WO2024116034A1 - Composition nutraceutique à activité prokinétique avec base d'extrait de gingembre - Google Patents

Composition nutraceutique à activité prokinétique avec base d'extrait de gingembre Download PDF

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Publication number
WO2024116034A1
WO2024116034A1 PCT/IB2023/061844 IB2023061844W WO2024116034A1 WO 2024116034 A1 WO2024116034 A1 WO 2024116034A1 IB 2023061844 W IB2023061844 W IB 2023061844W WO 2024116034 A1 WO2024116034 A1 WO 2024116034A1
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WO
WIPO (PCT)
Prior art keywords
naringin
ginger
nutraceutical composition
composition
naringenin
Prior art date
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PCT/IB2023/061844
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English (en)
Inventor
Valerio MORI
Original Assignee
Petit Medical Group S.R.L.S.
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Filing date
Publication date
Application filed by Petit Medical Group S.R.L.S. filed Critical Petit Medical Group S.R.L.S.
Publication of WO2024116034A1 publication Critical patent/WO2024116034A1/fr

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Classifications

    • 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
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A61K31/33—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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones

Definitions

  • the present description refers to the nutraceutical field and to that of food supplements. More in detail the present invention regards a particular composition with ginger extract base suitably formulated in gel that is characterized in that it comprises a particular quantity of a substance, naringin, with highly prokinetic character. Said composition offers the important advantage of rendering the active principles contained therein particularly bioavailable, resulting especially effective in the treatment of nausea and emesis when taken as is or in association with anti-inflammatory drugs FANS.
  • ginger has digestive properties, capable of intervening in various biological mechanisms.
  • this support action for digestion and for prokinetic capacity of several plant extracts involves multiple biological paths, stimulating receptors of different nature.
  • Gingerols are suspected to have an agonist action on serotonin receptors 5-HT4 but it is admissible to think however that a prokinetic activity attributed to ginger may also depend on the inhibition of Ca ++ L-type channels. There is also evidence of a possible inhibitory interaction of gingerols with regard to the dopamine receptor D2, and also this mechanism is involved in the prokinetic stimulation.
  • naringin and naringenin are agonists for the ghrelin receptor and that its stimulation is correlated to the gastrointestinal motility (Ghrelin receptor is activated by naringin and naringenin, constituents of a prokinetic agent Poncirus fructus).
  • This random trial was designed with a single ascending dose scheme, with quantity that varied between 150 mg and 900 mg of naringenin. The circulating naringenin was then evaluated on serum.
  • the flavonones such as naringin have a glucidic portion that is hydrolyzed by the intestinal bacterial flora (Manach C, Morand C, Gil-Izquierdo A, Bouteloup-Demange C, Remesy C. Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice. Eur J Clin Nutr. 2003;57(2):235-242. [PubMed: 12571654]). This can determine a limiting stage of the process, therefore naringenin was directly used in the study so as to have a quicker absorption.
  • naringenin has indicated that it has a half-life of about 3 hours and is absorbed in circulation in a manner approximately proportional to the dose administered both when fasting and with full stomach and is eliminated from the circulation within 24 hours. It is of interest to indicate that the use of naringin within supplements is allowed, based on that established by different European national laws. Up to now, there are no limiting indications regarding specific warnings to be reported on labels, amount limits, regulations or possible indications.
  • the present description refers to a new nutraceutical composition comprising active ingredients coming from ginger extracts. More in detail the present invention consists of an improved formulation of a similar composition that is already the object of a prior art patent application presented by the Applicant (IT 102021000022673).
  • the composition, object of the present invention is characterized in that it has an increased content of one of the active substances derivable from ginger extracts, and especially an increased added content of naringin.
  • the careful, focused and particular formulation of the composition, object of the invention is based on previous studies and on experiences conducted in the scope of defining the present invention, which have indicated a considerably increase of the prokinetic character of the composition when the naringin content therein is higher.
  • flavonoids including a molecule with high prokinetic action. These molecules are the naringin flavonones - whose presence characterizes the present composition - and its aglycone naringenin. (Identification and Concentration of Some Flavonoid Components in Malaysian Young Ginger (Zingiber officinale Roscoe) Varieties by a High-Performance Liquid Chromatography Method). The content of this molecule in ginger can vary depending on the type of species used, the level of maturation and light exposure. In vitro studies have shown that naringin and naringenin are agonists for the ghrelin receptor and that the its stimulation is correlated with the gastrointestinal motility.
  • Naringin is part of the flavonones and it was discovered that they show strong antiinflammatory and antioxidant activities.
  • naringin is beneficial for the treatment of obesity, diabetes, hypertension and metabolic syndrome.
  • the naringin content is from 20 to 40 times that naturally supplied by the glyceric extract of ginger.
  • ghrelin has a strong stimulating effect on the gastric interdigestive motility in humans and improves the gastric emptying in healthy conditions and in gastroparesis (Prokinetics and fundic relaxants in upper functional GI disorders. Curr Opin Pharmacol. 2008).
  • a ghrelin agonist with prokinetic activity, both central and peripheral, can show a therapeutic potential for the treatment of gastrointestinal transit disturbances. (A Comparison of the Central versus Peripheral Gastrointestinal Prokinetic Activity of Two Novel Ghrelin Mimetics. 2019).
  • ghrelin The effects of ghrelin in man are mainly in the upper gastrointestinal tract, with minimal effects on the transit of the colon (The effects of ulimorelin, a ghrelin agonist, on liquid gastric emptying and colonic transit in humans. 2020).
  • nutraceutical composition with the function of food supplement, with increased prokinetic capacities comprising: sodium alginate, hyaluronic acid, ginger extract, sodium citrate, potassium citrate and an increased content of naringin.
  • Said composition lacks glutins, lactose, parabens, benzoates.
  • composition does not contain glucose, saccharose, fructose or artificial sweeteners such as aspartame or sucralose.
  • Said composition is particularly recommended for the treatment of gastroesophageal reflux, well-known to be characterized by the reascent of the gastric contents into the esophagus.
  • composition carries out a plurality of actions: advantageously its ginger content, titrated in gingerols/shogaols, facilitates the digestion and promotes the prokinetic activity of the stomach; advantageously the citrate content facilitates a prolonged buffer action against stomach acidity; advantageously the presence of alginate opposes the reascending of the gastric acids into the esophagus; advantageously the hyaluronic acid carries out a protective action against the gastric juices and repair action against mucous membrane damage; advantageously, the xanthan gums, even if present, allow a greater adhesivity and effectiveness of the active principles, also allowing optimal palatability.
  • the increased quantity of naringin facilitates a consistent prokinetic action.
  • the present composition has proven to be an effective food supplement, particularly recommended in the treatment of gastroesophageal reflux.
  • FIGURE 1 shows the ghrelin receptor (fig. 1 (a)), and the dopamine receptor D2 (fig. 2(b)).
  • FIGURE 2 shows a schematic representation of how ghrelin stimulates the fatty acid secretion and the motility.
  • FIGURE 3 shows the crystallographic structure of octanoyl-ghrelin. Visible on the right is the n-octanoyl substituted at the serine 3, which is elongated from the backbone.
  • FIGURE 4 shows the activity of naringin and of naringenin by using T-hek293 cells that express the ghrelin receptor and by measuring the variations in the flows of ions [Ca 2+] due to the applications of appropriate agonists.
  • FIGURE 5 shows quattro crystallographic structures of the ghrelin receptor.
  • FIGURE 6 shows the co-crystallized structure of ghrelin and of its receptor.
  • FIGURE 7 shows agonists of the ghrelin receptor: ibutamoren (fig.7 (a)), macimorelin (fig. 7(b)); SM_130686 (fig. 7(c)); anamorelin(fig. 7(d)).
  • FIGURE 8 shows a graph in which it is possible to verify a perfect coherence between pEC50 and BE: the higher the pEC50 value, the lower the calculated energy (which indicates greater affinity).
  • FIGURE 9 shows a graph from which the degree of affinity of naringin and naringenin for the ghrelin receptor is inferred.
  • FIGURE 10 shows the signal trigger sites, cavity 1 (fig. 10 (a)) and cavity 2 (fig, 10(b)), in the ghrelin receptor.
  • FIGURE 11 shows that naringin and naringenin can potentially disturb the same hydrogen bridge by virtue of the exerted steric bulk, as well as due to the hydrophobic characteristics of the structure.
  • FIGURE 12 shows the antagonists of the receptor D2.
  • Amisulpride (fig.13 (a)), domperidone (fig.13 (b)), metoclopramide (fig. 13 (c)), sulpiride (fig. 13 (d)).
  • FIGURE 13 shows the results of the docking for the indicated antagonists and for naringin and naringenin.
  • the present nutraceutical composition is a composition based on alginate, hyaluronic acid, Ginger E.G., sodium citrate, potassium citrate, and naringin.
  • Said composition is characterized in that it comprises an increased amount of naringin, which offers a considerable and surprisingly substantial prokinetic contribution.
  • Said composition was especially defined based on studies and experiments pertaining to the present invention, conducted by researchers working for the Applicant, and described hereinbelow.
  • naringin and naringenin are capable of interacting with the ghrelin receptor and computational studies attest the potentialities thereof with the dopamine receptors D2. (fig 1).
  • the ghrelin receptor (ghrelinR) is the receptor of the anabolic ghrelin hormone. This hormone is also involved in the secretion of the growth hormone (GH), in appetite regulation, in fat accumulation and in energy expenditure.
  • GH growth hormone
  • the natural ligand is ghrelin, a peptide hormone with 28 amino acids.
  • the modification of the fatty acids of ghrelin is essential for the release of the growth hormone induced by ghrelin from the pituitary gland and for appetite stimulation.
  • Fig. (3) Naringin and naringenin
  • naringin of naringenin and of nine other compounds, the researchers used THEK293 cells which express the ghrelin receptor, and they measured the variations in the ion flows [Ca2+] due to the application of appropriate agonists. Among all of the tested compounds, it was found that only naringin (Fig. 4A) and naringenin (Fig. 4C) induce a strong increase of the ions [Ca2+] in cells that express the receptor.
  • the receptor was co-crystallized with ghrelin bonded at its interior; then, precise information is obtained in order to carry out a comparative study with naringin and naringenin.
  • agonists of the ghrelin receptor were used whose experimental EC50 are known, naringin, naringenin, gingerols.
  • the most accredited theory at present for triggering the signal in the receptor regards the two residues Glul24 and His238 present in the cavity 2: in the absence of ghrelin, the two amino acids form a salt bridge that maintains the helixes in a specific conformation. The arrival of n- octanoyl of ghrelin in the cavity 2 perturbs the salt bridge between the two amino acids due to the steric bulk of the hydrophobic chain.
  • naringin and naringenin can potentially perturb the same hydrogen bridge by virtue of the exerted steric bulk as well as of the hydrophobic characteristics of the structure (fig. (11)).
  • the antidopamine agents are clinically exploited for managing gastrointestinal motor disturbances of the upper intestine, including functional dyspepsia, gastric stasis of various origin and emesis.
  • the antidopamine gastrointestinal prokinetics possess antidyspeptic and antiemetic properties.
  • the experimental data of the antagonists of D2 refer to pKi.
  • naringin and naringenin were superimposed on the crystallographic setting of risperidone, an antipsychotic drug for treating schizophrenia. Both naringin and naringenin, in the calculated docking settings, act as imitators of risperidone, in particular naringenin is perfectly superimposed on the terminal part of the risperidone more embedded in the binding cavity.
  • Naringin and naringenin carry out agonist activity on the ghrelin receptor: they act at the molecular level on the ghrelin receptor, mimicking the activity of the natural ligand.
  • Several physical-chemical characteristics of naringin and naringenin are so similar to those of ghrelin that they allow the two agonist molecules to hit the key point (the salt bridge between Glul24 and His238) of activation of the receptor, in the same manner as ghrelin.
  • naringenin and naringenin towards the ghrelin receptor seem to elect naringenin as the most similar molecule by virtue of the bonding energy, whose value is 6 times lower than that of naringin. This is probably due to the reduced dimensions of naringenin and to its more significant hydrophobicity.
  • nutraceutical composition classifiable as a food supplement especially useful for the treatment of gastroesophageal reflux.
  • Said composition based on hyaluronic acid and sodium alginate, comprises ginger E.G., sodium citrate, potassium citrate and is characterized in that it comprises an increased amount of naringin.
  • Said composition has a matrix of xanthan gums that contribute to its formulation in gel.
  • said composition comprises a naringin content that varies between 0.025% and 0.5% by weight. All the components together reach 100% by weight of the composition.
  • said composition comprises, for 15 ml of said composition: 1000 mg of ginger E.G., 600 mg of sodium citrate, 180 mg of potassium citrate, 500 mg of sodium alginate, 100 mg of hyaluronic acid and 30 mg of naringin.
  • the maximum daily dose is 30 ml, corresponding to the content of two bags/sticks.
  • said composition comprises excipients or other pharmaceutically acceptable plant extracts.
  • composition is to be taken after the main meals, like lunch and/or dinner, avoiding the ingestion of liquids in the subsequent half hour.

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  • Health & Medical Sciences (AREA)
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Abstract

L'invention concerne une composition nutraceutique comprenant du gingembre E. G., du citrate de sodium, du citrate de potassium, de l'alginate de sodium, de l'acide hyaluronique, ladite composition étant caractérisée en ce qu'elle comprend une quantité accrue d'additif naringine par rapport à la teneur en naringine déjà présente dans le gingembre E. G.
PCT/IB2023/061844 2022-11-28 2023-11-23 Composition nutraceutique à activité prokinétique avec base d'extrait de gingembre WO2024116034A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104436144A (zh) * 2014-12-11 2015-03-25 渤海大学 一种具有辅助降血糖活性的生姜提取物及制备方法
CN105343116A (zh) * 2015-12-15 2016-02-24 上海壹志医药科技有限公司 柚皮苷的药物用途
CN105902556A (zh) * 2016-04-22 2016-08-31 江西中医药大学 一种基于枳壳中活性成分的组合药物及用途
DE202017100355U1 (de) * 2017-01-24 2017-02-08 Lemon Pharma GmbH & Co. KG Flüssige Ingwerextrakt-Zusammensetzung
WO2021165846A1 (fr) * 2020-02-17 2021-08-26 Neilos S.r.l. Composition pour la protection de la muqueuse gastro-intestinale et pour la prévention et le traitement de maladies associées à celle-ci
IT202100022673A1 (it) 2021-09-01 2023-03-01 Biosolving S R L Composizione gelificata a base di estratto di zenzero

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104436144A (zh) * 2014-12-11 2015-03-25 渤海大学 一种具有辅助降血糖活性的生姜提取物及制备方法
CN105343116A (zh) * 2015-12-15 2016-02-24 上海壹志医药科技有限公司 柚皮苷的药物用途
CN105902556A (zh) * 2016-04-22 2016-08-31 江西中医药大学 一种基于枳壳中活性成分的组合药物及用途
DE202017100355U1 (de) * 2017-01-24 2017-02-08 Lemon Pharma GmbH & Co. KG Flüssige Ingwerextrakt-Zusammensetzung
WO2021165846A1 (fr) * 2020-02-17 2021-08-26 Neilos S.r.l. Composition pour la protection de la muqueuse gastro-intestinale et pour la prévention et le traitement de maladies associées à celle-ci
IT202100022673A1 (it) 2021-09-01 2023-03-01 Biosolving S R L Composizione gelificata a base di estratto di zenzero

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"Safety and Pharmacokinetics of Naringenin: A Randomized, Controlled, Single Ascending Dose", CLINICAL TRIAL, 2020
AKAH PAOLI ANENWEREM NMGAMANEIL K: "Preliminary studies on purgative effect of Carica papaya root extract", FITOTERAPIA, vol. 68, 1997, pages 327 - 331, XP009162228
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GUO LQFUKUDA KOHTA TYAMAZOE Y: "Role of furanocoumarin derivatives on grapefruit juice-mediated inhibition of human CYP3A activity", DRUG METAB DISPOS., vol. 28, no. 7, 2000, pages 766 - 771, XP000972163
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LEIMAN D. A. ET AL: "Alginate therapy is effective treatment for GERD symptoms: a systematic review and meta-analysis", vol. 30, no. 5, 1 May 2017 (2017-05-01), AU, pages 1 - 9, XP055861949, ISSN: 1120-8694, Retrieved from the Internet <URL:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6036656/pdf/dow020.pdf> DOI: 10.1093/dote/dow020 *
MANACH CMORAND CGIL-IZQUIERDO ABOUTELOUP-DEMANGE CREMESY C: "Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice", EUR J CLIN NUTR., vol. 57, no. 2, 2003, pages 235 - 242, XP037762520, DOI: 10.1038/sj.ejcn.1601547
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