JP2909522B2 - UV protection - Google Patents
UV protectionInfo
- Publication number
- JP2909522B2 JP2909522B2 JP23738392A JP23738392A JP2909522B2 JP 2909522 B2 JP2909522 B2 JP 2909522B2 JP 23738392 A JP23738392 A JP 23738392A JP 23738392 A JP23738392 A JP 23738392A JP 2909522 B2 JP2909522 B2 JP 2909522B2
- Authority
- JP
- Japan
- Prior art keywords
- quercetin
- ultraviolet
- cells
- effect
- diglucoside
- 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.)
- Expired - Lifetime
Links
- 230000006750 UV protection Effects 0.000 title description 10
- REFJWTPEDVJJIY-UHFFFAOYSA-N quercetin Natural products C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 12
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims description 10
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims description 10
- 229930182470 glycoside Natural products 0.000 claims description 10
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 10
- 239000003223 protective agent Substances 0.000 claims description 10
- 235000005875 quercetin Nutrition 0.000 claims description 10
- 229960001285 quercetin Drugs 0.000 claims description 10
- -1 quercetin glycoside Chemical class 0.000 claims description 9
- RPVIQWDFJPYNJM-UHFFFAOYSA-N Ganodermic acid Ja Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)OC2C(C(O)C(O)C(CO)O2)O)C=C1O RPVIQWDFJPYNJM-UHFFFAOYSA-N 0.000 claims description 8
- RPVIQWDFJPYNJM-MPPJEPTCSA-N Quercetin 3,4'-di-O-beta-D-glucopyranoside Natural products O([C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1)c1c(O)cc(C2=C(O[C@H]3[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O3)C(=O)c3c(O)cc(O)cc3O2)cc1 RPVIQWDFJPYNJM-MPPJEPTCSA-N 0.000 claims description 8
- RPVIQWDFJPYNJM-DEFKTLOSSA-N quercetin 3,4'-di-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1O RPVIQWDFJPYNJM-DEFKTLOSSA-N 0.000 claims description 8
- ORKTXZHKYFWCRB-UHFFFAOYSA-N methyl 3-amino-5-chlorobenzoate Chemical compound COC(=O)C1=CC(N)=CC(Cl)=C1 ORKTXZHKYFWCRB-UHFFFAOYSA-N 0.000 claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 235000013305 food Nutrition 0.000 description 8
- 239000002537 cosmetic Substances 0.000 description 7
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 6
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 6
- 201000006845 reticulosarcoma Diseases 0.000 description 6
- 208000029922 reticulum cell sarcoma Diseases 0.000 description 6
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 6
- 229960004555 rutoside Drugs 0.000 description 6
- 210000004748 cultured cell Anatomy 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000003556 assay Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000001665 lethal effect Effects 0.000 description 4
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- VVXVTYYCCQZUKK-UHFFFAOYSA-N quercetin 3-rutinoside Natural products CC1OC(OCC2OC(OC3=C(Oc4ccc(O)c(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C(O)C2O)C(O)C(O)C1O VVXVTYYCCQZUKK-UHFFFAOYSA-N 0.000 description 4
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 229930003935 flavonoid Natural products 0.000 description 3
- 235000017173 flavonoids Nutrition 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 244000291564 Allium cepa Species 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OVSQVDMCBVZWGM-IDRAQACASA-N Hirsutrin Natural products O([C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1)C1=C(c2cc(O)c(O)cc2)Oc2c(c(O)cc(O)c2)C1=O OVSQVDMCBVZWGM-IDRAQACASA-N 0.000 description 2
- FVQOMEDMFUMIMO-UHFFFAOYSA-N Hyperosid Natural products OC1C(O)C(O)C(CO)OC1OC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 FVQOMEDMFUMIMO-UHFFFAOYSA-N 0.000 description 2
- 238000000134 MTT assay Methods 0.000 description 2
- 231100000002 MTT assay Toxicity 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- GXMWXESSGGEWEM-UHFFFAOYSA-N isoquercitrin Natural products OCC(O)C1OC(OC2C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)C(O)C1O GXMWXESSGGEWEM-UHFFFAOYSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 2
- 235000005493 rutin Nutrition 0.000 description 2
- 230000035899 viability Effects 0.000 description 2
- YNMFDPCLPIMRFD-KSPKLRDJSA-N 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)CO[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 YNMFDPCLPIMRFD-KSPKLRDJSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 206010065559 Cerebral arteriosclerosis Diseases 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 208000035859 Drug effect increased Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- BDCDNTVZSILEOY-BQCJVYABSA-N Quercetin 3-arabinoside Chemical compound O[C@@H]1[C@@H](O)[C@H](CO)O[C@@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O BDCDNTVZSILEOY-BQCJVYABSA-N 0.000 description 1
- NSZQOXBBEWYGQH-UHFFFAOYSA-N Quercetin-3-rhamnosid Natural products CC1OC(O)C(O)C(OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)C1O NSZQOXBBEWYGQH-UHFFFAOYSA-N 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 102000004338 Transferrin Human genes 0.000 description 1
- 108090000901 Transferrin Proteins 0.000 description 1
- YNMFDPCLPIMRFD-UHFFFAOYSA-N UNPD14535 Natural products OC1C(O)C(O)COC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 YNMFDPCLPIMRFD-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000022534 cell killing Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000018927 edible plant Nutrition 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- ALRFYJWUVHBXLV-UHFFFAOYSA-N guaijaverin Natural products OC1COC(COC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)C(O)C1O ALRFYJWUVHBXLV-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 201000005851 intracranial arteriosclerosis Diseases 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 210000001700 mitochondrial membrane Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 208000007578 phototoxic dermatitis Diseases 0.000 description 1
- 231100000018 phototoxicity Toxicity 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HDDDNIUXSFCGMB-UHFFFAOYSA-N quercetin 3-galactoside Natural products OCC1OC(OC2=C(Oc3ccc(O)c(O)c3C2=O)c4ccc(O)c(O)c4)C(O)C(O)C1O HDDDNIUXSFCGMB-UHFFFAOYSA-N 0.000 description 1
- OXGUCUVFOIWWQJ-HQBVPOQASA-N quercitrin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OXGUCUVFOIWWQJ-HQBVPOQASA-N 0.000 description 1
- 230000035806 respiratory chain Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000012581 transferrin Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【０００１】[0001]
本発明は、植物由来のケルセチン(quercetin) の配糖体
を有効成分とする紫外線防御剤に関する。The present invention relates to an ultraviolet ray protective agent comprising a plant-derived quercetin glycoside as an active ingredient.
【０００２】[0002]
紫外線は、物質に光化学反応を誘起する力が強く、物質
の劣化、変質の原因となる。従って、例えば食品におい
ては、含有脂質の酸化、色素の退色、更には栄養成分の
分解などが起こり、品質劣化の重要な一因となる。ま
た、生物に対しても大きな影響を及ぼすが、特にＤＮＡ
は感受性が高く、紫外線照射により生成したラジカル分
子が細胞に傷害を与え、突然変異等を引き起こす。結果
として生体に重大な傷害を与えることになるが、特に近
年、大気中のオゾンの減少による地上の紫外線量の増加
により、皮膚ガンの増加が懸念されている。Ultraviolet light has a strong power to induce a photochemical reaction in a substance, and causes deterioration and deterioration of the substance. Therefore, for example, in foods, oxidation of contained lipids, fading of pigments, and decomposition of nutrients occur, which is an important factor in quality deterioration. It also has a great effect on living organisms, especially DNA
Is highly sensitive, and radical molecules generated by ultraviolet irradiation damage cells, causing mutations and the like. As a result, the living body is seriously injured. However, in recent years, there is a concern that skin cancer may increase due to an increase in the amount of ultraviolet rays on the ground due to a decrease in atmospheric ozone.
【０００３】 このような状況にあって、より有効な紫外線防御剤が望
まれているが、現在化粧品等に使われている紫外線吸収
剤には、光毒性や累積刺激性があるなど、安全性の面と
物性の面での問題がある。また、食品に使用可能で十分
効果的な紫外線防御物質も見あたらない。 一方、ケルセチンは、次式：[0003] Under such circumstances, more effective ultraviolet ray protective agents have been desired. However, ultraviolet ray absorbents currently used in cosmetics and the like have safety, such as phototoxicity and cumulative irritation. There are problems in terms of properties and physical properties. In addition, there is no effective UV protection substance that can be used in foods. On the other hand, quercetin has the following formula:
【０００４】[0004]
【化１】 Embedded image
【０００５】 で示される公知のフラボノイドであり、その配糖体の一
種であるルチン（ケルセチン−３−ルチノシド）はソ
バ、タバコ、エンジュなどから得られ、毛細血管の脆弱
化を防止し、毛細血管を強化する作用を有することか
ら、脳溢血、動脈硬化、高血圧症の治療、予防に用いら
れている。 しかしながら、ケルセチン又はその配糖体の紫外線防御
作用については知られていない。[0005] Rutin (quercetin-3-rutinoside), which is a known flavonoid represented by and is a kind of glycoside, is obtained from buckwheat, tobacco, endju, etc., and prevents capillary blood vessels from weakening, It is used for the treatment and prevention of cerebral hemorrhage, arteriosclerosis, and hypertension. However, it is not known about the ultraviolet protection effect of quercetin or its glycoside.
【０００６】[0006]
以上の事情に鑑み、本発明者等は、化粧品に有効でしか
も食品加工の分野にも使用できる安全で効果的な紫外線
防御物質を得るべく、最近これら物質の探索源として注
目されている植物体、特に食用として生産されている野
菜を対象に鋭意スクリーニングを行った。その結果、一
般的な植物色素のフラボノイドに属する化合物の一部が
紫外線防御作用を示すことを認め本発明を完成した。In view of the above circumstances, the present inventors have developed a plant that has recently attracted attention as a search source for these substances in order to obtain safe and effective ultraviolet protection substances that are effective for cosmetics and can also be used in the field of food processing. In particular, intensive screening was performed on vegetables produced for food use. As a result, it was recognized that some of the compounds belonging to the flavonoids of general plant pigments exhibited an ultraviolet protection effect, and thus completed the present invention.
【０００７】[0007]
本発明の紫外線防御剤は、ケルセチンの配糖体を有効成
分として含有するものである。 本発明の紫外線防御剤において、有効成分として用いる
ケルセチンの配糖体としては、例えばケルセチン−３，
４’−ジグルコシド、ケルセチン−３−アラビノグルコ
シド（ペルタトシド(peltatoside))、ケルセチン−３−
ルチノシド（ルチン(rutin))、ケルセチン−３−グルコ
シド（イソケルシトリン（isoquercitrin））、ケルセ
チン−３−Ｌ−ラムノシド（ケルシトリン(quercitri
n)）、ケルセチン−３−アラビノシド（アビクラリン(a
vicularin)）が挙げられるが、特にケルセチン−３，
４’−ジグルコシド、ケルセチン−３−アラビノグルコ
シド、ケルセチン−３−ルチノシドが好ましい。The ultraviolet protective agent of the present invention contains a quercetin glycoside as an active ingredient. The quercetin glycoside used as an active ingredient in the ultraviolet protective agent of the present invention includes, for example, quercetin-3,
4'-diglucoside, quercetin-3-arabinoglucoside (peltatoside), quercetin-3-
Rutinoside (rutin), quercetin-3-glucoside (isoquercitrin), quercetin-3-L-rhamnoside (quercitri
n)), quercetin-3-arabinoside (aviclarin (a
vicularin)), especially quercetin-3,
4'-diglucoside, quercetin-3-arabinoglucoside, quercetin-3-rutinoside are preferred.
【０００８】 紫外線防御効果の判定法として種々の物理化学的方法が
用いられるが、培養細胞、特にヒト細胞を用いる方法
が、紫外線の生体に対する有害作用の阻止効果を評価す
る方法として最も適していると考えられる。種々検討の
結果、ヒト由来培養細胞を、各種検体を添加した培養液
中で紫外線照射下に培養し、細胞のバイアビリティーを
ＭＴＴアッセイ法（培養細胞III 、4477−4482(1984)）
で測定する生物検定法を確立した。[0008] Various physicochemical methods are used as a method for determining the ultraviolet protection effect, and a method using cultured cells, particularly human cells, is the most suitable method for evaluating the effect of inhibiting the harmful effects of ultraviolet light on living organisms. it is conceivable that. As a result of various studies, human-derived cultured cells were cultured in a culture solution to which various specimens were added under ultraviolet irradiation, and the viability of the cells was measured by the MTT assay method (Cultured Cell III, 4477-4482 (1984)).
A bioassay method was established for measurement in.
【０００９】 ヒト培養細胞は、組織球性リンパ腫細胞、Ｕ−937 を用
い、培養用の培地は５％ウシ胎児血清及びインシュリ
ン、トランスフェリン、エタノールアミン等の成長促進
因子を加えたＥＲＤＦ培地（日本水産科学、55(4)、 525
-527(1987)）を使用した。この培地に試験用サンプルと
共に細胞を８×105／mlの濃度で撒き、主波長254nm の
紫外線を300uW／cm2の強度で照射した。照射時間は５分
間とし、照射後４時間、37℃で培養を継続した。培養終
了後、ＭＴＴアッセイに供した。[0009] Human cultured cells are histiocytic lymphoma cells, U-937, and the culture medium is an ERDF medium (Nippon Suisan) supplemented with 5% fetal calf serum and growth promoting factors such as insulin, transferrin, and ethanolamine. Science, 55 (4), 525
-527 (1987)). The cells were spread on this medium together with the test sample at a concentration of 8 × 10 5 / ml, and irradiated with ultraviolet light having a main wavelength of 254 nm at an intensity of 300 uW / cm 2 . The irradiation time was 5 minutes, and the culture was continued at 37 ° C. for 4 hours after irradiation. After completion of the culture, the cells were subjected to an MTT assay.
【００１０】 ＭＴＴ［臭化３−（４，５−ジメチルチアゾリル）−
２，５−ジフェニル−２Ｈテトラゾリウム］は、細胞の
ミトコンドリア内膜中に存在する呼吸鎖に関与する酵素
により開裂、ＭＴＴフォルマザンへ変換される。このフ
ォルマザンの生成量は細胞の活性と密接に関連してお
り、ほぼ比例関係にある。また、フォルマザンは着色し
ているので、その強度を比色定量することにより細胞の
活性、即ち生細胞数や増殖能を判定できる。これが、Ｍ
ＴＴアッセイ法の原理である。MTT [3- (4,5-dimethylthiazolyl bromide)-
2,5-diphenyl-2H tetrazolium] is cleaved by an enzyme involved in the respiratory chain present in the inner mitochondrial membrane of cells and converted to MTT formazan. The amount of formazan produced is closely related to the activity of the cells, and is approximately proportional. In addition, since formazan is colored, the activity of the cells, that is, the number of living cells and the proliferation ability can be determined by colorimetrically measuring the intensity. This is M
This is the principle of the TT assay.
【００１１】 上記培養液にＭＴＴ試薬（５mg／mlリン酸緩衝液（0.14
M NaCl含有))を加え、更に37℃で４時間培養した。培養
終了後、1,000 ×ｇで５分遠心分離し、沈殿したフォル
マザンの結晶を得た。これをジメチルスルホキシドに溶
解し、540 nmの吸光度をマイクロプレートリーダーで測
定した。 タマネギ等の各種食用植物から80％メタノールで抽出し
たフラボノイド化合物を、オクタデシル基等を支持体に
結合した逆相カラムを用いた高速液体クロマトグラフィ
ー、あるいはアンバーライトＣＧ50等のイオン交換クロ
マトグラフィー等で分画し、種々のケルセチン配糖体を
得た。得られた各種化合物を種々の濃度で細胞培養液に
加え、上記方法で紫外線の細胞致死作用の抑制効果につ
いて検討した。同時に、当該化合物の細胞に対する致死
作用についても調べた。[0011] In the above culture solution, an MTT reagent (5 mg / ml phosphate buffer (0.14
M NaCl-containing)), and the cells were further cultured at 37 ° C. for 4 hours. After completion of the culture, the mixture was centrifuged at 1,000 × g for 5 minutes to obtain precipitated formazan crystals. This was dissolved in dimethyl sulfoxide, and the absorbance at 540 nm was measured with a microplate reader. Flavonoid compounds extracted from various edible plants such as onions with 80% methanol are separated by high-performance liquid chromatography using a reversed-phase column having an octadecyl group or the like bonded to a support, or ion-exchange chromatography such as Amberlite CG50. To obtain various quercetin glycosides. The obtained various compounds were added at various concentrations to the cell culture solution, and the effect of suppressing the cell killing action of ultraviolet rays was examined by the above method. At the same time, the lethal effect of the compound on cells was also examined.
【００１２】 各種ケルセチン配糖体の中で、３，４’−ジグルコシド
及び３−アラビノグルコシドや３−ルチノシドでほぼ10
0 ％の防御効果が認められ、また、致死作用は殆ど認め
られず、食品用及び化粧品用の紫外線防御剤として極め
て優れていることが判明した。 本発明の紫外線防御剤は、食品中の脂質の酸化や色素の
退色の防止を目的に、食品に混合することが可能であ
る。また、化粧品に配合し日焼け止め化粧料を作ること
が可能である。Among various quercetin glycosides, 3,4′-diglucoside, 3-arabinoglucoside and 3-rutinoside have almost 10
A protective effect of 0% was observed, and almost no lethal effect was observed, indicating that it was extremely excellent as an ultraviolet protective agent for foods and cosmetics. The ultraviolet protective agent of the present invention can be mixed with foods for the purpose of preventing lipid oxidation in foods and fading of pigments. In addition, it can be blended with cosmetics to make sunscreen cosmetics.
【００１３】 ケルセチン配糖体の紫外線防御剤としての使用量は、添
加する対象商品により異なるが、例えば食品に対しては
500〜800マイクロモル／食品kg、化粧品に対しては400
〜600 マイクロモル／化粧品kgが好ましい。[0013] The amount of quercetin glycoside used as an ultraviolet ray protective agent varies depending on the target product to be added.
500-800 micromol / kg of food, 400 for cosmetics
~ 600 micromol / kg cosmetic is preferred.
【００１４】[0014]
以下、実施例により本発明を更に具体的に説明するが、
本発明の範囲はこれらの実施例に限定されるものではな
い。 （実施例１） （１）ケルセチン−３，４’−ジグルコシドの調製 タマネギを皮ごと等量の80％メタノール中でホモジナイ
ズした後、濾紙により吸引濾過した。濾液を減圧濃縮し
て得た抽出物を脱イオン水に溶解し、脱イオン水で平衡
化した逆相系のアンバーライトＸＡＤ−２カラムに通し
た。試料液と等量の脱イオン水でカラムを洗浄後、メタ
ノールで溶出した。メタノール溶出画分を減圧濃縮乾固
させた。この画分を少量の50％メタノールに溶解し、50
％メタノールで平衡化したトヨパールＨＷ−40でゲル濾
過を行った。その一画分にケルセチン−３，４’−ジグ
ルコシドをほぼ純度100 ％の状態で得た。このようにし
て得られたケルセチン−３，４’−ジグルコシドは、塩
化アルミニウムや酢酸ナトリウムの添加に伴う吸収スペ
クトルの変化やマスフラグメント分析において、公知の
ものと一致した。 （２）紫外線防御効果の検定 次いで、ケルセチン−３，４’−ジグルコシドを種々の
濃度で培養液に添加し、ヒト組織球性リンパ腫細胞、Ｕ
-937を用いたアッセイ系で紫外線防御効果を調べた。濃
度と共に防御効果は上昇し、400 マイクロモル／リット
ル程度でほぼ100 ％の効果が得られた。一方、致死効果
は800 マイクロモル／リットルの濃度においても全く認
められなかった（図１）。Hereinafter, the present invention will be described more specifically with reference to Examples.
The scope of the present invention is not limited to these examples. (Example 1) (1) Preparation of quercetin-3,4'-diglucoside Onion was homogenized together with the skin in an equal volume of 80% methanol, and then suction-filtered with a filter paper. The extract obtained by concentrating the filtrate under reduced pressure was dissolved in deionized water, and passed through a reverse-phase Amberlite XAD-2 column equilibrated with deionized water. The column was washed with the same amount of deionized water as the sample solution, and then eluted with methanol. The fraction eluted with methanol was concentrated to dryness under reduced pressure. This fraction is dissolved in a small amount of 50% methanol,
Gel filtration was performed with Toyopearl HW-40 equilibrated with% methanol. Quercetin-3,4'-diglucoside was obtained in one fraction at a purity of almost 100%. Quercetin-3,4'-diglucoside thus obtained was consistent with known ones in the change in absorption spectrum and mass fragment analysis accompanying the addition of aluminum chloride and sodium acetate. (2) Assay for UV protection effect Next, quercetin-3,4'-diglucoside was added to the culture at various concentrations, and human histiocytic lymphoma cells, U
The UV protection effect was examined in an assay system using -937. The protective effect increased with the concentration, and almost 100% of the effect was obtained at about 400 micromol / liter. On the other hand, no lethal effect was observed even at a concentration of 800 micromol / liter (FIG. 1).
【００１５】 （実施例２） ケルセチン−３−アラビノグルコシドとケルセチン−３
−ルチノシドを種々の濃度で培養液に添加し、ヒト組織
球性リンパ腫細胞、Ｕ−937 を用いたアッセイの系で効
果を調べた。ＭＴＴ法で調べた培養細胞のバイアビリテ
ィーはいずれの化合物においても添加濃度の増加と共に
急激に上昇し、400 マイクロモル／リットルで100 ％に
達し、紫外線の有害作用を完全に防御した。一方、致死
効果はいずれも、800 マイクロモル／リットルの濃度に
おいても全く認められなかった（図２、図３）。Example 2 Quercetin-3-arabinoglucoside and quercetin-3
-Rutinosides were added to the culture at various concentrations, and the effect was examined in an assay system using human histiocytic lymphoma cells, U-937. The viability of the cultured cells examined by the MTT method increased sharply with increasing concentrations of all the compounds, and reached 100% at 400 micromol / liter, completely preventing the harmful effects of ultraviolet rays. On the other hand, none of the lethal effects were observed even at a concentration of 800 micromol / liter (FIGS. 2 and 3).
【００１６】[0016]
本発明により、優れた紫外線防御作用を示し、しかも極
めて安全性の高い紫外線防御剤が提供される。According to the present invention, there is provided an ultraviolet protective agent which exhibits excellent ultraviolet protective action and is extremely safe.
【図１】ケルセチン−３，４’−ジグルコシドのヒト組
織球性リンパ腫細胞系における紫外線防御効果を示す図
である。FIG. 1 shows the protective effect of quercetin-3,4′-diglucoside on ultraviolet rays in human histiocytic lymphoma cell lines.
【図２】ケルセチン−３−アラビノグルコシドのヒト組
織球性リンパ腫細胞系における紫外線防御効果を示す図
である。FIG. 2 shows the UV protection effect of quercetin-3-arabinoglucoside on human histiocytic lymphoma cell lines.
【図３】ケルセチン−３−ルチノシドのヒト組織球性リ
ンパ腫細胞系における紫外線防御効果を示す図である。FIG. 3 shows the UV protection effect of quercetin-3-rutinoside on human histiocytic lymphoma cell lines.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) C09K 3/00 104 A61K 7/42 A61K 31/35 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ) ＢＥＩＬＳＴＥＩＮ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. 6 , DB name) C09K 3/00 104 A61K 7/42 A61K 31/35 CA (STN) REGISTRY (STN) BEILSTEIN (STN)
Claims (3)
びケルセチン−３−アラビノグルコシドから選ばれるケ
ルセチンの配糖体を有効成分として含有する紫外線防御
剤。(1) Quercetin-3,4'-diglucoside and
And a quercetin-3- arabinoglucoside.
４’−ジグルコシドである請求項１の紫外線防御剤。2. The quercetin glycoside is quercetin-3,
The ultraviolet protective agent according to claim 1, which is 4'-diglucoside.
アラビノグルコシドである請求項１の紫外線防御剤。3. The quercetin glycoside is quercetin-3-
The ultraviolet protective agent according to claim 1, which is arabinoglucoside.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23738392A JP2909522B2 (en) | 1992-09-04 | 1992-09-04 | UV protection |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23738392A JP2909522B2 (en) | 1992-09-04 | 1992-09-04 | UV protection |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0688063A JPH0688063A (en) | 1994-03-29 |
| JP2909522B2 true JP2909522B2 (en) | 1999-06-23 |
Family
ID=17014578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23738392A Expired - Lifetime JP2909522B2 (en) | 1992-09-04 | 1992-09-04 | UV protection |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2909522B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103641865A (en) * | 2013-12-19 | 2014-03-19 | 青岛农业大学 | Method for extracting onion oligosaccharides and extract thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2820738B1 (en) * | 2001-02-15 | 2003-05-16 | Agronomique Inst Nat Rech | PROCESS FOR THE EXTRACTION, FRACTIONATION AND PURIFICATION OF POLYPHENOLIC COMPOUNDS FROM SORTING GAPS OF FRESH PLANTS USING A HIGH-YIELD ADSORPTION AND ELUTING RESIN |
| JP4901024B2 (en) * | 2001-06-22 | 2012-03-21 | 株式会社ナリス化粧品 | 8-OHdG (8-hydroxydeoxyguanosine) production inhibitor |
| AU2002359931A1 (en) * | 2001-12-28 | 2003-07-24 | Sansho Seiyaku Co., Ltd. | Compositions containing pigmentatin inhibitor, use thereof and process for producing the same |
| KR101069907B1 (en) * | 2008-09-04 | 2011-10-05 | 재단법인 제주테크노파크 | A composition for skin whitening comprising extract, fraction or compound from Lindera erythrocarpa |
| JP2016013075A (en) * | 2014-07-01 | 2016-01-28 | イビデン株式会社 | Quercetin-containing extract |
-
1992
- 1992-09-04 JP JP23738392A patent/JP2909522B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103641865A (en) * | 2013-12-19 | 2014-03-19 | 青岛农业大学 | Method for extracting onion oligosaccharides and extract thereof |
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| Publication number | Publication date |
|---|---|
| JPH0688063A (en) | 1994-03-29 |
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