMR (CDCl 3 , 500MHz): δ0.62, 0.78, 0.88, 0.90, 0.92, 0.98, 1.13(each, ...

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Abstract

Disclosed are preparing processes for industrialized application of Corosolic acid with blood sugar lowering, weight reducing, anti-tumor and anti-inflammatory actions and maslinic acid with anti-tumor, anti-virus and cardiovascular diseases resistant actions. The processes include respectively preparing Corosolic acid and maslinic acid using 3-carbonyl ursolic acid ester and 3-carbonyl oleanolic acid ester by acid catalysed enolization esterification reaction, hydroboration oxidation reaction, catalytic hydrogenolysis reaction and haloidlysis reaction.

Description

technical field [0001] The invention belongs to an industrially applicable synthesis method of corosolic acid and maslinic acid with low content in plants. Background technique [0002] Lagerstroernia Speciosa L., commonly known as Banaba, abounds in the Philippine Islands and is distributed in southern China, Brazil and Australia. In the Philippines, people traditionally make tea from Panaba leaves to combat diabetes and obesity (Garcia et al., J. Philippine Medical Association, 1940, 20, 395). Kakuda et al. reported that the extract of Banaba leaves had hypoglycemic effect on hereditary diabetic mice (Kakuda et al., Biosci. Biotech. Biochem. 1996, 60, 204). US patents US 6,485,760 and US 6,716,459 report methods and formulas for regulating blood sugar with the extract of Panaba leaves. US patent application US 20040072906 reports a new dosage form of Glucosol for weight loss and blood sugar regulation. A clinical trial carried out in 1999 further verified the effect of ...

Claims

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Application Information

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IPC IPC(8): C07J63/00
Inventor 孙宏斌温小安倪沛洲
Owner CHINA PHARM UNIV
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