Preparation method for promoting cis-isomerization of lycopene

Abstract

The invention discloses a preparation method for promoting cis-isomerization of lycopene, which comprises the following steps: catalyzing the lycopene by using a bimetallic organic framework material as a catalyst to realize cis-isomerization, catalyzing the lycopene by using the catalyst to realize cis-isomerization of the lycopene, and catalyzing the lycopene by using the catalyst in an electron-rich environment to realize cis-isomerization of the lycopene. Conjugated double bonds of all-trans-lycopene are more easily attacked and activated, so that the conjugated double bonds are rotated into corresponding configurations, and the method is green and efficient and has great application prospects.

Description

Technical Field

[0001] The invention relates to a method for isomerizing lycopene, in particular to a preparation method for promoting cis-isomerization of lycopene. Background Art

[0002] More than 90% of lycopene in natural plants is in the all-trans configuration, and its bioavailability, antioxidant activity and other physiological activities are lower than those of the cis configuration. Therefore, seeking an effective method to promote the conversion of all-trans lycopene to cis isomers has become a research focus in the field of efficient utilization of lycopene. The cis isomer of lycopene has a higher bioavailability in the human body, which means that the cis isomer is more easily absorbed by the human body, thereby more effectively exerting its physiological function. At the same time, the cis lycopene isomer has a stronger antioxidant activity than the all-trans isomer. Antioxidants can neutralize free radicals and protect cells from oxidative stress, which plays an important role in preventing cardiovascular diseases, cancer, etc. Because cis isomers, especially 5-cis isomers, have higher biological activity and stability, they have broad development and application prospects in the fields of food, nutrition and medicine. These characteristics make lycopene products with a high proportion of cis isomers have higher added value in the market.

[0003] Common methods for cis-isomerization of lycopene include thermal isomerization, photoisomerization, catalytic isomerization, microwave isomerization, electrochemical isomerization, etc. Thermal isomerization is the most commonly used isomerization method in current research, which is to promote the conversion of lycopene from the all-trans isomer to the cis isomer by direct heating. During the heat treatment process, the increase in temperature and the extension of the processing time will increase the proportion of the cis isomer, but will cause a large amount of degradation of lycopene. Photoisomerization is to effectively promote the conversion of lycopene from the all-trans to the cis isomer under light conditions, especially when using a photosensitizer. However, the residual problem of the photosensitizer makes it unsuitable for industrial production. Catalytic isomerization usually uses metal ion catalysts, etc., which can significantly increase the content of cis isomers (especially 5-cis lycopene), but some metal catalyst residues are difficult to remove. Therefore, a safer and more efficient method for isomerization of lycopene is urgently needed. Summary of the invention

[0004] Purpose of the invention: The purpose of the present invention is to provide an efficient and safe preparation method for promoting the cis-isomerization of lycopene.

[0005] Technical solution: The present invention discloses a preparation method for promoting the cis-isomerization of lycopene. The preparation method uses a metal organic framework material UIO-66 or a bimetallic organic framework material as a catalyst to catalyze the cis-isomerization of lycopene.

[0006] The bimetallic organic framework material has an octahedral crystal structure and is formed by the coordination of an organic ligand tetrafluoroterephthalic acid and a metal ion, wherein the metal ion is a zirconium ion, a copper ion, a zinc ion or an iron ion.

[0007] Among the metal ions, the molar amount of the doped metal ions (copper ions, zinc ions or iron ions) is 20 to 50% of the total molar amount of the metal ions.

[0008] Wherein, the bimetallic organic framework material is Zn 1 / 5 -UIO-66, Zn 1 / 4 -UIO-66, Zn 1 / 2 -UIO-66, Cu 1 / 5 -UIO-66, Cu 1 / 4 -UIO-66, Cu 1 / 2 -UIO-66, Fe 1 / 5 -UIO-66, Fe 1 / 4 -UIO-66 or Fe 1 / 2 -UIO-66.

[0009] The method for preparing the bimetallic organic framework material comprises the following steps:

[0010] (1) dissolving zirconium oxynitrate, copper nitrate trihydrate, zinc nitrate hexahydrate, and iron nitrate nonahydrate in a solution of methanol and formic acid, respectively, and stirring to dissolve to obtain a mixed solution;

[0011] (2) adding tetrafluoroterephthalic acid to the mixed solution and stirring for a certain period of time;

[0012] (3) The obtained solid material is centrifuged and washed, and vacuum dried to obtain a metal organic framework material.

[0013] Wherein, in step (1), the molar ratios of zirconium oxynitrate to copper nitrate trihydrate, zinc nitrate hexahydrate, and iron nitrate nonahydrate are 4:1-1:1, respectively, and the volume ratio of methanol to formic acid is 5:1-2:1.

[0014] Wherein, in step (2), the stirring temperature is 30°C to 50°C, and the stirring time is 10 to 14 hours.

[0015] Wherein, the detergent in step (3) is methanol, the centrifugation speed is 3000 rpm / min, the centrifugation time is 10 min, and the centrifugation temperature is 10°C to 20°C; the vacuum drying temperature is 45°C to 60°C, the time is 8 to 10 h, and the drying pressure is -0.09 to -0.1 MPa.

[0016] The preparation method specifically comprises taking the metal organic framework material and the lycopene solution respectively, stirring, heating in a hot reflux water bath, and reacting in the dark; and filtering the lycopene mixed solution after the reaction.

[0017] The ratio of the metal organic framework material to lycopene is 4:1-2:1, the concentration of the lycopene solution is 0.1 mmol / L, the heating temperature is 25-50°C, and the heating time is 0.5-2h. Magnetic stirring is used, and the reflux water bath is heated, and the reaction is carried out in the dark; preferably, the heating temperature is 37.5°C and the heating time is 1h.

[0018] Principle of the invention: The preparation method of the present invention for promoting the cis-isomerization of lycopene utilizes a transition metal (Cu, Fe)-doped bimetallic organic framework material as a catalyst to achieve the isomerization of all-trans lycopene and improve its biological activity. The catalyst has the ability to accept electron pairs and is a Lewis acid. All-trans lycopene is rich in conjugated double bonds, which will create an electron-rich environment and is easily attacked by electrophiles, thus being a Lewis base. Therefore, the conjugated double bonds of all-trans lycopene are easily attacked and activated by the catalyst, thereby rotating into a corresponding configuration. Among them, the doping of appropriate amounts of Cu and Fe enhances the ability of the material to accept electrons, making the bimetallic organic framework material Cu 1 / 4 @UIO-66 and Fe 1 / 2 @UIO-66 has the best catalytic effect. 1 / 4 @UIO-66 and Fe 1 / 2 @UIO-66 is better than undoped, zinc-doped and other doped UIO-66 in terms of retention rate, total isomerization rate and 5-position isomerization rate, and is greener and more efficient.

[0019] Beneficial effects: Compared with the prior art, the present invention has the following significant advantages: (1) The preparation method of lycopene isomerization of the present invention uses metal organic framework materials or bimetallic organic framework materials as catalysts, is green and environmentally friendly, and has no metal catalyst residue; (2) Compared with the existing thermal isomerization method (isomerization rate 45.6%, retention rate 65.6%), the catalysis of the preparation method of the present invention is more efficient. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figure 1 is the ratio diagram of lycopene isomerization catalyzed by UIO-66 doped with different types and ratios of metals;

[0021] Figure 2 This is the liquid phase diagram of lycopene isomerization catalyzed by UIO-66;

[0022] Figure 3 is a graph of HUVEC cell viability assay;

[0023] Figure 4 is a graph of NIH 3T3 cell viability assay;

[0024] Figure 5 is the fluorescence image of cell viability;

[0025] Figure 6 This is a graph showing hemolysis determination of materials. DETAILED DESCRIPTION

[0026] The technical scheme of the present invention is further described below in conjunction with the examples. The test materials used in the examples can all be purchased through conventional channels.

[0027] Example 1

[0028] The preparation method of promoting cis-isomerization of lycopene of the present invention adopts Cu 1 / 4 -UIO-66 material is used as a catalyst to catalyze the cis-isomerization of lycopene.

[0029] Cu 1 / 4 - Preparation of UIO-66 material:

[0030] (1) Weigh 0.045 mmol of zirconium oxynitrate and 0.015 mmol of copper nitrate trihydrate and dissolve them in 7 mL of methanol and 1.5 mL of acetic acid. Stir at 40°C until they are completely dissolved.

[0031] (2) Add 1.429 mL of a methanol solution of tetrafluoroterephthalic acid (10 mg / mL) to the above solution, stir at 40°C for 12 h, and wash by centrifugation at 3000 rpm / min for three times, each time for 1 min.

[0032] (3) The washed precipitate was placed in a vacuum drying oven for drying (50° C., 8 h), and the vacuum pump was turned on to evacuate and dry until the pressure was -0.1 MPa, thereby obtaining the bimetallic organic framework material Cu of the present invention. 1 / 4 -UIO-66.

[0033] The specific preparation method of cis-isomerization of lycopene is as follows: 1 mg of metal organic framework material and 10 mL of lycopene solution (0.1 mmol / L) are added into a round-bottom flask, incubated at 37.5°C for 1 hour, stirred magnetically, heated in a hot reflux water bath, and the reaction is carried out in the dark.

[0034] Example 2

[0035] Compared with Example 1, in the preparation method for promoting cis-isomerization of lycopene, the catalyst is changed to Fe doped with iron ions. 1 / 2 -UIO-66, the doping molar amount is 50% of the total molar amount of metal ligands.

[0036] Fe 1 / 2 - Preparation of UIO-66 material:

[0037] (1) Weigh 0.03 mmol of zirconium oxynitrate and 0.03 mmol of ferric nitrate nonahydrate and dissolve them in 7 mL of methanol and 1.5 mL of acetic acid. Stir at 40°C until they are completely dissolved.

[0038] (2) Add 1.429 mL of a methanol solution of tetrafluoroterephthalic acid (10 mg / mL) to the above solution, stir at 40° C. for 12 h, and centrifuge and wash three times at 3000 rpm / min for 1 min each time.

[0039] (3) The washed precipitate was placed in a vacuum drying oven for drying (50° C., 8 h), and the vacuum pump was turned on to vacuum dry until the pressure was -0.1 MPa, thereby obtaining the bimetallic organic framework material Fe 1 / 2 -UIO-66.

[0040] Example 3

[0041] Compared with Example 1, in the preparation method for promoting cis-isomerization of lycopene, the catalyst is changed to UIO-66 material without metal ion doping:

[0042] Preparation of UIO-66 material:

[0043] (1) Weigh 0.06 mmol of zirconium oxynitrate and dissolve it in 7 mL of methanol and 1.5 mL of acetic acid. Stir at 40°C until it is completely dissolved.

[0044] (2) Add 1.429 mL of a methanol solution of tetrafluoroterephthalic acid (10 mg / mL) to the above solution, stir at 40° C. for 12 h, and centrifuge and wash three times at 3000 rpm / min for 1 min each time.

[0045] (3) The washed precipitate is placed in a vacuum drying oven for drying (50° C., 8 h), and the vacuum pump is turned on to evacuate and dry the mixture to a pressure of −0.1 MPa, thereby obtaining the metal organic framework material UIO-66 of the present invention.

[0046] Example 4

[0047] Compared with Example 1, in the preparation method for promoting cis-isomerization of lycopene, the catalyst is changed to Zn doped with zinc ions. 1 / 5 -UIO-66, the doping molar amount is 20% of the total metal ion molar amount.

[0048] Zn 1 / 5 - Preparation of UIO-66 material:

[0049] (1) Weigh 0.048 mmol of zirconium oxynitrate and 0.012 mmol of zinc nitrate hexahydrate and dissolve them in 7 mL of methanol and 1.5 mL of acetic acid. Stir at 40°C until they are completely dissolved.

[0050] (2) Add 1.429 mL of a methanol solution of tetrafluoroterephthalic acid (10 mg / mL) to the above solution, stir at 40° C. for 12 h, and centrifuge and wash three times at 3000 rpm / min for 1 min each time.

[0051] (3) The washed precipitate was placed in a vacuum drying oven for drying (50° C., 8 h), and the vacuum pump was turned on to evacuate and dry until the pressure was -0.1 MPa, thereby obtaining the bimetallic organic framework material Zn of the present invention. 1 / 5 -UIO-66.

[0052] Example 5

[0053] Compared with Example 1, in the preparation method for promoting cis-isomerization of lycopene, the catalyst is changed to zinc ion doping Zn 1 / 4 -UIO-66, the doping molar amount is 25% of the total metal ion molar amount.

[0054] Zn 1 / 4 - Preparation of UIO-66 material:

[0055] (1) Weigh 0.045 mmol of zirconium oxynitrate and 0.015 mmol of zinc nitrate hexahydrate and dissolve them in 7 mL of methanol and 1.5 mL of acetic acid. Stir at 40°C until they are completely dissolved.

[0056] (2) Add 1.429 mL of a methanol solution of tetrafluoroterephthalic acid (10 mg / mL) to the above solution, stir at 40° C. for 12 h, and centrifuge and wash three times at 3000 rpm / min for 1 min each time.

[0057] (3) The washed precipitate was placed in a vacuum drying oven for drying (50° C., 8 h), and the vacuum pump was turned on to evacuate and dry until the pressure was -0.1 MPa, thereby obtaining the bimetallic organic framework material Zn of the present invention. 1 / 4 -UIO-66.

[0058] Example 6

[0059] Compared with Example 1, in the preparation method for promoting cis-isomerization of lycopene, the catalyst is changed to zinc ion doping Zn 1 / 2 -UIO-66, the doping molar amount is 50% of the total metal ion molar amount.

[0060] Zn 1 / 2 - Preparation of UIO-66 material:

[0061] (1) Weigh 0.03 mmol of zirconium oxynitrate and 0.03 mmol of zinc nitrate hexahydrate and dissolve them in 7 mL of methanol and 1.5 mL of acetic acid. Stir at 40°C until they are completely dissolved.

[0062] (2) Add 1.429 mL of a methanol solution of tetrafluoroterephthalic acid (10 mg / mL) to the above solution, stir at 40° C. for 12 h, and centrifuge and wash three times at 3000 rpm / min for 1 min each time.

[0063] (3) The washed precipitate was placed in a vacuum drying oven for drying (50° C., 8 h), and the vacuum pump was turned on to evacuate and dry until the pressure was -0.1 MPa, thereby obtaining the bimetallic organic framework material Zn of the present invention. 1 / 2 -UIO-66.

[0064] Example 7

[0065] Compared with Example 1, in the preparation method for promoting cis-isomerization of lycopene, the catalyst is changed to Cu doped with copper ions. 1 / 5 -UIO-66, the added molar amount is 20% of the total metal ion molar amount.

[0066] Cu 1 / 5 - Preparation of UIO-66 material:

[0067] (1) Weigh 0.048 mmol of zirconium oxynitrate and 0.012 mmol of copper nitrate trihydrate and dissolve them in 7 mL of methanol and 1.5 mL of acetic acid. Stir at 40°C until they are completely dissolved.

[0068] (2) Add 1.429 mL of a methanol solution of tetrafluoroterephthalic acid (10 mg / mL) to the above solution, stir at 40° C. for 12 h, and centrifuge and wash three times at 3000 rpm / min for 1 min each time.

[0069] (3) The washed precipitate was placed in a vacuum drying oven for drying (50° C., 8 h), and the vacuum pump was turned on to evacuate and dry until the pressure was -0.1 MPa, thereby obtaining the bimetallic organic framework material Cu of the present invention. 1 / 5 -UIO-66.

[0070] Example 8

[0071] Compared with Example 1, in the preparation method for promoting cis-isomerization of lycopene, the catalyst is changed to Cu doped with copper ions. 1 / 2 -UIO-66, the added molar amount is 50% of the total metal ion molar amount.

[0072] Cu 1 / 2 - Preparation of UIO-66 material:

[0073] (1) Weigh 0.03 mmol of zirconium oxynitrate and 0.03 mmol of copper nitrate trihydrate and dissolve them in 7 mL of methanol and 1.5 mL of acetic acid. Stir at 40°C until they are completely dissolved.

[0074] (2) Add 1.429 mL of a methanol solution of tetrafluoroterephthalic acid (10 mg / mL) to the above solution, stir at 40° C. for 12 h, and centrifuge and wash three times at 3000 rpm / min for 1 min each time.

[0075] (3) The washed precipitate was placed in a vacuum drying oven for drying (50° C., 8 h), and the vacuum pump was turned on to evacuate and dry until the pressure was -0.1 MPa, thereby obtaining the bimetallic organic framework material Cu of the present invention. 1 / 2 -UIO-66.

[0076] Example 9

[0077] Compared with Example 1, in the preparation method for promoting cis-isomerization of lycopene, the catalyst is changed to iron ion doped Fe 1 / 5 -UIO-66, the doping molar amount is 20% of the total metal ion molar amount.

[0078] Fe 1 / 5 - Preparation of UIO-66 material:

[0079] (1) Weigh 0.048 mmol of zirconium oxynitrate and 0.012 mmol of ferric nitrate nonahydrate and dissolve them in 7 mL of methanol and 1.5 mL of acetic acid. Stir at 40°C until they are completely dissolved.

[0080] (2) Add 1.429 mL of a methanol solution of tetrafluoroterephthalic acid (10 mg / mL) to the above solution, stir at 40° C. for 12 h, and centrifuge and wash three times at 3000 rpm / min for 1 min each time.

[0081] (3) The washed precipitate was placed in a vacuum drying oven for drying (50° C., 8 h), and the vacuum pump was turned on to vacuum dry until the pressure was -0.1 MPa, thereby obtaining the bimetallic organic framework material Fe 1 / 5 -UIO-66.

[0082] Example 10

[0083] Compared with Example 1, in the preparation method for promoting cis-isomerization of lycopene, the catalyst is changed to iron ion doped Fe 1 / 4 -UIO-66, the doping molar amount is 25% of the total metal ion molar amount.

[0084] Fe 1 / 4 - Preparation of UIO-66 material:

[0085] (1) Weigh 0.045 mmol of zirconium oxynitrate and 0.015 mmol of ferric nitrate nonahydrate and dissolve them in 7 mL of methanol and 1.5 mL of acetic acid. Stir at 40°C until they are completely dissolved.

[0086] (2) Add 1.429 mL of a methanol solution of tetrafluoroterephthalic acid (10 mg / mL) to the above solution, stir at 40° C. for 12 h, and centrifuge and wash three times at 3000 rpm / min for 1 min each time.

[0087] (3) The washed precipitate was placed in a vacuum drying oven for drying (50° C., 8 h), and the vacuum pump was turned on to vacuum dry until the pressure was -0.1 MPa, thereby obtaining the bimetallic organic framework material Fe 1 / 4 -UIO-66.

[0088] In the preparation method of cis-isomerization of lycopene in Examples 1 to 10, the lycopene mixed solution after the reaction was filtered through a 0.22 μm polytetrafluoroethylene (PTFE) membrane filter and then subjected to high performance liquid chromatography analysis. Figure 2 As shown, the chromatographic peak at a retention time of 34 min is 13-cis lycopene, at 38 min is 9-cis lycopene, at 42 min is all-trans lycopene, and at 43 min is 5-cis lycopene. The calculation method for the total cis isomer content (%), the single isomer content (%) and the lycopene retention rate (%) is as follows:

[0089]

[0090] The isomerization results are shown in Table 1:

[0091] Table 1. Lycopene cis-isomerization results

[0092]

[0093]

[0094] As shown in Table 1, Cu 1 / 4- The retention rate of UIO-66 was 82.63%, the total isomerization rate was 60.30%, and the 5-cis isomerization rate was 40.20%. 1 / 2 -UIO-66 has a retention rate of 84.47%, a total isomerization rate of 46.95% and a 5-cis isomerization rate of 24.75%. Combining the retention rate, total isomerization rate and 5-cis isomerization rate analysis, it can be seen that Cu 1 / 4 -UIO-66 and Fe 1 / 2 -UIO-66 has the best effect in the cis-isomerization of lycopene. This is because the addition of appropriate amounts of Fe and Cu enhances the ability of UIO-66 to accept electrons, resulting in a higher cis-isomerization rate for lycopene.

[0095] In the above embodiment, Cu 1 / 4 -UIO-66 and Fe 1 / 2 -Biological safety study of UIO-66:

[0096] Human venous endothelial cells (HUVECs) and mouse embryonic fibroblasts (NIH 3T3) are preferably used for Cu 1 / 4 -UIO-66 and Fe 1 / 2 -UIO-66 cytotoxicity test. Both cell lines were cultured in DMEM at 37°C with 5% CO 2 in moist air.

[0097] CCK-8 was used to evaluate the cytotoxicity of HUVECs and NIH 3T3 cells. The cells were seeded on a 96-well plate and cultured for 24 h in DMEM medium containing the three antibodies. Subsequently, the original medium was discarded and a medium containing Cu 1 / 4 -UIO-66 and Fe 1 / 2 -UIO-66 (0.2, 0.1 mg / mL) in fresh medium. After incubation for 24 hours, wash the cells three times with PBS to remove adherent substances. Then add fresh medium containing 10% CCK-8. Incubate at 37°C for 0.5 h. Measure the absorbance at 450 nm with an enzyme marker to detect relative cell viability.

[0098] The AO / PI dual kit was used to determine live and dead cells. Specifically, the cell culture and material incubation experimental steps were the same as those of CCK-8, but the inoculation plate was a 14-well plate and the inoculation concentration was 1*105. In addition, considering the actual concentration of the material, the material incubation concentration was changed (0.5 mg / mL). After the incubation was completed, the dye was added and the cell fluorescence was recorded under a fluorescent inverted microscope (Nikon 80i).

[0099] like Figure 3 , Figure 4 The results of CCK-8 cell activity experiments showed that when the material concentration reached 0.2 mg / mL, the survival rate of HUVECs and NIH 3T3 cells remained above 80%. The cell live-death fluorescence experiment also verified that the live cells after incubation with the material maintained green fluorescence, while the dead cells had almost no red fluorescence ( Figure 5 ), the experimental results are consistent with the CC-K8 test results. At the same time, the results of the mouse red blood cell hemolysis experiment showed that ( Figure 6 ), 0.2 mg / mL Cu 1 / 4 -UIO-66 and Fe 1 / 2 -UIO-66 has a blood cell rupture rate far below 5%. 1 / 4 -UIO-66 and Fe1 / 2 -UIO-66 has high biosafety and has great application prospects in the field of food packaging.

Claims

1. A preparation method for promoting cis-isomerization of lycopene, characterized in that: The preparation method is to use the metal organic framework material UIO-66 or the bimetallic organic framework material as a catalyst to catalyze lycopene to make it cis-isomerize.

2. The preparation method according to claim 1, characterized in that: The bimetallic organic framework material has an octahedral crystal structure and is formed by coordination of an organic ligand tetrafluoroterephthalic acid and a metal ion. The metal ion is a zirconium ion, a copper ion, a zinc ion or an iron ion.

3. The preparation method according to claim 2, characterized in that: Among the metal ions, copper ions, zinc ions or iron ions are doped metal ions, and the molar amount of the doped metal ions is 20 to 50% of the total molar amount of the metal ions.

4. The preparation method according to claim 3, characterized in that: The bimetallic organic framework material is Zn 1 / 5 -UIO-66, Zn 1 / 4 -UIO-66, Zn 1 / 2 -UIO-66, Cu 1 / 5 -UIO-66, Cu 1 / 4 -UIO-66, Cu 1 / 2 -UIO-66, Fe 1 / 5 -UIO-66, Fe 1 / 4 -UIO-66 or Fe 1 / 2 -UIO-66.

5. The preparation method according to claim 2, characterized in that: The method for preparing the bimetallic organic framework material comprises the following steps: (1) dissolving zirconium oxynitrate, copper nitrate trihydrate, zinc nitrate hexahydrate, and iron nitrate nonahydrate in a solution of methanol and formic acid, respectively, and stirring to dissolve to obtain a mixed solution; (2) adding tetrafluoroterephthalic acid to the mixed solution and stirring for a certain period of time; (3) The obtained solid material is centrifuged and washed, and vacuum dried to obtain a metal organic framework material.

6. The method according to claim 5, characterized in that In step (1), the molar ratio of zirconium oxynitrate to copper nitrate trihydrate, zinc nitrate hexahydrate and iron nitrate nonahydrate is 4:1-1:1, and the volume ratio of methanol to formic acid is 5:1-2:

1.

7. The preparation method according to claim 5, characterized in that: In step (2), the stirring temperature is 30° C. to 50° C., and the stirring time is 10 to 14 h.

8. The preparation method according to claim 5, characterized in that: In step (3), the detergent is methanol, the centrifugation speed is 3000 rpm / min, the centrifugation time is 10 min, and the centrifugation temperature is 10°C to 20°C; the vacuum drying temperature is 45°C to 60°C, the time is 8 to 10 h, and the drying pressure is -0.09 to -0.1 MPa.

9. The preparation method according to claim 1, characterized in that: The preparation method specifically comprises taking the metal organic framework material and the lycopene solution respectively, stirring, heating in a hot reflux water bath, and reacting in the dark; and filtering the lycopene mixed solution after the reaction.

10. The preparation method according to claim 9, characterized in that: The ratio of the metal organic framework material to lycopene is 4:1-2:1, the heating temperature is 25-50° C., the heating time is 0.5-2 h, magnetic stirring is used, hot reflux water bath heating is performed, and the reaction is carried out in the dark.

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