WO2000074663A2 - Use of allicin for control of weight in mammals - Google Patents
Use of allicin for control of weight in mammals Download PDFInfo
- Publication number
- WO2000074663A2 WO2000074663A2 PCT/IL2000/000323 IL0000323W WO0074663A2 WO 2000074663 A2 WO2000074663 A2 WO 2000074663A2 IL 0000323 W IL0000323 W IL 0000323W WO 0074663 A2 WO0074663 A2 WO 0074663A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- allicin
- weight
- pharmaceutical composition
- prevention
- fructose
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
- A61K31/198—Alpha-aminoacids, e.g. alanine, edetic acids [EDTA]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
Definitions
- the present invention relates to compositions comprising allicin and to methods for reduction of weight and/or for prevention of weight gain in mammals, particularly in humans.
- Garlic and garlic preparations commercially available in the form of garlic oil, extracts, pills or tablets are widely used for some therapeutic purposes including lowering blood pressure, although their therapeutic effect is still questionable.
- preparation procedures of such garlic preparations are unknown and the composition and amount of their active ingredients are not defined making difficult the proper evaluation of their therapeutic effect.
- allicin thio-2-propene-l-sulf ⁇ nic acid S-allyl ester
- Allicin is not present as such in the intact garlic clove, but is produced together with pyruvate and ammonia from the odorless precursor alliin (+)(S-allyl-L-cysteine sulfoxide) in the presence of the enzyme alliinase [E.C. 4.4.1.4.]. Alliin and alliinase are found in different compartments of the garlic clove. The cutting or crushing of the clove enables the enzyme to come into contact with the precursor thus producing allicin.
- alliinase is a so-called "suicidal enzyme", that is rapidly and irreversibly inactivated by its own reaction product, allicin.
- incubation for a few minutes of alliinase with the substrate alliin or its product, allicin leads to a biologically inactive enzyme after one or a very limited number of cycles.
- This problem has recently been solved by the inventors by the method described in PCT Publication No. WO 97/39115 (Mirelman et al., 1997), whereby continuous production of substantially pure allicin is provided by adding the substrate alliin to a column comprising immobilized garlic alliinase.
- allicin is also effective in control of weight in mammals.
- the present invention thus relates to compositions comprising allicin for control of weight in mammals, both for human and veterinary use.
- the invention provides pharmaceutical compositions for reduction of weight and/or prevention of weight gain in humans, and more particularly in individuals which have undergone a diet for reducing weight.
- the pharmaceutical composition of the invention may be presented in any suitable form of administration as well known for the artisans in the art, Preferably, the composition is in a form for oral administration, for example, an aqueous solution of allicin or allicin adsorbed in a pharmaceutically acceptable polymer, e.g. a natural polysaccharide such as, but not being limited to, cellulose, starch, dextran, agar, agarose, alginic acid, guar and the like.
- a pharmaceutically acceptable polymer e.g. a natural polysaccharide such as, but not being limited to, cellulose, starch, dextran, agar, agarose, alginic acid, guar and the like.
- allicin to be used according to the invention will depend on the individual to be treated - the sex and age of the patient, his/her health condition and weight before treatment, and can be easily determined by physicians as necessary.
- the composition may be in the form of a prodrug consisting of suitable forms of alliin and alliinase that will produce allicin in situ after ingestion.
- the alliinase natural or recombinant, may be in soluble or insoluble form, for example, it may be chemically, physically or biologically immobilized on a solid support as described in published PCT Publication No. WO 97/39115, herein incorporated by reference as if fully described herein.
- alliinase is chemically coupled to Cl-Sepharose as described in WO 97/39115.
- the invention relates to the use of allicin for the preparation of a pharmaceutical composition for reduction of weight and/or prevention of weight gain.
- the invention relates to a method for reduction of weight and/or prevention of weight gain which comprises administering to an individual in need thereof an effective amount of allicin.
- Fig. 1 shows the average body weight of 8 rats, initially and after receiving fructose diet for 3 and 5 weeks.
- Fig. 2 shows the average body weight of 7 rats, initially and after receiving fructose diet for 3 weeks and then fructose + allicin (8 mg/kg/day) for another 2 weeks.
- Fig. 3 shows the average body weight of 5 rats, initially and after receiving fructose diet + allicin (8 mg/kg/day) for 3 weeks and then fructose only for another 2 weeks.
- Fig. 4 shows the average body weight of 8 rats, initially and after receiving fructose diet for 3 weeks and then fructose + trandolapril (0.1 mg/kg/day) for another 2 weeks.
- Fig. 5 shows the average body weight of 10 rats, initially and after receiving fructose diet for 3 weeks and then fructose + enalapril (20 mg/kg/day) for another 2 weeks.
- mice Male Sprague-Dawley rats, 8 per group, initially weighing 240-250 g, were fed a fructose-enriched diet which consisted of 21% protein, 5% fat, 60% carbohydrate, 0.49%o sodium and 0.49% potassium, for 5 weeks, which produced hyperinsulinemia, hypertension and hypertriglyceridemia. Animals were divided into 5 groups:
- Enalapril (20mg/kg/day) added during the last 2 weeks. Both trandolapril and enalapril are known ACEI inhibitors used for treatment of arterial hypertension.
- rats after a 3 -week fructose-enriched diet had their weight raised from 259.1+9.6 g to 292.2 ⁇ 12.6 g, and their weight remained fairly steady when administered fructose+allicin during the following 2 weeks (group II, 7 rats), reaching 282.4 ⁇ 17.4 g.
- rats that received a fructose-enriched diet for 3 weeks had their weight raised from 229.8+3.8 g at the baseline to 330.2 ⁇ 15.5 g after 3 weeks, and then after receiving fructose + trandolapril group (group IV, 8 rats) for another 2 weeks had their weight raised to 355.1 ⁇ 20.0 g at the end of the 5 th week. Similar results were obtained with rats fed fructose for 3 weeks and then fructose + enalapril group (group V, 10 rats) for another 2 weeks (Fig. 5).
Abstract
Allicin is used for control of weight in mammals, in particular for reduction of weight and/or prevention of weight gain, more particularly for prevention of weight gain in an individual who has previously undergone a diet for reducing weight.
Description
USE OF ALLICIN FOR CONTROL OF WEIGHT IN MAMMALS
FIELD OF THE INVENTION
The present invention relates to compositions comprising allicin and to methods for reduction of weight and/or for prevention of weight gain in mammals, particularly in humans.
BACKGROUND OF THE INVENTION
Garlic and garlic preparations commercially available in the form of garlic oil, extracts, pills or tablets are widely used for some therapeutic purposes including lowering blood pressure, although their therapeutic effect is still questionable. Usually the preparation procedures of such garlic preparations are unknown and the composition and amount of their active ingredients are not defined making difficult the proper evaluation of their therapeutic effect. Nevertheless, some studies reported the beneficial effects of garlic on cardiovascular risk factors, mainly hyperlipidemia and thrombogenesis in animals and in humans. Thus, administration of fresh garlic or etheric garlic extracts was shown to induce an increase in fibrinolytic activity (Bordia et al., 1977; Kieswetter et al., 1990), to inhibit platelet aggregation (Makheja and Bailey, 1990), to protect cholesterol- fed rabbits against the onset of atherosclerosis (Efendy et al., 1997), and to improve lipid profile including reduction of serum cholesterol levels (Bordia and Verma, 1980; Bordia et al, 1975; Knipschild and Ter-Riet, 1989; Augusti and Mathew, 1974). These studies demonstrated a very impressive effect of garlic, but most studies were limited by several factors such as lack of controlled methods and suitable double-blind studies and use of preparations with unknown amount and chemical identification of the active ingredient. Among the active principles present in garlic, the principal component is allicin (thio-2-propene-l-sulfιnic acid S-allyl ester), a chemically unstable,
colorless liquid that is thought to be responsible for both the odor and much of the biological activity of garlic. Allicin is not present as such in the intact garlic clove, but is produced together with pyruvate and ammonia from the odorless precursor alliin (+)(S-allyl-L-cysteine sulfoxide) in the presence of the enzyme alliinase [E.C. 4.4.1.4.]. Alliin and alliinase are found in different compartments of the garlic clove. The cutting or crushing of the clove enables the enzyme to come into contact with the precursor thus producing allicin.
Allicin was shown to exhibit the beneficial properties ascribed to garlic (Eilat et al., 1995; Elkayam et al., 1999) but its use as the active ingredient of pharmaceutical compositions has not been made possible for lack of suitable methods for its production in stable and purified form. The chemical synthesis involves many steps and is complicated, laborious, expensive, and very inefficient.
The enzymatic method for the preparation of allicin is more attractive.
However, alliinase is a so-called "suicidal enzyme", that is rapidly and irreversibly inactivated by its own reaction product, allicin. Thus, incubation for a few minutes of alliinase with the substrate alliin or its product, allicin, leads to a biologically inactive enzyme after one or a very limited number of cycles. This problem has recently been solved by the inventors by the method described in PCT Publication No. WO 97/39115 (Mirelman et al., 1997), whereby continuous production of substantially pure allicin is provided by adding the substrate alliin to a column comprising immobilized garlic alliinase.
SUMMARY OF THE INVENTION
It has now been found, according to the present invention, that allicin is also effective in control of weight in mammals.
The present invention thus relates to compositions comprising allicin for control of weight in mammals, both for human and veterinary use. In particular, the invention provides pharmaceutical compositions for reduction of weight and/or prevention of weight gain in humans, and more particularly in individuals which have undergone a diet for reducing weight.
The pharmaceutical composition of the invention may be presented in any suitable form of administration as well known for the artisans in the art, Preferably, the composition is in a form for oral administration, for example, an aqueous solution of allicin or allicin adsorbed in a pharmaceutically acceptable polymer, e.g. a natural polysaccharide such as, but not being limited to, cellulose, starch, dextran, agar, agarose, alginic acid, guar and the like. These compositions may be prepared by mixing and spray drying the ingredients and incorporating the resulting powder into capsules by standard techniques.
The amounts of allicin to be used according to the invention will depend on the individual to be treated - the sex and age of the patient, his/her health condition and weight before treatment, and can be easily determined by physicians as necessary.
Alternatively, the composition may be in the form of a prodrug consisting of suitable forms of alliin and alliinase that will produce allicin in situ after ingestion. The alliinase, natural or recombinant, may be in soluble or insoluble form, for example, it may be chemically, physically or biologically immobilized on a solid support as described in published PCT Publication No. WO 97/39115, herein incorporated by reference as if fully described herein. In one preferred embodiment, alliinase is chemically coupled to Cl-Sepharose as described in WO 97/39115.
In another aspect, the invention relates to the use of allicin for the preparation of a pharmaceutical composition for reduction of weight and/or prevention of weight gain.
In still another aspect, the invention relates to a method for reduction of weight and/or prevention of weight gain which comprises administering to an individual in need thereof an effective amount of allicin.
BRIEF DESCRIPTION OF THE DRAWINGS
Fig. 1 shows the average body weight of 8 rats, initially and after receiving fructose diet for 3 and 5 weeks.
Fig. 2 shows the average body weight of 7 rats, initially and after receiving fructose diet for 3 weeks and then fructose + allicin (8 mg/kg/day) for another 2 weeks.
Fig. 3 shows the average body weight of 5 rats, initially and after receiving fructose diet + allicin (8 mg/kg/day) for 3 weeks and then fructose only for another 2 weeks.
Fig. 4 shows the average body weight of 8 rats, initially and after receiving fructose diet for 3 weeks and then fructose + trandolapril (0.1 mg/kg/day) for another 2 weeks. Fig. 5 shows the average body weight of 10 rats, initially and after receiving fructose diet for 3 weeks and then fructose + enalapril (20 mg/kg/day) for another 2 weeks.
DETAILED DESCRIPTION OF THE INVENTION The invention will be illustrated according to the following non-limiting
Example with reference to the drawings.
EXAMPLE. Allicin prevents weight gain in rats on a fructose-enriched diet
Materials and Methods
(a) Pure allicin was produced by interaction of the synthetic substrate alliin with purified alliinase isolated from garlic cloves as described previously in PCT Publication No. WO 97/39115 (Mirelman et al, 1997). Fructose was purchased from Harlan, Teklad (Madison, WI, USA). Sprague-Dawley rats were purchased from ANILAB, Tal-Shahar, Israel.
(b) Experiments were carried out on Reaven's rat model, according to which Sprague-Dawley rats become insulin-resistant, hyperinsulinemic, hypertriglyceridemic and hypertensive when fed a fructose-enriched diet (Reaven, 1991). This model was previously used by the inventors to test the effect of different angiotensin-converting enzyme inhibitors (ACEI), namely enalapril,
ramipril and lisinopril, on metabolic parameters and hypertension in said rats, and enalapril was found to have the most beneficial effect on all parameters (Erlich and Rosenthal, 1995).
Experimental
Male Sprague-Dawley rats, 8 per group, initially weighing 240-250 g, were fed a fructose-enriched diet which consisted of 21% protein, 5% fat, 60% carbohydrate, 0.49%o sodium and 0.49% potassium, for 5 weeks, which produced hyperinsulinemia, hypertension and hypertriglyceridemia. Animals were divided into 5 groups:
I. Fructose only (control group).
II. Allicin (8mg/kg/day) added daily during the last 2 weeks.
III. Allicin (8mg/kg/day) given during the first 3 weeks of fructose-rich diet. IV. Trandolapril (0.1 mg/kg/day) added during the last 2 weeks.
V. Enalapril (20mg/kg/day) added during the last 2 weeks. Both trandolapril and enalapril are known ACEI inhibitors used for treatment of arterial hypertension.
Weight was measured at the beginning of the experiment and after 3 and 5 weeks on the diet. The same amount of food was consumed by all 5 study groups. As shown in Fig. 1, rats on a diet of fructose only (group I, 8 rats - control group) had their weight raised from 233.5+8.0 g to 329.6±28.8 g after 3 weeks, and at the end of 5 weeks to 376.1±38.4 g.
As shown in Fig. 2, rats after a 3 -week fructose-enriched diet had their weight raised from 259.1+9.6 g to 292.2±12.6 g, and their weight remained fairly steady when administered fructose+allicin during the following 2 weeks (group II, 7 rats), reaching 282.4±17.4 g.
When the protocol was reversed and the animals were given fructose and allicin concomitantly for 3 weeks and then fructose alone for another 2 weeks (group III, 5 rats), their weight remained steady: 262.2±18.4 g at baseline,
273±14.7 g after 3 weeks on fructose/allicin and 263±24.2 g after 2 more weeks on fructose alone (Fig. 3).
As shown in Fig. 4, rats that received a fructose-enriched diet for 3 weeks had their weight raised from 229.8+3.8 g at the baseline to 330.2±15.5 g after 3 weeks, and then after receiving fructose + trandolapril group (group IV, 8 rats) for another 2 weeks had their weight raised to 355.1±20.0 g at the end of the 5th week. Similar results were obtained with rats fed fructose for 3 weeks and then fructose + enalapril group (group V, 10 rats) for another 2 weeks (Fig. 5).
The results above clearly show that both the control and trandolapril/enalapril groups continued to gain weight (Figs. 1, 4, 5), while the allicin groups did not (Figs. 2, 3).
REFERENCES
1. Augusti, K.T. and Mathew, P.T. (1974) Lipid lowering effect of allicin (diallyl disulphide oxide) on long term feeding to normal rats. Experientia 30: 468-470.
2. Bordia, A., Arora, S.K., Kothari, L.K., Jain, K.C., Rathore, B.S. and Rathore, A.S. (1975) The protective action of essential oils of onion and garlic in cholesterol- fed rabbits. Atherosclerosis 22: 103-109.
3. Bordia, A.K., Sanadhya, J.Y.K. and Bhu, N. (1977) Effect of essential oil of garlic on serum fibrinolytic activity in patients with coronary artery disease. Atherosclerosis 28: 155-159.
4. Bordia, A. and Verma S.A. (1980) Effect of garlic feeding on regression of experimental atherosclerosis in rabbits. Artery 7: 428-437.
5. Efendy, J.L., Simmons, D.L., Campbell, G.R. and Campbell, J.H. (1997) The effect of the aged garlic extract, 'Kyolic', on the development of experimental atherosclerosis. Atherosclerosis. 132: 37-42.
6. Eilat, S., Oestraicher, Y., Rabinkov, A., Ohad, D., Mirelman, D., Baitler, A., Eldar, N., and Vered, Z. (1995) Alteration of lipid profile in hyperlipidemic rabbits by allicin, an active constituent of garlic. Coronary Artery Dis. 6: 985-990.
7. Elkayam, A., Mirelman, D., Peleg, E., Wilchek, M., Miron, T., Rabinkov, A., Sadetzki, T. and Rosenthal, T. (1999) Comparison of the effect of allicin and enalapril on blood pressure, insulin and triglycerides levels in fructose-induced hyperinsulinemic-hyperlipidemic- hypertensive rats. J. Hypertension (in press).
8. Erlich Y. and Rosenthal T. (1995) Effect of angiotensin-converting enzyme inhibitors on fructose-induced hypertension and hyperinsulinemia in rats. Clin Exp Pharmacol Physiol 27 (Suppl 1); S347-S349.
9. Kieswetter, H., Jung, F., Morwietz, C, Pindur, G., Heiden, M. and Wenzel, E. (1990) Effect of garlic on blood fluidity and fibrinolytic activity: A randomised placebo-controlled double-blind study. Brit. J. Clin. Pract. Suppl. 69: 24-29.
10. Knipschild, J.K. and Ter-Riet, G. (1989) Garlic, onions and cardiovascular risk factors. A review of the evidence from human experiments. Emphasis on commercially available preparations. Brit. J. Clin. Pharmacol. 28: 535-544.
11. Makheja, A.N. and Bailey, J.N. (1990) Agents Actions 29: 360-363.
12. Mirelman, D. et al. (1997) PCT Publication No. WO 97/39115.
13. Reaven, G.M. (1991) Insulin resistance, hyperisulinemia and hypertriglyceridemia in the etiology and clinical course of hypertension. Amer. J. Med. 90 (Suppl. 2A): 7-12.
Claims
1. A pharmaceutical composition for control of weight in mammals comprising allicin and a pharmaceutically acceptable carrier.
2. The pharmaceutical composition according to claim 1, for reduction of weight.
3. The pharmaceutical composition according to claim 1, for prevention of weight gain.
4. The pharmaceutical composition according to claim 3, for prevention of weight gain in individuals which have undergone a diet for reducing weight.
5. The pharmaceutical composition according to any one of claims 1 to 4, for oral administration.
6. The pharmaceutical composition according to any one of claims 1 to 5, wherein allicin is provided in the form of a prodrug consisting of suitable forms of alliin and alliinase.
7. The pharmaceutical composition according to claim 6, wherein the alliinase is immobilized on a solid support.
8. Use of allicin for the preparation of a pharmaceutical composition for control of weight in mammals.
9. The use according to claim 8, for reduction of weight.
10. The use according to claim 8, for prevention of weight gain.
11. The use according to claim 10, wherein said pharmaceutical composition is for prevention of weight gain in individuals which have undergone a diet for reducing weight.
12. The use according to any one of claims 8 to 11, wherein the composition is for oral administration.
13. The use according to any one of claims 8 to 11, wherein allicin is provided in the form of a prodrug consisting of suitable forms of alliin and alliinase.
14. The use according to claim 13, wherein the alliinase is immobilized on a solid support.
15. A method for controlling weight which comprises administering to an individual in need thereof an effective amount of allicin.
16. A method according to claim 15 wherein allicin is administered for reduction of weight gain.
17. A method according to claim 15 wherein allicin is administered for prevention of weight gain.
18. The method according to claim 17, for prevention of weight gain in an individual who has previously undergone a diet for reducing weight.
19. The method according to any one of claims 15 to 18, wherein allicin is administered orally.
20. The method according to any one of claims 15 to 19, wherein allicin is provided in the form of a prodrug consisting of suitable forms of alliin and alliinase.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU49474/00A AU4947400A (en) | 1999-06-07 | 2000-06-05 | Use of allicin for control of weight in mammals |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL13032599A IL130325A0 (en) | 1999-06-07 | 1999-06-07 | Pharmaceutical compositions comprising allicin |
| IL130325 | 1999-06-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2000074663A2 true WO2000074663A2 (en) | 2000-12-14 |
| WO2000074663A3 WO2000074663A3 (en) | 2001-08-02 |
Family
ID=11072889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IL2000/000323 WO2000074663A2 (en) | 1999-06-07 | 2000-06-05 | Use of allicin for control of weight in mammals |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU4947400A (en) |
| IL (1) | IL130325A0 (en) |
| WO (1) | WO2000074663A2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7157422B2 (en) | 2000-01-03 | 2007-01-02 | Tel Aviv University Future Technology Development L.P. | Glycogen synthase kinase-3 inhibitors |
| EP1890693A2 (en) * | 2005-06-13 | 2008-02-27 | Yeda Research And Development Co., Ltd. | Use of allylmercaptocaptopril for treating or preventing obesity and obesity related diseases |
| US7378432B2 (en) | 2001-09-14 | 2008-05-27 | Tel Aviv University Future Technology Development L.P. | Glycogen synthase kinase-3 inhibitors |
| CN100389760C (en) * | 2006-04-18 | 2008-05-28 | 张国清 | Enteric coated drop pills of garlicin, and preparation method |
| US7446092B2 (en) | 2002-12-12 | 2008-11-04 | Tel Aviv University Future Technology Development L.P. | Glycogen synthase kinase-3 inhibitors |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0232501A1 (en) * | 1985-12-19 | 1987-08-19 | Chimicasa Gmbh | Pharmaceutical preparation for the treatment of lipid metabolism disorders (hyperlipoproteinemia) |
| WO1997039115A1 (en) * | 1996-04-16 | 1997-10-23 | Yeda Research And Development Co. Ltd. | Immobilized alliinase and continuous production of allicin |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6261925A (en) * | 1985-09-10 | 1987-03-18 | Riken Kagaku Kogyo Kk | Lipid metabolism promoting agent |
| JPH04338336A (en) * | 1991-05-15 | 1992-11-25 | Riken Health Kk | Antiobesitic agent |
| JPH05268906A (en) * | 1991-09-17 | 1993-10-19 | Michiyasu Hamaya | Health food |
| JPH07304683A (en) * | 1994-05-09 | 1995-11-21 | Riken Health Kk | Lipid metabolism-promoting agent |
-
1999
- 1999-06-07 IL IL13032599A patent/IL130325A0/en unknown
-
2000
- 2000-06-05 AU AU49474/00A patent/AU4947400A/en not_active Abandoned
- 2000-06-05 WO PCT/IL2000/000323 patent/WO2000074663A2/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0232501A1 (en) * | 1985-12-19 | 1987-08-19 | Chimicasa Gmbh | Pharmaceutical preparation for the treatment of lipid metabolism disorders (hyperlipoproteinemia) |
| WO1997039115A1 (en) * | 1996-04-16 | 1997-10-23 | Yeda Research And Development Co. Ltd. | Immobilized alliinase and continuous production of allicin |
Non-Patent Citations (6)
| Title |
|---|
| K.T. AUGUSTI ET AL : "Lipid lowering effect of allicin (diallyldisulphide-oxide ON Lon long term feeding to normal rats" EXPERIENTIA., vol. 30, no. 5, 1974, pages 468-470, XP000979572 BIRKHAUSER VERLAG. BASEL., CH ISSN: 0014-4754 cited in the application * |
| PATENT ABSTRACTS OF JAPAN vol. 011, no. 259 (C-441), 21 August 1987 (1987-08-21) & JP 62 061925 A (RIKEN KAGAKU KOGYO KK;OTHERS: 01), 18 March 1987 (1987-03-18) * |
| PATENT ABSTRACTS OF JAPAN vol. 017, no. 185 (C-1047), 12 April 1993 (1993-04-12) & JP 04 338336 A (RIKEN HERUSU KK), 25 November 1992 (1992-11-25) * |
| PATENT ABSTRACTS OF JAPAN vol. 018, no. 040 (C-1155), 21 January 1994 (1994-01-21) & JP 05 268906 A (MICHIYASU HAMAYA), 19 October 1993 (1993-10-19) * |
| PATENT ABSTRACTS OF JAPAN vol. 1996, no. 03, 29 March 1996 (1996-03-29) & JP 07 304683 A (RIKEN HEALTH KK), 21 November 1995 (1995-11-21) * |
| YOON SHIK LEE : "A comparative study of the effect of allicin and arsenite on albino rats with special regard to the effect on body weight, hemoglobin, and hepatic histology" NEW MEDICAL JOURNAL, no. 1, 1967, pages 99-101, XP000983088 seoul, korea * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7157422B2 (en) | 2000-01-03 | 2007-01-02 | Tel Aviv University Future Technology Development L.P. | Glycogen synthase kinase-3 inhibitors |
| US7348308B2 (en) | 2000-01-03 | 2008-03-25 | Tel Aviv University Future Technology Development L.P. | Glycogen synthase kinase-3 inhibitors |
| US7378432B2 (en) | 2001-09-14 | 2008-05-27 | Tel Aviv University Future Technology Development L.P. | Glycogen synthase kinase-3 inhibitors |
| US8088941B2 (en) | 2001-09-14 | 2012-01-03 | Tel Aviv University Future Technology Development L.P. | Glycogen synthase kinase-3 inhibitors |
| US7446092B2 (en) | 2002-12-12 | 2008-11-04 | Tel Aviv University Future Technology Development L.P. | Glycogen synthase kinase-3 inhibitors |
| US7833974B2 (en) | 2002-12-12 | 2010-11-16 | Tel Aviv University Future Technology Development L.P. | Glycogen synthase kinase-3 inhibitors |
| EP1890693A2 (en) * | 2005-06-13 | 2008-02-27 | Yeda Research And Development Co., Ltd. | Use of allylmercaptocaptopril for treating or preventing obesity and obesity related diseases |
| EP1890693A4 (en) * | 2005-06-13 | 2009-09-30 | Yeda Res & Dev | Use of allylmercaptocaptopril for treating or preventing obesity and obesity related diseases |
| CN100389760C (en) * | 2006-04-18 | 2008-05-28 | 张国清 | Enteric coated drop pills of garlicin, and preparation method |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000074663A3 (en) | 2001-08-02 |
| IL130325A0 (en) | 2000-06-01 |
| AU4947400A (en) | 2000-12-28 |
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