WO2015102478A1 - Composition bioactive ayant des propriétés photoprotectrices naturelles contre les uv - Google Patents

Composition bioactive ayant des propriétés photoprotectrices naturelles contre les uv Download PDF

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Publication number
WO2015102478A1
WO2015102478A1 PCT/MY2014/000271 MY2014000271W WO2015102478A1 WO 2015102478 A1 WO2015102478 A1 WO 2015102478A1 MY 2014000271 W MY2014000271 W MY 2014000271W WO 2015102478 A1 WO2015102478 A1 WO 2015102478A1
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WIPO (PCT)
Prior art keywords
extract
mixture
curcuma
bioactive composition
active fraction
Prior art date
Application number
PCT/MY2014/000271
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English (en)
Inventor
Zanariah UJANG
Ahmad Hazzi AB RASHID
Mazita MOAHD DIAH
Thavamanithevi Subramaniam
Harmayumi WAHID
Suzaini BADRUDIN
Siti Kasmarizawaty SUBOH
Badariah ABDULLAH
Original Assignee
Sirim Berhad
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Sirim Berhad filed Critical Sirim Berhad
Publication of WO2015102478A1 publication Critical patent/WO2015102478A1/fr

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Classifications

    • 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]
    • A61K8/9794—Liliopsida [monocotyledons]
    • 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)
    • 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)
    • A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
    • 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
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the present invention relates to a bioactive composition
  • a bioactive composition comprising an extract, active fraction or mixture thereof of a species from the ginger family (Zingiberaceae) for use against the damaging effects of ultraviolet (UV) radiation.
  • the damaging effects of sunlight on skin are well documented. Some scientists estimate that over 70% of the damage that the sun inflicts on the average person's skin over a lifetime is the result of simply being outdoors or even sitting by a window.
  • the major short term hazard of prolonged exposure to sunlight is erythema.
  • the long term hazard of ultraviolet radiation is premature aging of the skin which is characterized by wrinkling and yellowing of the skin, along with other physical changes such as cracking, telangiectasis (spider vessels), solar keratoses (gromths), ecchymosis (subcutaneous hemorraghic lesions) and loss of elasticity (sagging).
  • UV light is an electromagnetic radiation with a wavelength shorter than that of visible light, but longer than soft X-rays. It is so named because the spectrum consists of electromagnetic waves with frequencies higher than those that humans identify as the color violet (purple). UV light is typically found as part of the radiation received by the earth from the Sun.
  • the electromagnetic spectrum of ultraviolet light can be subdivided into:
  • UVA, UVB and UVC can all damage collagen fibers and thereby accelerate aging of the skin. Both UVA and UVB destroy vitamin A in skin, which may cause further damage. In the past UVA was considered less harmful, but today it is known, that it can contribute to skin cancer via the indirect DNA damage (free radicals and reactive oxygen species). UVB light can cause direct DNA damage. The mutations that are caused by the direct DNA damage carry a UV signature mutation. This cancer connection is one reason for concern about ozone depletion and the ozone hole.
  • Skin photoaged by UV radiation displays multiple histological features that reflect chronic skin inflammation and connective tissue damage.
  • the dermal damage induced by UV is principally manifested as destruction of the dermal extracellular matrix (ECM), which is composed primarily of type I collagen, elastin, proteoglycans and fibronectin.
  • ECM dermal extracellular matrix
  • MMP collagen-degrading matrix metalloproteinase
  • Sunscreen prevents the direct DNA damage which causes sunburn. Most of these products contain an SPF rating to show how well they block UVB rays. However, the toxicity of effective dose levels of synthetic sunscreens in terms of potential harm to the body is a matter of great concern. A recent study reports the possibility of endocrine disruption from using certain sunscreens.
  • a bioactive composition having natural UV photoprotective properties comprises an extract, active fraction or mixture thereof of a species from the ginger family (Zingiberaceae), wherein the extract, active fraction or mixture thereof is derived from Curcuma heyneana, Boesenbergia rotunda, Curcuma zedoria or mixture thereof.
  • the bioactive composition is able to inhibit UVB melanin formation, down-regulate MMP-1 expression and functions as UVB photoprotective viability agent.
  • the amount of the extract, active fraction or mixture thereof present in the composition ranges from 0.01 to 10% by weight composition.
  • the extract, active fraction or mixture thereof is derived from a rhizome, leaf, stem and/or bract of the species.
  • the extract is obtainable by extraction using a solvent from water, an anhydrous or hydrated lower alcohol containing 1 to 3 carbon atoms or a mixed solvent thereof.
  • the extract is also obtainable through hot water extraction, heat extraction, reflux cooling extraction, ultrasonic extraction and immersion extraction.
  • the active fraction is obtainable by preparative high performance liquid chromatography (HPLC).
  • HPLC preparative high performance liquid chromatography
  • the bioactive composition is suitable in delivery systems such as oil, cream, gel, spray, lotion and nano-lipid, nano encapsulation and liposome application.
  • the extract, active fraction or mixture thereof derived from the species Curcuma heyneana, Boesenbergia rotunda, Curcuma zedoria or mixture thereof are useful as natural UV photoprotective agents, particularly in the manufacture of a bioactive composition for topical application.
  • Fig 1 shows the preparative HPLC profiling for aqueous extracts (a) Curcuma heyneana, (b) Boesenbergia rotunda, and [ ] Curcuma zedoaria.
  • Fig 2 shows the effect of Boesenbergia rotunda, Curcuma zedoaria and Curcuma heyneana extracts on cell viability and inhibition of melanin formation induced by UVB in melanoma cell.
  • Fig 3 shows the UVB photo-protective effect of Boesenbergia rotunda, Curcuma zedoaria and Curcuma heyneana extracts on viability of fibroblast cell exposed to UVB irradiation
  • Fig 4 shows the effect of Boesenbergia rotunda, Curcuma zedoaria and Curcuma heyneana extracts on MMP-1 expression and cell viability in fibroblast cell. 5. Detailed Description of the Invention
  • the present invention provides a bioactive composition having natural UV photoprotective properties, which comprises an extract and/or active fraction derived from Curcuma heyneana, Boesenbergia rotunda, Curcuma zedoria or mixture thereof as the active ingredient.
  • the extract and/or active fraction is derived from a rhizome, leaf, stem and/or bract of the species.
  • These active ingredients exhibit melanin inhibition activity, are non-toxic and stable as skin photoprotective agents. They are also able to down-regulate MMP-1 expression in delaying skin photoaging process.
  • Three tests were carried out to examine the UV photoprotective effects of the extracts from Boesenbergia rotunda, Curcuma zedoaria and Curcuma heyneana.
  • Cytotoxicity test was carried out to examine the UVB photoprotective effect of the extracts on cell viability.
  • the result shows that Boesenbergia rotunda aqueous extract had the best viability value to the human dermal fibroblast (CCD114-sk) cells at 0.5 mg/mL with 63% cell survived compared to 0.5 mg/mL EGCG, a commercial agent used as positive control.
  • both 0.5 mg/mL and 1.0 mg/mL of Curcuma heyneana extract also showed no cytotoxicity to the cell.
  • MMP-1 Matrix Metalloproteinase-1
  • levels of MMP-1 protein expressed was measured.
  • MMP-1 production was reduced by 52.3% (Boesenbergia rotunda), 37.0 % [Curcuma zedoaria) and 34.32% [Curcuma heyneana) relative to untreated control. It was noted that these extracts at 0.1 mg/ml are not toxic to the cell with cell viability of more than 50% compared to control.
  • the amount of the extract, active fraction or mixture thereof present in the bioactive composition ranges from 0.01 to 10% by weight composition.
  • the active ingredient is contained in an amount of 0.50 (% w/w) based on total weight of the composition.
  • the bioactive composition comprising these extract may be used for cosmetic and pharmaceutical applications, particularly for the purpose of skin photo-protection.
  • the composition comprising natural plant material may be formulated into various forms for topical application such as emulsion, gel, cream, lotion, serum, toner, mask, water-in-oil, oil-in-water, microemulsion, nanoemulsion, pastes, sticks, cakes, pencils, essence, as well as other topical vehicles.
  • the present invention also can be incorporated into delivery systems such as liposomes, nano lipid carrier system and topical patches, tapes and sprays.
  • Boesenbergia rotunda (also known as Boesenbergia pandurata), Curcuma zedoaria and Curcuma heyneana were collected from Jerantut Pahang, Malaysia. The plants were authenticated by Kepong Herbarium, Forest Research Institute Malaysia (FRIM). The rhizomes were washed with tap water followed by distilled water and later air dried. It was further sliced using a mechanical slicer and dried in oven at 40°C for 24 hours. The dried sliced rhizome was powdered using a mechanical miller.
  • FRIM Kepong Herbarium, Forest Research Institute Malaysia
  • Aqueous extract were prepared by stirring the powdered rhizomes into a solution of water. The ratio of powdered rhizome to water was maintained at 1:20 (w/v). The extraction was performed at 40°C and left overnight under gentle agitation. The extract was later centrifuged, filtered and freeze dried. The freeze dried crude extracts were then used for further analysis. Coding for the aqueous extracts are as follows: Boesenbergia rotunda (BRA), Curcuma zedoaria (CZA) and Curcuma heyneana (CHA).
  • BRA Boesenbergia rotunda
  • CZA Curcuma zedoaria
  • CHA Curcuma heyneana
  • B16-F1 melanoma cells The B16-F1 (ATCC CRL-6323) melanoma cell line was purchased from American Type Culture Collection (ATCC).
  • the B16-F1 melanoma cells are melanin-producing cells which are generally used to verify the effects of whitening substances. Cells were first cultured in DMEM medium supplemented with antibiotics (lOOU/mL of penicillin and lOOU/mL of streptomycin) and 10% heat-inactivated fetal calf serum (Gibro-BRL) and maintained at 37°C in a humidified incubator containing 5% C0 2 . The B16-F1 cells were sub cultured when the cell confluence in 75cm 2 flask reached about 90%.
  • the B16-F1 melanoma cells were seeded into 24 well plate and cultured until they reached 90% confluence. They were then treated with sample at various concentrations for 24 hours using kojic acid as a standard.
  • a spectrum lamp which has a wavelength peak of 302 nm (UVLMS-38 EL Series 3UV lamp) was used as the UVB radiation source.
  • the UVB doses was measured based on duration of exposure. Briefly, after 24 hours of treatment, cells were rinsed with phosphate buffer saline (PBS) and lmL fresh PBS was added before exposing the cells to UVB dose (70 mj/cm 2 ). The maximum time for UVB irradiation was less than 2 min.
  • Table 1 Effect of Boesenbergia rotunda, Curcuma zedoaria and Curcuma heyneana on viability and inhibition of melanin formation induced by UVB in melanoma cell.
  • Human skin fibroblast CCD-1114SK (ATCC CRL 2450] cells, were obtained from the American Type Culture Collection. The cells were cultured in 10% fetal bovine serum in Dulbecco's minimum essential medium supplemented with lOOU/mL of penicillin and lOOU/mL of streptomycin at 37 °C in a humidify incubator containing 5% C0 2 . Cells were sub cultured when the confluence in 75cm 2 flask reached about 90%.
  • UVB radiation source A spectrum lamp (UVLMS-38 EL Series 3UV lamp) which has a wavelength peak of 302nm was used as the UVB radiation source.
  • UVB doses was measured based on duration of exposure. Briefly, after 24 hour treated, cells were rinsed with PBS and lmL fresh PBS was added before exposing the cells to UVB dose at (70 mj/cm 2 ]. The maximum time for UVB irradiation was less than 2 minutes.
  • Boesenbergia rotunda aqueous extract showed the best viability value to the human dermal fibroblast (CCD114-sk] cells at 0.5 mg/mL with 63 % cell survived compared to 0.5 mg/mL EGCG, commercial agent. However, both 0.5 mg/mL and 1.0 mg/mL of Curcuma heyneana aqueous extract also showed no cytotoxicity to the cell. Thus, 0.5 mg/mL of Boesenbergia rotunda aqueous extract is the best non toxic agent for UV photoprotection. Control refers to (untreated cell, UVB irradiate). (See Fig 3 and Table 2).
  • Table 2 UVB photoprotective viability of cells treated with Boesenbergia rotunda, Curcuma zedoaria and Curcuma heyneana in fibroblast cell.
  • MMP-1 Matrix Metalloproteinase-1
  • MMP-1 The production of MMP-1 was determined using an enzyme-linked immunosorbent assay (Sensolyte MMP-1 ELISA kit). This study only measured the level of MMP-1 production in fibroblasts because MMP-1 (interstitial collagenase) has been reported to have more involvement in damage to the skin collagen.
  • UVB radiation A spectrum lamp (UVLMS-38 EL Series 3UV lamp) which has a wavelength of 302 nm was used as the UVB radiation source.
  • UVB doses was measured based on duration of exposure. Briefly, after 24 hr treatment, cells were rinsed with phosphate buffer saline (PBS) and ImL fresh PBS was added before exposing the cells to UVB dose (70 mj/cm 2 ). Immediately after irradiation, fresh serum-free medium was added to the cells medium then incubated for 48 hr.
  • PBS phosphate buffer saline
  • MTT agent 5mg/mL MTT agent was added into each well and cells incubated for 3 hours at 37°C in a humidified incubator containing 5% CO2. Cells then centrifuged and dissolved with DMSO. Absorbance was measured using spectrophotometer at 590 or 630 nm.
  • Boesenbergia rotunda aqueous extract display the best activity in inhibiting MMP-1 protein expression with significant % of cell viability.
  • Epigalocatechingallate expressed as EGCG was used as commercial MMP-1 protein inhibitor agent in our study.
  • Control refers to (untreated cell, UVB irradiate). (See Fig 4 and Table 3).
  • Table 3 Effect of Boesenbergia rotunda, Curcuma zedoaria and Curcuma heyneana on MMP-1 expression and cell viability in fibroblast cell.
  • Boesenbergia rotunda (0.1 mg/ml) 47.7 100.4
  • Curcuma heyneana (0.1 mg/ml) 65.8 60.4 Preparation of UV blocker formulations containing Boesenbergia rotunda, Curcuma zedoaria and Curcuma heyneana as active ingredient.

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  • Health & Medical Sciences (AREA)
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Abstract

La présente invention concerne une composition bioactive comprenant un extrait, une fraction active ou un mélange de ceux-ci d'une espèce de la famille du gingembre (Zingiberaceae) destinée à être utilisée contre les effets nocifs du rayonnement ultraviolet (UV). La composition comprend un extrait et/ou une fraction active dérivé(e) de Curcuma heyneana, Boesenbergia rotunda, Curcuma zedoria ou d'un mélange de ceux-ci en tant que substance active. Les substances actives possèdent une activité d'inhibition de la mélanine, sont non toxiques et stables en tant qu'agents photoprotecteurs de la peau. Ils sont également capables de réguler à la baisse l'expression de MMP-1 en retardant le processus de photovieillissement de la peau.
PCT/MY2014/000271 2013-12-31 2014-12-30 Composition bioactive ayant des propriétés photoprotectrices naturelles contre les uv WO2015102478A1 (fr)

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MYPI2013702588 2013-12-31
MYPI2013702588A MY174568A (en) 2013-12-31 2013-12-31 A bioactive composition having natural uv photoprotective properties

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114191526A (zh) * 2021-12-10 2022-03-18 佛山市连艺生物科技有限公司 红火炬郁金精油在制备抗紫外光老化药物中的应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0920635A (ja) * 1995-07-04 1997-01-21 Shiseido Co Ltd 美白用皮膚外用剤
JPH0930945A (ja) * 1995-07-21 1997-02-04 Shiseido Co Ltd 皮膚外用剤
EP1133992A1 (fr) * 1999-09-23 2001-09-19 ASAC Compania de Biotecnologia E Investigacion, S.A. Nouvelles activites pharmacologiques des extraits de curcuma longa
US20100298444A1 (en) * 2007-12-21 2010-11-25 Asac Compania De Biotecnologia E Investigacion S.A. Method for improving the therapeutic efficacy of curcuminoids and their analogs

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0920635A (ja) * 1995-07-04 1997-01-21 Shiseido Co Ltd 美白用皮膚外用剤
JPH0930945A (ja) * 1995-07-21 1997-02-04 Shiseido Co Ltd 皮膚外用剤
EP1133992A1 (fr) * 1999-09-23 2001-09-19 ASAC Compania de Biotecnologia E Investigacion, S.A. Nouvelles activites pharmacologiques des extraits de curcuma longa
US20100298444A1 (en) * 2007-12-21 2010-11-25 Asac Compania De Biotecnologia E Investigacion S.A. Method for improving the therapeutic efficacy of curcuminoids and their analogs

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MUHAMMAD AGUNG B.H. SYAHPUTRO ET AL.: "Biological Activities of Panduratin A, an Active Compound from Temu Kunci (Boesenbergia rotunda", THE 6TH CONFERENCE OF INDONESIAN STUDENTS ASSOCIATION IN KOREA (CISAK 2013, vol. C4/P/38, 7 July 2013 (2013-07-07), pages 1 - 4 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114191526A (zh) * 2021-12-10 2022-03-18 佛山市连艺生物科技有限公司 红火炬郁金精油在制备抗紫外光老化药物中的应用

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