KR20160058221A - A method for islating anthocyanin from black rice - Google Patents
A method for islating anthocyanin from black rice Download PDFInfo
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- 239000004410 anthocyanin Substances 0.000 title claims abstract description 32
- 235000010208 anthocyanin Nutrition 0.000 title claims abstract description 32
- 229930002877 anthocyanin Natural products 0.000 title claims abstract description 32
- 150000004636 anthocyanins Chemical class 0.000 title claims abstract description 32
- 241000371652 Curvularia clavata Species 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000605 extraction Methods 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000284 extract Substances 0.000 abstract description 18
- 235000011158 Prunus mume Nutrition 0.000 abstract 1
- 244000018795 Prunus mume Species 0.000 abstract 1
- 235000015096 spirit Nutrition 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004445 quantitative analysis Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 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 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol 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)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 235000013376 functional food Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- ZZWPMFROUHHAKY-OUUKCGNVSA-O peonidin 3-O-beta-D-glucoside Chemical compound C1=C(O)C(OC)=CC(C=2C(=CC=3C(O)=CC(O)=CC=3[O+]=2)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C1 ZZWPMFROUHHAKY-OUUKCGNVSA-O 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 244000178937 Brassica oleracea var. capitata Species 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 241000207836 Olea <angiosperm> Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002362 mulch Substances 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000009441 vascular protection Effects 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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- 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)
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- A61K36/899—Poaceae or Gramineae (Grass family), e.g. bamboo, corn or sugar cane
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
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- A23V2200/00—Function of food ingredients
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- A23V2200/308—Foods, ingredients or supplements having a functional effect on health having an effect on cancer prevention
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- A23V2200/00—Function of food ingredients
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- A23V2200/3262—Foods, ingredients or supplements having a functional effect on health having an effect on blood cholesterol
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- A23V2250/00—Food ingredients
- A23V2250/20—Natural extracts
- A23V2250/21—Plant extracts
- A23V2250/2104—Anthocyanins
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Abstract
Description
본 발명은 흑미로부터 안토시아닌 추출방법에 관한 것이다.The present invention relates to an anthocyanin extraction method from black rice.
식물성 천연색소인 안토시아닌은 최근 여러 가지 생리활성이 있는 것으로 알려지고 있다. 예를 들면 노화억제작용, 항균작용, 돌연변이성 억제작용, 콜레스테롤 저하작용, 시력개선 효과, 혈관보호기능, 항궤양기능, 항산화 기능 등이 알려져 있다. 이러한 생리활성은 모든 종류의 안토시아닌이 기본적으로 가지는 활성이지만, 최근 각 안토시아닌의 종류에 따라 그 활성의 차이가 있는 것으로 알려지고 있다.Anthocyanin, a natural coloring matter of plants, has recently been known to have various physiological activities. For example, antioxidant activity, antimicrobial activity, mutagenic activity, cholesterol lowering effect, vision improving effect, vascular protection function, anti-ulcer function and antioxidant function are known. These physiological activities are basically the activities of all kinds of anthocyanins, but recently, it has been known that there is a difference in activity depending on the type of anthocyanins.
안토시아닌 성분은 흔히 식물체의 꽃, 과실, 줄기, 잎, 뿌리 등에 함유되어 있는 물질로서, 현재 포도, 딸기,올리브, 적양배추, 가지, 장미 등의 식물체로부터 추출하여 여러 가지 원료로 이용되고 있으나, 거의 조색소 상태로 추출하여 이용되고 있는 실정이다. 따라서, 안토시아닌 외에 다른 성분의 화합물이 공존하는 상태로 이용되는 경우가 많다.The anthocyanin component is a substance contained in the flower, fruit, stem, leaf, and root of a plant, and is extracted from plants such as grapes, strawberries, olives, red cabbage, branches and roses and is used as various raw materials. And is extracted and used in the crude dye state. Therefore, in many cases, a compound of an ingredient other than anthocyanin coexists.
종전에는 안토시아닌 추출 효율을 높이기 위한 재료로 화학첨가물(구연산 등)을 첨가하는 기술이 있으나, 화학첨가물의 풍미가 강하게 느껴져 기능식품으로 개발하기에 어려운 단점이 있었다. In the past, there was a technique of adding a chemical additive (citric acid or the like) as a material for increasing anthocyanin extraction efficiency, but there was a disadvantage that it was difficult to develop a functional food because the flavor of a chemical additive felt strongly.
[선행 특허 문헌][Prior Patent Literature]
대한민국 공개특허번호 10-2007-0108979Korean Patent Publication No. 10-2007-0108979
본 발명은 상기의 문제점을 해결하고, 상기의 필요성에 의하여 안출된 것으로서 본 발명의 목적은 안토시아닌 추출효율성을 증대시키는 방법을 제공하는 것이다.Disclosure of Invention Technical Problem [8] Accordingly, the present invention has been made keeping in mind the above problems occurring in the prior art, and an object of the present invention is to provide a method for increasing anthocyanin extraction efficiency.
상기의 목적을 달성하기 위하여 본 발명은 흑미를 50% 에탄올과 건조매실 중량의 10 내지 20배수의 열수의 혼합 추출용매로 추출하는 단계를 포함하는 흑미로부터 안토시아닌을 추출하는 방법을 제공한다.In order to accomplish the above object, the present invention provides a method for extracting anthocyanins from black rice, comprising extracting black rice with 50 to 90% ethanol and 10 to 20 times as much water as the mixed water extraction solvent.
본 발명의 일 구현예에 있어서, 상기 추출용매는 50% 에탄올과 건조매실 중량의 10 배수의 열수 혼합물인 것이 바람직하나 이에 한정되지 아니한다.In one embodiment of the present invention, the extraction solvent is preferably a hydrothermal mixture of 50% ethanol and 10 times the weight of the dried plum, but is not limited thereto.
이하 본 발명을 설명한다. 본 발명은 흑미의 안토시아닌 추출 효율성을 증대시키기 위한 기술이며, 기능식품으로 개발하기에 적합한 천연추출물(매실추출물)을 용매로 사용하여 기능성물질인 안토시아닌 총량을 증대시키는 흑미의 안토시아닌 추출효율성 증대기술을 개발하였다.Hereinafter, the present invention will be described. The present invention is a technique for increasing anthocyanin extraction efficiency of black rice and development of anthocyanin extraction efficiency enhancement technology of black rice to increase the total amount of functional anthocyanin by using a natural extract (plum extract) suitable for developing functional food as a solvent Respectively.
본 발명을 통하여 알 수 있는 바와 같이, 본 발명의 매실추출물과 발효주정 혼합물을 추출용매로 흑미의 안토시아닌 추출효율성을 증대시키는 기술은 흑미로부터 안토시아닌 추출효율성을 높일 뿐만 아니라 풍미가 향상된 기능성식품(음료 등)으로 개발할 수 있는 장점이 있다.As can be seen from the present invention, the technique of increasing the extraction efficiency of anthocyanin from black rice using the extract of mulch extract and fermented alcohol of the present invention as an extraction solvent not only improves the extraction efficiency of anthocyanin from black rice, but also improves the flavor- ) Can be developed.
도 1은 50% 발효알콜 수용액으로 용매 추출한 흑미추출물의 안토시아닌 정량분석 (HPLC chromatogram)
도 2는 건조매실 중량의 20배 열수로 추출한 매실추출물과 발효알콜(95%이상)을 동량으로 혼합한 용매로 추출한 흑미추출물의 안토시아닌 정량분석 (HPLC chromatogram)
도 3은 건조매실 중량의 10배 열수로 추출한 매실추출물과 발효알콜(95%이상)을 동량으로 혼합한 용매로 추출한 흑미추출물의 안토시아닌 정량분석 (HPLC chromatogram) FIG. 1 shows an anthocyanin quantitative analysis (HPLC chromatogram) of a black rice extract obtained by solvent extraction with a 50% fermented alcohol aqueous solution.
FIG. 2 is a graph showing an anthocyanin quantitative analysis (HPLC chromatogram) of black rice extract obtained by extracting plum extract extracted with 20 times the weight of dried plum and fermented alcohol (95% or more)
FIG. 3 is a graph showing an anthocyanin quantitative analysis (HPLC chromatogram) of an extract of black rice extracted with the same amount of fermented alcohol (95% or more)
이하 비한정적인 실시예를 통하여 본 발명을 더욱 상세하게 설명한다.The present invention will now be described in more detail by way of non-limiting examples.
본 발명에서는 1)흑미 100그램을 50% 발효알콜 수용액 1,000그램으로 용매 추출한 후 안토시아닌 함량을 정량분석하고, In the present invention, 1) 100 g of black rice was subjected to solvent extraction with 1,000 g of 50% fermented alcohol aqueous solution, quantitatively analyzed anthocyanin content,
2)흑미 100그램을 50% 발효알콜수용액 500그램 + 건조 매실 25그램과 95℃ 열수 500그램(건조매실 중량의 20배)의 용매로 6시간 추출하여 상온으로 냉각시킨 매실추출물 500그램을 혼합한 용매 1,000그램으로 추출한 후 안토시아닌 함량을 정량분석하고, 2) 100 g of black rice was extracted with 500 g of 50% fermented alcohol aqueous solution + 25 g of dried plums and 500 g of 95 ° C hot water (20 times of dry plum weight) for 6 hours and mixed with 500 g of plum extract cooled to room temperature After extracting with 1,000 g of solvent, anthocyanin content was quantitatively analyzed,
3)은 상기 2)와 마찬가지 방법으로 흑미 100그램을 50%발효알콜수용액 500그램과 + 건조 매실 50그램과 95℃ 열수 500그램(건조매실 중량의 20배)의 용매로 6시간 추출하여 상온으로 냉각시킨 매실추출물 500그램을 혼합한 용매 1,00그램으로 추출한 후 안토시아닌 함량을 정량분석하여 그 결과를 표 1과 도면에 나타내었으며, 안토시아닌분석에 관한 그 세부 분석시험방법은 다음과 같다.3) was prepared in the same manner as in 2) above except that 100 g of black rice was extracted with 500 g of a fermented alcohol aqueous solution of 50%, 50 g of a dry plum, and 500 g of 95 ° C hot water (20 times the dry plum weight) 500 g of the cooled plum extract was extracted with 1.00 g of a solvent, and anthocyanin content was quantitatively analyzed. The results are shown in Table 1 and the drawings, and detailed analysis test methods for anthocyanin analysis are as follows.
흑미 추출물의 안토시아닌 분석에 활용된 용매는 모두 Merck Inc.(USA)의 HPLC 등급 시약을 구입하여 사용하였으며, 실험에 사용된 안토시아닌의 표준물질로서 C3G(Cyanidin 3-glucoside) 및 P3G(Peonidin 3-glucoside)는 화학적 구조가 동정된 분리 표준물질(시그마社 구입)을 사용하여 분석시료의 머무름 시간(Rt.) 및 흡광특성을 검정하였다.All of the solvents used for the analysis of anthocyanin of black rice extract were purchased from Merck Inc. (USA) HPLC grade reagent. Cyanidin 3-glucoside (C3G) and P3G (Peonidin 3-glucoside ) Was used to determine the retention time (Rt.) And absorbance characteristics of the analytical sample using a separation standard material (Sigma Co., Ltd.) whose chemical structure was identified.
상기 1)~3)방법으로 추출 후 Whatman No. 2 여과지로 1차 여과를 수행하였고, HPLC 분석 직전 syringe filter(0.45μm)로 2차 여과를 실시하고 HPLC분석에 사용하였다.After extracting with the above 1) to 3) method, 2 filter paper and subjected to secondary filtration with a syringe filter (0.45 μm) just before HPLC analysis and used for HPLC analysis.
흑미 함유 안토시아닌 분석에 사용된 HPLC는 Agillent 1200 series(USA)를 사용하였으며, 분석조건 중 유속은 분당 0.7 mL, 컬럼의 온도는 30℃, 시료 주입량을 20μL로 제한하여 사용하였다. 최적 HPLC 분석 조건 확립을 위해 사용된 분석 컬럼은 C18 및 C8 컬럼 12종을 사용하였고, HPLC 분석에 이용된 이동상 조건은 2상(two phase) 농도구배 조건으로 유기용매로는 5% 포믹산 함유 아세토니트릴을, 수용매는 5% 포믹산 함유 증류수를 사용하여 다양한 선형 농도 구배법으로 분리양상을 검토하였다.Agillent 1200 series (USA) was used for HPLC analysis of black anthocyanin-containing anthocyanin. The flow rate was 0.7 mL / min, column temperature was 30 ℃ and sample injection volume was 20 μL. The optimum analytical conditions for HPLC analysis were 12 kinds of C18 and C8 columns. The mobile phase conditions used for the HPLC analysis were two phase gradient conditions and 5% Nitrile, and distillation water containing 5% formic acid as the solvent were examined by various linear concentration gradient methods.
20배수추출물로 흑미추출50% alcohol + dry plum
Extract of black rice with 20
10배수추출물로 흑미추출50% alcohol + dry plum
Extract of black rice with 10 drainage extract
표 1은 매실혼합 발효알콜을 용매로 추출한 흑미추출물의 안토시아닌 정량분석 결과를 나타내며, 단위 : mg/g임.Table 1 shows the results of quantitative analysis of anthocyanins in black rice extracts obtained by extracting mulberry mixed fermented alcohol as a solvent. Unit: mg / g.
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