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The Extraction and Separation Method and Application of Pimaric Acid

A technology of pimaric acid and pinadienoic acid is applied in the separation/purification of carboxylic acid compounds, active ingredients of anhydride/acid/halide, organic chemistry, etc., to achieve the effects of process stability, strong inhibition and high efficiency

Active Publication Date: 2021-03-23
SHAANXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there has been no report on the isolation of pimaric acid from the bark of Wujia

Method used

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  • The Extraction and Separation Method and Application of Pimaric Acid
  • The Extraction and Separation Method and Application of Pimaric Acid
  • The Extraction and Separation Method and Application of Pimaric Acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] This example is one of the preferred implementations of the extraction and separation of pimaric adienoic acid, and the specific operation process is as follows.

[0037] Take by weighing the dried root bark of 10kg of Acanthopanax chinensis, break into a fine powder through a pulverizer, and the particle size of the crushed material is 3-5mm, and set aside. At room temperature, soak twice with 80L acetone-water (70:30, v:v), each time for 72 hours. After combining the two soaking solutions, use a rotary evaporator to concentrate under reduced pressure to a small volume, and control the concentration temperature not to be higher than 55°C. The obtained concentrate was extracted three times with the same amount of ethyl acetate, and the three extracts were combined. The obtained extract was concentrated to dryness to obtain 700 g of an ethyl acetate extract. Dissolve the extracted portion of ethyl acetate with a small amount of dichloromethane-methanol (2:1, v:v) and a...

Embodiment 2

[0040] The embodiment is one of the preferred implementations of the extraction and separation of the pimaric adienoic acid, and the specific operation process is as follows.

[0041]Take by weighing the dried root bark of 2kg of Acanthopanax chinensis, break into fine powder through a pulverizer, and the particle size of the crushed material is 3-5mm, and set aside. At room temperature, soak twice with 20L acetone-water (80:20, v:v), each time for 72 hours. After combining the two soaking solutions, use a rotary evaporator to concentrate under reduced pressure to a small volume, and control the concentration temperature not to be higher than 55°C. The obtained concentrate was extracted three times with the same amount of ethyl acetate, and the three extracts were combined. The resulting extract was concentrated to dryness to obtain 180 g of an ethyl acetate extract. Dissolve the extracted portion of ethyl acetate with a small amount of dichloromethane-methanol (2:1, v:v) an...

Embodiment 3

[0044] figure 1 gives the pimaric adienoic acid 1 H-NMR spectrum. figure 2 gives the pimaric adienoic acid 13 C-NMR spectrum. image 3 The HPLC spectrum of the pimaric acid is given. It has been confirmed that the pimaric dienoic acid extracted and separated in Examples 1 and 2 has the structure of formula (I), and its relevant physical and chemical parameters and structural data are as follows.

[0045] Molecular formula: C 20 h 30 o 2 ;

[0046] Molecular weight: 302.45;

[0047] Properties: white massive crystal;

[0048] Solubility: easily soluble in dichloromethane, chloroform, acetone, almost insoluble in water;

[0049] Melting point: 162–163°C;

[0050] Optical rotation [α]25D=–129°(c=0.8, CHCl 3 );

[0051] 1 H-NMR (600MHz, CDCl 3 )δ H :5.72(1H,dd,J=17.1,10.4Hz,H-15),5.13(1H,br s,H-14),4.93(1H,dd,J=10.4,2.0Hz,H-16a),4.90 (1H, dd, J = 17.1, 2.0 Hz, H-16b), 1.24 (3H, s, H-17), 0.98 (3H, s, H-18), 0.64 (3H, H-20).

[0052] 13 C-NMR (CDCl 3 ,150MHz)δ ...

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Abstract

The invention belongs to the technical field of medicinal chemistry, and discloses a pimaric dienoic acid extraction separation method. Pimaric dienoic acid has the structure of the formula (I), and is extracted and separated from eleutherococcus gracilistylus (araliaceae). The extraction separation method comprises the following steps: 1) extracting eleutherococcus gracilistylus material with anorganic solvent or an organic solvent-water mixed solvent; 2) concentrating an extracting solution of the step 1) under reduced pressure; 3) extracting a concentrated solution of the step 2) with a lipophilic organic solvent; 4) concentrating extracting liquid of step 3) under reduced pressure to obtain an extract; 5) separating the extract of step 4) by column chromatography; 6) concentrating aneluant of step 5) under reduced pressure; and 7) recrystallizing a dried product of step 6). According to the invention, pimaric dienoic acid is separated and purified from the dried root and bark ofeleutherococcus gracilistylus for the first time, and the extraction separation method can be used for the industrial separation and high-purity preparation of pimaric dienoic acid. The method also verifies the activity of pimaric dienoic acid to inhibit xanthine oxidase. (The formula is shown in the description.).

Description

technical field [0001] The technical field of medicinal chemistry of the present invention relates to the extraction and separation technology of natural active ingredients, in particular to a method for extracting and preparing high-purity pimaricadienoic acid from Radix Acanthopanax Radix, and the inhibitory activity of pimaricadienoic acid to xanthine oxidase. Background technique [0002] Pimaradienoic acid (pimaradienoic acid; ent-pimara-8(14), 15-dien-19-oic acid), which has a chemical structure shown in formula (I), belongs to the pimarane type (pimarane) diterpenoids, Japanese scholars first reported in 1967 that it was isolated from the traditional Chinese medicine Duhuo. Subsequent pharmacological studies have shown that pimaric adienoic acid has a wide range of pharmacological effects such as anti-inflammatory, analgesic, anti-tumor, anti-arteriospasm, antibacterial, and insecticidal, among which the anti-inflammatory activity is the most significant, and has been...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/42C07C61/35A61K31/19A61P19/06A61P9/04A61P9/00A61P9/12A61P3/10A61P13/12A61P19/02
CPCA61K31/19C07C51/42C07C61/35
Inventor 许洪波唐志书王薇宋逍孙琛宋忠兴
Owner SHAANXI UNIV OF CHINESE MEDICINE
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