WO2002070069A2 - Utilisation d'un ou plusieurs shogaol(s) en tant qu'aphrodisiaque - Google Patents
Utilisation d'un ou plusieurs shogaol(s) en tant qu'aphrodisiaque Download PDFInfo
- Publication number
- WO2002070069A2 WO2002070069A2 PCT/FR2002/000784 FR0200784W WO02070069A2 WO 2002070069 A2 WO2002070069 A2 WO 2002070069A2 FR 0200784 W FR0200784 W FR 0200784W WO 02070069 A2 WO02070069 A2 WO 02070069A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- shogaol
- rhizomes
- advantageously
- extract
- plant
- Prior art date
Links
- 0 C*C=CC(CC*(C)(C)c(cc1)cc(OC)c1O)=O Chemical compound C*C=CC(CC*(C)(C)c(cc1)cc(OC)c1O)=O 0.000 description 1
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
- A61K31/12—Ketones
-
- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/906—Zingiberaceae (Ginger family)
- A61K36/9062—Alpinia, e.g. red ginger or galangal
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/906—Zingiberaceae (Ginger family)
- A61K36/9068—Zingiber, e.g. garden ginger
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
Definitions
- TITLE "USE OF ONE OR MORE SHOGAOL (S) AS AN APHRODISIAC".
- the present invention relates to aphrodisiacs. It relates in particular to the use of one or more shogaol (s) as an aphrodisiac. Since the dawn of time, many substances have been used for the purpose of increasing sexual desire (libido). Some of them have been very successful and have been passed down over the centuries. However, none of these substances has survived the scrutiny of scientists. As a result, the search for a real aphrodisiac continues. The Applicant has surprisingly discovered that the shogaol (s) have had an aphrodisiac action on both men and women.
- Shogaols have already been described as having deodorant and / or antiseptic activity (FR 2758086).
- Some shogaols are also known chemical constituents of plants of the Aîpinia genus, such as Alpinia galanga or Alpinia officinarum or Zingiber, such as Zingiber officinalis, Zingiber cassumunar or Zingiber zerumbet, obtained by extraction from their rhizome.
- the ginger belonging to the family of Zingiber officinalis is a spice well like and used in many culinary preparations and has the reputation of being an aphrodisiac.
- the quantity of chemical constituents present in its rhizome (geraniol, geranyl acetate, linalool, lemonyl acetate, ⁇ -terpineol, borneol, bornyl acetate, neral, genital, ⁇ -bisabolene, (-) - zingiberene, ( +) - r-curcumene, ⁇ -sesquiphellandrène, gingerols etc.), it is difficult to know to which or to which of these this aphrodisiac activity is due.
- the applicant has therefore surprisingly discovered that the shogaol (s), compound (s) of the family of arylalkanones, had (a) an aphrodisiac action on the man and / or the woman.
- the present invention therefore relates to the use of one or more shogaol (s) as an aphrodisiac.
- aphrodisiac in the sense of the present invention, the stimulation or the awakening of the libido, i.e. of the sexual desire.
- the present invention relates to the use of one or more shogaol (s) as an erectogen or to stimulate or stimulate the libido in humans.
- s shogaol
- the shogaol (s) correspond (s) to the general formula
- n is equal to 1, 2, 4, 6 or 8 and which are respectively named [3] - shogaol, [4] -shogaol, [6] -shogaol, [8] -shogaol and [10] -shogaol.
- the shogaol (s) are in the form of a crude extract of a plant of the family Zingiberaceae, advantageously by a process which comprises the following step: a) preparation of crude extract from rhizomes, fresh or dried, of said plant, by maceration of a ground material of these rhizomes at a temperature between 10 and 35 ° C, followed by one or more reflux extractions of this ground material, or by subjecting a ground material of said rhizomes to percolation at a temperature between 10 and 35 ° C, each of these operations (maceration, reflux extraction and percolation) being carried out using an organic solvent or a mixture of appropriate organic solvents.
- the maceration of the ground rhizomes, prior to its extraction, has the main effect of improving the contacting of the plant tissues and the solvent during the extraction. Its duration can be between a dozen hours and a week depending on the state of freshness of the rhizomes used.
- organic solvents are used which are miscible with water and have a relatively low boiling point so that they can be easily removed later by simple evaporation.
- organic solvents such as ethanol, methanol, acetone or their mixtures with water.
- shogaols are soluble in many organic solvents, it is also possible to use other organic solvents such as ethyl acetate, ethyl ether, chloroform or methylene chloride.
- the shogaol (s) are in the form of a purified extract of a plant of the zingiberaceae family, advantageously obtained by a process which comprises, in addition to step a) described below above, the following additional steps: b) purification of the crude extract obtained in step a) by subjecting said extract, after elimination of the solvent or solvents which it contains and its recovery in water, to one or more several extractions against the current using an organic solvent or a mixture of organic solvents immiscible with water and, if desired, c) chromatographic separation of the shogaols.
- the water-immiscible organic solvent (s) useful for carrying out the counter-current extractions of the crude extract with a view to its purification are, in particular, chosen from ethyl acetate, ethyl ether, chloroform , methylene chloride and mixtures thereof.
- the plant of the zingiberaceae family is chosen from the species Alpinia galanga, Alpinia officinarum, Zingiber officinalis, Zingiber cassumunar and Zingiber zerumbet, even more advantageously, it is V Alpinia galanga.
- [3] -shogaol, [6] -shogaol and [8] -shogaol can be extracted from plants of the genus Alpinia such as : lpinia galanga or Alpinia officinarum, while [4] -shogaol and [10] -shogaol can be extracted from plants of the genus Zingiber such as Zingiber officinalis, Zingiber cassumunar or Zingiber zerumbet, in particular using the method as described above.
- the raw extract of Alpinia galanga contains a quantity of
- [3] -shogaol comprised by weight between approximately 1 to 5% of the dry weight of said extract.
- this extract is obtained from rhizomes, fresh or dry, of said plant.
- the purified extract pin'Alpinia galanga contains an amount of [3] -shogaol at least equal by weight to 75% of the dry weight of said extract.
- the present invention also relates to the use of one or more shogaol (s) for the preparation of an aphrodisiac composition.
- the aphrodisiac composition is formulated for oral administration, for example, in the form of powders, solutions or oral suspensions, syrups, tablets or capsules.
- the present invention also relates to a method for arousing or stimulating libido in human beings, characterized in that it comprises the administration to a human being of an effective amount of one or more shogaol (s) such (s) as defined above.
- s shogaol
- Example 1 Preparation of a crude extract of rhizomes of Alpinia galanga
- a kilo of fresh rhizomes in 'Alpinia galanga is coarsely ground, taking care not to cause excessive heating of the ground parts.
- the water content of the ground product thus obtained is determined and it is macerated in 7 liters of ethanol, the title of which is chosen so that, taking into account the water content of the ground material, the maceration solvent is 50% ethanol.
- the ground material is extracted at reflux with the maceration solvent for 30 minutes. This solvent is removed and replaced with an equal weight of 50% ethanol, and the ground material is again extracted at reflux for 30 minutes. The operation is repeated once.
- the 3 extracts obtained are combined (thus constituting a volume of about 19 liters), filtered on paper, then evaporated to dryness under reduced pressure.
- a residue is obtained which weighs approximately 50 g, ie an approximate yield of 30% relative to the dry weight of the rhizomes.
- This extract contains the various shogaols present in the rhizomes of Alpinia galanga ([3] -shogaol, [6] -shogaol and [8] -shogaol) and its [3] -shogaol content is generally between 1 and 5% (w / w) depending on the rhizomes used.
- [3] -shogaol can be obtained from rhizomes of 'Alpinia galanga by preparing a crude extract of these rhizomes in accordance with Example 1, then purifying this extract in accordance with Example 2 and then subjecting the extract thus purified by successive elutions on columns of silica gel, for example in the following manner.
- This powder is deposited at the top of a column 10 cm in diameter and 50 cm in height, also containing G60 silica gel in petroleum ether. First eluted with petroleum ether until the residue is less than 0.1% (approximately 10 liters of petroleum ether necessary to reach this stage), then with 12 liters of benzene and , finally, per 8 liters of chloroform.
- the chloroform phase is evaporated to dryness under reduced pressure, leaving room for a residue of approximately 2.3 g.
- This residue is then subjected to preparative chromatography on a column 5 cm in diameter and 20 cm in height, filled with Cl 8 silica gel, and using a water / acetonitrile mixture (70/30) as an elution gradient. .
- the fraction containing [3] -shogaol is eluted in a time between 5 and 7 minutes for a flow rate of 30 ml / min.
- [3] -shogaol can be identified by high pressure liquid chromatography (HPLC) coupled with mass spectrometry.
- HPLC high pressure liquid chromatography
- capsules can be made from [3] -shogaol to obtain a unit dosage of 25 mg of [3] -shogaol.
- Example 5 Shogaol test on mice: functional study and sexual behavior.
- mice weigh 30 g for males and 25 g for females. They are conditioned by 8 males per 545 cm2 cage and 5 females + 1 male per cage.
- the shogaol is suspended in water at the rate of 0.09 mg of active ingredient / 200 ml of solution.
- the mice receive by gavage 3 mg / kg of active ingredient per day.
- the males in the SH + group seem less aggressive than the males in the control group: no aggression between congeners.
- the males in the SH + group show more developed sexual activity than the males in the control group.
- the male is brought into contact with the females, there is a change in the behavior of the SH + male: round back, ruffled hair, pursuit of the females, uncontrolled ejaculation.
- This sexual activity continues in the presence of full females.
- the percentage of females taken by the male is identical (68%), the results show that the females are taken more quickly in the SH + group than in the control group.
- the following table shows the percentage of whelping females by date:
- mice of the SH + batch are one day ahead of the control batch and therefore that coitus was more spicy with the SH + males.
- 32% of the females are new full versus 11% for the females in the control batch.
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- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Botany (AREA)
- Biotechnology (AREA)
- Alternative & Traditional Medicine (AREA)
- Reproductive Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Endocrinology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gynecology & Obstetrics (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002442260A CA2442260A1 (fr) | 2001-03-05 | 2002-03-05 | Utilisation d'un ou plusieurs shogaol(s) en tant qu'aphrodisiaque |
JP2002569238A JP2004522790A (ja) | 2001-03-05 | 2002-03-05 | 催淫剤としての一つまたは複数のショウガオールの使用 |
US10/473,919 US20050238737A1 (en) | 2001-03-05 | 2002-03-05 | Use of one or more shogaol(s) as an aphrodisiac |
MXPA03008052A MXPA03008052A (es) | 2001-03-05 | 2002-03-05 | Uso de uno o mas shogaoles como un afrodisiaco. |
SK1114-2003A SK11142003A3 (sk) | 2001-03-05 | 2002-03-05 | Použitie jedného alebo viacerých šogaólov ako afrodiziak |
EP02713011A EP1368012A2 (fr) | 2001-03-05 | 2002-03-05 | Utilisation d'un ou plusieurs shogaol(s) en tant qu'aphrodisiaque |
HU0303468A HUP0303468A2 (hu) | 2001-03-05 | 2002-03-05 | Egy vagy több shogaol alkalmazása afrodiziákumként |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0102961A FR2821553B1 (fr) | 2001-03-05 | 2001-03-05 | Utilisation d'un ou plusieurs shogaol (s) en tant qu'aphrodisiaque |
FR01/02961 | 2001-03-05 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002070069A2 true WO2002070069A2 (fr) | 2002-09-12 |
WO2002070069A3 WO2002070069A3 (fr) | 2003-01-03 |
Family
ID=8860733
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2002/000784 WO2002070069A2 (fr) | 2001-03-05 | 2002-03-05 | Utilisation d'un ou plusieurs shogaol(s) en tant qu'aphrodisiaque |
Country Status (11)
Country | Link |
---|---|
US (1) | US20050238737A1 (fr) |
EP (1) | EP1368012A2 (fr) |
JP (1) | JP2004522790A (fr) |
CA (1) | CA2442260A1 (fr) |
CZ (1) | CZ20032634A3 (fr) |
FR (1) | FR2821553B1 (fr) |
HU (1) | HUP0303468A2 (fr) |
MX (1) | MXPA03008052A (fr) |
PL (1) | PL374103A1 (fr) |
SK (1) | SK11142003A3 (fr) |
WO (1) | WO2002070069A2 (fr) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2861298B1 (fr) * | 2003-10-24 | 2006-02-17 | Lmd | Acetoxyacetate de chavicol et ses derives en tant qu'aphrodisiaque |
WO2014195479A1 (fr) | 2013-06-07 | 2014-12-11 | Nerthus Aps | Préparation sèche d'alpinia galanga ou d'alpinia conchigera ayant une teneur élevée en acétate de 1's-1'-acétoxychavicol |
AU2014276836B2 (en) * | 2013-06-07 | 2019-11-21 | Nerthus Aps | Composition for enhancing semen quality in a male subject |
EP2952201B1 (fr) * | 2014-06-06 | 2017-06-21 | Nerthus ApS | Compositions d'Alpinia galanga ou Alpinia conchigera à teneur élevée en acétate 1'S-1'-acétoxychavicol approprié pour un traitement pharmaceutique |
JP7176813B2 (ja) * | 2017-09-21 | 2022-11-22 | ハウスウェルネスフーズ株式会社 | 疲労改善用組成物 |
CN113355166A (zh) * | 2021-06-30 | 2021-09-07 | 中国热带农业科学院热带作物品种资源研究所 | 一种抑制单增李斯特菌的高良姜精油的提取方法及高良姜精油 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2758086A1 (fr) * | 1997-01-09 | 1998-07-10 | Daniel Jean | Shogaols pour l'utilisation comme medicaments, produits cosmetiques et produits dietetiques, procede d'obtention desdits shogaols et extraits vegetaux les contenant |
US5879682A (en) * | 1995-11-24 | 1999-03-09 | Peya Biotech Inc | Aframonum seeds for improving penile activity |
WO2000035466A1 (fr) * | 1998-12-11 | 2000-06-22 | Peya Biotech Inc. | Graines d'aframomum ameliorant l'activite du penis |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69815866T2 (de) * | 1997-01-09 | 2004-05-13 | Lmd | Verwendung von shogaolen und gingerolen zur herstellung von deodoranzien |
-
2001
- 2001-03-05 FR FR0102961A patent/FR2821553B1/fr not_active Expired - Fee Related
-
2002
- 2002-03-05 MX MXPA03008052A patent/MXPA03008052A/es unknown
- 2002-03-05 US US10/473,919 patent/US20050238737A1/en not_active Abandoned
- 2002-03-05 EP EP02713011A patent/EP1368012A2/fr not_active Withdrawn
- 2002-03-05 JP JP2002569238A patent/JP2004522790A/ja not_active Abandoned
- 2002-03-05 CZ CZ20032634A patent/CZ20032634A3/cs unknown
- 2002-03-05 CA CA002442260A patent/CA2442260A1/fr not_active Abandoned
- 2002-03-05 SK SK1114-2003A patent/SK11142003A3/sk unknown
- 2002-03-05 HU HU0303468A patent/HUP0303468A2/hu unknown
- 2002-03-05 WO PCT/FR2002/000784 patent/WO2002070069A2/fr not_active Application Discontinuation
- 2002-03-05 PL PL02374103A patent/PL374103A1/xx not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5879682A (en) * | 1995-11-24 | 1999-03-09 | Peya Biotech Inc | Aframonum seeds for improving penile activity |
FR2758086A1 (fr) * | 1997-01-09 | 1998-07-10 | Daniel Jean | Shogaols pour l'utilisation comme medicaments, produits cosmetiques et produits dietetiques, procede d'obtention desdits shogaols et extraits vegetaux les contenant |
WO2000035466A1 (fr) * | 1998-12-11 | 2000-06-22 | Peya Biotech Inc. | Graines d'aframomum ameliorant l'activite du penis |
Non-Patent Citations (4)
Title |
---|
"Indian Materia Medica K.M." , BOMBAY POPULAR PRAKASHAN ED. , 1976 XP001030783 cité dans la demande page 79, ligne 5,6 * |
DATABASE BIOSIS [en ligne] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 1987 DE SOUZA C ET AL: "CONTRIBUTION TO THE STUDY OF THE PHARMACOLOGICAL PROPERTIES OF ZINGIBER-OFFICINALE ROSCOE GINGER DETECTION OF ANTIBACTERIAL ACTIVITY" Database accession no. PREV198784074396 XP002180976 & AFRIQUE MEDICALE, vol. 26, no. 251, 1987, pages 201-204, ISSN: 0002-0508 * |
P.H. LIST UND L. H\RHAMME: "Hagers Handbuch der Pharmazeutischen Praxis" , SPRINGER VERLAG , BERLIN, HEIDELBERG, NEW YORK XP002180973 page 572, alinéas 7,8 * page 573, formule Shogaol * * |
P.H. LIST UND L. H\RHAMMER: "Hagers Handbuch der Pharmazeutischen Praxis" , SPRINGER VERLAG , BERLIN, HEIDELBERG, NEW YORK - 1969 XP002180974 page 1234, ligne 26-30 * |
Also Published As
Publication number | Publication date |
---|---|
EP1368012A2 (fr) | 2003-12-10 |
FR2821553A1 (fr) | 2002-09-06 |
CA2442260A1 (fr) | 2002-09-12 |
WO2002070069A3 (fr) | 2003-01-03 |
HUP0303468A2 (hu) | 2004-01-28 |
FR2821553B1 (fr) | 2004-07-23 |
SK11142003A3 (sk) | 2004-09-08 |
PL374103A1 (en) | 2005-09-19 |
CZ20032634A3 (cs) | 2004-06-16 |
US20050238737A1 (en) | 2005-10-27 |
MXPA03008052A (es) | 2004-10-15 |
JP2004522790A (ja) | 2004-07-29 |
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