WO1994025035A1 - Use of simmondsine - Google Patents

Use of simmondsine Download PDF

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Publication number
WO1994025035A1
WO1994025035A1 PCT/EP1994/001434 EP9401434W WO9425035A1 WO 1994025035 A1 WO1994025035 A1 WO 1994025035A1 EP 9401434 W EP9401434 W EP 9401434W WO 9425035 A1 WO9425035 A1 WO 9425035A1
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WIPO (PCT)
Prior art keywords
simmondsine
animals
use according
flour
jojoba
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PCT/EP1994/001434
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English (en)
French (fr)
Inventor
Eddy Decuypere
Marnix Cokelaere
Paul Daenens
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K.U. Leuven Research & Development
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Application filed by K.U. Leuven Research & Development filed Critical K.U. Leuven Research & Development
Priority to AU67232/94A priority Critical patent/AU6723294A/en
Publication of WO1994025035A1 publication Critical patent/WO1994025035A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7004Monosaccharides having only carbon, hydrogen and oxygen atoms
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/10Organic substances
    • A23K20/163Sugars; Polysaccharides
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K50/00Feeding-stuffs specially adapted for particular animals
    • A23K50/70Feeding-stuffs specially adapted for particular animals for birds
    • A23K50/75Feeding-stuffs specially adapted for particular animals for birds for poultry
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/203Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems

Definitions

  • the present invention relates to the use of simmondsine for influencing the food intake by animals.
  • a rapid weight gain due to high food intake by future mother animals can however result, among other things, in reduced fertility, defects of the legs and an increased mortality rate.
  • the mother animals are placed on a strict feed limitation diet. This means for instance that the farmer must weigh the animals regularly and administer feed in accordance with the weight development and sometimes deprive the animals of food for one or two successive days. This is not only very labour- intensive for the farmer but also very unpleasant for the animals in question. Such a method therefore also encounters growing opposition from animal protection groups.
  • House pets such as dogs, cats, guinea pigs, doves and suchlike can become overweight through too much feeding. Such an overweight condition is obviously not beneficial to the health of the animal.
  • subjecting these animals to fasting is not easy because the animal is used to a certain amount of food a day. It is unpleasant for the animal if it can not receive its usual amount of food and this can lead to troublesome behaviour in the animals as a consequence.
  • an animal friendly manner of food reduction is desired.
  • the present invention therefore relates to the use of simmondsine and/or its derivatives and/or its analogues in a suitable, dose for influencing the food intake by animals such as fish, birds and mammals.
  • simmondsine is understood, in the accompanying claims, all sources and administrable forms of simmondsine and substances derived from or related to simmondsine which display biological activity consistant with pure simmondsine. This not only includes, for instance, simmondsine and its derivatives and analogues in pure or unpure form, but also includes jojoba flour which can be, if necessary, heated and/or de-oiled. Jojoba flour can be used separately or as part of an admixture. Combinations of simmondsine and jojoba flour are also possible.
  • pure simmondsine(s) is meant, in the description, the isolated more or less pure forms of simmondsine and its derivatives.
  • pure simmondsine and “pure simmondsines” can be used together.
  • jojoba flour all the herewith, whether or not, treated, for instance de-oiled, heated etc. forms of the flour are meant which can be obtained from the jojoba plant.
  • simmondsine Apart from this, it appears by both young animals as well as young people (adolescents) that as a result of simmondsine a higher maintenance metabolism also results whereby weight loss occurs faster than by normal fasting.
  • the above mentioned hormone cholecystokinine stimulates the enzyme production by the pancreas. This increased enzyme production leads to a protein loss, especially of essential amino acids.
  • T3 tri- iodothyronine
  • T3 tri- iodothyronine
  • One application of the use of simmondsine is, for instance, found in the keeping of stock animals for fattening such as chick-mother animals.
  • simmondsine has been found in weight loss diets of small pets, such as dogs, cats, guinea pigs, rabbits, hamsters, rats, mice, chinchilla's, doves, canaries, parrots etc.
  • Pure simmondsine can in such instances be mixed in an amount of 0.05%-1.0% with the feed which itself can have a reduced energy content, and which can be in a dry or wet form, pasteurized, extruded or sterilized.
  • Simmondsine can also be dissolved in drinking water or can be applied in the form of tablets, capsules or other forms of administering medicine.
  • jojoba flour When de-oiled and/or heated integral jojoba flour is used, the dosing is dependant on the simmondsine content (simmondsine and its analogues simmondsine-2 '-ferulate, but also other simmondsine-like substances) , this content being between 0.5 and 20%.
  • This jojoba flour can be administered in the same way as pure simmondsine but not as a solution. Dependant on the dosing a reduction in food intake from 5- 50%, but mostly between 5-25%, can be achieved.
  • the treatment can, if desired, be carried out over a shorter or longer time period, for instance between 1 day and 1 year.
  • the recuperation growth in animals for slaughter can be achieved by a 10-20% food reduction, introduced during the second, third and possible fourth week whereafter the animals are allowed to eat ad libitum.
  • a food reduction of 10-20% can be brought about by mixing 0.1-0.25% simmondsine activity or 2- 5% jojoba flour into the feed.
  • 0.1-0.25% simmondsine activity agrees with 0.1-0.25% simmondsine or 0.15-0.37% simmondsine-2 '-ferulate.
  • the simmondsine activity of simmondsine-2 '-ferulate is 0.68 x the activity of simmondsine itself.
  • the recuperation growth can apart from poultry also be induced in pigs or cattle for fattening.
  • simmondsine is therefore suitable for limiting the food intake in all sorts of animals including humans, but finds practical application particularly in livestock for fattening and livestock mother animals, for countering too strong growth and for bringing about weight loss for pets.
  • Simmondsine can be administered to animals in diverse ways, for example in the form of pure simmondsine or as an admixture of de-oiled or possibly heated jojoba flour to the feed.
  • an extra simmondsine extract from the jojoba plant can also be added to the de-oiled jojoba flour.
  • the jojoba flour can be separated from its oil in various different ways.
  • the flour is de-oiled by means of hexane.
  • De-oiled jojoba flour for administering to animals is preferably heated for a while in order to break up the trypsine inhibitors present in the jojoba flour. Heating can be carried out for 30-120 minutes at 100-120°C for example. When heated jojoba flour is used, it appears that an enduring, and very well predictable dose-dependant food intake reduction can be achieved.
  • simmondsine Apart from simmondsine itself, derivatives and/or analogues of simmondsine can also be used such as simmondsine-2 '-ferulate or aglucones of simmondsine.
  • the invention further relates to a method for isolating and purifying simmondsine and/or derivatives and/or analogues thereof, comprising the steps of: a) extracting de-oiled jojoba flour in order to obtain an extract; b) separating the extract into fractions by means of adsorption chromatography; c) filtering the fractions containing the simmond ⁇ sine and/or derivatives and/or analogues thereof to obtain a filtrate; d) separating the filtrate into fractions again by means of adsorption chromatography; and e) crystallizing the simmondsine and/or derivatives and/or analogues thereof. It is likewise possible to concentrate the extract respectively the filtrate prior to the chromatography step.
  • the extraction is performed with acetone
  • the first chroma ⁇ tography takes place on a silica gel column with acetone as eluant
  • the filtration takes place over activated carbon
  • the second chromatography takes place on a silica gel column with chloroform/methanol (95:5) as eluant.
  • Concentration preferably takes place by means of dissolving the extract respectively the filtrate in methanol and subsequently evaporating the methanol under vacuum.
  • simmondsine indirectly influences the manufacture of the thyroid hormones in the body. In growing animals tha manufacture is stimulated, while in adult animals it is inhibited. In this experiment the influence of simmondsine in a pure form and in the form of de-oiled jojoba flour on the production of T3 , T4 and TSH hormones, is investigated in adult Wistar rats.
  • Blood sampling takes place by cutting off a portion of the tail.
  • the blood is collected in heparinized vessels and the plasma is immediately centrifuged off and stored in the deep-freeze until hormone assays are possible. After 2, 6, 10, 14, 18 and 22 hours blood is taken in order to determine the circadian rhythm of the hormone concentrations.
  • Hormone assays are performed by means of RIA tests on the thyroid hormones T3 (tri-iodothyronine) , T4 and TSH.
  • the 2 x 10 controls are pooled into one group.
  • mice of group S exhibit a feed intake inhibition of about 50%.
  • Table 1 shows the plasma concentration (ng/ml) of T3 in male Wistar rats after 11 days administration of 0.5% pure simmondsine in the feed.
  • the different indices (a, b, c) designate statistically significant differences (p ⁇ 0.05) .
  • the lower values represent the S.E.M..
  • Group C consists of control animals, the animals of group JJ receive for 11 days 10% de- oiled jojoba flour mixed through their feed, the animals of group PF receive precisely the same amount of ordinary feed as the JJ group consumes (pair-fed group) .
  • Blood sampling and hormone assays are performed in the same manner as under 1.1 above.
  • Table 6 shows the plasma THS concentrations (ng/ml) in male Wistar rats after 11 days admixing of 10% de-oiled jojoba flour.
  • the different indices designate statistically significant differences (p ⁇ 0.05) .
  • the lower values represent the S.E.M..
  • TSH, T3 and T4 concentration there is a fall in TSH, T3 and T4 concentration relative to the controls, which can be expected because the animals are fasting.
  • the T3 and T4 fall is more strongly pronounced in the group treated with jojoba flour, although this is not everywhere statistically significant.
  • the fall in TSH content can be wholly explained by the fasting.
  • the treatment with jojoba flour has no influence hereon.
  • TSH content falls under the influence of fasting but no influence as such can be seen from the treatment with simmondsine or jojoba flour.
  • simmondsine-2 '-ferulate causes approximately 68% of the feed intake inhibition of simmondsine (research of the inventors) . This therefore means that 3% jojoba flour contains the equivalent of 0.12% active simmondsine. In preparatory tests it was found that the feed intake inhibition amounts in both situations to about 20%, despite the difference in active simmondsines.
  • Group C consists of controls
  • group S consists of animals treated with 0.15% simmondsine in feed
  • group JJ contains animals treated with 3% jojoba flour de-oiled with hexane in the feed
  • group PFS consists of rats which are pair-fed with S
  • group PFJ contains the rats which are pair-fed with JJ.
  • PFS and PFJ tests start one week later on animals born one week later, so that at the start they are the same age and weigh as much as C, S and JJ.
  • Table 7 shows the weight evolution in grams (only average weights) .
  • the different indices (a, b, c) designate statistically significant differences.
  • Table 8 shows the feed intake (gram/week/animal) (only mean values) .
  • Table 9 shows the relative growth.
  • the different indices (a, b, c) designate statistically significant differences.
  • Table 10 shows the food conversion.
  • the different indices (a, b, c) designate statistically significant differences.
  • the effect of 0.15% simmondsine and 3% jojoba flour is the same for feed intake inhibition, growth, relative growth and feed conversion. Feed intake amounts to ⁇ 80% of that of the control group C.
  • Relative growth and food conversion in group S and group JJ are less than in group C in the first half of the test but the same as the controls in the second half.
  • the relative growth and the food conversion of the pair-feds is better in the first half than in the groups S and JJ but becomes the same in the second half.
  • the relative growth and food conversion in the case of the pair-feds is less during the first four weeks than in the controls but the relative growth becomes equal to and the food conversion even becomes better than in the controls at the end of the test.
  • Group C consisting of controls are fed normally, group S receives feed with 0.15% simmondsine, group JJ receives feed with 3% jojoba flour de-oiled with hexane, group PFS is pair-fed daily with the S group and group PFJ is pair-fed daily with the JJ group.
  • BW body weight
  • Table 11 shows the mean body weight, pancreas weight and pancreas weight as % of the body weight. Each group numbers 10 animals. The different indices (a, b, c) designate statistically significant differences (p ⁇ 0.05) . Table 11
  • Chickens are an important target group for the application of simmondsine according to the invention.
  • the influence of pure simmondsine on chickens is examined.
  • Test conditions 20 spring chicks of about 400 grams receive feed ad libitum. They are divided into 5 groups of 4 animals and their feed intake is checked after 1, 2, 4, 6, 8 and 24 hours.
  • Group C consists of control animals, group IT receives 250 mg/kg simmondsine intubated into the stomach, group IV receives 250 mg/kg administered intravenously, group IP receives 250 mg/kg administered intraperitoneally, group IVO receives 140 mg/animal calculated per day mixed into the feed. 2 . Results
  • Table 12 shows the average food intake expressed per kg body weight in growing chickens for slaughter.
  • simmondsine exhibits a marked effect on the food intake in IT, IV and IVO.
  • IT acts certainly for 8 hours, in IV a maximum of 4 hours, in IVO permanently.
  • IV a maximum of 4 hours, in IVO permanently.
  • the controls eat less (due to sensation of satisfaction) a less pronounced additional influence of simmondsine is observable, which points once again to a satisfaction- increasing effect of simmondsine.
  • the mean initial body weight of these groups was the same.
  • the food intake was limited in accordance with the recommendations of the breeder (weeks 4 and 5: 45 g per chick per day; weeks 6 and 7: 47 g per chick per day) .
  • the other groups had unlimited access to commercially available feed supplemented with 0 (control), 2, 4, 6, 8, 10 or 12% jojoba flour de-oiled with hexane (0-12% JO) .
  • the de- oiled jojoba flour contained 4.15% simmondsine and 0.7% simmondsine-2 *-ferulate.
  • Plasma growth hormone, insulin growth factor-I, T4 and T3 concentrations at week 4 are shown in table 14.
  • Jojoba flour supplement and food limitation increased the circulating plasma growth hormone compared to the 0% JO value. Pair-feeding had no significant effect on plasma growth hormone compared to 0% JO. Compared to 0% JO value all diet treatments reduced the plasma IGF-I significantly. The lowest plasma IGF-I values were observed in R chicks. Plasma T3 quantities in 4% JO chicks were comparable to those of 0% JO chicks and significantly higher than those of the PF and R birds. The highest plasma T4 concentrations were observed in the PF chicks. Plasma T4 did not differ between 0% JO and 4% JO chicks, while plasma T4 of the R chicks lay between that of the 0% JO and the PF chicks.
  • the 24 hour food intake of 10 adult male rats (363 ⁇ 6 grams) was measured during three days. After this, food was offered for three days to the rats, wherein 0.5 wt.% HPLC-pure simmondsine (S) was admixed. The 24 hours' food intake of the rats was measured daily. After a recovery period of 1 week, food was offered to the rats during three days wherein 0.5 weight per cent HPLC-pure simmondsine-2 '- ferulate (SF) was admixed. Their daily food intake was again measured.
  • S HPLC-pure simmondsine
  • SF HPLC-pure simmondsine-2 '- ferulate
  • EXAMPLE 7 The effect of trypsine inhibitors and skin factors on the food intake inhibition caused by de-oiled jojoba flour.
  • the integral jojoba flour originates from Israel and had been cold pressed (max. 60°C) . It was de-oiled with hexane in a Soxhlet apparatus. Heated integral de-oiled flour was heated in a dry oven for 1 hour at 120°C.
  • the de-skinned and heated flour was ground and de-oiled with hexane in a Soxhlet apparatus.
  • the de-skinned and heated flour, the integral flour, the heated integral flour and the skin factors were obtained as above.
  • 11 Groups of each 8 just weaned male Wistar rats were given complete laboratory food for rats, in the form of flour, for 4 weeks. Apart from a control group (C) , groups of 5 rats each were examined, that were given food according to the scheme below:
  • the food intake was measured on a daily basis.
  • a group of 8 rats was also pair-fed with these 5 groups (they received daily the same amount of food as their respective treated group had received the day before) (PDS,PI, PSS, PDSAA; PSK) .
  • the total weight of flour was 1,300 grams, of which 135 grams were skin parts. After boiling, 15 grams of crystalline material were obtained from the cooking fluid. This means that the jojoba nut (originating from Israel) contained 11.5% skin. Converted, the integral jojoba flour contained 23% skin (factors) considering the jojoba nut consisted for ⁇ 50% of liquid wax (oil) .
  • simmondsine active elements Pure simmondsine (S) + simmondsine-2 '-ferulate x 0.68 (SF) ) in rat feed.
  • the feed intake inhibition is illustrated in figure 3.
  • the relative growth and food conversion are disadvantageously influenced by the food intake inhibition.
  • the presence of simmondsines in DS and SS strengthened this occurance especially in week 3, but weakened again in week 4.
  • Non heated integral flour causes a much stronger food intake inhibition and an even worse food conversion and relative growth. Switching over to heated integral flour causes a rapidly improved food conversion and relative growth, although after a two week pre-treatment with non- heated integral jojoba flour, the food intake did not strongly improve.
  • the skin itself has little or no effect on the food intake, food conversion or growth rate.
  • Heated and de-oiled integral jojoba flour causes an enduring, predictable dose-dependant food intake inhibition amongst rats, which can be completely explained by the presence of simmondsine and simmondsine-2'-ferulate. Trypsine inhibitors from the protein fraction and the skin can be destroyed by heating. If the integral jojoba flour is not heated, there occurs a very bad growth performance and food conversion. The de-oiled integral jojoba flour must be sufficienly heated, for use with animals, in order to destroy the trypsine inhibitors. EXAMPLE 8
  • Jojoba flour was obtained from EMEC Agro
  • Jojoba flour was first extracted with hexane to remove residual oil.
  • 1 kg de-oiled flour was extracted with acetone for 12 hours by means of a Soxhlet apparatus. After evaporation of the solvent 40 g of a brown residue was obtained.
  • the residue was dissolved in methanol and adsorbed onto 100 g of silica gel (0.2-0.5 mm).
  • the methanol was removed under vacuum and the silica gel placed on top of a silica gel column (length 30 cm, diameter 6 cm) which contained a suspension of 1 kg silica gel (0.040-0.063 mm) in chloroform.
  • the column was first eluated with 1 litre chloroform and the organic solvent thrown away, followed by elution with acetone.
  • a solution of the non- purified simmondsine in methanol was first adsorbed onto silica gel (0.2-0.5 mm) and after evaporation of the solvent placed on top of the column. Elution was carried out with a mixture of methanol and chloroform (5/95, v/v) . The eluates were guided through an UV cell to immediately determine the eluting compounds and corresponding fractions were separately collected. All peaks were examined for the presence of simmondsine and analogues by HPLC. The fractions containing only simmondsine were collected and the solvent evaporated under vacuum. The residue (22 g) was crystallized from ethylacetate/methanol (1:3).
  • the yield of pure simmondsine amounted to 1.8% on the basis of the jojoba flour.
  • the purity of simmondsine was checked by means of a TLC and an HPLC procedure.
  • the TLC showed only one violet coloured spot and the HPLC analysis only one peak.
  • the simmondsine was obtained as colourless crystals from ethylacetate.

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PCT/EP1994/001434 1993-04-29 1994-04-27 Use of simmondsine WO1994025035A1 (en)

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BE9300434A BE1006958A3 (nl) 1993-04-29 1993-04-29 Werkwijze voor het beinvloeden van de voedselopname door mensen en dieren.
BE9300434 1993-04-29

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0791299A1 (en) * 1996-02-20 1997-08-27 André d'Oosterlynck Method for separating the toxic resinous fraction from prepared whole jojoba seeds or jojoba seed presscake
US5672371A (en) * 1994-11-17 1997-09-30 D'oosterlynck; Andre Method for separating the toxic resinous fraction from prepared whole jojoba seeds or jojoba seed press-cake
US5962043A (en) * 1996-02-29 1999-10-05 Seal Rock Technologies Incorporated Weight reduction method for dogs and other pets
US6245364B1 (en) 1996-02-29 2001-06-12 International Flora Technologies, Ltd. Weight reduction method for cats and other pets
KR100349334B1 (ko) * 1999-12-08 2002-08-21 박관화 아카비오신 글루코실 시몬진 및 그것의 제조방법.
USRE38167E1 (en) * 1996-02-29 2003-07-01 International Flora Technologies Ltd Weight reduction method for cats and other pets
WO2004004746A1 (en) * 2002-07-08 2004-01-15 D Oosterlynck Andre Simmondsin for use as an angiogenesis inhibitor
EP1429794A1 (en) * 2001-09-07 2004-06-23 International Flora Technologies, Ltd. Weight reduction and maintenance method for animals
US6852342B2 (en) * 2002-03-26 2005-02-08 Avoca, Inc. Compounds for altering food intake in humans
US7138134B2 (en) 2001-12-18 2006-11-21 Arizona Health Consulting Group, Llc Preparation and administration of jojoba product for reducing weight, fat and blood lipid levels

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3531380A1 (de) * 1985-09-03 1987-03-12 Jojoba Oil Gmbh Therapeutisches mittel fuer eine abmagerungsdiaet
NL8901639A (nl) * 1989-06-05 1991-01-02 Hugo Dangreau En Marnix Cokela Simmondsine, aglyconsimmondsine, een isolatiewerkwijze daarvoor, alsook het therapeutische gebruik daarvan.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3531380A1 (de) * 1985-09-03 1987-03-12 Jojoba Oil Gmbh Therapeutisches mittel fuer eine abmagerungsdiaet
NL8901639A (nl) * 1989-06-05 1991-01-02 Hugo Dangreau En Marnix Cokela Simmondsine, aglyconsimmondsine, een isolatiewerkwijze daarvoor, alsook het therapeutische gebruik daarvan.

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
A.N. BOOTH ET AL.: "Isolation of a toxic factor from jojoba meal", LIFE SCIENCES, vol. 15, no. 6, 1974, US, pages 11115 - 11120 *
J.D.NGOU NGOUPAYOU ET AL.: "Jojoba meal in poultry diets", POULTRY SCIENCE, vol. 61, 1982, US, pages 1692 - 1696 *
M. VAN BOVEN ET AL.: "Isolation, purification, and stereochemistry of simmondsin", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 41, no. 10, 1993, WASHINGTON US, pages 1605 - 1607 *
M.M. COKELAERE ET AL.: "Influence of pure simmondsin on the food intake in rats", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 40, no. 10, 1992, WASHINGTON US, pages 1839 - 1842 *
MEGANNE O. WISEMAN ET AL.: "Characterization of protein concentrates of jojoba (Simondsia chinensis) meal", CEREAL CHEMISTRY, vol. 64, no. 2, 1987, MINNEAPOLIS US, pages 91 - 93 *
S. ARNOUTS ET AL.: "Jojoba meal (Simmondsia chinensis) in the diet of broiler breeder pullets: Physiological and endocrinological effects", POULTRY SCIENCE, vol. 72, no. 9, 1993, US, pages 1714 - 1721 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5672371A (en) * 1994-11-17 1997-09-30 D'oosterlynck; Andre Method for separating the toxic resinous fraction from prepared whole jojoba seeds or jojoba seed press-cake
EP0791299A1 (en) * 1996-02-20 1997-08-27 André d'Oosterlynck Method for separating the toxic resinous fraction from prepared whole jojoba seeds or jojoba seed presscake
USRE38167E1 (en) * 1996-02-29 2003-07-01 International Flora Technologies Ltd Weight reduction method for cats and other pets
US6245364B1 (en) 1996-02-29 2001-06-12 International Flora Technologies, Ltd. Weight reduction method for cats and other pets
USRE38155E1 (en) * 1996-02-29 2003-06-24 International Flora Technologies Ltd Weight reduction method for dogs and other pets
US5962043A (en) * 1996-02-29 1999-10-05 Seal Rock Technologies Incorporated Weight reduction method for dogs and other pets
KR100349334B1 (ko) * 1999-12-08 2002-08-21 박관화 아카비오신 글루코실 시몬진 및 그것의 제조방법.
EP1429794A1 (en) * 2001-09-07 2004-06-23 International Flora Technologies, Ltd. Weight reduction and maintenance method for animals
EP1429794A4 (en) * 2001-09-08 2004-11-10 Int Flora Technologies Ltd METHOD FOR WEIGHT REDUCTION AND MAINTENANCE OF THE WEIGHT OF ANIMALS
US7138134B2 (en) 2001-12-18 2006-11-21 Arizona Health Consulting Group, Llc Preparation and administration of jojoba product for reducing weight, fat and blood lipid levels
US8673343B2 (en) 2001-12-18 2014-03-18 Yiwu Jiangr Bio-Technology HK Corp. Preparation and administration of jojoba product for reducing weight, fat and blood lipid levels and for the prevention and treatment of cancer
US6852342B2 (en) * 2002-03-26 2005-02-08 Avoca, Inc. Compounds for altering food intake in humans
WO2004004746A1 (en) * 2002-07-08 2004-01-15 D Oosterlynck Andre Simmondsin for use as an angiogenesis inhibitor
BE1015023A3 (fr) * 2002-07-08 2004-08-03 Oosterlijnck Andre D L'usage de la farine raffinee et deshuilee du jojoba ou un ou plusieurs de ces composants bio-actives comme agent inhibiteur de l'angiogenese dans la lutte contre le cancer.
US7387999B2 (en) * 2002-07-08 2008-06-17 André D'Oosterlynck Simmondsin for use as angiogenesis inhibitor

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IL109409A0 (en) 1994-07-31
BE1006958A3 (nl) 1995-01-31

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