CN107056857B - Flavonoid compound and preparation method and application thereof - Google Patents

Abstract

The invention relates to a novel flavonoid compound which is selected from one or more of structures I-V. The compound can be extracted from the root of Hemsleya amabilis by a simple and easy operation method. The compound provided by the invention can effectively prevent coagulation and vascular smooth muscle cell proliferation or protect cells, and can be used for preparing medicines and health-care products; wherein, the compounds I and II are natural red pigments, can be added into foods, medicines, health products and cosmetics, and have potential application value.

Description

Flavonoid compound and preparation method and application thereof

Technical Field

The invention relates to the field of natural product chemistry, and particularly relates to a flavonoid compound and a preparation method and application thereof.

Background

Rhizoma Polygoni Cuspidati is derived from rhizome of Cauliflower anoplophora (Abacopteris penangiana (Hook.) Ching.) of Cauliflower of Chrysocopteraceae, and is also called JIXUELIAN, and XUELIAN, etc.; is a folk common traditional Chinese medicine of northern Hunan China; has effects in promoting blood circulation, regulating menstruation, dispelling blood stasis, relieving pain, and eliminating dampness; it can be used for treating menoxenia, metrorrhagia, traumatic injury, rheumatalgia, and edema.

At present, no report exists on extracting a novel compound with the functions of anticoagulation, anti-vascular smooth muscle cell proliferation or cell protection from the root of Heptachia henryi.

Disclosure of Invention

The invention aims to overcome the defects of the prior art, and the flavonoid compound is extracted from the root of Hemsleya amabilis, can effectively prevent blood coagulation and vascular smooth muscle cell proliferation or protect cells, and has potential application value.

Specifically, the compounds of the present invention are selected from one or more of structures I-V:

the invention further provides a preparation method of the compound, which comprises the following steps:

(1) extracting rhizoma Polygoni Cuspidati with ethanol, extracting the extractive solution with ethyl acetate, collecting ethyl acetate layer, and concentrating to obtain extract;

(2) loading the extract to a silica gel column, and eluting with ethyl acetate-methanol as a mobile phase to obtain an extract;

(3) separating and purifying the extract to obtain the extract.

Specifically, the compound I can be prepared by the following method:

(1) extracting rhizoma Polygoni Cuspidati with ethanol, extracting the extractive solution with ethyl acetate, collecting ethyl acetate layer, and concentrating to obtain extract;

(2) and (3) loading the extract into a silica gel column, and mixing the extract with a mixture of silica gel and silica gel in a volume ratio of 10-1: eluting with ethyl acetate-methanol solution of 1 to obtain extract;

(3) and (3) mixing the extract by using a solvent with the volume ratio of 5-3: 1, eluting with dichloromethane-methanol, and subjecting the obtained product to a reaction with a volume ratio of 1: 5-1: eluting with petroleum ether-dichloromethane-methanol of 1, loading the obtained product on Sephadex LH-20 column, and eluting with chloroform-methanol of 1:1 volume ratio to obtain compound I;

or:

(1) extracting rhizoma Polygoni Cuspidati with ethanol, extracting the extractive solution with ethyl acetate, collecting ethyl acetate layer, and concentrating to obtain extract;

(2) and (3) loading the extract into a silica gel column, and mixing the extract with a mixture of silica gel and silica gel in a volume ratio of 10-1: eluting with ethyl acetate-methanol solution of 1 to obtain extract;

(3) and (2) mixing the extract by using a solvent with a volume ratio of 8-2: 1, eluting the obtained product by using dichloromethane-methanol, wherein the volume ratio of the obtained product is 5-1: 1, eluting the obtained product with chloroform-methanol, and performing elution by using a solvent with a volume ratio of 8-5: 1, and eluting the obtained product by using semi-preparative HPLC (high performance liquid chromatography) with 55% acetonitrile-water as a mobile phase to obtain the compound I.

Specifically, the compound II can be prepared by the following method:

(1) extracting rhizoma Polygoni Cuspidati with ethanol, extracting the extractive solution with ethyl acetate, collecting ethyl acetate layer, and concentrating to obtain extract;

(2) and (3) loading the extract into a silica gel column, and mixing the extract with a mixture of silica gel and silica gel in a volume ratio of 10-1: eluting with ethyl acetate-methanol solution of 1 to obtain extract;

(3) and (3) mixing the extract by using a solvent with the volume ratio of 5-3: 1, eluting the obtained product by using dichloromethane-methanol, wherein the volume ratio of the obtained product is 3-0: eluting with dichloromethane-methanol of 1, loading the obtained product on Sephadex LH-20 column, and eluting with chloroform-methanol of 1:1 volume ratio to obtain compound II.

Specifically, the compound III can be prepared by the following method:

(1) extracting rhizoma Polygoni Cuspidati with ethanol, extracting the extractive solution with ethyl acetate, collecting ethyl acetate layer, and concentrating to obtain extract;

(2) and (3) loading the extract into a silica gel column, and mixing the extract with a mixture of silica gel and silica gel in a volume ratio of 100-20: eluting with ethyl acetate-methanol solution of 1 to obtain extract;

(3) and (2) mixing the extract with a solvent with a volume ratio of 8-3: 1, eluting the obtained product by using chloroform-methanol, wherein the volume ratio of the obtained product is 1-0: eluting with chloroform-methanol of 1, loading the obtained product on Sephadex LH-20 column, and eluting with chloroform-methanol of 1:1 volume ratio to obtain compound III.

Specifically, the compound IV can be prepared by the following method:

(1) extracting rhizoma Polygoni Cuspidati with ethanol, extracting the extractive solution with ethyl acetate, collecting ethyl acetate layer, and concentrating to obtain extract;

(2) and (3) loading the extract into a silica gel column, and mixing the extract with a mixture of silica gel and silica gel in a volume ratio of 100-20: eluting with ethyl acetate-methanol solution of 1 to obtain extract;

(3) the extract is prepared by mixing the following components in a volume ratio of 10-5: 1, eluting the obtained product by using chloroform-methanol, wherein the volume ratio of the obtained product is 10-8: 1, eluting the obtained product by using chloroform-methanol, wherein the volume ratio of the obtained product is 20-10: eluting with dichloromethane-methanol to obtain compound IV;

or the following steps:

(1) extracting rhizoma Polygoni Cuspidati with ethanol, extracting the extractive solution with ethyl acetate, collecting ethyl acetate layer, and concentrating to obtain extract;

(2) and (3) loading the extract into a silica gel column, and mixing the extract with a mixture of silica gel and silica gel in a volume ratio of 100-20: eluting with ethyl acetate-methanol solution of 1 to obtain extract;

(3) and (3) mixing the extract by using a solvent with a volume ratio of 3-0: 1, eluting the obtained product by using chloroform-methanol, wherein the volume ratio of the obtained product is 3-0: 1, eluting the obtained product by using chloroform-methanol, wherein the volume ratio of the obtained product is 5-3: 1, and eluting the obtained product with chloroform-methanol, wherein the volume ratio of the obtained product is 5: eluting with chloroform-methanol to obtain compound IV.

Specifically, the compound V can be prepared by the following method:

(1) extracting rhizoma Polygoni Cuspidati with ethanol, extracting the extractive solution with ethyl acetate, collecting ethyl acetate layer, and concentrating to obtain extract;

(2) and (3) loading the extract into a silica gel column, and mixing the extract with a mixture of silica gel and silica gel in a volume ratio of 100-20: eluting with ethyl acetate-methanol solution of 1 to obtain extract;

(3) and (2) mixing the extract with a solvent with the volume ratio of 20-10: 1, eluting the obtained product by using chloroform-methanol, wherein the volume ratio of the obtained product is 20-10: 1, eluting the obtained product by using chloroform-methanol, wherein the volume ratio of the obtained product is 20-10: eluting with chloroform-methanol to obtain compound V;

or the following steps:

(1) extracting rhizoma Polygoni Cuspidati with ethanol, extracting the extractive solution with ethyl acetate, collecting ethyl acetate layer, and concentrating to obtain extract;

(2) and (3) loading the extract into a silica gel column, and mixing the extract with a mixture of silica gel and silica gel in a volume ratio of 100-20: eluting with ethyl acetate-methanol solution of 1 to obtain extract;

(3) and (3) mixing the extract by using a solvent with a volume ratio of 3-0: 1, eluting the obtained product by using chloroform-methanol, wherein the volume ratio of the obtained product is 3-0: 1, eluting the obtained product with chloroform-methanol, wherein the volume ratio of the obtained product is 3-1: 1, eluting with chloroform-methanol, and then performing elution on the obtained product by using a solvent with the volume ratio of 5-1: eluting with chloroform-methanol to obtain compound V.

Unless otherwise specified, the stationary phase used in the elution of the present invention is a silica gel column.

The invention further protects the application of the compound in preparing anticoagulant, anti-vascular smooth muscle cell proliferation and/or cell protection medicines; the cytoprotection is preferably inhibition of hydrogen peroxide induced cell damage.

The novel compound is extracted from the root of Hemsleya amabilis by a simple method. The compound can effectively prevent blood coagulation and vascular smooth muscle cell proliferation or protect cells, and has potential application value.

Drawings

FIGS. 1 to 8 show the UV spectrum, IR spectrum, MS spectrum and mass spectrum of Compound 1, respectively,¹³C-NMR spectrum,¹H-NMR spectrum, HSQC spectrum, HMBC spectrum and¹H-¹h COSY spectrum;

FIGS. 9 to 16 show the UV spectrum, IR spectrum, MS spectrum and B spectrum of Compound 2, respectively,¹³C-NMR spectrum,¹H-NMR spectrum, HSQC spectrum, HMBC spectrum and¹H-¹h COSY spectrum;

FIGS. 17 to 24 show the UV spectrum, IR spectrum, MS spectrum and B spectrum of Compound 3, respectively,¹³C-NMR spectrum,¹H-NMR spectrum, HSQC spectrum, HMBC spectrum and¹H-¹h COSY spectrum;

FIGS. 25 to 32 show the UV spectrum, IR spectrum, MS spectrum and B spectrum of Compound 4, respectively,¹³C-NMR spectrum,¹H-NMR spectrum, HSQC spectrum, HMBC spectrum and¹H-¹h COSY spectrum;

FIGS. 33 to 40 show the UV spectrum, IR spectrum, MS spectrum and B spectrum of Compound 5, respectively,¹³C-NMR spectrum,¹H-NMR spectrum, HSQC spectrum, HMBC spectrum and¹H-¹h COSY spectrum;

figure 41 is a graph showing the effect of compound 3 on angiotensin II-induced vascular smooth muscle cell proliferation; wherein, P<0.05 compared with the normal group,^#P<0.05,^##P<0.01 compared to model set;

FIG. 42 is a schematic representation of the protective effect of Compound 3 on hydrogen peroxide-induced PC12 cells; p<0.05，^#P<0.05，^##P<0.01 was compared to the model group.

Detailed Description

The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.

Example 1

The embodiment provides a flavonoid compound, which has the following specific structure:

the characterization patterns of the compound are shown in figures 1-8; the specific information is as follows:

a red-colored powder,

HRESI-MS gave [ M + H]⁺m/z 459.1661(Calcd for C₂₄H₂₇O₉459.1655), it can be determined that the compound has the formula C₂₄H₂₆O₉The unsaturation degree is 12;

the UV spectrum shows absorption maxima at 347nm and 524 nm;

the IR spectrum shows that: hydroxyl (3413 cm)^-1) Carbonyl group (1601 cm)^-1) And a benzene ring (1641, 1498 cm)^-1)；

¹³The C-NMR spectrum showed 24 carbon signals: i.e. signals for a group of flavonoid structures, one glucose, one methoxy group and two methyl groups; from¹In the H-NMR spectrum, six aromatic hydrogens: delta_H8.64(1H, dd, 7.6Hz), 7.89(2H, dd, 8.9Hz), 7.10(2H, dd, 8.9Hz), 6.81(1H, dd, 7.6 Hz); terminal proton of one saccharide: delta_H5.42(d, 7.6Hz), one methoxy group: delta_H3.75(3H, s), two methyl groups: delta_H2.78(3H, s), 2.38(3H, s), see table 1;

in that¹H-¹On the H COSY spectrum, H-3 is related to H-4, H-2'(6') is related to H-3'(5'), and the correlation of one-dimensional hydrogen spectrum coupling signals is confirmed;

in HMBC spectra, 4' -OCH₃(δ_H3.75, s) and C-4' (delta)_C162.3) related, indicating that the methoxy group is attached at the C-4' position;h-2 'or 6' (delta)_H7.89, dd, 8.9Hz) and C-2 (. delta.) (_C158.2), C-3 'or C-5' (delta)_C114.8)，C-4′(δ_C162.3) correlation; h-3 'or 5' (delta)_H7.10, dd, 8.9Hz) and C-1' (delta)_C124.1)，C-4′(δ_C162.3) correlation; indicating that the B ring is a 4' -methoxy substituted benzene ring attached to the C-2 position. H-1' (delta)_H5.42, d, 7.6Hz) and C-5 (. delta.) (_C151.4), indicating that the sugar is attached at the C-5 position; 6-CH3 (delta)_H2.78, s) and C-5 (. delta.))_C151.4)、C-6(δ_C128.3)、C-7(δ_C183.2) correlation; 8-CH3 (delta)_H2.38, s) and C-7 (. delta.))_C183.2)、C-8(δ_C109.2)、C-9(δ_C153.9), related, indicating that ring a is methyl substituted at positions 6,8 and carbonyl at position 7. H-3 (delta)_H6.82, d, 7.6Hz) and C-2 (. delta.) (_C158.2)、C-10(δ_C118.4)、C-1′(δ_C124.1) correlation, H-4 (. delta.))_H8.65, d, 7.6Hz) and C-2 (. delta.) (_C158.2)、C-5(δ_C151.4)、C-9(δ_C153.9), indicating no substitution at positions 3 and 4 on the C ring.

In summary, the compound was identified as 6,8-dimethyl-2- (4 '-methoxy-phenyl) -7H-1-benzopyran-7-one-5-O- β -D-glucopyranoside, i.e., 6,8-dimethyl-2- (4' -methoxyphenyl) -7H-1-benzopyran-7-one-5-O- β -D-glucose.

Example 2

The embodiment provides a flavonoid compound, which has the following specific structure:

the characterization patterns of the compound are shown in figures 9-16; the specific information is as follows:

a red-colored powder,

HRESIMS gives [ M + H [ ]]⁺m/z 501.1817(Calcdfor C₂₆H₂₉O₁₀501.1761), the formula C can be identified₂₆H₂₈O₁₀Is not limited toThe saturation was 13. The UV spectrum shows a maximum absorption at 512 nm. The IR spectrum shows that: hydroxyl (3364 cm)^-1) Carbonyl group (1729 cm)^-1) And a benzene ring (1647, 1601, 1499 cm)^-1)。

In comparison with the compound 1, the compound of formula (I),¹³one more delta in the C-NMR spectrum_C170.4 (carbonyl) and delta_C20.4 (methyl). In HMBC spectra, H-6' (delta)_H4.26, dd) and carbonyl (. delta.) groups_C170.4), indicating that the carbonyl group is attached at the C-6 "position; 6' -CH₃(δ_H1.89, s) and carbonyl (. delta.) groups_C171.2) indicates that the methyl group is attached to the carbonyl position.

In summary, the compound was identified as 6,8-dimethyl-2- (4 '-methoxy-phenyl) -7H-1-benzopyran-7-one-5-O- β -D-6' -acetyl-glucopyranoside, i.e., 6,8-dimethyl-2- (4 '-methoxyphenyl) -7H-1-benzopyran-7-one-5-O- β -D-6' -acetyl glucose.

Example 3

The embodiment provides a flavonoid compound, which has the following specific structure:

the characterization patterns of the compound are shown in figures 17-24; the specific information is as follows:

a white powder of a white color, a white powder,HRESIMS gives [ M + H [ ]]⁺m/z 479.1916(Calcdfor C₂₄H₃₁O₁₀479.1917), the formula C can be identified₂₄H₃₀O₁₀The unsaturation degree was 10. The UV spectrum shows a maximum absorption at 273 nm. The IR spectrum shows that: hydroxyl (3400 cm)^-1) And benzene rings (1604, 1569, 1460 cm)^-1)。

¹³The C-NMR spectrum shows 24 carbon signals, i.e. signals for a group of flavonoid structures, one glucose and one methoxy group. From¹According to the H-NMR spectrum, the aromatic ring hydrogen signal: delta_H8.06(d, 8.9Hz, H-2 'and H-6'), 6.96(d, 8.9Hz, H-3 'and H-5'), constituting a set of AX systems. Delta_H3.34(dd，H-α)，δ_H3.20(m，H-α)，δ_H3.06(2H, dd, H- β), making up two groups-CH₂-a fragment. One sugar end hydrogen signal: delta_H4.66(d, 7.6Hz, H-1'). One methoxy signal: delta_H3.85(s,4′-OCH₃). Two methyl signals: delta_H2.08(s,5-CH₃) And delta_H2.18(s,3-CH₃). In that¹H-¹In the H COSY spectrum, H- α and H- β are related, H-2' (delta)_H8.06) and H-3' (delta)_H6.96) and confirms the correlation of the coupling signals of the one-dimensional hydrogen spectrum.

Sugar end group hydrogen H-1' (delta. in HMBC spectra_H4.66) and C-2 (. delta.))_C151.0) associated, indicating that the sugar is attached at the C-2 position; delta_H2.18(s，3-CH₃) With respect to C-3, C-2, etc., it is indicated that the methyl group is attached at the 3-position; delta_H2.08(s，5-CH₃) Relating to C-5, C-6, etc., it is indicated that the methyl group is attached at the 5-position H- α (dd, δ_H3.34；m，δ_H3.20) associated with the carbonyl carbon, β -C, C-1, H- β (dd, delta)_H3.06) in relation to the carbonyl carbons, α -C, C-1, C-2, the above information indicates the position of the hydrogen on the chalcone nucleus.

The compound is identified as α -dihydroxy-2, 4,6-trihydroxy-4 '-methoxy-3, 5-dimethyl-dihydroxy-ketone-2-O- β -D-glucopyranoside, namely 2,4, 6-trihydroxy-4' -methoxy-3,5-dimethyl dihydrochalcone by combining the above analyses.

Example 4

The embodiment provides a flavonoid compound, which has the following specific structure:

the characterization patterns of the compounds are shown in FIGS. 25-32; the specific information is as follows:

a yellow powder, and a white pigment,

HRESIMS gave [ M-Na + H ]₂O]⁺m/z 485.1043(Calcd for C₂₂H₂₂O₁₁Na, 485.1060), the molecular formula can be determined as C₂₂H₂₄O₁₂The unsaturation degree was 11. The UV spectrum shows absorption maxima at 336nm, 414 nm. The IR spectrum shows that: hydroxyl (3354 cm)^-1) And benzene rings (1600, 1505, 1453 cm)^-1)。

¹³The C-NMR spectrum shows 22 carbon signals, i.e. signals for a group of flavonoid structures, one glucose and one methoxy group.¹H-NMR spectrum showed aromatic hydrogen signal delta_H8.38(d, 2.8Hz, H-6), 7.21(d, 8.7, 2.8Hz, H-4), 7.18(d, 8.7Hz, H ═ 3), making up a set of ABX systems. Another aromatic ring hydrogen signal delta_H6.85(d, 1.7Hz, H-3 '), 6.17(d, 1.7Hz, H-5'), making up a set of AB systems. Sugar end group hydrogen signal delta_H5.85(d, 7.5Hz, H-1'). A methoxy signal delta_H3.74(s，4′-OCH₃). In that¹H-¹In the H COSY spectrum, H-6 and H-4 are related, and H-5 'and H-3' are related, so that the correlation of coupling signals of the one-dimensional hydrogen spectrum is confirmed.

Sugar end group hydrogen H-1' (delta. in HMBC spectra_H5.85) and C-2' (delta)_C157.5) related, indicating that the sugar is attached at the C-2' position; h-3' (delta)_H5.85) related to C-1 ', C-4', C-5 ', etc., H-5' (delta)_H5.85) related to C-1 ', C-3 ', C-6 ', etc.; h-3 (delta)_H7.18) relating to C-1, H-4 (. delta.))_H7.21) related to C-5, H-6 (. delta.))_H8.38) is related to β -C, C-3, C-4, H- β (delta)_H8.07) related to carbonyl, α -C, C-2, C-6 the above information illustrates the position of the hydrogen on the chalcone nucleus.

Based on the above analysis, the compound was identified as α,2,5, 2', 6' -pentahydroxy-4 '-methoxy-chalcon-2' -O- β -D-glucopyranoside, i.e., α,2,5, 2', 6' -pentahydroxy-4 '-methoxy-chalcone-2' -O- β -D-glucose.

Example 5

The embodiment provides a flavonoid compound, which has the following specific structure:

the characterization patterns of the compound are shown in figures 33-40; the specific information is as follows:

a yellow powder, and a white pigment,

HRESIMS gives [ M + H [ ]]m/z 465.1399(Calcdfor C₂₂H₂₅O₁₁465.1397), the formula C can be identified₂₂H₂₄O₁₁The unsaturation degree was 11. The UV spectrum shows a maximum absorption at 281 nm. The IR spectrum shows that: hydroxy (3333 cm)^-1) And a benzene ring (1649, 1607, 1505 cm)^-1)。

¹³The C-NMR spectrum showed 22 carbon signals, i.e.signals for the flavonoid structure, one glucose and one methoxy group.¹H-NMR spectrum showed aromatic hydrogen signal delta_H7.65(d, 2.4Hz, H-6'), 7.12(d, 8.7, 2.4Hz, H-4'), 7.11(d, 8.7Hz, H ═ 3'), make up a set of ABX systems. Another aromatic ring hydrogen signal delta_H7.06(d, 2.4Hz, H-6), 6.39(d, 2.4Hz, H-8), making up a set of AB systems. Sugar end group hydrogen signal delta_H5.38(d, J ═ 7.4Hz, H-1 "). A methoxy signal delta_H3.68(s，7-OCH₃). In the COSY spectrum, H-6 (. delta.)_H7.06) and H-8 (. delta.))_H6.39), H-6' (delta)_H7.65) and H-4' (delta)_H7.12) and confirms the correlation of the coupling signals of the one-dimensional hydrogen spectrum. In addition, H-2 (. delta.)_H6.21) and H-3 (. delta.))_H3.22) of the same.

Sugar end group hydrogen H-1' (delta. in HMBC spectra_H5.38) and C-5 (. delta.))_C161.3) related, indicating that the sugar is attached at the C-5 position; h-6 (delta)_H7.06) related to C-5, C-7, C-8, C-10, etc., H-8 (. delta.),_H6.39) related to C-6, C-9, C-10, etc.; h-6' (delta)_H7.65) with C-2, C-2 ', C-4 ', C-5 ', H-3' with C-1 ', C-2 ', C-5 '; h-2 (delta)_H6.21) related to C-6', H-3 (. delta.)_H3.22) related to C-2 and C-4; the above information illustrates the location of the hydrogen on the flavanone parent nucleus.

In combination with the above analyses, the compound was identified as 5, 2', 5' -trihydroxy-7-methoxy-flavanones-5-O- β -D-glucopyranoside, i.e., 5, 2', 5' -trihydroxy-7-methoxy-flavanone-5-O- β -D-glucose.

Experimental example 1: in vitro anticoagulation experiment

The invention researches the in-vitro anticoagulant activity of the compounds 1-5. The research result shows that: the compounds 1-5 can prolong the PT and TT time, and have no obvious influence on the APTT; in the range of 0.1g/ml to 0.5g/ml of sample concentration, a certain metering dependence relationship exists; and the anticoagulation effect is most obvious under the condition that the sample concentration is 0.5 g/ml.

Experimental example 2: MTT assay for detecting effects of compounds on angiotensin II-induced vascular smooth muscle cell proliferation

Cell lines: vascular Smooth Muscle Cells (VSMCs)

The experimental results are as follows: MTT experiments were performed on compound 3, and the results show that compound 3 has good activity of inhibiting proliferation of vascular smooth muscle cells at concentrations of 10. mu. mol/l and 30. mu. mol/l, and the results are shown in FIG. 41.

Experimental example 3: MTT assay for the protection of PC12 cells induced by Hydrogen peroxide

Cell lines: PC12 cell

The experimental results are as follows: MTT experiments are carried out on the compound 3, and the result shows that the compound 3 has better protection effect on PC12 cells induced by hydrogen peroxide, and the result is shown in figure 42.

From the above results, it was found that compound 3 has an anti-vascular smooth muscle cell proliferation activity and a protective effect against hydrogen peroxide-damaged PC12 cells.

The activity of the compounds 1, 2,4 and 5 is simultaneously tested, and the compounds have similar activity to the compound 3.

Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (4)

1. A flavonoid compound with anticoagulation, anti-vascular smooth muscle cell proliferation or cell protection functions is characterized by having a structure shown in a formula II:

2. a process for the preparation of a compound according to claim 1, characterized in that it is in particular:

(1) extracting rhizoma Polygoni Cuspidati with ethanol, extracting the extractive solution with ethyl acetate, collecting ethyl acetate layer, and concentrating to obtain extract;

(2) and (3) loading the extract into a silica gel column, and mixing the extract with a mixture of silica gel and silica gel in a volume ratio of 10-1: eluting with ethyl acetate-methanol solution of 1 to obtain extract;

(3) and (3) mixing the extract by using a solvent with the volume ratio of 5-3: 1, eluting the obtained product by using dichloromethane-methanol, wherein the volume ratio of the obtained product is 3-0: eluting with dichloromethane-methanol of 1, loading the obtained product on Sephadex LH-20 column, and eluting with chloroform-methanol of 1:1 volume ratio to obtain compound II.

3. Use of a compound according to claim 1 for the preparation of an anticoagulant, antiangiogenic, smooth muscle cell proliferation and/or cytoprotective agent.

4. The use of claim 3, wherein the cytoprotection is inhibition of hydrogen peroxide induced cell damage.

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