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Pinane monoterpene compound, and preparation method and application thereof

A technology of compounds and compound structural formulas, applied in the field of pinane-type monoterpenoids and their preparation, achieving the effects of high efficiency, precise pharmacological effects, and simple extraction and separation methods

Inactive Publication Date: 2016-04-13
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there have been related researches on the medicinal effects of the root bark of Moutan grandiflora, but due to the variety of chemical components in the root bark of Moutan grandiflora, there have been no relevant reports on the research on its active ingredients. Phase silica gel column chromatography, reverse phase (MCI-Gel) column chromatography, gel (SephadexLH-20) column chromatography, high-performance liquid chromatography and other technologies were used to separate and purify the ethyl acetate extract components of the root bark of Peony Dahua, 23 monomeric compounds were obtained, and their structures were confirmed by ultraviolet spectrum, infrared spectrum, mass spectrum, nuclear magnetic resonance spectrum and literature reports, including 7 monoterpene compounds, 3 monoterpene glycoside compounds, 8 phenolic compounds, There are 3 phenolic glycosides, 1 alkaloid and 1 triterpenoid, including 4 new compounds and 19 known compounds, all of which were isolated for the first time from the Tibetan peony.

Method used

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  • Pinane monoterpene compound, and preparation method and application thereof
  • Pinane monoterpene compound, and preparation method and application thereof
  • Pinane monoterpene compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Take the dry root bark of Tibetan peony, crush it and accurately weigh 10kg, add 95% ethanol according to the ratio of root bark to solvent 1:10 (W / V), extract at room temperature for 24 hours, filter with suction, repeat three times, 50 °C and concentrated under reduced pressure, then the total extract was extracted with ethyl acetate, and the extract was concentrated under reduced pressure at 50 °C to obtain 356 g of component dry powder A.

[0024] Weigh 356g of dry powder A and mix it with 1.5kg of polyamide, carry out medium-pressure liquid chromatography, the reverse phase column packing material is MCI-Gel, use 20% volume concentration of methanol aqueous solution to elute to obtain 51g of component B, use silica gel Mix the sample and carry out silica gel column chromatography. After eluting with a mixture of petroleum ether and ethyl acetate with a volume ratio of 6:4, repeat the silica gel column chromatography and use a mixture of petroleum ether / isopropanol w...

Embodiment 2

[0025] Embodiment 2 monomer compound structure identification

[0026] 1) Spectrum test

[0027] The isolated compound was tested for purity by analytical liquid chromatography, and if there was no ultraviolet absorption, it could not be detected by analytical liquid chromatography, and was tested by TLC. According to the polarity of the monomer compound, a corresponding deuterated solvent was selected for dissolution, and NMR was used for detection, and tetramethylsilane (TMS) was used as an internal standard. New compounds need to be pressed into KBr tablets for IR identification of the functional group types contained in the compound structure; at the same time, an appropriate amount of compound is taken and dissolved in a corresponding polar solvent for UV detection to determine the type of functional group with UV absorption in the compound structure. The molecular weight of the compound is estimated according to ESI-MS, and the molecular weight, molecular formula and de...

Embodiment 3

[0038] Example 3 Determination of antifungal activity

[0039] Microsporum gypsumoidis is a kind of filamentous fungus that can cause superficial skin ringworm, which can cause tinea corporis, jock itch, onychomycosis, tinea capitis, etc. It is a common superficial pathogenic fungus in clinical practice. In recent years, the role of medicinal plants in the treatment of skin diseases has attracted much attention. It is an important research direction to seek and use the active ingredients in natural medicinal plants to design new non-toxic drugs for the treatment of skin diseases. The minimum inhibitory concentration (Minimum inhibitory concentration, MIC) is an important index to measure the activity of antibacterial drugs. The test tube drug base method can not only conveniently interpret the MIC value, but also is simple, economical and easy to operate.

[0040] In this experiment, the activity of the isolated monomeric compounds was studied with reference to the "Spore-form...

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PUM

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Abstract

The invention discloses a pinane monoterpene compound. The structural formula of the compound is shown in the description, the molecular formula of the compound is C10H16O3, the unsaturation degree is 3, and an ultraviolet spectrum shows the maximum absorption wavelength of the compound is 203nm. The invention also relates an extraction and separation method of the compound. The method comprises the following steps: extracting with ethyl acetate, separating the obtained extract liquid, and purifying the separated extract liquid to obtain the monomer compound. The compound has antifungal activity, provides a lead compound for developing antifungal medicines, and is of great significance to develop new uses of natural products and plant drugs.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, and in particular relates to a pinane-type monoterpene compound and a preparation method and application thereof. Background technique [0002] Tibetan big flower yellow peony (Paeonialudlowii) is Ranunculaceae (Ranunculacea), Paeonia (Paeonia), peony group (Sect.MoutanDC.) plant. It only grows in the open valleys of the Yarlung Zangbo River and forest edge bushes on hillsides at an altitude of 2500-3500m in Milin, Nyingchi, Bomi, Zayu, Longzi and other counties in Tibet, my country. The number is very small and is decreasing year by year. It is unique to Tibet. endangered protected plants. According to the local chronicles, Tibetans have used the root bark of Tibetan big flower yellow peony to treat gynecological diseases, cardiovascular and cerebrovascular diseases, and dermatophytosis as early as hundreds of years ago. [0003] At present, there have been related researches on the m...

Claims

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Application Information

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IPC IPC(8): C07C49/513C07C45/78A61P31/10
CPCC07C45/78C07C49/513
Inventor 赵丹丹蒋帅李建平曾伟民曲宏悦蒋丽丽黄悦
Owner HEILONGJIANG UNIV
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