Aconite napelline type diterpene alkaloid acylate, synthesis and use thereof

A technology of alkaloid acylate and diterpene, applied in the direction of chemicals, applications, and biocides for biological control, which can solve the problems of unreported insecticidal activity

Inactive Publication Date: 2009-05-27
SOUTHWEAT UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the research on the structural modification of diterpene alkaloids has been carried out for many years, they mainly focus on their analgesic activity, antitumor activity, antiarrhythmic activity and other medicinal activities, but there is no research on their insecticidal activity. to report

Method used

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  • Aconite napelline type diterpene alkaloid acylate, synthesis and use thereof
  • Aconite napelline type diterpene alkaloid acylate, synthesis and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Dissolve 46.6mg of songuoling in 1ml of pyridine, then add 0.5ml of acetic anhydride dropwise, and stir at room temperature for 20 hours. Adjust the pH to 9 with saturated sodium carbonate solution. After extraction with chloroform, the chloroform layer was washed three times with water and saturated brine, dried, and distilled under reduced pressure to obtain 53 mg of 1-0-acetyl-15-0-acetyl-songuoling.

[0010] The product structure was confirmed by mass spectrometry, EI-Ms m / z: 442 (M + );

[0011] NMR testing, 1 HNMR (CDCl 3 ) (ppm): 5.64, 5.25 (each1H, s, extracyclic double-bonded hydrogen), 2.11, 2.03 (each3H, s, COCH 3 ), 3.15 (3H, t, NCH 2 CH 3 ), 0.75 (3H, s, 18-CH 3 );

[0012] NMR testing, 13 CNMR (CDCl 3 )δ: 208.8, 170.6, 170.3, 145.2, 112.9, 50.6, 13.5 (NCH 2 CH 3 ).

Embodiment 2

[0014] Dissolve 37.9 mg of songuoling in 1 ml of pyridine, then add 0.5 ml of propionic anhydride dropwise, and stir at room temperature for 20 hours. The saturated sodium carbonate solution was used to adjust the pH to 9. After extraction with chloroform, the chloroform layer was washed three times with water and saturated saline, dried, and distilled under reduced pressure to obtain 38.1 mg of a propionylation mixture of sorgolin. Put on a silica gel column and elute with petroleum ether / acetone=5:1 to obtain 28.3 mg of 1-0-propionyl-15-0-propionyl sorgoline.

[0015] The product structure was confirmed by mass spectrometry, EI-Ms m / z: 470.3 (M + );

[0016] NMR testing, 1 HNMR (CDCl 3 )(ppm): 5.66(1H, s), 5.25(1H, d), 5.03(1H, dd), 4.99(1H, s), 2.75(1H, q), 2.58(1H, m), 2.53(1H , d), 2.44(1H, m), 2.30(3H, m), 2.21(1H, d), 2.18(1H, m), 2.13(3H, s), 2.02(1H, m), 1.94(1H, m), 1.60(4H,m), 1.43(1H,dd), 1.41(1H,d), 1.23(3H,t), 1.19(3H,t), 1.15(3H,t)

Embodiment 3

[0018] Determination of insecticidal activity: Weigh a certain mass of the original drug with an analytical balance (0.0001 g), add a solvent (DMF) containing 0.1% Tween-80, and prepare a 5% preparation. Take a certain amount of preparation, add distilled water (acetone for spot method dilution) to dilute and prepare the medicinal solution for measuring the required concentration, and the general sieve concentration is 500mg / L. Cut off both ends of broad bean leaves, put the back side up on a small piece of cotton, put it in a plastic petri dish, add a small amount of water, and pick up alfalfa aphids to produce nymphs. After 24 hours, the adult aphids were removed, and after continuing to cultivate for 2 days, the leaves were fully soaked in the medicinal solution for 5 seconds, then placed on cotton again, and dried naturally. Carbosulfan (10 mg / L) and blank CK were used as controls. After 24 hours, the results showed that 1-0-acetyl-15-0-acetyl sorgoline and 1-0-propionyl-...

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Abstract

The invention discloses preparation and application of acylate (a compound structure is shown in figure) of natural napelline type diterpenoid alkaloids in Aconitum plant aconite, which belong to the technical field of medicine synthesis of medicine and pesticide. The method for preparing the acylate of the napelline type diterpenoid alkaloids comprises the following steps: a napelline type diterpenoid alkaloid compound in aconite is taken as a raw material to be stirred to react with an acylating reagent, namely acyl chloride or acid anhydride at a temperature of between 0 and 40 DEG C, the pH value is adjusted to be between 8 and 10 after the reaction is finished, the reduced pressure distillation is performed after the extraction, and the acylate of the napelline type diterpenoid alkaloids is obtained through recrystallization or column chromatography. The acylate of the napelline type diterpenoid alkaloids can be applied to agricultural insecticides, and can also be used for the development of anti-tumor drugs, anti-inflammatory analgesics, antiarrhythmic drugs and so on. In a formula, R1 and R2 are hydrogen, hydroxy or acyl (at least one of R1 and R2 is acyl); and R3 is alkyl containing 1 to 4 carbon atoms.

Description

(1) Technical field [0001] The invention relates to a synthesis method and an application of napiline-type diterpene alkaloid acylate in aconite, and belongs to the technical field of medicine and pesticide synthesis. (2) Technical background [0002] Napiline-type diterpene alkaloids are a class of natural compounds in the genus Aconitum of the Ranunculaceae, mainly including Songguolin, Aconitine, 12-Epi-Aconitine, Xingguoaconitine and Jungerine, etc. . Among them, song Guoling is an important active ingredient in the root of Aconitum carmichaeli Debx. (Aconitum carmichaeli Debx.), a traditional Chinese medicine, and mostly exists in the form of hydrochloride in Aconitum carmichaeli Debx. According to the records of "Shen Nong's Materia Medica", aconite has the effects of restoring yang and rescuing the adversity, dispelling cold and dispelling wind, but it is listed as an inferior medicine because of its great toxicity. Modern pharmacological studies have shown that dit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/22A01N43/42A01P7/00A61K31/439A61P29/00A61P9/06A61P35/00
Inventor 侯大斌杨海君王惠袁小红贺新生马林徐春霞
Owner SOUTHWEAT UNIV OF SCI & TECH
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