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Icariside compound, preparation method thereof, and application thereof

a technology of icariside and compound, applied in the field of icariside compound, can solve the problems of limiting application, easy degradation, people getting sick, etc., and achieve the effects of improving or inhibiting human immunity, low toxicity and side effects, and safe us

Inactive Publication Date: 2018-07-19
FOSHAN GOLDEN HEALTH TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The inventors discovered two compounds, icariside I and icariside C, in epimedium that can promote human cells to produce the important immune protein interferon-γ (IFN-γ). This suggests that these compounds may have important applications in improving human immunity. These compounds were tested in various tests and shown to be safe for use with low toxicity and side effects. This patent shows that ikariside compounds can be used for the prevention and treatment of infective diseases and tumor progression and metastasis. It also shows the potential to develop a new pharmaceutical for cellular immune therapy.

Problems solved by technology

When the immunity (antibodies or cytokines etc.) produced by human immune system is not sufficient to fight against the disease causative factors, people get sick.
However, these are specific for certain diseases which greatly limit their applications.
In addition, they are easy to be degraded which have a short half-life and poor bioavailability and which are difficult to be large-scale synthesized, separated and purified.
So far, attempts to find small molecular compounds with good effects on enhancing immunity are not yet successful.
However, systematic studies on the separation of active components therein are rare, in particular that on icariside I and icariside C due to their extremely low content (while its homologue, icariin, has higher content) leading to difficulty in conducting an effective research, let alone industrial application.

Method used

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  • Icariside compound, preparation method thereof, and application thereof
  • Icariside compound, preparation method thereof, and application thereof
  • Icariside compound, preparation method thereof, and application thereof

Examples

Experimental program
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Effect test

example 1

[0035]Preparation of Icariside I

[0036](1) Preparation of Icariside I by Separation from Epimedium.

[0037]According to the method reported by Li Wenkui, et al. (Herbal, 1995, 26 (9), 453-455), icariside I was separated and purified with a content of more than 95% from the whole plant of epimedium. The chemical structure of the product was characterized by 1H NMR, Mass spectroscopy, and other instrumentations.

[0038](2) Preparation of Icariside I by Enzymatic Conversion of Icariin as Raw Material.

[0039]A. Preparation of icariin: According to the method reported by Li Wenkui, et al., (Herbal, 1995, 26 (9), 453-455), icariin was separated and purified with a content of more than 95% from the whole plant of epimedium. The chemical structure of the product was characterized by 1H NMR, Mass spectroscopy, and other instrumentations.

[0040]B. Preparation of icariside I:

2 g of icariin (purity 98%) was dissolved in a pH6.8 phosphate buffer, and then 1 g of immobilized rhamnosidase was added. The ...

example 2

[0041]Preparation of Icariside C

[0042](1) Preparation of Icariside C by Separation from Epimedium.

[0043]According to the method reported by Li Wenkui, et al. (Herbal, 1995, 26 (9), 453-455), icariside C with a content of more than 95% was obtained after separation and purification from the whole plant of epimedium. The chemical structure of the product was characterized by 1H NMR, Mass spectroscopy, and other instrumentations.

[0044](2) Preparation of Icariside I from Epimedoside A as Raw Material by Enzymatic Conversion.

[0045]A. Preparation of epimedoside A: epimedoside A is one of the components with a higher content in epimedium. According to the method reported by Xu Sui Xu et al. (Herbs, 1981, 14, 24-26), epimedoside A with a content of more than 95% was obtained by separation and purification from the whole plant of epimedium. The chemical structure of the product was characterized by 1H NMR, Mass spectroscopy, and other instrumentations.

[0046]B. Preparation of icariside C: Ica...

example 3

[0047]Preparation of Icariside Compounds Based on Modification of the R1 Group

[0048]Using icariin as raw material, the OH group of R1 was selectively transformed into another group by a chemical method (the process does not affect glycosyl groups present in the molecule). Then, by applying the method in Example 1 (2), the R2 Rha group of the modified icariin was removed with an enzymatic method to obtain the desired icariside compounds.

[0049]Preparation Example: 2 ml chloroform was added to 50 mg icariin followed by addition of 10 mg iodomethane (CH3I) and addition of 10 mg silver oxide (Ag2O). Then, the solution was stirred at room temperature for 24 hours. After reaction, chloroform was removed by rotary evaporation. The residue was re-dissolved with 95% ethanol and was purified by column chromatography (silica gel column) to obtain the product with R1 being a methoxy group. Finally, by applying the method in Example 1 (2), the R2 Rha group in the modified icariin was removed with...

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Abstract

An icariside compound as shown in Formula I wherein the compound is a natural chemical component in the traditional Chinese herbal epimedium or a chemically modified or a totally synthetic product based on the natural component. The compound can be used for preparing pharmaceuticals, health care products, cosmetic and skin care products and the like for improvement of immunity in a human body.

Description

REFERENCE TO RELATED APPLICATION[0001]This application claims the priority of Chinese patent application No. 201510264195.5 “ICARISIDe COMPOUND, PREPARATION METHOD THEREOF, AND APPLICATION THEREOF” filed on May 20, 2015, hereby incorporated by reference in its entirety.BACKGROUND[0002]Human immunity refers to the ability of the body to protect against causative factors outside or within host cells from infection or invasion, i.e. the ability of the body to maintain a normal and stable environment within the body. In the environments where people live, air, water, food, and most items we contact in daily life, for example, contains a variety of harmful microorganisms such as bacteria, viruses, mycoplasma, chlamydia, fungi and other pathogens (causative factors outside a host cell). Human body may also be affected by the environmental changes, the emergence of a latent virus or bacteria in the host cell, or infection or invasion of cancer cells produced by gene mutation and the like (...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07H17/07C07H1/00C12P19/60
CPCC07H17/07C07H1/00C12P19/60A61K8/602A61K9/0014A61Q19/00A61P31/06A61P31/12A61P35/00A61P37/04C07H1/08G01N33/5055A61K8/498A61K8/60A61K9/0019A61K9/06A61K9/107A61K9/20A61K31/7048G01N33/53
Inventor GU, LIANQUANWU, CHANGYOUZHOU, JINLINLU, YUJINGOU, TIANMIAOHUANG, BAOHUALIN, LIWEI
Owner FOSHAN GOLDEN HEALTH TECH CO LTD
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