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Title:  .alpha.-Glucosidase inhibitors from a natural source
United States Patent: 
7,081,260
Issued: 
July 25, 2006

Inventors: 
Rao; Janaswamy Madhusudana (Hyderabad, IN); Srinivas; Pullela Venkata (Hyderabad, IN); Anuradha; Vummenthala (Hyderabad, IN); Tiwari; Ashok Kumar (Hyderabad, IN); Ali; Amtul Zehra (Hyderabad, IN); Yadav; Jhillu Singh (Hyderabad, IN); Raghavan; Kondapuram Vijaya (Hyderabad, IN)
Assignee: 
Council of Scientific and Industrial Research (New Dehli, IN)
Appl. No.:  
10/282,011
Filed:  
October 29, 2002


 

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Abstract

The present invention relates to a method for providing .alpha.-glucosidase inhibition to a subject by administering a pharmaceutical composition comprising a .alpha.-glucosidase inhibitory agent selected from pipataline (formula 1a), sesamin (formula 1b), pellitorine (Formula 1c), guineensine (Formula 1d) and brachystamide-B (formula 1e) having therapeutic application for diabetes mellitus, cancer, viral diseases such as hepatitis B and C, HIV, AIDS etc; also the invention provides a process for the isolation of said .alpha.-glucosidase inhibitory agent from the plant source Piper longum in significant yields.

SUMMARY OF THE INVENTION

Accordingly, the present invention relates to a method for providing .alpha.-glucosidase inhibition to a subject by administering a pharmaceutical composition comprising a .alpha.-glucosidase inhibitory agent selected from pipataline (formula 1a), sesamin (formula 1b), pellitorine (Formula 1c), guineensine (Formula 1d) and brachystamide-B (formula 1e).

The present invention relates to a new activity for pipataline or sesamin or pellitorine or guineensine or brachystamide-B obtained from Piper longum as an .alpha.-glucosidase inhibitor in the management and treatment of human diseases like hyperglycemia, hyperinsulinemia, hyperlipoproteinemea, cancer, viral infection, hepatitis B and C, HIV and AIDS.

The invention also relates to isolation of pipataline from a new source, namely Piper longum. Another aspect of the invention is to provide a process for isolating pipataline or sesamin or pellitorine or guineensine or brachystamide-B obtained from Piper longum in good yields.

DETAILED DESCRIPTION OF THE INVENTION

In accordance to the objectives of the invention, the present invention provides a method for providing .alpha.-glucosidase inhibition to a subject, said method comprising administering to the subject an effective amount of a pharmaceutical composition comprising an .alpha.-glucosidase inhibitory agent selected from pipataline (formula 1a), sesamin (formula 1b), pellitorine (Formula 1c), guineensine (Formula 1d) and brachystamide-B (formula 1e) along with a pharmaceutically acceptable ingredient in management and treatment of diseases like hyperglycemia, hyperinsulinemia, hyperlipoproteinemea, cancer, viral infection, hepatitis B and C, HIV and AIDS in the subject.

In an embodiment of the invention, pipataline provides .alpha.-glucosidase inhibitory activity up to 77.45% with an IC.sub.50 value of 26.52 (.mu.g/ml).

In another embodiment of the invention, sesamin provides .alpha.-glucosidase inhibitory activity up to 76.18% with an IC.sub.50 value of 36.35(.mu.g/ml).

In another embodiment of the invention, pellitorine provides .alpha.-glucosidase inhibitory activity up to 86.03% with an IC.sub.50 value of 34.43(.mu.g/ml).

In another embodiment of the invention, guineensine provides .alpha.-glucosidase inhibitory activity up to 61.71% with an IC.sub.50 value of 20.15(.mu.g/ml).

In another embodiment of the invention, brachystamide-B provides .alpha.-glucosidase inhibitory activity up to 73.90% with an IC.sub.50 value of 33.61(.mu.g/ml).

In another embodiment of the invention, the pharmaceutical composition containing pipataline or sesamin or pellitorine or guineensine or brachystamide-B optionally consists of pharmaceutically acceptable ingredients.

Still another embodiment of the present invention provides a process for isolation of pipataline from Piper longum for the first time.

One more embodiment of the invention provides a process of isolation of an .alpha.-glucosidase inhibitory agent selected from pipataline (formula 1a), sesamin (formula 1b), pellitorine (Formula 1c), guineensine (Formula 1d) and brachystamide-B (formula 1e) from the plant source Piper longum, the process comprising the steps of: a. extraction the dried fruits of Piper longum with a solvent, b. concentrating the extract under vacuum to obtain a residue; c. eluting the residue of step (b) with hexane to obtain pipataline and a residue, d. eluting the residue of step (c) with about 3% ethyl acetate in hexane to obtain sesamin and a residue, e. eluting the residue of step(d) with about 5% ethyl acetate in hexane to obtain pellitorine and a residue, f. eluting the residue of step(e) with about 10% ethyl acetate in hexane to obtain guineensine and a residue; and g. subjecting further elution of the residue of step (f) with about 11% ethyl acetate in hexane to obtainbrachystamide-B.

In one embodiment, the solvent used in step (a) is selected from hexane, cyclohexane or n-pentane.

Another embodiment of the invention relates to the isolation of pipataline from an entirely new source.

Still another embodiment of the invention relates to the isolation of these compounds from Piper longum as .alpha.-glucosidase inhibitors.

The present invention embodies the isolation of pipataline, sesamin, pellitorine, guineensine, brachystamide-B as .alpha.-glucosidase inhibitory principles from Piper longum among which pipataline is from an entirely new source.

The present invention relates to the isolation of five compounds, namely pipataline [5-(1-dodecenyl)-1,3-benzodioxol], sesamin [5,5-(tetrahydro-1H,3H-furo {3,4-e)furan-1,4-diyl) bis-1,3-benzodioxol], pellitorine [N-(2-methyl propyl)-2,4-decadienamide], guineensine [13-(1,3-benzodioxol-5-yl)-N {2-methyl propyl)-2,4,12-tridecatrienamide], brachystamide-B [[15-(1,3-benzodioxol-5-yl)-N(2-methyl propyl)-2,4,14-pentadecatrienamide] from the plant source Piper longum in significant yields. Among the above said compounds pipataline is from an entirely new source. This invention also relates to the new use of these compounds as .alpha.-glucosidase inhibitors.

The present invention embodies isolation of of pipataline, sesamin, pellitorine, guineensine and brachystamide-B, five .alpha.-glucosidase inhibitory principles from Piper longum, among which pipataline is from an entirely new source.
 


Claim 1 of 2 Claims

1. A method for treating a metabolic disease selected from the group consisting of hyperglycemia, hyperinsulinemia and hyperlipoproteinemia in a subject presenting symptoms of the metabolic disease comprising administering to the subject an amount of a compound selected from the group consisting of pipataline ##STR00001## (see Original Patent) guineensine ##STR00002## (see Original Patent) and brachystamide-B ##STR00003## (see Original Patent) effective for treating the metabolic disease.

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If you want to learn more about this patent, please go directly to the U.S. Patent and Trademark Office Web site to access the full patent.

 

 

     
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