WO2011038472A1 - Extrait végétal normalisé, procédé de préparation d'extrait de plantes du genre sclerolobium, composition cosmétique, composition pharmaceutique et utilisation dudit extrait - Google Patents

Extrait végétal normalisé, procédé de préparation d'extrait de plantes du genre sclerolobium, composition cosmétique, composition pharmaceutique et utilisation dudit extrait Download PDF

Info

Publication number
WO2011038472A1
WO2011038472A1 PCT/BR2010/000321 BR2010000321W WO2011038472A1 WO 2011038472 A1 WO2011038472 A1 WO 2011038472A1 BR 2010000321 W BR2010000321 W BR 2010000321W WO 2011038472 A1 WO2011038472 A1 WO 2011038472A1
Authority
WO
WIPO (PCT)
Prior art keywords
extract
process according
sclerolobium
hexane
mixture
Prior art date
Application number
PCT/BR2010/000321
Other languages
English (en)
Portuguese (pt)
Other versions
WO2011038472A8 (fr
Inventor
ALberto José CAVALHEIRO
Dulce Helena Siqueira Silva
Vanderlan Da Silva Bolzani
Ian Castro-Gamboa
Adelson José De ARAÚJO
Rodrigo Fuscelli Pytel
Jean-Luc Gesztesi
Sandra Patrícia HURTADO MEDINA
Veléria Maria DI MAMBRO
Mary Sanae Nakamura
Original Assignee
Nature Cosméticos S.A.
Universidade Estadual Paulista "Julio De Mesquita Filho"
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.)
Filing date
Publication date
Application filed by Nature Cosméticos S.A., Universidade Estadual Paulista "Julio De Mesquita Filho" filed Critical Nature Cosméticos S.A.
Priority to BR112012009369A priority Critical patent/BR112012009369A2/pt
Publication of WO2011038472A1 publication Critical patent/WO2011038472A1/fr
Publication of WO2011038472A8 publication Critical patent/WO2011038472A8/fr

Links

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]
    • A61K8/9789—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
    • A61P17/18—Antioxidants, e.g. antiradicals
    • 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
    • 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 process for preparing extracts obtained from plants of the genus Scierolobium and the use of these extracts as antioxidants and for anti-aging activity in cosmetic and pharmaceutical compositions.
  • Skin is perhaps the organ of the human body most exposed to oxidative stress, including endogenous sources (enzymes, cells, pathological processes and diseases) and exogenous sources (pollutants, atmospheric gases, radiation and various chemicals) of reactive oxygen species (ROS). ), which include superoxide radicals, nitric oxide radicals and singlet oxygen. Oxidative injury to skin components such as lipids, DNA and proteins can significantly interfere with normal skin functions and induce pathological processes such as inflammation and cancer.
  • ROS reactive oxygen species
  • the most specific mechanisms of skin defense against oxidative stress include direct acting enzymes (SOD, catalase, peroxidases) and support enzymes (G6PD, xanthine oxidase) and indirectly acting low molecular weight antioxidant molecules (chelating agents) or direct action (free radical scavengers).
  • SOD direct acting enzymes
  • G6PD support enzymes
  • chelating agents chelating agents
  • free radical scavengers free radical scavengers
  • the latter include substances synthesized by cells (GSH, NADH, carnosine) and substances obtained from food sources (carotenes, tocopherols, polyphenols, ascorbic and lipoic acids, etc.).
  • Antioxidant agents can be supplied by food and are found in plant foods such as tomatoes, watermelon, beets, peppers, carrots, acerola, papaya, orange, lemon, melon, broccoli, strawberry, mango, kiwi, cabbage, pea, cashew, walnut, hazelnut, sweet potato, oatmeal, avocado, whole grains, pumpkin, cabbage, spinach, watercress, tea, rosemary, lemon, as well as animal origin such as meat, eggs, milk, fish, oysters, poultry and shellfish. They may also be provided by food supplementation.
  • antioxidants must also have photoprotective effects including reduced erythema, reduced sunburn cell formation, reduced DNA damage such as thymine dimers or oxidized nucleotides, reduction of UV immunosuppression, reduction of pigment anomalies, and eventually reduction of skin cancer and photoaging (Pinnell, et al. 2003).
  • antioxidant agents capable of removing ROS or inhibiting lipid peroxidation can be effectively used to protect or treat conditions related to oxygen free radical species and to prevent aging (or the symptoms of skin aging).
  • Antioxidant substances can also be obtained from plants not used for human consumption, as already documented in US 2003/0170332 and WO 2004/009575, being obtained from species of the Pinaceae family (US 2003/0170332) of the family Typhaceae ( WO 2004/009575).
  • the genus Scierolobium spp belonging to the family Leguminosae, subfamily Caesalpinioideae comprises the species S. aureum, S. denudapum and S. paniculatum which are arboreal.
  • the species S. aureum also known as stinks, field gonçalo and dung, has medium size, rough and peeling bark, pale, pubescent young branches; alternate leaves, composed of unipposed, with 5 to 9 opposite or subopposed leaflets, oval and oblong, obtuse to rounded base, acute to rounded apex, about 7 cm long and 3,5 cm wide, glabrous to pubescent. Its flowers are golden yellow, aromatic, arranged in broad terminal panicles.
  • S. paniculatum also known as white cab, charcoal and bird
  • S. paniculatum is a large tree, erect trunk, whitish bark, rough to streaked on young trees, cracked on older trees, young pubertal branches; alternate leaves, composed of unequipped, with 4 to 8 pairs of broad leaflets or with sparse fair hair on the underside, oblong, slightly rounded to obtuse base, acuminate apex, about 7 to 3 cm wide. It has small greenish-yellow flowers arranged in terminal panicles and a flat ellipsoid pod fruit (DURINGAN, et al. 2004).
  • S. aureum occurs in typical cerrado and cerrad ⁇ o areas.
  • S. paniculatum occurs in the Amazon, but is also well distributed throughout the Brazilian territory, in different soil types. This is a potential species for the recovery of degraded soils and enrichment of poultry (DIAS et al 1991). In plantations, it presents rapid growth, high litter production and ability to associate with potential N 2- fixing Rhizobium bacteria.
  • S. denudatum is an endemic tree of the Atlantic Forest, most often found in areas of dense but currently rare ombrophylous forest.
  • Squalene is used as an ingredient in cosmetic formulations for its photoprotective properties (HE et al 2002).
  • ⁇ -tocopherol (vitamin E) is one of the most important natural antioxidants, mainly due to its inhibitory effect on lipid peroxidation (KATSANDIS et al 1999).
  • Topical administration of lupeol at a dose of 1-2 mg / rat prevented the formation and growth of a 12-0-tetradecanoylforbol-13-acetate (TPA) -induced cancer model (SALEEM et al 2004).
  • TPA 12-0-tetradecanoylforbol-13-acetate
  • Lupeol inhibits copper salt-induced lipid peroxidation (ANDRIKOPOULOS et al 2003)
  • Lupeol also has anti-inflammatory activity by interfering with prostaglandin biosynthesis. inhibiting PGE2 synthesis (RAMIREZ-APAN et al 2004, REYES et al 2006).
  • Lupenone has significant inhibitory activity in herpes simplex virus HSV-1 and HSV-2 and also in African swine fever virus (ASFV) (MADUREIRA et al 2003).
  • Antifungal Sacharomyces cerevisae and Microsporum gypseum
  • bactericidal Esscherichia coli, Proteus vulgaris, Pseudomonas pyocyanea, Bacillus subtilis and Staphylococcus aureus
  • antioxidant activities of lupenone were reported (KIM et al 2001).
  • Flavonoids more specifically those containing catecholic units (o / fo-dihydroxyphenyls) in their chemical structure, such as quercetin derivatives and those containing pyrogallol units (1,2,3-trihydroxyphenyls), such as myricetin derivatives, may act as antioxidant micro-molecules both in the suppression of reactive oxygen species by inhibiting enzymes and chelating trace elements, both involved in the production of free radicals; as in the sequestration of reactive oxygen species and also in the induction and protection of antioxidant defenses (PIETTA 2000). More specifically, it has been shown that flanoids inhibit enzymes responsible for the production of superoxide anions, such as xanthine oxidase and protein C kinase.
  • Flavonoids also inhibit cyclooxygenases, lipoperoxidases, mitochondrial monooxygenases, glutathione S-transferase, mitochondrial succinyloxidase and NADH oxygenase, all involved in the formation of reactive oxygen species (URSINI et al 1994, BROWN et al 1998). Flavonoids efficiently chelate trace metals, such as iron and copper, which play an important role in the formation of reactive oxygen species, and the presence of catechol, pyrogallol and 4-oxo groups together with 5-hydroxy are critical for efficiency. this chelation.
  • flavonoids are thermodynamically capable of reducing highly oxidized free radicals, with redox potential between 2.13 - 1.0 V, such as superoxide, peroxyl, alkoxy and hydroxyl radicals by donating radical hydrogen (BUETTENER 1993; ROBAK, & GRYGLEWISKI 1988; HUSSAIN et al 1987; TOREL et al 1986).
  • Patent literature mentions the use of Scierolobium spp in 2 documents, WO 00/03749 and WO 00/03748. In both, this genus is suggested as a source of triterpenes used in hair growth regulation processes.
  • the present invention relates to a process for preparing a plant extract of the genus Scierolobium comprising the steps of subjecting Scierolobium plant leaves to hexane extraction to obtain an extract containing lipophilic components.
  • the present invention relates to a process for preparing a plant extract of the genus Scierolobium comprising the steps of:
  • the present invention relates to a process for preparing a plant extract of the genus Scolobobium comprising the steps of:
  • plant tissue includes, but is not limited to, leaves of the species of Scierolobium spp.
  • Figure 1 shows schematic diagrams demonstrating the procedures used to obtain antioxidant substances and lipophilic antioxidant fractions (FAL) from organic and hydrophilic extract (FAH) from hydroalcoholic extract, from leaves of species of Scierolobium spp.
  • FAL lipophilic antioxidant fractions
  • FAH organic and hydrophilic extract
  • PE-DVB polystyrene divinylbenzene.
  • Figure 2 shows the antioxidant substances present in the antioxidant extracts and fractions (FAH and FAL) of Scierolobium paniculatum, Scierolobium aureum and Scierolobium denudatum: ⁇ -tocopherol (1), squalene (2), lupeol (3), lupenone (4), mycetin-3-O-galactopyranoside (5), mycetin-3-O-ramnopyranoside (6), quercetin-3-O-galactopyranoside (7), keretin-3-O-arabinopyranoside (8), quercetin- 3-O-Rhamnopyranoside (9), Mycetin-3-0- (3 "-galloyl-Ramnopyranoside) (10), Mycetin-3-0- (2" -galoyl-Ramnopyranoside) (11).
  • Figure 3 shows the chromatograms obtained in reverse-phase high performance liquid chromatography of Scierolobium aureum (A), Scierolobium denudatum (B), Scierolobium panicu- latum (C) and antioxidant agents (D) used as standard: ⁇ -tocopherol (11.01 min), lupenone (11.96 min) ⁇ -tocopherol (12.75 min) and squalene (20.19 min).
  • Figure 4 shows the chromatograms obtained in reverse phase high performance liquid chromatography of the hydroalcoholic extracts of Sclerolobium aureum (A), Sclerolobium paniculatum (B), Sclerolobium denudatum (C) and the standards used: miricetin (13, 06 min), quercetin-3-O-arabinopyranoside (17.03 min), 2 '-0-galloyl-pyrnopyranoside quercetin (22.38 min) (D).
  • Figure 5 shows the sequestering activities of the radical DP-
  • Figure 6 shows the sequestering activities of the DP-PH radical shown by the hydroalcoholic extracts of Sclerolobium denudatum (W: water; EtOH: ethanol).
  • Figure 7 shows the DP-PH sequestering activities presented by the hydroalcoholic extracts of Sclerolobium paniculatum (W: water; EtOH: ethanol).
  • Figure 8 shows the DPPH radical scavenging activity by the glycosylated flavonoids, which correspond to the numbers 5 to 11 in Figure 2.
  • Figure 9 shows the evaluation of lipid peroxidation protection during 1 and 2 hours of liposomes treated with extract samples obtained from S. aureum leaves.
  • the 50% hydroalcoholic extract (SaHA), the organic extract (SaH) and the lipophilic antioxidant fraction (SaFAL) were administered to the liposomes in concentrations ranging from 40 to 400 pg / ml.
  • Figure 10 shows the 1 and 2 hour evaluation of lipid peroxidation protection of liposomes treated with mixtures of hydrophilic and lipophilic antioxidant agents obtained from S. aureum leaf extracts: 50% hydroalcoholic extract (SaHA) and organic extract. (SaH) 60:40 (m / m), and the mixture containing the 50% hydroalcoholic extract (SaHA) and the lipophilic antioxidant fraction (SaFAL) 50:50 (w / w). Both mixtures were administered at a concentration of 40 pg / ml.
  • Figure 11 shows the yield, relative to the dry leaf mass used, of obtaining all glycosylated flavonoids from the hydroalcoholic extracts of three species of Scierolobium spp.
  • Figure 12 shows the yield of glycosylated derivatives of the miricetin and quercetin flavonoids in the leaf extracts of the three species of Scierolobium. Result expressed in milligrams of flavonoid per gram of dried leaves.
  • Figure 13 shows the illustrative photos of the fractions and image of the silica gel CCDC plate of fractions F1, F2 and F3 of the organic extract after solid phase extraction using active charcoal.
  • Figure 14 shows the chromatograms of fractions F1, F2 and F3 obtained from dried leaf extracts of Scierolobium aureum obtained by high performance liquid chromatography (HPLC-UV). Chromatograms were obtained at 200 nm using column C18 eluted with acetonitrile at 2.0 ml min "1. Each sample was injected in a volume of 10 ⁇ volume.
  • Figure 15 shows the chromatograms of XAD-A fractions in water (A), XAD-B in water / ethanol 1: 1 (B), XAD-C in ethanol (C) and XAD-D in ethyl acetate (D).
  • hydroalcoholic extract obtained by high performance liquid chromatography (HPLC-UV). Chromatograms were obtained at 254 nm using column C18, eluting with 16 to 21% acetonitrile in 13 " , 21% to 35% acetonitrile in 25min, 35% acetonitrile to 30min with a flow rate of 1.5ml min " 1 . Each sample was injected in a volume of 20 ⁇ .
  • the present invention combines polar and non-polar extracts and fractions, combining antioxidants and hydrophilic and lipophilic chemoprotectors, in order to obtain additive effects in the protection against lipid peroxidation. Furthermore, the present invention proposes procedures for obtaining the FAH and FAL antioxidant fractions without pigments, enabling the preparation of more attractive cosmetic formulations.
  • the present invention proposes the standardization of leaf extracts of Scierolobium spp, aiming to exploit them as source materials of natural antioxidants, applicable in cosmetic formulations.
  • Wood of Scierolobium species is already used in charcoal and the feasibility of this invention using the leaves of species of this genus, now totally discarded, will provide added value to the cultivation of Scierolobium spp, stimulating family farming and the recovery of tree density in degraded areas.
  • the stirring step (b) is performed by sonication and the liquid and solid phase separation step is performed by centrifugation.
  • the process of the present invention includes the following steps:
  • plant tissues are, but are not limited to,
  • Scierolobium aureum Scierolobium paniculatum, Scierolobium denudatum and mixture thereof.
  • the highest levels of actives have been detected in the leaves but can also be used as stem, root, fruit, flowers and mixtures.
  • organic solvent described in item c) ee) are organic support solvents such as ethers, dichloromethane, chloroform, ethyl acetate, preferably hexane.
  • the plant extract can be lightened by lightening resin which is selected from the group comprising vegetable resin pigment extraction as celite® and derivatives thereof, active charcoal, divergan F ®, polyvinyl acetate, ethyl cellulose, polymethyl methacrylate, methacrylethyl betaine / methacrylate copolymer, methacrylic acid copolymers, aminoalkyl methacrylate copolymers, phthalate cellulose acetate, poly-N-vinyl-2-caprolactam, poly-N-vinyl-3-methyl-vinyl 2-caprolacam, poly-N-vinyl-3-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-caprolactam, poly-N- vinyl-3-ethyl-2-pyrrolidone, poly-N-vinyl-4,5-dimethyl-2-pyrrolidone and a mixture thereof.
  • lightening resin which is selected
  • Obtaining hydroalcoholic extracts of species of the genus Sclerolobium include the following steps:
  • hydroalcoholic solution includes, but is not limited to, the 1: 1 (v: v) ethane-water solution.
  • Methanol, propanol or isopropanol may also be used, preferably ethanol.
  • the plant extract may be bleached through bleaching resins which is chosen from the group comprising plant pigment extraction resins as ion exchange resins as polystyrene divinylbenzene mixed polymer resins (XAD-4 ® ), active charcoal , divergan F (PVP), polyvinyl acetate, ethyl cellulose, polymethyl methacrylate, methacrylethyl betaine / methacrylate copolymer, methacrylic acid copolymers such as Eudragit L 100 ® , Eudragit L 125 ® , Eudragit L 100-55 ® , Eudragit L 30D -55 ® , aminoalkyl methacrylate copolymers, phthalate cellulose acetate, and a mixture thereof, poly-N-vinyl piperidone, poly-N-vinyl-2-caprolactam, poly-N-vinyl-3-methyl-2-caprolacam, poly-N- vinyl-3-methyl-2-piperidone, poly-N
  • tissues of Scierolobium species more specifically leaves, when subjected to successive extractions with organic solvents such as hexane and hydro-alcoholic mixtures, particularly ethanol / water, provide extracts and fractions. with antioxidant properties.
  • the genus Scierolobium belongs to the family Leguminosae, subfamily Caesalpinioideae.
  • the species S. aureum, S. denudatum and S. paniculatum are arboreal, and S. aureum, also known as fede-stink, field gonçalo or dung, has medium size, rough and peeling bark.
  • pubescent young branches artern leaves, unipposed compound, 5 to 9 opposites or subopposed leaflets, oval and oblong, obtuse to rounded base, acute to rounded apex, about 7 cm long and 3,5 cm wide, glabrous to pubescent; aromatic yellow-gold flowers arranged in broad terminal panicles; fruit oblong pod, flattened, indiscent. It occurs in areas of typical cerrado and cerrad ⁇ o.
  • S. paniculatum known as the white cab, charcoal or passerine, is a large tree, erect trunk, whitish bark, rough to streaked in young trees and cracked in older trees, weeds young pubertules; alternate leaves, composed of unkempt, 4 to 8 pairs of thin or sparse clear hairs on the underside, oblong, rounded to obtuse base, slightly uneven, acuminate apex, about 7 cm to 3 cm wide; small greenish-yellow flowers arranged in terminal panicles; ellipsoid flat pod fruit (Duringan, G. et al., Cerrado Paulista Plants, Pages & Letters Publishing and Printing, S ⁇ o Paulo, 2004).
  • Lipophilic antioxidants include squalene, ⁇ -tocopherol, lupeol and lupenone represented by the following formulas:
  • Hydrophilic antioxidants include glycosylated flavonoids such as:
  • the extract comprising the lipophilic and hydrophilic fractions, which has antioxidant properties, is useful for use in cosmetic or pharmaceutical compositions.
  • fabrics of Sclerolobium species are shade-dried or preferably oven-circulating at about 40 ° C and ground. Thereafter this dried and ground vegetable material is subjected to successive extractions with organic solvents, namely hexane and subsequently with hydro-alcoholic mixtures, preferably 1: 1 (v / v) ethanol / water mixtures.
  • the fraction enriched in lipophilic antioxidants (FAL) and without interfering pigments, more specifically chlorophylls, is prepared by treating the hexane extract with at least one adsorbent substrate of natural origin, preferably using an equal extract / substrate ratio. at 1: 4 (w / w).
  • the hexane-eluted fraction contains squalene (1), ⁇ -tocopherol (2), lupenone (3) and lupeol (4).
  • Lipophilic extract (hexane extract) and FAL preferably contain antioxidant substances represented by formulas 1 to 4, with contents ranging from 0.001 - 1% and 0.01 - 10%, respectively. The range of content of antioxidant substances is due to seasonal variations and interspecies variations.
  • the hydrophilic antioxidant (FAH) enriched fraction is prepared by treating the hydroalcoholic extract, more specifically the 1: 1 (v / v) ethanol / water extract, with at least one mixed adsorption polymer resin, initially eluted with water. for the elimination of and other polar substances, and then with ethanol / water mixtures, preferably with 60:40 (v / v) ethanol / water solution.
  • the hydroalcoholic extract and FAH preferably contain antioxidant substances represented by formulas 5 to 11, with contents between 0.001 - 1% and 0.01 - 15%, respectively.
  • the range of content of antioxidant substances is due to seasonal variations and interspecies variations.
  • the substances obtained according to the invention and represented by the chemical formulas 1-11 above have antioxidant activities such as 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity.
  • Figures 1 to 4 show graphs showing free radical scavenging results of various fractions obtained in accordance with the present invention.
  • Hexane extract and hydroalcoholic extract were analyzed by solid phase extraction process eluting the Hex - AcOEt - MeOH gradient sample over normal phase adsorbent and reverse phase liquid chromatography respectively, where the compounds illustrated in figures 1 to 11 were verified. and mentioned in the flow chart found in example 1 below. These compounds remain, that is, they are verified in the lipophilic and hydrophilic antioxidant fractions (FAL and FAH).
  • FAL and FAH may be added alone, combined in varying proportions or combined with other anti-radical substances for the preparation of cosmetic and pharmaceutical formulations in which they will act as antioxidant systems.
  • Example 2 Obtaining and Quantifying Hexan Extracts leaves of S. aureum, S. denudatum and S. paniculatum.
  • Hexane Extract 500 mg of shade-dried and ground leaves were extracted with 5 ml of hexane by sonification (30 min). After centrifugation (10 min, 1200 rpm) the supernatant (hexane extract) was removed. This procedure was repeated 5 times, providing the hexane extracts 1, 2, 3, 4 and 5, which after taking aliquots for weighing and CLA-E analysis, were pooled. In these extracts were quantified ⁇ -tocopherol, ⁇ -tocopherol, squalene and lupenone.
  • the hexane extract of S. aureum was submitted to solid phase extraction using three distinct stationary phases, activated charcoal, celite ® and divergan.
  • the objective of the extractions was to obtain a fraction rich in antioxidant components and with little or no pigment.
  • a glass column containing 5.0g of active charcoal was used.
  • a mixture containing 9.0g of sample and 40g of active carbon was suspended in hexane and applied to the column.
  • the sample was eluted with: 300ml hexane (F1), 250ml hexane / AcOEt (9: 1) (F2), and 750ml AcOEt (F3).
  • F1 300ml hexane
  • F2 250ml hexane / AcOEt (9: 1)
  • F3 750ml AcOEt
  • the addition of 40g of active charcoal to 9g of extract sample is indispensable for the whitening of the extract.
  • Other auxiliary solvent options may also be used as mixtures of hexane with chloroform, dichloromethane, acetone, isopropanol, ethers, preferably the hexane / AcOEt mixture is used.
  • the flavonoid contents in the extracts showed significant differences among the three studied plants, however, the best extraction yield for the three species, in terms of flavonoid milligram. per gram of dry leaf was obtained when using a 1: 1 EtOH / Water mixture.
  • the proportion of glycosylated quercetin and mycetin flavonoids remains practically unchanged, so that the solvent system with the highest total flavonoid yield is also the best yield for the glycosylated quercetin and myricetin.
  • Hydroalcoholic Extract Plant material already extracted with hexane was extracted with 5 ml 1: 1 (v / v) MeOH / water by sonication (30 min). After centrifugation (10 min, 1200 rpm) the supernatant (hydroalcoholic extract) was removed. This procedure was repeated 5 times, providing the hydroalcoholic extracts 1, 2, 3, 4 and 5, which, after weighing and HPLC analysis, were pooled. In these extracts the glycosylated flavonoids were quantified.
  • the hydroalcoholic extract of S. aureum was submitted to solid phase extraction using three distinct stationary phases, active carbon, XAD-4 and divergan F.
  • the objective of the extractions was to obtain a fraction rich in antioxidant components and with little or no pigment. .
  • Hexane Extracts A 1ml aliquot of each of the hexane extracts of Scierolobium aureum, Scierolobium paniculatum and Scierolobium denudatum was filtered and analyzed by HPLC-DAD under the following chromatographic conditions:
  • UV-VIS UV-VIS, 200 and 290 nm.
  • Hydroalcoholic extracts An aliquot of each of the ethanolic extracts of Scierolobium aureum, Scierolobium paniculatum and Scierolobium denudatum was filtered and analyzed by HPLC-DAD under the following chromatographic conditions:
  • Figures 3 and 4 illustrate the chromatograms obtained for the hexane and hydroalcoholic extracts of leaves of Sclerolobium spp., Respectively.
  • the hexane extracts greater similarity between those obtained from leaves of S. aureum and S. paniculatum, whereas the hexanic extract of S. denudatum reveals a more complex profile, but with less intense peaks.
  • the polar extracts of S. denudatum and S. paniculatum are easily distinguishable from the polar extract of S. aureum leaves by the absence of representative peaks of myriacetrine galls (compounds 10 and 11, Figure 2).
  • Table 4 Yield of obtaining hydroalcoholic extracts from dried leaves of 3 species of the genus Sclerolobium spp: Sclerolobium aureum, Sclerolobium paniculatum and Sclerolobium debu- datum.
  • Mycetin-2 "-galoyl 0.03 - 5.0 4.5 ng 14 ng
  • the yields obtained for hexanic extract were similar for the three species of Sclerolobium, that is, of the order of 50mg of extract per gram of dry leaf.
  • the yields obtained for the hydroalcoholic extract were significantly higher for S. paniculatum (483.4 mg / g) and S. aureum (365.4 mg / g) leaves, compared to the yield obtained for S. paniculatum leaves. denudatum (242.0 mg / g).
  • Higher contents of glycosylated flavonoids were also obtained from S. aureum (96.5 mg / g) and S. paniculatum (90.7 mg / g) leaves (Table 8).
  • S. aureum hydroalcoholic extract contains 26.4% glycosylated flavonoids
  • S. paniculatum hydroalcoholic extract contains 18.8% glycosylated flavonoids.
  • glycosylated flavonoids linked to a gallic acid unit (myricetin 3-0- (2 "-O-gallon) -a-raminopyranoside and myricetin 3-0- (3" -O-gallonyl) -a-ramine - pyranoside) in the hydroalcoholic extract of S. aureum gives it a higher potential use as antioxidant compared to other extracts tested, since when tested with DPPH, these flavonoids showed higher antioxidant activity than those with only the glycosidic unit.
  • FM2 MeOH / Water fraction (90:10) was submitted to preparative HPLC, and FM-P1 (7mg) and FM-P2 (24mg) and FM-P3 (3mg), FM-P4 ( 25mg), FM-P61 (13mg), FM-P53 (5mg) and FMP62 (17mg).
  • the type of stationary phase used varied according to the polarity of the samples to be analyzed, preferably using silica gel Si-60, 80-230 mesh particles or amberlite XAD-16.
  • the elution was done in gradient mode, with hexane / AcOEt and then AcOEt / methanol mixtures, in increasing order of polarity.
  • the elution was also done in gradient mode, but with mixtures of water and methanol in decreasing order of polarity.
  • a Varian preparative chromatograph consisting of two Dynamax model SD-1 pumps and a ProStar 320 UV-Visible detector was used.
  • the column used was a C18 Phenomenex with dimensions of 21.20mm x 250mm and particles of 12 ⁇ .
  • NMR spectra were obtained on a Varian inova 500 spectrometer, operating at 500MHz and 125MHz at 1 H and 13 C, respectively.
  • the standard used as reference was TMS and the solvent used was Merck branded CDCI 3 and DMSO-c 6. Chemical shifts were expressed in units ⁇ and coupling constants (J) in Hz.
  • Substance 1 identified as ⁇ -tocopherol, is one of the constituents of vitamin E.
  • the singlet at ⁇ 1, 15 was assigned to the methyl group hydrogens at position 2 and the ⁇ 2.03 singlet to the hydrogen from the methyl groups found at positions 5, 7, and 8.
  • the signals for the group hydrogens C-4 ', C-8' and C-12 'methyl appear as doublets at ⁇ 0.80.
  • Hydrogens H-1 'to H-12' appear as multiplets between ⁇ 1.01 and 1.50.
  • the 13 C NMR spectrum shows signals corresponding to twenty-nine carbon atoms (Table 8).
  • six signals were found for quaternary aromatic carbons at ⁇ 117.3, 118..4, 121.0, 122.6, 145, 5 and 145.6, which were attributed to carbons C-4a, C-5, C-7, C-8, C-6 and C-8a, respectively.
  • the ⁇ 74.5 signal was assigned to C-2, an sp 3 carbon attached to an oxygen atom.
  • Signals were also observed for four methyl carbons between ⁇ 19.6 and 22.7, which were attributed to the methyl groups at C-4 ', C-8' and C-12 ', respectively.
  • the signals related to the methyl linked to the aromatic carbons C-5, C-7 and C-8 appear between ⁇ 11, 2 and 12,2, while the signal referring to the methyl carbon on C-2 appears at ⁇ 23,8.
  • the twelve signals for C-1 'to C-12' side chain carbons have a chemical shift between ⁇ 24.7 and 40.0. Identification was confirmed by comparing the data found with those found in the literature (YEN, 1996).
  • Substance 2 identified as squalene, is an open-chain triterpene with six unsaturation.
  • the 1 H NMR spectrum (Table 9) shows signals of sp2 carbon-linked hydrogen at ⁇ 5.1 and signals from methyl group hydrogens at ⁇ 1, 61 and ⁇ 1, 69. Hydrogens from methylene groups appear in ⁇ 2,1.
  • the 13 C NMR spectrum shows signals for twelve sp 2 carbons in the region of ⁇ 124, ⁇ 131 and ⁇ 134.
  • the signals for eight methyls appear at ⁇ 15.98, ⁇ 16.03, ⁇ 17.6, ⁇ 25.6 and ⁇ 25.7.
  • the methylene groups have displacement between ⁇ 26.80 and ⁇ 39.76 (Table 9). Identification was confirmed by comparing the data found with those found in the literature (HE, 2002).
  • Substance 3 has been identified as ⁇ -lupeol.
  • the signals related to the hydrogens of the other groups CH and CH 2 are between ⁇ 0.9 and 2.4.
  • the 13 C NMR spectrum showed a characteristic carbinolic signal at ⁇ 76.7.
  • seven signals regarding ⁇ 28.2 methyl groups can also be observed; 22.0; 15.9; 16.1; 14.6; 18,0 and 19,3 and the carbon signal of the terminal methylene group at ⁇ 109,2.
  • Substance 4 identified as Lup-20 (29) -en-3-one (lupene), is a lupane-like triterpene.
  • the doublet at ⁇ 1, 6 and the singlets at ⁇ 0.95, ⁇ 0.86, ⁇ 0.88 and ⁇ 0.72 were attributed to the hydrogens of the methyl groups H-30, H-23, H-25, H -27 and H-28, respectively.
  • the singlet at ⁇ 0.99 was attributed to the hydrogens of the methyl groups H-24 and H-26.
  • the signals related to the hydrogens of the other groups CH and CH2, are between ⁇ 0.9 and ⁇ 2.4.
  • the 13 C NMR spectrum showed a characteristic ketone carbonyl signal at ⁇ 218.07, attributed to C-3 carbon.
  • the seven signals of the methyl groups in ⁇ 21, 03, ⁇ 26,6, ⁇ 15,8, ⁇ 15,9, ⁇ 14,4, ⁇ 18,0 and ⁇ 19 can also be determined. 3 assigned to carbons C-23 to C-28 and C-30, respectively, and the carbon-related signal of the terminal methylene group C-29 at ⁇ 109.2. It is also possible to observe the ten signals referring to the other carbons of the methylene groups between ⁇ 19.6 and ⁇ 40.0 and the signals referring to the methic carbons at ⁇ 54.97, ⁇ 49.82, ⁇ 38.21, ⁇ 48.28 and ⁇ 47.96 for C-5, C-9, C-13, C-18 and C-19 (Table 11). Identification was confirmed by comparing the data those found with those found in the literature (KIM, 2001; MAHATO, 1994).
  • the substance P1 identified as myricetin-3- ⁇ - ⁇ -galactopyranoside (5), shows in the 1 H NMR spectrum (Table 12) signals in the region of typical flavonoid aromatic hydrogens.
  • the singlet in the region of ⁇ 12.6 (1 H) was assigned to C-5 hydroxyl hydrogen.
  • the doublets at ⁇ 6.17 (1 H) and ⁇ 6.35 (1 H), with coupling constants of 2.0 Hz, were assigned to ring H-6 and H-8.
  • the singlet in ⁇ 7.20 (2H) was attributed to ring 2 'and 6' hydrogens.
  • the observed signs (Table 11) are typical of aglycone mycetin, as reported in the literature (MARKHAM, 1978).
  • Substance P2 identified as myricetin-3- ⁇ - ⁇ - rhamnopyranoside (6), shows in the 1 H NMR spectrum (Table 13) signals related to the aglycone portion, with displacements and multiplicities similar to those presented by substance 5, suggesting to have the same aglycone, myricetin.
  • the region of the spectrum related to the glycosidic unit had a broad singlet ⁇ 5.20, which was attributed to the sugar-like anomeric hydrogen H-1 "typical of the glycosidic bond.
  • the doublet observed at 5.89 (J 6 , 5Hz), referring to H-6 "methyl is characteristic of rhamnose.
  • the signal in the region of ⁇ 133,4 (C-3), with diamagnetic displacement, as well as the signals in ⁇ 156,1 (C-2), ⁇ 177,4 (C-4) and ⁇ 161,2 ( C-5) with paramagnetic displacements relative to quercetin are typical of the presence of a glycosidic moiety in the C-3- ⁇ of ring C (AGRAWAL, 1989).
  • the presence of oxygenated aromatic carbons was confirmed by the signals at ⁇ 161, 2 (C-5), ⁇ 144.8 (C-3 ') and ⁇ 148.4 (C-4') in the 13 C NMR spectrum.
  • Substance P4 has been identified as quercetin-3- ⁇ - ⁇ -arabinopyranoside (8).
  • Substance P6.1 has been identified as quercetin-3- ⁇ - ⁇ -ramnopyranoside (9).
  • the 1 H NMR spectrum had a doublet at ⁇ 5.26, with a coupling constant of 1.0 Hz, which was attributed to the anomeric sugar H- "hydrogen, typical of glycosidic bonding.
  • Substance P6.2 was identified as myricetin-3-0- (2 "-0-gallonyl) - ⁇ -ramnopyranoside (11).
  • the signals observed in the 1 H NMR spectrum for the aglycone portion showed similar offsets and multiplicities. those presented by substance P2 (Table 17), suggesting that it is the same aglycone, myricetin.
  • the doublet observed at 5.83 (J 5.5 Hz) for methyl H-6 "is characteristic of rhamnose.
  • the 13 C-NMR spectrum had a 5 98.3-shift signal assigned to the C-1 "anomeric carbon and a .517.6 signal typical of R-6" methyl carbon from rhamnose. .
  • the other signs were attributed by comparing data from the literature and observing the correlations in the gHMQC and gHMBC experiment.
  • Substance P5.3 has been identified as myricetin 3-0- (3'-O-galloyl) - ⁇ -rhamnopyranoside (10).
  • the signals observed in the 1 H NMR spectrum (Table 18) for aglycone and for golic acid ester were similar to those observed in P62, with only a difference in the chemical displacements for the glycosidic unit found.
  • the doublet observed at 50.83 (J 5.5 Hz) for methyl H-6 "is characteristic of rhamnose.
  • Figure 2 shows the structures of all substances isolated and / or identified from the phytochemical studies on leaves of Sclerolobium.
  • A. DPPH The samples of plant extracts and pure substances are solubilized in MeOH, obtaining solutions of known concentrations. which are diluted in 96-well plates to obtain seven solutions of different concentrations. An aliquot of 100 ⁇ volume of each solution (triplicate) is transferred to the reading plate, then 200 ⁇ of DPPH solution (40 pg ml "1 ) is added, the plate is immediately protected from light, wait for 30 minutes and read.
  • the hydroalcoholic extracts obtained by extracting leaves of Sclerolobium spp with water, ethanol or a mixture of these, and the antioxidant substances represented by formulas 5 to 11 (Figure 2) have antioxidant properties, as shown by the results of the sequestering capacity. of the DPPH radical ( Figures 5 to 8). These results also indicate greater antioxidant potential for extracts obtained from S. aureum compared to leaves obtained from the other two species. It is also evident the greater antioxidant potential (free radical scavenger) of mycetrine 10 and 11 galls ( Figure 8), which may be explained by the presence of two trihydroxyphenyl groups in each of these substances.
  • hydroalcoholic extracts of S. aureum for presenting better results in DPPH tests, were submitted to tests to evaluate the membrane protective activity in lipid peroxidation tests.
  • Lipoperoxidation analysis used egg fostadylcholine liposomes as lipid source and iron / ascorbic acid as lipoperoxidation initiator. The samples were incubated at 37 ° C and after predetermined times, samples were taken to react with thiobarbituric acid in acid medium and elevated temperature. This reaction forms the malondialdehyde complex (MDA) and thiobarbituric acid, which was measured at 535nm. MDA is a byproduct of the lipid peroxidation reaction and therefore an indirect measure of it.
  • MDA malondialdehyde complex
  • Apolar extract obtained by extracting leaves of Sclerolobium aureum with hexane, and fractions obtained by fractionation Solid phase extraction using as adsorbent active charcoal, more specifically the FAL fraction have antioxidant properties, as shown by the results obtained in lipid peroxidation assays. ( Figure 9).
  • Hexane and hydroalcoholic extracts, as well as FAL and FAH fractions may be combined in any proportion for the preparation of cosmetic formulations.
  • the Ames Test was conducted with the SPMH fraction using the TA97a, TA98, TA 100, TA 102 and TA 1535 strains. The test was performed with and without metabolic activation. The sample was tested at five concentrations 0.001; 0.01; 0.1; 1.0 and 5.0 mg / plate. Ames test, performed on prokaryotic Salmonella typhimurium cells with and without metabolic activation, conducted with polar extracts (EHA) of leaves of Sclerolobium species, at concentrations of 0.001 to 5.0 mg / plate, indicated absence of mutagenic potential in these samples.
  • EHA polar extracts
  • Solubility analysis and concentration definition tested Solubility of samples is assessed according to internationally standardized assays by the US National Institute of Health (NIH-USA). For better solubilization of samples in aqueous solutions such as DEMEN (in the cytotoxicity assay) or PBS (in the phototoxicity assay) a maximum concentration of 1% DMSO or ethanol is allowed. Thus, masses of plant extracts ranging from 10 to 30 mg were dissolved in 10 ml of solution containing 1% DMSO or ethanol in DMEM (for cytotoxicity), and 1% DMSO or ethanol in PBS (for phototoxicity) according to the best. solubility of each visually evaluated extract.
  • DEMEN in the cytotoxicity assay
  • PBS in the phototoxicity assay
  • the concentrations employed in cytotoxicity and phototoxicity tests range from 0.003 to 3 mg / ml.
  • Cytotoxicity 3T3 cells are plated in sterile 96-well plates at a density of 1x10 4 cell / well. After 24 hours the cells are incubated for 24 hours with the samples diluted in 5% SFB culture medium. Subsequently, they are incubated with Neutral Red for 3 hours. Excess dye is washed with PBS and the chromed crystals are dissolved with ethanol / acetic acid / water (50: 1: 49). The reading is taken at 540 nm and the results are used to calculate the concentration at which 50% of the cells are viable (IC 50 ). Thus the higher the IC 50 value, the lower the cytotoxic potential of the sample and vice versa.
  • 3T3 cells were plated in sterile 96-well plates at a density of 1x10 4 cell / well. Two identical plates are prepared: one of them was irradiated with UVA and the other will be kept in the dark as a control. After hours of plating, the cells were incubated for 1 hour in the dark with diluted PBS samples, after which one was irradiated with 5 Joules / cm 2 UVA light for 50 minutes. The plates were washed with PBS and given culture medium.
  • the cosmetic or pharmaceutical composition object of the present invention comprises: (i) from 0.00001% to 40.0% by weight of Scierolobium spp extract obtained by the extraction process object of the present invention; and
  • this composition comprises 0.001 to 8.0% by weight, more preferably from 0.01% to 2.00% by weight of an extract of S. aureum, S. denudatum and S. paniculatum, preferably. said extracts containing ⁇ -tocopherol, ⁇ -tocopherol, squalene and lupenone.
  • dosage forms of products which may be prepared from the Scierolobium spp extract object of this invention or from active release systems comprising such extract are:
  • the physiologically acceptable carrier it consists of a usual cosmetic or pharmaceutical base according to the intended application for the composition to be prepared.
  • This carrier is comprised of usual physiologically inert compounds and adjuvants.
  • Water is the basis of several preferred embodiments of the cosmetic composition of the present invention, acting as the vehicle for the other components.
  • the compositions of the present invention comprise preferably demineralized or distilled water at a suitable percentage (q s.p.) to achieve 100% of the formula based on the total weight of the present composition.
  • q s.p. suitable percentage
  • other cosmetically acceptable vehicles may be used in the present invention.
  • Antioxidant agents BHT, tocopherol and / or its derivatives, catechins, tannins and / or their derivatives, phenolic compounds, hydroquinone, among others;
  • Film forming agents agar gum, carrageenan gum, alginates, arabic gum, gelatin;
  • microcrystalline mesh forming agents dextrans, methyl acrylates, PHB, PHA;
  • Polymeric agents and / or copolymer agents silicone copolymers, siloxane and / or modified silicone polymers, acrylate copolymers;
  • Consistency agents vegetable waxes, mineral hydrocarbons, paraffin wax, beeswax, white wax, whale sperm, cocoa butter, shea butter, sugar cane wax;
  • Emollients liquid paraffin, palm oil, cupuacu butter, lecithin, milk amino acids, wheat protein, vegetable proteins, phospholipid vegetable oils, ceramides, passion fruit ceramide, sphingolipids, whale sperm, lanolin almond oil, dicalpril carbonate, silicone elastomers, cyclomethicone;
  • - Wetting agents and / or moisturizing agents glycerine, propellant lenoglycol, hyaluronic acid, urea, PCA;
  • Conditioning agents quaternary ammonium salts, silicones, siloxanes.
  • SHIRWAIKAR A .; SETTY, M. M .; BOMMU, P .; KRISHNANAND, B. Effect of lupeol isolated from Crataeva nurvala Buch. - Ham. Stem bark extract against free radical induced nephrotoxicity in rats. Indian Journal of Experimental Biology, v. 42, no. 7, p. 686-690, 2004.
  • NICOLLIER G .
  • THOMPSON A.C. Flavonoids of Desmanthus illinoensis. Journal of Natural Products, v. 63, no. 1, p. 113-117, 1983.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Botany (AREA)
  • Biotechnology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

La présente invention concerne des extraits de plantes appartenant au genre Sclerolobium, des procédés pour leur obtention et des préparations cosmétiques et pharmaceutiques contenant ces extraits. Lesdits extraits peuvent être obtenus au moyen d'extractions polaires et/ou non polaires, chaque fraction contenant différents antioxydants, tous utiles pour un traitement topique. L'invention concerne également l'utilisation de cet extrait dans des préparations cosmétiques et/ou pharmaceutiques à usage topique.
PCT/BR2010/000321 2009-09-30 2010-09-30 Extrait végétal normalisé, procédé de préparation d'extrait de plantes du genre sclerolobium, composition cosmétique, composition pharmaceutique et utilisation dudit extrait WO2011038472A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
BR112012009369A BR112012009369A2 (pt) 2009-09-30 2010-09-30 extrato vegetal padronizado, processo para preparação de extrato de plantas do gênero sclerolobium, composição cosmética, composição farmacêutica e uso do referido extrato

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0956806 2009-09-30
FR0956806A FR2950532B1 (fr) 2009-09-30 2009-09-30 Procede pour la preparation d'un extrait de plantes du genre sclerolobium, composition cosmetique et pharmaceutique comprenant cet extrait et utilisation dudit extrait

Publications (2)

Publication Number Publication Date
WO2011038472A1 true WO2011038472A1 (fr) 2011-04-07
WO2011038472A8 WO2011038472A8 (fr) 2011-08-11

Family

ID=42276746

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/BR2010/000321 WO2011038472A1 (fr) 2009-09-30 2010-09-30 Extrait végétal normalisé, procédé de préparation d'extrait de plantes du genre sclerolobium, composition cosmétique, composition pharmaceutique et utilisation dudit extrait

Country Status (3)

Country Link
BR (1) BR112012009369A2 (fr)
FR (1) FR2950532B1 (fr)
WO (1) WO2011038472A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2997855B1 (fr) * 2012-11-15 2015-02-13 Rocher Yves Biolog Vegetale Utilisation d'un extrait de saba senegalensis dans une composition cosmetique apaisante et/ou uniformisant la couleur de la peau
FR2997854B1 (fr) * 2012-11-15 2015-03-27 Rocher Yves Biolog Vegetale Utilisation d'un extrait de saba senegalensis dans une composition cosmetique anti-age
FR3059429B1 (fr) * 2016-11-30 2020-09-04 Laboratoires Arkopharma Procede permettant d'imputer une reponse non negative obtenue dans un test de mutation reverse sur bacteries, realise a partir d'une preparation pharmaceutique, cosmetique ou nutritionnelle, a au moins un constituant identifie comme mutagene in vitro

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11139952A (ja) * 1997-10-31 1999-05-25 Shiseido Co Ltd 美白用皮膚外用剤
WO2000003748A2 (fr) 1998-07-17 2000-01-27 The University Of Texas Southwestern Medical Center Compositions a base de triterpenes favorisant la pousse des cheveux
WO2000003749A2 (fr) 1998-07-17 2000-01-27 The University Of Texas Southwestern Medical Center Methode de regulation de la pousse des cheveux
US20030170332A1 (en) 2001-12-24 2003-09-11 Enzo Nutraceuticals Limited. Flavonoid extract
WO2004009575A1 (fr) 2002-07-19 2004-01-29 Fudan University Extrait de pollen de typhae, sa fabrication et son utilisation

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11139952A (ja) * 1997-10-31 1999-05-25 Shiseido Co Ltd 美白用皮膚外用剤
WO2000003748A2 (fr) 1998-07-17 2000-01-27 The University Of Texas Southwestern Medical Center Compositions a base de triterpenes favorisant la pousse des cheveux
WO2000003749A2 (fr) 1998-07-17 2000-01-27 The University Of Texas Southwestern Medical Center Methode de regulation de la pousse des cheveux
US20030170332A1 (en) 2001-12-24 2003-09-11 Enzo Nutraceuticals Limited. Flavonoid extract
WO2004009575A1 (fr) 2002-07-19 2004-01-29 Fudan University Extrait de pollen de typhae, sa fabrication et son utilisation

Non-Patent Citations (32)

* Cited by examiner, † Cited by third party
Title
AGRAWAL, P. K.: "Carbon-13 NMR of Flavonoids", 1989, ELSEVIER, pages: 564
ALBERTO JOSÉ CALVALHEIRO: "Validaçao de Sclerolobium spp. como fonte de antioxidantes naturais para cosméticos", 28 February 2007 (2007-02-28), XP002589924, Retrieved from the Internet <URL:http://www.bv.fapesp.br/en/projetos-pite/1045/validacao-sclerolobium-spp-fonte-antioxidantes-naturais/> [retrieved on 20100630] *
ANDRIKOPOULOS, N. K.; KALIORA, A. C.; ASSIMOPOULOU, A. N.; PAPA-PEORGIOU, V. P.: "Biological activity of some naturally occurring resins, gums and pigments against in vitro LDL oxidation", PHYTOTHERAPY RESEARCH, vol. 17, no. 5, 2003, pages 501 - 507
BROWN J E; KHODR H; HIDER R C; RICE-EVANS C A: "Structural dependence of flavonoid interactions with Cu2+ ions: implications for their antioxidant properties", THE BIOCHEMICAL JOURNAL, vol. 330, 1998, pages 1173 - 8
DIAS ET AL., PESQ. AGROPEC. BRAS, vol. 26, 1991, pages 69 - 76
DIAS, L. E.; ALVAREZ, V. H.; JUCKSCH, I.; BARROS, N. F. DE; BRIENZA JUNIOR, S, PESQUISA AGROPECUÁRIA BRASILEIRA, vol. 26, no. 1, 1991, pages 69 - 76
DIAS; DIAS, L. E.; BRIENZA JUNIOR; S., PEREIRA; C.A. ET AL.: "Confirmar!", 1991, article "Taxi-branco (Sclerolobium paniculatum Vogel), uma leguminosa arbórea na-tiva da Amazônia com potencial para recuperagao de areas degradadas", pages: 148 - 153
DURIGAN, G.; BAITELLO; JOAO BATISTA; FRANCO; GERALDO ANTÔNIO DAHER CORR6A; SIQUEIRA, MARINEZ FERREIRA DE: "Plantas do Cerrado Paulista: lm-agens de uma paisagem ameagada", PAGINAS & LETRAS, vol. 1, 2004, pages 475
DURINGAN, G. ET AL., PLANTAS DO CERRADO PAULISTA, 2004
FLEKHTER, O. B.: "Biological activity and pharmacological prospects of lupane terpenoids: I. natural lupane derivatives", RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, vol. 32, no. 1, 2006, pages 37 - 49
HE, H.; CAI, Y.; SUN, M.; CORKE, H: "Extraction and purification of squalene from Amaranthus grain", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 50, no. 2, 2002, pages 368 - 372
HE; HE, H.; CAI, Y.; SUN, M.; CORKE, H. ET AL.: "Extraction and purification of Squalene from Amaranthus grain", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 50, 2002, pages 368 - 372
KATSANDIS; KATSANIDIS, E.; ADDIS, P. B. ET AL.: "Novel HPLC analysis of Tocopherols, Tocotrienols, and Cholesterol in tissue", FREE RADICAL BIOLOGY & MEDICINE, vol. 27, no. 11-12, 1999, pages 1137 - 1140
KIM; KIM, M.; JUNG; H. R.; MIN, T ET AL.: "Purification, structure determination and biological activities of 20(29)-Lupen-3-ona from Daedalopsis tricolor (Bull, ex Fr.) Bond. Et Sing", BULLETIN OF THE KOREAN CHEMICAL SOCIETY, vol. 22, no. 1, 2001, pages 59 - 62
KOHEN, R.: "Skin antioxidants: their role in aging and in oxidative stress -new approaches for their evaluation", BIOMED. PHARMACOTHER., vol. 53, no. 4, 1999, pages 181 - 192
LEE, T.; QIU, F.; WALLER, G. R.; CHOU, C.: "Three new flavonoids from leaves of Acacia confusa", JOURNAL OF NATURAL PRODUCTS, vol. 63, no. 5, 2000, pages 710 - 712
MA, K.; HANO, Y.; QIU, F.; CHEN, Y.; NOMURA, T.: "Determination of the absolute stereochemistry of lupane triterpenoids by fucofuranoside method and ORD spectrum", TETRAHEDRON LETTERS, vol. 45, no. 16, 2004, pages 3261 - 3263
MADUREIRA, A.M.; ASCENSO, J.R.; VALDEIRA, L.; DUARTE, A.; FRADE, J.P.; FREITAS, G.; FERREIRA, M.J.U: "Evaluation of the Antiviral and Antimicrobial Activities of Triterpenes Isolated from Euphorbia segetalis", JOUMAL NATURAL PRODUCTS, vol. 17, 2003, pages 375 - 380
MAHATO, S. B.; KUNDU, A. P: "13C NMR spectra of pentacyclic triterpenoids - a compilation and some salient features", PHYTOCHEMISTRY, vol. 37, no. 6, 1994, pages 1517 - 1575
MARKHAM, K. R.; TERNAI, B.; STANLEY, R.; GEIGER, H.; MABRY, T. J.: "C-13 NMRstudies of flavonoids .3. naturally occurring flavonoid glycosides and their acylated derivatives", TETRAHEDRON, vol. 34, no. 9, 1978, pages 1389 - 1397
NICOLLIER, G.; THOMPSON, A. C: "Flavonoids of Desmanthus illinoensis", JOURNAL OF NATURAL PRODUCTS, vol. 63, no. 1, 1983, pages 113 - 117
PIETTA; PIETTA, P. G.: "Flavonoids as antioxidants", J. NAT. PROD., vol. 63, 2000, pages 1035 - 1042
PINNELL, S. R.: "Cutaneous photodamage, oxidative stress, and topical antioxidant protection", JOURNAL OF THE AMERICAN ACADEMY OF DERMATOLOGY, vol. 48, no. 1, 2003, pages 1 - 19
RAMIREZ-APAN; A.A.; PEREZ-CASTORENA, A.L.; DE VIVAR; A.R., Z., NATUR-FORSCH., vol. 59, 2004, pages 237 - 243
REYES, C. P.; NÚÑEZ, M. J.; JIMÉNEZ, I. A.; BUSSEROLLES, J.; ALCA-RAZ, M. J.; BAZZOCCHI, I. L.: "Activity of lupane triterpenoids from Maytenus species as inhibitors of nitric oxide and prostaglandin E2", BIOORGANIC & ME DICINAL CHEMISTRY, vol. 14, no. 5, 2006, pages 1573 - 1579
REYNOLDS, W. F.; MCLEAN, S.; POPLAWSKI, J.: "Total assignment of 13C e 1 H spectra of three isomeric triterpenol derivatives by 2D NMR: an investigation of the potencial utility of 1 H chemical shifts in structural investigations of complex natural products", TETRAHEDRON, vol. 42, no. 13, 1986, pages 3419 - 3428
SALEEM, M; AFAQ, F; ADHAMI VM ET AL.: "Lupeol modulates NF-kappa B and P13K/Akt pathways and inhibits skin cancer in CD-1 mice", ON-GONENE, no. 30, 2004, pages 5203 - 5214
SHIRWAIKAR, A.; SETTY, M. M.; BOMMU, P.; KRISHNANAND, B: "Effect of lupeol isolated from Crataeva nurvala Buch. - Ham. stem bark extract against free radical induced nephrotoxicity in rats", INDIAN JOURNAL OF EXPERIMENTAL BIOLOGY, vol. 42, no. 7, 2004, pages 686 - 690
SULTANA, S.; MOHAMMAD, S.; SHARMA, S.; KHAN, N: "Lupeol, a triterpene prevents free radical induced macromolecular damage and alleviates benzoyl peroxide induced biochemical alterations in murine skin", INDIAN JOURNAI OF EXPERIMENTAL BIOIOGY, vol. 41, no. 8, 2003, pages 827 - 831
URSINI, F.; MAIORINO, M.; MIRAZZONI, P.; ROVERI, A.; PIFFERI, G.: "A novel antioxidant flavonoid (IdB 1031) affecting molecular mechanisms of cellular activation", FREE RADICAL BIOIOGY & TV1EDICINE, vol. 16, no. 5, 1994, pages 547 - 53
VOIGT, RUDOLF; FAHR, ALFRED: "PHARMAZEUTISCHE TECHNOLOGIE FUER STUDIUM UND BERUF", 1 January 2000, DEUTSCHER APOTHEKER VERLAG, STUTTGART; DE, ISBN: 3-7692-2649-6, pages: 445 - 447, XP007910780 *
YEN, G.; WU, S.; DUH, P: "Extraction and identification of antioxidant components from the leaves of Mulberry (Morus alba L.)", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 44, no. 7, 1996, pages 1687 - 1690

Also Published As

Publication number Publication date
FR2950532A1 (fr) 2011-04-01
BR112012009369A2 (pt) 2016-06-07
FR2950532B1 (fr) 2012-06-22
WO2011038472A8 (fr) 2011-08-11

Similar Documents

Publication Publication Date Title
Bahorun et al. Antioxidant activities of Crataegus monogyna extracts
Tesoriere et al. Increased resistance to oxidation of betalain-enriched human low density lipoproteins
Obi et al. Prevention of carbon tetrachloride-induced hepatotoxicity in the rat by H. rosasinensis anthocyanin extract administered in ethanol
Indrianingsih et al. Antioxidant and α-glucosidase inhibitor activities of natural compounds isolated from Quercus gilva Blume leaves
Noman et al. Phytochemical analysis and anti-diabetic, anti-inflammatory and antioxidant activities of Loranthus acaciae Zucc. grown in Saudi Arabia
Lee et al. Antioxidant activity of the halophyte Limonium tetragonum and its major active components
AU2012208626B2 (en) Monoterpene derivatives of chalcone or dihydrochalcone and their use as depigmenting agents
KR20010098707A (ko) 화장품 조성물
JP2011514347A (ja) フェノール酸を含むアブラヤシ葉からの抽出物
WO2014068190A2 (fr) Compositions cosmétiques contenant des fragments d&#39;extraits d&#39;airelle rouge
AU2012208626A1 (en) Monoterpene derivatives of chalcone or dihydrochalcone and their use as depigmenting agents
KR20120139137A (ko) 식물 세포 내에 안정화된 활성 물질 및 그 제조방법
Bujor Extraction, identification and antioxidant activity of the phenolic secondary metabolites isolated from the leaves, stems and fruits of two shrubs of the Ericaceae family
KR102303170B1 (ko) 안틸리스 불네라리아 지상부의 알콜 추출물, 이를 수득하는 방법, 및 이를 포함하는 화장료 또는 약학 조성물
WO2011038472A1 (fr) Extrait végétal normalisé, procédé de préparation d&#39;extrait de plantes du genre sclerolobium, composition cosmétique, composition pharmaceutique et utilisation dudit extrait
US10695283B2 (en) Extract of Greyia radlkoferi and use thereof
EP3579929B1 (fr) Extraits de la lianemarsdenia cundurango
KR100585486B1 (ko) 복분자 나무 추출물 또는 이로부터 유래한 화합물을포함하는 항산화성 조성물
KR100836941B1 (ko) 차가버섯으로부터 분리된 항산화 화합물 및 이를 포함하는 조성물
JP2006232807A (ja) 西洋わさび抽出物を含む抗酸化剤
KR20070078167A (ko) 감귤에서 나리루틴을 분리하는 방법
KR100453217B1 (ko) 피부미백재
KR100966837B1 (ko) 피부 미백 활성을 갖는 쿠마로일 화합물
US6428826B1 (en) Chilco product and method of making and using same
JP2000198726A (ja) 過酸化脂質生成抑制剤及びこれを含有する組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10778539

Country of ref document: EP

Kind code of ref document: A1

DPE1 Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10778539

Country of ref document: EP

Kind code of ref document: A1

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112012009369

Country of ref document: BR

ENP Entry into the national phase

Ref document number: 112012009369

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20120330