Morinda officinalis iridoid compounds with anti-inflammatory activity, preparation method and application thereof

A technology for iridoids and iridoid glycosides is applied in the field of Morinda officinalis iridoid compounds and their preparation, which can solve the problems of non-utilization, pollution, waste of resources and the like, and reduce inflammatory response. , the effect of reducing environmental pollution problems and easy preparation

Active Publication Date: 2021-09-07
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when Morinda officinalis is harvested, usually only the underground roots are dug out, and a large amount of above-ground parts are all discarded, which has not been rationally utilized, resulting in waste of resources and environmental pollution to a certain extent.
There are few reports on the aerial parts of Morinda officinalis at home and abroad

Method used

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  • Morinda officinalis iridoid compounds with anti-inflammatory activity, preparation method and application thereof
  • Morinda officinalis iridoid compounds with anti-inflammatory activity, preparation method and application thereof
  • Morinda officinalis iridoid compounds with anti-inflammatory activity, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Example 1 Extraction and Separation of Partial Iridoid Glycoside Compounds in Morinda officinalis

[0065] The stems and leaves of the aerial part of Morinda officinalis were collected from July to August 2019 at the GAP planting base of Morinda officinalis in Deqing County, Zhaoqing City, Guangdong Province. It was identified as Morinda officinalis by researcher Ding Ping of Guangzhou University of Traditional Chinese Medicine. The stems and leaves of the aboveground part of Morinda officinalis How, the certificate specimen (20190731001) is deposited in the Department of Traditional Chinese Medicine Resources, Guangzhou University of Traditional Chinese Medicine.

[0066] 1. Experimental method

[0067] 1. Extraction and separation of compounds

[0068] After drying the aboveground part of Morinda officinalis, take 10.0kg and cut it off, extract it three times with 95% ethanol (10L×3), seven days each time, and reflux the residue with 95% ethanol again to fully extrac...

Embodiment 2

[0074] The structural identification of embodiment 2 iridoids

[0075] 1. Structural identification of compound Ⅰ

[0076] Compound I is a colorless oil, Ion peak m / z[M+Na] given by HRESIMS mass spectrometry data + 279.1451 (calcd for C 13 h 20 o 5 Na, 279.1203) binding 13 C NMR data can determine that its molecular formula is C 13 h 20 o 5 , with an unsaturation of 4. 1 H NMR shows 1 aldehyde group δ in the low field region H 9.73(1H,s,H-8); 1 pair of double bond δ H 5.99(1H, dd, J=2.4, 5.6Hz, H-3), δ H 5.80 (1H, dd, J=2.4, 5.6Hz, H-2); 1 butoxyl δ H 4.13(1H,m,H-10a), 4.04(1H,m,H-10b), 1.62(2H,m,H-11), 1.37(2H,m,H-12) and 0.92(3H,t, J=7.2Hz, H-13). From 13 C NMR spectrum, DEPT spectrum and HSQC spectrum show 13 carbon signals, including 1 aldehyde group δ C 200.4 (C-8); 1 ester carbonyl δ C 173.5(C-9); 1 pair of double bond δ C 133.4(C-2), 137.2(C-3); 1 continuous oxygen quaternary carbon δ C 84.9 (C-1); 2 oxymethylene signals δ C 68.2 (C-6), 65.1 ...

Embodiment 3

[0094]Example 3 Anti-inflammatory activity experiment of iridoids

[0095] In this example, the in vitro anti-inflammatory activity research experiment of compounds I (officinaloside E) and II (officinaloside F) on LPS-induced RAW 264.7 cells was carried out.

[0096] 1. Experimental materials and instruments

[0097] Clean bench (Suzhou Antai Air Technology Co., Ltd.); constant temperature CO 2 Cell incubator (Germany Heraeus); electric constant temperature water bath (Shanghai Boxun Industrial Co., Ltd.); inverted microscope (Germany LEICA); PAGE vertical electrophoresis instrument (BIO-RAD, USA); fluorescence imaging system, Trizol lysate (Tiangen Biochemical Technology); ultra-micro spectrophotometer (IMPLEN, Germany); 4°C refrigerated centrifuge (Hettich, Germany); metal bath Heater (Hangzhou Aosheng Instruments); PBS phosphate buffer, nitric oxide kit, BCA protein quantification kit, SDS cell lysate, primary antibody diluent, PMSF protease inhibitor, 5 × loading buffer...

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Abstract

The invention discloses morinda officinalis iridoid compounds with anti-inflammatory activity, a preparation method and application thereof, specifically iridoid compounds with anti-inflammatory activity, wherein the structural formulas of the iridoid compounds are respectively shown as formulas I and II. According to the invention, two new iridoid compounds are extracted and prepared from the ground part of morinda officinalis for the first time, the chemical structures and physicochemical properties of the two iridoid compounds are confirmed through modern spectroscopy means such as HR-ESIMS, NMR, IR, UV and the like, and the pharmacological activities of the two new iridoid compounds are verified through cell experiments; and the two novel iridoid compounds both show an excellent anti-inflammatory effect, have an obvious inhibition effect on NO generation, can effectively reduce the expression of proinflammatory factors iNOS, COX-2, TNF-alpha, IL-1beta and IL-6, can reduce the inflammatory reaction caused by the overexpression of inflammatory factors, and can be used as a lead compound for developing novel anti-inflammatory drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and more specifically, relates to Morinda citrifolia iridoids with anti-inflammatory activity and its preparation method and application. Background technique [0002] Morinda officinalis is the dried root of Morinda officinalis How, a plant belonging to the genus Morinda officinalis in the family Rubiaceae. , impotence and nocturnal emission, etc. There are many types of active ingredients in Morinda officinalis, mainly oligosaccharides, polysaccharides, iridoids, anthraquinones, etc. Modern pharmacological studies have shown that Morinda officinalis has a wide range of biological activities such as anti-depression, anti-oxidation, anti-osteoporosis, anti-inflammation, anti-aging, and improving immunity. At the same time, Morinda officinalis is also an important health food with high medicinal value. It is known as "Korean ginseng in the north and Morinda officinalis in the south". . [000...

Claims

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Application Information

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IPC IPC(8): C07C69/757C07C67/48C07C67/56C07C67/58C07H17/04C07H1/06A61P29/00A61K31/215A61K31/7048A23L33/105A23L33/125
CPCC07C69/757C07C67/48C07C67/56C07C67/58C07H17/04C07H1/06A61P29/00A61K31/215A61K31/7048A23L33/105A23L33/125C07C2601/10C07B2200/07A23V2002/00A23V2200/30A23V2250/21A23V2250/30A23V2300/02A23V2300/14A23V2300/38Y02A50/30
Inventor 丁平蔡苗苗赵志敏杨得坡
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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