KR102302072B1 - Method for producing fermented Beta vulgaris extract with improved antioxidant activity and fermented Beta vulgaris extract produced by the same method - Google Patents
Method for producing fermented Beta vulgaris extract with improved antioxidant activity and fermented Beta vulgaris extract produced by the same method Download PDFInfo
- Publication number
- KR102302072B1 KR102302072B1 KR1020190156837A KR20190156837A KR102302072B1 KR 102302072 B1 KR102302072 B1 KR 102302072B1 KR 1020190156837 A KR1020190156837 A KR 1020190156837A KR 20190156837 A KR20190156837 A KR 20190156837A KR 102302072 B1 KR102302072 B1 KR 102302072B1
- Authority
- KR
- South Korea
- Prior art keywords
- fermented
- extract
- beet
- antioxidant activity
- hydroxymaltol
- Prior art date
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Abstract
본 발명은 5-히드록시말톨을 함유하는 항산화 활성이 증진된 비트 발효 추출물의 제조방법 및 상기 방법으로 제조된 비트 발효 추출물에 관한 것으로, 본 발명의 비트 발효 추출물은 비트 비발효 추출물에 비해 5-히드록시말톨을 함유하여 항산화 활성이 우수하므로 항산화용 건강기능식품 및 화장품의 소재로 유용하게 사용될 수 있다.The present invention relates to a method for preparing a fermented beet extract with enhanced antioxidant activity containing 5-hydroxymaltol and to a fermented beet extract prepared by the method, wherein the fermented beet extract of the present invention contains 5-hydroxymaltol compared to a non-fermented beet extract. Since it contains hydroxymaltol and has excellent antioxidant activity, it can be usefully used as a material for antioxidant health functional foods and cosmetics.
Description
본 발명은 항산화 활성이 증진된 비트 발효 추출물의 제조방법 및 상기 방법으로 제조된 비트 발효 추출물에 관한 것이다.The present invention relates to a method for producing a fermented beetroot extract with enhanced antioxidant activity, and to a fermented beetroot extract prepared by the method.
활성산소는 자연계에 널리 존재하는 안정한 분자상태인 기저 삼중항 산소로부터 효소계, 환원대사과정, 화학적 약품, 공해물질 및 광화학적 반응 등에 의하여 생성되며, 그 생성물로는 슈퍼옥사이드(superoxide), 과산화수소(hydrogen peroxide), 수산화 라디칼(hydroxyl radical), 일중항 산소(singlet oxygen) 등이 있다. 활성산소는 생체 내에서 대식세포의 살균작용, 오래된 단백질의 제거 등에 이용되는 필수적인 물질이지만 반응성이 커서 생체 내에서 유해한 반응을 나타낼 수 있기 때문에 활성산소가 지나치게 증가되었을 경우에는 생체 내의 각 부위에 치명적인 손상을 일으키기도 한다. 이로 인해 암을 비롯한 뇌졸중, 심장질환, 피부질환, 소화기 질환, 염증, 류마티스, 자기면역질환 등의 각종 질병 및 노화를 일으키는 것으로 알려져 있다.Active oxygen is produced by enzyme system, reduction metabolic process, chemical agent, pollutant and photochemical reaction from basal triplet oxygen, which is a stable molecular state widely present in nature, and the products include superoxide and hydrogen peroxide. peroxide), hydroxyl radical, and singlet oxygen. Although active oxygen is an essential substance used for sterilization of macrophages and removal of old proteins in the living body, it is highly reactive and can cause harmful reactions in the living body. also cause Due to this, it is known to cause various diseases such as cancer, stroke, heart disease, skin disease, digestive disease, inflammation, rheumatism, autoimmune disease, and aging and aging.
생체 내 항산화 방어시스템을 증가시키거나 활성산소종을 조절할 수 있는 항산화제로는 토코페롤류, BHT(butylatedhydroxytoluene), BHA(butylated hydroxyanisole), 프로필갈레이트(propyl gallate), TBHQ(tertiarybutyl hydroquinone), 아스코르브산 등이 있다. 상대적으로 항산화 효과가 뛰어난 합성 산화제인 BHT와 BHA는 우수한 효능과 저렴한 가격 때문에 토코페롤이나 비타민 C 보다 널리 사용되고 있으나, 합성산화제는 체내의 에너지 생산, 세포대사 및 호흡작용을 방해하며 발암성의 강한 독성을 가진 것으로 알려진 바 있다. 이에 최근에는 인체에 부작용이 없는 식물에서 추출된 소재를 이용하여 독성을 감소시키면서도 항산화 효과를 증진시키기 위한 연구가 지속되고 있다.Antioxidants that can increase the antioxidant defense system in vivo or control reactive oxygen species include tocopherols, BHT (butylated hydroxytoluene), BHA (butylated hydroxyanisole), propyl gallate, TBHQ (tertiarybutyl hydroquinone), ascorbic acid, etc. There is this. BHT and BHA, which are synthetic oxidizers with relatively excellent antioxidant effects, are more widely used than tocopherol or vitamin C because of their excellent efficacy and low price. has been known to In recent years, research to enhance the antioxidant effect while reducing toxicity by using a material extracted from a plant that does not have side effects on the human body is continuing.
비트(Beta vulgaris)는 근공채, 홍채두, 화염채라고도 불리며, 지중해 연안의 남부 유럽과 북아프리카가 원산지이다. 비교적 재배가 쉽고 식물체 전체를 사용할 수 있어 외국에서는 집에서 손쉽게 재배하는 인기작물이다. 국내에서는 주로 경기도 이천, 강원도 평창 및 제주도에서 생산되고 있으며, 빨간색 뿌리는 우리나라 강화 순무와 비슷하다. 비트의 8%는 염소로 구성되어 있는데, 이 염소 성분은 간 정화 작용을 하고 골격 형성 및 유아 발육에 효과가 있다. 또한, 철분과 비타민이 다량 함유되어 있어 적혈구 생성을 돕고, 혈액을 맑게 하여 혈액순환이 원활하도록 도와주어 혈액순환장애를 개선시켜주는 효과가 있으며, 월경불순이나 갱년기 여성에게 좋은 것으로 알려져 있다. 또한, 비트는 위 손상을 막아주고 위 점막을 보호해 줄 뿐만 아니라 노화, 빈혈, 스트레스, 시력회복, 세포복제기능, 해독작용 등에도 효과가 있다고 알려져 있다.Beta ( Beta vulgaris ) is also called geungongchae, irisdu, flamingchae, and is native to southern Europe and North Africa along the Mediterranean coast. Since it is relatively easy to cultivate and the whole plant can be used, it is a popular crop that is easily cultivated at home in foreign countries. In Korea, it is mainly produced in Icheon, Gyeonggi-do, Pyeongchang, Gangwon-do, and Jeju-do. The red root is similar to that of Ganghwa turnip in Korea. 8% of beets are composed of chlorine, and this chlorine component has a liver purifying effect and is effective for bone formation and infant development. In addition, since it contains a large amount of iron and vitamins, it aids in the production of red blood cells, purifies the blood and improves blood circulation, thereby improving blood circulation disorders. In addition, beets are known to be effective not only in preventing gastric damage and protecting the gastric mucosa, but also in aging, anemia, stress, vision recovery, cell replication function, and detoxification.
한편, 한국등록특허 제1922724호에는 '비트 발효물을 포함한 건강 보조 식품 조성물 및 이의 제조방법'이 개시되어 있고, 한국등록특허 제1682156호에는 '레드비트 추출물을 이용한 방사선에 의한 면역조혈기능 장해 방호용 조성물'이 개시되어 있으나, 본 발명의 항산화 활성이 증진된 비트 발효 추출물의 제조방법 및 상기 방법으로 제조된 비트 발효 추출물에 대해서는 기재된 바가 없다.On the other hand, Korean Patent No. 1922724 discloses 'Health supplement composition including fermented beetroot and manufacturing method thereof', and Korean Patent No. 1682156 discloses 'Protection of immune-hematopoietic function disorder due to radiation using red beet extract. 'Composition for use' is disclosed, but there is no description of the method for producing a fermented beet extract with enhanced antioxidant activity of the present invention and the fermented beet extract prepared by the method.
본 발명은 상기와 같은 요구에 의해 도출된 것으로서, 본 발명자들은 비트 분말에 락토바실러스 람노서스(Lactobacillus rhamnosus)를 접종하고 5일간 진탕배양하여 발효시킨 후 에틸 아세테이트(ethyl acetate)를 이용하여 비트 발효 추출물을 제조하였으며, 상기 제조된 비트 발효 추출물이 비트 비발효 추출물에 비해 항산화 활성이 우수함을 확인하였다. 또한, 상기 제조된 비트 발효 추출물을 대상으로 ODS 크로마토그래피, Silica gel 크로마토그래피, Sephadex G-10 크로마토그래피, 분리용 ODS C18 TLC 크로마토그래피 및 HPLC를 순차적으로 진행하여 비트 발효 추출물로부터 5-히드록시말톨(hydroxymaltol)을 분리·정제하였으며, 상기 5-히드록시말톨의 항산화 활성이 우수함을 확인함으로써, 본 발명을 완성하였다.The present invention has been derived by the above requirements, and the present inventors inoculated Lactobacillus rhamnosus into beet powder, cultured with shaking for 5 days and fermented, and then fermented beetroot using ethyl acetate. was prepared, and it was confirmed that the prepared fermented beet extract had superior antioxidant activity compared to the non-fermented beet extract. In addition, 5-hydroxymaltol from the beet ferment extract was sequentially subjected to ODS chromatography, silica gel chromatography, Sephadex G-10 chromatography, ODS C18 TLC chromatography and HPLC for the prepared beet ferment extract. (hydroxymaltol) was isolated and purified, and the present invention was completed by confirming that 5-hydroxymaltol had excellent antioxidant activity.
상기 과제를 해결하기 위해, 본 발명은 (1) 액체 배지에 비트 분말을 첨가하고 멸균하여 비트 발효용 배지를 제조하는 단계; (2) 상기 (1) 단계의 비트 발효용 배지에 유산균 배양액을 접종하고 배양하여 발효시킨 후 원심분리하여 상등액을 수득하는 단계; 및 (3) 상기 (2) 단계의 상등액과 추출용매를 혼합하여 추출하는 단계;를 포함하여 제조하는 것을 특징으로 하는 5-히드록시말톨을 함유하는 항산화 활성이 증진된 비트 발효 추출물의 제조방법을 제공한다.In order to solve the above problems, the present invention comprises the steps of (1) adding beet powder to a liquid medium and sterilizing to prepare a medium for fermentation of beets; (2) inoculating the lactic acid bacteria culture medium in the beet fermentation medium of step (1), culturing and fermenting, followed by centrifugation to obtain a supernatant; and (3) mixing and extracting the supernatant of the step (2) and an extraction solvent; to provide.
또한, 본 발명은 상기 방법으로 제조된, 5-히드록시말톨(hydroxymaltol)을 함유하는 항산화 활성이 증진된 비트 발효 추출물을 제공한다.In addition, the present invention provides a fermented beetroot extract with enhanced antioxidant activity containing 5-hydroxymaltol, prepared by the above method.
또한, 본 발명은 상기 5-히드록시말톨(hydroxymaltol)을 함유하는 항산화 활성이 증진된 비트 발효 추출물을 유효성분으로 함유하는 항산화용 건강기능식품 및 화장료 조성물을 제공한다.In addition, the present invention provides a health functional food and cosmetic composition for antioxidants containing, as an active ingredient, the fermented beetroot extract with enhanced antioxidant activity containing the 5-hydroxymaltol.
본 발명의 비트 발효 추출물은 발효 과정에 의해 우수한 항산화 활성을 가지는 5-히드록시말톨이 새롭게 생성되어 항산화 활성이 우수하므로, 항산화용 식품 및 화장료 조성물 개발에 유용하게 활용될 수 있을 것이다.The fermented beet extract of the present invention has excellent antioxidant activity as 5-hydroxymaltol having excellent antioxidant activity is newly generated by the fermentation process, so it may be usefully used in the development of food and cosmetic compositions for antioxidants.
도 1은 비트 비발효 추출물(대조군) 및 비트 발효 추출물의 ABTS 라디칼 소거능(A) 및 DPPH 라디칼 소거능(B)을 확인한 결과이다.
도 2는 HPLC(high pressure liquid chromatography)를 이용하여 비트 비발효 추출물 및 비트 발효 추출물을 분석한 결과이다. 빨간색 네모는 발효 처리된 비트 에서 새롭게 생성된 물질의 피크에 해당된다.
도 3 내지 도 5는 비트 발효 추출물에서 생성된 물질을 정제하기 위해 크로마토그래피를 수행한 결과이다. 도 3A는 ODS C18 오픈컬럼을 이용한 크로마토그래피 결과이고; 도 3B는 실리카겔 크로마토그래피(silical gel choromatography) 결과로, 도 3B-a는 ODS C18 오픈컬럼 결과를 실리카겔 플레이트로 확인한 결과이고 도 3B-b는 실리카겔 크로마토그래피 결과를 실리카겔 플레이트로 확인한 결과이다. 도 4A는 Sephadex G-10 컬럼을 이용한 크로마토그래피(a) 결과와 실리카겔 플레이트 및 ODS C18 플레이트를 이용한 크로마토그래피(b) 결과이고, 도 4B는 분리용 ODS C18 플레이트를 이용한 Prep C18 TLC(thin layer chromatyography 결과이며, 도 5는 Prep HPLC를 이용한 물질의 정제 결과(A) 및 정제 물질을 실리카겔 플레이트를 이용하여 확인한 결과(B)이다.
도 6 및 도 7은 비트 발효 추출물에서 정제된 물질의 구조를 분석한 결과로, 도 6은 1차원 NMR(H-NMR, A; 및 C-NMR, B) 분석을 수행한 결과이고, 도 7은 2차원 NMR(HMBC, A; 및 HMQC, B)을 수행한 결과이다.
도 8은 ESI-질량분석기기(Mass spectophotometer)를 이용하여 비트 발효 추출물에서 정제된 물질의 분자량을 측정한 결과이다.
도 9는 비트 발효 추출물로부터 분리·정제된 5-히드록시말톨(hydroxymaltol)의 DPPH 라디칼 소거능을 확인한 결과이다. 1 is a result of confirming the ABTS radical scavenging ability (A) and DPPH radical scavenging ability (B) of the non-fermented beet extract (control group) and the fermented beet extract.
2 is a result of analyzing a non-fermented beet extract and a fermented beet extract using high pressure liquid chromatography (HPLC). The red squares correspond to the peaks of newly formed substances in fermented beets.
3 to 5 are results of chromatography to purify the material produced from the beet ferment extract. 3A is a chromatography result using an ODS C18 open column; Figure 3B is a result of silica gel chromatography (silical gel choromatography), Figure 3B-a is the result of confirming the ODS C18 open column result with a silica gel plate, Figure 3B-b is the result of confirming the result of silica gel chromatography with a silica gel plate. 4A is a chromatography (a) result using a Sephadex G-10 column and a chromatography (b) result using a silica gel plate and an ODS C18 plate, and FIG. 4B is a Prep C18 thin layer chromatography (TLC) using an ODS C18 plate for separation. Results, Figure 5 shows the results of purification of the material using Prep HPLC (A) and the results of confirming the purified material using a silica gel plate (B).
6 and 7 are the results of analyzing the structure of the material purified from the beet ferment extract, FIG. 6 is the result of performing one-dimensional NMR (H-NMR, A; and C-NMR, B) analysis, FIG. is the result of performing two-dimensional NMR (HMBC, A; and HMQC, B).
8 is a result of measuring the molecular weight of a substance purified from a beet ferment extract using an ESI-mass spectophotometer.
9 is a result confirming the DPPH radical scavenging ability of 5-hydroxymaltol separated and purified from a beet ferment extract.
본 발명의 목적을 달성하기 위하여, 본 발명은In order to achieve the object of the present invention, the present invention
(1) 액체 배지에 비트 분말을 첨가하고 멸균하여 비트 발효용 배지를 제조하는 단계;(1) adding beet powder to a liquid medium and sterilizing to prepare a medium for fermentation of beets;
(2) 상기 (1) 단계의 비트 발효용 배지에 유산균 배양액을 접종하고 배양하여 발효시킨 후 원심분리하여 상등액을 수득하는 단계; 및(2) inoculating the lactic acid bacteria culture medium in the beet fermentation medium of step (1), culturing and fermenting, followed by centrifugation to obtain a supernatant; and
(3) 상기 (2) 단계의 상등액과 추출용매를 혼합하여 추출하는 단계;를 포함하여 제조하는 것을 특징으로 하는 5-히드록시말톨을 함유하는 항산화 활성이 증진된 비트 발효 추출물의 제조방법을 제공한다.(3) providing a method for producing a beet ferment extract with enhanced antioxidant activity containing 5-hydroxymaltol, characterized in that it comprises; (3) mixing and extracting the supernatant from step (2) do.
본 발명의 일 구현 예에 따른 방법에 있어서, 상기 (1) 단계의 비트 발효용 배지는, 바람직하게는 액체배지에 비트 분말 0.5~1.5%(w/v)를 첨가하고 멸균하여 제조할 수 있고, 더욱 바람직하게는 액체배지에 비트 분말 1%(w/v)을 첨가하고 멸균하여 제조할 수 있으나, 이에 제한되지 않는다. In the method according to an embodiment of the present invention, the medium for fermentation of beets in step (1) may be prepared by adding 0.5 to 1.5% (w/v) of beet powder to the liquid medium and sterilizing, preferably, , More preferably, it may be prepared by adding 1% (w/v) of beet powder to the liquid medium and sterilizing, but is not limited thereto.
또한, 상기 액체배지는 MRS 배지일 수 있으나, 이에 한정되지 않으며, 상기 배지 외에 유산균 배양에 사용될 수 있는 다양한 상업 배지가 사용될 수 있다.In addition, the liquid medium may be an MRS medium, but is not limited thereto, and in addition to the medium, various commercial mediums that can be used for culturing lactic acid bacteria may be used.
본 발명의 일 구현 예에 따른 방법에 있어서, 상기 (2) 단계의 유산균은 바람직하게는 락토바실러스 람노서스(Lactobacillus rhamnosus)일 수 있고, 더 바람직하게는 6×105~8×105 CFU/㎖ 농도의 락토바실러스 람노서스(Lactobacillus rhamnosus) GG일 수 있으며, 더 더욱 바람직하게는 7×105 CFU/㎖ 농도의 락토바실러스 람노서스 GG(한국생명공학연구원 생물자원센터, KCTC)일 수 있으나, 이에 제한되지 않는다. In the method according to an embodiment of the present invention, the lactic acid bacteria of step (2) may preferably be Lactobacillus rhamnosus , and more preferably 6×10 5 to 8×10 5 CFU/ ㎖ concentration of Lactobacillus rhamnosus ( Lactobacillus rhamnosus ) It may be GG, and more preferably, it may be Lactobacillus rhamnosus GG (Korea Research Institute of Bioscience and Biotechnology, KCTC) at a concentration of 7×10 5 CFU/ml, but is not limited thereto.
또한, 본 발명의 일 구현 예에 따른 방법에 있어서, 상기 (2) 단계의 발효는 바람직하게는 상기 (1) 단계의 비트 발효용 배지에 락토바실러스 람노서스 배양액을 0.5~1.5%(v/v)로 첨가한 후 28~32℃에서 4~6일 동안 진탕배양하여 발효하는 것일 수 있고, 더욱 바람직하게는 비트 발효용 배지에 락토바실러스 람노서스 배양액을 1%(v/v)로 첨가한 후 30℃에서 5일 동안 진탕배양하여 발효하는 것일 수 있으나, 이에 제한되지 않는다. In addition, in the method according to an embodiment of the present invention, the fermentation of step (2) is preferably 0.5 to 1.5% (v / v) of Lactobacillus rhamnosus culture medium in the medium for fermentation of beets of step (1). ) may be fermented by shaking culture at 28 to 32 ° C for 4 to 6 days, more preferably after adding the Lactobacillus rhamnosus culture solution to the medium for beet fermentation at 1% (v / v) It may be fermented by shaking culture at 30° C. for 5 days, but is not limited thereto.
본 발명의 일 구현 예에 따른 방법에 있어서, 상기 (3) 단계의 추출용매는 물, 탄소수 1 내지 4의 저급 알코올, 에틸 아세테이트, 아세톤, 부틸 아세테이트 및 1,3-부틸렌 글리콜 중에서 선택된 하나 이상의 용매를 이용하여 추출한 것일 수 있으며, 바람직하게는 에틸 아세테이트를 이용하여 추출한 것일 수 있으나, 이에 제한되지 않는다.In the method according to an embodiment of the present invention, the extraction solvent in step (3) is at least one selected from water, a lower alcohol having 1 to 4 carbon atoms, ethyl acetate, acetone, butyl acetate, and 1,3-butylene glycol. It may be extracted using a solvent, preferably, may be extracted using ethyl acetate, but is not limited thereto.
본 발명의 일 구현 예에 따른 방법에 있어서, 상기 5-히드록시말톨을 함유하는 항산화 활성이 증진된 비트 발효 추출물의 제조방법은, 보다 구체적으로는In the method according to an embodiment of the present invention, the method for producing a beet ferment extract with enhanced antioxidant activity containing 5-hydroxymaltol, more specifically
(1) 액체 배지에 비트 분말 0.5~1.5%(w/v)를 첨가하고 멸균하여 비트 발효용 배지를 제조하는 단계;(1) adding 0.5 to 1.5% (w/v) of beet powder to a liquid medium and sterilizing to prepare a medium for fermentation of beets;
(2) 상기 (1) 단계의 비트 발효용 배지에 6×105~8×105 CFU/㎖ 농도의 락토바실러스 람노서스 GG 균주 배양액을 0.5~1.5%(v/v)로 접종하고 28~32℃에서 4~6일 동안 진탕배양하여 발효시킨 후 원심분리하여 상등액을 수득하는 단계; 및(2) Inoculate the culture medium of the beetroot fermentation of step (1) at 0.5-1.5% (v/v) with a Lactobacillus rhamnosus GG strain culture of 6×10 5 ~ 8×10 5 CFU/ml concentration, and 28- After fermenting by shaking culture at 32 ° C. for 4 to 6 days, centrifugation to obtain a supernatant; and
(3) 상기 (2) 단계의 상등액과 에틸 아세테이트 용매를 동량으로 혼합하여 추출하는 단계;를 포함할 수 있고, (3) extracting the supernatant of the step (2) by mixing the same amount with the ethyl acetate solvent;
더욱 구체적으로는,More specifically,
(1) 액체 배지에 비트 분말 1%(w/v)를 첨가하고 멸균하여 비트 발효용 배지를 제조하는 단계;(1) adding 1% (w/v) of beet powder to a liquid medium and sterilizing to prepare a medium for fermentation of beets;
(2) 상기 (1) 단계의 비트 발효용 배지에 7×105 CFU/㎖ 농도의 락토바실러스 람노서스 GG 균주 배양액을 1%(v/v)로 접종하고 30℃에서 5일 동안 진탕배양하여 발효시킨 후 원심분리하여 상등액을 수득하는 단계; 및(2) Inoculated with 1% (v/v) Lactobacillus rhamnosus GG strain culture medium at a concentration of 7×10 5 CFU/ml in the beet fermentation medium of step (1) and cultured with shaking at 30° C. for 5 days After fermentation, centrifugation to obtain a supernatant; and
(3) 상기 (2) 단계의 상등액과 에틸 아세테이트 용매를 동량으로 혼합하여 추출하는 단계;를 포함할 수 있으나, 이에 제한되지 않는다.(3) extracting the supernatant of the step (2) by mixing the same amount with the ethyl acetate solvent; but is not limited thereto.
본 발명은 또한, 본 발명의 상기 제조방법으로 제조된, 5-히드록시말톨(hydroxymaltol)을 함유하는 항산화 활성이 증진된 비트 발효 추출물을 제공한다. 상기 비트 발효 추출물에는 비트 비발효 추출물에 함유되어 있지 않던 5-히드록시말톨(hydroxymaltol)이 새롭게 생성되었으며, 비트 발효 추출물로부터 분리·정제된 5-히드록시말톨은 DPPH 라디칼 소거능이 우수한 특징이 있다.The present invention also provides a fermented beetroot extract with enhanced antioxidant activity, containing 5-hydroxymaltol, prepared by the method of the present invention. In the fermented beet extract, 5-hydroxymaltol, which was not contained in the non-fermented beet extract, was newly generated, and 5-hydroxymaltol separated and purified from the fermented beet extract has an excellent DPPH radical scavenging ability.
본 발명은 또한, 상기 5-히드록시말톨(hydroxymaltol)을 함유하는 항산화 활성이 증진된 비트 발효 추출물을 유효성분으로 함유하는 항산화용 건강기능식품 조성물을 제공한다.The present invention also provides a health functional food composition for antioxidants containing, as an active ingredient, the fermented beetroot extract with enhanced antioxidant activity containing the 5-hydroxymaltol.
본 발명의 건강기능식품 조성물에 있어서, 상기 비트 발효 추출물은 전술한 것과 같다. In the health functional food composition of the present invention, the fermented beet extract is the same as described above.
본 발명의 건강기능식품 조성물에서, 상기 비트 발효 추출물은 비트 비발효 추출물에 비해 라디칼 소거능이 증가하였고, 5-히드록시말톨(hydroxymaltol) 성분이 새롭게 생성되어 항산화 활성이 우수하다.In the health functional food composition of the present invention, the fermented beet extract has an increased radical scavenging ability compared to the non-fermented beet extract, and 5-hydroxymaltol component is newly generated and thus has excellent antioxidant activity.
상기 항산화용 건강기능식품 조성물은 분말, 과립, 환, 정제, 캡슐, 캔디, 시럽, 발포정 및 음료 중에서 선택된 어느 하나의 제형으로 제조될 수 있으나, 이에 제한되지 않는다. 상기 건강기능식품 조성물은 항산화 활성을 증가시키기 위해 섭취할 수 있는 것이면 특별히 제한되지 않는다.The antioxidant health functional food composition may be prepared in any one formulation selected from powder, granule, pill, tablet, capsule, candy, syrup, effervescent tablet and beverage, but is not limited thereto. The health functional food composition is not particularly limited as long as it can be ingested to increase antioxidant activity.
본 발명의 비트 발효 추출물을 식품첨가물로 사용하는 경우, 상기 비트 발효 추출물을 그대로 첨가하거나 다른 식품 또는 식품성분과 함께 사용될 수 있고, 통상적인 방법에 따라 적절하게 사용될 수 있다. 유효성분은 그의 사용 목적(예방 또는 개선)에 따라 적절하게 사용될 수 있다. 일반적으로, 식품 또는 음료의 제조시에 본 발명의 비트 비발효 추출물은 원료에 대하여 15 중량부 이하, 바람직하게는 10 중량부 이하의 양의로 첨가된다. 그러나 건강 조절을 목적으로 하는 장기간의 섭취의 경우에는 안전성 면에서 아무런 문제가 없는 범위의 양으로 사용될 수 있다.When the fermented beet extract of the present invention is used as a food additive, the fermented beet extract may be added as it is or used with other foods or food ingredients, and may be appropriately used according to a conventional method. The active ingredient may be used appropriately depending on the purpose of its use (prevention or improvement). In general, in the production of food or beverage, the non-fermented beet extract of the present invention is added in an amount of 15 parts by weight or less, preferably 10 parts by weight or less, based on the raw material. However, in the case of long-term intake for the purpose of health control, it can be used in an amount within a range that does not cause any problems in terms of safety.
상기 식품의 종류에는 특별한 제한은 없다. 상기 건강기능식품 조성물을 첨가할 수 있는 식품의 예로는 육류, 소시지, 빵, 초콜릿, 캔디류, 스낵류, 과자류, 피자, 라면, 기타 면류, 껌류, 아이스크림류를 포함한 낙농제품, 각종 스프, 음료수, 차 드링크제, 알콜 음료 및 비타민 복합제 등이 있으며, 통상적인 의미에서의 건강식품을 모두 포함한다. 상기 음료는 탄산음료, 기능성이온음료, 쥬스(예를 들어, 사과, 배,포도, 알로에, 감귤, 복숭아, 당근, 토마토쥬스 등), 식혜 등을 포함한다. There is no particular limitation on the type of the food. Examples of foods to which the health functional food composition can be added include meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gum, dairy products including ice cream, various soups, beverages, tea There are drinks, alcoholic beverages, vitamin complexes, and the like, and includes all health foods in the ordinary sense. The beverage includes carbonated beverages, functional ionic beverages, juices (eg, apple, pear, grape, aloe, tangerine, peach, carrot, tomato juice, etc.), sikhye, and the like.
본 발명의 기능성 식품은 식품 제조 시에 통상적으로 첨가되는 성분을 포함하며, 예를 들어, 단백질, 탄수화물, 지방, 영양소 및 조미제를 포함한다. 예컨대, 드링크제로 제조되는 경우에는 유효성분 이외에 천연 탄수화물 또는 향미제를 추가 성분으로서 포함시킬 수 있다. 상기 천연 탄수화물은 모노사카라이드(예컨대, 글루코오스, 프럭토오스 등), 디사카라이드(예컨대, 말토스, 수크로오스 등), 올리고당, 폴리사카라이드(예컨대, 덱스트린, 시클로덱스트린 등) 또는 당알코올(예컨대, 자일리톨, 소르비톨, 에리쓰리톨 등)인 것이 바람직하다. 상기 향미제는 천연 향미제(예컨대, 타우마틴, 스테비아 추출물 등)와 합성 향미제(예컨대, 사카린, 아스파르탐 등)를 이용할 수 있다. 상기 건강기능식품 조성물 외에 여러 가지 영양제, 비타민, 전해질, 풍미제, 착색제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알콜, 탄산음료에 사용되는 탄산화제 등을 더 함유할 수 있다. The functional food of the present invention includes ingredients commonly added during food production, for example, proteins, carbohydrates, fats, nutrients and seasonings. For example, when manufactured as a drink, natural carbohydrates or flavoring agents may be included as additional ingredients in addition to the active ingredient. The natural carbohydrates include monosaccharides (eg, glucose, fructose, etc.), disaccharides (eg, maltose, sucrose, etc.), oligosaccharides, polysaccharides (eg, dextrin, cyclodextrin, etc.) or sugar alcohols (eg, , xylitol, sorbitol, erythritol, etc.). As the flavoring agent, natural flavoring agents (eg, taumatine, stevia extract, etc.) and synthetic flavoring agents (eg, saccharin, aspartame, etc.) may be used. In addition to the health functional food composition, various nutrients, vitamins, electrolytes, flavoring agents, coloring agents, pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohol, carbonic acid It may further contain a carbonation agent and the like used in beverages.
상기 건강기능식품 조성물 이외에 여러 가지 영양제, 비타민, 저해질, 풍미제, 착색제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알콜, 탄산음료에 사용되는 탄산화제 등을 더 함유할 수 있다. 이러한 상기 첨가되는 성분의 비율은 크게 중요하진 않지만 본 발명의 건강기능식품 조성물 100 중량부에 대하여, 0.01 내지 0.1 중량부의 범위에서 선택되는 것이 일반적이다.In addition to the above health functional food composition, various nutrients, vitamins, inhibitors, flavoring agents, coloring agents, pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohols, It may further contain a carbonation agent, etc. used in carbonated beverages. The ratio of these added ingredients is not very important, but is generally selected in the range of 0.01 to 0.1 parts by weight based on 100 parts by weight of the health functional food composition of the present invention.
본 발명은 또한, 상기 5-히드록시말톨(hydroxymaltol)을 함유하는 항산화 활성이 증진된 비트 발효 추출물을 유효성분으로 함유하는 항산화용 화장료 조성물을 제공한다.The present invention also provides an antioxidant cosmetic composition comprising, as an active ingredient, a fermented beetroot extract with enhanced antioxidant activity containing the 5-hydroxymaltol.
본 발명의 화장료 조성물에서, 상기 비트 발효 추출물은 전술한 것과 같다. In the cosmetic composition of the present invention, the fermented beet extract is the same as described above.
본 발명의 화장료 조성물에서, 상기 비트 발효 추출물은 비트 비발효 추출물에 비해 라디칼 소거능이 증가하고, 5-히드록시말톨(hydroxymaltol) 성분이 새롭게 생성되어 항산화 활성이 우수하므로 피부노화 방지, 미백, 주름 개선 등을 위한 기능성 소재로 사용될 수 있다.In the cosmetic composition of the present invention, the fermented beet extract has an increased radical scavenging ability compared to the non-fermented beet extract, and 5-hydroxymaltol component is newly generated and has excellent antioxidant activity, so skin aging prevention, whitening, and wrinkle improvement It can be used as a functional material for etc.
본 발명의 화장료 조성물은 당업계에서 통상적으로 제조되는 어떠한 제형으로도 제조될 수 있으며, 예를 들어, 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션 및 스프레이 등으로 제형화될 수 있고, 보다 상세하게는, 스킨, 스킨 소프트너, 스킨토너, 아스트린젠트, 로션, 밀크로션, 모이스쳐로션, 영양로션, 마사지크림, 영양크림, 아이 크림, 모이스쳐 크림, 핸드크림, 에센스, 영양에센스, 팩, 클렌징폼, 클렌징 워터, 클렌징 로션, 클렌징 크림, 바디로션, 바디클렌져, 비누 또는 파우더의 화장품 제형으로 제조될 수 있으나, 이에 한정하는 것은 아니다. The cosmetic composition of the present invention may be prepared in any formulation conventionally prepared in the art, for example, a solution, suspension, emulsion, paste, gel, cream, lotion, powder, oil, powder foundation, emulsion It may be formulated as foundation, wax foundation and spray, and more specifically, skin, skin softener, skin toner, astringent, lotion, milk lotion, moisture lotion, nourishing lotion, massage cream, nourishing cream, eye cream, Moisture cream, hand cream, essence, nourishing essence, pack, cleansing foam, cleansing water, cleansing lotion, cleansing cream, body lotion, body cleanser, soap or powder may be prepared as cosmetic formulations, but is not limited thereto.
본 발명의 화장료 조성물의 제형이 페이스트, 크림 또는 겔인 경우에는 담체 성분으로서 동물성유, 식물성유, 왁스, 파라핀, 전분, 트라칸트, 셀룰로오스 유도체, 폴리에틸렌 글리콜, 실리콘, 벤토나이트, 실리카, 탈크 또는 산화아연 등이 이용될 수 있다.When the formulation of the cosmetic composition of the present invention is a paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, tracanth, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide, etc. This can be used.
본 발명의 화장료 조성물의 제형이 파우더 또는 스프레이인 경우에는 담체 성분으로서 락토스, 탈크, 실리카, 알루미늄 히드록시드, 칼슘 실리케이트 또는 폴리아미드 파우더가 이용될 수 있고, 특히 스프레이인 경우에는 추가적으로 클로로플루오로 히드로카본, 프로판/부탄 또는 디메틸 에테르와 같은 추진체를 포함할 수 있다.When the formulation of the cosmetic composition of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component, and in particular, in the case of a spray, additional chlorofluorohydro It may contain a propellant such as carbon, propane/butane or dimethyl ether.
본 발명의 화장료 조성물의 제형이 용액 또는 유탁액인 경우에는 담체 성분으로서 용매, 용해화제 또는 유탁화제가 이용되고, 예컨대 물, 에탄올, 이소프로판올, 에틸 카보네이트, 에틸 아세테이트, 벤질 알코올, 벤질 벤조에이트, 프로필렌글리콜, 1,3-부틸글리콜 오일, 글리세롤 지방족 에스테르, 폴리에틸렌 글리콜 또는 소르비탄의 지방산 에스테르가 있다.When the formulation of the cosmetic composition of the present invention is a solution or emulsion, a solvent, solubilizer or emulsifier is used as a carrier component, for example, water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene fatty acid esters of glycol, 1,3-butylglycol oil, glycerol fatty esters, polyethylene glycol or sorbitan.
본 발명의 화장료 조성물의 제형이 현탁액인 경우에는 담체 성분으로서 물, 에탄올 또는 프로필렌글리콜과 같은 액상의 희석제, 에톡실화 이소스테아릴 알코올, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미소결정성 셀룰로오스, 알루미늄 메타히드록시드, 벤토나이트, 아가 또는 트라칸트 등이 이용될 수 있다.When the formulation of the cosmetic composition of the present invention is a suspension, as a carrier component, a liquid diluent such as water, ethanol or propylene glycol, ethoxylated isostearyl alcohol, a suspending agent such as polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester , microcrystalline cellulose, aluminum metahydroxide, bentonite, agar, or tracanth may be used.
본 발명의 화장료 조성물은 상기 유효성분 이외에 화장품 조성물에 통상적으로 이용되는 성분들을 포함하며, 예컨대 지방 물질, 유기 용매, 용해제, 농축제 및 겔화제, 연화제, 항산화제, 현탁화제, 안정화제, 발포제(foaming agent), 방향제, 계면활성제, 물, 이온형 또는 비이온형 유화제, 충전제, 금속이온 봉쇄제 및 킬레이트화제, 보존제, 비타민, 차단제, 습윤화제, 필수 오일, 염료, 안료, 친수성 또는 친유성 활성제, 지질 소낭과 같은 통상적인 보조제, 그리고 담체를 포함한다.The cosmetic composition of the present invention includes components commonly used in cosmetic compositions in addition to the above active ingredients, for example, fatty substances, organic solvents, solubilizers, thickeners and gelling agents, emollients, antioxidants, suspending agents, stabilizers, foaming agents ( foaming agents), fragrances, surfactants, water, ionic or nonionic emulsifiers, fillers, sequestering and chelating agents, preservatives, vitamins, blocking agents, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents , conventional adjuvants such as lipid vesicles, and carriers.
이하, 본 발명을 실시예에 의해 상세히 설명한다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명의 내용이 하기 실시예에 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail by way of Examples. However, the following examples are merely illustrative of the present invention, and the content of the present invention is not limited to the following examples.
제조예 1. 비트 발효 추출물의 제조Preparation Example 1. Preparation of beet fermented extract
제주산 비트를 분쇄하고 동결건조하여 얻어진 비트 분말 10g(제주 테크노파크에서 제공)을 MRS(De Man, Rogosa and Sharpe) 액체배지 1L에 pH 6.5로 적정한 후 고압증기멸균기(autoclave)를 이용하여 멸균하여 비트 발효용 배지를 준비하였다. 그리고 비트 발효에 사용된 락토바실러스 람노서스 GG 배양액은 MRS 액체배지에 접종하고 30℃, 150rpm 조건에서 2일간 배양하여 수득하였다. 상기 준비된 비트 발효용 배지 1L에 7×105 CFU/㎖ 농도의 락토바실러스 람노서스 GG 배양액 10㎖을 첨가하고 30℃, 150rpm 조건에서 5일간 진탕배양하여 발효시켰다. 발효가 끝나고 4,000rpm에서 10분 동안 원심분리하여 상등액을 수득한 후 상기 상등액 1L와 에틸 아세테이트 1L를 혼합하였으며, 분획 깔대기에 상기 혼합액을 넣어 10분간 방치한 다음 최상단의 유기 용매층을 회수함으로써 비트 발효 추출물을 제조하였다. 상기 제조된 비트 발효물을 감압·농축하고 건조시켜 5g을 수득한 후 메탄올 10㎖로 녹여서 실험에 사용하였다. 대조군으로 사용된 비트 비발효 추출물은 상기 비트 발효 추출물의 제조방법에서, 락토바실러스 람노서스 배양액을 접종하고 진탕배양하여 발효시키는 단계를 제외한 나머지 방법을 통해 제조되었다.10 g of beet powder (provided by Jeju Technopark) obtained by crushing Jeju beetroot and lyophilizing it was titrated to pH 6.5 in 1 L of MRS (De Man, Rogosa and Sharpe) liquid medium and sterilized using an autoclave. A medium for beet fermentation was prepared. And the Lactobacillus rhamnosus GG culture medium used for beet fermentation was obtained by inoculating the MRS liquid medium and culturing for 2 days at 30°C and 150rpm conditions. 10 ml of a Lactobacillus rhamnosus GG culture solution at a concentration of 7×10 5 CFU/ml was added to 1 L of the prepared medium for fermentation of beets, and fermented by shaking culture at 30° C. and 150 rpm for 5 days. After fermentation was finished, centrifugation at 4,000 rpm for 10 minutes to obtain a supernatant, 1 L of the supernatant and 1 L of ethyl acetate were mixed. An extract was prepared. The prepared beet fermented product was dried under reduced pressure and concentrated to obtain 5 g, and then dissolved in 10 ml of methanol and used in the experiment. The non-fermented beet extract used as a control was prepared in the method for preparing the fermented beet extract, except for the step of inoculating a Lactobacillus rhamnosus culture medium and fermenting it by shaking culture.
실시예 1. 비트 발효 추출물의 항산화 활성 분석Example 1. Analysis of Antioxidant Activity of Fermented Beet Extract
본 발명의 비트 발효 추출물을 대상으로 DPPH 라디칼 소거능 및 ABTS 라디칼 소거능을 분석하였다. 우선, DPPH 라디칼 소거능을 측정하기 위해 96웰 플레이트의 각 웰에 비트 발효 추출물(10mg/㎖)을 40㎕씩 분주한 후 DPPH(200mM)을 160㎕씩 처리하고 37℃의 암조건에서 30분간 반응시켰으며, 반응이 끝난 후 분광광도계를 이용하여 517nm 파장에서 흡광도를 측정하였다. 또한, ABTS 라디칼 소거능을 측정하기 위해 2.45mM 과황산칼륨(potassium persulfate)에 7mM ABTS 용액을 첨가하여 ABTS 라디칼 용액을 만든 후 사용 전에 16시간 동안 실온의 암조건에서 방치하고 OD734nm=0.7로 맞추기 위해 물로 희석하였다. 96웰 플레이트의 각 웰에 비트 발효 추출물(10mg/㎖)을 20㎕씩 분주한 후 ABTS 용액을 180㎕씩 처리하고 2분간 반응시켰다. 반응이 끝난 후 분광광도계를 이용하여 734nm 파장에서 흡광도를 측정하였다. 대조군으로는 비트 비발효 추출물을 사용하였다.DPPH radical scavenging ability and ABTS radical scavenging ability were analyzed for the beet ferment extract of the present invention. First, in order to measure the DPPH radical scavenging ability, 40 μl of beet ferment extract (10 mg/ml) was dispensed into each well of a 96-well plate, and then 160 μl of DPPH (200 mM) was treated and reacted for 30 minutes in a dark condition at 37°C. After the reaction was completed, the absorbance was measured at a wavelength of 517 nm using a spectrophotometer. In addition, to measure the ABTS radical scavenging activity in 2.45mM potassium persulfate (potassium persulfate) was added to 7mM ABTS solution prior to use, create a radical ABTS solution was left to stand in a dark condition at room temperature for 16 hours, and to fit with OD 734nm = 0.7 diluted with water. After 20 μl of beet ferment extract (10 mg/ml) was dispensed into each well of a 96-well plate, 180 μl of ABTS solution was treated and reacted for 2 minutes. After the reaction was completed, the absorbance was measured at a wavelength of 734 nm using a spectrophotometer. As a control, a non-fermented beet extract was used.
그 결과, ABTS 라디칼 소거능은 비트 비발효 추출물 처리군에서 약 55%, 비트 발효 추출물 처리군에서 약 95%로, 비트 발효 추출물의 항산화 활성이 비트 비발효 추출물에 비해 약 1.7배 증가한 것을 확인하였다(도 1A). 또한, DPPH 라디칼 소거능은 비트 비발효 추출물 처리군에서 약 9%, 비트 발효 추출물 처리군에서 29%로, 비트 발효 추출물의 항산화 활성이 비트 비발효 추출물에 비해 약 3.2배 증가한 것을 확인하였다(도 1B). As a result, the ABTS radical scavenging ability was about 55% in the non-fermented beet extract treatment group and about 95% in the beet ferment extract treatment group, and it was confirmed that the antioxidant activity of the beetroot fermented extract increased about 1.7 times compared to the non-fermented beet extract ( 1A). In addition, the DPPH radical scavenging ability was about 9% in the non-fermented beet extract treatment group and 29% in the beet ferment extract treatment group. ).
실시예 2. 비트 발효 추출물에서 분리·정제된 5-히드록시말톨(hydroxymaltol)의 항산화 활성 분석Example 2. Analysis of antioxidant activity of 5-hydroxymaltol isolated and purified from fermented beet extract
2-1. 비트 발효 추출물에서 항산화 물질(5-hydroxymaltol)의 분리·정제 2-1. Separation and purification of antioxidants (5-hydroxymaltol) from beet fermented extracts
2-1-1. HPLC(high pressure liquid chromatography) 분석2-1-1. High pressure liquid chromatography (HPLC) analysis
비트 발효 추출물 및 비트 비발효 추출물에서 에틸 아세테이트층을 분리 및 농축하고 건조시킨 후 메탄올로 용해시켜 샘플을 준비한 다음 HPLC를 수행하였다. 그 결과, 보유시간 7분에서 비트 발효 추출물로부터 새롭게 생성된 물질에 해당하는 피크를 확인하였다(도 2). 피크 부분에서 분리된 물질은 극성이 매우 강하기 때문에 HPLC 수행 초기에 분리되었다.The ethyl acetate layer was separated from the fermented beet extract and the non-fermented beet extract, concentrated, dried, and dissolved in methanol to prepare a sample, followed by HPLC. As a result, a peak corresponding to a material newly generated from the beet ferment extract was confirmed at a retention time of 7 minutes (FIG. 2). The material separated in the peak portion was separated at the beginning of HPLC performance because of very strong polarity.
2-1-2. ODS(C-18) 오픈컬럼을 이용한 크로마토그래피 분석2-1-2. Chromatographic analysis using ODS (C-18) open column
상기 HPLC를 통해 비트 발효 추출물의 성질을 파악하여 에틸 아세테이트층에서 분리된 물질에 메탄올과 물을 첨가한 후 감압 농축하여 메탄올을 제거하고 물에 현탁된 샘플을 회수하였다. 그 다음, 상기 샘플을 ODS(octadecyl silica) 컬럼(10×10cm)에 넣고 물(0% 메탄올), 10% 메탄올 또는 20% 메탄올로 용출한 후 실리카 플레이트(4×10cm)에 점적하고 클로로포름:메탄올(10:1) 용매를 이용하여 분리한 결과, 물을 사용했을 원하는 물질이 용출되었다(도 3A). 물로 용출된 샘플에서 항산화 활성이 있음을 확인하고 계속적으로 정제를 수행하였다.The properties of the beet ferment extract were identified through the HPLC, methanol and water were added to the material separated from the ethyl acetate layer, and then concentrated under reduced pressure to remove methanol, and a sample suspended in water was recovered. Then, the sample was placed in an ODS (octadecyl silica) column (10×10 cm), eluted with water (0% methanol), 10% methanol, or 20% methanol, and then dropped onto a silica plate (4×10 cm), and chloroform: methanol (10:1) As a result of separation using a solvent, a desired substance that would have used water was eluted (FIG. 3A). It was confirmed that the sample eluted with water had antioxidant activity, and purification was continued.
2-1-3. 실리카겔 크로마토그래피(silica gel chromatography)2-1-3. Silica gel chromatography
상기 물로 용출된 샘플을 농축 건조하여 클로로포름:메탄올(10:1) 용매로 용해한 후 실리카겔 오픈컬럼(50×4cm)을 이용하여 분획하였으며, 분획은 각각 1, 2, 3, 4번 분획으로 나누어 받았다(도 3B-a). 각 분획물을 실리카겔 플레이트(4×10cm)에 점적하고 클로로포름:메탄올(10:1) 용매를 이용하여 분리한 결과, 원하는 황산화 활성이 2번 분획물에서 확인되었으며(도 3B-b), 이후 정제 단계에서 2번 분획물을 샘플로 사용하였다. The sample eluted with water was concentrated to dryness, dissolved in chloroform: methanol (10: 1) solvent, and fractionated using an open silica gel column (50 × 4 cm), and the fractions were divided into 1, 2, 3, and 4 fractions, respectively. (Fig. 3B-a). Each fraction was dropped onto a silica gel plate (4×10 cm) and separated using a chloroform:methanol (10:1) solvent. As a result, the desired sulfation activity was confirmed in the second fraction (FIG. 3B-b), and subsequent
2-1-4. Sephadex G-10가 충진된 컬럼을 이용한 크로마토그래피2-1-4. Chromatography using a column packed with Sephadex G-10
상기 2번 분획물 샘플을 농축하고 물로 용해시킨 후, Sephadex G-10 수지가 충진된 컬럼(50×4cm)에 넣어 다시 분획하였으며, 분획은 각각 1, 2번 분획으로 나누어 받았다(도 4A-a). 각 분회물을 대상으로 실리카 플레이트 및 ODS C18 플레이트를 사용하여 정제도를 확인한 결과, 2-2번 분획물의 정제도가 가장 우수함을 확인하였다(도 4A-b). 또한, 2-1 및 2-2 분획물이 항산화 활성을 측정한 결과 2-2 분획물의 항산화 활성이 2-1 분획물에 비해 우수함을 확인하였고, 실라카 플레이트를 사용하는 것 보다 ODS C18 플레이트를 사용하는 것이 물질의 정제 효과가 더 우수함을 확인함으로써, 이후 정제 단계에서는 2-1 분획물과 분리용 ODS C18 플레이트를 사용하였다. After the
2-1-5. Prep ODS C18 TLC(thin layer chromatyography)2-1-5. Prep ODS C18 thin layer chromatography (TLC)
대용량 물질 분리를 위해 상기 2-1 분획물 0.5㎖을 메탄올로 용해한 후 ODS C18가 코딩된 유리 플레이트(20×20cm)에 점적하고 메탄올:물(1:1) 용매를 이용하여 2시간 동안 TLC 챔버에서 전개시켜 분리하였으며(도 4B-a), 상기와 동일한 방법으로 20장 플레이트를 사용하여 정제하였다. 그 다음으로, 분리된 물질을 농축하고 건조한 후 메탄올로 용해시켜서 ODS C18이 코팅된 플라스틱 플레이트(2×10cm)에 점적하고 메탄올:물(5:1) 용매를 이용하여 1번 및 2번 물질이 정제됨을 확인하였다(도 4B-b). 상기 정제된 1번 및 2번 물질을 대상으로 항산화 활성을 측정한 결과 1번 물질의 항산화 활성이 우수함을 확인하였다.After dissolving 0.5 ml of the fraction 2-1 with methanol for large-capacity material separation, dropwise on a glass plate (20×20 cm) coded with ODS C18, and in a TLC chamber for 2 hours using a methanol:water (1:1) solvent. It was separated by development (FIG. 4B-a), and purified using a 20-sheet plate in the same manner as above. Next, the separated material was concentrated and dried, dissolved with methanol, and dropped onto a plastic plate (2×10 cm) coated with ODS C18, and
2-1-6. Prep HPLC2-1-6. Prep HPLC
상기 Prep TLC를 통해 얻어진 2번 물질 500㎕를 HPLC 기기에 주입한 후 메탄올:RF=0.45 용매 조건에 따라 HPLC를 수행하여 보유시간 36분에서 나타난 메인 피크에 해당하는 물질을 분리하였다(도 5A). 또한 상기 분리된 물질을 확인하기 위해 C18 플레이트를 이용하여 물질의 다시 분리 및 정제하였다(도 5B).After 500 μl of
2-2. 비트 발효 추출물에서 정제된 물질의 구조분석2-2. Structural analysis of purified substances from beet ferment extract
상기 비트 발효 추출물에서 분리·정제된 물질의 구조를 분석하기 위해 1차원 NMR(nuclear magnetic resonance) 방법인 H-NMR 및 C-NMR과(도 6), 2차원 NMR 방법인 HMBC-NMR 및 HMQC-NMR(도 7)을 수행하였다. 도 6A의 H-NMR 결과에서 7.84ppm singlet proton은 아로마틱링(aromatic ring) C-6에 결합된 수소를, 2.30ppm singlet proton은 아로마틱링 C-2에 결합된 메틸수소를 의미하며, 도 6B의 C-NMR 결과에서 142.90ppm은 아로마틱링 C-2에 결합된 탄소를, 140.38ppm은 아로마틱링 C-3에 결합된 탄소를, 170.25ppm은 아로마틱링 C-4에 결합된 탄소를, 145.80ppm은 아로마틱링 C-5에 결합된 탄소를, 151.83ppm은 아로마틱링 C-6에 결합된 탄소를, 14.51ppm은 아로마틱링 C-2에 결합된 메틸탄소를 의미한다(CH3 1개, CH 1개, C 4개). 또한, 도 7A의 HMBC 결과에서 7.84ppm singlet proton은 아로마틱링 C-6에 결합된 수소를 의미하고 170.25ppm, 145.80ppm 및 151.83ppm은 탄소 결합을 의미하며, 도 7B의 HMQC 결과에서 2.20ppm은 메틸프로톤을 의미한다.In order to analyze the structure of the material separated and purified from the beet ferment extract, one-dimensional NMR (nuclear magnetic resonance) methods H-NMR and C-NMR (FIG. 6), and two-dimensional NMR methods HMBC-NMR and HMQC- NMR (Fig. 7) was performed. In the H-NMR result of FIG. 6A, 7.84 ppm singlet proton means hydrogen bound to aromatic ring C-6, and 2.30 ppm singlet proton means methyl hydrogen bound to aromatic ring C-2. In the C-NMR result, 142.90 ppm is the carbon bonded to the aromatic ring C-2, 140.38 ppm is the carbon bonded to the aromatic ring C-3, 170.25 ppm is the carbon bonded to the aromatic ring C-4, and 145.80 ppm is the carbon bonded to the aromatic ring C-4. Carbon bonded to aromatic ring C-5, 151.83 ppm refers to carbon bonded to aromatic ring C-6, and 14.51 ppm refers to methyl carbon bonded to aromatic ring C-2 (
또한, ESI-Mass spectrometer로 분자량을 측정하여 분자량이 143g/mol임을 확인하였다(도 8). 이를 통해, 본 발명의 비트 발효 추출물에서 정제된 물질이 5-히드록시말톨(hydroxymaltol)인 것으로 확인되었다. In addition, by measuring the molecular weight with an ESI-Mass spectrometer, it was confirmed that the molecular weight was 143 g/mol (FIG. 8). Through this, it was confirmed that the substance purified from the beet ferment extract of the present invention was 5-hydroxymaltol.
2-3. 비트 발효 추출물 유래 5-히드록시말톨의 DPPH 라디칼 소거능 측정2-3. Measurement of DPPH radical scavenging activity of 5-hydroxymaltol derived from beet ferment extract
비트 발효 추출물로부터 분리·정제된 항산화 물질인 5-히드록시말톨을 대상으로 DPPH assay를 수행한 결과, 5-히드록시말톨의 농도 의존적으로 DPPH 라디칼 소거능이 증가하는 것을 확인하였다(도 9). 상기 결과를 종합하면, 본 발명의 비트 발효 추출물은 비트를 발효시킴으로써 새롭게 생산된 5-히드록시말톨 성분에 의해 항산화 활성이 증진된 것임을 알 수 있었다.As a result of performing the DPPH assay on 5-hydroxymaltol, an antioxidant isolated and purified from the beet ferment extract, it was confirmed that the DPPH radical scavenging ability was increased in a concentration-dependent manner of 5-hydroxymaltol (FIG. 9). Summarizing the above results, it was found that the antioxidant activity of the fermented beet extract of the present invention was enhanced by the 5-hydroxymaltol component newly produced by fermenting beets.
Claims (8)
(2) 상기 (1) 단계의 비트 발효용 배지에 락토바실러스 람노서스 균주 배양액을 접종하고 28~32℃에서 4~6일 동안 진탕배양하여 발효시킨 후 원심분리하여 상등액을 수득하는 단계; 및
(3) 상기 (2) 단계의 상등액과 에틸 아세테이트 용매를 혼합하여 추출하는 단계;를 포함하여 제조하는 것을 특징으로 하는 5-히드록시말톨(hydroxymaltol)을 함유하는 항산화 활성이 증진된 비트 발효 추출물의 제조방법.(1) adding 0.5 to 1.5% (w/v) of beet powder to a liquid medium and sterilizing to prepare a medium for fermentation of beets;
(2) inoculating the culture solution of the Lactobacillus rhamnosus strain into the medium for fermentation of beets of step (1), fermenting by shaking culture at 28-32° C. for 4-6 days, and then centrifuging to obtain a supernatant; and
(3) extracting by mixing the supernatant of step (2) with an ethyl acetate solvent; manufacturing method.
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