Antioxidant from natural source

Details Antioxidant from natural source Antioxidant from natural source

2003-02-28

2004-08-24

Owens, Amelia (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06781002

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to the isolation of a new compound namely (−)-mesquitol from a plant source,
Dichrostachys cinerea
in good yield.
BACKGROUND ART
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, antiinflammatory, antiatherosclerotic, 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 related either due to free radical/oxidative damage or due to imbalance between antioxidant/oxidant homeostasis such as cataract, rheumatic diseases, atherosclerosis, Alzheimer's disease and other neurodegenerative conditions. The pharmacological approaches therefore have focused the search for potential resources rich in antioxidant principles. The medicinal importance of plants bearing rich proportion of antioxidant principles is therefore becoming hot item.
Dichrostachys cinerea
is a medicinal plant used in the traditional Indian system of medicine and is widely advocated in diuretic, lithotriptic, anodyne, digestive, constipating, and inflammatory conditions. Also it is useful in vitiated conditions of kapha and vata, arthralgia, elephantiasis, dyspepsia, diarrhea, vesicle calculi, strangury, nephropathy, vaginopathy and metropathy (
Indian Medicinal Plants
, Vol.2 p.330).It is useful in opthalmia, rheumatism, urinary calculi and renal troubles (
Wealth of India
Vol.3 p.56).It is further reported to possess protease inhibitor activity (CA, 90, 118086u), fungi toxic activity (
Ind. J. plant. Physiol,
1986, 29(3), 278-80.), antibacterial (
Fitoterapia,
1988, 59(1), 57-62.). Hence it becomes pertinent to look for the molecules possessing such important biological properties. In this connection, the phytochemical investigation of
Dichrostachys cinerea
has been taken up. The applicants made efforts to the isolation of a new compound (−)-mesquitol as free radical scavenger in substantial yield. The isomer (+)-mesquitol was previously reported from
Prosopis glandulosa
in 0.011% yield (
J. Chem. Soc. Perkin. Trans I
, 1986, 1737).
OBJECTS OF THE INVENTION
The main object of the invention is to provide a novel compound, (−)-mesquitol useful as an antioxidant.
Another object of the invention is to provide a process for producing (−)-mesquitol from a plant source namely
Dichrostachys cinerea
in substantial yield.
Yet another object of the invention is (−)-mesquitol is a new compound.
Yet another object of the invention is (−)-mesquitol is isolated in 99.9% pure form.
Yet another object of the invention relates to the use of (−)-mesquitol as an antioxidant.
SUMMARY OF INVENTION
Accordingly, the invention provides a novel compound as shown in
FIG. 2
derived from a natural source namely (−)-mesquitol useful as an antioxidant. The invention further provides a method for the isolation of (−)-mesquitol in 99.9% pure from the plant
Dichrostachys cinerea
In accordance with this invention, it has been found that (−)-mesquitol is isolated from a natural source,
Dichrostachys cinerea
in significant yield and it has been found that (−)-mesquitol is a new compound isolated for the first time and shows antioxidant property.
DETAILED DESCRIPTION OF THE INVENTION
Antioxidant compounds recently have attracted 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 an important role. Much attention is being directed now to harness and harvest the antioxidant compositions and or compounds from natural resources.
The present invention provides an antioxidant compound (−)-mesquitol as shown in
FIG. 2
, obtained from an useful and new source
Dichrostachys cinerea
. (−)-Mesquitol is isolated as a pure and potent antioxidant molecule from the said new source. (−)-Mesquitol has been compared with existing pharmacologically/therapeutically accepted antioxidant probucol and &agr;-tocopherol. It is found that (−)-mesquitol is better than the above mentioned reference drugs and hence may be used with pharmaceutically/therapeutically acceptable additives. It is proved to be useful and better antioxidant molecule than the presently used medicinally important lipophilic antioxidants probucol 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.
In an embodiment of the present invention, (−)-mesquitol may be effective in much less amount than the reference drugs mentioned above.
One embodiment of the present invention relates to a compound useful as an antioxidant.
The process for the isolation of (−)-mesquitol from
Dichrostachys cinerea
comprising the steps of:
(a) extracting the dried wood powder of
Dichrostachys cinerea
with hexane;
(b) extracting the residue of step (a) with chloroform;
(c) extracting the residue of step (b) with methanol to obtain a methanolic extract;
(d) concentrating the methanolic extract of step (c) under vacuum;
(e) adsorbing the concentrated methanolic extract of step (d) on silica gel (60-120 mesh) and loading on silica gel column (5 cms diameter to a height of 100 cms);
(f) eluting the column with chloroform methanol gradient,
(g) collecting the fraction eluted at 5% methanol in chloroform, and
(h) concentrating the eluted fraction of step (g) to obtain pure (−)-mesquitol.
In an embodiment of the present invention, the solvent used or selected for isolation is from Hexane, Chloroform and Methanol.
In another embodiment of the present invention, the yield of (−)-mesquitol obtained is about 1.5% of the dried material. The percentage recited herein is the percent by weight.
One more embodiment relates to the use of (−)-mesquitol as an antioxidant/free-radical scavenger useful as therapeutic agent where free radicals are involved in causing/mediating disease conditions.
Dichrostachys cinerea
is a source for (−)-mesquitol and its presence in this plant in substantial yields make this invention more important.
The present invention embodies isolation of new compound (−)-mesquitol, as an antioxidant principle from a plant source and identifies its free-radical scavenging property compared with medicinally important antioxidant drug molecules.


REFERENCES:
Rao, et al, ‘Novel 3-O-acyl mesquitol analogues as free-Radical scavengers and enzyme inhibitors: synthesis, biological evaluation and structure-activity relationship’ Bioorganic & Medicinal Chemistry Letters (2003), 13(16), 2777-2780.*
Young, et al, ‘Synthesis of condensed tannins. Part 17. Oligomeric (2R,3S)-3,3′,4′,7,8-pentahydroxyflavans. Atropisomerism and conformation of biphenyl and m-terphenyl analogs from Prosopis glandulosa (‘mesquite’)’ J, Chem. Soc. Perkin I,(1986), (10), 1737-49. CA 107: 154106.

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