Method for obtaining oleocanthal type secoiridoids and for producing respective pharmaceutical preparations
The present invention relates to the method for obtaining in pure form or as a mixture of the bioactive diol forms of the main secoiridoid phenols present in olive oil and certain isomeric forms or derivatives thereof. Specifically, it relates to the production process of S-(E)-oleocanthadiol, S-(E)-oleaceinediol, 5S-(E)-oleomissionadiol, 5S-(E)-oleokoronadiol, oleuropeinediol and ligstrodiol and their corresponding polyethylene glycol hemiacetals through extraction of specifically selected olive oil with polyethylene glycol and then treated with water. It also relates to the pharmaceutical preparations containing the above substances in various combinations and the therapeutic properties of these preparations for the treatment of cancer, degenerative diseases of the central nervous system, diabetes, hyperlipidemia, inflammatory diseases and the prevention of creation of atherosclerotic plaques and thrombi.
1 . Secoiridoids of type I and/or II
wherein
I: R1=H, R2=H or COOCH 3 , R3=X1
II: R1=H or OH, R3=X1; and
wherein the secoiridoids are pegylated with polyethylene glycol (PEG) having an average molecular weight from 200 to 400, at a PEG-to-secoiridoid ratio ranging from 1:1 to 100:1.
2 . Secoiridoids of type I and/or II
wherein
I: R1=H, R2=H or COOCH 3 , R3=X1
II: R1=H or OH, R3=X1 individually or in any combination thereof,
the secoiridoids being pegylated with polyethylene glycol (PEG) having an average molecular weight from 200 to 400, at a PEG-to-secoiridoid ratio ranging from 1:1 to 100:1, for the production of pharmaceutical preparations for oral or transdermal administration or injectable solutions or suppositories or tablets produced after drying and compression.
3 . Secoiridoids of type I and/or II
wherein
I: R1=H, R2=H or COOCH 3 , R3=X1,
II: R1=H or OH, R3=X1,
the secoiridoids being pegylated with polyethylene glycol (PEG) having an average molecular weight from 200 to 400, at a PEG-to-secoiridoid ratio ranging from 1:1 to 100:1, for the manufacture of nutritional supplements.
4 . A pharmaceutical preparation containing the secoiridoids of claim 2 for the treatment of cancer, and inflammatory diseases, and for preventing the creation of atherosclerotic plaques and thrombi, wherein the pharmaceutical preparation is administered at a dose ranging from 1 mg to 1000 mg.
5 . Secoiridoids of type I and/or II
wherein
I: R1=H, R2=H or COOCH 3 , R3=X1
II: R1=H or OH, R3=X1,
the secoiridoids being pegylated with polyethylene glycol (PEG) having an average molecular weight from 200 to 400, at a PEG-to-secoiridoid ratio ranging from 1:1 to 100:1, for the preparation of solutions to sterilize solid materials.
6 . A pharmaceutical preparation containing the secoiridoids of claim 2 , wherein the secoiridoids are obtained from olive oil of the species Olea europaea L or any of its subspecies and cultivars, containing secoiridoids of type I and/or II with R1=H or OH, R2=H or COOCH3, R3=CHO and their tautomers, either in individual form or in any combination thereof; and wherein the olive oil is mixed with the polyethylene glycol (PEG) having an average molecular weight from 200 to 400, at a PEG:olive oil ratio ranging from 1:1 to 1:100.
7 . A pharmaceutical preparation containing the secoiridoids of claim 3 , wherein the secoiridoids are obtained from olive oil of the species Olea europaea L or any of its subspecies and cultivars, containing secoiridoids of type I and/or II with R1=H or OH, R2=H or COOCH3, R3=CHO and their tautomers, either in individual form or in any combination thereof; and wherein the olive oil is mixed with the polyethylene glycol (PEG) having an average molecular weight from 200 to 400, at a PEG:olive oil ratio ranging from 1:1 to 1:100.
8 . A pharmaceutical preparation containing the secoiridoids of claim 1 , wherein the secoiridoids are obtained from olive oil of the species Olea europaea L or any of its subspecies and cultivars, containing secoiridoids of type I and/or II with R1=H or OH, R2=H or COOCH3, R3=CHO and their tautomers, either in individual form or in any combination thereof; and wherein the olive oil is mixed with the polyethylene glycol (PEG) having an average molecular weight from 200 to 400, at a PEG:olive oil ratio ranging from 1:1 to 1:100.
9 . A pharmaceutical preparation containing the secoiridoids of claim 5 , wherein the secoiridoids are obtained from olive oil of the species Olea europaea L or any of its subspecies and cultivars, containing secoiridoids of type I and/or II with R1=H or OH, R2=H or COOCH3, R3=CHO and their tautomers, either in individual form or in any combination thereof; and wherein the olive oil is mixed with the polyethylene glycol (PEG) having an average molecular weight from 200 to 400, at a PEG:olive oil ratio ranging from 1:1 to 1:100.