Drug – bio-affecting and body treating compositions – Plant material or plant extract of undetermined constitution... – Containing or obtained from compositeae
Reexamination Certificate
2001-03-13
2002-11-12
Tate, Christopher R. (Department: 1651)
Drug, bio-affecting and body treating compositions
Plant material or plant extract of undetermined constitution...
Containing or obtained from compositeae
Reexamination Certificate
active
06479080
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a
Tanacetum parthenium
extract substantially free of &agr;-unsaturated &ggr;-lactones. The invention addition preparation of the extract and to pharmaceutical and cosmetic compositions containing a
Tanacetum parthenium
extract which is substantially free of parthenolide.
BACKGROUND OF THE INVENTION
Extracts of
Tanacetum parthenium
, a plant belonging to the family Asteracee/Composite, also known as Altamisa, Crisanthemum, Leucanthemum,
Pyrethrum parthenium
as well as under the common name “feverfew”, have traditionally been used in the treatment of migraine, vertigo, arthritis, menstrual disorders, fever, toothache, stomach ache and insect bites. Extracts of
Tanacetum parthenium
contain various volatile oils having mono- and/or sesquiterpene components, flavonoids, tannins, and pyrethrin, as well as terpenoids of the family of sesquiterpene lactones, known as germacranolides, guaianolides, and eudesmanolides. These latter compounds are characterized by an &agr;-unsaturated &ggr;-lactone structure and contain in particular the compounds known as parthenolide, 3-&bgr;-hydroxy-parthenoide, costunolide, 3-&bgr;-hydroxy-costunolide, artemorin, 8-&agr;-hydroxy-estafiatin and chrysanthemonin. The presence of these sesquiterpene lactones is considered necessary for the extracts to achieve pharmacological activity (
J. Pharm. Pharmacol
., 1992, 44:391-5).
Particular attention has been focused on parthenolide, which is thought to be the fundamental active ingredient of these extracts, but which is also responsible for allergic reactions which can sometimes occur following treatment with the extracts of
Tanacetum parthenium
(see, for example,
Arch. Dermatol. Forsch
., 1975, 251(3):235-44
; Arch. Dermatol. Forsch
., 1976, 255(2):111-21
; Contact Dermatitis
, 1988,38(4):207-8
; Am. J Contact Dermatol
., 1998-9 (1):49-50
; Br. J Dermatol
., 1995, 132(4):543-7). Extracts of
Tanacetum parthenium
containing parthenolide are disclosed in International Publication Nos. WO 92/11857, WO 94/06800, and WO 98/39018, European Patent Nos. EP 0 553 658 and EP 0 098 041, and British Patent No. GB 2,166,952.
SUMMARY OF THE INVENTION
In a first embodiment the invention is directed to a
Tanacetum parthenium
extract which is substantially free of &agr;-unsaturated &ggr;-lactones. In a preferred embodiment, the content of &agr;-unsaturated &ggr;-lactones is below 0.2 wt %. More preferably, the &agr;-unsaturated &ggr;-lactones are present in an amount of no more than 0.1 wt %.
In a further embodiment the extract is substantially free of parthenolide. Preferably the parthenolide content is below 0.2 wt %, and more preferably below 0. I wt %.
In another embodiment, the invention is directed to a
Tanacetum parthenium
extract which is obtainable by a process comprising the steps of:
(a) extracting a quantity of plant material from an aerial portion of
Tanacetum parthenium
with a solvent selected from the group consisting of acetone, an alcohol and mixtures of acetone or an alcohol with water, to form a first extract;
(b) extracting the first extract with a hydrocarbon solvent to produce a second extract having a hydrocarbon phase and a non-hydrocarbon phase;
(c) evaporating the hydrocarbon phase from the second extract to form a first residue;
(d) extracting the non-hydrocarbon phase with a non-polar solvent to form a third extract;
(e) evaporating the non-polar solvent portion of the third extract to produce a second residue and redissolving the second residue in a water-alcoholic solution of acid;
(f) adding to the water-alcoholic solution a quantity of a strongly basic resin;
(g) eluting the resin with an alcohol solution and separating the eluate from the resin;
(h) treating the resin with an alcoholic or water-alcoholic solution of an acid;
(i) concentrating the alcoholic or water-alcoholic solution to form a third residue;
(j) extracting the third residue with a non-polar solvent to produce a fourth extract;
(k) evaporating the non-polar solvent from step (j) to form a fourth residue;
(1) combining the first and the fourth residues with the third extract to form a mixture;
(m) evaporating a liquid portion of the mixture to form a fifth residue; and
(n) at least partially drying the fifth residue.
Still further, the invention is directed to a pharmaceutical composition containing an extract as described herein in admixture with a pharmaceutically acceptable carrier.
The invention is additionally directed to a process for forming an extract of
Tanacetum parthenium
substantially free of &agr;-unsaturated &ggr;-lactone which includes the method steps set forth above.
REFERENCES:
patent: 4758433 (1988-07-01), Johnson et al.
patent: 5384121 (1995-01-01), Rhodes
patent: 5466451 (1995-11-01), Beuscher et al.
patent: 9348241 (1994-04-01), None
Hepinstall et al., “Feverfew: A Review of its History, its Biological and Medicinal Properties, and the Status of Commercial Preparations of the Herb” inPhytomedicines of Europe,ACS Symposium Series vol. 691, 1998, 158-75.
Dornelles et al.,Rev. Bras. Farm.,1998, 79(1/2), 42-4.
Lamminpaa et al.,Contact Dermatitis,1996, 34(5), 330-5.
Weerdt et al.,Phytomedicine,1996, 3(3), 225-30.
Williams et al.,Phytochemistry,38(1), 267-70, 1995.
Barsby et al.,Planta Med.,1993, 59, 20-5.
Sumner et al.,Biochem. Pharmacol.,1992, 43(11), 2313-20.
Hausen et al.,Acta Derm.-Venereol.,1983, 63(4). 308-14.
Hausen, B.M.,Dermatosen in Beruf und Unwelt,1981, 29(1), 18-21 (English Abstract).
Bombardelli Ezio
Morazzoni Paolo
Indena S.p.A.
Pennie & Edmonds LLP
Tate Christopher R.
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