WO2009121600A2 - Hydroxytyrosol formulations for the treatment and prevention of dna oxidative damages in post-menopausal conditions - Google Patents

Hydroxytyrosol formulations for the treatment and prevention of dna oxidative damages in post-menopausal conditions Download PDF

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Publication number
WO2009121600A2
WO2009121600A2 PCT/EP2009/002416 EP2009002416W WO2009121600A2 WO 2009121600 A2 WO2009121600 A2 WO 2009121600A2 EP 2009002416 W EP2009002416 W EP 2009002416W WO 2009121600 A2 WO2009121600 A2 WO 2009121600A2
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Prior art keywords
extract
formulations
hydroxytyrosol
post
treatment
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PCT/EP2009/002416
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French (fr)
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WO2009121600A3 (en
Inventor
Felicia Cisale
Luciano Villanova
Azzura Villanova
Alessandro Merendino
Gianluca Fasiello
Luigi Villanova
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Lachifarma S.R.L. Laboratorio Chimico Farmaceutico Salentino
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Publication of WO2009121600A2 publication Critical patent/WO2009121600A2/en
Publication of WO2009121600A3 publication Critical patent/WO2009121600A3/en

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    • 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
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
    • A61K31/592—9,10-Secoergostane derivatives, e.g. ergocalciferol, i.e. vitamin D2
    • 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
    • A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
    • A61K31/593—9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
    • 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)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • 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)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/23—Apiaceae or Umbelliferae (Carrot family), e.g. dill, chervil, coriander or cumin
    • A61K36/232—Angelica
    • 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)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
    • A61K36/537—Salvia (sage)
    • 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)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/63—Oleaceae (Olive family), e.g. jasmine, lilac or ash tree
    • 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)
    • A61K36/894—Dioscoreaceae (Yam family)
    • A61K36/8945—Dioscorea, e.g. yam, Chinese yam or water yam
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the present invention relates to compositions comprising hydroxytyrosol (HT) and other biophenols, useful to counteract the DNA oxidative damages in post-menopausal conditions.
  • HT hydroxytyrosol
  • EP 1623960 A process for the preparation of highly pure HT, suitable as an ingredient for use in the pharmaceutical, alimentary and cosmetic fields is disclosed in EP 1623960 in the Applicant's name.
  • EP 1623960 also discloses formulations comprising HT for use in the pharmaceutical, food and cosmetic fields.
  • a number of scientific publications concerning the beneficial activities of hydroxytyrosol and other biophenols are known.
  • Simonetta Salvini et al.- Daily consumption of a high- phenol extra-virgin olive oil reduces oxidative DNA damage in postmenopausal women - British Journal of Nutrition (2006), 95, 742-751] disclose the beneficial effects of a diet rich in extra- virgin olive oil with high HT content in the control of the post-menopausal syndrome.
  • Dioscorea extract - calcium and/or magnesium ions
  • biophenol and/or carotenoid compounds is particularly effective in the treatment and prevention of the oxidative stress, in particular on cell DNA, responsible for the post-menopausal syndrome.
  • the invention therefore relates to pharmaceutical or dietetic formulations containing said combination as the active ingredient.
  • the invention further relates to the use of said combination for the preparation of compositions for the treatment of the post-menopausal syndrome.
  • biophenol means a phenol compound of vegetable origin having antioxidizing activity: examples of said compounds include gallic acid, caffeic acid, tyrosol, catechin, epicatechin, epigallocatechin, quercetin, resveratrol, ellagic acid.
  • carotenoids examples include lutein, lycopene, zeaxanthin, tocopherols.
  • formulations comprising hydroxytyrosol combined with: - Olea europea extracts; extracts of Dioscorea, Angelica sinensis, Salvia officinalis; Passion fruit; caffeic acid, gallic acid, lutein, tyrosol; calcium and/or magnesium ions; and - vitamin D; useful as osteoporosis preventive agents for keeping bone density and solidity constant.
  • the Angelica sinensis extract is useful against hot flashes.
  • the Salvia officinalis extract exerts tonic, stimulating and astringent actions and reduces sweating, particularly night sweats.
  • the Passion fruit extract has sedative activity free from depressant effects, useful in conditions of nervous insomnia, agitation, anxiety, cramps and intestinal pain.
  • the combinations of the invention are particularly effective as they are able to effectively, synergistically control post-menopausal syndrome symptoms and causes.
  • the formulations of the invention are preferably in the form of tablets or similar oral solid forms, which are advantageous in terms of convenience of administration, stability (up to three years or more) and possibility to deliver hydroxytyrosol in much higher amounts than those from the diet intake. It should be noted, indeed, that the hydroxytyrosol content in olive oil can vary depending on the cultivar, pedo-climatic conditions, olive pressing time and techniques, etc. and anyway cannot provide sufficiently high concentrations.
  • hydroxytyrosol content in the formulations of the invention may range from 0.1 to 10 mg per unit dose, while the dosages of the other components may range within wide limits, according to what is known for products comprising such active ingredients.
  • the content in each single component may be comprised within the range of ⁇ 50% of the values reported in the following Examples, which illustrate the invention in greater detail.
  • Tablet comprising HT + Olea europaea dry extract
  • Tablet comprising HT + Olea europaea dry extract + caffeic acid + Passion fruit, Angelica, Salvia and Dioscorea extracts

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  • Health & Medical Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Medical Informatics (AREA)
  • Botany (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Pharmaceutical or dietetic formulations comprising hydroxytyrosol and at least one of the following components: - Angelica sinensis extract; - Salvia officinalis extract; - Passion fruit extract; - Olea europea extract; - Dioscorea extract; - calcium and/or magnesium ions; - vitamin D; - one or more biophenol and/or carotenoid compounds.

Description

HYDROXYTYROSOL FORMULATIONS FOR THE TREATMENT AND PREVENTION OF DNA OXIDATIVE DAMAGES IN POSTMENOPAUSAL CONDITIONS
The present invention relates to compositions comprising hydroxytyrosol (HT) and other biophenols, useful to counteract the DNA oxidative damages in post-menopausal conditions.
Technological Background A process for the preparation of highly pure HT, suitable as an ingredient for use in the pharmaceutical, alimentary and cosmetic fields is disclosed in EP 1623960 in the Applicant's name. EP 1623960 also discloses formulations comprising HT for use in the pharmaceutical, food and cosmetic fields. A number of scientific publications concerning the beneficial activities of hydroxytyrosol and other biophenols are known.
In particular, Simonetta Salvini et al.- Daily consumption of a high- phenol extra-virgin olive oil reduces oxidative DNA damage in postmenopausal women - British Journal of Nutrition (2006), 95, 742-751] disclose the beneficial effects of a diet rich in extra- virgin olive oil with high HT content in the control of the post-menopausal syndrome.
Disclosure of the Invention
It has now been found that a combination of hydroxytyrosol with at least one of the following components: - Angelica sinensis extract;
- Salvia officinalis extract;
- Passion fruit extract;
- Olea europea extract;
- Dioscorea extract; - calcium and/or magnesium ions;
- vitamin D;
- one or more biophenol and/or carotenoid compounds, is particularly effective in the treatment and prevention of the oxidative stress, in particular on cell DNA, responsible for the post-menopausal syndrome.
The invention therefore relates to pharmaceutical or dietetic formulations containing said combination as the active ingredient.
The invention further relates to the use of said combination for the preparation of compositions for the treatment of the post-menopausal syndrome.
In the following, the term "biophenol" means a phenol compound of vegetable origin having antioxidizing activity: examples of said compounds include gallic acid, caffeic acid, tyrosol, catechin, epicatechin, epigallocatechin, quercetin, resveratrol, ellagic acid.
Examples of carotenoids include lutein, lycopene, zeaxanthin, tocopherols.
According to the invention, particularly preferred are formulations comprising hydroxytyrosol combined with: - Olea europea extracts; extracts of Dioscorea, Angelica sinensis, Salvia officinalis; Passion fruit; caffeic acid, gallic acid, lutein, tyrosol; calcium and/or magnesium ions; and - vitamin D; useful as osteoporosis preventive agents for keeping bone density and solidity constant.
The Angelica sinensis extract is useful against hot flashes. The Salvia officinalis extract exerts tonic, stimulating and astringent actions and reduces sweating, particularly night sweats.
The Passion fruit extract has sedative activity free from depressant effects, useful in conditions of nervous insomnia, agitation, anxiety, cramps and intestinal pain.
The combinations of the invention are particularly effective as they are able to effectively, synergistically control post-menopausal syndrome symptoms and causes.
The formulations of the invention are preferably in the form of tablets or similar oral solid forms, which are advantageous in terms of convenience of administration, stability (up to three years or more) and possibility to deliver hydroxytyrosol in much higher amounts than those from the diet intake. It should be noted, indeed, that the hydroxytyrosol content in olive oil can vary depending on the cultivar, pedo-climatic conditions, olive pressing time and techniques, etc. and anyway cannot provide sufficiently high concentrations.
The hydroxytyrosol content in the formulations of the invention may range from 0.1 to 10 mg per unit dose, while the dosages of the other components may range within wide limits, according to what is known for products comprising such active ingredients. In principle, the content in each single component may be comprised within the range of ± 50% of the values reported in the following Examples, which illustrate the invention in greater detail. EXAMPLE 1
Tablet comprising HT
Figure imgf000005_0001
EXAMPLE 2
Tablet comprising HT + Olea europaea dry extract
Figure imgf000005_0002
EXAMPLE 3
Tablet com risin HT + Olea euro aea dr extract + caffeic acid
Figure imgf000006_0001
EXAMPLE 4
Tablet comprising HT + Olea europaea dry extract + caffeic acid + Passion fruit, Angelica, Salvia and Dioscorea extracts
Figure imgf000006_0002

Claims

1. Pharmaceutical or dietetic formulations comprising hydroxytyrosol and at least one of the following components: - Angelica sinensis extract;
- Salvia officinalis extract;
- Passion fruit extract;
- Olea europea extract;
- Dioscorea extract; - calcium and/or magnesium ions;
- vitamin D;
- one or more biophenol and/or carotenoid compounds.
2. Formulations as claimed in claim 1 comprising Olea europea.
3. Formulations as claimed in claim 1 or 2 wherein biophenols and/or carotenoids are selected from caffeic acid, gallic acid, tyrosol.
4. Formulations as claimed in any one of claims 1 to 3 comprising extracts of Dioscorea, Angelica sinensis, Salvia officinalis, Passion fruit.
5. Formulations as claimed in any one of claims 1 to 4 comprising calcium ions, magnesium ions and vitamin D.
6. Formulations as claimed in any one of claims 1 to 5 in the form of tablets.
7. The use of a combination of hydroxytyrosol with at least one of the following components:
- Angelica sinensis extract; - Salvia officinalis extract;
- Passion fruit extract;
- Olea europea extract;
- Dioscorea extract; - calcium and/or magnesium ions;
- vitamin D;
- one or more biophenol and/or carotenoid compounds; for the preparation of compositions for the treatment of the post-menopausal syndrome.
PCT/EP2009/002416 2008-04-04 2009-04-02 Hydroxytyrosol formulations for the treatment and prevention of dna oxidative damages in post-menopausal conditions WO2009121600A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT000589A ITMI20080589A1 (en) 2008-04-04 2008-04-04 HYDROXYSEROSOL FORMULATIONS ONLY FOR THE PREVENTIVE AND CURATIVE TREATMENT OF DAMAGES PRODUCED BY THE OXIDATIVE EFFECTS ON THE DNA IN POST-MENOPAUSAL SITUATIONS
TCMI2008A000589 2008-04-04

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WO2009121600A2 true WO2009121600A2 (en) 2009-10-08
WO2009121600A3 WO2009121600A3 (en) 2010-01-21

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103599239A (en) * 2013-11-01 2014-02-26 于明儒 Traditional Chinese medicine ointment for treating osteoporosis
WO2014161872A1 (en) * 2013-04-05 2014-10-09 Nestec S.A. Compositions for use in stimulating bone growth
IT201900000343A1 (en) * 2019-01-10 2020-07-10 Herbal E Antioxidant Derivatives S R L Ed In Forma Abbreviata H&Ad S R L COMPOSITIONS FOR THE TREATMENT OF MENOPAUSE, OSTEOPENIA AND OSTEOPOROSIS, METABOLIC AND VASCULAR DISORDERS RELATED TO CLIMATER
WO2020229539A1 (en) * 2019-05-13 2020-11-19 Société des Produits Nestlé S.A. Compositions and methods using a combination of calcium and at least one of oleuropein or metabolite thereof
WO2022066513A1 (en) * 2020-09-24 2022-03-31 Mars, Incorporated Food compositions and applications thereof

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EP1623960A1 (en) * 2004-08-06 2006-02-08 Lachifarma SRL Laboratorio Chimico Farmaceutico Salentino Process for the recovery of tyrosol and hydroxytyrosol from oil mill wastewaters and catalytic oxidation method in order to convert tyrosol in hydroxytyrosol
US20070154532A1 (en) * 2003-12-30 2007-07-05 Med Care S.R.L. Compositions comprising vitamins and/or derivatives thereof stablished with olea europea extract and/or ionene polymers
WO2008006581A2 (en) * 2006-07-14 2008-01-17 Dsm Ip Assets B.V. Compositions and use thereof for the treatment, co-treatment or prevention of imflammatory disorders

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US20070154532A1 (en) * 2003-12-30 2007-07-05 Med Care S.R.L. Compositions comprising vitamins and/or derivatives thereof stablished with olea europea extract and/or ionene polymers
EP1623960A1 (en) * 2004-08-06 2006-02-08 Lachifarma SRL Laboratorio Chimico Farmaceutico Salentino Process for the recovery of tyrosol and hydroxytyrosol from oil mill wastewaters and catalytic oxidation method in order to convert tyrosol in hydroxytyrosol
WO2008006581A2 (en) * 2006-07-14 2008-01-17 Dsm Ip Assets B.V. Compositions and use thereof for the treatment, co-treatment or prevention of imflammatory disorders

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SALVINI SIMONETTA ET AL: "Daily consumption of a high-phenol extra-virgin olive oil reduces oxidative DNA damage in postmenopausal women" BRITISH JOURNAL OF NUTRITION, vol. 95, no. 4, April 2006 (2006-04), pages 742-751, XP008114939 ISSN: 0007-1145 cited in the application *
SONI M G ET AL: "Safety assessment of aqueous olive pulp extract as an antioxidant or antimicrobial agent in foods" FOOD AND CHEMICAL TOXICOLOGY, PERGAMON, GB, vol. 44, no. 7, 1 July 2006 (2006-07-01), pages 903-915, XP025065576 ISSN: 0278-6915 [retrieved on 2006-07-01] *
STUPANS I ET AL: "COMPARISON OF RADICAL SCAVENGING EFFECT, INHIBITION OF MICROSOMAL OXYGEN FREE RADICAL GENERATION, AND SERUM LIPOPROTEIN OXIDATION OF SEVERAL NATURAL ANTIOXIDANTS" JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 50, no. 8, 10 April 2002 (2002-04-10), pages 2464-2469, XP001128117 ISSN: 0021-8561 *
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10675290B2 (en) 2013-04-05 2020-06-09 Societe Des Produits Nestle S.A. Compositions for use in stimulating bone growth
CN105050591B (en) * 2013-04-05 2020-08-07 雀巢产品有限公司 Composition for stimulating bone growth
CN105050591A (en) * 2013-04-05 2015-11-11 雀巢产品技术援助有限公司 Compositions for use in stimulating bone growth
JP2016520544A (en) * 2013-04-05 2016-07-14 ネステク ソシエテ アノニム Composition for use in stimulating bone growth
AU2014247122B2 (en) * 2013-04-05 2018-12-06 Société des Produits Nestlé S.A. Compositions for use in stimulating bone growth
JP2020058351A (en) * 2013-04-05 2020-04-16 ソシエテ・デ・プロデュイ・ネスレ・エス・アー Compositions for use in stimulating bone growth
WO2014161872A1 (en) * 2013-04-05 2014-10-09 Nestec S.A. Compositions for use in stimulating bone growth
JP2022031660A (en) * 2013-04-05 2022-02-22 ソシエテ・デ・プロデュイ・ネスレ・エス・アー Composition for use in stimulation of bone growth
US11166965B2 (en) 2013-04-05 2021-11-09 Societe Des Produits Nestle S.A. Compositions for use in stimulating bone growth
CN103599239A (en) * 2013-11-01 2014-02-26 于明儒 Traditional Chinese medicine ointment for treating osteoporosis
WO2020144588A1 (en) * 2019-01-10 2020-07-16 Herbal E Antioxidant Derivatives S.R.L. Ed In Forma Abbreviata H&Ad S.R.L. Compositions for treatment of the menopause, osteopenia and osteoporosis, and menopause/related metabolic and vascular disorders
IT201900000343A1 (en) * 2019-01-10 2020-07-10 Herbal E Antioxidant Derivatives S R L Ed In Forma Abbreviata H&Ad S R L COMPOSITIONS FOR THE TREATMENT OF MENOPAUSE, OSTEOPENIA AND OSTEOPOROSIS, METABOLIC AND VASCULAR DISORDERS RELATED TO CLIMATER
WO2020229539A1 (en) * 2019-05-13 2020-11-19 Société des Produits Nestlé S.A. Compositions and methods using a combination of calcium and at least one of oleuropein or metabolite thereof
WO2022066513A1 (en) * 2020-09-24 2022-03-31 Mars, Incorporated Food compositions and applications thereof

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