Drug – bio-affecting and body treating compositions – Plant material or plant extract of undetermined constitution...
Reexamination Certificate
2001-03-30
2004-08-17
Minnifield, N. M. (Department: 1645)
Drug, bio-affecting and body treating compositions
Plant material or plant extract of undetermined constitution...
C424S727000, C424S750000, C424S757000, C514S002600, C514S008100, C514S012200, C514S023000, C514S024000, C514S025000, C514S183000, C536S004100
Reexamination Certificate
active
06777004
ABSTRACT:
FIELD OF INVENTION
The invention relates to a novel compound oleanane triterpenoid oligoglycoside of formula 1 of the accompanying drawing (trivially called corniculatonin). The invention also relates to a process for the isolation of the novel compound from a mangrove plant
Aegiceras corniculatum
(Blanco) belonging to the family Myrsinaceae. It also discloses the antifungal properties of the said compound. The invention further relates to the use of the said compound as a food preservative.
BACKGROUND OF INVENTION
Aspergillus sp. and many other moulds are often common contaminants of food, and effect the quality of the contaminated food by reducing starch and fat contents and lowering digestible energy level (William K. C., Blaney B. J. The potential of mould to reduce the value of foodstuffs. Proceeding of the aquaculture nutrition workshop. Allan G L, Dall W. Eds. Salmadar Bay, NSW-Australia. NSW. Fisher's 1992, 205-213). Aspergilli are known to occur on cereals, treenuts, peanuts, cotton, fruits, meat, poultry and sea food products (Jay J. M. 1978. Modem food microbiology, sec. Eds. D. Van Norstrand Company, New York.).
Aspergillus fresenii
and
A. niger
, used in the present investigation were found to be commonly associated with food products of wheat in coastal regions of India having warm and humid climate. The fungi from the genera Aspergillus are known to produce mycotoxins such as aflatoxins, fumronosins, fusaric acid, TA/AAL toxins, zearalenone, and trichothecene, 5-butyl picolinic acid and related phytotoxic pyridine derivatives. These mycotoxins are highly toxic to a variety of species including plants and humans and can be found in commercially prepared foodstuffs including milk and milk products, beans, cereals, sweet potatoes and commercially prepared animal feeds.
It is evident that new methods and formulations are needed to control plant and animal pathogens and the level of toxic metabolites present in consumable product and in the environment in general. The widespread use of pesticides, fungicides and chemical preservatives, however, has resulted in the development and evolution of resistant pathogens. As environment and health care concerns continue to mount, it will be necessary to identify or develop new fungicides to meet the environmental standards of the future. Particularly those, which are natural products for consumption by animals and thus have, low animal and environmental toxicities.
During the applicant's search for biologically active molecules from marine organism of Indian Ocean region, crude methanolic extract of a mangrove plant,
A. corniculatum
exhibited promising central nervous system depressant activity. In order to simplify the procedure for the isolation of the active principle, the crude extract was fractionated. The aqueous fraction being the major fraction, excess was left at room temperature. Surprisingly, it was observed that even on prolonged standing there was no fungal growth on the surface of the aqueous fraction. This indicated that the fraction must contain some molecule acting as antifungal agent. This observation coupled with the facts of increase in antibiotic resistant microbes and paucity of effective antifungals indicated a need for new antimycotic agents. It is with this goal in mind that the applicants studied the a aqueous fraction leading to the isolation of an active saponin.
Saponins are steroid or triterpenoid glycosides widely distributed in plants. The saponins have diverse biological activities finding use in agents employed as fungicides, insecticides, anticancer agents, cosmetics, food preservatives and fertilizers with growth promoting effects. Further use for saponins is in the removal of cholesterol from dairy products and as feed supplements for livestock such as chickens to reduce cholesterol levels in eggs.
A food preservative is containing saponin from aloe woods and p-hydroxy benzoic ester is disclosed in Japanese patent application no. 05009123. An antifungal drug containing saponin extracts from asparagus is described in Japanese patent application no. 2157205. The antimicrobial and pest activity of a saponin isolated from fruit pulp, tobacco and seed are described by Okunji et at. (Int. J. Crude Drug Res., 1990, 28:193-199); Gruenweller et al. (Phytochem., 1990, 29:2485-2490) and by Lalithat et al. (Int. Pest Control, 1988, 30:42-45) respectively. U.S. Pat. No. 4,477,361 (Sperti G. S. et al., 1984) describes a cinnamic compound containing an antimicrobial surfactant which is rendered substantive to the surface being washed. Film forming and/or anti-transpirants coating polymers such as NaHCO3 and light paraffinic petroleum oils have been reported to control the level of fungal colonization (Horst. et al. Plant Disease, 1992, 247-251; Elad et al. Phytoparasitica, 1989, 17:279-288 and Ziv, et al. Hort. Science, 1993,124).
Triterpene sapogenins from the bark of
Aegiceras majus
(Gaerten) (Syn.
Aegiceras corniculatum
) have been investigated by Rao and Bose, who initially reported isolation of aegiceradienol (Science and Culture, 1958, 24:486), genin A (Rao K. V. et al., J. Ind. Chem. Soc., 1959, 36:358); aegiceradiol (Rao K. V. et al., Tetrahedron, 1962, 18:461) and norechinocystadienol (Rao K. V. et al., J. Org. Chem., 1962, 27:1470) as products of usual acid hydrolysis of saponin mixture. Aegicerin (Rao K. V., Tetrahedron, 1964, 20:973) is reported to be present in the non-glycosidic extract of the bark of
A. majus
(Gaerten). Later on Hensens and Lewis (Henses O. D. et al., Tetrahedron letters, 1965, 4639) demonstrated that aegicerdiol or aegiceradienol are artifacts formed during the usual fairly vigorous hydrolysis conditions used for the crude glycosides mixture.
Isorhamnetin, echinocystic acid and rapanone are also known to be constituents of
Aegiceras corniculatum
(Henses O. D. et al., Aust J. Chem., 1966, 19:169). This mangrove is known to photosynthesize aspartate and alanine as major products of short time photosynthesis (Bhosale L. et al., Photosynthetica, 1983, 17:59). Payne reports the presence of fish toxin, 5-O-methyl embelin in this mangrove (Payne A. M., Diss. Abst. Int. PT. B. Sci. and Eng. 1991, 51:225). Chattopadhyay et al, (Chattopadhyay S. et al., Proceedings of the National Symposium on Marine Resources, Techniques, Evaluation and Management; Vaidyanadhan R. et al., eds., 1990, 5-7) found lupeol, amyrin, oleanolic acid and ursolic acid besides campesterol, stigmasterol and sitosterol, to be the major triterpenoids and steroids respectively. Saponin fraction of
Anagallis arvensis
is antiviral being effective against Herpes simplex virus type I and polio virus (Amoros M et al., Ann. Pharm. Fr., 1977, 35:371; PI. Med. Phytoh., 1979, 13:122 and Amoros M. et al., Phytochem, 1987, 26:787). Its crude glycoside, Heteroside I, wherein anagalligenone is the constituent genin is reported to be antifungal and to inhibit germination of linseed. Its LD
50
in mice was 675 mg/Kg per os and 30.4 mg/Kg by s.c. (Staron T. et al., Phytiat-Phytopharm, 1969, 18:161). The saikosaponins of
Bupleurum falcatum
, a crude drug in oriental medicine for treatment of hepatobiliary and anti-inflammatory diseases, have shown several metabolic actions in rat, in addition to anti-inflammatory action (Yamamoto M. et al., Arzneim Forsch, 1975, 25:1021,1240).
A comparative study of saikosaponins of
Bupleurum longeradiatum
var.
breviradiatum
and
B. falcatum
showed that per os administration of 1.0-3.0 g/Kg of the saponin was non toxic and the analgesic effect of the former was twice that of later. Both (500 mg/Kg os) prolonged sleeping time produced by hexabarbital sodium in mice (Imaoka, I. et al., Shioku Igaku Zasshi, 1970, 26:1; Chem. Abstr., 1970, 73:43769).
Sakurasaponin from
Rapanea melanophloeos
(L.) Mez (Myrsinaceae) exhibits molluscidal at 3 ppm and antifungal against plant pathogenic fungus
Cladosporium cucumerinum
at 1 &mgr;g in TLC bioassay (Ohtani Kazuhiro et al., Phytochem, 1993, 33:83).
OBJECTS OF THE INVENTION
The main object of the present invention is to pr
Bhosak Siddharth Hariba
D'Souza Maria Lisette De Lumen
Wahidullah Solimabi
Council of Scientific & Industrial Research
McDonnell & Boehnen Hulbert & Berghoff
Minnifield N. M.
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