Borate complexes of chlorogenic acid and uses thereof
AssigneeP.L. Thomas & Co., Inc.
InventorsIon Romulus Scorei, Andrei Bita, Laura Dinca, George Dan Mogosanu, Nagendra Rangavajla
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Abstract
A borate diester of chlorogenic acid is prepared by reacting a solution comprising chlorogenic acid and boric acid in a ratio of at least 2:1 in a superheated water solvent or an aqueous acetonitrile solvent. If aqueous acetonitrile is used as a solvent, the acetonitrile solvent is evaporated to leave a water solution. A product containing the desired borate diester is obtained by freeze-drying or air-drying the water solution. Insufficient levels of boron in a microbiome in a subject in need thereof may be treated by administering the borate diester of chlorogenic acid to the subject.
Claims19
A method of producing an extract comprising a chlorogenic acid and a borate diester of chlorogenic acid, wherein the method comprises:
- i. extracting green coffee beans in a solvent comprising water or a mixture of water and an organic solvent to produce an aqueous reaction mixture;
- and
- ii. producing the extract comprising the chlorogenic acid and the borate diester by a step selected from the group consisting of:
- freeze-drying the aqueous reaction mixture;
- and
- evaporating water from the aqueous reaction mixture;
- wherein the method further comprises adding boric acid to the aqueous reaction mixture to provide the extract with an increased content of the borate diester.
A method of producing an composition comprising a borate ester of chlorogenic acid, wherein the method comprises:
- i. reacting a chlorogenic acid with boric acid in a solvent comprising water or a mixture of water and an organic solvent to produce an aqueous reaction mixture;
- and
- ii. producing the extract comprising the borate ester of chlorogenic acid by a step selected from the group consisting of:
- freeze-drying the aqueous reaction mixture;
- and
- evaporating water from the aqueous reaction mixture.
A method of treating boron insufficiency of a microbiome in a subject in need thereof, comprising administering an effective amount of a borate ester of chlorogenic acid to the subject, wherein the borate ester has a structure of formula (I) or a structure of formula (II), where X is hydrogen or a pharmaceutically acceptable cation:
A method of treating dysbiosis of a microbiome in a patient, comprising:
- obtaining a sample comprising bacteria from the microbiome of the patient, wherein:
- the microbiome is in an oral mucosa, and the sample comprises a sample of saliva or an oral mucus gel layer;
- or
- the microbiome is in a colon, and the sample comprises a stool sample or a sample of a colonic mucus gel layer;
- detecting a level of furanosyl borate diester in the sample, where the detected level of furanosyl borate diester is less than a target value;
- and
- increasing the level of furanosyl borate diester in the microbiome of the patient by administering a composition to the patient;
- wherein the composition is produced by a process comprising:
- i. reacting a green coffee bean extract comprising a chlorogenic acid with boric acid in a solvent comprising water or a mixture of water and an organic solvent to produce an aqueous reaction mixture,
- wherein boric acid is added to the aqueous reaction mixture to provide the green coffee bean extract with an increased content of the borate diester;
- and
- ii. freeze-drying the aqueous reaction mixture to produce the composition comprising the borate ester of chlorogenic acid.
Dependencies are inferred from the claim text.