EP1041899B1 - Utilisation de composes polyphenoliques ou de leurs derives comme capteurs de radicaux libres dans les filtres de cigarette - Google Patents

Utilisation de composes polyphenoliques ou de leurs derives comme capteurs de radicaux libres dans les filtres de cigarette Download PDF

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Publication number
EP1041899B1
EP1041899B1 EP98963627A EP98963627A EP1041899B1 EP 1041899 B1 EP1041899 B1 EP 1041899B1 EP 98963627 A EP98963627 A EP 98963627A EP 98963627 A EP98963627 A EP 98963627A EP 1041899 B1 EP1041899 B1 EP 1041899B1
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EP
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Prior art keywords
cigarette
extract
derivatives
filter
polyphenol compounds
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.)
Expired - Lifetime
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EP98963627A
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German (de)
English (en)
French (fr)
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EP1041899A1 (fr
Inventor
Imam Emami
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Biosynthec
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Biosynthec
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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/14—Use of materials for tobacco smoke filters of organic materials as additive

Definitions

  • the present invention relates to the use of compounds polyphenolics or their derivatives as free radical scavengers in cigarette filters.
  • polyphenolic compounds are known for their beneficial properties in areas as varied as hypertension, hypercholesterolemia, involved in cardiovascular disease, viral infections, or inflammatory phenomena. Activities anti-lipoperoxidants and anti-carcinogens of certain polyphenols have also been described.
  • the present invention therefore relates to the use of compounds polyphenolics as scavengers of free radicals in cigarette filters, as defined in claim 1.
  • derivatives in particular the compounds deriving from polyphenolic compounds by substitution of the hydrogen atom of at least one of the hydroxy groups of the polyphenolic compounds by a C 1 -C 6 alkyl group, or a group (alkyl C 1 -C 4 ) carbonyl.
  • Acetates such as acetates of carnosic acid and acetates of rosmarinic acid are preferred derivatives of the polyphenolic compounds used in accordance with the invention.
  • These compounds can be obtained by chemical synthesis conventional or biotechnologically, according to known methods of the skilled person. They can also be isolated from plant extracts.
  • Said polyphenols can also be used according to the present invention in the form of an extract of rosemary ( Rosmarinus officinalis L.).
  • Such a plant extract can be obtained by extraction with a polar solvent such as an alcoholic or hydro-alcoholic solvent.
  • Alcohol used as solvent may in particular be ethanol.
  • This extract can also be advantageously obtained using supercritical carbon dioxide and is then richer in polyphenolic compounds.
  • the plant extract used according to the invention can be obtained by extraction with a polar solvent followed by an extraction with supercritical CO 2 .
  • Rosemary extraction is preferably carried out on plants dried, for example on rosemary branches, cut and dried in sun for 4 to 5 days.
  • Polyphenolic compounds or their derivatives obtained by chemical synthesis, by biotechnology, or by extraction from plants, can be used alone or as a mixture in accordance with the invention.
  • a mixture of carnosol, acid carnosic and rosmarinic acid can be advantageously used.
  • Polyphenolic compounds or their derivatives can be used in free form or can be conjugated or coupled to a support ("carrier") allowing the weight of the polyphenol-support assembly to be increased.
  • Microbeads can in particular serve as a support. They can for example be made of plastic (polystyrene or other) or of glass.
  • Polyphenolic compounds can be incorporated into cigarette filters at a rate of 0.5 mg to 0.5 gram, preferably 0.002 to 0.1 gram, preferably 0.01 gram.
  • the filter of the cigarette can be soaked with an extract alcoholic or hydro-alcoholic plant then subjected to evaporation of the alcoholic or hydro-alcoholic solvent.
  • Polyphenolic compounds or their derivatives can be also dissolved in saturated oil, and thus incorporated into the filter cigarette.
  • the subject of the invention is also a method of preparation a cigarette filter according to claim 9.
  • the invention also relates to a cigarette filter obtained by the above process.
  • a filter makes it possible to reduce the quantity of molecules to free radicals present in cigarette smoke.
  • cytotoxic molecules promote the appearance of cancers in smokers, especially lung cancer.
  • Polyphenols or their derivatives incorporated into the filter of a cigarettes also exhibit, on the one hand, an inhibition of the activity of carcinogenic compounds, by reducing the formation of amines heterocyclic, during the combustion of tobacco and, on the other hand, a detoxification of carcinogenic compounds, such as benzopyrene.
  • the attached figure is a graph representing the intensity of the signal, in electron paramagnetic resonance, of the terbutyloxy radicals in the gas phase of cigarette smoke depending on the amount rosemary extract incorporated into the filter.
  • Rosemary ( Rosmarinus officinalis L.) ears are extracted with ethanol at 65 ° C.
  • the volume of ethanol used corresponds to five times the weight in kg of rosemary ears.
  • the extract is then purified and enriched in polyphenols by selective extraction with supercritical CO 2 .
  • the extract is purified and enriched selectively in its various components.
  • an extract comprising about 25% rosmarinic acid, about 10% camosic acid and about 5% carnosol.
  • a cigarette filter is soaked with either the prepared extract, the ethanol then being evaporated, i.e. an oily phase based on CRODAMOL® (French for Aromas and Perfumes), in which a powder obtained by drying the extract prepared above.
  • CRODAMOL® Frnch for Aromas and Perfumes
  • the effectiveness of the cigarette filter thus prepared is put in evidence first by computer-assisted modeling, according to the Monte-Carlo method, which allows to calculate the number of meetings between a carcinogenic target molecule and a compound polyphenolic used in accordance with the invention.
  • the number of free radical cytotoxic molecules present in cigarette smoke was calculated on either side of the filter.
  • the number of cytotoxic molecules depends on the volume of smoke passing through the filter, the volume of the filter, the concentration of cytotoxic molecules in smoke and polyphenol concentration in the filter.
  • EPR is a technique for studying paramagnetic substances directly or indirectly.
  • Paramagnetic compounds are molecules with a single unpaired electron on their last valence layer. Such substances are designated by the term radicals.
  • radicals When these radicals have very short lifetimes (much less than a second) it is advantageous to use the so-called "spin trapping" technique. It consists in using trappers capable of stabilizing the radicals produced by the formation of an adduct and thus of measuring them for several minutes. This reaction is done as follows:
  • DMPO 5.5 'dimethyl pyrroline-N-oxide
  • a cigarette is placed at the end of such a device, and the gas phase of the smoke, after passing through a Cambridge filter (thinner than a cigarette filter to retain tar), is dissolved in a benzene "spin trap" solution.
  • the DMPO is adjusted to a concentration of 32 mM in a benzene solution and the gas phase of two cigarettes is used.
  • the radical mainly present in these tars and responsible for a well-established carcinogenic activity to date, is of a nature semiquinone. This semiquinone which has a long lifespan will be able react within cells and thus produce deleterious species such as oxygen radicals.
  • the decrease in signal indicates that the rosemary extract has a speed of trapping of radicals higher than that of DMPO (see figure).
  • the filter was impregnated with 250 ⁇ l of the lipid-based phase CRODAMOL®, containing 10 mg / ml dry rosemary extract powder.
EP98963627A 1997-12-24 1998-12-23 Utilisation de composes polyphenoliques ou de leurs derives comme capteurs de radicaux libres dans les filtres de cigarette Expired - Lifetime EP1041899B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9716522A FR2772561B1 (fr) 1997-12-24 1997-12-24 Utilisation de composes polyphenoliques ou de leurs derives comme capteurs de radicaux libres dans les filtres de cigarette
FR9716522 1997-12-24
PCT/FR1998/002868 WO1999033365A1 (fr) 1997-12-24 1998-12-23 Utilisation de composes polyphenoliques ou de leurs derives comme capteurs de radicaux libres dans les filtres de cigarette

Publications (2)

Publication Number Publication Date
EP1041899A1 EP1041899A1 (fr) 2000-10-11
EP1041899B1 true EP1041899B1 (fr) 2002-08-28

Family

ID=9515146

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Application Number Title Priority Date Filing Date
EP98963627A Expired - Lifetime EP1041899B1 (fr) 1997-12-24 1998-12-23 Utilisation de composes polyphenoliques ou de leurs derives comme capteurs de radicaux libres dans les filtres de cigarette

Country Status (14)

Country Link
US (2) US20060213533A1 (pt)
EP (1) EP1041899B1 (pt)
JP (1) JP4763126B2 (pt)
KR (1) KR100890583B1 (pt)
CN (1) CN1177546C (pt)
AT (1) ATE222714T1 (pt)
AU (1) AU1883299A (pt)
BR (1) BR9814488B1 (pt)
CA (1) CA2316988C (pt)
DE (1) DE69807525D1 (pt)
FR (1) FR2772561B1 (pt)
IL (1) IL136973A0 (pt)
NO (1) NO311702B1 (pt)
WO (1) WO1999033365A1 (pt)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3122994A1 (fr) 2021-05-24 2022-11-25 Iman Emami Formulation de microparticules a base de composes polyphenoliques capables de pieger les radicaux libres presents dans l’air pollue et les fumees

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1222865A4 (en) 1999-10-20 2005-01-12 Daicel Chem CIGARETTE INGREDIENT AND METHOD OF MANUFACTURE
ITMI20012756A1 (it) * 2001-12-21 2003-06-21 Filtrona Italia S P A Filtri per sigarette contenenti flavonoidi lipofili e/o tocoferoli e tocotrienoli
RU2304914C2 (ru) 2003-04-10 2007-08-27 Джапан Тобакко Инк. Сигаретный фильтр
KR20130103834A (ko) * 2006-11-17 2013-09-24 비오신테크 로즈마리 추출물을 포함하는 담배 필터 및 상기 필터를 사용하여 담배 연기 내의 유해 물질에 의해 유발되는 ｄｎａ 손상을 감소시키는 방법
CN103110188A (zh) * 2006-11-17 2013-05-22 生物合成技术公司 含有迷迭香提取物的卷烟过滤嘴以及通过使用所述过滤嘴减少由烟雾中有害物质引起的dna 损伤的方法
EP2088877B1 (en) * 2006-11-29 2018-08-01 Imperial Tobacco Canada Limited Cigarette filter with flavored particles
JP5766934B2 (ja) 2010-11-01 2015-08-19 株式会社ダイセル タバコフィルター及びその製造方法並びにタバコ
JP2013150619A (ja) * 2013-03-06 2013-08-08 Bio Synthec ローズマリー抽出物を含有したたばこフィルター及び当該フィルターを使用することによりたばこの煙に含まれる有害物に起因したｄｎａ損傷を低減する方法
CN105167191B (zh) * 2015-06-17 2019-01-11 湖北中烟工业有限责任公司 烟用黄酮类化合物香精烟珠及其制备方法
US10226066B2 (en) 2016-03-07 2019-03-12 R.J. Reynolds Tobacco Company Rosemary in a tobacco blend
CN108338406B (zh) * 2018-02-13 2020-07-28 玉溪开元金蓝生物科技有限责任公司 一种迷迭香抗氧化剂爆珠及其在卷烟滤棒中的应用
CN109022152A (zh) * 2018-08-30 2018-12-18 湖北中烟工业有限责任公司 一种迷迭香烟用香料及其制备方法和应用
KR102436227B1 (ko) * 2020-05-29 2022-08-24 주식회사 케이티앤지 기능성 물질이 코팅된 흡연물품용 팁페이퍼 및 상기 팁페이퍼의 코팅 방법
CN111789284A (zh) * 2020-07-08 2020-10-20 福建中烟工业有限责任公司 一种烟用丝束及其制备方法和应用

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2564296A1 (fr) * 1984-05-16 1985-11-22 Grenet Edouard Filtre pour cigarettes
US4800903A (en) * 1985-05-24 1989-01-31 Ray Jon P Nicotine dispenser with polymeric reservoir of nicotine
US4738857A (en) * 1986-07-25 1988-04-19 Heublein, Inc. Shelf stable plastic packaged alcoholic beverage containing essential oils
KR890003612A (ko) * 1987-08-08 1989-04-15 프랑코 사보이아 비원형 지지체에의 필름 권취장치
CH672048A5 (pt) * 1987-09-16 1989-10-31 Nestle Sa
KR890003612B1 (ko) * 1988-02-27 1989-09-28 한국전매공사 권련 제조방법
US4930983A (en) 1988-09-26 1990-06-05 United Technologies Corporation Hybrid helicopter rotor hub retention plate
JP2713449B2 (ja) 1988-12-13 1998-02-16 日本テルペン化学株式会社 ビフェニル化合物類ならびにその抗酸化組成物および消臭組成物
JP2766547B2 (ja) * 1990-08-08 1998-06-18 シャープ株式会社 水平同期信号分離回路
JPH05115273A (ja) * 1991-09-10 1993-05-14 Uenoya Bikouen:Kk たばこ
US5308874A (en) * 1992-06-26 1994-05-03 Vyrex Corporation Airborne protectants against oxidative tissue damage
JPH0662824A (ja) * 1992-08-12 1994-03-08 Kyodo Nyugyo Kk タバコ煙からのフリ−ラジカルの除去法
AU675573B2 (en) * 1993-09-30 1997-02-06 British-American Tobacco Company Limited Improvements relating to tobacco smoke filter elements
JPH07196645A (ja) 1993-12-28 1995-08-01 Yokohama Yushi Kogyo Kk ポリフェノール類の抽出方法及び該方法により得られる抽出液と抽出物
LU88544A1 (fr) * 1994-10-07 1996-04-29 G L A D S A Traitement anticarcinogène pour filtres de cigarettes ou autres du même genre
EP0728420A1 (fr) 1995-02-21 1996-08-28 Societe Des Produits Nestle S.A. Procédé d'extraction d'antioxydants de matière végétale
EP0728421B1 (fr) * 1995-02-21 2002-06-05 Societe Des Produits Nestle S.A. Procédé d'extraction d'antioxydants de matière végétale
CN1073387C (zh) * 1995-09-13 2001-10-24 北京卷烟厂 低自由基低毒卷烟及其生产方法
WO1998032449A1 (es) * 1996-02-22 1998-07-30 Asociacion De Investigacion De La Industria Agroalimentaria Procedimiento para extraer productos naturales mediante fluidos supercriticos
GB9707130D0 (en) * 1997-04-08 1997-05-28 Advanced Phytonics Ltd Solvent extraction
US6855349B2 (en) * 1998-12-07 2005-02-15 Kemin Industries, Inc. Method for simultaneous extraction of essential oils and antioxidants from Labiatae species and the extract products thereof
US6450935B1 (en) * 2000-10-13 2002-09-17 Kemin Industries, Inc. Method for removing essential oils and antioxidants from extract products of lamiaceae species using rolled film evaporation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3122994A1 (fr) 2021-05-24 2022-11-25 Iman Emami Formulation de microparticules a base de composes polyphenoliques capables de pieger les radicaux libres presents dans l’air pollue et les fumees
WO2022248803A1 (fr) 2021-05-24 2022-12-01 Iman Emami Formulation de microparticules a base de composes polyphenoliques capables de pieger les radicaux libres presents dans l'air pollue et les fumees

Also Published As

Publication number Publication date
NO20003324D0 (no) 2000-06-23
CN1177546C (zh) 2004-12-01
BR9814488A (pt) 2001-09-25
JP4763126B2 (ja) 2011-08-31
KR100890583B1 (ko) 2009-03-25
US20060213533A1 (en) 2006-09-28
JP2001526913A (ja) 2001-12-25
FR2772561B1 (fr) 2000-12-29
CN1283966A (zh) 2001-02-14
EP1041899A1 (fr) 2000-10-11
NO20003324L (no) 2000-08-24
CA2316988A1 (fr) 1999-07-08
ATE222714T1 (de) 2002-09-15
FR2772561A1 (fr) 1999-06-25
IL136973A0 (en) 2001-06-14
US20120222691A1 (en) 2012-09-06
BR9814488B1 (pt) 2010-11-30
US8567412B2 (en) 2013-10-29
WO1999033365B1 (fr) 1999-08-19
NO311702B1 (no) 2002-01-14
CA2316988C (fr) 2010-11-16
WO1999033365A1 (fr) 1999-07-08
AU1883299A (en) 1999-07-19
DE69807525D1 (de) 2002-10-02
KR20010033587A (ko) 2001-04-25

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