Non-fluorescent chlorophyll catabolites
AssigneeLeopold-Franzens-Universitat Innsbruck
InventorsBernhard Kräutler, Thomas Müller
Life of this patent
Estimating the term…
Abstract
The invention relates to a compound of formula (I), or a pharmacologically or cosmetically acceptable salt or derivative thereof, wherein R1 to R5 are selected from the groups R1 representing -alkyl, -vinyl, —CHOH—CH2OH, R2 representing H, —OH, —Oalkyl, —Oacyl, saccharide groups, modified saccharide groups (e.g. malonylated), R3 representing —H, —OH, —Oalkyl, —Oacyl, modified —Oacyl (e.g. malonylated), saccharide groups, modified saccharide groups (e.g. malonylated), R4, R5 representing —COOH, -carbonic esters, for use as drug, antioxidant, food supplement. The invention also relates to a method for producing the compound of formula (I).
Claims44
A preparation comprising:
- at least one compound of formula I
- or a pharmacologically, dermatologically or cosmetically acceptable salt thereof, wherein R1 is -alkyl, -vinyl, or —CHOH—CH2OH;
- R2 is —H, —OH, —O-alkyl, —O-acyl, saccharide radicals, or modified saccharide radicals;
- R3 is —H, —OH, —O-alkyl, —O-acyl, modified —O-acyl, saccharide radicals, or modified saccharide radicals;
- R4 is —COOH or a carboxylic acid ester;
- and R5 is —COOH or a carboxylic acid ester;
- and
- at least one substance selected from the group consisting of an antioxidant and a vitamin.
A method of using a compound of formula I
- or a pharmacologically, dermatologically or cosmetically acceptable salt thereof, wherein R1 is -alkyl, -vinyl, or —CHOH—CH2OH;
- R2 is —H, —OH, —O-alkyl, —O-acyl, saccharide radicals, or modified saccharide radicals;
- R3 is —H, —OH, —O-alkyl, —O-acyl, modified —O-acyl, saccharide radicals, or modified saccharide radicals;
- R4 is —COOH or a carboxylic acid ester;
- and R5 is —COOH or a carboxylic acid ester, as a preservative,
- said method comprising contacting the compound, pharmacologically, dermatologically or cosmetically acceptable salt thereof with an article to be preserved.
A method of using a compound of formula I
- or a pharmacologically, dermatologically or cosmetically acceptable salt thereof, wherein R1 is -alkyl, -vinyl, or —CHOH—CH2OH;
- R2 is —H, —OH, —O-alkyl, —O-acyl, saccharide radicals, or modified saccharide radicals;
- R3 is —H, —OH, —O-alkyl, —O-acyl, modified —O-acyl, saccharide radicals, or modified saccharide radicals;
- R4 is —COOH or a carboxylic acid ester;
- and R5 is —COOH or a carboxylic acid ester, as an antibacterial agent,
- said method comprising contacting the compound, pharmacologically, dermatologically or cosmetically acceptable salt thereof with bacteria.
A method of using a compound formula I
- or a pharmacologically, dermatologically or cosmetically acceptable salt thereof, wherein R1 is -alkyl, -vinyl, or —CHOH—CH2OH;
- R2 is —H, —OH, —O-alkyl, —O-acyl, saccharide radicals, or modified saccharide radicals;
- R3 is —H, —OH, —O-alkyl, —O-acyl, modified —O-acyl, saccharide radicals, or modified saccharide radicals;
- R4 is —COOH or a carboxylic acid ester;
- and R5 is —COOH or a carboxylic acid ester, as a fungicide,
- said method comprising contacting the compound, pharmacologically, dermatologically or cosmetically acceptable salt thereof with a fungus.
A method of using a compound of formula I
- or a pharmacologically, dermatologically or cosmetically acceptable salt thereof, wherein R1 is -alkyl, -vinyl, or —CHOH—CH2OH;
- R2 is —H, —OH, —O-alkyl, —O-acyl, saccharide radicals, or modified saccharide radicals;
- R3 is —H, —OH, —O-alkyl, —O-acyl, modified —O-acyl, saccharide radicals, or modified saccharide radicals;
- R4 is —COON or a carboxylic acid ester;
- and R5 is —COON or a carboxylic acid ester, as a food supplement,
- said method comprising supplementing the compound, pharmacologically, dermatologically or cosmetically acceptable salt thereof for food.
A method of treating carcinoma, comprising administering a therapeutically effective amount of a compound of formula I
- or a pharmacologically, dermatologically or cosmetically acceptable salt thereof, wherein R1 is -alkyl, -vinyl, or —CHOH—CH2OH;
- R2 is —H, —OH, —O-alkyl, —O-acyl, saccharide radicals, or modified saccharide radicals;
- R3 is —H, —OH, —O-alkyl, —O-acyl, modified —O-acyl, saccharide radicals, or modified saccharide radicals;
- R4 is —COOH or a carboxylic acid ester;
- and R5 is —COOH or a carboxylic acid ester,
- to a patient in need thereof.
A method of preparing a cosmetic preparation, a pharmaceutical preparation, a foodstuff or a food supplement,
- said method comprising contacting a compound of formula I
- or a pharmacologically, dermatologically or cosmetically acceptable salt thereof, wherein R1 is -alkyl, -vinyl, or —CHOH—CH2OH;
- R2 is —H, —OH, —O-alkyl, —O-acyl, saccharide radicals, or modified saccharide radicals;
- R3 is —H, —OH, —O-alkyl, —O-acyl, modified —O-acyl, saccharide radicals, or modified saccharide radicals;
- R4 is —COOH or a carboxylic acid ester;
- and R5 is —COOH or a carboxylic acid ester,
- with a cosmetic, a pharmaceutical, a foodstuff or a food supplement.
A process for producing non-fluorescent chlorophyll catabolites of formula I
- or a pharmacologically, dermatologically or cosmetically acceptable salt thereof, or a plant salt thereof,
- wherein R1 is -alkyl, -vinyl, or —CHOH—CH2OH;
- R2 is —H, —OH, —O-alkyl, —O-acyl, saccharide radicals, or modified saccharide radicals;
- R3 is —H, —OH, —O-alkyl, —O-acyl, modified —O-acyl, saccharide radicals, or modified saccharide radicals;
- R4 is —COOH or a carboxylic acid ester;
- and R5 is —COOH or a carboxylic acid ester,
- from a plant material,
- said method comprising the steps:
- extraction of the plant material with a first solvent or solvent mixture with a dielectric constant of 5 to 20 and a dipole moment of 5 to 10×10−30 cm to form a crude extract
- filtration by column chromatography of this extract over silica gel
- elution of the silica gel with a second solvent or solvent mixture, and
- drawing off of the solvent to obtain a residue, and optional crystallization of the obtained residue.
A method of protecting against oxidative stress and combating allergies, inflammations or irritations,
- said method comprising administering a therapeutically effective amount of a compound of formula I
- or a pharmacologically, dermatologically or cosmetically acceptable salt thereof, wherein R1 is -alkyl, -vinyl, or —CHOH—CH2OH;
- R2 is —H, —OH, —O-alkyl, —O-acyl, saccharide radicals, or modified saccharide radicals;
- R3 is —H, —OH, —O-alkyl, —O-acyl, modified —O-acyl, saccharide radicals, or modified saccharide radicals;
- R4 is —COOH or a carboxylic acid ester;
- and R5 is —COOH or a carboxylic acid ester,
- to a patient in need thereof.
Dependencies are inferred from the claim text.