KR102229831B1 - A Composition for extracting effective ingredients from plant comprising deep eutectic solvent and a method for extracting effective ingredients from plant using the same - Google Patents

A Composition for extracting effective ingredients from plant comprising deep eutectic solvent and a method for extracting effective ingredients from plant using the same Download PDF

Info

Publication number
KR102229831B1
KR102229831B1 KR1020180135363A KR20180135363A KR102229831B1 KR 102229831 B1 KR102229831 B1 KR 102229831B1 KR 1020180135363 A KR1020180135363 A KR 1020180135363A KR 20180135363 A KR20180135363 A KR 20180135363A KR 102229831 B1 KR102229831 B1 KR 102229831B1
Authority
KR
South Korea
Prior art keywords
plant
extraction
active ingredient
extracting
solvent
Prior art date
Application number
KR1020180135363A
Other languages
Korean (ko)
Other versions
KR20200052147A (en
Inventor
노경호
당위양
이계진
안예나
Original Assignee
인하대학교 산학협력단
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 인하대학교 산학협력단 filed Critical 인하대학교 산학협력단
Priority to KR1020180135363A priority Critical patent/KR102229831B1/en
Publication of KR20200052147A publication Critical patent/KR20200052147A/en
Application granted granted Critical
Publication of KR102229831B1 publication Critical patent/KR102229831B1/en

Links

Images

Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D11/00Solvent extraction
    • B01D11/02Solvent extraction of solids
    • B01D11/0288Applications, solvents
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D11/00Solvent extraction
    • B01D11/02Solvent extraction of solids
    • B01D11/0261Solvent extraction of solids comprising vibrating mechanisms, e.g. mechanical, acoustical
    • B01D11/0265Applying ultrasound

Abstract

공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물 및 상기 추출용 조성물을 사용하여 식물체로부터 유효성분을 추출하는 방법에 관한 것으로, 상기 조성물은 간단한 제조공정으로 쉽게 제조할 수 있으며, 반응과정에서 추가적인 유기용제를 사용할 필요가 없으며, 유기용매를 사용하지 않음에 따라, 독성물질 방출 및 부산물이 없어 환경오염 물질 배출이 적을 것으로 기대된다. 또한, 다양한 식물체로부터 유효성분을 우수한 순도 및 수율로 추출할 수 있다. 이에, 본 발명에 따른 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물은 종래 유기용매의 추출용매를 대체하는 친환경적이고 경제적인 추출용매로 유용하게 사용될 수 있다.It relates to an extraction composition for extracting an active ingredient from a plant containing a eutectic solvent, and a method of extracting the active ingredient from a plant using the extraction composition, wherein the composition can be easily prepared by a simple manufacturing process, and the reaction There is no need to use an additional organic solvent in the process, and as no organic solvent is used, there is no emission of toxic substances and no by-products, so it is expected that there will be less emission of environmental pollutants. In addition, active ingredients can be extracted from various plants with excellent purity and yield. Accordingly, the extraction composition for extracting an active ingredient from a plant containing the eutectic solvent according to the present invention can be usefully used as an eco-friendly and economical extraction solvent replacing the extraction solvent of the conventional organic solvent.

Description

공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물 및 상기 추출용 조성물을 사용하여 식물체로부터 유효성분을 추출하는 방법{A Composition for extracting effective ingredients from plant comprising deep eutectic solvent and a method for extracting effective ingredients from plant using the same}A composition for extracting effective ingredients from plant comprising deep eutectic solvent and a method for extracting effective ingredients from plant using the same}

공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물 및 상기 추출용 조성물을 사용하여 식물체로부터 유효성분을 추출하는 방법에 관한 것이다.It relates to an extraction composition for extracting an active ingredient from a plant containing a eutectic solvent, and a method of extracting the active ingredient from a plant using the extraction composition.

폴리페놀(Polyphenols)은 식물, 특히 자연식물의 자연 산화 방지제이며 신체의 활성산소 금속 이온의 친산화 금속 킬레이트화뿐만 아니라 항산화 효소 활성도, 항산화 효소 활성제 때문에 인간의 건강에 중요한 역할을 한다. 상기와 같은 이유로, 폴리페놀을 가진 부산물과 폐기물의 이용에 관한 많은 연구가 이루어졌다. 연구는 대체로 효과적이고 비용 효율적인 다운스트림 공정의 개발에 초점이 맞춰졌으며, 이 공정은 식품, 식품 보충제, 화장품 및 의약품 제조에 사용되는 관점에서 추출물 또는 추출물의 정제에 기초하여 상품을 생산하는 것을 목표로 하는 것이 대다수이다.Polyphenols are natural antioxidants of plants, especially natural plants, and play an important role in human health because of their antioxidant enzyme activity and antioxidant enzyme activator, as well as the prooxidation metal chelation of free radical metal ions in the body. For the above reasons, many studies have been conducted on the use of waste products and by-products with polyphenols. Research has largely focused on the development of an effective and cost-effective downstream process, which aims to produce products on the basis of extracts or purification of extracts from the point of view of being used in the manufacture of foods, food supplements, cosmetics and pharmaceuticals. Most of them do.

구체적으로, 자연 식물에서 폴리페놀 화합물을 회수하기 위한 기존의 추출 기법은 보통 에탄올, 메탄올 또는 아세톤 용액과 같은 휘발성 유기 화합물(VOCs)을 추출용매로 사용하는 고-액 추출(leaching)이 주를 이룬다. 그러나, VOC 용제는 독성, 높은 변동성 및 비-재생성 특성으로 인해 소비자나 환경에 유리하지 않으며, REACH를 포함한 국제법에서는 이러한 용도의 사용을 엄격하게 규제하고 있다. Specifically, the existing extraction techniques for recovering polyphenol compounds from natural plants are usually solid-liquid leaching using volatile organic compounds (VOCs) such as ethanol, methanol or acetone solutions as extraction solvents. . However, VOC solvents are not beneficial to consumers or the environment due to their toxicity, high variability and non-renewable properties, and international law, including REACH, strictly regulates their use.

따라서, 환경 영향을 줄이기 위한 대체 녹색 용제를 찾는 동시에, 식품 폐기물 자재를 상업적 가치를 지닌 천연 폴리페놀 산화 방지제의 생산을 포함한 가치 있는 제품으로 업그레이드하기 위한 다운스트림 공정의 효율성을 개선해야 할 필요성이 증가하고 있다.Thus, there is a growing need to improve the efficiency of downstream processes to upgrade food waste materials to valuable products, including the production of natural polyphenol antioxidants of commercial value, while looking for alternative green solvents to reduce environmental impact. I'm doing it.

한편, 높은 용융점을 가진 고체물질과 혼합하여 형성된 새로운 유형의 용제로서, 자연 재료와 재생 가능한 시동 재료로 구성된 "공융 용매(Deep Eutectic Solvents)"라는 새로운 용매 시스템이 개발되었으며(Chem. Commun., 2003,0, 70-71), 상기 공융용매는 일반적으로 수소결합공여체(hydrogen bond donor, HBD)와 수소결합수용체(hydrogen bond acceptor, HBA)의 혼합으로 이루어져 있으며, 상기 HBD 및 HBA 조합에 따라 공융용매의 화학적 특성, 물리적 특성이 결정된다.On the other hand, as a new type of solvent formed by mixing with a solid material with a high melting point, a new solvent system called "Deep Eutectic Solvents" composed of natural materials and renewable starting materials has been developed (Chem. Commun., 2003). ,0, 70-71), the eutectic solvent is generally composed of a mixture of a hydrogen bond donor (HBD) and a hydrogen bond acceptor (HBA), and the eutectic solvent according to the combination of HBD and HBA The chemical and physical properties of are determined.

대한민국공개특허 1020150070610Korean Patent Publication 1020150070610

본 발명의 일 목적은 식물체로부터 유효성분을 추출하기 위한 추출용 조성물을 제공하는 것이다.One object of the present invention is to provide an extraction composition for extracting an active ingredient from a plant.

본 발명의 다른 목적은 식물체로부터 유효성분을 추출하는 방법을 제공하는 것이다.Another object of the present invention is to provide a method for extracting an active ingredient from a plant.

상기 목적을 달성하기 위하여,To achieve the above object,

본 발명의 일 측면에 따라, 물(water), 에틸렌 글리콜(ethylene glycol, EG), 우레아(Urea), 락트산(lactic acid, LA), 글리세롤(glycerol, GL), 옥살산(oxalic acid, OA) 및 n-부틸 알콜(n-butyl alcohol, BA)으로 이루어지는 군으로부터 선택되는 하나 이상의 수소결합공여체(Hydrogen bond donor, HBD); 및According to one aspect of the present invention, water, ethylene glycol (EG), urea (Urea), lactic acid (LA), glycerol (GLycerol, GL), oxalic acid (OA), and at least one hydrogen bond donor (HBD) selected from the group consisting of n-butyl alcohol (BA); And

염화 콜린(choline chloride, ChCl), 베타인(betaine, BT), 테트라부틸암모늄 브로마이드(tetrabutylammonium bromide, TBAB) 및 테트라메틸암모늄 클로라이드(tetramethylammonium chloride, TMAC)로 이루어지는 군으로부터 선택되는 하나 이상의 수소결합수용체(Hydrogen bond acceptor, HBA)의 혼합으로 구성되는 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물이 제공된다.At least one hydrogen bond receptor selected from the group consisting of choline chloride (ChCl), betaine (BT), tetrabutylammonium bromide (TBAB), and tetramethylammonium chloride (TMAC) ( An extraction composition for extracting an active ingredient from a plant comprising a eutectic solvent composed of a mixture of hydrogen bond acceptor, HBA) is provided.

본 발명의 다른 측면에 따라, According to another aspect of the invention,

식물체를 준비하는 단계(단계 1); 및Preparing a plant (Step 1); And

상기 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물, 상기 단계 1에서 준비된 식물체를 혼합하여 유효성분을 추출하는 단계를 포함하는 식물체로부터 유효성분을 추출하는 방법이 제공된다.An extraction composition for extracting an active ingredient from a plant containing the eutectic solvent, and a method of extracting an active ingredient from a plant comprising the step of extracting the active ingredient by mixing the plant prepared in step 1 is provided.

본 발명에 따른 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물은 간단한 제조공정으로 쉽게 제조할 수 있으며, 반응과정에서 추가적인 유기용제를 사용할 필요가 없으며, 유기용매를 사용하지 않음에 따라, 독성물질 방출 및 부산물이 없어 환경오염 물질 배출이 적을 것으로 기대된다. 또한, 다양한 식물체로부터 유효성분을 우수한 순도 및 수율로 추출할 수 있다. 이에, 본 발명에 따른 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물은 종래 유기용매의 추출용매를 대체하는 친환경적이고 경제적인 추출용매로 유용하게 사용될 수 있다.The extraction composition for extracting the active ingredient from the plant containing the eutectic solvent according to the present invention can be easily prepared by a simple manufacturing process, and there is no need to use an additional organic solvent in the reaction process, and the organic solvent is not used. Accordingly, it is expected that there will be little emission of environmental pollutants because there is no emission of toxic substances or by-products. In addition, active ingredients can be extracted from various plants with excellent purity and yield. Accordingly, the extraction composition for extracting an active ingredient from a plant containing the eutectic solvent according to the present invention can be usefully used as an eco-friendly and economical extraction solvent replacing the extraction solvent of the conventional organic solvent.

도 1은 본 발명 실시예1-13의 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물을 사용하여 오렌지 껍질(Orange peel)로부터 카페인산, 페룰산 및 루틴을 추출한 결과를 나타낸 것이다. (DES-1: 실시예 1, DES-2: 실시예 2, DES-3: 실시예 3, DES-4: 실시예 4, DES-5: 실시예 5, DES-6: 실시예 6, DES-7: 실시예 7, DES-8: 실시예 8, DES-9: 실시예 9, DES-10: 실시예 10, DES-11: 실시예 11, DES-12: 실시예 12, DES-13: 실시예 13, MeOH: 비교예 1)FIG. 1 shows the results of extracting caffeic acid, ferulic acid, and rutin from orange peel using an extraction composition for extracting an active ingredient from a plant containing the eutectic solvent of Example 1-13 of the present invention. . (DES-1: Example 1, DES-2: Example 2, DES-3: Example 3, DES-4: Example 4, DES-5: Example 5, DES-6: Example 6, DES -7: Example 7, DES-8: Example 8, DES-9: Example 9, DES-10: Example 10, DES-11: Example 11, DES-12: Example 12, DES-13 : Example 13, MeOH: Comparative Example 1)

이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.

본 발명의 일 측면은, One aspect of the present invention,

물(water), 에틸렌 글리콜(ethylene glycol, EG), 우레아(Urea), 락트산(lactic acid, LA), 글리세롤(glycerol, GL), 옥살산(oxalic acid, OA) 및 n-부틸 알콜(n-butyl alcohol, BA)으로 이루어지는 군으로부터 선택되는 하나 이상의 수소결합공여체(Hydrogen bond donor, HBD); 및Water, ethylene glycol (EG), urea, lactic acid (LA), glycerol (GL), oxalic acid (OA), and n-butyl alcohol alcohol, BA) at least one hydrogen bond donor selected from the group consisting of (Hydrogen bond donor, HBD); And

염화 콜린(choline chloride, ChCl), 베타인(betaine, BT), 테트라부틸암모늄 브로마이드(tetrabutylammonium bromide, TBAB) 및 테트라메틸암모늄 클로라이드(tetramethylammonium chloride, TMAC)로 이루어지는 군으로부터 선택되는 하나 이상의 수소결합수용체(Hydrogen bond acceptor, HBA)의 혼합으로 구성되는 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물을 제공한다.At least one hydrogen bond receptor selected from the group consisting of choline chloride (ChCl), betaine (BT), tetrabutylammonium bromide (TBAB), and tetramethylammonium chloride (TMAC) ( It provides an extraction composition for extracting an active ingredient from a plant comprising a eutectic solvent consisting of a mixture of hydrogen bond acceptor, HBA).

상기 식물체는 특히 한정되는 것은 아니나, 상기 식물체는 오렌지 껍질(Orange peel), 녹차(Green tea), 인진호(Herba Artemisiae Scopariae), 단삼(Salvia miltiorrhiza Bge), 은행나무(Ginkgo biloba L.), 인동 덩굴(Lonicera japonica), 회향(Fennel seed), 바닷말(seaweed) 및 민감초(Liquorice)로 이루어지는 군으로부터 선택되는 어느하나일 수 있다.The plant is not particularly limited, but the plant is orange peel, green tea, Injinho (Herba Artemisiae Scopariae), Dansam (Salvia miltiorrhiza Bge), Ginkgo biloba L., and honeysuckle vine. It may be any one selected from the group consisting of (Lonicera japonica), fennel seed, seaweed, and liquorice.

상기 유효성분은 식물체에 함유된 것으로, 특정한 효과, 예를들어, 항산화효과, 미백효과, 염증치료 효과 등의 효과를 나타내는 성분을 의미하며, 상기 유효성분은 카페인산(Caffeic acid), 페룰산(Ferulic acid), 루틴(Rutin), 클로로겐산(Chlorogenic acid) 및 글라브리딘(Glabridin)으로 이루어지는 폴리페놀 화합물로부터 선택되는 하나 이상일 수 있으나, 이에 한정되는 것은 아니다.The active ingredient is contained in the plant and refers to an ingredient that exhibits specific effects, such as an antioxidant effect, a whitening effect, and an inflammation treatment effect, and the active ingredient is caffeic acid, ferulic acid ( Ferulic acid), rutin, chlorogenic acid, and glabridin may be at least one selected from polyphenol compounds consisting of, but is not limited thereto.

상기 수소결합공여체(Hydrogen bond donor, HBD)는 에틸렌 글리콜(ethylene glycol, EG)일 수 있다.The hydrogen bond donor (HBD) may be ethylene glycol (EG).

상기 수소결합수용체(Hydrogen bond acceptor, HBA)는 테트라메틸암모늄 클로라이드(tetramethylammonium chloride, TMAC)일 수 있다.The hydrogen bond acceptor (HBA) may be tetramethylammonium chloride (TMAC).

상기 조성물에서, 수소결합수용체(Hydrogen bond acceptor, HBA) 1몰농도(Molar)에 대하여 수소결합공여체(Hydrogen bond donor, HBD)를 1 내지 4몰농도로 포함할 수 있다.In the composition, a hydrogen bond donor (HBD) may be included in a concentration of 1 to 4 molar to 1 molar concentration of a hydrogen bond acceptor (HBA).

수소결합수용체(Hydrogen bond acceptor, HBA) 1몰농도(Molar)에 대하여 수소결합공여체(Hydrogen bond donor, HBD)를 1몰농도 미만으로 포함할 경우, 녹는점이 실온보다 높고, 점성이 높아지는 문제가 발생할 수 있고, 4몰농도 초과로 포함할 경우, 추출용매로 사용시에 추출효율이 감소하는 문제가 발생할 수 있다.If a hydrogen bond donor (HBD) is contained in less than 1 molar concentration per 1 molar concentration of a hydrogen bond acceptor (HBA), the melting point is higher than room temperature and the viscosity increases. And, when it is included in an amount exceeding 4 molar concentration, there may be a problem in that the extraction efficiency decreases when used as an extraction solvent.

본 발명에 따른 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물은 간단한 제조공정으로 쉽게 제조할 수 있으며, 반응과정에서 추가적인 유기용제를 사용할 필요가 없으며, 유기용매를 사용하지 않음에 따라, 독성물질 방출 및 부산물이 없어 환경오염 물질 배출이 적을 것으로 기대된다. 또한, 다양한 식물체로부터 유효성분을 우수한 순도 및 수율로 추출할 수 있다(실험예 1 및 2 참조).The extraction composition for extracting the active ingredient from the plant containing the eutectic solvent according to the present invention can be easily prepared by a simple manufacturing process, and there is no need to use an additional organic solvent in the reaction process, and the organic solvent is not used. Accordingly, it is expected that there will be little emission of environmental pollutants because there is no emission of toxic substances or by-products. In addition, it is possible to extract the active ingredient from various plants with excellent purity and yield (see Experimental Examples 1 and 2).

이에, 본 발명에 따른 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물은 종래 유기용매의 추출용매를 대체하는 친환경적이고 경제적인 추출용매로 유용하게 사용될 수 있다.Accordingly, the extraction composition for extracting an active ingredient from a plant containing the eutectic solvent according to the present invention can be usefully used as an eco-friendly and economical extraction solvent replacing the extraction solvent of the conventional organic solvent.

상기 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물은,An extraction composition for extracting an active ingredient from a plant containing the eutectic solvent,

물(water), 에틸렌 글리콜(ethylene glycol, EG), 우레아(Urea), 락트산(lactic acid, LA), 글리세롤(glycerol, GL), 옥살산(oxalic acid, OA) 및 n-부틸 알콜(n-butyl alcohol, BA)으로 이루어지는 군으로부터 선택되는 하나 이상의 수소결합공여체(Hydrogen bond donor, HBD); 및 염화 콜린(choline chloride, ChCl), 베타인(betaine, BT), 테트라부틸암모늄 브로마이드(tetrabutylammonium bromide, TBAB) 및 테트라메틸암모늄 클로라이드(tetramethylammonium chloride, TMAC)로 이루어지는 군으로부터 선택되는 하나 이상의 수소결합수용체(Hydrogen bond acceptor, HBA)를 혼합하는 단계(단계 1);Water, ethylene glycol (EG), urea, lactic acid (LA), glycerol (GL), oxalic acid (OA), and n-butyl alcohol alcohol, BA) at least one hydrogen bond donor selected from the group consisting of (Hydrogen bond donor, HBD); And at least one hydrogen bond receptor selected from the group consisting of choline chloride (ChCl), betaine (BT), tetrabutylammonium bromide (TBAB), and tetramethylammonium chloride (TMAC). Mixing (Hydrogen bond acceptor, HBA) (Step 1);

단계 1의 혼합물을 가열하는 단계(단계2); 및Heating the mixture of step 1 (step 2); And

단계 2의 가열된 혼합물을 건조시키는 단계(단계 3);을 포함하는 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물의 제조방법을 통해 제조할 수 있다.Drying the heated mixture of step 2 (step 3); It can be prepared through a method for producing an extraction composition for extracting the active ingredient from the plant containing the eutectic solvent.

이하, 상기 제조방법을 상세히 설명한다.Hereinafter, the manufacturing method will be described in detail.

본 발명의 식물체로부터 유효성분을 추출하기 위한 추출용 조성물의 제조방법에 있어서, 상기 단계 1은 수소결합공여체와 수소결합수용체를 혼합하는 단계이다. 이때, 상기 수소결합수용체(Hydrogen bond acceptor, HBA) 1몰농도(Molar)에 대하여 수소결합공여체(Hydrogen bond donor, HBD)를 1 내지 4몰농도로 사용할 수 있다.In the method for preparing an extraction composition for extracting an active ingredient from a plant of the present invention, step 1 is a step of mixing a hydrogen bond donor and a hydrogen bond acceptor. In this case, a hydrogen bond donor (HBD) may be used in a concentration of 1 to 4 molar to 1 molar concentration of the hydrogen bond acceptor (HBA).

본 발명의 식물체로부터 유효성분을 추출하기 위한 추출용 조성물의 제조방법에 있어서, 상기 단계 2는 단계 1의 혼합물을 가열하는 단계이다.In the method for preparing an extraction composition for extracting an active ingredient from a plant of the present invention, step 2 is a step of heating the mixture of step 1.

상기 단계 2의 가열은 60°C 내지 120°C에서 수행할 수 있고, 80°C에서 수행할 수 있다.The heating of step 2 may be performed at 60 °C to 120 °C, and may be performed at 80 °C.

또한, 상기 단계 2의 가열은 0.5 내지 2시간동안 수행할 수 있다.In addition, the heating in step 2 may be performed for 0.5 to 2 hours.

본 발명의 식물체로부터 유효성분을 추출하기 위한 추출용 조성물의 제조방법에 있어서, 상기 단계 3은 단계 2의 가열된 혼합물을 건조하는 단계이다. 상기 건조는 오븐을 사용하여 수행할 수 있으며, 80°C 내지 120°C에서 수행할 수 있고, 80°C에서 수행할 수 있다.In the method for preparing an extraction composition for extracting an active ingredient from a plant of the present invention, step 3 is a step of drying the heated mixture of step 2. The drying may be performed using an oven, may be performed at 80 °C to 120 °C, and may be performed at 80 °C.

또한, 상기 단계 3의 건조는 12시간동안 수행할 수 있다.In addition, drying in step 3 may be performed for 12 hours.

상기 식물체로부터 유효성분을 추출하기 위한 추출용 조성물의 제조방법의 구체적인 실시방법은 하기 실시예 1-14와 유사한 절차를 수행하여 진행할 수 있으나, 이는 일례일 뿐, 이에 한정되는 것은 아니다.A specific method of manufacturing an extraction composition for extracting an active ingredient from the plant may be carried out by performing a procedure similar to Examples 1-14 below, but this is only an example and is not limited thereto.

본 발명의 다른 측면은, Another aspect of the present invention,

식물체를 준비하는 단계(단계 1); 및Preparing a plant (Step 1); And

상기 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물, 상기 단계 1에서 준비된 식물체를 혼합하여 유효성분을 추출하는 단계를 포함하는 식물체로부터 유효성분을 추출하는 방법을 제공한다.It provides a method for extracting an active ingredient from a plant comprising the step of extracting the active ingredient by mixing the composition for extracting the active ingredient from the plant containing the eutectic solvent, and the plant prepared in step 1 above.

이때, 상기 단계 2의 추출은 용액을 사용하여 추출할 수 있는 방법이면 제한되지 않고 사용할 수 있으나, 초음파 처리(Ultra sonic), 디핑(Dipping) 및 환류(Reflux) 등의 방법을 사용하여 추출할 수 있다.At this time, the extraction in step 2 may be used without limitation as long as it is a method that can be extracted using a solution, but it can be extracted using methods such as ultrasonic treatment (Ultra sonic), dipping, and reflux. have.

이하, 본 발명을 실시예 및 실험예에 의해 상세히 설명한다.Hereinafter, the present invention will be described in detail by examples and experimental examples.

단, 하기 실시예 및 실험예는 본 발명을 예시하는 것일 뿐, 본 발명의 내용이 하기 실시예 및 실험예에 한정되는 것은 아니다.However, the following Examples and Experimental Examples are merely illustrative of the present invention, and the contents of the present invention are not limited to the following Examples and Experimental Examples.

<실시예 1> 공융용매의 제조(DES-1)<Example 1> Preparation of eutectic solvent (DES-1)

에틸렌 글리콜(ethylene glycol, EG) 12.4 g(0.2 mol)과 물 1.8 g (0.1 mol)을 염화 콜린(choline chloride, ChCl) 14.00 g (0.1 mol)과 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시켜 공융용매 DES-1를 제조하였다.Mix 12.4 g (0.2 mol) of ethylene glycol (EG) and 1.8 g (0.1 mol) of water with 14.00 g (0.1 mol) of choline chloride (ChCl) and heat to 80 °C to completely If held for 1 hour until dissolved, a colorless transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-1 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 2> 공융용매의 제조(DES-2)<Example 2> Preparation of eutectic solvent (DES-2)

락트산(lactic acid, LA) 18 g(0.2 mol)과 물 1.8 g (0.1 mol)을 염화 콜린(choline chloride, ChCl) 14.00 g (0.1 mol)과 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-2를 제조하였다.Mix 18 g (0.2 mol) of lactic acid (LA) and 1.8 g (0.1 mol) of water with 14.00 g (0.1 mol) of choline chloride (ChCl) and heat to 80 °C to completely dissolve the material. If it is kept for 1 hour until it becomes clear, a colorless and transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-2 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 3> 공융용매의 제조(DES-3)<Example 3> Preparation of eutectic solvent (DES-3)

에틸렌 글리콜(ethylene glycol, EG) 24.8 g (0.4 mol)과 염화 콜린(choline chloride, ChCl) 14.00 g (0.1 mol)을 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-3를 제조하였다.Mix ethylene glycol (EG) 24.8 g (0.4 mol) and choline chloride (ChCl) 14.00 g (0.1 mol) together and heat to 80 °C for 1 hour until the material is completely dissolved When done, a colorless and transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-3 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 4> 공융용매의 제조(DES-4)<Example 4> Preparation of eutectic solvent (DES-4)

에틸렌 글리콜(ethylene glycol, EG) 18.6 g (0.3 mol)과 염화 콜린(choline chloride, ChCl) 14.00 g (0.1 mol)을 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-4를 제조하였다.Ethylene glycol (EG) 18.6 g (0.3 mol) and choline chloride (ChCl) 14.00 g (0.1 mol) are mixed together and heated to 80 °C for 1 hour until the material is completely dissolved. When done, a colorless and transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-4 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 5> 공융용매의 제조(DES-5)<Example 5> Preparation of eutectic solvent (DES-5)

에틸렌 글리콜(ethylene glycol, EG) 12.4 g (0.2 mol)과 염화 콜린(choline chloride, ChCl) 14.00 g (0.1 mol)을 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-5를 제조하였다.12.4 g (0.2 mol) of ethylene glycol (EG) and 14.00 g (0.1 mol) of choline chloride (ChCl) are mixed together and heated to 80 °C for 1 hour until the material is completely dissolved. When done, a colorless and transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-5 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 6> 공융용매의 제조(DES-6)<Example 6> Preparation of eutectic solvent (DES-6)

락트산(lactic acid, LA) 18 g (0.2 mol)과 염화 콜린(choline chloride, ChCl) 14.00 g (0.1 mol)을 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 물질이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-6를 제조하였다.When lactic acid (LA) 18 g (0.2 mol) and choline chloride (ChCl) 14.00 g (0.1 mol) are mixed together and heated to 80 °C, the material is kept for 1 hour until completely dissolved. A colorless transparent liquid is produced. After the material was completely finished, the eutectic solvent DES-6 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 7> 공융용매의 제조(DES-7)<Example 7> Preparation of eutectic solvent (DES-7)

옥살산(oxalic acid, OA) 18 g (0.2 mol)과 염화 콜린(choline chloride, ChCl) 14.00 g (0.1 mol)을 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-7를 제조하였다.When 18 g (0.2 mol) of oxalic acid (OA) and 14.00 g (0.1 mol) of choline chloride (ChCl) are mixed together, heated to 80 °C, and maintained for 1 hour until the material is completely dissolved. A colorless transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-7 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 8> 공융용매의 제조(DES-8)<Example 8> Preparation of eutectic solvent (DES-8)

락트산(lactic acid, LA) 18.4 g (0.2 mol)과 염화 콜린(choline chloride, ChCl) 14.00 g (0.1 mol)을 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-8를 제조하였다.When 18.4 g (0.2 mol) of lactic acid (LA) and 14.00 g (0.1 mol) of choline chloride (ChCl) are mixed together, heated to 80 °C and held for 1 hour until the material is completely dissolved. A colorless transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-8 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 9> 공융용매의 제조(DES-9)<Example 9> Preparation of eutectic solvent (DES-9)

n-부틸 알콜(n-butyl alcohol, BA) 14.8 g (0.2 mol)과 염화 콜린(choline chloride, ChCl) 14.00 g (0.1 mol)을 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-9를 제조하였다.14.8 g (0.2 mol) of n-butyl alcohol (BA) and 14.00 g (0.1 mol) of choline chloride (ChCl) are mixed together and heated to 80 °C until the material is completely dissolved. If held for 1 hour, a colorless transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-9 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 10> 공융용매의 제조(DES-10)<Example 10> Preparation of eutectic solvent (DES-10)

락트산(lactic acid, LA) 18.4 g (0.2 mol)과 베타인(betaine, BT) 11.7 g (0.1 mol)과 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-10를 제조하였다.It is colorless when mixed with lactic acid (LA) 18.4 g (0.2 mol) and betaine (BT) 11.7 g (0.1 mol) and heated to 80 °C for 1 hour until the material is completely dissolved. A clear liquid is produced. After the reaction was complete, the eutectic solvent DES-10 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 11> 공융용매의 제조(DES-11)<Example 11> Preparation of eutectic solvent (DES-11)

락트산(lactic acid, LA) 18.4 g (0.2 mol)과 테트라부틸암모늄 브로마이드(tetrabutylammonium bromide, TBAB) 32.2 g (0.1 mol)을 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-11를 제조하였다.Mix 18.4 g (0.2 mol) of lactic acid (LA) and 32.2 g (0.1 mol) of tetrabutylammonium bromide (TBAB) together and heat to 80 °C for 1 hour until the material is completely dissolved. If maintained, a colorless transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-11 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 12> 공융용매의 제조(DES-12)<Example 12> Preparation of eutectic solvent (DES-12)

락트산(lactic acid, LA) 18.4 g (0.2 mol)과 테트라메틸암모늄 클로라이드(tetramethylammonium chloride, TMAC) 10.9 g (0.1 mol)을 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-12를 제조하였다.Mix 18.4 g (0.2 mol) of lactic acid (LA) and 10.9 g (0.1 mol) of tetramethylammonium chloride (TMAC) together and heat to 80 °C for 1 hour until the material is completely dissolved. If maintained, a colorless transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-12 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 13> 공융용매의 제조(DES-13)<Example 13> Preparation of eutectic solvent (DES-13)

에틸렌 글리콜(ethylene glycol, EG) 12.4 g (0.2 mol)과 테트라메틸암모늄 클로라이드(tetramethylammonium chloride, TMAC) 10.9 g (0.1 mol)을 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시키면 공융용매 DES-13를 제조하였다.12.4 g (0.2 mol) of ethylene glycol (EG) and 10.9 g (0.1 mol) of tetramethylammonium chloride (TMAC) are mixed together and heated to 80 °C for 1 hour until the material is completely dissolved. If held for a while, a colorless transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-13 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

<실시예 14> 공융용매의 제조(DES-14)<Example 14> Preparation of eutectic solvent (DES-14)

에틸렌 글리콜(ethylene glycol, EG) 12.4 g(0.2 mol)과 우레아(Urea) 6 g (0.1 mol) 테트라메틸암모늄 클로라이드(tetramethylammonium chloride, TMAC) 10.9 g (0.1 mol)과 함께 혼합하고 80 °C로 가열하여 물질이 완전히 용해될 때까지 1시간 동안 유지하면 무색 투명한 액체가 생성된다. 반응이 완전히 끝난 이후, 점도있는 액체를 얻기위해 80°C 오븐에서 12시간동안 건조시켜 공융용매 DES-14를 제조하였다.Mix with ethylene glycol (EG) 12.4 g (0.2 mol) and urea 6 g (0.1 mol) tetramethylammonium chloride (TMAC) 10.9 g (0.1 mol) and heat to 80 °C Thus, if the material is kept for 1 hour until completely dissolved, a colorless and transparent liquid is produced. After the reaction was complete, the eutectic solvent DES-14 was prepared by drying in an oven at 80°C for 12 hours to obtain a viscous liquid.

상기 실시예 1, 2 및 14에서 제조한 3원 공융용매(Ternary deep eutectic solvent)의 조성을 하기 표 1에 나타내었다.The composition of the ternary deep eutectic solvent prepared in Examples 1, 2 and 14 is shown in Table 1 below.

실시예Example HBAHBA HBD 1HBD 1 HBD 2HBD 2 Molar/ratio
(HBA/HBD1/HBD2)
Molar/ratio
(HBA/HBD1/HBD2)
1One ChClChCl EGEG WaterWater 1/2/11/2/1 22 ChClChCl EGEG LALA 1/2/11/2/1 1414 TMACTMAC EGEG UreaUrea 1/2/11/2/1

상기 표에서, HBA는 수소결합수용체(Hydrogen bond acceptor)이고, HBD는 수소결합공여체(Hydrogen bond donor)이다.In the above table, HBA is a hydrogen bond acceptor, and HBD is a hydrogen bond donor.

상기 실시예 3-13에서 제조한 2원 공융용매(Binary deep eutectic solvent)의 조성을 하기 표 2에 나타내었다.The composition of the binary deep eutectic solvent prepared in Example 3-13 is shown in Table 2 below.

실시예Example HBAHBA HBDHBD Molar/ratio
(HBA/HBD)
Molar/ratio
(HBA/HBD)
33 ChClChCl EGEG 1/41/4 44 ChClChCl EGEG 1/31/3 55 ChClChCl EGEG 1/21/2 66 ChClChCl LALA 1/21/2 77 ChClChCl OAOA 1/21/2 88 ChClChCl GLGL 1/21/2 99 ChClChCl BABA 1/21/2 1010 BTBT LALA 1/21/2 1111 TBABTBAB LALA 1/21/2 1212 TMACTMAC LALA 1/11/1 1313 TMACTMAC EGEG 1/21/2

상기 표에서, HBA는 수소결합수용체(Hydrogen bond acceptor)이고, HBD는 수소결합공여체(Hydrogen bond donor)이다.In the above table, HBA is a hydrogen bond acceptor, and HBD is a hydrogen bond donor.

하기 표 3은 하기 실험예에서 사용된 식물체 및 각 식물체로부터 추출한 유효성분을 정리한 것이다.Table 3 below summarizes the plants used in the following experimental examples and the active ingredients extracted from each plant.

식물체Plant 추출 유효성분Extracted active ingredient 오렌지 껍질(Orange peel)
녹차(Green tea) 잎
인진호(Herba Artemisiae Scopariae) 잎
단삼(Salvia miltiorrhiza Bge) 뿌리
은행나무(Ginkgo biloba L.) 잎
인동 덩굴(Lonicera japonica) 줄기
회향(Fennel seed) 씨
바닷말(seaweed) 잎
Orange peel
Green tea leaves
Injinho (Herba Artemisiae Scopariae) leaves
Salvia miltiorrhiza Bge root
Ginkgo biloba L. leaves
Honeysuckle (Lonicera japonica) stem
Fennel seed
Seaweed leaves
<항산화물질>
카페인산(Caffeic acid)
페룰산(Ferulic acid)
루틴(Rutin)
클로로겐산(Chlorogenic acid)
<Antioxidant quality>
Caffeic acid
Ferulic acid
Rutin
Chlorogenic acid
민감초(Liquorice) 뿌리Liquorice root <미백물질>
글라브리딘(Glabridin)
<Whitening substance>
Glabridin

<실험예 1> 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물을 사용한 오렌지 껍질로부터 유효성분의 추출<Experimental Example 1> Extraction of active ingredients from orange peel using an extraction composition for extracting active ingredients from plants containing eutectic solvent

본 발명에 따른 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물의 추출효율을 알아보기 위하여, 실시예 1-14의 조성물을 사용하여 다양한 식물체로부터 유효성분을 추출하였다. 비교예로서, 유기용매인 메탄올을 사용하여 동일한 실험을 수행하였다.In order to examine the extraction efficiency of the extraction composition for extracting the active ingredient from the plant containing the eutectic solvent according to the present invention, the active ingredient was extracted from various plants using the composition of Examples 1-14. As a comparative example, the same experiment was performed using methanol as an organic solvent.

구체적인 추출방법은 다음과 같다.The specific extraction method is as follows.

식물체(녹차잎 , 인진호잎, 단삼뿌리, 은행나무잎, 인동 덩굴 줄기, 회향 씨, 바닷말잎, 민감초뿌리) 0.1g과 실시예 1-13의 공융용매 1ml 를 40 °C, 20rpm에서 30분간 혼합한후 만들어진 혼합물을 filter 0.45(μm)를 부착한 주사기에 넣고 추출물질을 추출한다. 0.1 g of plants (green tea leaves, injinho leaves, sweet ginseng roots, ginkgo leaves, honeysuckle stems, fennel seeds, seaweed leaves, sensitive grass roots) and 1 ml of the eutectic solvent of Example 1-13 at 40 °C and 20 rpm for 30 minutes After mixing, put the prepared mixture into a syringe attached with a filter 0.45 (μm) and extract the extract.

실시예 1-13의 조성물을 추출용매로 사용하여 오렌지 껍질로부터 카페인산, 페룰산 및 루틴을 추출하여, 추출수율을 정리하여 도 1에 나타내었다.Using the composition of Example 1-13 as an extraction solvent, caffeic acid, ferulic acid, and rutin were extracted from orange peel, and the extraction yield was summarized and shown in FIG. 1.

도 1에 나타난 바와 같이,As shown in Figure 1,

본 발명의 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물을 추출용매로 사용하여, 오렌지 껍질로부터 카페인산, 페룰산 및 루틴을 추출할 수 있음을 알 수 있다. 특히, 실시예 13의 조성물은 실시예 중에서 가장 우수한 추출효율을 나타내며, 추출용매로 널리 사용되고 있는 유기용매인 메탄올보다 현저히 우수한 유효성분 추출양을 나타내는 것을 알 수 있다.It can be seen that caffeic acid, ferulic acid, and rutin can be extracted from orange peel by using the composition for extraction for extracting the active ingredient from the plant containing the eutectic solvent of the present invention as an extraction solvent. In particular, it can be seen that the composition of Example 13 exhibits the best extraction efficiency among the examples, and significantly superior extracting amount of active ingredients than methanol, an organic solvent widely used as an extraction solvent.

추출 유효성분 관점에서,In terms of extracting active ingredients,

페룰산은, 실시예 3, 4, 7, 9 및 13의 조성물을 추출용매로 사용할 경우, 10 mg/g이상으로 추출용매로 널리 사용되고 있는 유기용매인 메탄올과 유사한 추출양을 나타냄을 알 수 있으며, 특히, 실시예 13을 사용할 경우, 메탄올보다 높은 추출양을 나타내어, 페룰산의 추출효율이 더 우수함을 알 수 있다.Ferulic acid, when using the compositions of Examples 3, 4, 7, 9, and 13 as an extraction solvent, it can be seen that 10 mg / g or more exhibits an extraction amount similar to methanol, an organic solvent widely used as an extraction solvent, In particular, in the case of using Example 13, the extraction amount was higher than that of methanol, and it was found that the extraction efficiency of ferulic acid was more excellent.

카페인산은, 실시예 2, 3, 4, 8 및 13의 조성물을 추출용매로 사용할 경우, 메탄올보다 높은 추출양을 나타내며, 특히, 실시예 13을 사용할 경우, 메탄올보다 약 1.5배 이상 높은 추출양을 나타내어, 카페인산의 추출효율이 현저하게 우수함을 알 수 있다.Caffeic acid, when using the composition of Examples 2, 3, 4, 8, and 13 as an extraction solvent, exhibits a higher extraction amount than methanol, and in particular, when using Example 13, the extraction amount is about 1.5 times higher than that of methanol. By showing, it can be seen that the extraction efficiency of caffeic acid is remarkably excellent.

루틴은, 실시예 13을 사용할 경우, 메탄올보다 약 1.5배 이상 높은 추출양을 나타내어, 루틴의 추출효율이 현저하게 우수함을 알 수 있다.Rutin, when using Example 13, showed an extraction amount that is about 1.5 times higher than that of methanol, and it can be seen that the extraction efficiency of rutin was remarkably excellent.

<실험예 2> 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물을 사용한 다양한 식물체로부터 유효성분의 추출<Experimental Example 2> Extraction of active ingredients from various plants using an extraction composition for extracting active ingredients from plants containing eutectic solvent

도 1의 결과에서, 카페인산, 페룰산 및 루틴에 전체 대하여 가장 높은 추출효과를 나타내는 추출용매인 실시예 13의 조성물을 사용하여, 오렌지 껍질, 녹차, 인진호, 단삼, 은행나무, 인동 덩굴 및 회향에서 카페인산, 페룰산 및 루틴을 추출하였으며, 실시예 13을 사용한 추출 수율 및 메탄올을 사용하여 추출한 추출수율을 구체적인 수치로 비교하여 하기 표 4에 나타내었다.In the results of FIG. 1, using the composition of Example 13, which is an extraction solvent showing the highest extraction effect with respect to caffeic acid, ferulic acid, and rutin, orange peel, green tea, injinho, dansam, ginkgo, honeysuckle and fennel Caffeic acid, ferulic acid, and rutin were extracted from, and the extraction yield using Example 13 and the extraction yield extracted using methanol were compared with specific values, and are shown in Table 4 below.

또한, 실시예 13을 추출용매로 사용하여 다양한 식물체로부터 클로로젠산을 추출하였으며, 실시예 13을 사용한 추출 수율 및 에탄올을 사용하여 추출한 추출수율을 구체적인 수치로 비교하여 하기 표 5에 나타내었다.In addition, chlorogenic acid was extracted from various plants using Example 13 as an extraction solvent, and the extraction yield using Example 13 and the extraction yield extracted using ethanol were compared with specific values, and are shown in Table 5 below.

또한, 실시예 13 및 14를 추출용매로 사용하여 민감초로부터 글라브리딘을 추출하였으며, 실시예 13 및 14을 사용한 추출 수율 및 에탄올을 사용하여 추출한 추출수율을 구체적인 수치로 비교하여 하기 표 6에 나타내었다.In addition, examples 13 and 14 were used as extraction solvents to extract glabridin from the sensitive weeds, and the extraction yields using Examples 13 and 14 and the extraction yields extracted using ethanol were compared with specific values in Table 6 below. Indicated.

각 실험의 구체적인 실험 방법은 상기 실험예 1과 동일하게 수행하였다.The specific experimental method of each experiment was performed in the same manner as in Experimental Example 1.

추출 수율 (mg/g)Extraction yield (mg/g) 카페인산Caffeic acid 페룰산Ferulic acid 루틴Routine 식물체Plant MeOHMeOH 실시예 13Example 13 MeOHMeOH 실시예 13Example 13 MeOHMeOH 실시예 13Example 13 오렌지 껍질orange peel 1.771.77 3.183.18 11.811.8 12.2412.24 0.750.75 1.291.29 녹차green tea 0.260.26 0.480.48 0.240.24 0.590.59 0.630.63 1.501.50 인진호Jinho In 0.250.25 0.460.46 0.390.39 0.470.47 0.250.25 0.480.48 단삼Dansam 0.170.17 0.280.28 0.410.41 0.840.84 0.560.56 0.620.62 은행나무Ginkgo 1.151.15 1.891.89 0.750.75 1.081.08 1.121.12 1.531.53 바닷말Seahorse 00 00 0.550.55 0.860.86 00 00 인동 덩굴Honeysuckle 0.220.22 0.410.41 0.260.26 0.610.61 0.470.47 0.690.69 회향fennel 0.120.12 0.150.15 00 00 0.130.13 0.180.18

상기 표 4에 나타난 바와 같이,As shown in Table 4 above,

본 발명의 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물은 식물체의 종류에 관계없이, 유효성분을 추출할 수 있음을 알 수 있다. 또한, 추출용매로 널리 사용되고 있는 유기용매인 메탄올보다 현저히 우수한 유효성분 추출양을 나타내는 것을 알 수 있다.It can be seen that the extraction composition for extracting the active ingredient from the plant containing the eutectic solvent of the present invention can extract the active ingredient regardless of the type of the plant. In addition, it can be seen that the extraction amount of the active ingredient is significantly better than methanol, which is an organic solvent widely used as an extraction solvent.

클로로젠산 추출수율 (mg/g)Chlorogenic acid extraction yield (mg/g) 식물체Plant EtOHEtOH 실시예 13Example 13 녹차green tea 0.0920.092 0.170.17 인진호Jinho In 0.490.49 2.202.20 은행나무Ginkgo 0.130.13 0.150.15 인동 덩굴Honeysuckle 0.0850.085 0.0990.099 민감초Sensitive herb 0.880.88 4.34.3 회향fennel 0.110.11 0.230.23 오렌지 껍질orange peel 0.130.13 0.490.49

상기 표 5에 나타난 바와 같이,As shown in Table 5 above,

본 발명의 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물은 식물체의 종류에 관계없이, 유효성분을 추출할 수 있음을 알 수 있다. 또한, 추출용매로 널리 사용되고 있는 유기용매인 에탄올보다 현저히 우수한 유효성분 추출양을 나타내는 것을 알 수 있다.It can be seen that the extraction composition for extracting the active ingredient from the plant containing the eutectic solvent of the present invention can extract the active ingredient regardless of the type of the plant. In addition, it can be seen that the extraction amount of the active ingredient is significantly better than ethanol, which is an organic solvent widely used as an extraction solvent.

추출수율 글라브리딘 (mg/g)Extraction yield Glabridin (mg/g) 식물체Plant EtOHEtOH 실시예 13Example 13 실시예 14Example 14 민감초Sensitive herb 0.100.10 0.0630.063 0.100.10

상기 표 6에 나타난 바와 같이,As shown in Table 6 above,

본 발명의 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물은 민감초로부터 미백물질로 잘 알려진 유효성분인 글라브리딘을 추출할 수 있음을 알 수 있다. 특히, 실시예 13의 경우, 추출용매로 널리 사용되고 있는 유기용매인 에탄올보다 현저히 우수한 유효성분 추출양을 나타내는 것을 알 수 있다.It can be seen that the extraction composition for extracting the active ingredient from the plant containing the eutectic solvent of the present invention can extract the active ingredient glabridin, which is well known as a whitening substance, from the sensitive herb. Particularly, in the case of Example 13, it can be seen that the extraction amount of the active ingredient is significantly better than ethanol, which is an organic solvent widely used as an extraction solvent.

상술한 바와 같이,As mentioned above,

본 발명에 따른 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물은 간단한 제조공정으로 쉽게 제조할 수 있으며, 반응과정에서 추가적인 유기용제를 사용할 필요가 없으며, 유기용매를 사용하지 않음에 따라, 독성물질 방출 및 부산물이 없어 환경오염 물질 배출이 적을 것으로 기대된다. 또한, 다양한 식물체로부터 유효성분을 우수한 순도 및 수율로 추출할 수 있다.The extraction composition for extracting the active ingredient from the plant containing the eutectic solvent according to the present invention can be easily prepared by a simple manufacturing process, and there is no need to use an additional organic solvent in the reaction process, and the organic solvent is not used. Accordingly, it is expected that there will be little emission of environmental pollutants because there is no emission of toxic substances or by-products. In addition, active ingredients can be extracted from various plants with excellent purity and yield.

이에, 본 발명에 따른 공융용매를 포함하는 식물체로부터 유효성분을 추출하기 위한 추출용 조성물은 종래 유기용매의 추출용매를 대체하는 친환경적이고 경제적인 추출용매로 유용하게 사용될 수 있다.Accordingly, the extraction composition for extracting an active ingredient from a plant containing the eutectic solvent according to the present invention can be usefully used as an eco-friendly and economical extraction solvent replacing the extraction solvent of the conventional organic solvent.

Claims (10)

오렌지 껍질(Orange peel), 녹차(Green tea), 인진호(Herba Artemisiae Scopariae), 단삼(Salvia miltiorrhiza Bge), 은행나무(Ginkgo biloba L.), 인동 덩굴(Lonicera japonica), 회향(Fennel seed) 및 바닷말(seaweed) 로 이루어지는 군으로부터 선택되는 어느하나인 식물체를 준비하는 단계; 및
에틸렌 글리콜(ethylene glycol, EG)인 수소결합공여체(Hydrogen bond donor, HBD); 및 테트라메틸암모늄 클로라이드(tetramethylammonium chloride, TMAC)인 수소결합수용체(Hydrogen bond acceptor, HBA)의 혼합으로 구성되는 공융용매로 이루어진 추출용매 및 상기 식물체를 혼합하여 유효성분을 추출하는 단계를 포함하며,
상기 유효성분은 카페인산(Caffeic acid), 페룰산(Ferulic acid), 루틴(Rutin) 및 클로로겐산(Chlorogenic acid)으로 이루어지는 폴리페놀 화합물로부터 선택되는 하나 이상인 것을 특징으로 하는 식물체로부터 유효성분을 추출하는 방법.
Orange peel, Green tea, Herba Artemisiae Scopariae, Salvia miltiorrhiza Bge, Ginkgo biloba L., Lonicera japonica, Fennel seed and sea horse (seaweed) preparing any one plant selected from the group consisting of; And
Hydrogen bond donor (HBD), which is ethylene glycol (EG); And extracting an active ingredient by mixing an extraction solvent consisting of a eutectic solvent composed of a mixture of a hydrogen bond acceptor (HBA), which is tetramethylammonium chloride (TMAC), and the plant,
The active ingredient is at least one selected from polyphenol compounds consisting of caffeic acid, ferulic acid, rutin, and chlorogenic acid. .
삭제delete 삭제delete 삭제delete 삭제delete 제1항에 있어서,
상기 수소결합수용체(Hydrogen bond acceptor, HBA) 1몰농도(Molar)에 대하여 수소결합공여체(Hydrogen bond donor, HBD)를 1 내지 4몰농도로 포함하는 것을 특징으로 하는 식물체로부터 유효성분을 추출하는 방법.
The method of claim 1,
A method for extracting an active ingredient from a plant comprising 1 to 4 molar concentrations of a hydrogen bond donor (HBD) to 1 molar concentration of the hydrogen bond acceptor (HBA) .
삭제delete 삭제delete 삭제delete 제1항에 있어서,
상기 추출은 초음파 처리(Ultra sonic), 디핑(Dipping) 및 환류(Reflux)로 이루어지는 군으로부터 선택되는 1 종의 방법을 통해 수행되는 것을 특징으로 하는 식물체로부터 유효성분을 추출하는 방법.
The method of claim 1,
The extraction method for extracting an active ingredient from a plant, characterized in that it is carried out through one type of method selected from the group consisting of ultrasonic treatment (Ultra sonic), dipping (Dipping) and reflux (Reflux).
KR1020180135363A 2018-11-06 2018-11-06 A Composition for extracting effective ingredients from plant comprising deep eutectic solvent and a method for extracting effective ingredients from plant using the same KR102229831B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020180135363A KR102229831B1 (en) 2018-11-06 2018-11-06 A Composition for extracting effective ingredients from plant comprising deep eutectic solvent and a method for extracting effective ingredients from plant using the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020180135363A KR102229831B1 (en) 2018-11-06 2018-11-06 A Composition for extracting effective ingredients from plant comprising deep eutectic solvent and a method for extracting effective ingredients from plant using the same

Publications (2)

Publication Number Publication Date
KR20200052147A KR20200052147A (en) 2020-05-14
KR102229831B1 true KR102229831B1 (en) 2021-03-18

Family

ID=70737262

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020180135363A KR102229831B1 (en) 2018-11-06 2018-11-06 A Composition for extracting effective ingredients from plant comprising deep eutectic solvent and a method for extracting effective ingredients from plant using the same

Country Status (1)

Country Link
KR (1) KR102229831B1 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102497134B1 (en) * 2020-10-28 2023-02-06 한상철 Deep eutectic solvent for extracting cosmetic ingredients and method for extracting cosmetic ingredients using the same
CN113907156A (en) * 2021-11-18 2022-01-11 中国农业科学院都市农业研究所 Preparation method of theabrownin and antioxidant component thereof
CN116251137B (en) * 2021-12-09 2024-01-30 北京农学院 Method for extracting flavonoid compounds from caulis spatholobi
CN114181328B (en) * 2021-12-16 2022-11-01 季华实验室 Method for extracting beta-chitin from squid cartilage
KR102428817B1 (en) * 2022-01-25 2022-08-02 단국대학교 천안캠퍼스 산학협력단 Method for extracting active ingredients from citrus grandis osbeck
KR102435822B1 (en) * 2022-03-22 2022-08-23 단국대학교 천안캠퍼스 산학협력단 Method for extracting active ingredients from Citrus grandis osbeck
CN114657226A (en) * 2022-04-08 2022-06-24 南京工业大学 Method for extracting flavonoid compounds from licorice residue and utilizing extracted residue
CN115193099B (en) * 2022-08-03 2023-11-07 广东省农业科学院环境园艺研究所 Method for extracting sphagnum active ingredient by using eutectic solvent
CN115154404B (en) * 2022-09-06 2022-11-11 广东迪美新材料科技有限公司 Plant composition with tightening and anti-aging effects and preparation method and application thereof
CN116251044A (en) * 2022-12-29 2023-06-13 广州梵之容化妆品有限公司 Eutectic glabridin solution and preparation method and application thereof
CN116059309B (en) * 2023-04-06 2023-06-30 江西中医药大学 Essential oil composition and preparation method thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101576232B1 (en) * 2013-12-17 2015-12-09 인하대학교 산학협력단 Extraction method for rosmarinic acid and caffeic acid in zostera marinia
KR101901451B1 (en) 2018-01-23 2018-09-27 (주)해피엘앤비 Cosmetic composition containing flower extracts prepared by a method based on natural deep eutectic Solvents

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3034625A1 (en) * 2015-04-10 2016-10-14 Naturex EUTECTIC EXTRACTION SOLVENT, EUTECTIGENESE EXTRACTION METHOD USING THE SOLVENT, AND EXTRACT FROM THE EXTRACTION PROCESS.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101576232B1 (en) * 2013-12-17 2015-12-09 인하대학교 산학협력단 Extraction method for rosmarinic acid and caffeic acid in zostera marinia
KR101901451B1 (en) 2018-01-23 2018-09-27 (주)해피엘앤비 Cosmetic composition containing flower extracts prepared by a method based on natural deep eutectic Solvents

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Cleaner Production 152. 399-405
Sustainable Chemistry and Engineering 5. 3270-3278

Also Published As

Publication number Publication date
KR20200052147A (en) 2020-05-14

Similar Documents

Publication Publication Date Title
KR102229831B1 (en) A Composition for extracting effective ingredients from plant comprising deep eutectic solvent and a method for extracting effective ingredients from plant using the same
JP5269160B2 (en) Bioactive liquid composition and method for producing the same
SWATIą et al. Moringa oleifera—A never die tree: An overview
CN101003775A (en) Method for producing health protection tea wine of ampelopsis grossedentata, and product
CN101496529A (en) Camellia oleifera environment-friendly pesticide
KR20110053235A (en) Method for producing a composition with a high content of sapogenin
CN110882329A (en) Belladonna liquid extract production process
CN107811924A (en) A kind of mouthwash and preparation method thereof
CN107670463A (en) It can sterilize, absorb formaldehyde and absorb the automobile air purifying agent of haze
KR20180119772A (en) Method for preparing extract of nipa fruticans and nipa fruticans extract thereby
CN108402095A (en) A kind of bactericide of prevention pest and disease damage
CN1921871A (en) Physiologically active composition and process for producing the same
CN103222469B (en) Method for producing sophocarpidine water aqua by using enzymolysis method
KR20190029851A (en) Pharmaceutical compositions comprising Quercetin and true Angelica gigas Nakai extract and methods for their preparation
KR101817704B1 (en) eco-friendly composition for controlling plant viruses
CN104739904B (en) A kind of method that sugar-lowering components are extracted from Leaves of Hippophae L
CN101024802B (en) Pine-juice beer and its brewing method
KR101896952B1 (en) Natural antibacterial composition using food by-product and method for manufacturing the same
KR20150029672A (en) My skin health and beauty using the functional bio-ceramic and 107 kinds of native grasses
KR101814033B1 (en) Grain syrup comprising astragalus membranaceus and manufacturing method thereof
CN107500863A (en) A kind of wine-growing Liquid Fertilizer and preparation method thereof
CN115769825A (en) Preparation method of high-content ginkgolic acid plant source pesticide
CN106577829A (en) Plant composition for black spot disease of Stevia rebaudiana and preparation method thereof
CN111587883A (en) Plant pesticide and preparation method and use method thereof
CN110692656A (en) Preparation method of plant-derived pesticide and plant-derived pesticide

Legal Events

Date Code Title Description
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant