EP2262518A1 - Extrait de feuille de palmier à huile qui comprend des acides phénoliques - Google Patents

Extrait de feuille de palmier à huile qui comprend des acides phénoliques

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Publication number
EP2262518A1
EP2262518A1 EP09718003A EP09718003A EP2262518A1 EP 2262518 A1 EP2262518 A1 EP 2262518A1 EP 09718003 A EP09718003 A EP 09718003A EP 09718003 A EP09718003 A EP 09718003A EP 2262518 A1 EP2262518 A1 EP 2262518A1
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EP
European Patent Office
Prior art keywords
extract
composition
acid
oil palm
palm leaves
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP09718003A
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German (de)
English (en)
Other versions
EP2262518A4 (fr
Inventor
Nyie Lin Phang
Khalid Mohd. Fairuz Yasmin Abdul
Chai Kuan Lim
Siti Asmah Hambali
Sharharfiza Shariff
Sangeetha Thuraisngam
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nova Laboratories Sdn Bhd
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Nova Laboratories Sdn Bhd
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Publication date
Application filed by Nova Laboratories Sdn Bhd filed Critical Nova Laboratories Sdn Bhd
Publication of EP2262518A1 publication Critical patent/EP2262518A1/fr
Publication of EP2262518A4 publication Critical patent/EP2262518A4/fr
Withdrawn legal-status Critical Current

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    • 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)
    • A61K36/889—Arecaceae, Palmae or Palmaceae (Palm family), e.g. date or coconut palm or palmetto
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/12—Ophthalmic agents for cataracts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Definitions

  • This invention relates to extracts from oil palm leaves that have therapeutic activities for me reduction or prevention of oxidative stress in human and lower animals.
  • this invention relates to a fraction of the extracts that are enriched with (-)- catechin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid that possess the said therapeutic activities.
  • the oil palms ⁇ Elaeis comprise two species of the Arecaeeae, or palm family.
  • the African oil palm Elaeis guineensis is native to West Africa, while the American oil palm Elaeis oleifera is native to tropical Central America and South America.
  • Elaeis guineensis is also widely cultivated in Malaysia and Indonesia for its oil producing fruits.
  • Mature oil palm trees are single-stemmed, and grow to 20 meter tall.
  • the leaves or fronds are pinnate and can grow up to 3 - 5 meter long.
  • a young tree produces about
  • the fruit is reddish and grows in large bunches which can weight between 10 to 40 kilogram each.
  • the fruit comprises an oily and fleshy outer layer called pericarp, and with a single seed called palm kernel. Oil is extracted from both the pericarp and the palm kernel.
  • Oil palms are grown mainly for their fruits which are used mainly for the production of edible oil. Palm oil extracted from oil palm fruits also contains carotenes, tocopherols and tocotrienols. Some studies have been done on the beneficial effects of extracts derived from oil palm leaves. Abeywardena M 3 et al (Asia Pac. J. Clin. Nutr., 11: S467 - S 472) discloses a polyphenol-enriched extract derived from leaves of oil palm (Elaeis guineensis). The said extract can be used to promote vascular relaxation via endothelium-dependent mechanisms. The presence of (-)-catechin gallate, ferulic acid, gallic acid, and protocatechuic acid were not studied or disclosed. The use of this extract as anti- oxidative stress agent was not studied or disclosed.
  • Nagendran Balasundram, et al discloses a phenolic-rich fraction isolated from oil palm fruits. This extract exhibits bioactive properties, in particular antioxidant effects.
  • the chemical composition of the extract derived from oil palm leaves was not studied or disclosed.
  • the use of the extract derived from oil palm leaves as anti-oxidative stress agent was also not studied or disclosed.
  • Tan Y. A., et al discloses the presence of phenolic compounds in palm oil that is derived from oil palm mesocarp and kernel, which is from the oil palm fruit
  • phenolic compounds include gallic, chlorogenic, protocatechuic, gentisic, coumaric, ferulic and caffeic acids, as well as catechins, hesperidine, narirutin, and 4-hydroxybenzoate.
  • the chemical composition of the extract derived from oil palm leaves was not studied or disclosed.
  • the use of the extract derived from oil palm leaves as anti-oxidative stress agent was also not studied or disclosed.
  • Run-Cang Sun, et al J. Agric. Food Chem., 49 (11), 5122-5129, 2001 discloses a new method of quantitative determination of hydroxycmnamic acids in oil palm leaf fiber.
  • the presence of (-)-catechin gallate was not studied or disclosed.
  • the use of this extract as anti-oxidative stress agent was not studied or disclosed.
  • Yew-Ai Tan, et al discloses the presence of phytochemicals such as sterols, vitamin E, carotenoids, phospholipids, squalene, and phenolics from the by-products of palm oil milling and refining, that is from the fruits of oil palm.
  • phytochemicals such as sterols, vitamin E, carotenoids, phospholipids, squalene, and phenolics from the by-products of palm oil milling and refining, that is from the fruits of oil palm.
  • the chemical composition of the extract derived from oil palm leaves was not studied or disclosed.
  • the use of the extract derived from oil palm leaves as anti-oxidative stress agent was also not studied or disclosed.
  • Kinnoudo Celestin discloses extracts of Elaeis guineensis (oil palm) leaves that possess antimalarial properties. The chemical content of these extracts is not characterized. The presence of (-)-catechin gallate, ferulic acid, gallic acid, and protocatechuic acid in the extract derived from oil palm leaves was not studied or disclosed. The use of these extracts as anti-oxidative stress agent was also not studied or disclosed.
  • a radical, or a free radical is generally understood as a molecule with one or more unpaired electrons in its outer orbital shell.
  • Many molecular species with bound radicals are monoxides or other oxygen containing compounds, generally referred to as reactive oxygen species (ROS).
  • ROS reactive oxygen species
  • These highly unstable molecules tend to react rapidly with adjacent molecules, donating, abstracting, or even sharing their outer orbital electron(s). This reaction not only changes the adjacent, target molecule, sometimes in profound and beneficial ways, but it can also damage it, or alternatively the unpaired election can be passed along to the target, i.e., as in a free radical, generating a second unwanted ROS, which can then go on to react positively or detrimentally with a new target.
  • much of the high reactivity of ROS is due to their generation of such molecular chain reactions, effectively amplifying their effects many fold.
  • the shifting of this balance towards oxidative processes may have two reasons: i. overburden of the antioxidative system because of the production of an active oxygen metabolite, and/or ii. insufficiency of the antioxidative system.
  • oxidative stress oxidative stress
  • diseases such as hepatitis, diseases of central nervous system such as epilepsy or Parkinson's disease, diseases of the pulmonary organs such as asthma, psoriasis, side-effects of anticancer agents, chemicals such as paraquat and side-effects of radiation as well as diseases of the coronary circulation such as cardiac infarction.
  • inflammatory diseases such as hepatitis, diseases of central nervous system such as epilepsy or Parkinson's disease
  • diseases of the pulmonary organs such as asthma, psoriasis, side-effects of anticancer agents, chemicals such as paraquat and side-effects of radiation as well as diseases of the coronary circulation such as cardiac infarction.
  • oxidative stress has been implicated as a factor in various diseases and injury states in man and animals; while this does not mean that oxidative stress is the cause of these diseases, it does testify, as confirmed by a number of studies, that oxidative stress can have a negative influence on the progress of said diseases, causing further damage to the cells of an organism that is already sick.
  • Kidney Autoimmune nephritic syndromes, Heavy metal nephrotoxicity.
  • Lung Lung cancer (cigarette smoke), Emphysema, Oxidant pollutants (O 3 , NO 2 ), Bronchopulmonary dysphasia, Asbestos carcinogenicity.
  • Nervous System disorders Parkinson's disease, Neuronal ceroid lipofuscinoses,
  • Alzheimer's disease Muscular dystrophy, Multiple sclerosis.
  • Iron Overload Idiopathic hemochromatosis, Dietary overload, Thalassemia.
  • mflammatory-Irnmune Injury Glomerulonephritis, Autoimmune disease, Rheumatoid arthritis.
  • Liver Liver injuries induced by alcohol, halogenated hydrocarbons, and paracetamol.
  • Antioxidants afford protection because they can scavenge ROS and free radicals before they cause damage to the various biological molecules, or prevent oxidative damage from spreading, i.e., by interrupting the radical chain reaction of lipid peroxidation.
  • the reactivity of radicals in the body, and the burden on the body that results in eventual pathological conditions, is known as oxidative stress.
  • Vitamins such as vitamin C and vitamin E, both of which are found in foods and available as supplements, help the body reduce effects of oxidative stress.
  • a more powerful combatant against the free radicals and ROS is the body's own self defense system of naturally produced chemicals called antioxidants. These antioxidants act to terminate the propagation of free and bound radicals on ROS either by giving an electron to the free radical or ROS or by hindering their formation.
  • the body's antioxidant defense system includes three important natural antioxidants: superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPX). Studies conducted have indicated that these antioxidants can work synergistically as the reactions they catalyze are metabolically sequential, beginning first with SOD followed by the actions of CAT and GPX.
  • the body's antioxidant defense system is constantly subject to oxidative stress, and its ability to produce SOD, CAT, and GPX is compromised by the aging process and can further be impaired by inflammation, microbial or viral infections, the progression of cancer and neurological disorders, and other pathological conditions that produce, are caused by, or are exacerbated by oxidative stress.
  • the present invention seeks to provide a novel extract of oil palm leaves that is useful in reducing oxidative stress in mammals and poultry.
  • the said extract which is enriched with (-)-catechm gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid has anti-oxidative stress activity, and the combined effect of (-)-catecbin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid in the extracts of oil palm leaves have not been reported before.
  • polyphenol enriched fractions of extracts derived from oil palm leaves have been disclosed and the said fractions can be used as anti-hypercholesterolemic and anti-hypertensive agents, but fraction derived from oil palm leaves containing (-)- catechin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid was not studied or disclosed The use of the said extract as anti-oxidative stress agent was not studied or disclosed.
  • It is another object of the present invention to provide a composition comprising (-)- catechin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid.
  • It is yet another object of the present invention to provide a pharmaceutical composition comprising the novel extract, stabilizers, carriers, excipients, extenders, and other suitable substances.
  • It is a further object of the present invention to provide a composition comprising the novel extract, in admixture and in association with pharmaceutical carriers, for use in reducing and preventing oxidative stress in mammals and poultry.
  • compositions comprising an extract from oil palm leaves characterized in that; the said extract comprising (-)-catechin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid, and a method for producing an extract of oil palm leaves, containing (-)-catechin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid using the steps of: a) extracting the herbal liquid from dried or fresh oil palm leaves, by mixing with water, ethanol, methanol, acetone, ethyl acetate, chloroform, isopropyl alcohol or mixture of these said solvents, or any other polar solvents, and heating at a temperature ranging from 25 0 C to 95 0 C for 0.5 to 96 hours; b) filtering the herbal liquid extract obtained in (a); c) contacting the filtered herbal liquid extract obtained in (b) with an adsorptive chromatographic medium which adsorb
  • Figure 1 shows the HPLC identification of (-)-catechin gallate in extract of oil palm leaves.
  • Figure 2 shows the TLC identification of ferulic acid in extract of oil palm leaves.
  • Figure 3 shows the HPLC identification of gallic acid in extract of oil palm leaves.
  • Figure 4 shows the HPLC quantification of (-)-catechin gallate in extract of oil palm leaves.
  • Figure 5 shows the HPLC quantification of ferulic acid in extract of oil palm leaves.
  • Figure 6 shows the UV quantification of total phenolic acids in extract of oil palm leaves.
  • the invention relates to compositions comprising extracts from the oil palm leaves characterized by the said extracts comprising (-)-catechin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid.
  • the said oil palm leaves of this invention include leaves of plants selected from the group of plant genus Elaeis consisting oiEl ⁇ eis guineensis or El ⁇ eis oleifer ⁇ .
  • the novel composition of the present invention comprises from about 0.1% to about 95% by weight of (-)-catechin gallate, from about 0.1% to about 95% by weight of ferulic acid, and from about 0.1% to about 95% by weight of total phenolic acids such as gallic acid and protocatechuic acid.
  • the composition comprises from about 0.5% to about 10% by weight of (-)-catecbin gallate, from about 1% to about 5% by weight of ferulic acid, and from about 5% to about 30% by weight of total phenolic acids such as gallic acid and protocatechuic acid.
  • the-composition comprises about 0.5% by weight of (-)-catechin gallate, about 1% by weight of ferulic acid, and about 20% by weight of total phenolic acids such as gallic acid and protocatechuic acid.
  • the present invention further relates to a method for producing such an extract of oil palm leaves, comprising steps of: a) extracting the herbal liquid from dried or fresh oil palm leaves, by mixing with water, ethanol, methanol, acetone, ethyl acetate, chloroform, isopropyl alcohol, or mixture of these said solvents, or any other polar solvents, and heating at a temperature ranging from 25 0 C to 95 0 C for 0.5 to 96 hours; b) filtering the herbal liquid extract obtained in (a); c) contacting the filtered herbal liquid extract obtained in (b) with an adsorptive chromatographic medium which selectively adsorbs the fraction in which (-)- catechin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid are present, such adsorption medium may be column adsorption medium, or any other adsorption medium; d) eluting the said fraction obtained in (c) from the adsorptive chromatographic medium
  • 1 part of oil palm leaves (dry basis) is extracted with from about 5 to about 50 parts, preferably from about 10 parts to about 30 parts of solvent using an extraction apparatus where the solvent is mixed with the oil palm leaves for a period of time, preferably from about 1 hour to 96 hours, more preferably for 8 hours to 24 hours.
  • the temperature of the solvent is maintained preferably from about 25 0 C to about 95 0 C 5 more preferably from about 50 0 C to 60 0 C.
  • the preferred solvents for the extraction include water, ethanol, isopropyl alcohol, or mixture of these said solvents, and more preferably water, ethanol, or mixture of water and ethanol, and most preferably a mixture of 30% by weight of water and 70% by weight of ethanol.
  • the adsorptive chromatographic medium includes styrene-divinylbenzene copolymer resin, phenol-formaldehyde resin, acrylic resin, methacrylate resin, and polyamide resin.
  • styrene-divinylbenzene copolymer resin examples include styrene-divinylbenzene copolymer resin, phenol-formaldehyde resin, acrylic resin, methacrylate resin, and polyamide resin.
  • styrene-divinylbenzene copolymer resin phenol-formaldehyde resin
  • acrylic resin methacrylate resin
  • polyamide resin examples of such a resin are: Amberlite XAD-I, Amberlite XAD-2, Amberlite XAD-4, Amberlite XAD-7, Amberlite XAD-8, Amberlite XAD-Il, Amberlite XAD-12, Amberlite XAD-1180,
  • the resins are styrene- divinylbenzene copolymer resins manufactured under trade names such as: AB-8 Crosslinked polystyrene (product of Tianjin Nankai Hecheng Science and Technology Co., Ltd, Tianjin, China), Amberlite XAD 1180, Amberlite 7HP, and Amberlite 761
  • the resin is styrene- divinylbenzene copolymer resins manufactured under trade name AB-8 Crosslinked polystyrene (product of Tianjin Nankai Hecheng Science and Technology Co., Ltd, Tianjin, China).
  • Eluting solvents for eluting the enriched fraction from the adsorptive chromatographic medium may be water, ethanol, methanol, acetone, ethyl acetate, chloroform, isopropyl alcohol, or mixture of the said solvents, or any other polar solvents known to persons skilled in the art.
  • the preferred solvent is mixture of water and ethanol, and most preferably is 30% aqueous ethanol.
  • drying method includes the use of a spray dryer, vacuum oven, or conventional oven, and most preferably the use of a spray dryer.
  • Equipment for producing an extract of oil palm leaves of the present invention comprises: herbal extraction tank, adsorptive chromatographic column, and dryer.
  • the herbal extraction tank is constructed with steam jacket and a speed agitator that stirs the tank's content. Steam is passed through the steam jacket to heat the content of the tank.
  • Oil palm leaves are mixed with water, ethanol, methanol, acetone, ethyl acetate, chloroform, isopropyl alcohol, or mixture of the said solvents, or any other polar solvents known to persons skilled in the art and heated in an herbal extraction tank at a temperature in the preferable range of 25 0 C to 95 0 C for 1 to 96 hours. The heating process produces an herbal extract liquid, which is then filtered to collect the filtrate.
  • the adsorptive chromatographic column is filled with adsorptive chromatographic resin, preferably comprises of polystyrene resin.
  • the filtered herbal extract liquid is passed through the adsorptive chromatographic column whereby the fraction enriched in (-)-catechin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid is adsorbed in the surface of the said resin.
  • the said enriched fraction contained (-)-catechin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid is then eluted by ehiting the adsorptive chromatographic column with water, methanol, ethanol, acetone, ethyl acetate, chloroform, isopropyl alcohol, or mixture of the said solvents, or any other polar solvents.
  • the resultant enriched fraction of herbal liquid is finally dried by using spray dryer, vacuum oven, conventional oven; microwave oven, freeze dryer or other dyers which are apparent to those skilled in the art.
  • a method of identifying the presence of (-)-catechin gallate in an extract of oil palm leaves by using HPLC a) A reference standard solution of (-)-catechin gallate is prepared by dissolving 1 mg of (-)-catechin gallate reference standard in 1 ml of 0.1% phosphoric acid; b) A test solution is prepared by dissolving 200 mg of extract of the present invention in 10 ml of ethanol ; c) These two solutions are injected separately into a HPLC system with the following conditions:
  • the solvent mixture is started at 92% of solvent (i) and 8% of solvent (ii) and is increased to 31% of solvent (ii) in 50 minutes with linear gradient.
  • the chromatograms obtained from reference standard solution and test solution showed a major peak at retention time about 28 minutes corresponding to (-)-catechin gallate. The presence of the peak confirmed the presence of (-)-catechin gallate in the composition of the present invention.
  • a method of identifying the presence of ferulic acid in an extract of oil palm leaves by using TLC Identification a) The sample is prepared by dissolving the extract of the present invention in HPLC grade methanol, centrifuging at 4000 rpm for 15 minutes and collecting the supernatant b) The sample is first spotted on a pre-coated silica gel 60 TLC plate (E-Merck), along with known amount of ferulic acid reference standard, using a solvent phase consisting of a mixture of methanol / water (ratio 7:1). c) The plate is air dried and visualized under Ultra Violet (UV) lamp at wavelength 254 nm.
  • UV Ultra Violet
  • Light purple principal zones corresponding to ferulic acid were observed in both reference standard and sample solutions. The presence of the light purple principal zones confirmed the presence of ferulic acid in the composition of the present invention.
  • a method of identifying the presence of gallic acid in an extract of oil palm leaves by using HPLC a) A reference standard solution of gallic acid is prepared by dissolving 10 mg of gallic acid reference standard in 10 ml of methanol; b) A test solution is prepared by dissolving 200 mg of extract of the present invention in 10 ml of methanol; c) These two solutions are injected separately into a HPLC system with the following conditions:
  • a method of quantitative determination of the total amount of (-)-catechin gallate in an extract of oil palm leaves by using HPLC a) A reference standard solution of (-)-catechin gallate is prepared by dissolving 1 mg of (-)-catechin gallate reference standard in 1 ml of 0.1 % phosphoric acid; b) A test solution is prepared by dissolving 200 mg of extract of the present invention in 10 ml of ethanol; c) These two solutions are injected separately into a HPLC system with the following conditions: Equipment: Perkin Elmer series 200 LC
  • a peak area of (-)-catechin gallate was obtained at retention time about 28 minutes from the HPLC data.
  • the amount of (-)-catechin gallate in the test solution is obtained by comparing with the reference standard solution of (-)-catechin gallate.
  • W weight (mg) of sample taken to prepare the test solution (mg)
  • r t peak area of (-)-catechin gallate obtained from the test solution
  • r s peak area of (-)-catechin gallate obtained from the reference standard solution
  • a method of quantitative determination of the total amount of ferulic acid in an extract of oil palm leaves by using HPLC a) Reference standard solutions of ferulic acid with four known concentrations of ferulic acid reference standard 0.15 mg/ml, 0.20 mg/ml, 0.25 mg/ml, and 0.5 mg/ml are prepared by dissolving ferulic acid reference standard in 70% ethanol; b) A test solution is prepared by dissolving 10 mg of an extract of oil palm leaves of the present invention in 10 ml of 70% ethanol; c) HPLC assays were carried out on these solutions by injecting separately into a HPLC system with the following conditions:
  • a peak area of ferulic acid was obtained at retention time about 28.8 minutes from the HPLC data.
  • the amount of ferulic acid in the test solution is obtained by comparing with the reference standard solution of ferulic acid.
  • W weight (mg) of sample taken to prepare the test solution (mg)
  • r t peak area of ferulic acid obtained from the test solution
  • r s peak area of ferulic acid obtained from the reference standard solution
  • a method of quantitative determination of the total amount of phenolic acids in an extract of oil palm leaves of the present invention comprising steps of: a) A reference standard solution is prepared by dissolving 10.0 mg of protocatechuic acid reference standard in 100 ml of HPLC grade methanol.
  • 10 ml of the solution is diluted with HPLC grade methanol at a ratio of 1:9; b) A test solution is prepared by dissolving 10 mg of the extract of oil palm leaves in 10 ml of 70% ethanol; c) 0.9% potassium ferricyanide aqueous solution is prepared by dissolving 90 mg of Potassium ferriccyanide in 10 ml of purified water; d) 0.9% ferric chloride aqueous solution is prepared by dissolving 90 mg of ferric chloride in 10 ml of purified water; e) Chromogemc reagent is prepared by mixing 9 ml of 0.9% potassium ferricyanide aqueous solution with 10 ml of 0.9% ferric chloride aqueous solutioa
  • the present invention encompasses a therapeutic composition
  • a therapeutic composition comprising the extract prepared according to the present invention, wherein the composition is in the forms of tea, tablet, coated tablet, lozenge, chewable tablet, capsule, soft capsule, granule, coated granule, powder, coated powder, solution, syrup, emulsions, and suspension, useful in humans or lower animals for the reduction or prevention of oxidative stress.
  • the present invention encompasses a pharmaceutical composition
  • a pharmaceutical composition comprising an effective amount of the said extract, for example 1 mg to 800 mg, more preferably 300 mg to 500 mg, and a pharmaceutically acceptable carrier.
  • the present invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising the novel extract formulated for oral, buccal, rectal or transdermal administration or in a form suitable for administration by inhalation or insufflation (either through the mouth or the nose).
  • the pharmaceutical compositions may take the forms of, for example, tea, tablet, coated tablet, lozenge, chewable tablet, capsule, softgel capsules, granule, coated granule, powder, solution, syrup, emulsion or suspension prepared by conventional means with pharmaceutically acceptable excipients such as binding agents (e.g. pregelatinised maize starch, polyvinylpyrrolidone or hydroxypropyl methylcellulose); fillers (e.g. lactose, microcrystalline cellulose, starch or tricalcium phosphate); lubricants (e.g. magnesium stearate, talc or silica); disintegrants (e.g.
  • binding agents e.g. pregelatinised maize starch, polyvinylpyrrolidone or hydroxypropyl methylcellulose
  • fillers e.g. lactose, microcrystalline cellulose, starch or tricalcium phosphate
  • lubricants e.g. magnesium stearate, talc or silica
  • Liquid preparations for oral administration may take the form of, for example, solutions, syrups, emulsions, or suspensions or they may be presented as a dry product for constitution with water or other suitable vehicles before use.
  • Such liquid preparations may be prepared by conventional means with pharmaceutically acceptable additives such as suspending agents (e.g. sorbitol syrup, cellulose derivatives or hydrogenated edible fats); emulsifying agents (e.g. lecithin or acacia); non-aqueous vehicles (e.g.
  • preparations may also contain buffer salts, flavouring, colouring and sweetening agents as appropriate.
  • Preparations for oral administration may be suitably formulated to give controlled or extended release of the extract of the present invention.
  • compositions may take the form of tablets or lozenges formulated in a conventional manner.
  • compositions according, to the present invention may be formulated for administrations by nasal insufflation and oral inhalation.
  • types of preparation for the said administrations include sprays and aerosols for use in an inhaler or insufflator.
  • Transdermal preparation for external application may be formed with the aid of any suitable cream, ointment or lotion base known to those persons skilled in the art.
  • compositions according to the present invention may also be formulated in rectal compositions such as suppositories or retention enemas, e.g. containing conventional suppository bases such as cocoa butter or other fats and oils.
  • the pharmaceutical compositions include capsule, soft capsule, or tablet comprising from about 1% to about 95% of the said extract, and from about 1% to about 95% of a pharmaceutical acceptable carrier.
  • a pharmaceutical acceptable carrier means one or more compatible solid or liquid filled diluents, or any pharmaceutical excipients known to persons skilled in the art.
  • substances which can serve as pharmaceutically acceptable carriers are sugars such as lactose, glucose and sucrose, starch such as corn starch and potato starch, cellulose derivatives such as sodium carboxymethylcellulose, cellulose acetate, and microcrystalline cellulose.
  • a proposed dose of the composition according to the present invention for administration to a human is 0.1 mg to 1 g, such as 1 mg to 500 mg dose of the active ingredient per unit dose, expressed as the weight of dry extract.
  • the unit dose may be administered, for example, 1 to 4 times per day.
  • the dose will depend on the route of administration. It will be appreciated that it may be necessary to make routine variations to the dosage depending on the age and weight of the patient as well as the severity of the condition to be treated.
  • the dosage will also depend on the route of administration. The precise dose and route of administration will ultimately be at the discretion of the attendant physician or veterinarian.
  • the extract prepared according to the present invention demonstrates anti-oxidant effect and free radical scavenging effect in in vitro test models, and anti-oxidative stress effect in in vivo test model.
  • the extract is used for reducing or preventing oxidative stress in mammals and poultry by administering to a subject in need of such treatment an effective amount of the composition.
  • compositions made according to the invention are set forth below. Toxicity studies performed on the composition of the present invention has proven that the extract is non-toxic at an oral dose of 30 g of extract of oil palm leaves / kg of body weight in Sprague-Dawley rats. According, oral dosage in humans of 0.03 g of extract of oil palm leaves per kg body weight per day is considered appropriate and safe.
  • Extract of Oil Palm Leaves About 50 g of dried oil palm leaves were extracted with about 500 mL of a mixture of water/ethanol (ratio 3:7 by volume), at about 60-65 0 C for approximately 60 minutes. The resulting slurry was filtered through two layers of muslin cloth and yielded about 502 g of crude extract liquid.
  • the resulting crude extract liquid was then subjected to column adsorptive chromatography.
  • Amberlite XAD 16HP Manufactured by Rohm & Haas
  • the column was washed with about 4-5 column volumes of deionized water.
  • the crude extract liquid from the foregoing extraction step was pumped into the column.
  • the column was first eluted with 1500 ml of deionized water to remove salts, sugars, and other unwanted hydrophilic substances.
  • the column was then eluted with 1500 ml of a mixture of water/ isopropanol (ratio 3:7 by volume) with a constant flow rate of 25 ml / minute at a temperature of 6O 0 C and a pressure of 0.5 to 1 bar to yield a purified eluant liquid enriched in (-)- catechin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid.
  • the resulting eluant liquid was further concentrated in a rotary evaporator to 50 ml and the concentrated liquid was dried in a vacuum oven at 60 0 C for 8 hours.
  • the crude extract liquid was separated from the leaves by filtering through a cartridge filter with pore size of 10 ⁇ m.
  • the resulting concentrated fluid extract was subjected to adsorptive column chromatography by using a stainless steel column of 15 cm diameter and 150 cm length.
  • the column was packed with polyamide resin with particle size ranging from 30-60 mesh.
  • the column was then washed with 200 litres of deionized water followed by elution with 200 litres of a mixture of water/isopropyl solution (ratio 3:7 by volume) with a constant flow rate of about 1.5 litre / minute at a temperature of about 20-30 0 C and at a pressure of about 0.5 to 1 bar to yield a purified eluant liquid enriched in (-)-catechin gallate, ferulic acid, and phenolic acids such as gallic acid and protocatechuic acid.
  • the resulting eluant liquid was then spray dried in a spray dryer.
  • the inlet temperature in the spray dryer was set at about 170 0 C to about 180 0 C and the outlet temperature was set at about 100 0 C to about 105 0 C.
  • Example 1 a test solution of the extract of the present invention obtained in Example 1 was prepared by dissolving 200 mg of extract to be analyzed in 10 ml of ethanol.
  • Example 2 The extract powder of oil palm leaves obtained in Example 1 was dissolved in HPLC grade methanol, centrifuged at 4000 rpm for 15 minutes and the supernatant was collected. The sample was first spotted on a pre-coated silica gel 60 TLC plate (E-
  • the plate was air dried and visualized under Ultra Violet (UV) lamp at wavelength 254 urn. Light purple principal zones corresponding to ferulic acid were observed in both reference standard solution and test solution (as shown in Figure 2).
  • UV Ultra Violet
  • Example 1 10 mg of gallic acid reference standard was dissolved in 10 ml of methanol to form the reference standard solution.
  • a test solution of the extract of the present invention obtained in Example 1 was prepared by dissolving 200 mg of extract to be analyzed in 10 ml of methanol.
  • the chromatograms obtained from reference standard solution and test solution showed a major peak at retention time about 6.6 minutes corresponding to gallic acid.
  • HPLC method was used to determine the amount of (-)-catechin gallate in the extract of oil palm leaves obtained in Example 1.
  • Example 1 1 mg of (-)-catechin gallate reference standard was dissolved in 1 ml of 0.1% phosphoric acid to form the reference standard solution.
  • a test solution of the extract of the present invention obtained in Example 1 was prepared by dissolving 200 mg of extract to be analyzed in 10 ml of ethanol.
  • HPLC assays were carried out on these solutions by injecting separately into a HPLC system with the following conditions:
  • the solvent mixture is started at 92% of solvent (i) and 8% of solvent (ii) in 50 minutes with linear gradient.
  • a peak area of (-)-catechin gallate was obtained at retention time about 28 minutes from the HPLC data (as shown in Figure 4).
  • the amount of (-)-catechin gallate in the test solution was obtained by comparing with the reference standard solution of (-)-catechin gallate.
  • the content of (-)-catechin gallate in the test solution in percentage (%) was calculated by using the following equation:
  • the HPLC assays showed that the amount of (-)-catechin gallate present in the composition obtained in Example 1 was 1.1%.
  • Reference standard solutions of ferulic acid with four known concentrations of ferulic acid reference standard 0.15 mg / ml, 0.20 mg / ml, 0.25 mg / ml, and 0.5 mg / ml were prepared by dissolving ferulic acid reference standard in 70% ethanol.
  • a test solution of the extract of the present invention obtained in Example 1 was prepared by dissolving 10 mg of extract to be analyzed in 10 ml of 70% ethanol.
  • HPLC assays were carried out on these solutions by injecting separately into a HPLC system with the following conditions: Equipment: Perkin Elmer series 200 LC Column: Hypersil BDS C 18 column (250 mm x 4.6 mm ID, 5 ⁇ m particle size)
  • a peak area of ferulic acid was obtained at retention time about 28.8 minutes from the HPLC data (as shown in Figure 5).
  • the amount of ferulic acid in the test solution was obtained by comparing with the reference standard solution of ferulic acid.
  • the content of ferulic acid in the test solution in percentage (%) was calculated by using the following equation: 1000 Cr t / Wr 5 where:
  • W weight (mg) of sample taken to prepare the test solution (mg)
  • i t peak area of ferulic acid obtained from the test solution
  • r s peak area of ferulic acid obtained from the reference standard solution
  • HPLC assays showed that the amount of ferulic acid present in the composition obtained in Example 1 was 1.5%.
  • UV spectrophotometry method was used to determine the amount of total phenolic acids in extract of oil palm leaves obtained in Example 1.
  • the standard and blank solutions were left in dark room for 5 minutes. Each flask were made up to volume with 0. IM HCl and mixed well. The solutions were left in dark room for 20 minutes. The absorbance of standard solutions were measured at 697 run against the blank solution. A standard calibration curve was plotted by using concentration of standard solutions as axis-x and absorbance as axis-y.
  • the assay was performed according to the UV spectrophotometry method by dissolving the composition with 10 ml of 70% aqueous ethanol; pipetting 0.05 ml of the solution into a flask and the test solution was prepared by using the same method as above.
  • the concentration of total phenolic acids from the standard calibration curve was calculated.
  • composition for the present invention Determination of antioxidant activity of composition for the present invention by in vitro and in vivo models.
  • Antioxidant activity of the composition for the present invention was determined by using in vitro and in vivo models as follows:
  • DPPH free radical scavenging activity of the composition of the present invention was determined by using l,l-diphenyl-2-picryl-hydrazil (DPPH) colorimetry with detection at 517 nm. The activity was evaluated by the decrease in the absorbance as a result of DPPH color change from purple to yellow.
  • DPPH l,l-diphenyl-2-picryl-hydrazil
  • Table 1 Percentage (%) of DPPH free radical scavenging activity of extract of oil palm leaves vs BHA EXAMPLE lO Reducing Power of the Composition for the present composition
  • Reducing power of the composition of the present invention obtained in Example 1 was determined according to potassium ferricyanide reduction method. 10 mg of sample powder obtained in Example 1 above was dissolved in 10 ml of absolute ethanol as sample solution. 1 ml of the sample solution was dissolved in 1 ml of distilled water and mixed with 2.5 ml of 0.2 mol / L phosphate buffer and 2.5 ml of 1% potassium ferricyanide aqueous solution. The mixture was incubated at 50 0 C for 20 minutes. 2.5 ml of 10% trichloroacetic acid aqueous solution was then added to each sample solution. The sample solution was centrifuged at 3000 rpm for 10 minutes.
  • Anti-oxidative stress activity of extract of oil palm leaves can be demonstrated by determining the lipid peroxidation inhibitory property of extract of oil palm leaves in Malondialdehyde (MDA) test.
  • MDA Malondialdehyde
  • One of the most devastating effects of oxidative stress by free radicals in the organism is the oxidation of lipids, resulting in the formation of Malondialdehyde (MDA).
  • MDA Malondialdehyde
  • the level of lipid peroxidation can be assessed by measuring the level of thiobarbituric acid reactive substances (TBARS) in serum of lipid peroxidation-induced animals.
  • MDA reacts with thiobarbituric acid to form a colored substance which can be measured calorimetrically. Lipid peroxidation was induced by intraperitoneal injection of carbon tetrachloride
  • the serum MDA levels were higher in lipid peroxidation- induced rats (Positive Control group) compared to rats in the Control group. There was a decrease in the level of serum MDA in the rats treated with the composition obtained in Example 1 (Treatment group), indicating the lipid peroxidation inhibitory effect and anti-oxidative stress activity of oil palm leaf extracts.
  • compositions were administered orally to groups of 3 rats weighing about 150 -
  • compositions were dissolved in purified water before single oral dose was given to each animal. Purified water was orally administered, to the same number of rats in the control group. Animals were observed individually 30 minutes after dosing, periodically during the first 24 hours, with special attention given during the first 4 hours and daily thereafter, for a total of 14 days.
  • a tablet with the following formulation was prepared as described below.
  • composition of the following formulation was prepared in hard capsule by standard method known to those skilled in the art.
  • the resulting mixture was then filled into a size #1 hard gelatin capsule.
  • a liquid oral suspension with the following composition was prepared as follows:
  • Oil palm leaf extract powder of the present invention was then filled into an amber glass bottle.

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Abstract

La présente invention concerne une composition comprenant un extrait de feuilles de palmier à huile caractérisée en ce que l’extrait comprend du gallate de (-)-catéchine, de l’acide férulique, et des acides phénoliques tels que l’acide gallique et l’acide protocatéchique et un procédé de production dudit extrait qui comprend les étapes consistant à (a) extraire les feuilles de palmier à huile sèches ou fraîches avec un solvant, (b) filtrer l’extrait obtenu à l’étape (a), (c) mettre en contact l’extrait filtré de l’étape (b) avec un milieu chromatographique qui absorbe sélectivement une fraction contenant du gallate de (-)-catéchine, de l’acide férulique, et des acides phénoliques, (d) éluer ladite fraction du milieu chromatographique en utilisant un solvant, (e) sécher la fraction éluée obtenue dans l’étape (d). La présente invention concerne également l’utilisation de la composition pour réduire ou empêcher le stress oxydatif chez les mammifères et la volaille.
EP09718003A 2008-03-06 2009-02-12 Extrait de feuille de palmier à huile qui comprend des acides phénoliques Withdrawn EP2262518A4 (fr)

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MYPI20080538A MY157650A (en) 2008-03-06 2008-03-06 Extract from oil palm leaves comprising phenolic acids
PCT/MY2009/000028 WO2009110782A1 (fr) 2008-03-06 2009-02-12 Extrait de feuille de palmier à huile qui comprend des acides phénoliques

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US20110189222A1 (en) * 2008-09-30 2011-08-04 Suhaila Mohamed Composition for wound healing
MY161839A (en) 2009-05-18 2017-05-15 Malaysian Palm Oil Board A composition for use in the prevention and treatment of cardiovascular diseases
MY185582A (en) 2010-01-07 2021-05-24 Malaysian Palm Oil Board Anti-obesity and anti-dyslipidemic effects of oil palm phenolics in preventing atheroslerosis and cardiovascular disease
CN102504706B (zh) * 2011-11-21 2013-07-10 陈永刚 稀土漆面护理液
TW201741663A (zh) 2011-12-29 2017-12-01 陶氏農業科學公司 利用鹼皂化作用來對植物組織樣本總油含量進行比色測定之技術
US11071313B2 (en) 2013-02-20 2021-07-27 Palm Silage, Inc. Palm-based animal feed
US11064717B2 (en) 2013-02-20 2021-07-20 Palm Silage, Inc. Palm-based animal feed
MY179462A (en) * 2013-10-11 2020-11-06 Malaysian Palm Oil Board Protective effects of oil palm composition on alzheimer?s disease
CN103642850A (zh) * 2013-12-10 2014-03-19 江南大学 一种阿魏酸体外抗氧化活性的测定方法
US20160278416A1 (en) * 2015-03-24 2016-09-29 Malaysian Palm Oil Board (Mpob) Methods for producing water soluble oil palm leaf powder and concentrate
WO2019131759A1 (fr) * 2017-12-27 2019-07-04 サントリーホールディングス株式会社 Composition améliorant une fonction de barrière intestinale

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