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WO2024213970A1 - Composition pour administration orale contenant de la quercétine et de la bromélaïne - Google Patents

Composition pour administration orale contenant de la quercétine et de la bromélaïne Download PDF

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Publication number
WO2024213970A1
WO2024213970A1 PCT/IB2024/053298 IB2024053298W WO2024213970A1 WO 2024213970 A1 WO2024213970 A1 WO 2024213970A1 IB 2024053298 W IB2024053298 W IB 2024053298W WO 2024213970 A1 WO2024213970 A1 WO 2024213970A1
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composition
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Inventor
Sabrina FIORENTINO
Isabella PISANO
Maria Lisa Clodoveo
Filomena CORBO
Marilena MURAGLIA
Anna BORRACCINO
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Sestre SRLS
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • 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
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • 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
    • A61K31/26—Cyanate or isocyanate esters; Thiocyanate or isothiocyanate esters
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/733—Fructosans, e.g. inulin
    • 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
    • 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
    • A61K33/04—Sulfur, selenium or tellurium; Compounds thereof
    • 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
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • 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
    • A61K36/235—Foeniculum (fennel)
    • 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)
    • A61K36/31—Brassicaceae or Cruciferae (Mustard family), e.g. broccoli, cabbage or kohlrabi
    • 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
    • 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
    • A61K36/534—Mentha (mint)
    • 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)
    • A61K36/75—Rutaceae (Rue family)
    • A61K36/752—Citrus, e.g. lime, orange or lemon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/43—Enzymes; Proenzymes; Derivatives thereof
    • A61K38/46—Hydrolases (3)
    • A61K38/48—Hydrolases (3) acting on peptide bonds (3.4)
    • A61K38/4873—Cysteine endopeptidases (3.4.22), e.g. stem bromelain, papain, ficin, cathepsin H
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y304/00—Hydrolases acting on peptide bonds, i.e. peptidases (3.4)
    • C12Y304/22—Cysteine endopeptidases (3.4.22)
    • C12Y304/22004—Bromelain (3.4.22.4)

Definitions

  • the present invention relates to a composition for oral use comprising a combination of nutraceutical molecules such as Quercetin and Bromelain .
  • the composition of the present invention is used as a prebiotic and anti-inflammatory agent for the treatment of chronic inflammatory pathologies , such as endometriosis .
  • endometriosis is a chronic and recurrent , estrogen-dependent inflammatory disease , characteri zed by the presence of endometrial tissue in ectopic sites . It signi ficantly compromises the women quality of li fe , as it is characteri zed by very painful symptoms represented above all by dysmenorrhea, dyspareunia, dyschetia and chronic disabling pelvic pain, which af flicts especially young women causing serious physical discomfort , relational and emotional di f ficulties . Endometriosis is characteri zed by a multi factorial etiology which sees a close interrelationship between genetic, metabolic, environmental and immune factors.
  • f endometriosis Among the most common symptoms o f endometriosis are : intestinal disorders , dyschetia and constipation .
  • antioxidants in the treatment of endometriosis can inhibit the proli feration of endometrial cells in adenomyosis and reduce their mobility and invasiveness .
  • These inhibitory effects may be related to the under regulation of MMP2, MMP9 proteins
  • Dietary compounds are the main components that regulate gene expression via epigenetic mechanisms such as DNA methylation and histone modification via histone-acetyltransf erases (HAT) and histonedeacetylases (HDAC) .
  • HAT histone-acetyltransf erases
  • HDAC histonedeacetylases
  • quercetin is a naturally occurring polyphenolic flavonoid. Known for its antioxidant, anti-inflammatory, antiproliferative and anticancer effects, it has shown great benefits in the treatment of cancer and endometriosis, without obvious side effects. Quercetin is present in apples, onions and citrus fruits. It can activate the enzyme sirtuin-1 NAD-dependent deacetylase (SIRT1) and NAD-dependent deacetylase. It is able to inhibit the expression of tumor necrosis factor ( TNF) -induced interferon gamma ( IFNy) -inducible protein 10 (IP10) and macrophage inflammatory protein 2 (MIP2 ) .
  • TNF tumor necrosis factor
  • IFNy interferon gamma
  • MIP2 macrophage inflammatory protein 2
  • H3 histones blocks posttranslational modi fications ( acetylation and phosphorylation) of H3 histones through the induction of p300/CBP . Consequently, promoters of proinf lammatory genes associated with H3 histones are af fected by inhibition of cofactor recruitment at the chromatin level . Furthermore , through inhibition of HDAC and DNMT1 , quercetin inhibits the cell cycle and consequently induces apoptosis , suppressing tumor growth and angiogenesis (NagisaNosrati , Int . J . Mol . Sci . 2017 , 18 , 2050 ) .
  • quercetin treatment can therefore prevent oxidatively mediated cell damage induced by an infectious , inflammatory or autoimmune mechanism .
  • proteolytic enzymes exert notable ef fects on the barrier function of cell monolayers of the Caco-2 human colorectal adenocarcinoma line , facilitating the transport of normally non-absorbable compounds . This suggests that the reported, but so far unexplained, systemic absorption of proteolytic enzymes after oral administration in vivo may also occur by sel f-enhanced paracellular transport
  • the obj ect of the present invention is a composition for oral use and comprising a mixture , the components of which are at least quercetin and bromelain for the treatment of chronic inflammatory pathologies such as endometriosis or irritable bowel syndrome ( IBS ) .
  • the speci fic composition of the present invention is used as a nutraceutical and antiinflammatory agent .
  • this composition promotes an antioxidant and anti-inflammatory activity which acts on compromised biochemical pathways through a physiological approach, constant over time which counteracts/reduces chronic inflammation .
  • this composition acts on symptoms collateral to the pathology, such as intestinal disorders in the case of endometriosis as the use of nutraceuticals is a valid innovative therapeutic tool for the treatment of all conditions characteri zed by neuroinflammation and chronic painful states , in the absence of side ef fects .
  • composition for oral use is defined, as speci fied in the attached independent claim .
  • FIG. 1 shows the diagram relating to the growth curve of SaccaromycesCerevisiae as a model for studying oxidative stress , according to known technique ;
  • FIG. 2 shows the diagram relating to the tests carried out on the growth of Saccaromyces Cerevisiae in the presence of the composition in two di f ferent concentrations , which is the obj ect of the present invention
  • FIG. 3 shows the diagram relating to the growth curve of Saccaromyces Cerevisiae according to a first concentration of the composition obj ect of the present invention
  • FIG. 4 shows the diagram relating to the growth curve of Saccaromyces Cerevisiae according to a second concentration of the composition object of the present invention
  • FIG. 6 shows the analysis of cell viability in flow cytometry, defined by a gate fixed on the basis of the FCS (forward scatter - frontal dispersion) and the SSC (side scatter - lateral dispersion - SSC_Q2) , according to the present invention
  • FIG. 7 shows the identification of the three cell populations, analyzed after staining with 7AAD in flow cytometry via a density plot as a function of FSC according to the present invention
  • FIG. 8A-D shows the graph of the cell viability analysis performed by flow cytometry by staining 7AAD.
  • 8A samples stimulated with LPSvs . unstimulated samples
  • 8B samples treated with A, B, A+B + LPS vs. Ctrl+ LPS
  • 8C samples treated with A+B + LPS vs.
  • FIG. 9A-C shows the structure of H2DCFDA (9A) and its reaction products of hydrolysis of the acetyl groups (9B) and oxidation (9C) which leads to the formation of a fluorescent compound which allows the production of ROS to be estimated, according to the present invention
  • FIG. 10 shows the analysis of intracellular ROS production, using a "density plot vs FSC" which analyzes cells selected with the initial gate based on their physical characteristics, according to the present invention
  • FIG. 11 A-B shows the analysis of intracellular ROS production, calculated on a reference histogram (11A) which analyzes cells selected with the initial gate through a quantification of the MFI (11B) with the indicated treatments in basal conditions and in the presence of a pro-inflammatory stimulus
  • a samples stimulated with LPS vs. unstimulated samples:
  • b samples treated with A, B, A+B + LPS vs. Ctrl + LPS. **p ⁇ 0.01, ***p ⁇ 0.001, according to the present invention
  • FIG. 12 shows the analysis of intracellular ROS production (DCF+ cells) in relation to the percentage of dead (12A) and live (12B) cells in the indicated treatments in basal conditions and in the presence of a pro-inflammatory stimulus, a: samples stimulated with LPS vs. unstimulated samples; b: samples treated with A, B, A+B + LPS vs. Ctrl + LPS. **p ⁇ 0.01, ***p ⁇ 0.001, according to the present invention.
  • composition for oral use comprising at least quercetin (2 (3,4 Dihydroxyphenyl) 3, 5, 7trihydroxy4Hl benzopyran-4-one dihydrate) from Alliumcepa L. titrated 30% in Quercetin-100 mcg and bromelain 2500 GDU- 60 mcg.
  • quercetin (3,4 Dihydroxyphenyl) 3, 5, 7trihydroxy4Hl benzopyran-4-one dihydrate
  • the composition further comprises at least one further active compound: for example Inulin, Citrus Aurantium dry extract tit. 6% Synephrine, Artichoke dry extract tit. 5% chlorogenic acid, Broccoli dry extract tit. 0.3%-0.5% Sulforaphane, Melissa officinalis dry extract tit. 4% rosmarinic acid, Quercetin, Mentha piperita dry extract, Fennel dry extract tit. 1% Essential Oil, Selenium and Chromium .
  • at least one further active compound for example Inulin, Citrus Aurantium dry extract tit. 6% Synephrine, Artichoke dry extract tit. 5% chlorogenic acid, Broccoli dry extract tit. 0.3%-0.5% Sulforaphane, Melissa officinalis dry extract tit. 4% rosmarinic acid, Quercetin, Mentha piperita dry extract, Fennel dry extract tit. 1% Essential Oil, Selenium and Chromium .
  • the presence of further active compounds guarantees the balance of the Microbiota, the presence of Inulin for example favors the proli feration of some bacterial strains which contribute to the synthesis of some Enzymes , such as glucuronidase , which regulate the levels of circulating estrogens and therefore contribute to the regulation of the hormonal profile .
  • the composition further comprises at least one inactive excipient : for example calcium phosphate inactive , magnesium stearate inactive and silicon dioxide inactive .
  • excipients for example inactive Mg and/or silicon dioxide
  • inactive Mg and/or silicon dioxide are used as anti-caking agents , or for the purpose of guaranteeing smoothness and stability during the production phase .
  • the composition for oral use is in the form of capsules or soluble powder contained in a special sachet .
  • a preferred composition for oral use for a 700 mg capsule is , for example , shown in
  • Table 1 where the dosages refer to two capsules .
  • excipients contained in the composition according to the present invention contribute to the above-mentioned advantages .
  • excipients for a 700 mg capsule are , for example : inactive calcium phosphate in a weight quantity of
  • the recommended dose is equal to two capsules per day .
  • the composition obj ect of the present invention is also used for the preparation of a food supplement , for the treatment of inflammatory disorders of the intestinal tract .
  • Gender di fferences have implications for human health, risk of assessment and toxicology .
  • the first concentration includes Quercetin 15 mg and Bromelain 10 mg (COMBO C) and the second concentration includes Quercetin 5 mg and Bromelain 20 mg (COMBO E) in presence of 2mM H2O2.
  • Figures 3 and 4 show the effect of the two concentrations of Quercetin and Bromelain (COMBO C and COMBO E) on the growth of Saccaromyces Cerevisiae, in the presence of a 2mM H2O2 oxidizing agent.
  • the concentrations tested are 0.04 (1) and 0.08 (2) g/L. Both concentrations demonstrated an improving effect on the growth of Saccaromyces Cerevisiae colonies.
  • FIG. 5 shows the comparison diagram between the effect of the two concentrations of Quercetin and Bromelain in the two concentrations used for the tests (COMBO C and COMBO E) .
  • the second concentration (COMBO E) includes Quercetin 5 mg and Bromelain 20 mg and is the one that significantly reduces the production of reactive oxygen species (ROS) in Saccaromyces Cerevisiae yeast cells in presence of a 2mM H2O2 oxidizing agent, at a concentration tested at 0.04 g/L.
  • ROS reactive oxygen species
  • the fluorescence was evaluated for the 7AAD which has an excitation/emission wavelength of 546/ 647 nm, respectively .
  • the fluorescence emitted in the far red allowed to identify, in a density plot as a function of the FSC, three distinct populations: one negative (7AAD-) and one positive for 7AAD within which 2 subpopulations are distinguished, one with an intermediate fluorescence (7AADint. and one with a higher fluorescence (7AAD+) . It is likely that these three populations, identified in terms of percentage, refer, in order, to live cells (Live cells) , to cells that are dying (Dying cells) and dead cells (Dead cells) ( Figure 7) .
  • Fluorescence analysis will provide an estimate of the levels of ROS produced by the cells . This analysis can be done using different detection systems; in our case, the system chosen was the flow cytometer. Also for this analysis, an initial gate was defined based on the FCS and SSC on which the expression of DCF was evaluated in percentage terms through a density plot (DCF+ cells vs FSC, Figure 10) and in terms of median fluorescence (MFI) using a histogram ( Figure 11A) .
  • the MFI analysis demonstrates that, although the compound B in the presence of LPS is the only one, like untreated cells, which is capable of increasing ROS production compared to its reference sample not stimulated with LPS ( Figure 11B, a) , this modulation is much less relevant in terms of the median fluorescence analyzed. In fact, comparing the results obtained following stimulation with LPS, cells treated with the A+B combination and its single components (including B) significantly reduce the MFI of DCF compared to untreated cells ( Figure 11B, b) .
  • the A+B combination although demonstrating an antioxidant ef fect in the presence of a pro-inflammatory stimulus , does not present , at least at the tested dosage , a synergistic action as it does not confer an additional benefit compared to the administration of the individual components .

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Abstract

L'invention concerne une composition pour une administration orale contenant un mélange dont les composants sont au moins la quercétine et la bromélaïne, utilisée pour le traitement de pathologies inflammatoires chroniques, ladite composition étant caractérisée en ce que la quercétine et la bromélaïne sont présentes ensemble dans une proportion respectivement égale à 5:3.
PCT/IB2024/053298 2023-04-11 2024-04-04 Composition pour administration orale contenant de la quercétine et de la bromélaïne Pending WO2024213970A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT102023000006855 2023-04-11
IT102023000006855A IT202300006855A1 (it) 2023-04-11 2023-04-11 Composizione per uso orale

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080031980A1 (en) * 2006-08-02 2008-02-07 Al Rodriguez Curcumin-containing composition, methods of making, and methods of using
WO2011063394A2 (fr) * 2009-11-23 2011-05-26 Olmstead Stephen F Compositions et méthodes comprenant une peptidase serratia destinées à l'inhibition et au traitement de biofilms liés à certaines pathologies
EP3338769A1 (fr) * 2016-12-20 2018-06-27 Inpha Duemila S.r.l. Formulations utilisées dans le traitement de l'endométriose et des troubles associés

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080031980A1 (en) * 2006-08-02 2008-02-07 Al Rodriguez Curcumin-containing composition, methods of making, and methods of using
WO2011063394A2 (fr) * 2009-11-23 2011-05-26 Olmstead Stephen F Compositions et méthodes comprenant une peptidase serratia destinées à l'inhibition et au traitement de biofilms liés à certaines pathologies
EP3338769A1 (fr) * 2016-12-20 2018-06-27 Inpha Duemila S.r.l. Formulations utilisées dans le traitement de l'endométriose et des troubles associés

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
COLOSIMO S ET AL: "Supplementation with Anti-inflammatory Nutraceutical Products in the Management of Chronic Pelvic Pain: A Narrative Review", CURRENT TOPICS IN NUTRACEUTICAL RESEARCH, vol. 20, no. 2, May 2022 (2022-05-01), pages 265 - 275, XP093107076 *
GIANNINI A ET AL: "Effects of preoperative and perioperative administration of Wobenzym Vital on minimal-mild endometriosis", JOURNAL OF ENDOMETRIOSIS AND PELVIC PAIN DISORDERS 20150401 WICHTIG PUBLISHING SRL ITA, vol. 7, no. 2, 1 April 2015 (2015-04-01), pages 71 - 77, XP093107156, ISSN: 2284-0265 *
JOEL EVANS: "An Integrative Approach to Fibroids, Endometriosis, and Breast Cancer Prevention", INTEGRATIVE MEDICINE @BULLET, 1 October 2008 (2008-10-01), XP055415582, Retrieved from the Internet <URL:http://www.imjournal.com/resources/web_pdfs/popular/1008_evans.pdf> [retrieved on 20171013] *

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