Compositions Of Bakuchiol And Methods Of Making The Same

a technology of bakuchiol and bakuchiol, which is applied in the field of bakuchiol compositions, can solve the problems of psoralens presence, number of limitations associated with the use of this compound, and the association of health risks

Inactive Publication Date: 2006-11-09
UNIGEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0025] Also included in the present invention is a method for analyzing compositions of bakuchiol, which enables detection and quantification of impurities. In this embodiment of the invention, the method for analyzing compositions of bakuchiol is comprised of the step of analyzing said compositions by high-pressure liquid chromatography (HPLC). Analysis by HPLC enables quantification of the various components in the mixture and also provides a means to track bakuchiol, psoralen, isopsoralen and other natural components in Psoralea plants to guide the extraction, hydrolysis and purification processes.

Problems solved by technology

However, there are currently a number of limitations associated with the use of this compound due primarily to its low concentration in natural sources, as well as the presence of co-existing toxic components.
One of the main problems related to the use of bakuchiol compositions isolated from plants in the Psoralea genus is the presence of psoralens, such as psoralen and isopsoralen, the structures of which are set forth below.
A number of health risks have been associated with the handling, topical application and ingestion of psoralen-containing plants and synthetic psoralens.
Unfortunately, drug resistance by both Propionibacterium acnes and Staphylococcus epidermidis has been reported (Nishijima et al.
Endotoxins released by the anaerobic bacteria cause inflammation, gum tissue destruction and even bone loss.
The destructive impact of periodontal disease goes beyond dental hygiene and health, in that microscopic lesions resulting from periodontal disease have been found in the liver, kidneys, and brain of some affected persons.
Current methods for treating periodontal disease are limited with control of the infection being the primary goal.
Unfortunately, there is currently no single periodontal medication which functions to both control the inflammation as well as inhibit the infection.

Method used

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  • Compositions Of Bakuchiol And Methods Of Making The Same
  • Compositions Of Bakuchiol And Methods Of Making The Same
  • Compositions Of Bakuchiol And Methods Of Making The Same

Examples

Experimental program
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Effect test

example 1

Method for the Quantification of Bakuchiol, Psoralen and Isopsoralen by HPLC

[0093] The amount of bakuchiol, psoralen and isopsoralen in the extracts, fractions, and the novel composition generated as described below was quantified by a high pressure liquid chromatography (HPLC) using a PhotoDiode Array detector (HPLC / PDA) and a Luna Phenyl-hexyl column (250 mm×4.6 mm). The targeted compounds were eluted from the column using an acetonitrile (ACN) water gradient from 36% to 100% ACN over a period of 12 minutes, followed by 100% ACN for three minutes. The detailed HPLC conditions used are set forth in Table 1. A chromatogram of the HPLC separation is depicted in FIG. 1. The targeted compounds were identified and quantified based on retention time and UV peak area using commercially available pure bakuchiol, psoralen and isopsoralen as quantification standards. The retention times for the bakuchiol, psoralen and isopsoralen were 18.19 minutes, 7.33 minutes and 7.95 minutes, respective...

example 2

General Methods for the Extraction of Bakuchiol from Psoralea Plants

Wrist Shaker

[0094] To a flask was added solvent (100 mL) and Psoralea corylifolia seed powder (10 g) and the mixture was shaken on a wrist shaker at room temperature for one hour. The mixture was then passed through a filter and the filtrate collected. The extraction process was repeated one more time with fresh solvent, the filtrates were combined, the solvent removed on a rotoevaporator and the residue was dried under high vacuum.

Reflux

[0095] To a flask was added solvent (50 mL) and Psoralea corylifolia seed powder (10 g) and the mixture was refluxed for 40 min. The solution was then filtered and the extraction process was repeated two more times with fresh solvent. The filtrates were combined and the solvent was evaporated to obtain a dried extract.

[0096] Following above extraction methods, sample plant material was extracted with the following solvents: dichloromethane (DCM), EtOAc, acetone, MeOH, petrole...

example 3

Large Scale Extraction of Bakuchiol from Psoralea Plants

[0097] Seed powder of Psoralea corylifolia (2 kg) and 9 liter of petroleum (pet.) ether (BP 60-90° C.) were rotated in a 20 L flask on a rotoevaporator at 70° C. in a water bath for 1 hour. The solution was then decanted into a separate container and the solvent was removed under vacuum. Fresh solvent was added into the biomass and the extraction process was repeated three more times. The extracts were combined and evaporated to yield 335 g of a crude extract (MH-258-01-01) having 21% bakuchiol and 3% psoralen / isopsoralen by weight.

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Abstract

The present invention provides compositions of bakuchiol (UP246) having low levels of impurities, particularly furanocoumarin impurities. The present invention further provides improved methods for the isolation, purification and analysis of compositions of bakuchiol. Finally, the present invention provides methods for using the purified bakuchiol compositions and formulations thereof for the prevention and treatment of various diseases and conditions mediated by cyclooxygenase (COX), lipoxygenase (LOX), minor inflammatory conditions and various microbial infections. The methods of this invention are comprised of administering to a host in need thereof an effective amount of the composition of this invention together with a pharmaceutically acceptable carrier.

Description

RELATED APPLICATIONS [0001] This application claims the benefit of U.S. Provisional Application Ser. No. 60 / 679,337, filed May 9, 2005, entitled “Generation of High Purity Bakuchiol as a Therapeutic Agent,” which is incorporated herein by reference in its entirety.FIELD OF THE INVENTION [0002] The present invention relates to compositions of bakuchiol and compounds related thereto having low levels of impurities, particularly furanocoumarin impurities. The present invention provides improved methods for the isolation, purification and analysis of compositions of bakuchiol. Finally, the present invention provides methods for using the purified bakuchiol compositions and formulations thereof for the prevention and treatment of various diseases and conditions mediated by cyclooxygenase (COX), lipoxygenase (LOX), minor inflammatory conditions and various microbial infections. BACKGROUND OF THE INVENTION [0003] Bakuchiol, the structure of which is illustrated below, is a phenolic compoun...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/05A61K36/48
CPCA61K9/0014A61K36/487A61K31/05A61P1/02A61P1/04A61P3/04A61P3/10A61P9/00A61P9/10A61P11/02A61P15/08A61P17/00A61P17/02A61P17/04A61P17/06A61P17/10A61P17/16A61P19/02A61P19/08A61P25/06A61P25/08A61P25/28A61P29/00A61P31/04A61P31/10A61P31/12A61P35/00A61P37/06A61P43/00Y02A50/30A61K36/48C07D473/00
Inventor JIA, QIHONG, MEI-FENG
Owner UNIGEN
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