Two novel iridoid glycoside compounds, preparation method therefor and application thereof

A technology for iridoid glycosides and compounds is applied to two new iridoid glycoside compounds and their preparation fields, which can solve problems such as limiting wide application and achieve the effect of good medicinal prospect.

Inactive Publication Date: 2015-09-09
江西省药品检验检测研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many antithrombotic drugs have potential adverse reactions or drug resistance, mainly manifested as nausea, vo

Method used

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  • Two novel iridoid glycoside compounds, preparation method therefor and application thereof
  • Two novel iridoid glycoside compounds, preparation method therefor and application thereof
  • Two novel iridoid glycoside compounds, preparation method therefor and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Extraction and separation method of 7-O-E-p-coumaroyl-8-epi-carinaeic acid and 7-O-E-p-coumaroyl-garinia glycoside in the leaves of Aurantia japonica:

[0045] Take 9.6 kg of dried leaves of Aurora nudiflora, reflux extraction with 8 times the amount of 80% ethanol for 3 times, each time for 2 hours, combine the extracts, and use a rotary evaporator to recover the ethanol under reduced pressure under the condition of less than 50°C to obtain Extract 1.8kg; Suspend the extract in water to obtain an aqueous suspension of extract, extract the aqueous suspension of extract four times with ethyl acetate, then extract the aqueous extract of extract with n-butanol and mix it with ethyl acetate. Extract the extract water suspension after the suspension for three times, combine the extracted n-butanol layer liquid, recover n-butanol as a solvent for the n-butanol layer under reduced pressure at a temperature lower than 50°C, and obtain n-butanol layer immersion Cream ...

Embodiment 2

[0048] Example 2: Structural Identification of Two New Iridoid Glycosides in Auranthus nudica

[0049] 1. 7-O-E-p-coumaroyl-8-epi-carpynic acid: white amorphous powder, easily soluble in organic reagents such as acetone, n-butanol, pyridine, methanol, etc., with a melting point of 179-180°C and optical activity [ α] 20 D -58.8 (c 0.08, MeOH); UV (CH 3 OH)λ max 288nm and 312nm, HRESIMS gives the molecular weight as m / z521.1656[M–H] – . Molecular formula is C 25 h 30 o 12 ; 1 H and 13 The C NMR data are shown in Table 1, and at the same time, by measuring the two-dimensional H-H correlation spectrum ( 1 H- 1 H COZY), H-C correlation spectrum (HSQC), H-C long-distance correlation spectrum (HMBC) and rotating coordinate system NOE (NOESY), the signal assignments of all carbon atoms and hydrogen atoms and the chemical structure of the compound were determined. The chemical structural formula is as follows:

[0050]

[0051] Table 1 The H and C spectra data of 7-O-E-...

Embodiment 3

[0060] Example 3: Anti-arachidonic acid-induced platelet aggregation activity test of two new iridoid glycoside compounds

[0061] Inhibition rate (%)=(absorbance value of monomer group-absorbance value of inducer group) / absorbance value of monomer group

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Abstract

The invention discloses two novel iridoid glycoside compounds, a preparation method therefor and an application thereof. In the two novel iridoid glycoside compounds, the chemical name of the first iridoid glycoside compound is 7-O-E-p-coumaroyl-8-epi-loganic acid; the chemical name of the second iridoid glycoside compound is 7-O-E-p-coumaroyl-gardoside. The preparation method for the two new iridoid glycoside compounds takes Callicarpa nudiflora Hook. dried leaves as raw materials and comprises the steps of 1) preparing extract, 2) preparing n-butanol extract, and 3) preparing 7-O-E-p-coumaroyl-8-epi-loganic acid and 7-O-E-p-coumaroyl-gardoside. The chemical structural formulae of 7-O-E-p-coumaroyl-8-epi-loganic acid and 7-O-E-p-coumaroyl-gardoside are a formula (I) and a formula (II) (which are shown in the description) respectively. The chemical-physical properties and the optical activities of 7-O-E-p-coumaroyl-8-epi-loganic acid and 7-O-E-p-coumaroyl-gardoside are disclosed; the two novel iridoid glycoside compounds have a function of remarkably resisting arachidonic acid induction platelet aggregation, and can be used for preparing antithrombotic medicines.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to two new iridoid glycoside compounds and their preparation method and application. Background technique [0002] Callicarpa nudiflora Hook.ex Arn. is a plant of the genus Callicarpa L. in the family Verbenaceae. It is mainly produced in Hainan, Guangdong, Guangxi, Jiangxi and other places in my country. The stems and leaves or the whole plant are used as medicine . Zizhu leaves have the functions of antibacterial and hemostasis, anti-inflammatory and detoxification, dissipating stasis and swelling, dispelling wind and dampness, and enhancing immunity. It is often used to treat purulent inflammation, acute infectious hepatitis, tuberculosis and hemoptysis, gastrointestinal bleeding, respiratory and digestive tract bleeding, traumatic bleeding embolism, topical treatment of burns, scalds and traumatic bleeding and other diseases. [0003] Thrombosis is a common and frequently-occu...

Claims

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Application Information

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IPC IPC(8): C07H17/04C07H1/08A61P7/02
CPCC07H1/08C07H17/04
Inventor 罗跃华马双成付辉政付剑江陈伟康黄波王珊
Owner 江西省药品检验检测研究院
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