A fruit polyphenol compound, composition, preparation method thereof, and its application in the preparation of products with anti-inflammatory effects.

Abstract

This invention discloses a fruit polyphenol compound, a composition thereof, a method for preparing the same, and its application in the preparation of products with anti-inflammatory effects. The fruit polyphenol compound has a structure shown in Formula I, Formula II, or Formula III. Studies have shown that the fruit polyphenol compound and the composition thereof have good anti-inflammatory effects; moreover, their anti-inflammatory effects are significantly higher than those of the positive control drug resveratrol. Therefore, using the fruit polyphenol compound or composition of this invention as an active ingredient in the preparation of foods, dietary supplements, functional foods, skin care products, or pharmaceuticals with anti-inflammatory effects has significant application value.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of biological medicine, in particular to a fruit polyphenol compound, a composition, a preparation method thereof and application thereof in preparing products with anti-inflammatory effect. BACKGROUND

[0002] Pineapple is one of the famous tropical fruits, and Guangdong Province is the largest pineapple production province in China. The fruit is thick and sweet, and has the effects of relieving summer-heat, quenching thirst, digesting food and stopping diarrhea, and is one of the fruits that are deeply loved by the public. Existing studies have shown that pineapple contains a large amount of bromelain, which can effectively treat inflammation.

[0003] Because bromelain is easy to be inactivated, it is difficult to be utilized. In addition, there are few reports on anti-inflammatory effective components in pineapple in the prior art. Therefore, it has important application value to develop more effective components with anti-inflammatory effect from pineapple as raw material. SUMMARY

[0004] In order to overcome at least one of the technical problems in the prior art, the present application first provides a fruit polyphenol compound.

[0005] The technical scheme of the present application is as follows:

[0006] The present application first provides a fruit polyphenol compound, characterized in that it has the structure shown in formula I, formula II or formula III.

[0007]

[0008] The present application also provides a preparation method of the above-mentioned fruit polyphenol compound, wherein the fruit polyphenol compound is prepared from pineapple.

[0009] Preferably, the preparation method of the fruit polyphenol compound comprises the following steps:

[0010] (1) Fresh pineapple is cut into pieces, and then extracted with an organic solvent to obtain a pineapple organic solvent extract;

[0011] (2) The pineapple organic solvent extract is eluted on a macroporous resin column to obtain a pineapple macroporous resin elution fraction;

[0012] (3) The pineapple macroporous resin elution fraction is eluted on a silica gel column to obtain a silica gel elution fraction;

[0013] (4) The silica gel elution fraction is separated by preparative PHLC to obtain the fruit polyphenol compound.

[0014] Preferably, the organic solvent in step (1) is acetone.

[0015] Preferably, the specific elution method of the macroporous resin column in step (2) is as follows: the macroporous resin column is eluted with the pineapple organic solvent extract, first with 22-24% ethanol aqueous solution to remove impurities, and then with 38-40% ethanol aqueous solution, and the eluate eluted with 38-40% ethanol aqueous solution is collected, concentrated and dried to obtain the pineapple macroporous resin elution fraction.

[0016] Most preferably, the macroporous resin column is eluted with the pineapple organic solvent extract, first with 23% ethanol aqueous solution to remove impurities, and then with 39% ethanol aqueous solution, and the eluate eluted with 39% ethanol aqueous solution is collected, concentrated and dried to obtain the pineapple macroporous resin elution fraction.

[0017] Preferably, the specific elution method of the silica gel column in step (3) is as follows: the silica gel column is eluted with the pineapple macroporous resin elution fraction, first with a mixture of n-hexane and acetone in a volume ratio of 100:20 to remove impurities, and then with a mixture of n-hexane and acetone in a volume ratio of 100:25, and the eluate eluted with the mixture of n-hexane and acetone in a volume ratio of 100:25 is collected, concentrated and dried to obtain the pineapple silica gel elution fraction, and the pineapple silica gel elution fraction is taken to obtain the fruit extract.

[0018] Preferably, the preparation conditions of the fruit polyphenolic compounds of the structures shown in formula I and formula II are as follows: a C18 column is used as the chromatographic column, the detection wavelength is 280-330 nm, the flow rate is 5-15 mL / min, the column temperature is 20-30℃, and 13% acetonitrile aqueous solution is used as the eluent; the eluate corresponding to the chromatographic peak with a retention time of 9.27 min is collected, concentrated and dried to obtain the fruit polyphenolic compound of the structure shown in formula I, and the eluate corresponding to the chromatographic peak with a retention time of 12.35 min is collected, concentrated and dried to obtain the fruit polyphenolic compound of the structure shown in formula II.

[0019] The preparation conditions of the fruit polyphenolic compound of the structure shown in formula III are as follows: a C18 column is used as the chromatographic column, the detection wavelength is 280-330 nm, the flow rate is 5-15 mL / min, the column temperature is 20-30℃, and 16% acetonitrile aqueous solution is used as the eluent; the eluate corresponding to the chromatographic peak with a retention time of 15.18 min is collected, concentrated and dried to obtain the fruit polyphenolic compound of the structure shown in formula III.

[0020] The application also provides a composition comprising any two of the fruit polyphenolic compounds of the structures shown in formula I, formula II or formula III.

[0021] Preferably, the composition comprises the fruit polyphenols of the structures shown in formula II and formula III.

[0022] Further preferably, the weight ratio of the fruit polyphenols of the structures shown in formula II and formula III is 1-3:1-3.

[0023] Most preferably, the weight ratio of the fruit polyphenols of the structures shown in formula II and formula III is 1:1.

[0024] The present application also provides a use of the fruit polyphenols or the composition as described above in the preparation of a product with anti-inflammatory effect.

[0025] Preferably, the product is a food, a dietary supplement, a functional food, a skin care product or a medicine.

[0026] (1) The present application provides a brand new fruit polyphenol; studies have shown that the fruit polyphenol has good anti-inflammatory effect; and its anti-inflammatory effect is significantly higher than that of the positive control drug resveratrol.

[0027] (2) The present application also provides a brand new preparation method of the fruit polyphenols of formula I, formula II and formula III; the method first uses pineapple as a raw material to prepare the fruit polyphenols of the structures shown in formula I or formula II. In the preparation method of the fruit polyphenols of the present application, the elution conditions of macroporous resin, the elution conditions of silica gel column and the elution conditions of preparative HPLC are all very critical; if any one of the elution conditions is not properly selected, the fruit polyphenols of formula I, formula II and formula III cannot be prepared from pineapple. Using the method steps of the present application, only under the elution conditions of macroporous resin, the elution conditions of silica gel column and the elution conditions of preparative HPLC of the present application, the fruit polyphenols of formula I, formula II and formula III can be prepared.

[0028] (3) The present application provides a brand new composition comprising fruit polyphenols; studies have shown that the composition obtained by combining the fruit polyphenols of the structures shown in formula II and formula III has significantly higher anti-inflammatory effect than the fruit polyphenols of the structures shown in formula II or formula III alone.

[0029] (3) Since the fruit polyphenols of the structures shown in formula I, formula II and formula III or the composition thereof have anti-inflammatory effect; therefore, they are used as effective ingredients to prepare food, dietary supplement, functional food, skin care product or medicine with anti-inflammatory effect, which has important application value. BRIEF DESCRIPTION OF DRAWINGS

[0030] Figure 1HR-ESI-MS spectrum of the fruit polyphenolic compound of formula I.

[0031] Figure 2 HR-ESI-MS spectrum of the fruit polyphenolic compound of formula I. 1 H NMR spectrum.

[0032] Figure 3 HR-ESI-MS spectrum of the fruit polyphenolic compound of formula I. 13 C NMR spectrum.

[0033] Figure 4 DEPT-135 spectrum of the fruit polyphenolic compound of formula I.

[0034] Figure 5 HR-ESI-MS spectrum of the fruit polyphenolic compound of formula I. 1 H- 1 H COSY spectrum.

[0035] Figure 6 HMBC spectrum of the fruit polyphenolic compound of formula I Figure 1 .

[0036] Figure 7 HMBC spectrum of the fruit polyphenolic compound of formula I Figure 2 .

[0037] Figure 8 HR-ESI-MS spectrum of the fruit polyphenolic compound of formula II.

[0038] Figure 9 HR-ESI-MS spectrum of the fruit polyphenolic compound of formula II. 1 H NMR spectrum.

[0039] Figure 10 HR-ESI-MS spectrum of the fruit polyphenolic compound of formula II. 13 C NMR spectrum.

[0040] Figure 11 DEPT-135 spectrum of the fruit polyphenolic compound of formula II.

[0041] Figure 12 HR-ESI-MS spectrum of the fruit polyphenolic compound of formula II. 1 H- 1 H COSY spectrum.

[0042] Figure 13 HMBC spectrum of the fruit polyphenolic compound of formula II Figure 1 .

[0043] Figure 14HMBC spectrum of the fruit polyphenol compound shown as the structure of formula II Figure 2 .

[0044] Figure 15 HR-ESI-MS spectrum of the fruit polyphenol compound shown as the structure of formula III.

[0045] Figure 16 HMBC spectrum of the fruit polyphenol compound shown as the structure of formula III 1 H NMR spectrum.

[0046] Figure 17 HMBC spectrum of the fruit polyphenol compound shown as the structure of formula III 13 C NMR spectrum.

[0047] Figure 18 DEPT-135 spectrum of the fruit polyphenol compound shown as the structure of formula III.

[0048] Figure 19 HMBC spectrum of the fruit polyphenol compound shown as the structure of formula III Figure 1 .

[0049] Figure 20 HMBC spectrum of the fruit polyphenol compound shown as the structure of formula III Figure 2 . DETAILED DESCRIPTION

[0050] The technical solutions of the present application will be described clearly and completely below in conjunction with the embodiments. Obviously, the described embodiments are only some of the embodiments of the present application, but not all the embodiments. Based on the embodiments in the present application, all the other embodiments obtained by those skilled in the art without any creative work, fall within the protection scope of the present application.

[0051] Preparation of the fruit polyphenol compound

[0052] (1) Fresh pineapple is cut into pieces, and then heated to 55℃ by using an organic solvent to perform heating reflux extraction for 70 min to obtain an organic solvent extract; the organic solvent extract is concentrated and dried to obtain a pineapple organic solvent extract; wherein the ratio of the amount of fresh pineapple to the amount of organic solvent is 1:8; the organic solvent is acetone;

[0053] (2) The pineapple organic solvent extract is subjected to macroporous resin column (the macroporous resin column uses D101 macroporous resin as the filler; the weight amount of D101 macroporous resin is 40 times that of the pineapple organic solvent extract), first eluted with 5 times the column volume of 23% ethanol aqueous solution to remove impurities; then eluted with 5 times the column volume of 39% ethanol aqueous solution, and the eluate eluted by the 39% ethanol aqueous solution is collected, concentrated and dried to obtain a pineapple macroporous resin elution fraction;

[0054] (3) The pineapple macroporous resin elution fraction is subjected to silica gel column (the silica gel column uses 300-400 mesh silica gel as the filler; the weight amount of silica gel is 50 times that of the pineapple macroporous resin elution fraction), first eluted with 5 times the column volume of mixed solvent of n-hexane and acetone in a volume ratio of 100:20 to remove impurities; then eluted with 5 times the column volume of mixed solvent of n-hexane and acetone in a volume ratio of 100:25, and the eluate eluted by the mixed solvent of n-hexane and acetone in a volume ratio of 100:25 is collected, concentrated and dried to obtain a pineapple silica gel elution fraction;

[0055] (4) The pineapple silica gel elution fraction is subjected to preparation by preparative HPLC to obtain the fruit polyphenolic compound.

[0056] The preparation conditions of the fruit polyphenolic compound of formula I and formula II are as follows: a C18 column (9.4*250mm, 5μm, Agilent) is used as the chromatographic column, the detection wavelength is 300nm, the flow rate is 10mL / min, the column temperature is 25℃, and the eluent is 13% acetonitrile aqueous solution; the eluate corresponding to the chromatographic peak with a retention time of 9.27min is collected, concentrated and dried to obtain the fruit polyphenolic compound of formula I; and the eluate corresponding to the chromatographic peak with a retention time of 12.35min is collected, concentrated and dried to obtain the fruit polyphenolic compound of formula II.

[0057] The preparation conditions of the fruit polyphenolic compound of formula III are as follows: a C18 column is used as the chromatographic column, the detection wavelength is 300nm, the flow rate is 10mL / min, the column temperature is 25℃, and the eluent is 16% acetonitrile aqueous solution; the eluate corresponding to the chromatographic peak with a retention time of 15.18min is collected, concentrated and dried to obtain the fruit polyphenolic compound of formula III.

[0058] The fruit polyphenolic compound of formula I is a yellow oil, and HR-ESI-MS shows a quasi-molecular ion peak at m / z 335.1862 [M+H] + (C 19 H 27 O5, the theoretical calculation value is 335.1853), and the molecular formula is C19 H 26 O5, unsaturation 7. 1 HNMR (400 MHz, CDCl3) spectrum showed 26 proton signals. Among them, δ H 13.74 (1H, s), 8.64 (1H, s) were the signals of hydroxyl hydrogen on two benzene rings; δ H 5.22 (1H, t, J = 6.6 Hz), 3.34 (2H, d, J = 6.6 Hz), 1.79 (3H, s), 1.72 (3H, s) indicated that the molecule contained a 3-methyl-2-butene group. In the high field region, δ H 3.82 (2H, s) was a methylene hydrogen signal connected with oxygen; δ H 2.84 (1H, m) was a methine hydrogen signal connected with oxygen; δ H 3.73 (3H, s), 2.68 (3H, s), 1.17 (6H, d, J = 6.9 Hz) indicated that the compound also had four methyl proton signals, among which δ H 3.73, 2.68 were two oxygen-methyl signals. 13 CNMR (100 MHz, CDCl3) spectrum showed 19 carbon signals, and DEPT-135 spectrum showed that they were 9 quaternary carbons, 2 methine carbons, 2 methylene carbons and 6 methyl carbons. In the low field region, δ C 217.8, 203.8 were two ketone carbonyl signals; δ C 133.4, 122.8 were a pair of double bond signals; δ C 162.4, 161.5, 160.6, 114.8, 109.2, 105.5 were presumably the carbon signals of benzene ring. In 1 H- 1 In HCOSY spectrum, H-3″′ (δ H 2.84) was correlated with H-4″′ (δ H 1.17), H-5″′ (δ H 1.17), which could be inferred that the compound contained an isopropyl fragment. In HMBC spectrum, H-1″′ (δ H 3.82) and H-4″′ / 5″′ (δ H 1.17) were all correlated with C-2″′ (δ C 217.8), C-3″′ (δ C 41.7), which could confirm the presence of a 3-methyl-2-butanone fragment in the structure. At the same time, it could be observed that H-1″′ (δ H 3.82) was correlated with C-2′ (δ C 161.5), C-3′ (δ C105.3),C-4′(δ C The correlation with 162.4) confirms that the 3-methyl-2-butanone fragment is linked to the C-3′ position on the benzene ring. Based on the above data, the structure of the substituent group on the benzene ring is confirmed, and the structure of the compound is deduced. Combining 1D and 2D NMR spectral information, all fruit polyphenol compounds with the structure shown in Formula I were assigned (Table 1).

[0059] The fruit polyphenol compound with the structure shown in Formula II: a yellow oily substance, HR-ESI-MS shows a quasi-molecular ion peak at m / z 357.1673 [M+Na]. + (C 19 H 26 O5Na (theoretical calculated value: 357.1672), the molecular formula is determined to be C. 19 H 26 O5 has an unsaturation degree of 7. 1 The 1H NMR (300MHz, CDCl3) spectrum showed a total of 24 proton signals. H The values ​​of 5.21 (1H, tt, J = 6.0, 3.0 Hz), 3.33 (2H, d, J = 6.0 Hz), 1.78 (3H, s), and 1.70 (3H, s) suggest the presence of a 3-methyl-2-butenyl group in the molecule. Furthermore, this compound also exhibits two olefinic proton signals [δ]. H 5.01(1H,m), 4.87(1H,m)]; 1 methylene hydrogen signal [δ] H 4.33 (1H, d, J = 8.3 Hz)]; 3 methyl proton signals [δ H 3.72(3H,s),2.69(3H,s),1.85(3H,s)]. 13 The CNMR (75MHz, CDCl3) spectrum showed 19 carbon signals, which, combined with the DEPT-135 spectrum, identified as 9 quaternary carbons, 2 methines, 3 methylenes, and 5 methyl groups. δ-carbons were visible in the low-field region. C A single ketone carbonyl signal at 203.7; δ C 132.2, 123.3 and δ C 147.2 and 110.5 represent two pairs of double-bonded carbon signals; δ C 162.4, 162.1, 160.1, 115.0, 109.5, and 108.9 can be inferred to be carbon signals from the benzene ring. 1 H- 1 In the H COSY spectrum, H-2″′(δ) can be observed. H 4.33) and H-1″′(δ H There is a correlation between 3.15 and 2.75. Combined with HMBC spectral data, H-4″′ (δH 5.01) with C-2" (δ C 77.8), C-5" (δ C 18.6) can confirm the presence of a 3-methyl-2-hydroxy-3-butene fragment in the structure. In the HMBC spectrum, the correlation of H-1" (δ H 2.75, 3.15) with C-2' (δ C 162.1), C-3' (δ C 109.5), C-4' (δ C 162.4) can confirm the position of the substituent on the benzene ring is C-3'. Based on the above data, the structure of the substituent on the benzene ring was deduced. The structure of the fruit polyphenol compound shown in formula II was completely assigned by combining the 1D and 2D NMR spectral information (Table 2).

[0060] The fruit polyphenol compound shown in formula III: yellowish oil, HR-ESI-MS shows the quasi-molecular ion peak m / z 337.1988 [M+H] + (C 19 H 29 O5, the theoretical calculation value: 337.2010) to determine the molecular formula C 19 H 28 O5, the unsaturation degree is 6. 1 H NMR (400MHz, CDCI3) spectrum shows 26 proton signals. δ H 13.29 (1H, s) indicates that there is 1 hydroxyl hydrogen signal on the benzene ring; in addition, the compound has 1 olefinic proton signal δ H 5.22 (1H, m); 3 groups of methylene proton signals [δ H 3.27 (2H, d, J = 7.3 Hz), 2.70 (2H, d, J = 6.8 Hz), 1.79 (2H, overlapped)]; 6 methyl proton signals [δ H 3.74 (3H, s), 2.67 (3H, s), 1.78 (3H, s), 1.66 (3H, s), 1.35 (6H, s)], of which 2 are oxygen-containing methyl signals [δ H 3.74 (3H, s), 2.67 (3H, s)]. 13 C NMR (100MHz, CDCI3) spectrum shows 19 carbon signals, combined with DEPT-135 spectrum, which are 9 quaternary carbons, 1 methine, 3 methylene and 6 methyl groups. In the low field region, there is 1 ketone carbonyl signal δ C 203.4; δ C122.6, 131.2 for 1 pair of double bond carbon signals; δ C 160.9, 159.2, 159.0, 112.9, 108.6, 106.5 for carbon signals of benzene ring. In the HMBC spectrum, the correlation of H-2" (δ H 1.79) with C-l" (δ C 17.2), C-3" (δ C 75.6) was observed, and the correlation of H-4" / 5" (δ H 1.35) with C-2" (δ C 32.2), C-3" (δ C 75.6) was also observed. This structure contained a 3-methyl-3-hydroxybutyl fragment. In the HMBC spectrum, the correlation of H-l" (δ H 2.70) with C-5' (δ C 106.5), C-6' (δ C 159.2) was observed, which confirmed that this fragment was connected to C-5'. Based on the above data, the structure of the substituent on the benzene ring was confirmed, and the structure of the compound was deduced. The fruit polyphenol compounds of the structure shown in Formula III (Table 3) were identified based on the 1D and 2D NMR spectral information.

[0061] Table 1 1D and 2D NMR data of fruit polyphenol compounds of the structure shown in Formula I (CDC13, δ in ppm)

[0062]

[0063]

[0064] Table 2 1D and 2D NMR data of fruit polyphenol compounds of the structure shown in Formula II (CDC13, δ in ppm)

[0065]

[0066] Table 3 1D and 2D NMR data of fruit polyphenol compounds of the structure shown in Formula III (CDC13, δ in ppm)

[0067]

[0068]

[0069] Preparation of the composition of Example 2

[0070] The composition is obtained by mixing the fruit polyphenol compounds of the structures shown in Formula I and Formula II in a weight ratio of 1:1.

[0071] Preparation of the composition of Example 3

[0072] The fruit polyphenolic compounds of the structures shown in Formula I and Formula III are mixed at a weight ratio of 1:1 to obtain the composition.

[0073] Preparation of the composition of Example 4

[0074] The fruit polyphenolic compounds of the structures shown in Formula II and Formula III are mixed at a weight ratio of 1:1 to obtain the composition.

[0075] Example 1 Anti-inflammatory experiment of the fruit extract of the application

[0076] Healthy balb / c mice are raised at a temperature of 20-22℃, under natural light, with free access to food and water, and are fed with ordinary feed for 7 days. The mice are randomly divided into groups, with 10 mice in each group. Except for the blank control group, the rest of the groups are injected with 700 mg / (kg·d) of D-galactose to construct an oxidative damage model. Among them, the experimental groups are administered with the test sample at a dose of 10 mg / (kg·d), and the blank control group and the model group are injected with the same volume of normal saline and administered with the same volume of distilled water. The body weight is measured once every 2 days, and the experiment lasts for 28 days. After the experiment, blood is taken, and the content of the inflammatory factor TNF-α in the serum is determined according to the instructions of the ELISA kit. The content of TNF-α in the blank control group is taken as 100%, and the percentage of the content of TNF-α in the experimental groups and the model group relative to the blank control group is shown in Table 4.

[0077] Among them, experimental groups 1-3 test fruit polyphenolic compounds of the structures shown in Formula I, Formula II, or Formula III, respectively; experimental groups 4-6 test the compositions described in Examples 2-4, respectively; and experimental group 7 tests the positive control drug resveratrol.

[0078] Table 4. Anti-inflammatory experiment results of the fruit extract of the application

[0079]

[0080] As can be seen from the experimental results in Table 4, the percentage of the content of the inflammatory factor TNF-α of the fruit polyphenolic compounds of the structures shown in Formula I and II is significantly less than that of the model group; and the percentage of the content of the inflammatory factor TNF-α is also less than that of the positive control drug resveratrol; which indicates that the fruit polyphenolic compounds described in the application have good anti-inflammatory effects.

[0081] In particular, the fruit polyphenol compound of the structure of Formula III has a percentage of TNF-α content that is much less than that of the positive control drug resveratrol; the reduction degree of the fruit polyphenol compound of the structure of Formula III relative to resveratrol is significantly higher than that of the fruit polyphenol compounds of the structures of Formula I and II. This shows that the anti-inflammatory effects of the fruit polyphenol compounds of different structures in the present application are different; the anti-inflammatory effect of the fruit polyphenol compound of the structure of Formula III is significantly better than that of the fruit polyphenol compounds of the structures of Formula I and II.

[0082] As can be seen from the experimental results in Table 4, the composition described in Example 4 has a percentage of TNF-α content that is much less than that of the fruit polyphenol compounds of the structures of Formula I, II and III; this shows that the composition obtained by combining the fruit polyphenol compounds of the structures of Formula II and III has a more excellent anti-inflammatory effect, and the anti-inflammatory effect is much greater than that of the fruit polyphenol compounds of the structures of Formula I, II or III alone. As can be seen from the experimental results in Table 4, the composition described in Example 4 has a percentage of TNF-α content that is much less than that of the compositions described in Examples 2 and 3; the percentage of TNF-α content of the compositions described in Examples 2 and 3 is not reduced or greatly reduced compared with the fruit polyphenol compounds of the structures of Formula I, II or III; this shows that the composition obtained by combining the fruit polyphenol compounds of the structures of Formula I and II, or the composition obtained by combining the fruit polyphenol compounds of the structures of Formula I and III, cannot be improved or greatly improved in anti-inflammatory effect compared with the fruit polyphenol compounds of the structures of Formula I, II or III alone; only the composition obtained by combining the fruit polyphenol compounds of the structures of Formula II and III can be further greatly improved in anti-inflammatory effect compared with the fruit polyphenol compounds of the structures of Formula I, II or III alone.

Claims

1. A method for preparing fruit polyphenols, characterized by, The fruit polyphenols are prepared from pineapples. The fruit polyphenols have the structure shown in Formula I, Formula II or Formula III. The preparation method of the fruit polyphenols comprises the following steps: (1) fresh pineapples are cut into pieces and then extracted with an organic solvent to obtain a pineapple organic solvent extract; (2) the pineapple organic solvent extract is eluted on a macroporous resin column to obtain a pineapple macroporous resin elution fraction; (3) the pineapple macroporous resin elution fraction is eluted on a silica gel column to obtain a silica gel elution fraction; (4) the silica gel elution fraction is separated by preparative PHLC to obtain the fruit polyphenols; The organic solvent in step (1) is acetone. In step (2), the specific elution method of the macroporous resin column is as follows: the pineapple organic solvent extract is eluted on a macroporous resin column, first with an ethanol aqueous solution with a volume fraction of 22-24% to remove impurities, and then with an ethanol aqueous solution with a volume fraction of 38-40%, and the eluate eluted by the ethanol aqueous solution with a volume fraction of 38-40% is collected, concentrated and dried to obtain the pineapple macroporous resin elution fraction. The preparation conditions of the fruit polyphenols with the structure shown in Formula I and Formula II are as follows: a C18 column is used as the chromatographic column, the detection wavelength is 280-330 nm, the flow rate is 5-15 mL / min, the column temperature is 20-30 °C, an acetonitrile aqueous solution with a volume fraction of 13% is used as the eluent, the eluate corresponding to the chromatographic peak with a retention time of 9.27 min is collected, and the fruit polyphenols with the structure shown in Formula I are obtained by concentration and drying; the eluate corresponding to the chromatographic peak with a retention time of 12.35 min is collected, and the fruit polyphenols with the structure shown in Formula II are obtained by concentration and drying.

2. The production method according to claim 1, characterized by, The specific elution method of the silica gel column in step (3) is as follows: the pineapple macroporous resin elution fraction is eluted on a silica gel column, first with a mixed solvent of n-hexane and acetone with a volume ratio of 100:20 to remove impurities, and then with a mixed solvent of n-hexane and acetone with a volume ratio of 100:25, and the pineapple silica gel elution fraction is obtained by concentration and drying of the eluate eluted by the mixed solvent of n-hexane and acetone with a volume ratio of 100:

25.

3. The preparation method according to claim 1, characterized in that, The preparation conditions of the fruit polyphenols with the structure shown in Formula III are as follows: a C18 column is used as the chromatographic column, the detection wavelength is 280-330 nm, the flow rate is 5-15 mL / min, the column temperature is 20-30 °C, an acetonitrile aqueous solution with a volume fraction of 16% is used as the eluent, the eluate corresponding to the chromatographic peak with a retention time of 15.18 min is collected, and the fruit polyphenols with the structure shown in Formula III are obtained by concentration and drying.

Images