Drug – bio-affecting and body treating compositions – Plant material or plant extract of undetermined constitution...
Reexamination Certificate
2002-02-22
2002-09-17
Prats, Francisco (Department: 1651)
Drug, bio-affecting and body treating compositions
Plant material or plant extract of undetermined constitution...
C424S405000, C514S163000
Reexamination Certificate
active
06451356
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of Invention
This invention relates to the use of a compound 3,5-dihydroxy-4-pent-4′-enoyl-1′-oxymethylbenzoic acid (Oenostacin) isolated from the roots of the plant
Oenothera biennis
as an effective antibacterial agent active against bacteria such as staphylococci, streptococci and the like. The invention also provides pharmaceutical compositions comprising 3,5-dihydroxy-4-pent-4′-enoyl-1′-oxymethylbenzoic acid (Oenostacin) useful for treatment of skin infections such as endocarditis in humans caused by
Staphylococcus epidermidis.
2. Summary of the Related Art
The antimicrobial era has reached a point where the emergence of resistant microbes is accelerating while the pace of discovery of new drugs seems decelerating (
Science
157:1064-1073). Until recently, drugs or combination of drugs have not been able to overcome the problem of resistance. Few novel chemical entities have been brought to the market during the past decade to address this problem, as most of the new drugs are derivatives of older compounds. Many of these have increased activity or a broader spectrum of activity or improved pharmacological properties but can only temporarily overcome the problem of resistance. Thus, the isolation of natural products from sources such as various species of plants has become a basis for identifying new class of antimicrobial compounds. These compounds are being investigated for treatment of infections caused during seemingly uncomplicated hospital treatment procedures such as catheterization, insertion of intrauterine contraceptive devices and intravenous injections, for example.
Inflammation of the endocardium, i.e., the tissue lining of the cavities of the heart, is called endocarditis. Infective (infectious) endocarditis may be due to infection by a range of microorganisms such as Haemophilus sp.,
Staphylococcus aureus, Sepidermidis
(especially in patients with prosthetic valves),
Streptococcus faecalis, Neisseria gonorrhae
, Candida, etc. Infective endocarditis may be acute (e.g, when due to streptococci or gonococci) or sub-acute when due to viridans streptococci or fungi. Infection occurs through the circulatory system and organisms may gain access to the blood stream during dental treatment, catheterization, insertion of intrauterine contraceptive devices or intravenous injections, for example. The symptoms associated with such infections include fever, malaise, heart murmurs, weight loss, clubbing of fingertips and embolism. Late symptoms of sub-acute bacterial endocarditis include vasculitis, petechial rash and Osler's nodes. In addition, damage to heart valves may lead to heart failure. Endocarditis may also occur as a complication of other infectious diseases.
Oenothera biennis
(Onagraceae) is a genus of herbs and undershrubs distributed mainly in temperate America together with some species occurring in the tropics. Some of the species including
O. biennis
have been introduced into Indian Gardens (
J.Med.Arom Plant Sci
., 20:1998, 432). The oil from seeds of
O. biennis
(Evening Primrose) is known to be a rich dietary source of &ggr;-linolenic acid required for the formation of prostaglandins and related hormones (
Z Phytother
, 4:1983, 531). The seeds are reported to contain fatty acids (
J. Am Oil Chem Soc
, 61:1984, 540) and sterols (
Riv Ital Sastanze Grasse
, 53, 1976,25) while the leaves contain flavonoids (
Phytochemistry
, 6:1967, 317) and Oenothein A (
Chem Pharm Bull
, 39:1991, 1157). However, no compounds have been reported from the roots of
O.biennis
. Recently, certain specific activity is observed in the root extracts and this prompted a systematic activity-directed fractionation to isolate pure compounds. This systemic activity-directed fractionation of root extracts resulted in the identification of ten compounds, four of which are novel and reported in the
Indian Journal of Chemistry
, Vol. 38B, 1999, pages 705-708.
SUMMARY OF THE INVENTION
It is therefore an object of the invention to provide a compound that has potent activity as an antibacterial agent.
It is further an object of the invention to provide a pharmaceutical composition comprising a potent antibacterial agent.
Yet another object of the invention is to provide a method for the treatment of bacterial infections, especially diseases caused by bacteria.
Other objects and further scope of applicability of the present invention will become apparent from the detailed description given hereinafter. It should be understood, however, that the detailed description and specific examples, while indicating preferred embodiments of the invention, are given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.1
Accordingly, the present invention provides the compound 3,5-dihydroxy-4-pent-4′-enoyl-1′-oxymethylbenzoic acid (Oenostacin) as an antibacterial agent (
Indian Journal of Chemistry
, Vol. 38B, 1999, pages 705-708, incorporated herein by reference). This chemical compound has the molecular formula C
13
H
14
O
6
and the structural formula:
In a preferred embodiment, Oenostacin is active against streptococci and staphylococci, especially
Staphylococcus epidermidis
, which causes skin infections/endocarditis in humans. Hence, the present invention provides an antibiotic isolated from the roots of the plant
O. biennis
for use against
S. epidermidis
infection.
The invention further provides a pharmaceutical composition having antibacterial activity, comprising Oenostacin in combination, admixture, or associated with a pharmaceutically acceptable carrier, diluent or excipient thereof.
The invention also provides a method of treating a bacterial infection, and preferably a bacterial skin infection, comprising administering to a patient with such an infection an effective amount of Oenostacin.
DETAILED DESCRIPTION OF THE INVENTION
Accordingly, the invention provides a novel antibacterial composition comprising an effective amount of Oenostacin (3,5-dihydroxy-4-pent-4′-enoyl-1′-oxymethylbenzoic acid) obtained from the roots of
Oenothera biennis
in combination, admixture, or associated with a pharmaceutically acceptable carrier, diluent or excipient thereof.
In an embodiment of the invention, the 3,5-dihydroxy-4-pent-4′-enoyl-1′-oxymethylbenzoic acid is an extract obtained from the plant
Oenothera biennis
(
Indian Journal of Chemistry
, Vol. 38B, 1999, pages 705-708).
The concentration of Oenostacin in the composition is in the range of 1-200 &mgr;g/ml, or in the range of 10-90% by weight.
The antibacterial composition is effective against bacteria selected from streptococci, staphylococci and
Pseudomonas aeruginosa
, and preferably streptococci and staphylococci. The antibacterial composition may further be used for the treatment of endocarditis in humans. Acute endocarditis is an inflammatory disease of the endocardium i.e., the internal lining of the human heart and may be caused by the staphylococci and gonococoi bacteria, for example. Among staphylococci,
S.epidermidis
is one of the major etiological agents of this disease. The infections occur mainly in-patients with prosthetic valves.
Thus, the antibacterial composition may be used for the treatment of infections caused by
S. epidennidis.
Using a screening program aimed at detecting biomolecules from plant sources, which can specifically act against
S. epidermidis
, the present inventors have now discovered that the ethanolic extract derived from the roots of a plant called
O. biennis
contains the compound 3,5-dihydroxy-4-pent-4′-enoyl-1′-oxymethylbenzoic acid, which possesses antibacterial activity.
Oenothera biennis
is a genus of herbs and under-shrubs; its species mainly distributed in temperate America together with some species occurring in the tropics. Some of the species such as
O. biennis
have been introduced into the Indian gardens. The seeds of the
Gupta Vivek Kumar
Khanuja Suman Preet Singh
Kumar Sushil
Kumar Tiruppadiripuliyur Ranganathan Santha
Shukla Yogendra Nath
Coe Susan D.
Council of Scientific and Industrial Research
McDonnell & Boehnen Hulbert & Berghoff
Prats Francisco
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