A furan flavone compound for preventing oxidation deterioration of cigarette filter rod additives, a preparation method thereof and application thereof in cigarettes

Abstract

The application belongs to the technical field of phytochemistry, and particularly relates to a furan flavonoid compound for preventing oxidation and deterioration of a cigarette filter rod additive, a preparation method of the furan flavonoid compound and application of the furan flavonoid compound in cigarettes. 22 H 18 O6.The furan flavonoid compound of the application is isolated from a phyllanthus emblica, and activity research shows that the compound has outstanding antioxidant activity, can prevent oxidation and deterioration of filter rod flavoring fragrances, and prolongs the shelf life of the flavoring fragrances. Meanwhile, the application also prepares a composite additive relying on the flavonoid compound, and the composite additive has the effects of significantly scavenging smoke free radicals and improving the smoking quality of cigarettes. The production idea of the composite additive can also be copied to a cigarette burst bead core material solvent system, and provides a beneficial reference for solving the dissolution problem of a functional large polarity component in burst bead core material solvent glyceryl caprylate caprate and production of other new cigarette materials.

Description

Technical Field

[0001] This invention belongs to the field of phytochemistry technology, specifically relating to a furan flavonoid compound used to prevent the oxidative deterioration of cigarette filter rod additives, its preparation method, and its application in cigarettes. Background Technology

[0002] Flavonoids are a class of naturally occurring secondary metabolites widely found in plants. Their core structure is a C6-C3-C6 biphenyl ring linked by a three-carbon chain, and they are often referred to as bioflavonoids. Most flavonoids are yellow crystalline and slightly soluble in water. Based on characteristics such as the degree of oxidation of the three-carbon chain and the position of the B-ring, they can be divided into more than ten common types, such as: flavones, flavonols, dihydroflavones, dihydroflavonols, furanones, dihydrofuranones, chalcones, dihydrochalcones, aurones, and anthocyanins.

[0003] Flavonoids possess a wide range of biological activities, including antioxidant, anti-inflammatory, cardiovascular protection, immune regulation, adjuvant hypoglycemic agents, estrogen-like regulation, antitumor, and antiviral effects. Among these numerous activities, their potent antioxidant properties are most prominent. They directly scavenge free radicals through the hydroxyl and methoxy groups in their molecules, blocking lipid peroxidation chain reactions and reducing cellular oxidative damage. As food safety and health benefits become increasingly important concerns, the selection of food ingredients and even food additives is trending towards natural, healthy, and bioactive materials. Natural plants have become an important source of food antioxidants. The natural resources available for antioxidant development are extensive. The main structural types of natural substances with antioxidant properties include: flavonoids, tannins, vitamins, anthraquinones, nitrogen-containing compounds, phytic acid, sterols, phenylpropanoids, coumarins, and enoic acids.

[0004] In tobacco, flavonoids are important precursors of latent aroma (such as rutin and chlorogenic acid). During combustion and pyrolysis, they are converted into volatile aroma components, directly affecting the aroma quality, aroma quantity, and aftertaste comfort of the smoke. Their content is positively correlated with the grade of tobacco leaves. Some flavonoid derivatives are also used in tobacco additives, providing a throat-soothing effect, reducing throat irritation from smoke, making inhalation smoother, and improving the aftertaste. Purified flavonoid extracts (such as total flavonoids from raisins) can soften the smoke, increase its fullness, mask off-flavors, and improve the overall smoking quality. In addition, flavonoids are often made into flavored tobacco beads or coated onto cigarette paper, fixed with adhesives to ensure the effective release of active ingredients during smoking.

[0005] This application aims to provide a novel flavonoid compound and its uses. Summary of the Invention

[0006] This invention isolates a furan flavonoid compound from Phyllanthus emblica. Activity studies have shown that this compound exhibits outstanding antioxidant activity, preventing the oxidation and deterioration of flavorings and fragrances added to filter rods. Furthermore, this invention also utilizes this flavonoid compound to prepare a composite additive, which significantly scavenges free radicals in cigarette smoke and improves the smoking quality of cigarettes.

[0007] The first aspect of this application provides a furan flavonoid compound, the molecular formula of which is: C 22 H 18 O6 has the following structural formula:

[0008] .

[0009] This compound is a light yellow crystal, named 5,4'-dimethoxy-6-(4-hydroxymethylfuran-2-yl)flavone. It is also commonly known as Phyllanthus emblica furan flavone-A.

[0010] The second aspect of this application provides a method for preparing the aforementioned furan flavonoids, wherein the furan flavonoids are prepared from Phyllanthus emblica branches and leaves through extraction, reversed-phase resin separation, and high-performance liquid chromatography. The preparation method specifically includes the following steps:

[0011] A. Extraction of extract: Pulverize the branches of Phyllanthus emblica to 20-40 mesh to obtain material a. Extract material a with organic solvent by ultrasonic extraction 2-5 times, 30-60 minutes each time. Combine the extracts, filter, concentrate the extract under reduced pressure, let stand, filter out the precipitate to obtain extract b.

[0012] The organic solvent is a 70-80% methanol aqueous solution, a 70-80% ethanol aqueous solution, or a 50-60% acetone aqueous solution.

[0013] B. Reverse-phase resin separation: The extract b obtained in step A is passed through an MCI-GEL CHP20 reverse-phase resin column. The effluent is collected and concentrated under reduced pressure to remove organic solvents and obtain extract c.

[0014] The resin column is packed with resin using the ethanol wet packing method; the ratio of the inner diameter of the resin packing section to the effective packing length is 1:3 to 1:5; the total volume of extract b passing through the column is 15 to 20 times the resin packing volume.

[0015] C. Recrystallization and purification: The extract c obtained in step B is completely dissolved by heating with a 25-30% ethanol aqueous solution (pH adjusted to 2-3 with phosphoric acid), then allowed to cool slowly to crystallize. The precipitate is filtered out and washed with water to obtain total flavonoids d. The total flavonoid content is determined according to GB / T20574-2006 "Determination of Total Flavonoid Content in Propolis by Spectrophotometric Colorimetric Method". The total flavonoid content in the precipitate is ≥85%.

[0016] D. Preparative Chromatographic Separation: The total flavonoids d obtained in step C were dissolved in pure methanol. Preparative chromatographic separation was performed using an Asahipak NH2P-50GHILIC hydrophilic column as the stationary phase, with column parameters of 50 mm × 250 mm and packing particle size of 5 μm. Pure methanol was used as the mobile phase, with a flow rate of 60 mL / min and a detection wavelength of 376 nm. The chromatographic peak at 32.5 min was collected, and the solvent was removed by vacuum evaporation to obtain the furan flavonoids.

[0017] All percentages mentioned above are volume percentages.

[0018] The third aspect of this application provides a cigarette filter rod additive, which comprises the following substances in parts by weight: 1-2 parts of the furan flavonoid compound (i.e., amla furan flavonoid-A) described in the first aspect, 5-10 parts of cactus polysaccharide, 10-12 parts of tobacco pure oil, 1-2 parts of fructooligosaccharide monofatty acid ester, 0.2-0.3 parts of β-damastenone, 0.3-0.5 parts of phenylethanol, and 0.2-0.3 parts of citronellol.

[0019] Preferably, the above-mentioned cigarette filter rod additives are mixed and dissolved in triacetyl glycerol to obtain the free radical reduction additive for cigarette smoke of the present invention.

[0020] In the formulation of this invention, Phyllanthus emblica furan flavonoid-A is a strong antioxidant, which has significant effects in scavenging free radicals in cigarette smoke, preventing the oxidation and deterioration of flavoring and fragrance components, and extending the shelf life after flavoring. In addition, this flavonoid compound also has a significant sweet aftertaste effect. When used in cigarette products, it can significantly enhance the sweet aftertaste of cigarette smoke and improve the aftertaste of cigarette smoking.

[0021] Cactus polysaccharides are natural high-molecular-weight compounds extracted from cactus stems. They are natural and safe fixatives that can stabilize and slow-release aromas through various mechanisms, and are widely used in food, flavorings, and daily chemical industries. When used as additives, cactus polysaccharides can increase the stability of aroma component release. Cactus polysaccharides also enhance the smoothness of cigarette smoke.

[0022] Fructose monosodium esters are surfactants and food additives with both emulsifying and prebiotic properties. When used in additive formulations, they can significantly increase the solubility of highly polar components (cactus polysaccharides) in triacetin, forming a homogeneous and stable solution. Furthermore, they can achieve uniform dispersion and stable adsorption of added flavorings and fragrances on the filter rod fibers through mechanisms such as reducing interfacial tension, forming micellar solubilization / emulsification, and constructing interfacial adsorption films.

[0023] The preferred tobacco purifying oil is Yunnan tobacco purifying oil. Yunnan tobacco purifying oil is prepared from waste tobacco from Yunnan through extraction and molecular distillation. When added to the filter rod, it enhances the natural tobacco aroma of cigarettes and improves smoking quality. Other conventional tobacco purifying oils can also be used.

[0024] β-Damalenone, phenylethyl alcohol, and citronellol are monomeric flavorings. Their role in the formulation is to further enhance the tobacco purification effect and strengthen its fresh and sweet aroma characteristics through fine-tuning of the monomeric flavorings.

[0025] Triacetin is a plasticizer specifically for cellulose acetate tow in cigarette filter molding. During the cigarette filter molding process, the active ingredients in the compound formulation of this invention are easily added to the filter in combination with triacetin, which is technologically convenient and does not add any extra steps to the production process.

[0026] This cigarette filter additive has a significant effect on scavenging free radicals in cigarette smoke, and also improves the smoking quality of cigarettes. Furthermore, the amla furan flavonoid-A of this invention also provides the effect of preventing the added flavorings and fragrances in the filter from oxidizing and deteriorating, thus extending the shelf life of the flavorings and fragrances.

[0027] The fourth aspect of this application provides the application of the aforementioned furan flavonoids in cigarettes, wherein the furan flavonoids are used to prevent the oxidative deterioration of flavoring components and to reduce free radicals in cigarette smoke, thereby improving the smoking quality of cigarettes.

[0028] During the cigarette filter rod forming process, the additive of this invention is used as a plasticizer in the filter rod forming process, replacing the original plasticizer, and is added to the cigarette filter rod at 3-8% of the tow weight. The specific amount added and the composition ratio of the additive can be adjusted as needed according to the filter rod forming requirements within the scope of this application. After the filter rod is formed, the filter tip with the additive described in this invention is then rolled into a cigarette.

[0029] When flavorings and fragrances are added to cigarette filters, the increased surface area exposed to air makes them prone to oxidation and deterioration. Over time, this leads to a decline in aroma quality and even the development of off-odors. This is a major reason why the use of flavoring filters in cigarette products is limited. The flavonoids in this invention possess outstanding antioxidant activity and also prevent the oxidation and deterioration of flavoring and fragrance components.

[0030] This application has the following advantages:

[0031] (1) The furan flavonoids of this invention are isolated from the branches and leaves of Phyllanthus emblica. Phyllanthus emblica is a deciduous small tree or shrub, 3-8 m tall, tolerant of poor soil, and widely distributed in the barren mountainous areas of the dry and hot river valleys of Yunnan, such as the Jinsha River, Lancang River, Yuan River, and Nu River. Compared with the fruit, the branches and leaves of Phyllanthus emblica have a very high biomass yield, and regenerate the following year after harvesting, making them a renewable resource. Therefore, this application uses Phyllanthus emblica branches and leaves as raw materials, providing a wide range of raw material sources for the preparation of active compounds at a low cost.

[0032] (2) This invention employs a process of solvent extraction, reversed-phase resin separation to remove impurities, recrystallization to separate total flavonoids, and preparative chromatographic purification. Because a large amount of impurities are removed during reversed-phase resin separation and recrystallization, the load on the preparative chromatography is greatly reduced compared to traditional methods. Furthermore, this invention uses pure methanol as the mobile phase and a HILIC hydrophilic column for preparative separation. Compared to conventional forward preparative chromatography, the target compound will not be adsorbed and lost or tailed on silica gel during separation; compared to reversed-phase preparative chromatography, it avoids the problem of difficult solvent evaporation and removal due to the large amount of water used in the mobile phase. The new method allows for a large sample loading per injection, resulting in high purity of the prepared target compound. The preparation process is mature and simple, making it easy to scale up for industrial production.

[0033] (3) The furan flavonoids of this invention exhibit outstanding antioxidant activity and also prevent the oxidative deterioration of cigarette filter rod additives, providing a practical new approach to solving the problem of "filter rod flavoring being easily oxidized and deteriorated after the addition of flavorings and fragrances". In addition, this application also relies on Phyllanthus emblica furan flavonoid-A and, through a scientific and reasonable formulation combination, has developed a composite additive that significantly reduces free radicals in cigarette smoke. In addition to reducing free radicals in cigarette smoke, this additive also has the effect of significantly improving the smoking quality of cigarettes.

[0034] (4) In the process of making composite additives, this application uses polyfructose monofatty acid ester as a co-solvent, successfully solving the problem of dispersing highly polar polysaccharides in the low-polarity solvent triacetylglycerol. Polyfructose monofatty acid ester has been successfully used in food, liquor, and beverages; moreover, the constituent components of this compound, fructose and fatty acids, are homologous to the main components of tobacco. Compared with other surfactants such as polysorbate, it has a food-grade safety basis and does not introduce unpleasant odors. This approach can also be replicated in the solvent system of cigarette pod-filled core materials, providing a useful reference for solving the problem of dissolving functional highly polar components in the solvent caprylic / capric triglyceride of pod-filled core materials, as well as for the production of other new tobacco materials. Attached Figure Description

[0035] Figure 1 The carbon NMR spectrum of Phyllanthus emblica furan flavonoid-A is shown in this application.

[0036] Figure 2 The 1H NMR spectrum of Phyllanthus furan flavonoid-A in this application is shown.

[0037] Figure 3 This is a key HMBC correlation diagram for Phyllanthus emblica furan flavonoid-A in this application. Detailed Implementation

[0038] The present application will be described below with reference to specific embodiments, but the implementation of the present application is not limited thereto. Experimental methods not specifically described in the embodiments generally use conventional conditions, conditions described in manuals, or conditions recommended by the manufacturer. The general equipment, materials, reagents, etc., used are all commercially available unless otherwise specified. The raw materials required in the following embodiments and comparative examples are all commercially available.

[0039] Example 1

[0040] The branches and leaves of this Phyllanthus emblica originated from Binchuan County, Dali, Yunnan Province.

[0041] A method for preparing furan flavonoids:

[0042] The furan flavonoids are prepared and separated from Phyllanthus emblica branches and leaves through a process involving extract extraction, reversed-phase resin separation, and high-performance liquid chromatography. Specifically:

[0043] A. Extraction of extract: The branches and leaves of Phyllanthus emblica are crushed to 20-40 mesh to obtain material a. Material a is extracted with organic solvent by ultrasonic extraction 5 times, 45 minutes each time. The extracts are combined, filtered, concentrated under reduced pressure, allowed to stand, and the precipitate is filtered out to obtain extract b.

[0044] The organic solvent is an ethanol aqueous solution with a volume percentage of 70%;

[0045] B. Reverse-phase resin separation: The sample extract b is passed through an MCI-GEL CHP20 reverse-phase resin column, the eluent is collected and concentrated under reduced pressure to remove organic solvents and obtain extract c;

[0046] The resin column is packed with resin using the ethanol wet packing method; the ratio of the inner diameter of the resin packing section to the effective packing length is 1:5; the total volume of extract b passing through the column is 18 times the resin packing volume;

[0047] C. Recrystallization and purification: The extract c obtained in step B is completely dissolved by heating in a 30% (v / v) aqueous ethanol solution (pH adjusted to 3 with phosphoric acid). The solution is then allowed to cool slowly for crystallization. The precipitate is filtered out and washed with water to obtain total flavonoids d. The total flavonoid content in the precipitate is determined according to GB / T 20574-2006 "Determination of Total Flavonoid Content in Propolis - Spectrophotometric Colorimetric Method". The total flavonoid content in the precipitate is ≥85 wt%.

[0048] D. Preparative Chromatographic Separation: The total flavonoids were dissolved in pure methanol. Preparative chromatographic separation was performed using an Asahipak NH2P-50G HILIC hydrophilic column (50 mm × 250 mm, 5 µm) as the stationary phase and pure methanol as the mobile phase. The detection wavelength was 376 nm, and the chromatographic peak at 32.5 min was collected. The solvent was removed by vacuum evaporation to obtain the furan flavonoids of this application.

[0049] Identification of the flavonoids:

[0050] The compound appears to be a light yellow crystal.

[0051] Its high-resolution mass spectrometry (m / z 401.0993) indicates [M+Na] + (Calculated value: 401.0996) Its molecular formula can be determined to be C. 22 H 18 O6 has an unsaturation degree of 14.

[0052] compound 1 H, 13 C10 NMR and DEPT spectral data (Table-1, Figures-1 and-2) show 22 carbons and 18 hydrogens. These signals can be classified as one 1,2,3,4-tetrasubstituted benzene ring (C-5~C-10, H-7 and H-8), one 1,4-disubstituted benzene ring (C-1'~C-6', H2-2', 6' and H2-3', 5'), a group of α,β-unsaturated carbonyl groups (-CO-CH=C-, C-2~C-4, H-3), one 4-hydroxymethylfuran-2-yl structural fragment (-(C4H2O)-CH2OH, C-2''~C-6'', H-3'', H-5'', H2-6''), and two methoxy groups (δ... C56.0 q, 61.0 q and δ H (3.81 s and 3.83 s). Removing the 8 unsaturations of the two benzene rings, the 2 unsaturations of the α,β-unsaturated carbonyl groups, and the 3 unsaturations of the furan ring, the compound should have one more ring to support the 14 unsaturations. Further analysis of its NMR data revealed two oxidized aromatic quaternary carbons (C-9 and C-2), suggesting that C-9 and C-2 are connected by oxygen atoms and form a six-membered pyran ring with the benzene ring, indicating that the compound should be a flavonoid structure. This flavonoid structure hypothesis can be further confirmed by the HMBC correlations between H-3 and C-4 / C-10 / C-1′, and H-2′ and C-2 (Figure 3). Furthermore, the presence of the 4-hydroxymethylfuran-2-yl structural fragment in the compound can also be confirmed by the HMBC correlations between H-3'' and C-2'' / C-4'' / C-5'' / C-6'', H-5'' and C-2'' / C-3'' / C-4'', and H2-6'' and C-3'' / C-4'' / C-5''.

[0053] Table 1. Compounds 1 H and 13 CNMR data (500 and 125 MHz, CDCl3)

[0054]

[0055] Once the parent structure of the compound was confirmed, the other signals (4-hydroxymethylfuran-2-yl and two methoxy groups) could be considered as substituents. These substituents are identified by the two methoxy hydrogens (δ-hydroxymethylfuran-2-yl and two methoxy groups). H The 3.81 s and 3.83 s) ions show HMBC correlations with C-5 and C-4′, respectively, confirming that the two methoxy groups are substituted at C-5 and C-4′ positions. The substitution of the 4-hydroxymethylfuran-2-yl structural fragment at C-6 is confirmed by HMBC correlations between H-3'' and C-6, and H-7 and C-2''. Thus, the structure of the compound is accurately determined. Its systematic name is 5,4'-dimethoxy-6-(4-hydroxymethylfuran-2-yl)flavone.

[0056] UV, IR, and mass spectrometry data of the compound: UV spectrum (methanol) λ max (log ε) 376 (3.79), 279 (3.89), 215 (4.20) nm; Infrared spectrum (potassium bromide tablet): ν max3398, 3150, 3061, 2983, 28351666, 1619, 1544, 1461, 1352, 1273, 1160, 1069, 852 cm –1 ; 1 H and 13 C10 NMR data (500 and 125 MHz, deuterated chloroform solvent), see Table 1; ESIMS m / z 401; HRESIMS m / z 401.0993 [M+Na] + (Calculated value C) 22 H 18 NaO6, 401.0996).

[0057] Application Example 1

[0058] Antioxidant activity test of the compound: Using vitamin C as a positive control, the antioxidant activity of this furan flavonoid compound was tested. Antioxidant activity was expressed as the ability to scavenge DPPH (1,1-diphenyl-2-trinitrophenylhydrazine) free radicals. The activity of scavenging lipid free radicals DPPH was determined using an initial screening concentration of 50 μg / mL. A Costar 96-well plate was used, and freshly prepared DPPH ethanol solution (DPPH powder dissolved in anhydrous ethanol to prepare the working solution, with a DPPH concentration of 6.5 × 10⁻⁶) was added. -5 Add 190 μL of the test sample (furan flavonoids from Example 1) to each well, and 10 μL of physiological saline to each blank well. Mix thoroughly, seal with a sealing film, and incubate at room temperature (20°C) for 30 minutes in the dark. Measure the absorbance of each well using a UV2401 spectrophotometer at a wavelength of 517 nm. The DPPH scavenging rate of the test sample is calculated using the following formula:

[0059] DPPH clearance rate (%) = (A 空白 -A 样品 ) / A 空白 ×100%

[0060] A 空白 : Absorbance value of blank control group; A 样品 : Add the absorbance value of the sample group.

[0061] Based on the clearance rate fitting curves of multiple concentration gradients, the half-maximal inhibitory concentration (IC50) was calculated. 50 (Sample concentration that can remove 50% of DPPH free radicals).

[0062] The sample was analyzed in five parallel runs. The results showed that the IC50 of the compound in Example 1 was... 50The value was 3.76 μg / mL. This is superior to Vitamin C (IC50). 50 The value is 5.48 μg / mL. Therefore, the compound of this application exhibits good antioxidant activity.

[0063] Example 2

[0064] An additive formulation includes: 2 g of Phyllanthus emblica furan flavonoid-A, 10 g of cactus polysaccharide, 12 g of Yunnan tobacco pure oil, 2 g of fructooligosaccharide monofatty acid ester, 0.3 g of β-damalenone, 0.5 g of phenylethanol, and 0.3 g of citronellol. The above substances are mixed and dissolved in 2.5 L of triacetylglycerol to obtain the additive for reducing free radicals in cigarette smoke as described in this application.

[0065] In the cigarette filter rod forming process, the additive of this application replaces the plasticizer in the filter rod forming process and is added to the cigarette filter rod at 6% of the tobacco tow mass. After the filter rod is formed, the cigarette filter rod with the additive of this application is then rolled into a cigarette.

[0066] Application Example 2

[0067] Cigarettes produced in Example 2 were used as test samples, and cigarettes made with normal filter rods (without the additives of this application, using conventional plasticizers) were used as control samples for the detection of free radicals in cigarette smoke.

[0068] The method for detecting free radicals in cigarette smoke is as follows: Cigarettes are smoked under standard conditions using an RM200 type 20-channel automatic smoking machine. The mainstream particulate matter in the smoke is collected using a 44 mm Cambridge filter, and the gas phase is collected using a sampling tube. Particulate free radicals are extracted from the Cambridge filter using a benzene solution containing 0.05 mol / L N-tert-butyl-α-phenylazine as the extractant. The Cambridge filter is then washed, and the solution is brought to a final volume to obtain the particulate free radical test solution. Gas phase free radicals are collected using a free radical sampling tube with a benzene solution containing 0.05 mol / L N-tert-butyl-α-phenylazine as the absorbent. After the cigarette is finished smoking, the gas phase free radical sampling tube is removed, and the exterior of the ventilation tube and the inner wall of the sampling tube are rinsed three times with a small amount of absorbent. The absorbent and washing solutions are combined to obtain the gas phase free radical sample solution.

[0069] Free radicals were determined using a paramagnetic resonance spectrometer. ESR analysis experimental conditions: central magnetic field = 3.385 T, scan width = 0.500 T, microwave frequency = 1.5 GHz, scan time = 2 min, number of scans = 5, magnification = 10. 3 ~10 5(Adjusted according to peak height), sample volume 20 μL. Changes in the number of gas-phase and particulate free radicals were calculated based on the peak area in the ESR spectrum. Five experiments were conducted. Compared to the control sample, the reduction rate of gas-phase free radicals in cigarettes with the additive of this application was 29.5%–36.6%, and the reduction rate of particulate free radicals was between 26.8% and 33.6%. This indicates that the additive of this application has outstanding free radical scavenging effect.

[0070] Application Example 3

[0071] When flavorings and fragrances are added to cigarette filters, their surface area exposed to air increases dramatically, making them prone to oxidation and deterioration. Over time, this leads to a decline in aroma quality and even the development of off-odors. This is a major reason why the use of flavoring filters in cigarette products is limited. The flavonoids in this application exhibit outstanding antioxidant activity and also prevent the oxidation and deterioration of flavoring and fragrance components. To verify the effectiveness of the compounds in preventing oxidation and deterioration of flavorings and fragrances and extending shelf life, the following verification tests were conducted:

[0072] In the additive formulation of Example 2 of this application, Phyllanthus furan flavonoid-A is not added. The remaining components are the same as the aforementioned additive formulation. The same amount is added to the cigarette filter rod to replace the plasticizer in the filter rod forming process to make cigarettes as a control sample.

[0073] Cigarettes containing the additive formulation of Example 2 of this application were used as test samples. The test and control cigarettes were stored under the same conditions for 3, 6, 9, 12, and 15 months. The aroma of the cigarette samples was then assessed.

[0074] The test results showed that the control cigarettes had a noticeable off-odor after 9 months of storage, and the off-odor intensified after 15 months. However, the cigarettes containing the furan flavonoid compounds of this application did not exhibit a noticeable off-odor after 15 months of storage. This indicates that the furan flavonoid compounds of this application, in addition to their outstanding effect in scavenging free radicals in cigarette smoke, also have a significant effect in preventing oxidation and deterioration of the filter rod after the addition of flavorings and fragrances, and in extending the shelf life of the flavorings and fragrances.

[0075] Application Example 4

[0076] Sensory evaluation of cigarette samples: Cigarettes made with normal filter rods (without the additives of this application, using pure triacetyl ester as a plasticizer) were used as control samples, and cigarettes from Example 2 were used as test samples. The test and control cigarettes were subjected to sensory evaluation by professional smokers in accordance with the standard GB5606.4-2005 Cigarettes Part 4 Sensory Technical Requirements.

[0077] The specific results are as follows: after adding the additives of this application, the irritation of cigarette smoking is slightly reduced, the amount and richness of aroma are increased, the fresh and sweet characteristics of the smoke are enhanced, the impurities are slightly reduced, and the irritation of the aftertaste is slightly improved.

Claims

1. A furan flavonoid compound for preventing the oxidative deterioration of cigarette filter rod additives, characterized in that, The molecular formula of the furan flavonoids is: C 22 H 18 O6 has the following structural formula: 。 2. A method for preparing the furan flavonoid compound according to claim 1, characterized in that, The preparation method includes the following steps: A. Extraction of extract: Pulverize the branches of Phyllanthus emblica to 20-40 mesh to obtain material a. Extract material a with organic solvent by ultrasonic extraction 2-5 times, 30-60 minutes each time. Combine the extracts, filter, concentrate the extract under reduced pressure, let stand, filter out the precipitate to obtain extract b. The organic solvent is a 70-80% methanol aqueous solution, a 70-80% ethanol aqueous solution, or a 50-60% acetone aqueous solution. B. Reverse-phase resin separation: The extract b obtained in step A is passed through an MCI-GEL CHP20 reverse-phase resin column. The effluent is collected and concentrated under reduced pressure to remove organic solvents and obtain extract c. The resin column is packed with resin using the ethanol wet packing method; the ratio of the inner diameter of the resin packing section to the effective packing length is 1:3 to 1:5; the total volume of extract b passing through the column is 15 to 20 times the resin packing volume. C. Recrystallization and purification: The extract c obtained in step B is heated to completely dissolve in a 25-30% aqueous ethanol solution, then allowed to cool slowly to crystallize. The precipitate is filtered out and washed with water to obtain total flavonoids d. The pH of the ethanol-water solution was adjusted to 2-3 using phosphoric acid. D. Preparative Chromatographic Separation: The total flavonoids d obtained in step C were dissolved in pure methanol. Preparative chromatographic separation was performed using an Asahipak NH2P-50G HILIC hydrophilic column as the stationary phase, with column parameters of 50 mm × 250 mm and packing particle size of 5 μm. Pure methanol was used as the mobile phase, with a flow rate of 60 mL / min and a detection wavelength of 376 nm. The chromatographic peak at 32.5 min was collected, and the solvent was removed by vacuum evaporation to obtain the furan flavonoids. All percentages mentioned above are by volume.

3. A cigarette filter rod additive, characterized in that, The cigarette filter rod additive comprises the following components by weight: 1-2 parts of the furan flavonoid compound as described in claim 1, 5-10 parts of cactus polysaccharide, 10-12 parts of tobacco pure oil, 1-2 parts of fructooligosaccharide monofatty acid ester, 0.2-0.3 parts of β-damastenone, 0.3-0.5 parts of phenylethanol, and 0.2-0.3 parts of citronellol.

4. The application of the furan flavonoid compound of claim 1 in cigarettes, characterized in that, The furan flavonoids are used to prevent the oxidative deterioration of flavoring components, reduce free radicals in cigarette smoke, and improve the smoking quality of cigarettes.

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