WO2012004875A1 - Nouvelle substance séparée d'une orchidée, et extrait, antioxydant, agent antibactérien, agent anti-cancer et agent anti-inflammatoire la contenant - Google Patents

Nouvelle substance séparée d'une orchidée, et extrait, antioxydant, agent antibactérien, agent anti-cancer et agent anti-inflammatoire la contenant Download PDF

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Publication number
WO2012004875A1
WO2012004875A1 PCT/JP2010/061608 JP2010061608W WO2012004875A1 WO 2012004875 A1 WO2012004875 A1 WO 2012004875A1 JP 2010061608 W JP2010061608 W JP 2010061608W WO 2012004875 A1 WO2012004875 A1 WO 2012004875A1
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compound
agent
extract
novel substance
formula
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PCT/JP2010/061608
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English (en)
Japanese (ja)
Inventor
吉川和子
橋本敏弘
馬場千裕
今川洋
森田博史
井関賀奈子
河野幸子
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株式会社河野メリクロン
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Priority to JP2010545712A priority Critical patent/JP5567499B2/ja
Priority to PCT/JP2010/061608 priority patent/WO2012004875A1/fr
Publication of WO2012004875A1 publication Critical patent/WO2012004875A1/fr

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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)
    • A61K36/898—Orchidaceae (Orchid family)
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
    • C07C50/34—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having three rings

Definitions

  • the present invention relates to a novel substance isolated from an orchidaceae plant, an extract containing the same, an antioxidant, an antibacterial agent, an anticancer agent and an anti-inflammatory agent.
  • Active oxygen such as singlet oxygen, hydrogen peroxide, superoxide anion, and hydroxyl radical is oxygen that is susceptible to chemical reaction, and exhibits a very strong oxidizing power compared to normal oxygen. Active oxygen is generated in daily life. For example, oxygen taken from the air by breathing is generated by alteration in the body. Reactive oxygen has important effects on the body, such as promoting enzyme reactions in the body and sterilizing with powerful force to prevent diseases.
  • antioxidants that suppress the oxidation reaction of excess active oxygen.
  • antioxidants for synthetic compounds butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), and the like are known, but such synthetic compounds are not preferred because they are carcinogenic.
  • vitamin E fat-soluble tocopherol
  • vitamin C water-soluble ascorbic acid
  • an object of the present invention is to provide an antioxidant having an effective antioxidant action without causing side effects.
  • an orchidaceae extract contains a novel phenanthrene compound represented by the following formula (1).
  • the present inventors have obtained knowledge that they have a good antioxidant action and are less likely to cause side effects, and have completed the present invention. Furthermore, this novel compound was also found to be excellent in antibacterial action, anticancer action and anti-inflammatory action. .
  • the present invention can be provided as an antioxidant, antibacterial agent, anticancer agent or anti-inflammatory agent containing a novel substance represented by the formula (1).
  • the present invention provides a pharmaceutical composition, quasi-drug composition, cosmetic composition containing the novel substance represented by formula (1) for the purpose of antioxidant action, antibacterial action, anticancer action or anti-inflammatory action. Products and food additives.
  • the novel substance shown by Formula (1) of this invention has a red pigment
  • novel substance represented by the above formula (1) of the present invention is contained in an orchidaceae extract and can be produced by isolation from the extract. Good.
  • orchidaceae examples include, but are not limited to, Cymbidium plants, Cattleya plants, Dendrobium plants, Phalaenopsis plants, Miltonia plants, Vanilla plants, Ebine plants, Nervana plants, Toxos plants, etc.
  • Cymbidium plants are particularly preferable because they contain many new substances represented by the formula (1).
  • the Cymbidium genus plant is a monocotyledon of the orchidaceae that grows mainly from the temperate zone of Asia to the tropics. Cymbidium plants have been improved, and there are many plants registered under the seedling method. Representative species including native species are Chunlan (cym.goeringii), Shangran (cym.kanran), Hausairan, (cym.sinense) Sulgaran (cym.ensifolium), Goldfish (cym.pumilum), Great Flower Marie Laurent Sun (Cym. Great Flower 'Marylaurencin'), Rose Wine ⁇ New Century (Cym Rose Wine'Shinseiki ') Great Flower Ballerina (Cym.
  • Orchidaceae extracts may be extracted from any part of the orchidaceae plant as an extraction raw material. Orchidaceae roots, stems, leaves, flowers, seeds, pseudococcus or whole plants may be used as they are or in an appropriate size. Although it can be used after being cut or crushed, the root extract contains a large amount of the compound of formula (1), and it has an anti-oxidant action, an anti-bacterial action, an anti-cancer action, and an anti-inflammatory action. Since it is excellent, it is preferable.
  • Preparation of orchidaceae extracts can be done by physical extraction method, solvent extraction method, vacuum distillation, or squeezing a part or whole plant of orchidaceae plant as it is or after cutting to a suitable size or pulverizing with a pulverizer. Any of the extraction methods can be employed. Examples of the extraction solvent include hydrophilic solvents such as water, methanol, ethanol, isopropanol, propylene glycol, 1,3-butylene glycol, glycerin, and acetone, and two or more of these may be used in combination. Moreover, the extract to be adjusted may be liquid or solid.
  • a part or whole plant of orchidaceae is cut as it is or cut to an appropriate size or pulverized with a pulverizer, soaked in methanol or an aqueous ethanol solution, and stirred occasionally.
  • an extraction operation is performed, impurities are removed by filtration, and an orchidaceae plant extract is produced by distillation under reduced pressure under reduced pressure.
  • 100 ml of purified water is added to 5 g of the pulverized product obtained in the same manner as described above, followed by heating and extraction in a boiling water bath for about 2 hours, and then an equal amount of 95% ethanol is added and left still. Then, if impurities are removed with filter paper, an orchidaceae plant extract can be produced.
  • This orchidaceae plant extract can be dried, concentrated or diluted, mixed with other ingredients, etc., depending on the application form, and contains antioxidants, antibacterial agents, anticancer agents, anti-inflammatory agents, pharmaceuticals It may be a composition, a quasi-drug composition, a cosmetic composition, or a food additive, or a novel substance represented by the formula (1) is isolated and an antioxidant or antibacterial containing this novel substance as an active ingredient It may be an agent, an anticancer agent, an anti-inflammatory agent, a pharmaceutical composition, a quasi-drug composition, a cosmetic composition, or a food additive.
  • the method for isolating the novel substance represented by the formula (1) can be obtained by further separating and purifying means, preferably thin layer chromatography, column chromatography, high performance liquid chromatography, or It is performed by repeatedly performing recrystallization and the like.
  • the novel substance represented by the formula (1) is a naturally-derived component that is highly safe and has an antioxidant action, antibacterial action, anticancer action, and anti-inflammatory action. Therefore, it can be used as a pharmaceutical composition, quasi-drug composition, cosmetic composition or food additive containing this novel substance as an active ingredient.
  • Block diagram showing extraction process of compounds 1-5 Figure showing the crystal structure of Compound 1 by X-ray crystallography
  • the graph which shows the nitric oxide production suppression rate of the compound 1 The graph which shows the nitric oxide production suppression rate of the compound 4
  • novel substance represented by the following formula (1) of the present invention can be isolated from an extract obtained by extracting an orchidaceae plant with a solvent by a commonly used separation and purification means.
  • the novel substance represented by the above formula (1) has an antioxidant action, an antibacterial action, an anticancer action or an anti-inflammatory action. Therefore, the novel substance represented by the formula (1) can be used as an active ingredient of an antioxidant, an antibacterial agent, an anticancer agent or an anti-inflammatory agent regardless of whether it is oral or parenteral.
  • the novel substance represented by the formula (1) can be blended as it is for the purpose of obtaining any or all of the above-mentioned effects and can be used as a medicine, quasi-drug, cosmetic, food, or Various pharmaceuticals and quasi drugs, such as powders, granules, tablets, capsules or liquid materials, diluted with an appropriate medium or by methods known in the field of manufacturing pharmaceuticals, quasi drugs, cosmetics and foods Can be used in cosmetic, food form.
  • a pharmaceutical product or quasi-drug it can be widely used for ordinary pharmaceutical products or quasi-drugs, and is a liquid for internal use, tablets, ointments, troches, liver oil drops, mouth fresheners, Mouth fragrances, mouthwashes, haps, magnesium supplements, mineral fortifiers, various drinks, external preparations for skin, hair growth agents, hair restorers, hair nourishing agents, medicated soaps, medicated toothpastes and the like can be mentioned.
  • lotion for cosmetics, lotion, whitening agent, serum, milky lotion, cream, hair tonic, hair cream, shampoo, rinse, treatment, body soap, facial cleanser, soap, toothpaste, bath preparation, aromatic product, lipstick, lip balm, White powder, eye shadow, hair color and the like can be mentioned.
  • a moisturizer As long as the novel substance represented by the formula (1) is within the range not impairing the effects of the present invention, a moisturizer, surfactant, pigment, fragrance, enzyme, hormones, vitamins, UV absorber, UV shielding Agent, solvent, stabilizer, plasticizer, lubricant, solubilizer, reducing agent, buffer, sweetener, base, volatilization aid, adsorbent, flavoring agent, synergist, binder, suspending agent Antioxidants, brighteners, coating agents, wetting agents, cooling agents, softeners, emulsifiers, excipients, preservatives, preservatives and the like can be added and used according to ordinary methods.
  • the extract of the orchidaceae is purified to isolate a plurality of compounds.
  • the extract was extracted with a mixed solution of 9 L of ethyl acetate and 9 L of water, and fractionated into an ethyl acetate soluble part and a water soluble part.
  • the solvent was distilled off under reduced pressure to obtain ethyl acetate-soluble part powder (42 g) and water-soluble part powder (130 g).
  • the obtained ethyl acetate soluble part powder was subjected to silica gel column chromatography, and eluted with a mixed solution of hexane-ethyl acetate (10: 1). Fractions (fractions 1-8) were obtained.
  • Fraction 3 was subjected to silica gel column chromatography using an elution solvent of hexane-ethyl acetate (7: 3) to obtain five fractions (fractions 3-1 to 3-5).
  • Fraction 3-3 was purified with 60% aqueous methanol by high performance liquid chromatography (ODS) to obtain Compound 2 (390 mg) and Compound 5 (117 mg).
  • ODS high performance liquid chromatography
  • fraction 4 was subjected to silica gel column chromatography using an elution solvent of hexane-ethyl acetate (6: 4) to obtain six fractions (fractions 4-1 to 4-6). Of these, fraction 4-2 was recrystallized to obtain Compound 1 (80 mg).
  • Fraction 4-3 was purified by high performance liquid chromatography (ODS) with 60% aqueous methanol to obtain compound 3 (80 mg) and compound 4 (70 mg).
  • the compound 1 has a chemical structure represented by the above formula (1)
  • the compound 2 is represented by the following formula (2). It has been shown that Compound 1 and Compound 2 are novel phenanthrene compounds.
  • Compound 3 has the chemical structure represented by the following formula (3)
  • compound 4 has the following formula (4)
  • compound 5 has the chemical structure represented by the following formula (5), and was found to be a known phenanthrene compound.
  • the final sample concentrations were 100 ⁇ g / mL, 30 ⁇ g / mL, 10 ⁇ g. / ML, 3 ⁇ g / mL, and 1 ⁇ g / mL, for a total of 5 doses.
  • the final sample concentrations were 10 ⁇ g / mL, 3 ⁇ g / mL, 1 ⁇ g / mL, 0.3 ⁇ g / mL, and 0.1 ⁇ g / mL, and the total concentration was 5 doses.
  • SOD activity value (% inhibition) (1 ⁇ (Sample ⁇ BLK2) / (BLK1 ⁇ BLK3)) ⁇ 100 (6)
  • Sample Absorbance at the time of compound addition / enzyme solution addition
  • BLK1 Absorbance when no compound is added and enzyme solution is added
  • BLK2 Absorbance when compound is added and enzyme solution is not added
  • BLK3 Absorbance when no compound is added and no enzyme solution is added.
  • ⁇ Test Example 2 Antibacterial action> Compounds 1, 3 to 5 obtained in the above examples were tested for antibacterial activity by serial dilution method in an antibacterial liquid medium. That is, a series of compound solutions diluted in stages and a certain amount of the test bacterial solution are added to the nutrient medium and cultured for a certain period of time. When the fungus grows, the liquid becomes cloudy and the color of the added pigment changes. Thus, the liquid dilution method is a method for measuring the minimum concentration (MIC) of a compound in which no bacterial growth is observed.
  • MIC minimum concentration
  • a sample prepared by adjusting each of the above compounds 1 to 5 to a DMSO solution of 0.01 g / mL (1 w / v%) is added to the nutrient medium (1 ⁇ L of the test bacteria solution to 99 ⁇ L of the nutrient medium) to which the test bacteria solution is added.
  • the sample concentration starts at a maximum concentration of 100 ⁇ g / L on the medium, serially dilutes, and is performed at a total of 6 doses of 50 ⁇ g / mL, 25 ⁇ g / mL, 12.5 ⁇ g / mL, 6.25 ⁇ g / mL, and 3.125 ⁇ g / mL. did.
  • Bacillus subtilis and Candida albicans were used as the test bacterial solution.
  • Bacillus subtilis: YP medium was used as the nutrient medium, and ampicillin was used as the positive control.
  • the culture was stationary culture at 37 ° C. for 24 hours.
  • Candida albicans: Sabouraud medium was used as a nutrient medium, and cycloheximide was used as a positive control.
  • the culture was stationary culture at 27 ° C. for 24 hours.
  • Tumor cells used for the test were purchased from Dainippon Pharmaceutical Co., Ltd., HL60 (blood premyelocytic leukemia), MCF7 (breast adenocarcinoma), HCT116 (colon cancer), NC I-H226 (Non-small cell lung carcinoma) and A549 (Lung carcinoma Human lung adenocarcinoma epithelial cell line) were used.
  • Each tumor cell was cultured in RPMI-1640 medium (manufactured by Sigma Aldrich Japan) containing 10% fetal bovine serum (FBS) and penicillin / streptomycin in a 37 ° C., 5% CO 2 incubator, and the number of cells was adjusted. Used for experiments.
  • Compound 1 showed a cell growth inhibitory effect on each tumor cell.
  • Compound 1 has been shown to be highly sensitive to NCI-H226 (non-small cell lung cancer). This indicates that Compound 1 is effective as an anticancer agent.
  • Mouse macrophage-like cell J774.1 cells were provided by RIKEN BRC. Cells were cultured in RPMI-1640 medium (Sigma Aldrich Japan) containing 10% fetal bovine serum (FBS) and penicillin / streptomycin in a 37 ° C, 5% CO 2 incubator, and the number of cells was adjusted for use in experiments. It was.
  • a 96-well plate was inoculated with 100 ⁇ L of a cell suspension of 1 ⁇ 10 5 cells / well, and statically cultured at 37 ° C. in a 5% CO 2 incubator for 12 hours. Next, the cultured cells were washed with a phosphate buffer, and then the cells were statically cultured for 24 hours in a medium containing LPS 5 ⁇ g / mL adjusted to each concentration by adding compounds 1, 2 and 5, respectively.
  • the compound 1 it implemented by the total 5 dose of 50 microgram / mL, 25 microgram / mL, 12.5 microgram / mL, 6.3 microgram / mL, and 3.1 microgram / mL.
  • compound 4 and 5 it implemented by the total 4 dose of 50 microgram / mL, 25 microgram / mL, 12.5 microgram / mL, and 6.3 microgram / mL.
  • Nitric oxide production ability was measured by the Griess assay method. 100 ⁇ L of each supernatant cultured for 24 hours was transferred to a 96-well plate, and 100 ⁇ L of Griess reagent (1% sulfanilamide, 0.1% N-1-naphthylethylenediamine dihydrochloride in 2.5% H 3 PO 4 ) was added thereto. After incubation at room temperature for 15 minutes, absorbance was measured at test wavelengths of 540 nm and 620 nm (Benchmark Plus microplate spectrometer, manufactured by Bio-Rad Laboratories).
  • B Absorbance in the case of LPS (+) and compound (+)
  • C Absorbance in the case of LPS ( ⁇ ) and compound ( ⁇ ) (AC: NO 2 - shows the correspondence) to the concentration ([mu] M).
  • the cells attached to the microplate were confirmed by the MTT assay to be free from cell damage and induction, and the cell viability was measured as shown in FIGS. This is shown in the graph.
  • compounds 1, 4 and 5 that can suppress the production of nitric oxide are plant components that can be expected to be applied to humans. is there. For example, it is effective for treatment and prevention of diseases requiring suppression of nitric oxide production by application to functional foods and suppression of excessive NO expression due to various factors. Therefore, compounds 1, 4 and 5, especially compound 1, can be expected to be used as active ingredients of nitric oxide production inhibitors and anti-inflammatory agents.
  • the novel substance represented by the formula (1) of the present invention is a naturally derived component and has high safety and has an antioxidant action, an antibacterial action, an anticancer action, and an anti-inflammatory action, the novel substance is effective. It can be used as a pharmaceutical composition, quasi-drug composition, cosmetic composition or food additive formulated as an ingredient.

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Abstract

L'invention a pour objectif de proposer un antioxydant qui a un effet antioxydant efficace sans effets secondaires. L'invention concerne une nouvelle substance représentée par la formule (1).
PCT/JP2010/061608 2010-07-08 2010-07-08 Nouvelle substance séparée d'une orchidée, et extrait, antioxydant, agent antibactérien, agent anti-cancer et agent anti-inflammatoire la contenant WO2012004875A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2010545712A JP5567499B2 (ja) 2010-07-08 2010-07-08 ラン科植物から分離した新規物質、これを含む抽出物、抗酸化剤、抗菌剤、抗癌剤及び抗炎症剤
PCT/JP2010/061608 WO2012004875A1 (fr) 2010-07-08 2010-07-08 Nouvelle substance séparée d'une orchidée, et extrait, antioxydant, agent antibactérien, agent anti-cancer et agent anti-inflammatoire la contenant

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PCT/JP2010/061608 WO2012004875A1 (fr) 2010-07-08 2010-07-08 Nouvelle substance séparée d'une orchidée, et extrait, antioxydant, agent antibactérien, agent anti-cancer et agent anti-inflammatoire la contenant

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WO2012004875A1 true WO2012004875A1 (fr) 2012-01-12

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
CN103432206A (zh) * 2013-09-06 2013-12-11 太仓市荣德生物技术研究所 一种天然植物抑菌杀菌制剂
CN110652488A (zh) * 2018-06-29 2020-01-07 伽蓝（集团）股份有限公司 虎头兰提取物的应用

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WO2000027224A1 (fr) * 1998-11-11 2000-05-18 Manabu Nomura Produits alimentaires favorables a la sante
JP2002003336A (ja) * 2000-06-19 2002-01-09 Naris Cosmetics Co Ltd 化粧料
JP2002114646A (ja) * 2000-10-02 2002-04-16 Kawano Merikuron:Kk 発毛・育毛剤
JP2002205933A (ja) * 2001-01-05 2002-07-23 Ichimaru Pharcos Co Ltd ラン科植物抽出物含有化粧料組成物

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WO2000027224A1 (fr) * 1998-11-11 2000-05-18 Manabu Nomura Produits alimentaires favorables a la sante
JP2002003336A (ja) * 2000-06-19 2002-01-09 Naris Cosmetics Co Ltd 化粧料
JP2002114646A (ja) * 2000-10-02 2002-04-16 Kawano Merikuron:Kk 発毛・育毛剤
JP2002205933A (ja) * 2001-01-05 2002-07-23 Ichimaru Pharcos Co Ltd ラン科植物抽出物含有化粧料組成物

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Title
JUNEJA, R.K. ET AL.: "Two substituted bibenzyls and a dihydrophenanthrene from Cymbidium aloifolium.", PHYTOCHEMISTRY, vol. 26, no. 4, 1987, pages 1123 - 1125 *
KAZUKO YOSHIKAWA ET AL., ABSTRACTS OF ANNUAL MEETING OF PHARMACEUTICAL SOCIETY OF JAPAN, vol. 129TH, no. 2, 2009, pages 171 *
KAZUKO YOSHIKAWA ET AL., ABSTRACTS OF ANNUAL MEETING OF PHARMACEUTICAL SOCIETY OF JAPAN, vol. 130, no. 2, 5 March 2010 (2010-03-05), pages 174 *
YANG, M.H. ET AL.: "Three new phenanthrenes from Monomeria barbata Lindl", vol. 21, no. 3, March 2010 (2010-03-01), pages 325 - 328 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103432206A (zh) * 2013-09-06 2013-12-11 太仓市荣德生物技术研究所 一种天然植物抑菌杀菌制剂
CN110652488A (zh) * 2018-06-29 2020-01-07 伽蓝（集团）股份有限公司 虎头兰提取物的应用

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