WO2021129977A1 - Extraits végétaux destinés au traitement d'une vascularité accrue du visage - Google Patents

Extraits végétaux destinés au traitement d'une vascularité accrue du visage Download PDF

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Publication number
WO2021129977A1
WO2021129977A1 PCT/EP2020/082154 EP2020082154W WO2021129977A1 WO 2021129977 A1 WO2021129977 A1 WO 2021129977A1 EP 2020082154 W EP2020082154 W EP 2020082154W WO 2021129977 A1 WO2021129977 A1 WO 2021129977A1
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Prior art keywords
extract
cosmetic
pharmaceutical formulation
alpinia officinarum
treatment
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PCT/EP2020/082154
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English (en)
Inventor
Nahid Amini
Christina ÖSTERLUND
Michele Leonardi
Virginie LAFON-KOLB
Ia KHMALADZE
Lene VISDAL-JOHNSEN
Susanne FABRE
Nina HRAPOVIC
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Oriflame Cosmetics Ag
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Priority to CN202080079455.0A priority Critical patent/CN115209868A/zh
Priority to EP20807385.8A priority patent/EP4081181A1/fr
Publication of WO2021129977A1 publication Critical patent/WO2021129977A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/005—Preparations for sensitive skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
    • 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
    • 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
    • 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)
    • A61K36/70—Polygonaceae (Buckwheat family), e.g. spineflower or dock
    • A61K36/704—Polygonum, e.g. knotweed
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom

Definitions

  • the present invention provides an extract of Alpinia officinarum for the treatment of increased facial vascularity.
  • the present invention further provides a cosmetic or pharmaceutical formulation for use in the treatment of increased facial vascularity, and a method for production of the formulation.
  • Rosacea is a common, but poorly understood, long-term, chronic skin condition that occurs mainly on the face, typically on the nose, cheeks and forehead. The causes of rosacea are unknown and there is currently no cure.
  • Rosacea is a relapsing condition, which means that a patient may experience periods of time where the symptoms lessen or disappear altogether, and then the symptoms return.
  • rosacea There are four subtypes of rosacea including: erythematotelangiectactic rosacea (ETR) which is associated with facial redness, flushing and visible blood vessels; papulopustular rosacea which is associated with acne-like breakouts; rhinophyma which is associated with thickening of the skin on the nose; and ocular rosacea which is associated with symptoms on the eye area.
  • ETR erythematotelangiectactic rosacea
  • papulopustular rosacea which is associated with acne-like breakouts
  • rhinophyma which is associated with thickening of the skin on the nose
  • ocular rosacea which is associated with symptoms on the eye area.
  • Rosacea can be controlled to some degree with long term treatment using conventional medications. However, the changes in appearance caused by rosacea can have a significant psychological impact on the patient, such as for example causing a loss in confidence.
  • KLKs human kallikrein-related peptidases
  • KLK5 kallilkrein-5
  • KLK7 kallikrein-7
  • KLK5 kallikrein-5
  • these peptides In lesional rosacea skin, kallikrein-5 (KLK5) levels are increased, leading to increased levels of both LL- 37 and its proteolytic fragments.
  • KLK5 levels and LL-37 and its proteolytic fragments In addition to the increased abundance of KLK5 levels and LL-37 and its proteolytic fragments, these peptides also differ from those found in normal individuals. Unlike normal LL-37 peptide fragments, these abnormal peptides control functions, such as leukocyte chemotaxis, angiogenesis, and expression of extracellular matrix components.
  • the increased levels of LL-37 and other peptides induce the clinical manifestations seen in rosacea, including inflammation and increased facial vascularity.
  • a cosmetic or pharmaceutical formulation for use in the treatment of rosacea with improved efficacy compared to conventional medications.
  • a cosmetic or pharmaceutical formulation which is capable of blocking the activity or inhibiting the production of kallikrein-5 (KLK5).
  • KLK5 kallikrein-5
  • the formulation should also reduce and/or prevent the formation of LL-37 and abnormal peptide fragments, thereby inhibiting a major cascade of inflammation that has been found to be correlated with major clinical findings in rosacea.
  • Alpinia officinarum also known as lesser galangal, is indigenous to Southeast China (Guangdong, Guangxi, Hainan) and Indochina. Alpinia officinarum belongs to the Zingiberaceae family and is a perennial herb with thick, creeping reddish-brown rhizomes, lineolate acuminate ornamental leaves, and showy white flowers in racemes.
  • the extract of Alpinia officinarum is used in the treatment of rosacea.
  • the extract of Alpinia officinarum is an inhibitor of kallikrein-5 (KLK5).
  • the extract of Alpinia officinarum has been found to be able to treat increased vascularity, and in particular symptoms of rosacea, including inflammation and increased facial vascularity, with improved efficacy compared to conventional medications.
  • the extract of Alpinia officinarum has been found to be capable of blocking the activity or inhibiting the production of kallikrein-5 (KLK5), which consequently reduces and/or prevents the formation of LL-37 and abnormal peptide fragments, thereby inhibiting a major cascade of inflammation that has been found to be correlated with major clinical findings in rosacea.
  • KLK5 kallikrein-5
  • the extract of Alpinia officinarum preferably comprises one or more of: kaempferol, galangin, quercetin, pinocembrin, dihydrogalangin, 3-O-methylgalangin, 7-O-methylgalangin, kaempferide, 5- hydroxy-7-(4'-hydroxy-3'-methoxyphenyl)-l-phenyl-3-heptanone, 3,5-dihydroxy-l,7-bi-(3,4- dihydroxyphenyl)heptane, alpinin B, galangin 7-glucoside or any combination thereof.
  • the extract of Alpinia officinarum may be provided in the form of a cosmetic or pharmaceutical formulation for use in the treatment of increased facial vascularity, such as for example in the treatment of rosacea (e.g. in the treatment of symptoms associated with rosacea including for example inflammation and increased facial vascularity).
  • the extract is preferably an extract of the root of Alpinia officinarum.
  • a cosmetic or pharmaceutical formulation comprising a combination of at least two different components selected from: an extract of Alpinia officinarum, myricetin, lobaric acid, and an extract of Persicaria capitata (PCA).
  • the extract is preferably an extract of the root of Alpinia officinarum and/or Persicaria capitata.
  • the cosmetic or pharmaceutical formulation comprises an extract of Alpinia officinarum and myricetin.
  • the cosmetic or pharmaceutical formulation comprises an extract of Alpinia officinarum and lobaric acid.
  • the cosmetic or pharmaceutical formulation comprises an extract of Alpinia officinarum, and an extract of Persicaria capitata.
  • the cosmetic or pharmaceutical formulation comprises myricetin and lobaric acid.
  • the cosmetic or pharmaceutical formulation comprises lobaric acid and an extract of Persicaria capitata.
  • the cosmetic or pharmaceutical formulation comprises myricetin and an extract of Persicaria capitata.
  • a cosmetic or pharmaceutical formulation as herein described in the treatment of skin inflammation, preferably in the treatment of increased facial vascularity, such as for example in the treatment of rosacea.
  • the cosmetic or pharmaceutical formulation as herein described is used as a kallikrein-5 (KLK5) inhibitor.
  • KLK5 kallikrein-5
  • a method for the production of a cosmetic or pharmaceutical formulation as herein described comprising: obtaining at least two sources of at least two different components selected from: an extract of Alpinia officinarum, myricetin, lobaric acid, and an extract of Persicaria capitata; and combining the at least two components to provide a cosmetic or pharmaceutical formulation.
  • a kit for the production of a cosmetic or pharmaceutical formulation as described herein comprising: at least two sources of at least two different components selected from: an extract of Alpinia officinarum, myricetin, lobaric acid, and an extract of Persicaria capitata.
  • Figures 1A-C illustrates the UFIPLC/Q-ToF-MS chromatograms of three extracts of Alpinia officinarum (ALO);
  • Figure 1A illustrates the UFIPLC/Q-ToF-MS chromatogram of a methanol extract of Alpinia officinarum (ALO);
  • Figure IB illustrates the UFIPLC/Q-ToF-MS chromatogram of a water extract of Alpinia officinarum (ALO).
  • Figure 1C illustrates the UHPLC/Q-ToF-MS chromatogram of an ethanol-water extract of Alpinia officinarum (ALO);
  • Figure 2 illustrates the UHPLC/Q-ToF-MS chromatogram of a methanol extract of Alpinia officinarum and the identified compounds within the extract;
  • Figure 3 is an isobologram illustrating model lines of synergism and antagonism
  • Figure 4 illustrates the percentage inhibition of the enzyme Kallikrein 5 by pure compounds and extracts
  • Figure 5 is an isobologram for formulations comprising a combination myricetin/A/p/n/a officinarum (ALO);
  • Figure 6 is an isobologram for formualtions comprising a combination of Alpinia officinarum (ALO) and Persicaria capitata (PCA);
  • ALO Alpinia officinarum
  • PCA Persicaria capitata
  • Figure 7 illustrates gene expression of AQP3, CASP14, and CLDN1 after 24h treatment of keratinocytes with IOmM myricetin. Treatment was compared to vehicle treated sample which was put to 1. Statistics were performed in PRISM 5 where Repeated measurement one-way ANOVA was used on the ACt values with Dunnett's post hoc test were p* ⁇ 0.05, p** ⁇ 0.01 and p*** ⁇ 0.001; Figure 8 illustrates anti-inflammatory activity in PAR2 induced proinflammatory IL-8 model using FlaCaT cells; and
  • Figure 9 illustrates myricetin anti-inflammatory activity in IL-lbeta induced inflammation model in dermal microvascular endothelial (DMVEC) cells.
  • the root of the plant material ( Alpinia officinarum) was extracted using three different solvents: methanol; water; and 50:50 ethanohwater mixture.
  • Table 1 shows the extraction yields of Alpinia officinarum using the three different solvents: Table 1
  • KLK5 Fluman tissue Kallikrein 5
  • hK5 also known as stratum corneum tryptic enzyme
  • KLK5 regulate cell shedding (desquamation) in conjunction with KLK7 and KLK14 given its ability to degrade proteins which form the extracellular component of cell junctions in the stratum corneum.
  • the activity of the enzyme KLK5 is measured by its ability to cleave the fluorogenic peptide substrate Boc-VPR-AMC.
  • the primary screening assays are performed according to the validated standard protocol i.e. SP-SR- 201-v3 for KLK5 enzyme inhibition Assay.
  • the combinations of active components within a formulation are performed according to the validated standard protocol i.e. SP-SR-234 for Isobologram Analysis.
  • the first step is to determine the IC 50 s of each of the individual active components (i.e. active component A and active component B) within the formulation of the present invention.
  • the additive isobole for 50% inhibition is then traced on Graph Pad Prism as shown in Figure 3.
  • the concentration of active component B that will give 50% inhibition is interpolated with a chosen concentration of active component A.
  • the combination of the two active components A and B at these concentrations needs to then be screened.
  • Figure 4 illustrates the % inhibition of Kallikrein 5 for a number of active components and plant extracts including lobaric acid, myricetin, Alpinia officinarum (ALO) and Persicaria capitata (PCA).
  • Lobaric acid, myricetin, Alpinia officinarum (ALO) and Persicaria capitata (PCA) were found to show a very good percentage inhibition of KLK5 and the IC 5 oS of each of these active components and extracts were determined and the results are shown in Table 4.
  • Example 4 Formulation comprising two active components: myricetin and an extract of Alpinia officinarum
  • the isobologram of Figure 5 shows that the IC 50 values for the inhibition of kallikrein-5 of a number of different formulations of the present invention comprising myricetin and an extract of Alpinia officinarum. It can be seen from the isobologram that the IC 50 values of the formulations of the present invention are below the additive isobole, and as such it can be seen that the formulations of the present invention comprising a combination of myricetin and an extract of Alpinia officinarum provide a synergistic effect on the KLK5 inhibition activity.
  • Example 5 Formulation comprising two active components: an extract of Alpinia officinarum and PCA
  • the isobologram of Figure 6 shows that the IC 50 values for the inhibition of kallikrein-5 of a number of different formulations of the present invention comprising an extract of Alpinia officinarum and PCA. It can be seen from the isobologram that the IC 50 values of the formulations of the present invention are below the additive isobole, and as such it can be seen that the formulations of the present invention comprising a combination of an extract of Alpinia officinarum and PCA provide a synergistic effect on the KLK5 inhibition activity.
  • Example 6 Formulations comprising two active components selected from lobaric acid together with either an extract of Alpinia officinarum; an extract of Persicaria capitata; or myricetin
  • ALO extract of Alpinia officinarum and
  • PCA Persicaria capitata
  • myricetin were found to provide higher than 50% inhibition of kallikrein-5.
  • formulations of the present invention comprising a combination of lobaric acid with an extract of Alpinia officinarum (ALO), an extract of Persicaria capitata or myricetin has a synergistic effect on the ability of the formulation to inhibit production of KLK5 as shown in Tables 5 and 6.
  • the extracts and formulations of Examples 3 to 6 have been found to produce improved inhibition of kallikrein-5, and to have a synergistic effect on the inhibition of kallikrein-5.
  • the extracts and formulations of the present invention have therefore been shown to have improved efficacy for the treatment of symptoms associated with rosacea, such as for example inflammation and increased facial vascularity.
  • Barrier genes that were analysed were OCLN, AQP3 CLDN1, IVL, CASP14, KRT1, KRT10, FLG, PNPLA and TJP1. qPCR was used to analyze the gene expression of barrier genes.
  • Human epidermal keratinocytes (KC) were cultured in 48-well plates and treated for 24h with actives before RNA extraction followed by cDNA synthesis and then qPCR was performed for the wanted genes.
  • GAPDH was used as the housekeeping gene.
  • FIG. 7 shows that treatment with myricetin (lOpm) after 24 hours upregulated three barrier genes (AQP3, CASP14 and CLDN1) which were statistically significant when compared to the vehicle treated samples. An increase in gene expression is indicative of improvement of skin barrier in the skin.
  • Example 8 Effect of Lobaric acid as an anti-inflammatory agent
  • TRPV1 is an important ion channel and it has been shown that it is overexpressed in sensitive skin. TRPV1 can be activated directly or indirectly via PAR2. Targeting TRPV1 via PAR2 can be done in vitro by using PAR2 specific agonistic peptide (SLIGKV-NH2) leading to inflammatory IL-8 secretion.
  • PAR2 specific agonistic peptide SLIGKV-NH2
  • the aim of the study was to induce inflammatory response by targeting PAR2 in HaCaT keratinocyte cell line and test the anti-inflammatory potential of Lobaric acid (L.A) to inhibit PAR2 driven IL-8.
  • L.A Lobaric acid
  • Figure 8 provides IL-8 ELISA results (of the following groups: UT (untreated), PAR2 Ago (PAR2 stimulation with agonistic peptide), PAR2 + Antago (control, to decrease PAR2 expression with antagonistic peptide pretreatment), PAR2 + Lobaric acid (L.A pretreatment prior to PAR2 stimulation)) which illustrate representative data of two identical independent experiments.
  • PAR 2 induces IL-8 upregulation in HaCaT cells and the positive control PAR2 antagonist peptide significantly down regulates it.
  • Lobaric acid significantly inhibited PAR2 induced IL-8 and therefore is considered to be useful in the treatment of sensitive skin associated with inflammation.
  • HMVEC Human microvascular endothelial cells
  • Figure 9 illustrates IL-8 ELISA results for the following groups: UT (untreated), IL-lb (recombinant IL- lb stimulation), IL-lb + M (IL-lb + Myricetin) induced with IL-lb.
  • IL-lb induces IL-8 upregulation in HMVEC and Myricetin pretreatment, significantly inhibits cytokine induction.
  • myricetin has been shown to be useful in the treatment of sensitive skin redness associated with proinflammatory cytokines.

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Abstract

La présente invention concerne l'utilisation d'un extrait d'Alpinia officinarum dans le traitement d'une vascularité accrue du visage. La présente invention concerne également une formulation cosmétique ou pharmaceutique comprenant une association d'au moins deux constituants actifs différents choisis parmi : un extrait d'Alpinia officinarum, la myricétine, l'acide lobarique et un extrait de Persicaria capitata, et son utilisation dans le traitement d'une vascularité accrue du visage. La présente invention concerne également un procédé de production d'une formulation cosmétique ou pharmaceutique comprenant une association d'au moins deux constituants actifs différents choisis parmi : un extrait d'Alpinia officinarum, la myricétine, l'acide lobarique et un extrait de Persicaria capitata.
PCT/EP2020/082154 2019-12-23 2020-11-13 Extraits végétaux destinés au traitement d'une vascularité accrue du visage WO2021129977A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202080079455.0A CN115209868A (zh) 2019-12-23 2020-11-13 用于治疗面部血管分布提高的植物提取物
EP20807385.8A EP4081181A1 (fr) 2019-12-23 2020-11-13 Extraits végétaux destinés au traitement d'une vascularité accrue du visage

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SE1930415.3 2019-12-23
SE1930415A SE544843C2 (en) 2019-12-23 2019-12-23 Plant extracts for treatment of rosacea

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WO2021129977A1 true WO2021129977A1 (fr) 2021-07-01

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