Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1993-10-15
1998-02-17
Peselev, Elli
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
536 41, 536 181, A61K 3170, C07M 1500
Patent
active
057191298
DESCRIPTION:
BRIEF SUMMARY
This invention relates essentially to a new derivative of caffeic acid, oraposide, and cosmetic or pharmaceutical compositions, in particular dermatological compositions, containing it.
More particularly, the new derivative according to the invention, oraposide, is a derivative of caffeic acid extracted from plants of the Orobanchaceae family. The invention also relates to particular derivatives of oraposide, in particular acylated derivatives, and plant extracts containing it, in particular extracts from the broomrape, Rapum genistae.
Preliminary investigations had already revealed that caffeic acid derivatives are present in extracts from the Orobanchaceae, parasitic phanerogamic plants which do not contain chlorophyll (Andary et al., 1980, Il Farmaco, 1, 1-30; Bridel and Charaux, 1924, C.R. Acad. Sci. 178, 1839), but their structure had not been dearly established.
The pharmacological benefits of caffeic acid (or 3,4-dihydroxycinnamic acid) and several natural derivatives of it have already been the object of many investigations. Thus Kimura et al. (Planta Medica, 1984, 473-477) have investigated the effect of various tannins and in particular caffeic acid and caffeoylquinic acid derivatives extracted from plants of the species Artemisia and have demonstrated their inhibitory effect on the peroxidation of lipids in rat liver mitochondria and microsomes. The inhibitive effect of these molecules on the lipoxygenases which are involved in leucotriene and arachidonic acid metabolism and their potential use in the treatment of inflammatory conditions like asthma have also been published by Kimura and Okuda (J. of Natural Products, 1987, 50, 392-399).
As different caffeic derivatives are active in a variety of ways which vary in relation to their structure, it is of advantage to investigate new molecules in this family, in medicinal or other plants, and to search for new pharmacological activities or improved performance.
Thus a new compound, which has particularly interesting properties, has been obtained from extracts of plants of the Orobanchaceae family which parasitise various brooms (Cytisus scoparius and purgans) as well as food plants such as lentils, beans and the Solanaceae (tomatoes, aubergines). The broomrape is a perennial plant comprising a stem with a flowering spike, and the whole plant may attain a length of 20 to 100 cm, with scales all along the stem, which ends at the base in a bulb which is also covered with scales. The entire plant is rich in heteroside caffeic ester derivatives. The bulb, the organ which is attached to the roots of the host plant by tendrils in the form of small roots, is the organ containing the highest concentrations of these heteroside caffeic esters.
The substance extracted from the broomrape, Rapum genistae, has been obtained in a pure crystallised form, e.g. by steeping an extract of the plant or plant cells in alcohol, and has been subjected to various conventional analyses which have made it possible to establish its molecular configuration and structure (chromatographic separations, determination of melting point, investigation of NMR spectra, mass spectra, X-ray, IR and UV spectra and various biochemical analyses). The formula which has been deduced from these analyses is as follows: beta.-D-glucopyranoside 4-caffeate.
This substance, which it has been proposed should be called "oraposide", is represented by a formula (I) below, in which R is a hydrogen atom. ##STR2##
This invention also relates to derivatives of formula I in which one or more R independently represent an atom of hydrogen, a lower C.sub.1 -C.sub.5 alkyl, in particular methyl, or an acyl group, in particular one containing C.sub.1 -C.sub.6, in particular acetyl.
In accordance with another preferred feature, only the OR groups on the benzene rings are alkylated, and in particular methylated.
Preferably, only the OR groups on glucopyranosyl or rhamnopyranosyl rings are acylated, in particular acetylated.
In particular, oraposide or its derivatives are extracted from a plant of the Orobanchaceae f
REFERENCES:
Chemical Abstracts, vol. 106, No. 19, May 11, 1987, p. 574, Abstract 155103s.
Chemical Abstracts, vol. 107, No. 6, Aug. 10, 1987, p. 407, Abstract 46141c.
Chemical Abstracts, vol. 107, No. 7, Aug. 17, 1987, p. 37, Abstract 51592e.
Chemical Abstracts, vol. 114, No. 10, Mar. 11, 1991, p. 423, Abstract 88423w.
Andary Claude
Andre Patrice
Parfums Christian Dior
Peselev Elli
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