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Sesterterpene compound and preparation method and application thereof

A technology of disesquiterpenes and compounds, which is applied in the field of natural medicinal chemistry and achieves the effects of good anti-prolyl endopeptidase activity, fresh and pure aroma, and good angiogenesis inhibitory activity

Active Publication Date: 2012-09-12
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been reported in the literature that the leaves and flowers of C. coccinea in this genus are rich in essential oils, mainly sesquiterpene β-Caryophyllene (44.1-53.2%), Germacrene D (7.0-15.8%), Cadina- 1-4-diene (11.1-12.4%), Germacrene D-4-ol (1.8-12.2%), α-Humulene (3.7-8.7%) and Caryophyllene oxide (1.0-5.7%), the rest of the plants have no chemical research to report

Method used

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  • Sesterterpene compound and preparation method and application thereof
  • Sesterterpene compound and preparation method and application thereof
  • Sesterterpene compound and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Extraction, separation and purification of compound 1-34 of the present invention:

[0040] Dry the leaves (15 kg) of the genus Torchina plant in the shade, crush them to 30 meshes, extract them with n-ethane at room temperature for 3 times (45 L each time, 24 h), combine the extracts, and concentrate the extracts under reduced pressure to obtain the leaching solution. Cream 210 g. The extract was dissolved in an appropriate amount of chloroform / acetone, and then mixed with silica gel (200-300 mesh), and then 1.5 kg of silica gel (200-300 mesh) was used for column chromatography to divide the crude fraction, and petroleum ether / chloroform (1:0 — 0:1) and chloroform / acetone (1:0 — 0:1) for gradient elution to obtain 8 major fractions. A total of 45 g of the chloroform and chlorine / propane (9:1) fractions were subjected to medium-pressure liquid phase MCI column chromatography, and gradient elution was performed with acetone / water (70% — 100%), of which 80% and 90% were ...

Embodiment 2

[0043] Physical and Spectroscopic Data of Compounds 1-34 of the Invention:

[0044] Compound 1: The compound is a colorless oil: [α] D 23.3 = +0.10 (c = 0.20, MeOH); UV (MeOH) λ max (log ε): 211 (2.93) nm; IR (KBr) ν max : 3440.6, 2957, 2930, 2869, 1686, 1630, 1380, 1025 cm -1 ; EI: m / z (%) 414 ([M] + , 35), 179 (30), 95 (54), 83 (100); HR-EI-MS: m / z 414.2397 (calcd for C 25 h 34 o 5 , 414.2406); 1 H and 13 See Table-1 and Table-2 for C NMR data.

[0045] Compound 2: This compound is colorless and transparent massive crystals: [α] D 26.3 = +1.07 (c = 0.15, MeOH); UV (MeOH) λ max (log ε): 217 (2.66) nm; IR (KBr) ν max : 3442, 2956, 2927, 2868, 1687, 1629, 1454, 1027, 1025, 725 cm -1 ; EI: m / z (%) 414 ([M] + , 25), 178 (25), 95 (100), 83 (75), 81 (51); HR-EI-MS: m / z 414.2398 (calcd for C 25 h 34 o 5 , 414.2406); 1 H and 13 See Table-1 and Table-2 for C NMR data.

[0046] Compound 3: This compound is white powder: [α] D 14.1 = +1.20 (c = 0.15, MeOH); UV (...

Embodiment -3

[0129] Antifeedant activity detection of the compound of the present invention:

[0130] The antifeedant activity of the compound of the present invention against beet armyworm (Spodoptera exigua) and cotton bollworm (Helicoverpa armigera) was determined by using the selective antifeedant activity assay method. Before the activity test, the larvae whose growth was relatively consistent at about the third instar were starved for 4-5 hours. The leaves of Chinese cabbage (Brassica chinensis) with consistent growth were selected, rinsed, and punched with a hole punch (1.1 cm in diameter) to make round leaves (leaf butterflies). The compound of the present invention is configured into 5 different concentration gradients with acetone, and 10 μl is dropped on the leaf butterfly, and dried to treat the leaf butterfly; for the control leaf butterfly, 10 μl of acetone solution is directly dropped on the leaf butterfly, and dried , and then put 2 treatment leaf butterflies and 2 control...

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Abstract

The invention discloses a sesterterpene compound 1-34 and a medicinal composition taking the compound as an active ingredient. A preparation method of the sesterterpene compound 1-34 comprises the following steps of: performing direct cold soaking or thermal reflux extraction on leaves or flowers or stems of labiatae tripterygium hypoglaucum plant with an organic solvent, i.e., petroleum ether or n-hexane or cyclohexane or chloroform or acetone or methanol or ethanol; or performing cold soaking or thermal reflux extraction on the organic solvent, and extracting with ethyl acetate to obtain a total extract; and repeatedly performing column chromatography on the total extract to obtain the compound. The compound is applied to preparation of an anti-angiogenesis agent, an anti-prolyl endopeptidase agent, an antibacterial agent, an anti-feedant and a flavor: the compound has high antibiotic activity when being applied to a substrate or a group in an amount of 10-1,000muM and being optionally combined with a carrier and / or a medium; the compound has high antifeedant activity when being applied to a substrate or a group in an amount of 0.005-10muM / cm<2> and being optionally combined with a carrier and / or a medium; and the compound has clear flavor and high hair permeability, can be used for improving the hair flavor when used for blending, has the characteristic of unique flavor, is clear and pure, can be used for covering bad flavors of surfactant substrate raw materials, and is safe for a long time.

Description

Technical field: [0001] The invention belongs to the field of natural medicinal chemistry, and specifically relates to a new class of sesquiterpene compounds, a preparation method thereof, a pharmaceutical composition using the compound as an active ingredient, and its role in inhibiting angiogenesis, anti-prolyl Endopeptidase, antibacterial, antifeedant and fragrance applications. technical background: [0002] There are about 6 species of Colquhounia spp. in the family Lamiaceae. There are 5 species and 4 varieties in my country. They are mainly distributed in western to central Yunnan and southeastern Tibet. In addition, they are also found in Sichuan, Guizhou, western Guangxi and western Hubei. Small amount of distribution. It has been reported in the literature that the leaves and flowers of C. coccinea in this genus are rich in essential oils, mainly sesquiterpene β-Caryophyllene (44.1-53.2%), Germacrene D (7.0-15.8%), Cadina- 1-4-diene (11.1-12.4%), Germacrene D-4-ol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08C07D493/20C07D493/10C07D307/93C07D307/46A61K31/343A61K31/341A61K31/365A61P35/00A61P9/00A01N43/90A01N43/12A01N43/08A01P7/04A01P3/00C11B9/00
Inventor 黎胜红李春环
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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