KR20060090019A - Oryzafuran, anti-oxident compound from oryza sativa l. and a method of seperation thereof - Google Patents
Oryzafuran, anti-oxident compound from oryza sativa l. and a method of seperation thereof Download PDFInfo
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- BVFAKXZUPQTNKN-UHFFFAOYSA-N oryzafuran Chemical compound O1C2=CC(O)=CC(O)=C2C(C(=O)OC)=C1C1=CC=C(O)C(O)=C1 BVFAKXZUPQTNKN-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 7
- 235000007164 Oryza sativa Nutrition 0.000 title claims description 9
- 240000007594 Oryza sativa Species 0.000 title claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 36
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 28
- 241000371652 Curvularia clavata Species 0.000 claims abstract description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002034 butanolic fraction Substances 0.000 claims description 5
- 239000000401 methanolic extract Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 2
- 238000002953 preparative HPLC Methods 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 235000006708 antioxidants Nutrition 0.000 abstract description 34
- 239000000126 substance Substances 0.000 abstract description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract description 8
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 abstract description 8
- 238000004611 spectroscopical analysis Methods 0.000 abstract description 8
- 230000002292 Radical scavenging effect Effects 0.000 abstract description 6
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 abstract description 3
- 229930003268 Vitamin C Natural products 0.000 abstract description 3
- 235000019154 vitamin C Nutrition 0.000 abstract description 3
- 239000011718 vitamin C Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 238000011835 investigation Methods 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 235000013305 food Nutrition 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 4
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- -1 anthocyanins Chemical class 0.000 description 2
- 229940076810 beta sitosterol Drugs 0.000 description 2
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 2
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- YTMNONATNXDQJF-UBNZBFALSA-N chrysanthemin Chemical compound [Cl-].O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC2=C(O)C=C(O)C=C2[O+]=C1C1=CC=C(O)C(O)=C1 YTMNONATNXDQJF-UBNZBFALSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 2
- 229950005143 sitosterol Drugs 0.000 description 2
- JHKIMSRSXHNYDC-UHFFFAOYSA-N COC(=O)C1=COC2=C1C(=CC(=C2)O)O Chemical compound COC(=O)C1=COC2=C1C(=CC(=C2)O)O JHKIMSRSXHNYDC-UHFFFAOYSA-N 0.000 description 1
- 230000005778 DNA damage Effects 0.000 description 1
- 231100000277 DNA damage Toxicity 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 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 description 1
- 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 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 235000010208 anthocyanin Nutrition 0.000 description 1
- 229930002877 anthocyanin Natural products 0.000 description 1
- 239000004410 anthocyanin Substances 0.000 description 1
- 150000004636 anthocyanins Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- ZFAJLYVPSZWPRP-UHFFFAOYSA-N butan-1-ol;hexane Chemical compound CCCCO.CCCCCC ZFAJLYVPSZWPRP-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
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- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03C—DOMESTIC PLUMBING INSTALLATIONS FOR FRESH WATER OR WASTE WATER; SINKS
- E03C1/00—Domestic plumbing installations for fresh water or waste water; Sinks
- E03C1/02—Plumbing installations for fresh water
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B1/00—Layered products having a non-planar shape
- B32B1/08—Tubular products
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
- B32B27/304—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising vinyl halide (co)polymers, e.g. PVC, PVDC, PVF, PVDF
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- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03C—DOMESTIC PLUMBING INSTALLATIONS FOR FRESH WATER OR WASTE WATER; SINKS
- E03C1/00—Domestic plumbing installations for fresh water or waste water; Sinks
- E03C1/12—Plumbing installations for waste water; Basins or fountains connected thereto; Sinks
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2597/00—Tubular articles, e.g. hoses, pipes
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Abstract
본 발명은 검정쌀 유래의 항산화화합물 오리자퓨란 및 이의 분리방법에 관한 것으로, 검정쌀로부터 항산화물질을 분리한 다음 상기 항산화물질의 물리화학적 특성과 분광학적 데이터를 조사하여 화학구조를 확인함으로써 상기 항산화물질이 신규의 화합물임을 확인하고 이를 오리자퓨란이라 명명한 뒤 상기 오리자퓨란의 DPPH 라디칼 제거 효과를 조사함으로써 항산화 능력이 비타민 C보다 우수한 신규의 항산화화합물 오리자퓨란을 제공하는 매우 뛰어난 효과가 있다.The present invention relates to an antioxidant compound oryzafuran derived from black rice and a method for separating the antioxidant, and the antioxidant is separated from the black rice, and then the physicochemical properties and spectroscopic data of the antioxidant are examined to confirm the chemical structure. By identifying the substance as a novel compound and naming it orizafuran, the investigation of DPPH radical scavenging effect of orizafuran has an excellent effect of providing a novel antioxidant compound orizafuran, which is superior to vitamin C. .
검정쌀, 흑진주벼, 항산화, 항산화화합물, DPPH 라디칼 제거Black Rice, Black Pearl Rice, Antioxidant, Antioxidant Compound, DPPH Radical Removal
Description
도 1은 본 발명의 신규 항산화화합물 오리자퓨란을 분리하는 과정을 도시하는 흐름도이다.1 is a flow chart illustrating a process for separating the novel antioxidant compound orizafuran of the present invention.
본 발명은 검정쌀 유래의 항산화화합물 오리자퓨란 및 이의 분리방법에 관한 것으로, 더욱 상세하게는 식품의 소재인 식물체 검정쌀의 메탄올 추출물로부터 분리한 항산화 능력이 비타민 C보다 우수한 항산화물질과 이의 분리방법에 관한 것이다.The present invention relates to an antioxidant compound oryzafuran derived from black rice and a method of separating the same, and more particularly, to an antioxidant having a superior antioxidant capacity from vitamin C of methanol extract of plant black rice, which is a food material, and an isolation method thereof. It is about.
일반적으로 생체내의 활성산소 라디칼은 DNA의 손상, 돌연변이, 암 및 노화 등에 관여하고 있다. 이런 상황하에 식품뿐 아니라 생체에 있어서 산화억제기능을 가지는 화합물이 크게 주목되고 있다. 식품의 저장이나 보존면에서 산화방지의 수단은 여러모로 시도되고 있지만 항산화제(산화방지제)의 이용이 일반적이다. 거의 모든 식품에 함유된 토코페롤은 천연항산화제로 널리 이용되고 있다. 1950년대부터 합성 항산화제인 BHA(butylated hydroxyaniso), BHT(butylated hydroxytoluene)가 개발되어 많은 나라에서 이용되어 왔지만 토코페롤은 효과면에서 조금 떨어지고 BHA, BHT는 효과는 뛰어나지만 발암, 폐와 간에 영향이 있음이 지적되어 안전성에 관해서 논란이 되었다. 이러한 이유에서 천연물에서 항산화제를 찾으려는 연구가 활발히 진행되고 있다.In general, free radicals in vivo are involved in DNA damage, mutations, cancer and aging. Under these circumstances, compounds having antioxidant functions not only in food but also in living bodies are attracting much attention. There have been many attempts to prevent antioxidants in food storage and preservation, but the use of antioxidants is common. Tocopherol, found in almost all foods, is widely used as a natural antioxidant. Since the 1950s, synthetic antioxidants such as butylated hydroxyaniso (BHA) and butylated hydroxytoluene (BHT) have been developed and used in many countries. It has been pointed out and controversial about safety. For this reason, studies are actively underway to find antioxidants in natural products.
쌀(Oryza sativa L., Poaceac)은 아시아인의 주식이며 세계 인구의 거의 절반에 해당하는 사람들에게 주요한 음식이다. 검정쌀은 한국, 일본 및 중국에서 오랫동안 소비되어왔으며 건강식품으로 알려져 있다.Rice ( Oryza sativa L., Poaceac) is a staple food of Asians and a major food for nearly half of the world's population. Black rice has long been consumed in Korea, Japan and China and is known as a health food.
검정쌀에서 지금까지 보고된 성분으로는 베타시토스테롤(β-sitosterol)을 비롯한 오리자놀, 시아니딘 3-글루코사이드(cyanidin 3 glucoside)를 포함한 안토시아닌, 바닐릭산 등의 단순페놀성 화합물 등이 있다.The ingredients reported in the black rice so far include simple phenolic compounds, such as anthocyanins, banil acid containing oryzanol, cyanidin 3-glucoside (cyanidin 3 glucoside), including beta-sitosterol (β -sitosterol).
본 발명은 검정쌀을 메탄올로 추출해서 얻은 메탄올 엑스를 헥산 부탄올 같은 유기용매를 사용해서 분획을 실시한 후 얻은 각각의 분획에 대하여 DPPH 제거능력을 평가하고 유의성 있는 저해활성을 보인 부탄올 분획을 정제하여 얻은 2-아릴벤조퓨란이 생물활성이 있는 지금까지 보고된 바 없는 새로운 화합물임을 알고 오리자퓨란(oryzafuran)으로 명명하고 이 화합물의 물리화학적 특성과 분광학적 데이터를 종합하여 그 화학구조를 규명함으로써 완성되었다.According to the present invention, the methanol extract obtained by extracting black rice with methanol was fractionated using an organic solvent such as hexane butanol. Knowing that 2-arylbenzofuran is a new compound that has never been reported to be bioactive, it was completed by naming it oryzafuran and combining its physicochemical and spectroscopic data to identify its chemical structure. .
따라서, 본 발명의 목적은 검정쌀 유래의 항산화화합물 오리자퓨란을 제공하는데 있다.Accordingly, it is an object of the present invention to provide an antioxidant compound orizafuran derived from black rice.
본 발명의 다른 목적은 검정쌀로부터 항산화화합물 오리자퓨란을 분리하는 방법을 제공하는데 있다.Another object of the present invention is to provide a method for separating the antioxidant compound orizafuran from black rice.
본 발명의 상기 목적은 검정쌀로부터 항산화물질을 분리한 다음 상기 항산화물질의 물리화학적 특성과 분광학적 데이터를 조사하여 화학구조를 확인함으로써 상기 항산화물질이 신규의 화합물임을 확인하고 이를 오리자퓨란이라 명명한 뒤 상기 오리자퓨란의 DPPH 라디칼 제거 효과를 조사함으로써 달성하였다.The object of the present invention is to isolate the antioxidant from black rice and then check the chemical structure by examining the physicochemical properties and spectroscopic data of the antioxidant to confirm that the antioxidant is a novel compound and named it orizafuran And by investigating the DPPH radical scavenging effect of oryzafuran.
본 발명은 검정쌀로부터 항산화물질을 분리하는 단계; 상기 단계의 검정쌀로부터 분리한 항산화물질의 물리화학적 특성과 분광학적 데이터를 조사하여 화학구조를 확인함으로써 상기 항산화물질이 신규의 화합물임을 확인하고 이를 오리자퓨란이라 명명하는 단계; 및 상기 오리자퓨란의 DPPH 라디칼 제거 효과를 조사하는 단계로 구성된다.The present invention comprises the steps of separating the antioxidant from the black rice; Confirming the chemical structure by examining the physicochemical properties and spectroscopic data of the antioxidants separated from the black rice of the step, identifying the antioxidants as novel compounds and naming them orizafuran; And investigating the DPPH radical scavenging effect of the orizafuran.
본 발명은 검정쌀(Oryza sativa L.)로부터 분리되고 하기 화학식 1의 구조를 가진 항산화활성 신규 화합물 오리자퓨란(oryzafuran)을 제공한다.The present invention provides an antioxidant active compound oryzafuran (Orizafuran), which is isolated from black rice ( Oryza sativa L.) and has the structure of Formula 1.
상기 오리자퓨란(oryzafuran)의 물리화학적 특성은 다음과 같다.The physical and chemical properties of oryzafuran are as follows.
1) 외관 : 옅은 갈색 결정1) Appearance: Light Brown Crystal
2) 융점 : 251 ~ 252 ℃2) Melting Point: 251 ~ 252 ℃
3) UV 흡수특성3) UV absorption characteristics
UV MeOH max nm (logε) : 250 (4.31), 340 (4.17)UV MeOH max nm (logε): 250 (4.31), 340 (4.17)
UV max (MeOH + NaOH) nm (logε) : 260 (4.40), 385 (4.22)UV max (MeOH + NaOH) nm (logε): 260 (4.40), 385 (4.22)
IR (KBr) max 3582, 3493, 3321, 1637, 1500 cm-1 IR (KBr) max 3582, 3493, 3321, 1637, 1500 cm -1
4) 1H-NMR (DMSO- d6, 500 MHz):4) 1 H-NMR (DMSO- d 6, 500 MHz):
7.16 (1H, d, J = 2.5 Hz, H-2')7.16 (1H, doublet, J = 2.5 Hz, H-2 ')
7.08 (1H, dd, J = 8.0, 2.5 Hz, H-6')7.08 (1H, doublet of doublets, J = 8.0, 2.5 Hz, H-6 ')
6.83 (1H, d, J = 8.0 Hz, H-5')6.83 (1H, doublet, J = 8.0 Hz, H-5 ')
6.46 (1H, d, J = 2.0 Hz, H-5)6.46 (1H, doublet, J = 2.0 Hz, H-5)
6.21 (1H, d, J = 2.0 Hz, H-7)6.21 (1H, doublet, J = 2.0 Hz, H-7)
3.82 (3H, s, COOCH 3)3.82 (3H, s, COO CH 3 )
5) 13C-NMR (DMSO-d6, 125 MHz):5) 13 C-NMR (DMSO- d 6, 125 MHz):
167.1 (COOCH3), 157.4 (C-2), 156.7 (C-8), 155.2 (C-6), 167.1 ( C OOCH 3 ), 157.4 (C-2), 156.7 (C-8), 155.2 (C-6),
151.0 (C-4), 147.4 (C-3'), 144.9 (C-4'), 120.5 (C-6'), 151.0 (C-4), 147.4 (C-3 '), 144.9 (C-4'), 120.5 (C-6 '),
120.1 (C-1'), 115.7 (C-2'), 115.4 (C-5'), 106.9 (C-9), 120.1 (C-1 '), 115.7 (C-2'), 115.4 (C-5 '), 106.9 (C-9),
106.3 (C-3), 98.7 (C-5), 89.2 (C-7), 52.6 (COOCH 3)106.3 (C-3), 98.7 (C-5), 89.2 (C-7), 52.6 (COO CH 3 )
6) EI-MS (70 eV) m/z (rel. int., %)6) EI-MS (70 eV) m / z (rel. Int.,%)
316 [M]+ (100), 285 [M-CH3O]+ (8.8), 284 [M-CH3OH]+(39.7), 316 [M] + (100), 285 [M-CH 3 O] + (8.8), 284 [M-CH 3 OH] + (39.7),
256 [M-CH3OH-CO]+ (47.9), 228 [M-CH3OH-2CO]+ (23.1), 256 [M-CH 3 OH-CO] + (47.9), 228 [M-CH 3 OH-2CO] + (23.1),
200 [M-CH3OH-2CO]+ (6.6), 171 (8.3), 149 (5.8)200 [M-CH 3 OH-2CO] + (6.6), 171 (8.3), 149 (5.8)
7) HR-EI-MS m/z 316.0594 [M]+ (calcd for [C16H12O7]+ : 316.0583) 7) HR-EI-MS m / z 316.0594 [M] + (calcd for [C 16 H 12 O 7 ] +: 316.0583)
본 발명의 오리자퓨란은 검정쌀(Oryza sativa L.)을 메탄올로 추출하여 얻은 메탄올추출물에 헥산을 넣어 혼합한 후 층분리가 일어나면 메탄올층만을 회수하여 메탄올을 휘발시킨 후 물과 부탄올을 넣어 부탄올 층만 회수한 다음 건조시킴으로써 부탄올 분획을 얻는 단계; 상기 부탄올 분획을 실리카겔크로마토그래피를 이용하고 CHCl3와 메탄올을 농도구배적으로 사용하여 분획하는 단계; 상기 단계에서 얻은 분획중 DPPH 제거능력이 있는 분획을 세파덱스 LH-20을 이용하고 물과 메탄올을 농도구배적으로 사용하여 추출하는 단계; 및 상기 단계에서 얻은 분획중 DPPH 제거능력이 있는 분획을 HPLC를 이용하고 25% 아세토나이트릴 수용액을 사용하여 분취하는 단계를 포함하는 분리방법을 통해 분리될 수 있다.Oryzafuran of the present invention is a black rice ( Oryza sativa L.) extracted with methanol, hexane is added to the methanol extract obtained by mixing and after separation of the methanol layer to recover only the methanol layer to volatilize water and butanol, butanol Recovering only the layer and then drying to obtain a butanol fraction; Fractionating the butanol fraction using silica gel chromatography and using CHCl 3 and methanol in concentration gradient; Extracting the fraction having DPPH removing ability from the fraction obtained in the above step using Sephadex LH-20 and using water and methanol in concentration gradient; And a fraction having a DPPH removal ability among the fractions obtained in the above step may be separated by a separation method using HPLC and separating using a 25% acetonitrile aqueous solution.
본 발명의 오리자퓨란은 검정쌀 품종이면 어느 품종에서든 분리될 수 있으나 본 발명에서는 흑진주벼(Heugjinjubyeo) 품종을 이용하여 분리 정제하고 DPPH 라디칼 제거 효과 조사 등을 수행하였다.Orijafuran of the present invention can be isolated from any variety if the black rice varieties, in the present invention was isolated and purified using the Black Jinju rice (Heugjinjubyeo) varieties, and investigated the effect of DPPH radical removal.
이하, 본 발명의 구성을 하기 실시예 및 실험예를 통하여 상세히 설명하지만 본 발명의 권리 범위가 하기 실시예 및 실험예에만 한정되는 것은 아니다.Hereinafter, the configuration of the present invention will be described in detail through the following examples and experimental examples, but the scope of the present invention is not limited only to the following examples and experimental examples.
실시예 1: 검정쌀로부터 항산화물질의 분리Example 1 Isolation of Antioxidants from Black Rice
흑진주벼(Heugjinjubyeo) 품종의 검정쌀 5kg을 메탄올로 추출해서 메탄올 엑스를 얻고 여기에 헥산을 넣어 혼합한 후 층 분리가 일어나면 헥산층을 버린 다음 남은 메탄올층의 메탄올을 휘발시키고 물을 넣었다. 상기 용액에 부탄올을 넣어 부탄올 층만을 회수한 다음 건조시킴으로써 유의성 있는 DPPH 저해활성을 보인 부탄올 분획 58g을 얻었다. 상기 부탄올 분획을 실리카겔(10×100, Merck, 7734)을 이용하고 CHCl3와 메탄올을 농도구배적(gradient)으로 사용하여 분획을 실시하였다. 그 결과 얻은 분획 중에서 DPPH 제거능력을 평가하고 가장 좋은 저해활성을 보인 326mg의 분획 16을 세파덱스 LH-20(5×100mm)을 이용하고 물과 메탄올을 농도구배 적(gradient)으로 사용하여 추출하였다. 상기 추출 결과 얻은 분획 중에서 가장 뛰어난 DPPH 제거능력을 가진 128mg의 분획 3을 HPLC(C18, 10×250mm)를 이용하고 25% 아세토나이트릴 수용액을 사용하여 분취함으로써 옅은 갈색 결정 24mg을 얻었다.After extracting 5kg of black rice of Heugjinjubyeo varieties with methanol to obtain methanol-X, mixed with hexane, and then separating the layers, the hexane layer was discarded and the methanol of the remaining methanol layer was volatilized and water was added. Butanol was added to the solution to recover only butanol layer and dried to obtain 58 g of butanol fraction showing significant DPPH inhibitory activity. The butanol fraction was fractionated using silica gel (10 × 100, Merck, 7734) and CHCl 3 and methanol as gradients. From the resulting fractions, DPPH removal ability was evaluated, and 326 mg of fraction 16, which showed the best inhibitory activity, was extracted using Sephadex LH-20 (5 × 100 mm) and water and methanol in gradient. . Among the fractions obtained from the extraction, 128 mg of fraction 3 having the best DPPH removal ability was fractionated using HPLC (C18, 10 × 250 mm) and 25% acetonitrile aqueous solution to obtain 24 mg of light brown crystals.
실험예 1: 검정쌀로부터 분리한 항산화물질의 물리화학적 특성과 분광학적 데이터 조사 및 이를 통한 화학구조의 확인Experimental Example 1 Examination of Physicochemical and Spectroscopic Data of Antioxidants Isolated from Black Rice and Identification of Chemical Structure
상기 실시예 1에서 얻은 옅은 갈색 결정의 물리화학적 특성과 분광학적 데이터를 조사하고 이를 종합하여 그 화학구조를 규명한 결과 하기 화학식 1의 구조를 가진 2-(3,4-디하이드록시페닐)-4,6-디하이드록시-벤조후란-3-카르복실릭산 메틸에스터였다. 상기 2-아릴벤조퓨란계 화합물은 지금까지 보고된 바 없는 새로운 화합물임을 확인하였고 이를 오리자퓨란(oryzafuran)으로 명명하였다. 본 발명 항산화물질 오리자퓨란의 물리화학적 특성과 분광학적 데이터는 다음과 같았다.The physicochemical and spectroscopic data of the pale brown crystals obtained in Example 1 were investigated and their chemical structures were synthesized. As a result, 2- (3,4-dihydroxyphenyl)-having the structure of Formula 1 4,6-dihydroxy-benzofuran-3-carboxylic acid methyl ester. The 2-arylbenzofuran compound was identified as a new compound that has not been reported so far, and was named oryzafuran. The physicochemical and spectroscopic data of the antioxidant urizafuran of the present invention were as follows.
[화학식 1][Formula 1]
1) 외관 : 옅은 갈색 결정1) Appearance: Light Brown Crystal
2) 융점 : 251 ~ 252 ℃2) Melting Point: 251 ~ 252 ℃
3) UV 흡수특성3) UV absorption characteristics
UV MeOH max nm (logε) : 250 (4.31), 340 (4.17)UV MeOH max nm (logε): 250 (4.31), 340 (4.17)
UV max (MeOH + NaOH) nm (logε) : 260 (4.40), 385 (4.22)UV max (MeOH + NaOH) nm (logε): 260 (4.40), 385 (4.22)
IR (KBr) max 3582, 3493, 3321, 1637, 1500 cm-1 IR (KBr) max 3582, 3493, 3321, 1637, 1500 cm -1
4) 1H-NMR (DMSO- d6, 500 MHz):4) 1 H-NMR (DMSO- d 6, 500 MHz):
7.16 (1H, d, J = 2.5 Hz, H-2')7.16 (1H, doublet, J = 2.5 Hz, H-2 ')
7.08 (1H, dd, J = 8.0, 2.5 Hz, H-6')7.08 (1H, doublet of doublets, J = 8.0, 2.5 Hz, H-6 ')
6.83 (1H, d, J = 8.0 Hz, H-5')6.83 (1H, doublet, J = 8.0 Hz, H-5 ')
6.46 (1H, d, J = 2.0 Hz, H-5)6.46 (1H, doublet, J = 2.0 Hz, H-5)
6.21 (1H, d, J = 2.0 Hz, H-7)6.21 (1H, doublet, J = 2.0 Hz, H-7)
3.82 (3H, s, COOCH 3)3.82 (3H, s, COO CH 3 )
5) 13C-NMR (DMSO-d6, 125 MHz):5) 13 C-NMR (DMSO- d 6, 125 MHz):
167.1 (COOCH3), 157.4 (C-2), 156.7 (C-8), 155.2 (C-6), 167.1 ( C OOCH 3 ), 157.4 (C-2), 156.7 (C-8), 155.2 (C-6),
151.0 (C-4), 147.4 (C-3'), 144.9 (C-4'), 120.5 (C-6'), 151.0 (C-4), 147.4 (C-3 '), 144.9 (C-4'), 120.5 (C-6 '),
120.1 (C-1'), 115.7 (C-2'), 115.4 (C-5'), 106.9 (C-9), 120.1 (C-1 '), 115.7 (C-2'), 115.4 (C-5 '), 106.9 (C-9),
106.3 (C-3), 98.7 (C-5), 89.2 (C-7), 52.6 (COOCH 3)106.3 (C-3), 98.7 (C-5), 89.2 (C-7), 52.6 (COO CH 3 )
6) EI-MS (70 eV) m/z (rel. int., %)6) EI-MS (70 eV) m / z (rel. Int.,%)
316 [M]+ (100), 285 [M-CH3O]+ (8.8), 284 [M-CH3OH]+(39.7), 316 [M] + (100), 285 [M-CH 3 O] + (8.8), 284 [M-CH 3 OH] + (39.7),
256 [M-CH3OH-CO]+ (47.9), 228 [M-CH3OH-2CO]+ (23.1), 256 [M-CH 3 OH-CO] + (47.9), 228 [M-CH 3 OH-2CO] + (23.1),
200 [M-CH3OH-2CO]+ (6.6), 171 (8.3), 149 (5.8)200 [M-CH 3 OH-2CO] + (6.6), 171 (8.3), 149 (5.8)
7) HR-EI-MS m/z 316.0594 [M]+ (calcd for [C16H12O7]+ : 316.0583) 7) HR-EI-MS m / z 316.0594 [M] + (calcd for [C 16 H 12 O 7 ] +: 316.0583)
실험예 2: 오리자퓨란의 DPPH 라디칼 제거 효과Experimental Example 2: DPPH radical scavenging effect of orizafuran
실시예 1에서 분리하고 실시예 2에서 구조식을 규명한 오리자퓨란의 DPPH 라디칼 제거 효과를 조사하였다. 그 결과는 하기 표 1에 나타내었다.The DPPH radical scavenging effect of oryzafuran isolated in Example 1 and the structural formula was identified in Example 2 was investigated. The results are shown in Table 1 below.
상기에서 설명한 바와 같이 본 발명은 검정쌀 유래의 항산화화합물 오리자퓨란 및 이의 분리방법에 관한 것으로, 검정쌀로부터 항산화물질을 분리한 다음 상기 항산화물질의 물리화학적 특성과 분광학적 데이터를 조사하여 화학구조를 확인함으로써 상기 항산화물질이 신규의 화합물임을 확인하고 이를 오리자퓨란이라 명명한 뒤 상기 오리자퓨란의 DPPH 라디칼 제거 효과를 조사함으로써 항산화 능력이 비타민 C보다 우수한 신규의 항산화화합물 오리자퓨란을 제공하는 매우 뛰어난 효과가 있으므로 식·의약품산업상 매우 유용한 발명인 것이다.As described above, the present invention relates to an antioxidant compound oryzafuran derived from black rice and a method of separating the same, and the chemical structure of the antioxidant is separated from the black rice, and the physicochemical properties and spectroscopic data of the antioxidant are investigated. By confirming that the antioxidant is a novel compound and named it orizafuran and investigate the DPPH radical scavenging effect of the orizafuran to provide a novel antioxidant compound orizafuran superior to vitamin C It is a very useful invention in the food and pharmaceutical industry because it is very effective.
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