KR100361632B1 - Extracting process of highly purified natural rutin from buckwheat - Google Patents
Extracting process of highly purified natural rutin from buckwheat Download PDFInfo
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- KR100361632B1 KR100361632B1 KR1020000048918A KR20000048918A KR100361632B1 KR 100361632 B1 KR100361632 B1 KR 100361632B1 KR 1020000048918 A KR1020000048918 A KR 1020000048918A KR 20000048918 A KR20000048918 A KR 20000048918A KR 100361632 B1 KR100361632 B1 KR 100361632B1
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- 241000219051 Fagopyrum Species 0.000 title claims abstract description 39
- 235000009419 Fagopyrum esculentum Nutrition 0.000 title claims abstract description 39
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- IKGXIBQEEMLURG-NVPNHPEKSA-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-NVPNHPEKSA-N 0.000 description 34
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- C—CHEMISTRY; METALLURGY
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- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
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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
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- A61K36/70—Polygonaceae (Buckwheat family), e.g. spineflower or dock
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- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
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Abstract
본 발명은 메밀로부터 고순도 천연 루틴의 추출방법에 관한 것으로서, 더욱 상세하게는 한국산 재래종 메밀 전초의 건조물을 50% 아세톤 수용액 또는 50% 에탄올 수용액으로 가열환류하여 루틴을 추출하고, 다공성 흡착수지 및 재결정을 통해 정제함으로써, 고혈압, 뇌혈과 질환 등에 예방 및 치료효과가 있는 생리활성 물질인 루틴(Rutin)을 순도 95% 이상으로 얻을 수 있는 메밀로부터 고순도 천연 루틴을 추출하는 방법에 관한 것이다.The present invention relates to a method of extracting high-purity natural rutin from buckwheat, and more particularly, by heating and refluxing a dried product of Korean native buckwheat starch with a 50% acetone aqueous solution or a 50% ethanol aqueous solution, and extracting the porous adsorbent resin and recrystallization. The present invention relates to a method of extracting high-purity natural rutin from buckwheat, which can obtain rutin, a bioactive substance having a prophylactic and therapeutic effect on hypertension, cerebral blood and diseases, with a purity of 95% or more.
Description
본 발명은 메밀로부터 고순도 천연 루틴의 추출방법에 관한 것으로서, 더욱 상세하게는 한국산 재래종 메밀 전초의 건조물을 50% 아세톤 수용액 또는 50% 에탄올 수용액으로 가열환류하여 루틴을 추출하고, 다공성 흡착수지 및 재결정을 통해 정제함으로써, 고혈압, 뇌혈과 질환 등에 예방 및 치료효과가 있는 생리활성 물질인 루틴(Rutin)을 순도 95% 이상으로 얻을 수 있는 메밀로부터 고순도 천연 루틴을 추출하는 방법에 관한 것이다.The present invention relates to a method of extracting high-purity natural rutin from buckwheat, and more particularly, by heating and refluxing a dried product of Korean native buckwheat starch with a 50% acetone aqueous solution or a 50% ethanol aqueous solution, and extracting the porous adsorbent resin and recrystallization. The present invention relates to a method of extracting high-purity natural rutin from buckwheat, which can obtain rutin, a bioactive substance having a prophylactic and therapeutic effect on hypertension, cerebral blood and diseases, with a purity of 95% or more.
최근 우리 나라는 경제성장에 따라 생활환경의 개선, 풍요한 식생활과 의료제도, 각종 편의시설의 혜택 등으로 말미암아 평균수명이 급격히 증가하고 있으나, 한편으로는 영양의 과다섭취 등이 원인인 것으로 추정되는 암, 고혈압, 뇌졸증, 당뇨병, 동맥경화 등의 만성 성인 질환이 크게 증가하고 있는 추세이다. 그 중에서도 고혈압 및 뇌혈관 질환은 심각한 사회 문제로 대두되고 있으므로, 이들 질환에 대한 예방의 중요성이 크게 강조되고 있다.Recently, the average life expectancy of our country is rapidly increasing due to the improvement of the living environment, the abundant diet, the medical system, and the convenience of the various facilities due to the economic growth. Chronic adult diseases such as cancer, hypertension, stroke, diabetes, and arteriosclerosis are increasing. Among them, hypertension and cerebrovascular disease have emerged as serious social problems, and the importance of prevention of these diseases has been greatly emphasized.
한편, 우리 나라의 전통식품 중 메밀국수나 메밀묵은 민간요법으로 고혈압 등에 예방 및 치료의 효과가 있는 것으로 알려져 있는데, 이는 메밀에 소량 함유되어 있는 다음 화학식 1로 표시되는 루틴이라는 생리활성 물질에 의한 것임이 밝혀졌다.On the other hand, buckwheat noodles and buckwheat jelly are known to have the effect of preventing and treating hypertension due to folk remedies, which are due to the bioactive substance called rutin represented by the following formula (1) Turned out.
상기 화학식 1로 표시되는 루틴은 일명 비타민 P로도 알려져 있는데, 비타민 P는 혈관의 저항성을 강하게 하여 뇌출혈을 예방하는 중요한 성분으로 보고되어 있다["식품학", 심상국·양종범 공저, 고문사, 1992]. 그 뿐 아니라, 혈관계 질환의 치료제로서 혈관의 지나친 투과성을 억제하는 약리효과도 가지고 있음이 공지되어 있다[영국 특허 제2,111,385호; Tetsuo Murakami et al.,Agri. Biol. Chem.,49, (4), 909∼914, 1985]. 또한, 비타민 P가 비타민 C의 생리적인 기능인 체내 결합조직의 주성분인 콜라겐의 합성에 필요한 프롤린 및 리신의 히드록실화 반응, Fe2＋를 Fe3＋로 전환 시켜주는 시토크롬 C의 산화-환원 반응, 혈액 중 백혈구의 증가에 따른 면역강화 기능 등에도 크게 관여하고 있다는 것은 공지된 사실이다.The routine represented by Formula 1 is also known as vitamin P, which is reported to be an important component for preventing hemorrhage by strengthening blood vessel resistance ("Food Science", co-author Shim Sang-jong and Yang Jong-bum, Advisor, 1992). In addition, it is known to have a pharmacological effect of inhibiting excessive permeability of blood vessels as a therapeutic agent for vascular diseases [UK Patent No. 2,111,385; Tetsuo Murakami et al.,Agri. Biol. Chem.,49, (4), 909-914, 1985]. In addition, the hydroxylation of proline and lysine required for the synthesis of collagen, the main component of connective tissue in the body, which vitamin P is the physiological function of vitamin C, Fe2+To Fe3+in It is well known that he / she is greatly involved in the oxidation-reduction reaction of cytochrome C, which is converted, and the immune-enhancing function of leukocytes in the blood.
오늘날 루틴의 용도는 영양소로서 비타민 P의 강화에만 국한되고 있는 것이 아니라, 그 화학구조와 생리활성 기능으로 인하여 용도의 범위가 점차 확장되고 있다. 특히 음식물 질환이나 순환기 질환과 같은 감수성 질환의 예방 및 치료를 위한 의약품으로 널리 이용될 뿐만 아니라, 안정성이 높은 천연 황색 색소, 산화 방지제, 안정제, 퇴색 방지제, 품질 개선제, 보존제, 예방제, UV 흡수제, 열화(劣化) 방지제 등으로서 식품, 기호품, 사료, 애완동물 식품, 피부 청정제 또는 피부 백화제 등의 화장품 및 플라스틱 분야에 널리 이용되고 있다.The use of rutin today is not limited to the strengthening of vitamin P as a nutrient, but its scope of use is gradually expanded due to its chemical structure and bioactive function. In particular, it is widely used as a medicine for the prevention and treatment of susceptible diseases such as food and circulatory diseases, as well as highly stable natural yellow pigments, antioxidants, stabilizers, fading agents, quality improvers, preservatives, preventive agents, UV absorbers, deterioration It is widely used in cosmetics and plastics fields such as foods, foods, pet foods, pet foods, skin cleansers or skin whitening agents.
한편, 종래 메밀을 이용한 루틴 제조에 관련된 연구는 메밀 중에 루틴의 함량이 소량인 점을 감안하여 발아를 통한 루틴의 함량이 증가된 메밀 추출액을 제조하는 방법[대한민국특허 제0154582호, 1998], 루틴의 함량이 증가된 메밀 발효액을 제조하는 방법[대한민국특허 제115448호, 1997] 등이 보고되어 있다. 그밖에, 난용성 루틴의 실용성 가치를 높인 효소처리 알파-글리코실 루틴 제조[일본특허 공보 제32,073/79호] 등에 대한 연구가 있을 뿐 메밀로부터 순도 95 % 이상의 고순도천연 루틴을 추출하는 방법에 대한 연구는 현재까지 보고된 바가 없다.On the other hand, studies related to the routine production using buckwheat is a method for producing a buckwheat extract with an increased content of rutin through germination in consideration of the small amount of rutin in buckwheat [Korea Patent No. 0154582, 1998], rutin A method of preparing buckwheat fermentation broth with an increased content of [Korean Patent No. 115448, 1997] is reported. In addition, there have been studies on the production of enzyme-treated alpha-glycosyl routines (Japanese Patent Publication No. 32,073 / 79) which have improved the practical value of poorly soluble routines, and a study on a method of extracting high purity natural routines of more than 95% purity from buckwheat. Has not been reported to date.
이에, 본 발명자들은 메밀에 함유되어 있는 루틴의 상기와 같은 우수한 효능을 인식하고 이를 산업적인 면에서 좀더 효율적이며 다양하게 이용 가능하도록 다각도로 연구한 결과, 종래 루틴은 소량 함유되어 있으면서 루틴 외의 다른 성분이 다량인 메밀 가공물을 그대로 이용하던 방법 대신, 메밀의 기능성 물질인 루틴만을 고순도로 추출하였다. 즉, 메밀 전초의 건조물로부터 루틴을 추출함에 있어서 용매, 온도, 시간 등 최적의 추출조건을 확립하고, 루틴의 물리화학적 특성을 이용한 다공성 흡착수지 및 재결정을 통해 루틴을 고순도로 분리하는 방법을 알게 됨으로써 본 발명을 완성하였다.Accordingly, the present inventors have recognized the above excellent efficacy of the routine contained in buckwheat and researched it from various angles to make it more efficient and versatile in industrial use. As a result, the conventional routine contains a small amount of other components except routines. Instead of using this large amount of buckwheat processed product as it is, only rutin which is a functional material of buckwheat was extracted with high purity. In other words, by extracting the rutin from the dried buckwheat starch, the optimum extraction conditions such as solvent, temperature and time are established, and the method of separating the rutin with high purity through porous adsorption resin and recrystallization using the physicochemical properties of the rutin is known. The present invention has been completed.
따라서, 본 발명은 메밀 추출물 내의 루틴의 순도를 월등히 향상시켜 그 활용범위를 넓히고 막대한 양의 농업 부산물로부터 경제적 고부가가치를 창출할 수 있는 고농도 천연 루틴의 추출방법을 제공하는데 그 목적이 있다.Accordingly, an object of the present invention is to provide a method for extracting high concentration natural routines which can greatly improve the purity of rutin in buckwheat extract to broaden its application range and create economic high value from enormous amounts of agricultural by-products.
도 1은 본 발명에 따라 메밀로부터 추출된 천연 루틴의 HPLC 그래프를 나타낸 것이다.1 shows an HPLC graph of natural rutin extracted from buckwheat according to the present invention.
도 2는 종래 화학 합성법에 의해 제조된 루틴(SIGMA Chem. Co. USA)의 HPLC 그래프를 나타낸 것이다.Figure 2 shows the HPLC graph of the routine (SIGMA Chem. Co. USA) prepared by the conventional chemical synthesis method.
본 발명은 메밀로부터 천연 루틴을 추출하는 방법에 있어서,The present invention provides a method for extracting natural rutin from buckwheat,
건조된 메밀 전초 1 중량부에 대하여 50% 아세톤 수용액 또는 50% 에탄올 수용액 5 ∼ 10 중량부를 첨가하고 60 ∼ 80 ℃의 온도에서 1 ∼ 2시간 동안 환류한 후, 여과 또는 원심분리한 다음 농축하여 루틴 추출물을 얻는 공정,5 to 10 parts by weight of a 50% acetone solution or 50% ethanol solution and refluxed at a temperature of 60 to 80 ℃ for 1 to 2 hours, filtered or centrifuged, and concentrated to 1 part by weight of dried buckwheat starch Process of obtaining the extract,
상기 루틴 추출물을 스티렌계 다공성 흡착수지에 충전시킨 후, 물 및 20% 에탄올 수용액으로 세척한 후, 30% 에탄올 수용액 3 ∼ 5 중량부를 첨가하여 용출시키고 감압농축하여 루틴 고형분을 얻는 공정, 그리고After filling the routine extract with a styrene-based porous adsorption resin, washed with water and 20% ethanol aqueous solution, 3 to 5 parts by weight of 30% ethanol aqueous solution was added to elute and concentrated under reduced pressure to obtain a routine solid, and
상기 루틴 고형분을 60 ∼ 80 ℃의 물 5 ∼ 10 중량부에 첨가하여 가용성분을 용해시킨 후, 4 ∼ 10 ℃에서 정치시켜 루틴을 재결정하는 공정으로 이루어진 메밀로부터 고순도 천연 루틴을 추출하는 방법을 그 특징으로 한다.A method of extracting high purity natural rutin from buckwheat comprising the step of adding the above-mentioned routine solids to 5 to 10 parts by weight of water at 60 to 80 ° C. to dissolve the soluble component and then standing still at 4 to 10 ° C. to recrystallize the routine. It features.
이와 같은 본 발명을 더욱 상세히 설명하면 다음과 같다.Referring to the present invention in more detail as follows.
본 발명은 고혈압, 뇌혈관 질환 등에 예방 및 치료효과가 있는 생리활성 물질인 루틴을 순도 95% 이상으로 얻을 수 있는 천연 루틴의 추출방법에 관한 것이다.The present invention relates to a method for extracting natural rutin which can obtain a routine, which is a bioactive substance having a prophylactic and therapeutic effect on hypertension, cerebrovascular disease, etc., with a purity of 95% or more.
본 발명에 따른 메밀로부터 고순도 천연 루틴의 추출방법을 단계별로 더욱 구체화하여 설명하면 다음과 같다.The method of extracting high purity natural rutin from buckwheat according to the present invention will be described in more detail step by step as follows.
제 1 공정으로, 건조된 메밀 전초(잎, 줄기, 꽃, 씨를 포함.)로부터 루틴 추출물을 얻는 과정을 수행한다. 본 발명에서는 건조된 메밀을 준비한 후 추출용매로서 50% 아세톤 수용액 또는 50% 에탄올 수용액을 사용하며, 이를 메밀 1 중량부에 대하여 5 ∼ 10 중량부 첨가하여 60 ∼ 80 ℃의 온도에서 에지테이터 등으로 교반하면서 1 ∼ 2시간 동안 환류시킨다. 그 다음, 이를 착즙하고 여과 또는 원심분리하여 1차 추출물을 얻은 후 이의 잔사를 가지고 상기 과정을 반복 실시하고, 상기 1, 2차 추출물을 혼합하여 3 ∼ 5 브릭스로 감압농축함으로써 농축된 루틴 추출물을 얻는다.In a first process, a routine extract is obtained from dried buckwheat outposts (including leaves, stems, flowers, and seeds). In the present invention, after preparing dried buckwheat, 50% acetone aqueous solution or 50% ethanol aqueous solution is used as an extraction solvent, and 5-10 parts by weight of the buckwheat is added to 1 part by weight of buckwheat and then used as an edge data at a temperature of 60-80 ° C. It is refluxed for 1-2 hours with stirring. Then, the extract was filtered and filtered or centrifuged to obtain a primary extract, and then the above procedure was repeated with the residue thereof, and the primary and secondary extracts were mixed and concentrated under reduced pressure to 3 to 5 briquettes to concentrate the concentrated extract. Get
상기 추출용매로서 50% 아세톤 수용액 또는 50% 에탄올 수용액을 사용하는 이유는 열수, 50% 메탄올 수용액, 50% 이소프로판올 수용액을 사용한 것에 비하여 메밀로부터 루틴의 추출수율이 높기 때문이다. 이때, 추출용매를 5 중량부 미만으로 첨가하면 안정적인 수율을 얻을 수 없고, 10 중량부를 초과하면 추출공정시 소요비용이 상승하여 경제적으로나 산업적으로 불리하다. 그리고, 추출온도가 60 ℃를 초과할 때 추출수율이 높아졌으며, 추출공정의 안정성과 루틴의 열변성을 고려할 때 80℃를 초과하지 않는 것이 바람직하다. 또한, 교반함으로써 루틴의 추출수율이 증가되며, 상기 추출공정을 반복하였는 바, 그 이유는 1차 추출물과 2차 추출물을 혼합할 경우 루틴의 추출효율이 증가되기 때문이다.The reason why the 50% acetone aqueous solution or the 50% ethanol aqueous solution is used as the extraction solvent is that the yield of rutin extraction from buckwheat is higher than that of hot water, 50% methanol aqueous solution and 50% isopropanol aqueous solution. At this time, if the extraction solvent is added less than 5 parts by weight, a stable yield cannot be obtained, and if it exceeds 10 parts by weight, the required cost increases during the extraction process, which is economically and industrially disadvantageous. In addition, the extraction yield was increased when the extraction temperature exceeds 60 ℃, it is preferable not to exceed 80 ℃ considering the stability of the extraction process and the thermal modification of the routine. In addition, the extraction yield of the routine is increased by stirring, and the extraction process is repeated because the extraction efficiency of the routine is increased when the primary and secondary extracts are mixed.
이와 같은 방법으로 제조된 추출물의 루틴함량을 평가하기 위해 HPLC의 분석방법으로[Park, G. L. et al., Identification of Bioflavonoids from Citrus, Food Technol., 36(12), 98, 1983; Ohara, Tet al., Determination of Rutin in Buckwheat Foods by HPLC, Nippon Shokuhin Kogyo Gakkaishi, 36, 114, 1989] 루틴의 함량을 특정하였는데 그 결과, 936.2 mg%(메밀건초 100g을 사용할 때, 추출된 루틴의 양이 936.2mg임을 의미함)의 값을 얻었으며, 이는 극히 낮은 함량으로 그 활용의 범위가 제한되어 있어서 루틴의 함량을 향상시키는 방법에 대한 개발이 절실히 요구된다.In order to evaluate the rutin content of the extract prepared in this manner by HPLC analysis [Park, GL et al., Identification of Bioflavonoids from Citrus, Food Technol., 36 (12), 98, 1983; Ohara, T et al ., Determination of Rutin in Buckwheat Foods by HPLC, Nippon Shokuhin Kogyo Gakkaishi, 36, 114, 1989] specified the content of the routine, resulting in 936.2 mg% (when using 100 g of buckwheat hay). It means that the amount of is 936.2mg), which is extremely low content, the scope of its use is limited, so the development of a method for improving the content of the routine is urgently needed.
따라서, 본 발명에서는 제 2 공정으로, 스티렌계 다공성 흡착수지를 이용하여 순도 50 % 이상으로 정제하는 공정을 수행한다. 즉, 흡착면적이 커서 분자량이 큰 유기물의 흡착제로 사용되는 스티렌계 다공성 합성수지가 충진된 컬럼에통과시켜 루틴을 전분질, 당질 등 기타 성분으로부터 효과적으로 분리하는 것이다. 이는 루틴에 대한 스티렌계 다공성 합성수지의 흡착력이 기타성분에 비해 큰 성질을 이용한 것이다. 먼저, 상기 루틴 추출물을 상기 컬럼에 붓고, 물 10 ∼ 20 중량부를 첨가하여 1차 용출한 다음, 20 % 에탄올 수용액 5 ∼ 7 중량부를 첨가하여 2차 용출한다. 여기서 용출된 분획물의 루틴 회수율은 0.5 % 이하로 다음 공정에 사용되지 않는다. 그 다음, 30 % 에탄올 수용액 3 ∼ 5 중량부를 첨가하여 3차 용출한 후 40 ∼ 50 ℃에서 감압농축하는데, 여기서 용출된 분획물은 순도가 50 % 이상이며, 회수율은 98 % 이상으로 다음 공정에 사용된다. 이때, 3차 용출용매를 3 중량부 미만으로 첨가하면 유효성분이 충분히 용출되지 않고, 5 중량부를 초과하면 제조비의 상승으로 경제적으로나 산업적으로 불리하다. 또한, 용출시 용매의 유속조건은 10 ∼ 100 ㎖/min이 바람직하며, 유속이 100 ㎖/min를 초과할 경우 흡착시간이 충분하지 않아 수율이 저하되고, 유속이 10 ㎖/min 미만일 경우 공정시간이 과도하게 길어지게 된다.Therefore, in the present invention, as a second process, a process of purifying 50% or more purity using a styrene-based porous adsorption resin is performed. That is, the routine is effectively separated from other components such as starch, sugar, and the like by passing through a column filled with a styrene-based porous synthetic resin used as an adsorbent for organic molecules having a large molecular weight due to its large adsorption area. This is because the adsorption power of styrene-based porous synthetic resin to rutin is greater than other components. First, the routine extract is poured into the column, firstly eluted by adding 10 to 20 parts by weight of water, and then secondly eluted by adding 5 to 7 parts by weight of an aqueous 20% ethanol solution. The routine recovery rate of the fraction eluted here is less than 0.5% and is not used in the next process. Then, 3 to 5 parts by weight of an aqueous 30% ethanol solution was eluted in 3rd, and concentrated under reduced pressure at 40 to 50 ° C., where the eluted fraction had a purity of 50% or higher and a recovery rate of 98% or higher for use in the next step. do. In this case, when the third eluting solvent is added to less than 3 parts by weight, the active ingredient is not sufficiently eluted, and if it exceeds 5 parts by weight, it is economically and industrially disadvantageous due to an increase in manufacturing cost. In addition, the flow rate of the solvent during elution is preferably 10 ~ 100 ㎖ / min, and if the flow rate exceeds 100 ㎖ / min, the adsorption time is not enough, the yield is reduced, the process time when the flow rate is less than 10 ㎖ / min This becomes excessively long.
제 3 공정으로, 상기 마지막 분획물을 재결정하여 순도 95 % 이상으로 정제한다. 이는 물에 대한 루틴의 난용성을 이용한 것으로 상온에서 물 8ℓ당 약 1g 정도 용해된다(0.0125 w/v% 용해). 즉, 상기 순도 50 % 이상의 루틴 분획물 내의 비루틴계 성분은 대부분 물에 대해 가용성인 반면, 루틴은 난용성인 성질을 이용한 것이다. 상기 분획물을 60 ∼ 80 ℃의 물 5 ∼ 10 중량부에 첨가하여 가용성인 성분들을 완전히 용해시킨다. 이때, 용매를 5 중량부 미만으로 첨가하면 비루틴계 가용성 성분이 충분히 용해되지 않으며, 10 중량부 이상 초과하여과량으로 첨가하면, 상등액의 제거공정이 길어지게 되어 제조비의 상승으로 경제적으로 바람직하지 않다. 또한, 여기서 일부 황색∼엷은 황녹색의 침전물이 형성되는데, 이 침전물은 고순도의 루틴 결합체로 완전히 용해시키지 않아도 된다. 그 다음, 상기 용액을 4 ∼ 10 ℃의 저온조건에서 12 ∼ 24시간 동안 정치시켜 루틴의 재결정을 유도하고, 원심분리(2,000 ×g, 20분)를 통해 상등액을 분리시켜 제거한 후 재결정된 루틴을 자연건조한다. 최종 순도를 HPLC법으로 검정한 결과 루틴의 순도는 95 % 이상이었으며, 루틴 회수율은 92 % 이상인 것으로 분석되었다.In a third process, the last fraction is recrystallized and purified to a purity of at least 95%. It takes advantage of the routine solubility of water and dissolves about 1 g per 8 liters of water (0.0125 w / v% dissolution) at room temperature. That is, most of the non-routine-based components in the rutin fraction having a purity of 50% or more are soluble in water, while rutin uses poorly soluble properties. The fraction is added to 5-10 parts by weight of water at 60-80 ° C. to completely dissolve the soluble components. At this time, if the solvent is added less than 5 parts by weight, the non-routine-based soluble component is not sufficiently dissolved, and if it is added in excess of 10 parts by weight or more, the process of removing the supernatant is lengthened, which is economically unfavorable due to the increase in manufacturing cost. . In addition, some yellow to pale yellow green precipitates are formed here, and the precipitates do not have to be completely dissolved in a high purity routine binder. Then, the solution was allowed to stand for 12 to 24 hours at a low temperature of 4 to 10 ° C. to induce recrystallization of the routine. The supernatant was separated and removed by centrifugation (2,000 × g, 20 minutes), and then the recrystallized routine was removed. Dry naturally. As a result of assaying the final purity by HPLC method, the purity of the routine was 95% or more, and the routine recovery was analyzed to be 92% or more.
따라서, 이상과 같은 본 발명에 따른 고순도 천연 루틴 추출방법은 공정면에서 경제적일 뿐 아니라 그 활용 범위가 다양하여 의약품, 식료품, 화장품 등에 널리 사용될 수 있다.Therefore, the high-purity natural routine extraction method according to the present invention as described above is not only economical in terms of process, but also can be widely used in medicines, foodstuffs, cosmetics, etc., since the application range is various.
이에 본 발명을 실시예에 의거하여 더욱 상세히 설명하는 바, 본 발명이 실시예에 의해 한정되는 것은 아니다.Therefore, the present invention will be described in more detail with reference to Examples, but the present invention is not limited by Examples.
참조예 1 : 최적 추출 용매의 선정Reference Example 1 Selection of Optimal Extraction Solvent
잘 건조된 메밀 전초 25 g에 다음 표 1의 추출용매 250 ㎖를 첨가하여 80 ℃에서 60 rpm으로 교반하면서 2시간 동안 에지테이터로 교반하면서 환류추출하였다. 추출이 종료된 후, 착즙 및 여과하여 추출액만을 모았다(1차 추출물). 그리고, 남은 잔사에 동일한 추출과정을 반복 수행하였다(2차 추출물). 상기 1, 2차 추출물을 혼합하고 HPLC를 통해 루틴의 추출량을 측정하여 그 결과를 다음 표 1에 나타내었다.To 250 g of well dried buckwheat starch, 250 ml of the extraction solvent shown in Table 1 was added thereto, and the mixture was extracted under reflux with stirring at edge temperature for 2 hours while stirring at 80 rpm at 60 rpm. After the extraction was completed, juice and filtration collected only the extract (primary extract). And, the same extraction process was repeated to the remaining residue (secondary extract). The primary and secondary extracts were mixed and the extraction amount of rutin was measured through HPLC, and the results are shown in Table 1 below.
상기 표 1에 나타낸 결과를 통해서 볼 때, 50 % 아세톤 수용액을 추출용매로 사용할 때 루틴의 추출량이 가장 높았으며, 50 % 에탄올 수용액을 추출용매로 사용할 경우에도 거의 동등한 추출효과가 있는 것을 알 수 있었다. 따라서, 추출용매로서 50 % 아세톤 수용액, 50 % 에탄올 수용액 중 어느 용매계를 사용하여도 무방한 것으로 판단되었다.From the results shown in Table 1, when the 50% acetone aqueous solution was used as the extraction solvent, the extraction amount of rutin was the highest, and even when using 50% ethanol aqueous solution as the extraction solvent, it was found that the extraction effect was almost equivalent. . Therefore, it was judged that either solvent system of 50% acetone aqueous solution and 50% ethanol aqueous solution could be used as the extraction solvent.
참조예 2 : 최적 추출온도의 선정Reference Example 2: Selection of Optimum Extraction Temperature
상기 참조예 1에서 선정된 추출용매인 50 % 아세톤 수용액을 사용하여 다음 표 2에 나타낸 바와 같은 온도에서 참조예 1과 동일한 방법으로 수행하였다. 그리고, 상기 참조예 1과 동일한 방법으로 루틴의 추출량 및 추출효율을 측정하여 그 결과를 다음 표 2에 나타내었다.Using the 50% acetone aqueous solution of the extraction solvent selected in Reference Example 1 was carried out in the same manner as in Reference Example 1 at a temperature as shown in Table 2. In addition, the extraction amount and extraction efficiency of the routine was measured in the same manner as in Reference Example 1, and the results are shown in Table 2 below.
상기 표 2에 나타낸 결과를 통해서 보면, 50 % 아세톤 수용액을 사용할 때 60 ∼ 80 ℃에서 특히, 80 ℃에서 수행한 경우 추출효율이 가장 높음을 알 수 있었다.From the results shown in Table 2, it was found that the extraction efficiency is the highest when performed at 60 to 80 ℃, especially at 80 ℃ when using 50% acetone aqueous solution.
참조예 3 : 최적 추출시간의 선정Reference Example 3: Selection of Optimal Extraction Time
추출용매로서 50 % 아세톤 수용액을 사용하고, 상기 참조예 2에서 최적의 온도로 선정된 80 ℃에서, 다음 표 3에 나타낸 바와 같은 시간 동안 수행하는 것을 제외하고는 참조예 1과 동일한 방법으로 수행하였다. 그리고, 상기 참조예 1과 동일한 방법으로 루틴의 추출량 및 추출효율을 측정하여 그 결과를 다음 표 3에 나타내었다.A 50% acetone aqueous solution was used as the extraction solvent, and was carried out in the same manner as in Reference Example 1, except that it was performed at 80 ° C. selected as the optimum temperature in Reference Example 2 for a time as shown in Table 3 below. . In addition, the extraction amount and extraction efficiency of the routine was measured in the same manner as in Reference Example 1, and the results are shown in Table 3 below.
상기 표 3에 나타낸 결과를 통해서 볼 때, 50 % 아세톤 수용액을 추출용매로 사용하여 80 ℃에서 수행할 때, 추출시간은 1 ∼ 2 시간으로 한 경우 추출효율이 가장 높음을 알 수 있었다.From the results shown in Table 3, it was found that when the extraction time is performed at 80 ℃ using a 50% acetone aqueous solution as the extraction solvent, the extraction efficiency is the highest when the extraction time is 1 to 2 hours.
실시예 1Example 1
상기 참조예 1 ∼ 3에서 얻은 최적의 추출조건 즉, 추출용매로 50 % 아세톤 수용액을 사용하여 80 ℃에서 2시간 동안 참조예 1과 동일한 방법으로 실시한 후, 이를 감압농축기로 농축하여 5 브릭스의 농축물을 제조하였다. 상기 농축물 50 g을 스티렌계 공업용 흡착수지로 충진된 컬럼(60 ×450 ㎜)에 충전시킨 후, 물1000 ㎖를 사용하여 용출유속 50 ㎖/min로 컬럼을 통과시켜 세척하고, 다시 20 % 에탄올 수용액 350 ㎖를 사용하여 세척하였다. 여기에 다시 30% 에탄올 수용액 250 ㎖를 컬럼에 통과시켜 루틴이 함유된 용출 분획물을 얻었다. 이어서, 상기 물, 20 % 에탄올 수용액, 30 % 에탄올 수용액의 용출 분획물을 각각 감압농축하여 건조 고형분을 제조하고, HPLC로 각 고형분내의 루틴 순도와 회수율을 측정하였으며, 그 결과를 다음 표 4에 나타내었다.Optimal extraction conditions obtained in Reference Examples 1 to 3, namely, using a 50% acetone aqueous solution as the extraction solvent was carried out in the same manner as in Reference Example 1 for 2 hours at 80 ℃, and then concentrated in a vacuum condenser to concentrate 5 Brix Water was prepared. 50 g of the concentrate was charged to a column (60 x 450 mm) filled with styrene-based industrial adsorption resin, and then washed by passing the column at an elution rate of 50 ml / min using 1000 ml of water, followed by 20% ethanol. Wash with 350 ml aqueous solution. Again 250 ml of 30% aqueous ethanol solution was passed through the column to obtain an eluate fraction containing rutin. Subsequently, the elution fractions of the water, 20% aqueous ethanol solution and 30% aqueous ethanol solution were concentrated under reduced pressure to prepare dry solids, and the purity and recovery rate of the solids in each solid were measured by HPLC. The results are shown in Table 4 below. .
상기 표 4에서 보면, 30 % 에탄올 수용액으로 용출시킨 분획의 경우 순도가 50 % 이상인 루틴을 얻을 수 있을 뿐 아니라 98 % 이상의 회수율로 고효율임을 알 수 있었다.In Table 4, the fraction eluted with a 30% ethanol aqueous solution was found to be highly efficient with a recovery rate of 98% or higher as well as a routine having a purity of 50% or higher.
실시예 2Example 2
상기 실시예 1에서 얻은 순도 50% 이상의 루틴 분획물 2 g을 80 ℃의 물 20 ㎖에 첨가하여 가용성분을 완전히 용해시켰다. 그 다음, 상기 용액을 4 ℃에서12시간 동안 정치시켜두어 루틴성분이 결정화된 침전물을 얻고, 이를 원심분리(2,000 ×g, 20분)하여 상등액을 제거한 후, 재결정된 루틴을 자연건조하여 분말형태로 991.0 mg을 얻었다. 이렇게 얻은 분말을 HPLC를 이용하여 분석한 결과, 루틴의 순도는 95.36 %이고 회수율은 92.11 %인 것으로 확인되었다. 또한, HPLC 그래프를 도 1에 도시하였으며, 순도 95 % 이상임이 공증된 화학 합성 루틴(SIGMA Chem. Co. USA)의 HPLC 그래프를 도 2에 나타내어 비교하였다. 상기 재결정 방법을 이용하면 순도가 95 % 이상인 고순도 루틴을 얻을 수 있을 뿐 아니라 92 % 이상의 회수율로 고효율임을 확인하였다.2 g of a routine fraction having a purity of 50% or more obtained in Example 1 was added to 20 ml of water at 80 ° C to completely dissolve the soluble component. Then, the solution was left to stand for 12 hours at 4 ℃ to obtain a precipitate crystallized rutin components, centrifuged (2,000 × g, 20 minutes) to remove the supernatant, and then the recrystallized rutin was naturally dried to form a powder Obtained 991.0 mg. As a result of analyzing the powder thus obtained using HPLC, it was confirmed that the purity of the routine was 95.36% and the recovery was 92.11%. In addition, the HPLC graph is shown in FIG. 1, and the HPLC graph of the chemical synthesis routine (SIGMA Chem. Co. USA) notified of purity of 95% or more is shown in FIG. 2 and compared. By using the recrystallization method, not only a high purity routine having a purity of 95% or more can be obtained, but also a high efficiency with a recovery rate of 92% or more.
상술한 바와 같이, 본 발명의 메밀로부터 고순도 천연 루틴의 추출방법은 있어서 최적의 용매 및 최적의 추출조건으로 추출물을 얻고, 이를 다공성 흡착수지를 이용하여 분획하고, 재결정을 실시하여 메밀 추출물 내 루틴의 순도를 월등히 향상시킴으로써 그 활용 범위를 넓혀 의약품, 식품, 화장품 및 플라스틱 분야에 효과적으로 널리 응용될 수 있을 뿐 아니라 막대한 양의 농산 부산물로부터 경제적 고부가가치를 창출하는 효과가 있다.As described above, in the extraction method of high purity natural rutin from the buckwheat of the present invention, the extract is obtained by the optimum solvent and the optimum extraction conditions, fractionated using a porous adsorptive resin, and recrystallized to carry out the re-crystallization of the rutin in the buckwheat extract. Significantly improved purity extends its range of applications, effectively expanding its application to medicine, food, cosmetics and plastics, as well as creating high economic value from a huge amount of agricultural by-products.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100646126B1 (en) | 2004-11-22 | 2006-11-23 | 춘천시 | A Method For Preparing of Rutin Extract and Rutin Powder from Buckwheat Herbs |
| KR20210059236A (en) | 2019-11-15 | 2021-05-25 | 주식회사 제이크리에이션 | Method of producing the extract of rutin using functional buckwheat buds |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050204619A1 (en) * | 2002-04-30 | 2005-09-22 | Yoon Chang Park | Method of extracting rutin from buck wheat growed by hydroponics |
| KR100708409B1 (en) * | 2005-09-27 | 2007-04-19 | 김옥순 | Rutin Extract Method from Buckwheat Bud and extracted rutin |
| CN102641343A (en) * | 2012-05-05 | 2012-08-22 | 耿福能 | Water-soluble tartary buckwheat general flavone extract and preparation method and application thereof |
| CN102948758B (en) * | 2012-11-26 | 2014-07-30 | 陕西科技大学 | Method for extracting buckwheat flavone from buckwheat bran |
| CN107793457B (en) * | 2017-09-20 | 2020-09-01 | 中国农业科学院茶叶研究所 | Green preparation method of flos sophorae immaturus rutin |
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| KR910002518A (en) * | 1989-07-22 | 1991-02-25 | 아라이 가즈오 | Plate fixed structure |
| KR100186285B1 (en) * | 1995-12-07 | 1999-03-20 | 신기석 | Purifying process of crocine |
| KR100319251B1 (en) * | 1999-06-30 | 2002-01-05 | 한수길 | Manufacturing process of Glucosyltransferase Inhibitors from Cacao Bean Husk |
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- 2000-08-23 KR KR1020000048918A patent/KR100361632B1/en active IP Right Grant
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR910002518A (en) * | 1989-07-22 | 1991-02-25 | 아라이 가즈오 | Plate fixed structure |
| KR100186285B1 (en) * | 1995-12-07 | 1999-03-20 | 신기석 | Purifying process of crocine |
| KR100319251B1 (en) * | 1999-06-30 | 2002-01-05 | 한수길 | Manufacturing process of Glucosyltransferase Inhibitors from Cacao Bean Husk |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100646126B1 (en) | 2004-11-22 | 2006-11-23 | 춘천시 | A Method For Preparing of Rutin Extract and Rutin Powder from Buckwheat Herbs |
| KR20210059236A (en) | 2019-11-15 | 2021-05-25 | 주식회사 제이크리에이션 | Method of producing the extract of rutin using functional buckwheat buds |
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| Publication number | Publication date |
|---|---|
| KR20020015805A (en) | 2002-03-02 |
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