Products extracted from a plant of the genus Commiphora,...

Details Products extracted from a plant of the genus Commiphora,... Products extracted from a plant of the genus Commiphora,...

1999-07-14

2003-10-07

Hartley, Michael G. (Department: 1616)

Drug, bio-affecting and body treating compositions

Plant material or plant extract of undetermined constitution...

Containing or obtained from commiphora

C514S549000, C514S844000, C514S847000

Reexamination Certificate

active

06630177

ABSTRACT:

The invention relates to the use in cosmetics of extracts of a plant of the genus Commiphora, particularly the plant
Commiphora mukul
, especially as an agent with antiwrinkle activity. It further relates, by way of novel industrial products, to two particularly active products isolated from these extracts, and to derivatives of these novel products.
It is known that the plant
Commiphora mukul
belongs to the family of the Burseraceae.
Commiphora mukul
is a plant of Indian origin which is very widely used in traditional Indian medicine and in ayurvedic medicine. A resin produced by
Commiphora mukul
, which is also called guggul, is used in particular in these applications. This ayurvedic treatment was known to comprise the treatment of obesity and lipidic disorders, as well as rheumatic diseases.
It should be noted that the term “guggul” denotes both the plant and the resin it produces. Also, this plant is a small tree or a shrub of 1.2 to 1.8 m in height, which grows essentially in India, and the gum resin can be harvested in the ordinary way by making an incision in the plant.
Patents U.S. Pat. No. 4,847,071, U.S. Pat. No. 4,847,069, U.S. Pat. No. 4,946,671 and U.S. Pat. No. 4,954,332 have recently described topical compositions, containing free radical absorbers and an anti-inflammatory agent, for protecting against UV radiation. Guggal or guggul extract is among the numerous anti-inflammatory agents mentioned.
Furthermore, document EP-A-513 671 has also disclosed compositions containing, as the active ingredient, a total lipophilic extract of the plant
Commiphora mukul
, which is obtained in particular from the resin of the bark of
Commiphora mukul
. This extract contains a high proportion of guggulsterones. This composition is described as having an anti-inflammatory, immunomodulating or antiandrogenic activity for the treatment of acne and benign hypertrophy of the prostate.
It has now been discovered, surprisingly and unexpectedly, that extracts of a plant of the genus Commiphora, particularly the plant
Commiphora mukul
, have an antiwrinkle activity and can thus be used as cosmetic agents for improving the surface appearance of the skin and particularly for reducing the depth of large wrinkles and eliminating small wrinkles.
On the basis of this discovery, the Applicant carried out complementary systematic studies aimed at identifying particularly active fractions responsible for this activity. It found in particular that these fractions contained two novel products which were particularly active as regards the activity in question. These products could be isolated and totally identified from extracts of the plant
Commiphora mukul
. They therefore constitute novel industrial products which have a remarkable activity as cosmetic agents for combating wrinkles.
The invention further relates to derivatives of the two novel products isolated according to the invention.
Thus, according to a first aspect, the invention relates to the products of formula (I):
in which R is:
a) a C H
2
OH group or
b) a COOH group,
and their salts or esters.
The invention relates very particularly, by way of novel industrial products, to the products of formula (II):
in which R is:
a) a CH
2
OH group, the product being denoted by formula II
a
,
b) a COOH group, the product being denoted by formula II
b
,
c) a group
 in which R
1
is a linear or branched alkyl group containing from 1 to 6 carbon atoms, particularly the methyl group,
d) a group COOM, where M denotes an alkali metal, preferably sodium or potassium, or a quaternary ammonium or amine group,
e) a group COOM′
0.5
, where M′ denotes an alkaline earth metal, preferably calcium, or
f) a group COOR
2
, where R
2
denotes a linear or branched alkyl group containing from 1 to 6 carbon atoms.
The invention relates very particularly to the two novel industrial products denoted respectively by II
a
and II
b
and having the following formulae:
The two products could be isolated from the plant
Commiphora mukul
and were completely identified by different analytical techniques, as will become apparent from the following description.
The product of formula II
a
, the empirical formula of which is C
30
H
50
O
3
, will be referred to as “commipherol”. Its nomenclature is as follows:
(5R, 10S,8R,9R)-3-oxopolypoda-13E,17E,21E-triene-8,30-diol.
The acid derivative of formula II
b
, the empirical formula of which is C
30
H48O
4
, will be referred to as “commipherin”. This is (5R,10S,8R,9R)-8-hydroxy-3-oxopolypoda-13E,17E,21 E-trien-30-oic acid.
The nomenclature used to denote the products of formulae II
a
and II
b
above is based on the name of the corresponding hydrocarbon; this is the triterpene &agr;-polypodatetraene, which is well known in the literature, for example in the publication by Yoko Arai et al., Tetrahedron Letters, (1992) 33 (10) 1325-8, relating to the plant Polypodiodes formosane. The carbon atoms are numbered as indicated below:
It should be noted that various triterpene derivatives possessing the polypodane carbon skeleton have been identified in other plants, particularly in ferns of the families of the Polypodiaceae, such as Polypodium vulgare, P. fauriei and P. virginianum (Y. Aral et al., Phytochemistry, (1991) 30 (10) 3369-3377; K. Shiojima et al., Tetrahedron Lett., (1983) 24, 5733), the Aspidiaceae (M. Nishizawa et al., J. Chem. Soc., Chem. Commun. (1984) no. 7, 467-8) and the Cheiropleuriaceae (R. Karnaya et al., Chem. Pharm. Bull. (1990) 38 (8) 2130-2).
According to a second aspect, the invention further relates to processes for the preparation of the two products II
a
and II
b
from the plant
Commiphora mukul
, as well as the acylation derivatives of the product II
a
, particularly the acetylation product, and the salts and esters of the product II
b
.
Different processes can be used to isolate the products of formulae II
a
and II
b
from the plant
Commiphora mukul.
In these processes, it is advantageous to start from the resin of
Commiphora mukul
, which is subjected to different successive extraction and fractionation steps.
Thus, particularly advantageously, the resin of
Commiphora mukul
is subjected to a first so-called extraction step with a solvent or a mixture of solvents, after which the extract is subjected to different separation steps for isolating a particularly active fraction containing at least one of the products of the invention.
The first extraction step can be carried out using a wide range of solvents of very different polarities.
The following may be mentioned, in order of increasing polarity, as examples of solvents which can be used to carry out this step:
petroleum ether, with which 16% by weight of the crude resin can be extracted,
dichloromethane, with which 26% by weight of the crude resin can be extracted,
ethyl acetate, with which 30.5% by weight of the crude resin can be extracted,
ethanol, with which 26.5% by weight of the crude resin can be extracted.


REFERENCES:
patent: 5151272 (1992-09-01), Engstrom et al.
patent: 5273747 (1993-12-01), Bombardelli et al.
patent: 5521223 (1996-05-01), Piazza et al.
patent: 5690948 (1997-11-01), McCook et al.
patent: 5972341 (1999-10-01), Andre et al.

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