CA2316249A1 - Use of a phenol oxidising enzyme in the treatment of tobacco - Google Patents
Use of a phenol oxidising enzyme in the treatment of tobacco Download PDFInfo
- Publication number
- CA2316249A1 CA2316249A1 CA002316249A CA2316249A CA2316249A1 CA 2316249 A1 CA2316249 A1 CA 2316249A1 CA 002316249 A CA002316249 A CA 002316249A CA 2316249 A CA2316249 A CA 2316249A CA 2316249 A1 CA2316249 A1 CA 2316249A1
- Authority
- CA
- Canada
- Prior art keywords
- tobacco
- process according
- extract
- enzyme
- treating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/20—Biochemical treatment
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Manufacture Of Tobacco Products (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
A process for preparing tobacco, which process comprises the steps of treating a tobacco material with a phenol oxidising enzyme, such as by extracting tobacco with a solvent to provide an extract and a residue; and treating the extract with a phenol oxidising enzyme such as a laccase. An improved tobacco product having a reduced amount of phenolic compounds. This is an alternative or a supplement to a process in which the phenolic compounds are adsorbed onto the insoluble carrier polyvinylpolypyrrolidone (PVPP). In preferred embodiments, the process includes further steps of removing the oxidised phenolic compound, adding adsorbents such as bentonite; removing and/or inactivating the enzyme; and concentrating the extract. Preferred phenol oxidising enzymes are peroxidases and laccases. The thus treated extract is advantageously re-combined with the tobacco residue and further processed to provide a tobacco article for smoking.
Claims (44)
1. A process for preparing a tobacco product, which process comprises the step of (i) treating a tobacco material with a phenol oxidising enzyme with the proviso that the phenol oxidising enzyme is not monophenol monooxygenase (EC 1.14.18.1).
2. The process according to claim 1, which further comprises the 1o steps of (ii) extracting a tobacco material with a solvent to provide an extraction mixture; and (iii) separating the extraction mixture into a tobacco extract and a tobacco residue, wherein the treatment of step (i) is performed during or after step (ii).
3. A process for preparing a tobacco product, which process comprises the steps of 2o (ii) extracting a tobacco material with a solvent to provide an extraction mixture;
(iii) separating the extraction mixture into a tobacco extract and a tobacco residue, (i) treating the tobacco extract with a phenol oxidising 2s enzyme to produce one or more oxidised phenolic compounds.
(iii) separating the extraction mixture into a tobacco extract and a tobacco residue, (i) treating the tobacco extract with a phenol oxidising 2s enzyme to produce one or more oxidised phenolic compounds.
4. The process according to claim 2 or 3, further comprising the step of (iv) separating the oxidised phenolic compounds) from the tobacco extract.
5. The process according to claim 4, wherein said separation is achieved by means of centrifugation, filtration, ultrafiltration, sedimentation, reverse osmosis, sedimentation, adsorption, decanting or sieving, or any combinations of the foregoing.
6. The process according to any of claims 1-5, further comprising the step of inactivating and/or removing the phenol oxidising enzyme.
7. The process according to any of claims 2-6, further comprising the step of (vi) concentrating the extract.
8. The process according to any of claims 2-7, further comprising:
(vii) treating the extract with an insoluble adsorbent; and/or (viii) treating the extract with polyvinylpolypyrrolidone (PVPP).
(vii) treating the extract with an insoluble adsorbent; and/or (viii) treating the extract with polyvinylpolypyrrolidone (PVPP).
9. The process according to claim 3, which comprises the following steps in the sequence indicated:
(ii) extracting a tobacco material with a solvent to provide an extraction mixture;
(iii) separating the extraction mixture into a tobacco extract and a tobacco residue;
(i) treating the extract with a phenol oxidising enzyme;
(vii) treating the extract with an insoluble adsorbent; and (vi) concentrating the extract.
(ii) extracting a tobacco material with a solvent to provide an extraction mixture;
(iii) separating the extraction mixture into a tobacco extract and a tobacco residue;
(i) treating the extract with a phenol oxidising enzyme;
(vii) treating the extract with an insoluble adsorbent; and (vi) concentrating the extract.
10. The process according to claim 3, which comprises the following steps in the sequence indicated:
(ii) extracting a tobacco material with a solvent to provide an extraction mixture;
(iii) separating the extraction mixture into a tobacco extract and a tobacco residue;
(i) treating the extract with a phenol oxidising enzyme to produce one or more oxidised phenolic compound;
(iv) separating the oxidised phenolic compound(s) from the tobacco extract; and (vi) concentrating the extract.
(ii) extracting a tobacco material with a solvent to provide an extraction mixture;
(iii) separating the extraction mixture into a tobacco extract and a tobacco residue;
(i) treating the extract with a phenol oxidising enzyme to produce one or more oxidised phenolic compound;
(iv) separating the oxidised phenolic compound(s) from the tobacco extract; and (vi) concentrating the extract.
11. The process according to any of claims 2-10, further comprising the step of combining the enzyme-treated tobacco extract with a tobacco material.
12. The process according to any of claims 2-10, further comprising the step of (ix) recombining the enzyme-treated tobacco extract with the tobacco residue.
13. The process according to any of claims 1-12 , further comprising the step of treatment with a proteolytic enzyme.
14. The process according to any of claims 11-13, wherein a tobacco material or a tobacco residue has been treated with a protease before the combination with the extract.
15. The process according to any of claims 1-14, where the tobacco product is a tobacco article for smoking.
16. The process according to any of claims 2-15, wherein the solvent is an aqueous solvent.
17. The process according to claim 16, wherein the solvent comprises a protease.
18. The process according to any of claim 2-17 wherein the solvent comprises a surfactant.
19. The process according to any of claims 1-18, wherein the phenol oxidising enzyme is a phenolic oxidase.
20. The process according to claim 19, wherein the phenolic oxidase is selected from the group consisting of a catechol oxidase, a laccase and an o-aminophenol oxidase.
21. The process according to claim 20, wherein the phenolic oxidase is a laccase, such as e.g. a laccase derived from tobacco.
22. The process according to claim 21, wherein the laccase is derived from Trametes, e.g. Trametes villosa, from Myceliophthora, e.g. Myceliophthora thermophila, from Coprinus, e.g. Coprinus cinereus, from Rhizoctonia, e.g. Rhizoctonia solani, Pycnoporus, e.g. Pycnoporus cinnabarious, or from tobacco species.
23. The process according to any of claims 1-18, wherein the phenol oxidising enzyme is a peroxidase.
24. The process according to claim 23, wherein the peroxidase is a horseradish peroxidase, a soy bean peroxidase, a tobacco peroxidase or a peroxidase derived from Coprinus, e.g., Coprinus cinereus, Coprinus macrorhizus, from Bacillus, e.g., Bacillus pumilus, or from Myxococcus, e.g., Myxococcus virescens.
25. The process according to any of claims 1-24, wherein the phenol oxidising enzyme reacts with its substrate by single electron transfer.
26. The process according to any of claims 1-25 wherein the phenol oxidising enzyme is derived from tobacco.
27. The process according to any of claims 1-26, wherein the phenol oxidising enzyme is not monophenol monooxygenase (EC
1.14.18.1).
1.14.18.1).
28. A process for preparing a tobacco product with a reduced concentration of at least one phenolic compound, which process comprises the step of treating a tobacco material with a phenol oxidising enzyme.
29. A process for preparing a tobacco product comprising the step of treating a tobacco material with a phenol oxidising enzyme to provide a tobacco product with a reduced concentration of a phenolic compound, said reduction is an at least 5%, at least 10%, at least 20%, at least 40%, at least 50%, at least 60%, at least 75, at least 80%, at least 95 %, least 98% or a 100% reduction in the concentration of said phenolic compound in said tobacco material.
30. The process according to claim 29, wherein the phenolic compound is chlorogenic acid.
31. The process according to claim 29, wherein the phenolic compound is rutin.
32. The process according to claim 29, wherein the phenolic compound is scopoletin.
33. A process for preparing a tobacco product comprising the step of treating a tobacco material with a phenol oxidising enzyme to provide a tobacco product which by HPLC analysis shows a reduction in a signal (peaks) compared to the tobacco material from before the enzyme treatment step, said signal corresponding to a phenolic compound, where said reduction is an at least 5%, at least 10%, at least 20%, at least 40%, at least 50%, at least 60%, at least 75, at least 80%, at least 95 %, least 98% or 100%
reduction.
reduction.
34. The process according to any of claims 28-33 which process comprises one or more of the steps as defined in claims 1-27.
35. The process according to any of claims 28-33 wherein the tobacco material is a tobacco extract.
36. A process for reducing the concentration of at least one phenolic compound in a tobacco material comprising treating an extract of a tobacco material with a phenol oxidising enzyme.
37. A process for reducing the concentration of at least one phenolic compound in a tobacco material according to any of claims 1-36 wherein said phenolic compound(s) is/are low molecular weight phenolic compound(s).
38. A process for reducing the concentration of at least one phenolic compound in a tobacco material comprising treating an extract of a tobacco material with a phenol modifying enzyme.
39. Use of a phenol oxidising enzyme in the processing of a tobacco extract.
40. Use of a phenol oxidising enzyme in the preparation of a tobacco product, said phenol oxidising enzyme is not monophenol monooxygenase (EC 1.14.18.1).
41. Use of a laccase in the preparation of a tobacco product.
42. Use of a laccase and a protease in the preparation of a tobacco product.
43. A tobacco material obtainable by any of the processes of claims 1-38.
44. A modified tobacco product having a reduced concentration of at least one phenolic compound relative to a tobacco material from which it is derived, wherein said product is produced by treating a tobacco material with a phenol oxidizing enzyme.
44. A modified tobacco product according to claim 44 wherein the product is produced by a process which further comprises one or more of the steps as defined in claims 1-27.
44. A modified tobacco product according to claim 44 wherein the product is produced by a process which further comprises one or more of the steps as defined in claims 1-27.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA199800905 | 1998-07-08 | ||
| DKPA199800905 | 1998-07-08 | ||
| PCT/DK1999/000389 WO2000002464A1 (en) | 1998-07-08 | 1999-07-07 | Use of a phenol oxidising enzyme in the treatment of tobacco |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2316249A1 true CA2316249A1 (en) | 2000-01-20 |
| CA2316249C CA2316249C (en) | 2012-11-27 |
Family
ID=8098853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2316249A Expired - Fee Related CA2316249C (en) | 1998-07-08 | 1999-07-07 | Use of a phenol oxidising enzyme in the treatment of tobacco |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1094724B1 (en) |
| JP (3) | JP2002520005A (en) |
| AT (1) | ATE225612T1 (en) |
| AU (1) | AU761885B2 (en) |
| BR (1) | BR9911909B1 (en) |
| CA (1) | CA2316249C (en) |
| DE (1) | DE69903430T2 (en) |
| WO (1) | WO2000002464A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11039639B2 (en) | 2014-02-26 | 2021-06-22 | Japan Tobacco Inc. | Producing method of tobacco raw material |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1825766A1 (en) * | 2004-10-27 | 2007-08-29 | Japan Tobacco, Inc. | Tobacco material having its stimulation/hot flavor at smoking reduced, smoking flavor imparting agent, regenerated tobacco material, process for producing tobacco material, and process for producing smoking flavor imparting agent |
| MY142519A (en) * | 2006-04-25 | 2010-12-15 | Japan Tobacco Inc | Shredded tobacco and method of treating tobacco |
| GB0810850D0 (en) * | 2008-06-13 | 2008-07-23 | British American Tobacco Co | Tobacco treatment |
| US8360072B2 (en) * | 2009-10-09 | 2013-01-29 | Philip Morris Usa Inc. | Combination treatment of tobacco extract using antioxidants and antioxidant scavengers |
| US9402415B2 (en) * | 2010-04-21 | 2016-08-02 | R. J. Reynolds Tobacco Company | Tobacco seed-derived components and materials |
| GB201108860D0 (en) | 2011-05-26 | 2011-07-06 | British American Tobacco Co | Tobacco treatment |
| US9420825B2 (en) * | 2012-02-13 | 2016-08-23 | R.J. Reynolds Tobacco Company | Whitened tobacco composition |
| US9485953B2 (en) | 2012-07-19 | 2016-11-08 | R.J. Reynolds Tobacco Company | Method for treating tobacco plants with enzymes |
| GB201213870D0 (en) * | 2012-08-03 | 2012-09-19 | British American Tobacco Co | Tobacco extract, preparation thereof |
| GB201221210D0 (en) * | 2012-11-26 | 2013-01-09 | British American Tobacco Co | Treatment of tobacco material |
| GB201221199D0 (en) * | 2012-11-26 | 2013-01-09 | British American Tobacco Co | Treatment of tobacco material |
| US9980509B2 (en) | 2013-04-05 | 2018-05-29 | R.J. Reynolds Tobacco Company | Modification of bacterial profile of tobacco |
| US9155334B2 (en) | 2013-04-05 | 2015-10-13 | R.J. Reynolds Tobacco Company | Modification of bacterial profile of tobacco |
| EP2989907A4 (en) * | 2013-08-27 | 2017-01-11 | Japan Tobacco, Inc. | Tobacco raw material, method for manufacturing same, and tobacco product |
| CN106028844B (en) | 2014-02-26 | 2018-03-09 | 日本烟草产业株式会社 | The manufacture method of the extracting method of fragranced composition and the inscape of preference |
| CA2940690C (en) * | 2014-02-26 | 2019-01-22 | Japan Tobacco Inc. | Extraction method of flavor constituent and manufacturing method of composition element of favorite item |
| WO2016063775A1 (en) * | 2014-10-24 | 2016-04-28 | 日本たばこ産業株式会社 | Method for producing cigarette ingredient |
| CN103932378B (en) * | 2014-04-29 | 2016-02-24 | 湖北中烟工业有限责任公司 | The detection method of slag-containing rate in papermaking-method reconstituted tobaccos tobacco material extract |
| JP6533582B2 (en) | 2014-10-02 | 2019-06-19 | ディジレッツ， インコーポレイテッド | Disposable tank type electronic cigarette, manufacturing method and use method |
| EP3210630A1 (en) | 2016-02-29 | 2017-08-30 | G.L. Pharma GmbH | Abuse-deterrent pharmaceutical compositions |
| EP3231420A1 (en) | 2016-02-29 | 2017-10-18 | G.L. Pharma GmbH | Abuse-deterrent pharmaceutical compositions |
| EP3210596A1 (en) | 2016-02-29 | 2017-08-30 | G.L. Pharma GmbH | Abuse-deterrent pharmaceutical composition |
| US10813383B2 (en) | 2016-12-12 | 2020-10-27 | R.J. Reynolds Tobacco Company | Dehydration of tobacco and tobacco-derived materials |
| WO2019026201A1 (en) * | 2017-08-02 | 2019-02-07 | 日本たばこ産業株式会社 | Method for producing tobacco flavor liquid, and tobacco flavor liquid |
| US11278050B2 (en) | 2017-10-20 | 2022-03-22 | R.J. Reynolds Tobacco Company | Methods for treating tobacco and tobacco-derived materials to reduce nitrosamines |
| JP7054708B2 (en) | 2017-12-27 | 2022-04-14 | 日本たばこ産業株式会社 | Tobacco extract, method for producing tobacco extract, and non-combustible flavor aspirator using tobacco extract |
| JP7021755B2 (en) * | 2018-08-10 | 2022-02-17 | 日本たばこ産業株式会社 | Sample evaluation / estimation methods, programs, and equipment by fluorescent fingerprint analysis |
| WO2020031448A1 (en) * | 2018-08-10 | 2020-02-13 | 日本たばこ産業株式会社 | Method for creating reference for determining classification of plant-derived material containing chlorophyll and at least one of polyphenols and terpenoids, program, and device |
| CN112120266B (en) * | 2020-08-26 | 2022-01-21 | 江西中烟工业有限责任公司 | Processing method of three-class or four-class cigarette leaf group formula |
| CN112120265B (en) * | 2020-08-26 | 2022-01-21 | 江西中烟工业有限责任公司 | Processing method of leaf group formula containing aged tobacco leaves |
| EP4265128A1 (en) | 2020-12-21 | 2023-10-25 | Japan Tobacco Inc. | Tobacco-component-concentrated liquid, method for manufacturing same, flavor-producing article, and method for manufacturing same |
| CN115606830A (en) * | 2022-08-17 | 2023-01-17 | 中国烟草总公司郑州烟草研究院 | Tobacco odor type regulating agent and application thereof in regulating tobacco odor type |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3599645A (en) * | 1969-03-18 | 1971-08-17 | Research Corp | Treatment of tobacco to reduce polyphenol content |
| JPS5070500A (en) * | 1973-10-23 | 1975-06-11 | Nippon Oil Co Ltd | |
| JPS5231959B2 (en) * | 1973-10-27 | 1977-08-18 | ||
| US4347324A (en) * | 1979-09-24 | 1982-08-31 | Leaf Proteins, Inc. | Process for isolation of proteins from plant leaves |
| GB2069814A (en) * | 1980-02-27 | 1981-09-03 | Inst Przemyslu Fermentacyjnego | Microbiological treatment of tobacco and forming reconstituted tobacco or substitute |
| JPS6045908B2 (en) * | 1982-12-09 | 1985-10-12 | 日本たばこ産業株式会社 | Method for modifying tobacco raw materials |
| US4941484A (en) * | 1989-05-30 | 1990-07-17 | R. J. Reynolds Tobacco Company | Tobacco processing |
| JPH04126037A (en) * | 1990-09-14 | 1992-04-27 | Lotte Co Ltd | Improvement in flavor of cacao nib and processed product thereof by enzymatic treatment |
| US5311886A (en) * | 1991-12-31 | 1994-05-17 | Imasco Limited | Tobacco extract treatment with insoluble adsorbent |
| JPH09206071A (en) * | 1996-01-29 | 1997-08-12 | Novo Nordisk As | Oxidase originated from bacteria |
| JP3320307B2 (en) * | 1996-06-06 | 2002-09-03 | 株式会社エス・ディー・エス バイオテック | Method for polymerizing phenolic compounds and its use |
-
1999
- 1999-07-07 AU AU47698/99A patent/AU761885B2/en not_active Ceased
- 1999-07-07 AT AT99931028T patent/ATE225612T1/en not_active IP Right Cessation
- 1999-07-07 JP JP2000558734A patent/JP2002520005A/en not_active Withdrawn
- 1999-07-07 DE DE69903430T patent/DE69903430T2/en not_active Expired - Lifetime
- 1999-07-07 EP EP99931028A patent/EP1094724B1/en not_active Expired - Lifetime
- 1999-07-07 BR BRPI9911909-9A patent/BR9911909B1/en not_active IP Right Cessation
- 1999-07-07 CA CA2316249A patent/CA2316249C/en not_active Expired - Fee Related
- 1999-07-07 WO PCT/DK1999/000389 patent/WO2000002464A1/en active IP Right Grant
-
2010
- 2010-07-30 JP JP2010172149A patent/JP2011010656A/en not_active Withdrawn
-
2013
- 2013-12-27 JP JP2013272447A patent/JP2014057603A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11039639B2 (en) | 2014-02-26 | 2021-06-22 | Japan Tobacco Inc. | Producing method of tobacco raw material |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1094724B1 (en) | 2002-10-09 |
| JP2002520005A (en) | 2002-07-09 |
| EP1094724A1 (en) | 2001-05-02 |
| DE69903430T2 (en) | 2003-06-05 |
| BR9911909A (en) | 2001-03-27 |
| JP2011010656A (en) | 2011-01-20 |
| BR9911909B1 (en) | 2009-01-13 |
| AU4769899A (en) | 2000-02-01 |
| WO2000002464A1 (en) | 2000-01-20 |
| AU761885B2 (en) | 2003-06-12 |
| DE69903430D1 (en) | 2002-11-14 |
| ATE225612T1 (en) | 2002-10-15 |
| CA2316249C (en) | 2012-11-27 |
| JP2014057603A (en) | 2014-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160707 |