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|||||||||||III US005431924A United States Patent (19) 11 Patent Number: 5,431,924 Ghosh Et Al |||||||||||III US005431924A United States Patent (19) 11 Patent Number: 5,431,924 Ghosh et al. 45) Date of Patent: Jul. 11, 1995 (54) ANTI-INFLAMMATORY COMPOSITION J. F. Blair “South Westerners Grow Emu, & Then DERVED FROM EMU OL Exotic Animals 'Feedstuffs Jan. 28, 1990, p. 31. O'Brien, et al., Proc. Aust. Soc Animal Prod. 18: 75) Inventors: Peter Ghosh, Fairlight; Michael 101-111, 1990. Whitehouse, Millswood; Michael Bennett, George, "Observations Pricipally on the Ani Dawson, Newton; Athol G. Turner, mal and Vegetable Productions of New South Wales, Forestville, all of Australia New Zealand,” Gatherings of a Naturalist in Australasia, published London: John Van Voorst, Paternoster Row, 73) Assignee: Emu Products Western Australia Pty. pp. 216-219 (1860). Ltd., Claremont, Australia Leichhardt, L., “Journals, Lost and Found,’ Journal of 21) Appl. No.: 50,423 an Overland Expedition in Australia, published London: T. W. Boone, pp. 388-389 (1847). 22) PCT Filed: Nov. 14, 1991 Naughton, Joan M., et al., "Animal Foods in Tradi tional Australian Aboriginal Diets: Polyunsaturated and 86) PCT No.: PCT/AU91/00517 Low in Fat,” Lipids 21(11):684-690 (1986). “Notes on the Field Sports and Fauna of Australia S371 Date: Jul. 16, 1993 Felix,” Bush Wanderings of a Naturalist, by an Old S 102(e) Date: Jul. 16, 1993 Bushman, published London: Routledge, Warne & Routledge (1861). 87). PCT Pub. No.: WO92/08470 "Emu oil called a miracle,” Sun p. 7 (Apr. 16, 1990. PCT Pub. Date: May 29, 1992 Primary Examiner-John W. Rollins 30) Foreign Application Priority Data Attorney, Agent, or Firm-Patrea L. Pabst Nov. 14, 1990 AU) Australia .............................. PK3363 57 ABSTRACT A biologically active component of emu oil is disclosed 51 Int. Cl'.............................................. A61K 47/00 which is useful in pharmaceutical composition for the 52 U.S. C. ..................................... 424/522; 514/825 treatment of inflammation of environmental and sys 58 Field of Search ......................... 424/522; 514/825 temic origins. Pharmaceutical composition including emu oil and dermal transport enhancing compounds are (56) References Cited also disclosed as useful topical anti-inflammatory treat PUBLICATIONS ments. Pat. Abst of Japan C-20 p. 21 JP.A, 55-66514 (Sakurama)-May 5, 1988. 17 Claims, 1 Drawing Sheet U.S. Patent July 11, 1995 5,431,924 A/G 7 1OO 8O 6 O 4 O 2O O . - 1 1O 1OO ConCentration Of Oil (% Wv x 10-?) Inhibition of human granulocyte elastase by EMU OIL preparations (H.G.E. 5O ng). -o- EMU OIL (Acetone fractionated -O- EMU OIL (BOfCh 67) -- EMU Ol. (BotCh 181) 5,431,924 1 2 thetic precursor of the the anti-inflammatory prosta ANTI-NFLAMMATORY COMPOSITION glandin E1 (PGE) (6). DERVED FROM EMU OIL Evening primrose oil is also a rich source of gamma linolenic acid (7) and has been demonstrated to suppress FIELD OF THE INVENTION chronic adjuvant induced polyarthritis in the rat (6) as This invention relates to compositions for topical well as in patients with rheumatoid arthritis (8). application that are useful for the treatment of musculo There have been limited studies on the effects of skeletal and dermatological conditions, in particular to administering these C18 unsaturated fatty acids topi composition based on emu oil and compounds that act cally for the treatment of inflammatory conditions. to provide for its effective transdermal transport. 10 In PCT/AU89/00555 (WO 90/07331) it is disclosed The invention further relates to methods for the treat that linseed oil and other plant derived oils, which con ment of the aforementioned conditions using these com tain alpha linolenic acid, when dispersed in an appropri positions. ate solvent or thinner display topical anti-inflammatory The invention still further relates to compounds de activity. The specification goes on to disclose that the rived from emu oil which have anti-inflammatory prop 15 activity of this composition is thought to arise due to its erties. alpha linolenic acid (9, 15, 15, octadecatrienoic acid) For the purposes of this specification, the term "emu content. Suitable thinners, which in the context of the oil” refers to oils and preparations of oils derived from application mean compounds for increasing the trans the emu (Dromais Novae-Hollandiae). dermal transport of linseed oil, are said to be mineral or distilled turpentine, methylethyl- and isopropylsalicy BACKGROUND ART late esters, eucalyptol (cineole) tea tree oil and oil of Within recent years there has been considerable inter wintergreen. These thinners in combination with the est in the role of the ingestion of polyunsaturated fatty linseed oil are stated to exhibit synergism and a surpris acids in the prevention or treatment of arthritis, soft ing anti-inflammatory effect. tissue inflammation and cardiovascular disease. This 25 interest has arisen from the observation that Greenland BRIEF DESCRIPTION OF THE DRAWING Eskimos, on a traditional native diet, showed disease FIG. 1 is a graph showing the inhibition of human patterns quite different from age-matched individuals in granulocyte elastase by EMU OIL preparations Europe and North America. The most striking differ ences observed were the reduced incidence of heart 30 (H.G.E. 50 ng). The percent inhibition is compared to disease, asthma, psoriasis and rheumatoid arthritis in the concentration of oil (% weight/volume X 10-2). Eskimo populations (1). The darkened circles represent EMU OIL (acetone Examination of the Eskimo dietary lipid intake fractionated). The open circles represent EMU OIL showed elevated levels of highly unsaturated fatty acids (Batch 67). The darkened squares represent EMU OIL (HUFAs) arising from their high consumption of fish 35 (Batch 181). and marine, mammals. Subsequent clinical trials initi DISCLOSURE OF THE INVENTION ated by Kremer and co-workers (2) have demonstrated that the manipulation of the dietary intake offatty acids The present inventors in their investigation of emu oil to include higher levels of HUFAs in caucasian patients sought to determine if this animal oil had any anti-in with rheumatoid arthritis could decrease the symptoms flammatory, anti-proteolytic or sun protective activity. of arthritis. Oils extracted or rendered from emu body fats are The mechanism of action of this dietary intervention known to contain triglyceride esters of long chain fatty was considered, in part, to be dependent on the ability acids including oleic acid and linoleic acid as well as the of the HUFAs to act as competitive substrates for en saturated fatty acids, palmitic and stearic (9). zymes involved in prostaglandin and leukotriene bio 45 It was found that whilst potent anti-proteolytic activ synthesis. Eicosapentaenoic acid (EPA) (20:5, n=3) ity could be demonstrated for emu oil against purified and docosahexaenoic acid (22:6, n=3) are the principle human granulocyte elastase using appropriate in vitro long chain unsaturated fatty acid triglycerides in fish assays, as shown in FIG. 1, when the oil was applied oil. EPA incorporated into cell membranes may be topically to the dorsal skin of rats in which a polyarthri converted via the cyclooxygenase enzymes into the 50 tis was induced by the injection into the tail base of a regulant prostaglandins, thromboxanes and prostacy mixture of M. tuberculosis (500 ug) and squalene (500 clins of the 3-series (2-5) whereas PGE2 produced from uL), there was no reduction in the inflammatory reac arachidonic acid precursors was a potent mediator of tion, as determined by a decrease in the swelling (oe inflammation. EPA metabolised via the lipoxygenase dema) of the animal's paws. On the other hand, if to the pathway produces leukotriene B5 (2-5). Leukotriene B5 55 emu oil was added a miscible diluent such as isopropyl is 10-30 times less potent an inflammogen than leuko alcohol, amyl alcohol or acetate, ethyl, methyl or iso triene B4 which is normally produced from arachidonic propylsalicylate, tea tree oil, eucalyptus oil, cineole or acid. Thus dietary fish oil supplementation may support the like and the mixture applied to the skin of the rats, endogenous anti-inflammatory activity by modifying potent anti-inflammatory activity was observed, as is the production of harmful mediators within the animal's shown in Tables 1-4 and 7-10. tissues. However, when the anti-inflammatory emu oil An alternative pathway of unsaturated fatty acid batches used in these experiments were analysed by metabolism is via the C18-triunsaturated fatty acids, GLC and GLC-mass spectroscopy using purified fatty gamma and alpha linolenic acid. While the alpha isomer acids of known structures as standards (Tables 5 and 6) (9, 12, 15 octadecatrienoic acid) may be shunted into the 65 it was found that apart from three batches (157,203 and prostaglandin E3 pathway, gamma linolenic acid (6, 9, 988) none of the oils contained detectable levels of 12 octadecatrienoic acid) is converted into dihomo gamma or alpha linolenic acid. This was somewhat gamma-linolenic acid (DGLA) which is the biosyn surprising in view of the disclosure of WO90/07331. 5,431,924 3 4. This finding led to the conclusion that the observed even if these triglycerides are not absorbed and remain anti-inflammatory activity of emu oils, when combined associated with the skin, the potent anti-elastase activity with a diluent which improved transdermal absorption, demonstrated to be present in the emu oil (FIG. 1), was unrelated to the polyunsaturated fatty acid content which probably arises from its high oleic acid content of the emu oil. (11, 12) could provide a local anti-inflammatory as well This hypothesis was tested by examining various as antidegenerative effect to dermal tissues. This could plant oils known to be rich in gamma and alpha linole be particularly relevant during dermal inflammation nic acid in the same animal arthritis model as used for where cell and tissue damage produced by exposure to the emu oil experiments.
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