Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2001-07-27
2002-12-03
Keys, Rosalynd (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S652000
Reexamination Certificate
active
06489514
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to the isolation of compound namely (−)-Secoisolariciresinol from a new plant source
Stereospermum personatum
. The compound (−)-Secoisolariciresinol {2,3Bis-[4-hydroxy-3-(methoxyphenyl) methyl]-1,4-butanediol} is isolated from new source in good yield.
It is proved to be useful and better antioxidant molecule than the presently used medicinally important lipophilic antioxidants Prubucol and &agr;-Tocopherol. It may have better therapeutic potential in inflammatory disease conditions, atherosclerosis, diabetic complications, cancer, hepatotoxicity and variety of disease conditions mediated through or fostered by oxidative stress and/or overt oxidative burden due to increased generation or under scavenging of free radicals.
BACKGROUND AND PRIOR ART REFERENCES
There is a considerable amount of epidemiological evidence indicating association between diet rich in fruits and vegetables and a decreased risk of cardiovascular disease and certain forms of cancer. It is generally assumed that the active principles contributing to these protective effects are nothing but primarily, the antioxidant phytochemicals.
Research in the past decades have accumulated enough evidence to show the beneficial effect of free-radical scavengers/antioxidants as antimutagenic, anti-inflammatory, antiamerosclerotic, antidiabetic, antihepatotoxic, antiageing and in a variety of neurological disorders. The search for new antioxidant principles is becoming therefore, essential to improve the pharmacological treatment of pathological conditions such as cataract, rheumatic diseases, atherosclerosis, Alzheimer's disease and other neurodegenarative conditions.
The pharmacological approaches therefore have focused on the search of potential resources rich in with antioxidant principles. The medicinal importance of plants bearing rich proportion of antioxidant principles is therefore becoming hot item.
Stereospermum personatum
is a medicinal plant used in traditional Indian System of Medicine and is widely advocated in the preparations for diuretic, lithontriptic, expectorant, cardiotonic, aphrodisiac, appetizer, anti-inflammatory, antibacterial. dyspepsia, diarrhea, renal and vesical calculi, cough, asthma, hyperdipsia, haemorrhoids and hyperacidity disease conditions (Indian Medicinal Plants, Vol 5 p 192). It is further reported to possess antibacterial, antifungal, hypoglycemic activity, and against p388 lymphocytic leukemic cells (Ind. Jour, of Exp. Biol., 1971,9, 100). Hence, it becomes pertinent to look for the molecules possessing such important biological properties. In this connection, the phytochemical investigation of
Stereospermum personatum
has been taken up. The applicants have isolated (−)-Secoisolariciresinol in good yields. (−)-Secoisolariciresinol is known to possess several activities, which are shown in Table 1.
TABLE 1
Compound
Activity
Reference
(−)-Secoisolariciresinol
1. Antitumor agent
Japanese Pat. No.
JP0131J17
2. Cardiotonic
Japanese Pat No.
JP02,101,011
3. Binding to SHBG
Z. Naturforsch, C. Biosc.
997,52,834-843
OBJECTS OF THE INVENTION
The main object of the invention is to provide novel composition containing (−)-Secoisolariciresinol in combination with or associated with additives and useful as an antioxidant.
Another object is to provide a new source for obtaining (−)-Secoisolariciresinol in significant yields.
Yet another object of the invention is to provide a process for producing (−)-Secoisolariciresinol from a plant namely
Stereospermum personatum.
One more object of the invention relates to use of (−)-Secoisolariciresinol as an antioxidant.
SUMMARY OF INVENTION
In accordance with this invention, it has been found that (−)-Secoisolariciresinol is isolated from a new plant source,
Stereospermum Personatum
in significant yield. Also, it has been found that (−)-Secoisolariciresinol show antioxidant property.
DETAILED DESCRIPTION OF THE INVENTION
Accordingly, the invention provides a novel composition containing (−)-Secoisolariciresinol and useful as antioxidant. The invention further provides a method for the isolation of (−)-Secoisolariciresinol from a new source namely
Stereospermum Personatum.
Antioxidant compounds recently have attracted the attention due to their broad spectrum of activities in disorders of multiple origin viz., coronary heart disease, cancer, diabetes, rheumatic disorders and inflammatory conditions where free radicals play important role. Much attention is being directed now to harness and harvest the antioxidant compounds from natural resources.
The compound (−)-Secoisolariciresinol is used in pure form. Hence, the usage may be more advantageous than a mixture of compounds having similar properties, which are in current use. It is also important to note that the process of isolation of (−)-Secoisolariciresinol is highly economical.
Accordingly, the present invention provides a useful source,
Stereospermum Personatum
, comprising antioxidant principle of which (−)-Secoisolariciresinol is isolated as pure and potent antioxidant molecule. (−)-Secoisolariciresinol has been compared with existing pharmacologically/therapeutically accepted antioxidant Probucol and alpha-tocopherol.
It is found that (−)-Secoisolariciresinol is better than the above mentioned reference drugs and hence may be used with pharmaceutically/therapeutically acceptable additives.
In an embodiment of the present invention, (−)-Secoisolariciresinol may be effective in much less amount than the reference drugs mentioned above.
In an embodiment of the present invention relates to a composition useful as antioxidant, said composition comprising an effective amount of (−)-Secoisolariciresinol in combination with or associated with a pharmaceutically acceptable additives.
In another embodiment of the invention, the pharmaceutically acceptable additive is selected in such a manner that it does not affect or interfere with the efficacy of (−)-Secoisolariciresinol.
In still another embodiment of the invention, the additive is selected from nutrients such as carbohydrates, sugar, proteins, fats and pharmaceutically acceptable carrier.
In yet another embodiment of the invention, the amount of (−)-Secoisolariciresinol administered is in the range between 200 mg to 250mg per dose at least twice a day.
In an embodiment of the present invention, the ratio of (−)-Secoisolariciresinol to the additive is in the range between 0.1:10 to 3:10, preferably 0.4:10 to 2:10.
In yet another embodiment of the invention, the composition is administered through oral route in the form of tablets, capsules, syrup or powder.
One embodiment of the invention relates to a process for isolation of (−)-Secoisolariciresinol from the plant
Stereospermum personatum
said process comprising the steps of:
a) extracting the dried wood powder of
Stereospermum personatum
with hexane;
b) further extracting the residue from step (a) with chloroform;
c) concentrating the chloroform solution from step (b) under vacuum;
d) absorbing the dark brown extract on a silicaget (60-120 mesh) and loaded on silicagel (60-120 mesh) column (4 cm diameter to height of 100 cm);
e) eluting the column with chloroform methanol gradient, and
f) collecting the eluted fraction with 3% methanol in chloroform and concentrating the fraction to obtain pure (−)-Secoisolariciresinol.
In another embodiment of the present invention, the solvents used are selected from hexane, chloroform and methanol.
In another embodiment of the present invention, the yield of (−)-Secoisolariciresinol obtained is about 0.03% of the plant dried material.
One more embodiment relates to use of (−)-Secoisolariciresinol as an antioxidant or free-radical scavenger animals and human beings.
In yet another embodiment relates to use of (−)-Secoisolariciresinol for the manufacturing of a composition useful as antioxidant.
In yet another embod
Kumar Upparapalli Sampath
Raghavan Kondapuram Vijaya
Rao Janaswamy Madhusudana
Tiwari Ashok Kumar
Yadav Jhillu Singh
Council of Scientific and Industrial Research
Keys Rosalynd
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