CN111116329A - Preparation method and application of isolariciresinol - Google Patents
Preparation method and application of isolariciresinol Download PDFInfo
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- CN111116329A CN111116329A CN201911266989.XA CN201911266989A CN111116329A CN 111116329 A CN111116329 A CN 111116329A CN 201911266989 A CN201911266989 A CN 201911266989A CN 111116329 A CN111116329 A CN 111116329A
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- C07—ORGANIC CHEMISTRY
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
- A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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Abstract
The invention discloses a preparation method and application of isolariciresinol, wherein the isolariciresinol is extracted from beehive grass, and the beehive grass serving as a raw material has wide sources.
Description
Technical Field
The invention relates to a preparation method and application of isolarch rosin.
Background
Crepe flour grass (academic name:Leucas zeylanica) Is a kind of perennial herb belonging to the genus Sauropus androgynus of the family Labiatae, and is divided into Guangdong, Guangxi, Yunnan and other places; growing in sand, loamy coastal areas, fields, roadside and gentle slope areas. The herba Melissae axillaris is whole plant of herba Plectranthi Amboiniculatae, and can be used for treating common cold with cough, toothache, gastrointestinal discomfort, pertussis, etc. Through preliminary phytochemical investigation on the beehive grass, the beehive grass contains alkaloid, steroid, tannin, flavonoid, glycoside and other components.
The isolariciresinol is a lignan compound, is used as a standard substance and a reference substance, and has no report about other purposes.
Disclosure of Invention
The invention aims to solve the technical problem of providing a preparation method and application of the isolariciresinol diglucoside, providing a new path for extracting the compound, and the compound has obvious application effects on reducing blood sugar and resisting oxidation.
The first technical scheme for realizing the first purpose of the invention is the application of the isolariciresinol in preparing the hypoglycemic medicament.
The second technical scheme for realizing the first purpose of the invention is the application of the isolariciresinol in preparing the antioxidant drugs.
The technical scheme for realizing the second purpose of the invention is a preparation method of the isolariciresinol, comprising the following steps:
① soaking dried herba Apii Graveolentis in ethanol, mixing extractive solutions, distilling under reduced pressure to obtain ethanol extract, dispersing the ethanol extract in distilled water, and sequentially extracting with petroleum ether and ethyl acetate to obtain petroleum ether extract and ethyl acetate extract.
② subjecting the ethyl acetate part extract obtained in step ① to silica gel column chromatography, eluting with petroleum ether-ethyl acetate solvent system according to gradient of 100: 1-0: 100 (v/v), collecting fractions per 200 mL and detecting by TLC, and mixing the same fractions to obtain 6 fractions Fr.1-Fr.6.
③ separating the fourth major fraction Fr.4 from step ② by Sephadex LH-20 Sephadex column chromatography (solvent system chloroform: methanol = 1: 1, V/V) to obtain four subfractions Fr.4-1, Fr.4-2, Fr.4-3 and Fr.4-4.
④ Fr.4-3 fraction of step ③ was separated by HPLC using mobile phase acetonitrile-water (35: 75, v/v) to obtain isolariciresinol.
In step ①, the extract is extracted by soaking in ethanol at room temperature (15-35 ℃), and the extraction is carried out for 2-4 times, 2.5-4 days each time.
The invention has the positive effects that:
the invention provides a new source of the isolariciresinol, which can be extracted from beehive grass with wide sources.
The invention discloses a new application of isolariciresinol in the aspects of blood sugar reduction and oxidation resistance, and in-vitro experiments show that the isolariciresinol has better α -glycosidase inhibitory activity and anti-free radical activity.
Detailed Description
Example 1 preparation of Isolariciresinol
The preparation method of the isolariciresinol diglucoside of the embodiment comprises the following steps:
① soaking 4kg of dried herb honeycomb in 75% ethanol at room temperature (15-35 deg.C) for 2-4 times (3 times in this example), each time for 2.5-4 days (3 days in this example), each time using 30L of ethanol, filtering to obtain extractive solution, mixing extractive solutions, distilling under reduced pressure to obtain total ethanol extract 351g, dispersing 351g of total ethanol extract in 1L of distilled water, extracting with petroleum ether for 3 times (3 × 3.5L) to obtain petroleum ether extract, extracting with ethyl acetate for 3 times (3 × 4.0L), and obviously lightening the upper layer solution to obtain ethyl acetate extract.
The honeycomb grass used in the embodiment is collected from Haikou city of Hainan province, and the specimens are stored in key laboratories of the chemical education department of tropical medicinal resources of the university of Hainan teachers and universities.
② subjecting 90g of ethyl acetate part extract obtained in step ① to silica gel column chromatography, eluting with petroleum ether-ethyl acetate solvent system according to gradient of 100: 1-0: 100 (v/v), collecting fractions per 200 mL and detecting by TLC (thin layer chromatography), and combining the same fractions to obtain 6 fractions (Fr.1-Fr.6).
③ separating the fourth major fraction Fr.4 from step ② by Sephadex LH-20 Sephadex column chromatography (solvent system chloroform: methanol = 1: 1, V/V) to obtain four subfractions Fr.4-1, Fr.4-2, Fr.4-3 and Fr.4-4.
④ Fr.4-3 fractions from step ③ were separated by HPLC using mobile phase acetonitrile-water (35: 75, v/v) to give 5.8mg of the desired extract.
Analysis of target extract product:
process for the extraction of step ④1H and13the C-NMR data are as follows (Brooks (Beijing) science and technology Ltd, model AV-III 400 MHz nuclear magnetic resonance apparatus, TMS internal standard,1H 400 Hz ,13C 100 Hz):
the comparison confirms that the extract obtained in step ④ is the isolariciresinol.
(test example 1 evaluation of α -glucosidase inhibitory Activity of Compound)
α -glucosidase inhibitory activity was performed in 96-well plates using the PNPG method.
1.1 preparation of reaction solution.
Preparing α -glucosidase enzyme solution, dissolving lyophilized enzyme powder with 0.01M PBS buffer solution containing 0.2% bovine serum albumin to obtain 0.2U/mL α -glucosidase enzyme solution for use.
Test sample solution: preparing the isolarch resin solution with the concentration range of 10 mu M to 1000 mu M for standby, wherein the solvent is 50 percent methanol water solution.
1.2 α -determination of glucosidase inhibitory activity.
Accurately transferring 20 mu L of 0.1 mol.L-1Adding 20 mu L of test sample into a 96-well plate, respectively, uniformly mixing, reacting at 37 ℃ for 5min, adding 20 mu L of 2.5mmol/L PNPG solution into each well of the 96-well plate, reacting at 37 ℃ for 15 min, and adding 0.2 mol/L Na2CO3The reaction was stopped with 80. mu.L of the solution, and the absorbance was measured at a wavelength of 405 nm.
Acarbose was dissolved in double distilled water, filtered through filter paper, and diluted with methanol to various concentrations as a positive control.
The inhibition rate and IC of α -glucosidase are calculated according to the formula50The value is obtained.
Inhibition (%) = [ (AS-ASB)/(AC-ACB) ] × 100%.
α -glucosidase inhibition IC of isolariciresinol50The value was 2.76 mM.
α -glucosidase inhibitory IC of acarbose as control50The value was 5.17 mM.
(test example 2, detection of ABTS radical scavenging Activity)
A stock solution of ABTS was prepared by adding 1.7mL of 140mmol/L potassium persulfate solution to 100mL of 7mmol/L ABTS solution and reacting at 25 ℃ in the dark for 12 hours. The ABTS stock solution was diluted with phosphate buffer (0.05 mol/L, pH 7.4) just before use, and the absorbance at 734 nm was adjusted to 0.70. + -. 0.02 to prepare an ABTS working solution.
Preparing 5-60 μ g/mL solution of iso-lariciresinol with methanol, adding 150 μ L iso-lariciresinol solution into 2.85mL ABTS working solution, mixing, reacting at 25 deg.C in dark environment for 10min, and detecting absorbance A with ethanol at 734 nm as blanksample. The absorbance A of a negative control was determinedcontrolThe clearance is then calculated according to the formula.
ABTS free radical clearance = [ (A)control-Asample)/Acontrol]× 100%。
Determination of ABTS free radical scavenging IC of isolariciresinol50The value is 0.1712.
ABTS free radical scavenging IC of Trolox50The value is 0.4712.
Claims (4)
1. Use of isolariciresinol in preparing hypoglycemic agent is provided.
2. Use of isolariciresinol in preparing antioxidant medicine is provided.
3. A preparation method of isolariciresinol is characterized by comprising the following steps:
① soaking dried herba Ceratophylli in ethanol, mixing extractive solutions, distilling under reduced pressure to obtain total ethanol extract, dispersing the total ethanol extract in distilled water, sequentially extracting with petroleum ether and ethyl acetate to obtain petroleum ether extract and ethyl acetate extract;
② subjecting the ethyl acetate part extract obtained in step ① to silica gel column chromatography, eluting with petroleum ether-ethyl acetate solvent system according to gradient of 100: 1-0: 100 (v/v), collecting fractions per 200 mL and detecting by TLC, and mixing the same fractions to obtain 6 fractions Fr.1-Fr.6;
③ separating the fourth major fraction Fr.4 from step ② by Sephadex LH-20 Sephadex column chromatography (solvent system chloroform: methanol = 1: 1, V/V) to obtain four sub-fractions Fr.4-1, Fr.4-2, Fr.4-3 and Fr.4-4;
④ Fr.4-3 fraction of step ③ was separated by HPLC using mobile phase acetonitrile-water (35: 75, v/v) to obtain isolariciresinol.
4. The method for preparing isolariciresinol according to claim 3, wherein the step ① is carried out by soaking in ethanol at room temperature for 2-4 times, each time for 2.5-4 days.
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2023070480A1 (en) * | 2021-10-29 | 2023-05-04 | 海南师范大学 | Halimane diterpenoid in leucas zeylanica, and preparation method and application thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102526165A (en) * | 2010-12-07 | 2012-07-04 | 中国医学科学院药物研究所 | Rhodiola effective fractions, preparation method, drug composition and uses thereof |
CN103102252A (en) * | 2012-10-09 | 2013-05-15 | 东北林业大学 | Method for separating and purifying (+)-isolariciresinol and (-)-lariciresinol from folium isatidis |
CN104004034A (en) * | 2014-05-14 | 2014-08-27 | 中国科学院华南植物园 | Method for preparing secoisolariciresinol 9'-O-beta-xyloside |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102526165A (en) * | 2010-12-07 | 2012-07-04 | 中国医学科学院药物研究所 | Rhodiola effective fractions, preparation method, drug composition and uses thereof |
CN103102252A (en) * | 2012-10-09 | 2013-05-15 | 东北林业大学 | Method for separating and purifying (+)-isolariciresinol and (-)-lariciresinol from folium isatidis |
CN104004034A (en) * | 2014-05-14 | 2014-08-27 | 中国科学院华南植物园 | Method for preparing secoisolariciresinol 9'-O-beta-xyloside |
Non-Patent Citations (3)
Title |
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HUI-CHI HUANG等: "Hypoglycemic Constituents Isolated fromTrapa natans L. Pericarps", 《J. AGRIC. FOOD CHEM.》 * |
JIANG-TAOZHOU等: "Phenolic Compounds from the Roots of Rhodiola crenulata and Their Antioxidant and Inducing IFN- γ Production Activities", 《MOLECULES》 * |
LI-MEI DONG等: "Phenolics from Mikania micrantha and Their Antioxidant Activity", 《MOLECULES》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2023070480A1 (en) * | 2021-10-29 | 2023-05-04 | 海南师范大学 | Halimane diterpenoid in leucas zeylanica, and preparation method and application thereof |
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