Reduction of amines and nitrosamines in cigarette smoke vapors through a filter functionalized with olive tree polyphenols

Abstract

The traditional filters used in cigarettes are found to be ineffective in trapping the toxic chemical compounds which cigarette produces during combustion. The current invention aims to provide systems and methods (or to a universal filter) to reduce amines and nitrosamines in cigarette smoke vapors through a filter functionalized with olive tree polyphenols. Amines and Nitrosamines are highly toxic chemicals in the smoke and aerosol of a combusted cigarette. Olive polyphenols are able to trap amines and nitrosamines by establishing weak and strong interactions with these compounds by trapping these compounds in the filter.

Claims

1. A method for improving cigarette filter function that includes the use of a compound to inhibit the formation of toxic compounds including a of mines and/or nitrosamines in smoke vapors and/or cigarette aerosol, where the inhibitor includes at least one olive tree polyphenolic compound, functionalized to the filter.

2. A method, according to claim 1, that includes an alternative approach to improve the reduction of amines and/or nitrosamines in smoke vapor and/or cigarette aerosol by using a filter functionalized with at least one olive tree polyphenolic compound.

3. A method, according to any preceding claim, in which the filter includes a universal cigarette and/or vaping device filter functionalized with at least one olive tree polyphenolic compound.

4. A method, according to any preceding claim, in which toxic compounds include at least one of the compounds belonging to aromatic amines, including but not limited to Aniline, Anisidine, O-Toluidine, 1-Naphthylamine, 2-Naphthylamine, 3-Aminobiphenyl, 4-Aminobiphenyl, 2,4,6-Trimethylaniline.

5. A method, according to any preceding claim, in which the toxic compounds include at least one of the compounds belonging to nitrosamines, including but not limited to NNN (N-nitrosonornicotine), NNK ((4-methylnitrosamino)-1-(3-pyridyl)-1-butanone), NAB (N-nitrosoanabasine), NAT (N-nitrosoanatabine).

6. A method, according to any preceding claim, in which at least one olive polyphenolic compound, including hydroxytyrosol, tyrosol, oleuropein, homovanillic acid, oleanolic acid, apigenin, luteolin, elenolic acid.

7. A method, according to any preceding claim, in which at least one polyphenolic compound of the olive tree, belonging to phenolic acids, Phenolic acids, flavonoids, stilbenes, lignans, flavonols, flavanols, flavones, flavanones, isoflavones, anthocyanidins, and anthoxanthins.

8. A method, according to any preceding claim, in which the filter is usable as a universal device in the cigarette and/or to be attached to the cigarette and/or vaping devices.

9. According to any preceding claim, a polymer-based universal filter for cigarettes and/or vaping devices that includes an inhibitor to inhibit the formation of toxic reactive compounds within the cigarette and/or in the aerosol formed by it, where the inhibitor includes at least one olive tree polyphenolic compound, functionalized to the universal filter, where functionalization includes chemical reactions for covalent and noncovalent bond formation between the polyphenolic compound and the polymer base of the universal filter.

10. A filter, according to any preceding claim, where toxic compounds include at least one of the compounds belonging to aromatic amines, including but not limited to Aniline, Anisidine, O-Toluidine, 1-Naphthylamine, 2-Naphthylamine, 3-Aminobiphenyl, 4-Aminobiphenyl, 2,4,6-Trimethylaniline.

11. A filter, according to any preceding claim, in which the toxic compounds include at least one of the compounds belonging to nitrosamines, including but not limited to NNN (N-nitrosonornicotine), NNK ((4-methylnitrosamino)-1-(3-pyridyl)-1-butanone), NAB (N-nitrosoanabasine), NAT (N-nitrosoanatabine).

12. A filter, according to any preceding claim, in which at least one olive tree polyphenolic compound, including hydroxytyrosol, tyrosol, oleuropein, homovanillic acid, oleanolic acid, apigenin, luteolin, elenolic acid.

13. A filter, according to any preceding claim, in which at least one olive tree polyphenolic compound, belonging to phenolic acids, Phenolic acids, flavonoids, stilbenes, lignans, flavonols, flavanols, flavones, flavanones, isoflavones, anthocyanidins, and anthoxanthins.

14. A filter, according to any preceding claim, that can be used as a universal device for use in the cigarette and/or to attach to the cigarette and/or vaping devices.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0018] The accompanying figures, where like reference numerals refer to identical or functionally similar elements throughout the separate views, together with the detailed description below, are incorporated in and form part of the specification, and serve to illustrate further embodiments of concepts that include the claimed invention and explain various principles and advantages of those embodiments.

[0019] FIG. 1 shows the exploded view of the claimed assembly.

[0020] FIG. 2 shows another view of the claimed assembly per preferred embodiments of the invention. FIG. 3a-h C shows the comparative analysis of plots in which the spectra of the detected compounds are: [0021] The black spectrum refers to the compounds detected in the cigarette smoke with NC filter. [0022] The red spectrum refers to the compounds detected in the cigarette smoke with PT filter.

[0023] Table 1 shows the most significant molecules in which there was diminution of the signal acquired from smoke and aerosols in the PT filter compared with the NC filter as per preferred embodiments of the invention.

[0024] Skilled artisans will appreciate those elements in the figures are illustrated for simplicity and clarity and have not necessarily been drawn to scale. For example, the dimensions of some of the elements in the figures may be exaggerated relative to other elements to help to improve understanding of embodiments of the present invention.

DETAILED DESCRIPTION

[0025] Detailed descriptions of the preferred embodiment are provided herein. However, it is to be understood that the present invention may be embodied in various forms. Therefore, specific details disclosed herein are not to be interpreted as limiting but rather as a basis for the claims and as a representative basis for teaching one skilled in the art to employ the present invention in virtually any appropriately detailed system, structure, or manner.

[0026] The terminology used herein is to describe particular embodiments only and is not intended to be limiting to the invention. As used herein, and/or includes any and all combinations of one or more of the listed items. As used herein, the singular forms a, an, and the are intended to include the plural forms as well as the singular forms unless the context indicates otherwise. It will be further understood that the terms comprises and/or comprising, when used in this specification, specify the presence of stated features, steps, operations, elements, and/or components but do not preclude the presence or addition of one or more other features, steps, operations, elements, components, and/or groups thereof.

[0027] The present invention is directed to provide a new and improved system of reduction of amines and nitrosamines in cigarette smoke vapors through a filter functionalized with polyphenols from the olive tree.

[0028] With reference to the drawings, the invention will now be described in detail concerning the best modes and the preferred embodiments.

[0029] The assembly aims at an alternative approach to improve the function of a traditional cigarette filter by functionalizing the filter using olive tree polyphenols as shown in FIG. 1.

[0030] When the chemical properties of polyphenols are observed, the reaction that causes a trap between the electrophilic carbons of either aldehydes or ketones and the catechol group occurs due to an aromatic substitution reaction electrophilic by nature. Furthermore, polyphenols can also react to form strong and weak interactions with amines and nitrosamines, as well as carbonyl groups.

[0031] It is unarguably true that the field of filter design has been enriched with numerous valuable contributions from researchers for more than 30 years. Data and findings from the research show that filter ventilation has been misleading smokers, making them think that it makes cigarettes taste milder and lighter (Caroll et al., 2021; Borland et al., 2004; Yong et al., 2011). Secondly, it also develops compensation mainly by providing the idea of taking the larger puffs. Thirdly, for a cigarette that is heavily ventilated (that is, >65% air diluted), blocking of vents with lips or fingers is an additional contributor to compensatory smoking (Kozlowski et al., 2002). Though smokers have such beliefs and advertising claims, filters have significantly less health benefits, and filter tip ventilation can also cause an increase in the health risks caused by smoking (Silva et al., 2021). Despite many modifications in cigarette filters, newer cigarettes with reduced amounts of nicotine and carbon monoxide do not have a lower risk of myocardial infarction than those who smoke cigarettes containing larger quantities of these substances (Kaufman et al., 1983).

[0032] Hydroxytyrosol (HXT) or (or 4-(2-di hydroxyphenyl) ethanol) is one of the most powerful extracts, extracted from olive leaves and fruit, that act as a natural antioxidant that lies just below gallic acid (Martinez et al., 2018). The antioxidant functions which it shows have been proved in vitro studies; with intense flavor and aroma, it protects health; and its precursor is oleuropein which is its precursor (Yadav and Singh, 2004; Wang et al., 2013). Several studies have shown that HXT, which is known to be a highly bioactive ortho-diphenol, has interesting antioxidant and antimicrobial characteristics and important beneficial effects on the cardiovascular system and several human diseases (Martinez et al., 2018; Bertelli et al., 2018; Caberizo et al., 2013; Yangui et al., 2009; Leger et al., 2005; Bisignano et al., 1999).

[0033] As per further embodiments, Nitrosamines have been seen to be constituents of food, beverage, air, cigarette smoke, cosmetics, and industrial environments, and tobacco-specific nitrosamines are also major compounds present in tobacco which are needed to be studied and reviewed well. (IARC 17 1978; Banbury Report 1982; Magee 1996; Lin 1990; Preussmann and Eisenbrand 1984; Preston-Martin and Correa 1989; Tricker 1997; Magee 1989; Tricker et al. 1989; Startin 1996; Loeppky and Michejda 1984; Eisenbrand et al. 1996; Scanlan 1999;). Tobacco-specific nitrosamines (TSNAs) are a group of carcinogens generated in tobacco smoke. They get produced from nicotine and related alkaloids while processing tobacco and tobacco products. The most common Tobacco specific nitrosamines are: NNN (N-nitrosonornicotine), NNK ((4-methylnitrosamino)-1-(3-pyridyl)-1-butanone), NAB (N-nitrosoanabasine) and NAT (N-nitrosoanatabine) (Hoffman et al., 1982). The research conducted on hamster rats showed that NNN and NNK induced tumors in the upper respiratory tract of the rats and that NNK is the most effective and active carcinogen of TSNA that induce adenoma and adenocarcinoma in the human lung. Such harmful effects on the consumer's lungs can also be predicted in humans (Hoffman et al., 1982; Konstantinou et al., 2018; Pool-Zobel et al., 1992; Levy et al., 2004; Arredondo et al., 2006; Ashley et al., 2010). Among nicotine-derived carcinogens, the most important one is nitrosamine is 4-(methylnitrosoamino)-1-(3-pyridyl)-1-butanone (NNK). Secondary reduction of NNK degrades to 4-(methylnitrosoamino)-1-(3-pyridyl)-1-butanol (NNAL), which has an adverse health effect (Matt et al., 2011). So, the invention is needed to reduce such compounds through the functionalization of cigarettes.

[0034] The development of the proposed assembly is completed in multiple steps. The first step involves Cellulose acetate for making a filter. The cellulose acetate filters for utilization in cigarette is one of the popular methods of creating a filter. Since cellulose acetate filters are common in cigarettes, the research (Markosyan et al., 1971) is worth studying and discussing. As described, it used fibrous material, staple, calcium chloride, and acetic acid as chemical reagents, stainless steel tube, Teflon capsule, glass joint, heating tube, heater coil, ground-glass joint, glass calibration ampoule, spectrometer, commercial grade triacetate and secondary acetate fibers and equipment for titration.

[0035] Discussing the method used in (Markosyan et al., 1971), firstly, fibrous material was cut into pieces, the staple was comped, and placed into an exsiccator over calcium chloride. Stainless steel tube was used to secure one end of the capsule, and another end was provided with a glass joint. An airflow of about 17.5 ml/sec was drawn into the systematic assessment of the sorption power of a fibrous material was done, and the other end of the capsule was used to measure the air resistance. The proportion of the remaining substance in the filter paper was calculated after elution with solvents by spectrophotometric or titrimetric analysis. Fibers were spun to make them wet, having acetic acid as an aqueous bath.

[0036] The second step is functional nanocoating over the surface of filters. The research regarding functional nanocoating over the surface of the filter evaluates the application in making commercial cigarette filters (Sadabad et al., 2019). Regarding the reagents and materials, as described, the reagents such as pyrogallol (PG), gallic acid (GA), pyrocatechol (Ctl), epigallocatechin gallate (EGCG), tannic acid (TA), catechin (Ctn), hydroxyhydroquinone (HHQ), caffeic acid (CA), and morin, some of the most common plant-derived phenolic compounds in the presence of sodium ascorbate (SA), glutathione (GSH), and uric acid (UA) as natural antioxidants were used. Phenolic compounds were slowed down in their Kinetics of oxidation value with the help of three naturally occurring antioxidants, including sodium ascorbate (SA), glutathione (GSH), and uric acid (UA). The Kinetics of oxidation of phenolic compounds was slowed down by using three natural antioxidants, including sodium ascorbate (SA), glutathione (GSH), and uric acid (UA).

[0037] As per further embodiments, in the study (de Falco et al., 2020) performed for reducing toxic carbonyl species in e-cigarettes, in vitro Reactive Carbonyl Species (RCS) trapping properties of gallic acid, hydroxytyrosol and epigallocatechin were studied based on their chemical structures and also in accordance to their ability to form adducts with glyoxal and methylglyoxal. Glycerol and propylene glycol, 2,4-dinitrophenylhydrazine (DNPH; 4% in phosphoric acid solution), o-phenylenediamine (o-PD), 2,4-dinitrophenylhydrazones of aldehyde/ketone-DNPH stock standard-13 (acetaldehyde-DNPH, acetone-DNPH, acrolein-DNPH, benzaldehyde-DNPH, 2-butanone-DNPH, n-butyraldehyde-DNPH, crotonaldehyde-DNPH, formaldehyde-DNPH, hexaldehyde-DNPH, methacrolein-DNPH, propionaldehyde-DNPH, m-tolu aldehyde-DNPH, valeraldehyde-DNPH), methylglyoxal (40% aqueous solution), glyoxal (40% aqueous solution) and pure polyphenol standard, gallic acid, hydroxytyrosol, and epigallocatechin gallate were obtained from Sigma-Aldrich (St. Louis, MO). Trizma base (Tris-(hydroxymethyl)-aminomethane ACS Reagent Grade), solvents for chromatography analysis, such as acetonitrile, methanol, and water, (liquid chromatography-mass spectrometry, LC-MS grade), as well as acetic acid were purchased from Fisher Scientific (Loughborough, UK).

[0038] Disodium hydrogen phosphate and sodium dihydrogen phosphate were purchased from Merck (Darmstadt, Germany). Fibrous four ?m silica (silica wool) was obtained from H. Baumbach & Co Ltd (Suffolk, UK), and Whatman 47 mm QMA silica filters were obtained from Sigma-Aldrich, which were used in the research.

[0039] Then, data were taken gravimetrically weighing propylene glycol, glycerol, and water in a ratio of 70:20:10 (w/w/w), and then the model was used in an e-liquid system which was used as a control sample. In Milli-Q water, epigallocatechin, hydroxytyrosol, and gallic acid were prepared at four different concentrations (0.6; 1.25; 2.5 and 5 mM). Then the e-liquid formulation was vortexed for 1 min, sonicated for 3 min to remove bubbles of air, and stored at 4? C. Laboratory vaping and an aerosol collection were then performed using a Subox Mini C device (KangerTech, Shenzhen, China). High-performance liquid chromatography-Ultraviolet (HLPC-UV) analysis of carbonyl compounds was done according to industry standard methods, followed by HLPC-UV analysis of dicarbonyl compounds. Then Liquid chromatography-tandem mass spectrometry (HPLC-ESI-MS/MS) analysis (Honda et al., 2010) was performed, followed by cell culture and cytotoxicity determination.

[0040] The process of grafting, was carried out in a glass Petri dish having a diameter of 5 cm with a weight of 50 mg and then in an acidic buffer solution of sodium tartrate buffer (4 cm3, 50 mM and pH=4) having content of Tween 80 at 0.05% (w/v), laccase (>80 Units) and catechin (3.5% w/v) for the measurement of activities and 1% w/v for filtration experiments. Samples were developed at 50? C. at 30 rpm for four h in the dark condition. Then the controlled samples of cellulose were treated under similar conditions without the presence of laccase and polyphenol as their contents were followed by washing of cellulose wipes in distilled water for 2 hours with shaking the contents at 30 rpm, and they have air-dried overnight in a room temperature (Fillat et al., 2012).

[0041] The system as per is further embodiments will discuss Sample Preparation. The sample was prepared using commercial cigarette filters. Two filters were used for the experiment:

Polyphenol Treated Filter (PT):

[0042] The filter was removed from the commercial cigarette and treated with 500 ?L of olive polyphenol solution, titrated to hydroxytyrosol.

Filter Negative Control (NC):

[0043] The filter of the commercial cigarette was not treated.

[0044] The filters were placed inside a vacuum system, which was connected to an aerosol nebulizer device. The smoke leaving the PT and NC filters was then analyzed using the Secondary Electrospray (SESI) technique, which allows the identification and quantification of volatile organic compounds in the smoke and aerosol.

[0045] The results of the smoke analysis were used to evaluate the effects of functionalized olive polyphenols on commercial cigarette filters and to determine any differences in the composition of smoke and aerosol released from PT and NC filters.

[0046] The SESI technique was used by setting the aspiration value at 1.2 L/min. The capillary voltage was set at 3 kV. The nebulizer gas value was 5 L/min, and the curtain gas was 1.2 L/min. The solution used to produce the spray was H2O/CH3OH (water/methanol)+0.1% formic acid. The syringe flow rate was 1 ?L/min. Data processing was performed using the SANIST-ORBIT platform.

[0047] Table 1 shows the most significant molecules in which there was a diminution of the signal acquired from smoke and aerosols in the PT filter compared with the NC filter.

[0048] It is contemplated that equivalents and substitutions for certain elements set forth above may be evident to those skilled in the art, and therefore the true scope and definition of the invention is to be as outlined in the following claims.

[0049] While a specific embodiment has been shown and described, many variations are possible. With time, additional features may be employed. The particular shape or configuration of the platform or the interior configuration may be changed to suit the system or equipment with which it is used.

[0050] Having described the invention in detail, those skilled in the art will appreciate that modifications may be made to the invention without departing from its spirit. Therefore, it is not intended that the scope of the invention be limited to the specific embodiment illustrated and described. Instead, it is intended that the appended claims and their equivalents determine the content of this invention.

[0051] The Abstract of the Disclosure is provided to allow the reader to ascertain the technical disclosure's nature quickly. It is submitted with the understanding that it will not be used to interpret or limit the scope or meaning of the claims. In addition, in the foregoing Detailed Description, it can be seen that various features are grouped in various embodiments to streamline the disclosure. This method of disclosure is not to be interpreted as reflecting an intention that the claimed embodiments require more features than are expressly recited in each claim. Instead, as the following claims reflect, the inventive subject matter is less than all features of a disclosed embodiment. Thus, the following claims are incorporated into the Detailed Description, with each claim standing on its own as a separately claimed subject matter.

INDUSTRIAL APPLICATION

[0052] The industrial utility of the invention is in cigarette filter manufacturing. The technology proposed herein encompasses a universal filter, enhanced with olive tree polyphenols, specifically designed to entrap toxic compounds such as amines and nitrosamines found in cigarette smoke. This innovative approach offers a novel mechanism to render cigarette smoking less harmful, by significantly reducing the smoker's exposure to these hazardous substances. Potential adopters of this technology could include tobacco manufacturers seeking to improve the safety profile of their products, and manufacturers of smoking accessories interested in providing healthier alternatives to conventional cigarette filters.