KR20100043882A - Extract of mulberry leaves having inhibition activity for helicobacter pylori, method for preparing the same and the healthfunctional food using thereof - Google Patents
Extract of mulberry leaves having inhibition activity for helicobacter pylori, method for preparing the same and the healthfunctional food using thereof Download PDFInfo
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- KR20100043882A KR20100043882A KR1020080103127A KR20080103127A KR20100043882A KR 20100043882 A KR20100043882 A KR 20100043882A KR 1020080103127 A KR1020080103127 A KR 1020080103127A KR 20080103127 A KR20080103127 A KR 20080103127A KR 20100043882 A KR20100043882 A KR 20100043882A
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- South Korea
- Prior art keywords
- helicobacter pylori
- acid
- leaf extract
- mulberry leaf
- extract
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
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- A61K36/605—Morus (mulberry)
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/02—Bacterial antigens
- A61K39/105—Delta proteobacteriales, e.g. Lawsonia; Epsilon proteobacteriales, e.g. campylobacter, helicobacter
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/308—Foods, ingredients or supplements having a functional effect on health having an effect on cancer prevention
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/32—Foods, ingredients or supplements having a functional effect on health having an effect on the health of the digestive tract
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
Abstract
Description
본 발명은 페놀성 물질을 함유한 헬리코박터 파이로리(Helicobacter pylori) 균에 대해 항균능을 갖는 뽕잎 추출물, 이의 제조방법 및 이를 이용한 건강기능식품에 관한 것으로, 좀 더 구체적으로는 뽕잎 추출물의 페놀성 물질 중에서 헬리코박터 파이로리 균에 대하여 항균 효과를 갖는 적어도 2종의 페놀성 물질들을 함유하는 뽕잎 추출물, 이의 제조방법 및 이를 이용한 건강기능식품에 관한 것이다.The present invention relates to a mulberry leaf extract having an antimicrobial activity against Helicobacter pylori bacteria containing a phenolic substance, a preparation method thereof, and a health functional food using the same, and more specifically, among the phenolic substances of the mulberry leaf extract. It relates to a mulberry leaf extract containing at least two phenolic substances having an antimicrobial effect against Helicobacter pylori bacteria, a preparation method thereof and a health functional food using the same.
헬리코박터 파이로리균은 1983년에 호주의 마샬(Marshall)과 워렌(Warren)에 의해 발견되었으며, 위염 및 위궤양 환자의 위점막 생검조식으로부터 그람음성의 만곡형 간균으로 관찰되어, B형 만성위염과 위십이지장 궤양을 유발시키며 위암 발생의 일차적 결정요인으로 알려져 있다.Helicobacter pylori was discovered in 1983 by Marshall and Warren of Australia and was observed as a Gram-negative curved bacilli from gastric mucosal biopsy of gastritis and gastric ulcer patients. It causes ulcers and is known as the primary determinant of gastric cancer.
헬리코박터 파이로리균은 요소 분해효소인 우레아제(urease)를 분비하여 위액내의 요소(H2NCONH2, urea) 1 분자를 가수분해하여 2분자의 암모니아(NH3)를 형성한다. 우레아제가 인체 위장관 표피 세포에 헬리코박터 파이로리 균을 감염시키고, 콜로니화(colonization)를 돕는 것에 대한 밀접한 관련성이 보고되어 있다. 구체적으로, 우레아제를 불활성시킨 헬리코박터 파이로리 균주는 위점막세포에서 콜로니화하지 못하며, 우레아제 활성이 헬리코박터 파이로리의 콜로니화에 필수적이라는 보고가 있으며(Eaton K.A., et al., Infect Immun., 59, pp2470-2475, 1991), 헬리코박터 파이로리 우레아제에 의해 생성된 암모니아는 위액내 pH를 증가시키고, 위 점액층을 손상시키며(Sidebotham R.L., et al., J. Clin. Pathol., 44, pp52-57, 1991), 암모니아 자체가 위점액층 세포의 산소 소비와 미토콘드리아의 ATP 생성을 저해하고(Tsujii M., et al., Gastroenterology, 102, pp1881-1888, 1992), 궁극적으로 암모니아는 모노클로로아민(monochloroamine)을 형성하여 반응성 산소종(reactive oxygen species)을 생성하기 때문에 세포 손상을 유발하여 만성염증을 일으키고, 나아가 DNA 손상을 일으켜 암발생 과정을 촉진시킨다는 보고가 있다(Hahm K.B., et al., Am. J. Gastroenterol., 92, pp1853-1857, 1997).Helicobacter pylori bacteria secrete urease, a urease, to hydrolyze one molecule of urea (H 2 NCONH 2 , urea) in gastric juice to form two molecules of ammonia (NH 3 ). There is a close association between urease infecting human gastrointestinal epidermal cells and helping to colonize the bacterium Helicobacter pylori. Specifically, the Helicobacter pylori strain inactivated urease does not colonize gastric mucosa cells, and it has been reported that urease activity is essential for colonization of Helicobacter pylori (Eaton KA, et al., Infect Immun., 59, pp2470-). 2475, 1991), ammonia produced by Helicobacter pylori urease increases the pH in gastric juice and damages the gastric mucus layer (Sidebotham RL, et al., J. Clin. Pathol., 44, pp52-57, 1991), Ammonia itself inhibits oxygen consumption of gastric mucosa cells and ATP production in mitochondria (Tsujii M., et al., Gastroenterology, 102, pp1881-1888, 1992), and ultimately ammonia forms monochloroamine Because of the production of reactive oxygen species, it has been reported to induce cell damage, lead to chronic inflammation, and further to DNA damage, thereby promoting the cancer development process (Hahm K). B, et al., Am. J. Gastroenterol., 92, pp 1853-1857, 1997).
상기와 같은 헬리코박터 파이로리의 활성을 저해하기 위해 항생제 요법이 사용될 수 있으나, 항생제 내성 균주의 출현으로 인해 효율성이 떨어지는 문제가 있다. 따라서, 최근에는 헬리코박터 파이로리를 제균할 수 있는 효과적인 방법으로 다양한 백신이 개발되고 있으며, 이들 중 대부분은 헬리코박터 파이로리의 병원성 에 특이적인 표적인자(antigen)로 알려진 우레아제, VacA, CagA 및 뉴트로필-활성 단백질(neutrophil-activating protein; NAP)과 같은 단백질을 표적으로 한 억제자의 탐색에 대한 연구들이 진행되고 있다.Antibiotic therapy may be used to inhibit the activity of the Helicobacter pylori as described above, but there is a problem of low efficiency due to the emergence of antibiotic resistant strains. Therefore, a variety of vaccines have recently been developed as an effective way to kill Helicobacter pylori, most of which are urease, VacA, CagA and Neutrofil-active proteins known as antigens specific for the pathogenicity of Helicobacter pylori. Research into the search for inhibitors targeting proteins such as (neutrophil-activating protein (NAP)) is ongoing.
이와 관련된 선행기술의 예로는 특허문헌 1이 있다. 특허문헌 1은 헬리코박터 파이로리의 우레아제 활성 저해능을 지닌 (-)-에피카테킨((-)-epicatechin; EC), (-)-에피갈로카테킨((-)-epigallocatechin; EGC), (-)-에피카테킨 3-갈레이트((-)-epicatechin 3-galate; ECG) 및 (-)-에피갈로카테킨 3-O-갈레이트((-)-epigallocatechin 3-O-gallate; EGCG)을 포함하여 구성된 페놀성 물질을 함유하는 녹차 추출물을 개시하고 있다.An example of the related art is
그러나, 본 발명의 주요 성분인 뽕잎 추출물이 위장에 상재하는 헬리코박터 파이로리 균에 대한 항균효과를 지닌다는 구체적인 보고는 아직 없는 실정이다.However, there is no specific report that the mulberry leaf extract, the main component of the present invention, has an antimicrobial effect against Helicobacter pylori bacteria present in the stomach.
특허문헌 1: 한국 등록특허 제10-0673605호Patent Document 1: Korea Patent Registration No. 10-0673605
이에 본 발명에서는 뽕잎 추출물 중에서 클로로겐산(Chlorogenic acid), 카페인산(Caffeic acid) 및 로즈마릭산(rosemarinic acid) 등의 페놀성 물질이 헬리코박터 파이로리 균에 대해 항균능을 갖는 것을 발견하였고, 본 발명은 이에 기초하여 완성되었다.Therefore, in the present invention, it was found that phenolic substances such as chlorogenic acid, caffeic acid and rosemarinic acid have antibacterial activity against Helicobacter pylori in the mulberry leaf extract. Completed on the basis of
따라서, 본 발명의 목적은 헬리코박터 파이로리 균에 대한 항균활성 억제효과를 갖는 페놀성 물질을 함유하는 뽕잎 추출물을 제공하는 데 있다.Accordingly, an object of the present invention is to provide a mulberry leaf extract containing a phenolic substance having an antimicrobial activity inhibitory effect against Helicobacter pylori bacteria.
본 발명의 다른 목적은 상기 뽕잎 추출물의 제조방법을 제공하는 데 있다.Another object of the present invention to provide a method for producing the mulberry leaf extract.
본 발명의 또 다른 목적은 상기 페놀성 물질을 함유하는 뽕잎 추출물을 이용한 건강기능식품을 제공하는 데 있다.Still another object of the present invention is to provide a health functional food using the mulberry leaf extract containing the phenolic substance.
상기 목적을 달성하기 위한 본 발명의 헬리코박터 파이로리 균에 대해 항균능을 갖는 뽕잎추출물은 뽕잎으로부터 추출되며, 헬리코박터 파이로리 균에 대해 항균능을 갖는 클로로겐산, 카페인산 및 로즈마릭산으로 이루어진 군으로부터 선택된 2종의 페놀성 물질을 함유한다.Mulberry leaf extract having an antimicrobial activity against the Helicobacter pylori bacteria of the present invention for achieving the above object is extracted from the mulberry leaves, two species selected from the group consisting of chlorogenic acid, caffeic acid and rosemary acid having an antimicrobial activity against Helicobacter pylori bacteria Contains phenolic substances.
본 발명의 다른 목적을 달성하기 위한 헬리코박터 파이로리 균에 대해 항균능을 갖는 뽕잎추출물의 제조방법은 건조 뽕잎을 에탄올을 가하여 페놀성 물질을 추출한 후, 다공성 수지 칼럼을 이용하여 전개시킨 에탄올 전개액에서 헬리코박터 파이로리 균에 대해 항균능을 갖는 전개액을 회수하여 감압 농축하여 추출한 다음, 고성능 액체 크로마토그래피에 의해 분리시켜 클로로겐산, 카페인산 및 로즈마릭산으로 이루어진 군으로부터 선택된 2종의 페놀성 물질을 얻는 것을 특징으로 한다.Method for producing a mulberry leaf extract having an antimicrobial activity against Helicobacter pylori bacteria for achieving another object of the present invention, after extracting the phenolic material by adding ethanol to the dried mulberry leaves, Helicobacter in an ethanol developing solution developed using a porous resin column The developer having antibacterial activity against Pylori was recovered, concentrated under reduced pressure, extracted by high performance liquid chromatography, and separated by high performance liquid chromatography to obtain two phenolic substances selected from the group consisting of chlorogenic acid, caffeic acid and rosemary acid. It is done.
본 발명에 따른 제조방법에 있어서, 상기 건조 뽕잎은 40∼90% 에탄올을 가하여 20ㅁ1℃에서 24ㅁ1시간 동안 추출하는 것을 특징으로 한다.In the production method according to the present invention, the dried mulberry leaves are characterized in that 40 to 90% ethanol is added to extract for 20 ㅁ 1 hour at 20 ㅁ 1 ℃.
본 발명의 또 다른 목적을 달성하기 위한 건강 기능식품은 상기 헬리코박터 파이로리 균에 대해 항균능을 갖는 뽕잎추출물을 함유하는 것을 특징으로 한다.Health functional food for achieving another object of the present invention is characterized by containing the mulberry leaf extract having an antimicrobial activity against the Helicobacter pylori bacteria.
이상과 같이, 본 발명에 의해 페놀성 물질을 함유하는 뽕잎 추출물은 헬리코박터 파이로리(Helicobacter pylori)균에 대한 항균 효과를 나타내므로, 헬리코박터 파이로리균에 의해 발생하는 위암, 위궤양, 위염 등 각종 위장관련 질병의 치료 및 예방용으로 활용이 가능하며, 위염과 같은 위장 질환의 개선에 효과적인 기능성 음료, 건강 기능 식품 등의 기능성 식품 분야에 유용하게 이용될 수 있다.As described above, exhibits an antibacterial effect on bacteria mulberry leaf extract of H. pylori (Helicobacter pylori) containing phenolic compounds by the invention, of which caused by the Helicobacter pylori bacteria gastric cancer, gastric ulcer, gastritis and various gastrointestinal-related disease It can be used for the treatment and prevention, and can be usefully used in the field of functional foods, such as functional drinks, health functional foods effective for the improvement of gastrointestinal diseases such as gastritis.
이하, 본 발명을 좀 더 상세히 설명하면 다음과 같다.Hereinafter, the present invention will be described in more detail.
일반적으로 뽕잎은 해열, 진해, 소염제로서 감기, 눈병, 고혈압 등의 치료에 쓰인다. 동의보감과 본초강목에 따르면, 뽕잎은 혈관강화에 좋다고 했다. 뽕잎에는 모세혈관을 튼튼하게 해주는 루틴이라는 것이 메밀보다 18배나 많이 들어 있다. 뽕잎은 또 혈당을 떨어뜨리는 성분이 10종이나 들어있어서 당뇨병을 예방하는 효능이 있다. 뽕잎은 혈관 안에 있는 지방 덩어리인 고지혈증과 혈액의 끈적끈적한 성분인 혈전을 용해시켜 혈압을 안정시키며 동맥경화를 막는 효능도 있는 것으로 알려졌다. 뽕잎은 또 중금속을 제거하는 효능이 탁월하고 대소변이 잘 나오게 하며 노화억제와 암예방에도 효과가 있다. 이밖에 다이어트, 소화촉진, 관절통 예방에 효과가 있고 머리를 맑아지게 하며 흰머리가 검어지게 한다.In general, mulberry leaves are used for the treatment of colds, eye diseases, high blood pressure as antipyretic, antitussive, anti-inflammatory. According to Dongbogam and herbaceous tree, mulberry leaves are good for strengthening blood vessels. Mulberry leaves contain 18 times more routines than buckwheat to make capillaries stronger. Mulberry leaves also contain 10 kinds of ingredients that lower blood sugar, which is effective in preventing diabetes. Mulberry leaves are known to dissolve hyperlipidemia, a mass of fat in blood vessels, and blood clots, a sticky component of blood, to stabilize blood pressure and prevent atherosclerosis. Mulberry leaves are also effective in removing heavy metals, make urine well out, and are effective in preventing aging and preventing cancer. In addition, it is effective in promoting diet, digestion, and preventing joint pain, clearing the head, and darkening the gray hair.
그러나, 본 발명의 주요 성분인 뽕잎 추출물이 위장에 상재하는 헬리코박터 파이로리균에 대한 항균효과를 지닌다는 구체적인 보고는 아직 없는 실정이다. 본 발명에서는 뽕잎 추출물 중에서 클로로겐산, 카페인산 및 로즈마릭산 등의 페놀성 물질이 헬리코박터 파이로리 균에 대해 항균능을 갖는 것을 발견하였다. 특히, 상기 페놀성 물질로부터 선택된 2종의 페놀성 물질이 헬리코박터 파이로리 균에 대해 우수한 항균능을 갖는다.However, there is no specific report that the mulberry leaf extract, which is the main component of the present invention, has an antimicrobial effect against Helicobacter pylori bacteria present in the stomach. In the present invention, it was found that phenolic substances such as chlorogenic acid, caffeic acid and rosemary acid in the mulberry leaf extract have antibacterial activity against Helicobacter pylori. In particular, two phenolic substances selected from the phenolic substances have excellent antimicrobial activity against Helicobacter pylori bacteria.
본 발명에 따르면, 건조 뽕잎에 에탄올을 가하면 프로토카테큐익 산(Protocatecuic acid), 클로로겐산, 카페인산, 큐마릭산(Courmaric acid) 및 로즈마릭산 등의 페놀성 물질이 추출된다. 이때, 상기 건조 뽕잎은 40∼90% 에탄올을 가하여 20ㅁ1℃에서 24ㅁ1시간 동안 추출하는 것이 경제적인 효율면에서 바람직하다.According to the present invention, when ethanol is added to dried mulberry leaves, phenolic substances such as protocatecuic acid, chlorogenic acid, caffeic acid, curmaric acid and rosemary acid are extracted. At this time, the dried mulberry leaves are preferably extracted from 20 ㅁ 1 ℃ for 24 ㅁ 1 hour by adding 40 to 90% ethanol in terms of economical efficiency.
본 발명에 있어서, 상기 추출물은 다공성 수지 칼럼을 이용하여 전개시킨 에탄올 전개액에서 헬리코박터 파이로리 균에 대해 항균능을 갖는 전개액을 회수하여 감압 농축하여 에탄올이 헬리코박터 파이로리 균에 대해 영향을 주지 않도록 하여 항균효과 탐색을 실시한다. 이 분획물 중에서 고성능 액체 크로마토그래피와 박막 크로마토그래피 C18 컬럼과 MCI-gel CHP 20P를 이용하여 단일 페놀성 물질로 정제하여 각 단일물질의 헬리코박터 파이로리 균에 대해 항균능을 시험하였다. 그 결과, 클로로겐산, 카페인산 및 로즈마릭산이 헬리코박터 파이로리 균에 대해 항균능을 나타내었으며, 특히, 상기 페놀성 물질중에서 2종의 페놀성 물질의 혼합 성분 이 헬리코박터 파이로리 균에 대해 더욱 우수한 항균능을 나타내었다.In the present invention, the extract is concentrated under reduced pressure by recovering a developing solution having antimicrobial activity against Helicobacter pylori bacteria in the ethanol developing solution developed using a porous resin column to prevent ethanol from affecting the Helicobacter pylori bacteria Do an effect search. Among these fractions, high-performance liquid chromatography and thin-film chromatography C 18 column and MCI-gel CHP 20P were purified to a single phenolic substance to test the antimicrobial activity against Helicobacter pylori bacteria of each single substance. As a result, chlorogenic acid, caffeic acid and rosemary acid showed antimicrobial activity against Helicobacter pylori bacteria, and especially, the mixed component of two phenolic substances among the phenolic substances showed better antimicrobial activity against Helicobacter pylori bacteria. It was.
이는 본 발명에 의한 추출물이 헬리코박터 파이로리균에 의해 발생하는 위암, 위궤양, 위염 등 각종 위장관련 질병의 치료 및 예방용으로 활용이 가능하다.This extract can be used for the treatment and prevention of various gastrointestinal diseases, such as gastric cancer, gastric ulcers, gastritis caused by Helicobacter pylori bacteria.
또한, 본 발명은 상기 헬리코박터 파이로리의 활성 저해능을 지닌 뽕잎 추출물을 함유하는 건강기능식품을 제공한다.In addition, the present invention provides a health functional food containing the mulberry leaf extract having an activity inhibiting activity of the Helicobacter pylori.
즉, 본 발명의 뽕잎 추출물은 위장 질환 개선을 위한 목적으로 식품 또는 음료에 첨가될 수 있다. 이때, 식품 또는 음료 중에 본 발명의 상기 뽕잎 추출물의 양은 일반적으로 전체 식품 중량의 20 내지 70 중량%로 가할 수 있으며, 위장 질환의 개선을 목적으로 한 기능성 음료, 환제, 정제 또는 상기 성분을 건조 분말화하여 충진한 연질 또는 경질 캡슐제의 형태로 이용할 수 있고, 음료 조성물에는 100 ㎖를 기준으로 0.02 내지 30g, 바람직하게는 0.3 내지 1g의 비율로 본 발명의 추출물을 가할 수 있다.That is, the mulberry leaf extract of the present invention may be added to food or beverage for the purpose of improving gastrointestinal diseases. At this time, the amount of the mulberry leaf extract of the present invention in the food or beverage can be generally added to 20 to 70% by weight of the total food weight, and the functional beverage, pills, tablets or dry powder for the purpose of improving gastrointestinal diseases It can be used in the form of a soft or hard capsule filled with a powder, the beverage composition can be added to the extract of the present invention in a ratio of 0.02 to 30g, preferably 0.3 to 1g based on 100ml.
본 발명의 건강 음료 조성물은 필수 성분으로서 상기 추출물을 함유하는 외에는 액체성분에는 특별한 제한점은 없으며 통상의 음료와 같이 여러 가지 향미제 또는 천연 탄수화물 등을 추가 성분으로서 함유할 수 있다. 상술한 천연 탄수화물의 예는 모노사카라이드, 예를 들어, 포도당, 과당 등의 디사카라이드, 예를 들어 말토스, 슈크로스 등의 폴리사카라이드, 예를 들어 덱스트린, 시클로덱스트린 등과 같은 통상적인 당 및 자일리톨, 솔비톨, 에리트리톨 등의 당알콜이다. 상술한 것 이외의 향미제로서 천연 향미제(타우마틴, 스테비아 추출물(예를 들어, 레바우디오시드 A, 글리시르히진등) 및 합성 향미제(사카린, 아스파르탐 등)를 유리하게 사용 할 수 있다. 상기 천연 탄수화물의 비율은 본 발명의 조성물 100 ㎖당 일반적으로 약 1 내지 20g, 바람직하게는 약 5 내지 12g이다.The health beverage composition of the present invention has no special limitation except for containing the extract as an essential ingredient, and may contain various flavors or natural carbohydrates, etc. as additional ingredients, as in general beverages. Examples of the above-mentioned natural carbohydrates include monosaccharides such as disaccharides such as glucose and fructose, for example polysaccharides such as maltose and sucrose, and conventional sugars such as dextrin and cyclodextrin. And sugar alcohols such as xylitol, sorbitol, and erythritol. As flavoring agents other than those mentioned above, natural flavoring agents (tauumatin, stevia extracts (e.g., rebaudioside A, glycyrrhizin, etc.) and synthetic flavoring agents (saccharin, aspartame, etc.) can be advantageously used. The proportion of natural carbohydrates is generally about 1 to 20 g, preferably about 5 to 12 g per 100 ml of the composition of the present invention.
상기 외에 본 발명의 페놀성 물질을 함유한 뽕잎 추출물은 여러가지 영양제, 비타민, 광물(전해질), 합성 풍미제 및 천연풍미제 등의 풍미제, 착색제 및 중진제(치즈, 초콜릿 등), 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알콜, 탄산 음료에 사용되는 탄산화제 등을 함유할 수 있다. 그밖에 본 발명의 조성물들은 천연 과일 쥬스 및 과일 쥬스 음료 및 야채 음료의 제조를 위한 과육을 함유할 수 있다. 이러한 성분은 독립적으로 또는 조합하여 사용할 수 있다.In addition to the above, the mulberry leaf extract containing the phenolic substance of the present invention is a flavor, such as various nutrients, vitamins, minerals (electrolytes), synthetic flavors and natural flavors, coloring and neutralizing agents (such as cheese, chocolate), pectic acid and Salts thereof, alginic acid and salts thereof, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohols, carbonation agents used in carbonated drinks and the like. The compositions of the present invention may also contain pulp for the production of natural fruit juices and fruit juice beverages and vegetable beverages. These components can be used independently or in combination.
이하, 실시 예를 통하여 본 발명을 좀 더 구체적으로 살펴보지만, 하기 예에 본 발명의 범주가 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited to the following Examples.
실시 예 1Example 1
뽕잎으로부터 페놀(phenol)성 물질의 용출에 미치는 에탄올 농도의 영향Effect of Ethanol Concentration on the Elution of Phenolic Compounds from Mulberry Leaves
건조된 뽕잎에 다양한 농도의 에탄올을 가하여 20ㅁ1℃의 온도를 유지하면서 약 24ㅁ1시간 동안 추출하였다. 그 결과, 도 1과 같이 약 80%의 에탄올에서 농도에서 추출량이 가장 높게 나타났다.Ethanol of various concentrations was added to the dried mulberry leaves and extracted for about 24 ㅁ 1 hour while maintaining the temperature of 20 ㅁ 1 ℃. As a result, as shown in Figure 1 in the ethanol of about 80% the extraction amount was the highest.
실시 예 2Example 2
뽕잎 추출물의 헬리코박터 파이로리 균에 대한 항균효과Antimicrobial Effect of Mulberry Leaf Extract against Helicobacter pylori
상기 실시 예 1의 뽕잎 추출물로 헬리코박터 파이로리 균을 저해하는 물질을 탐색한 결과, 뽕잎의 물 추출물에서는 제해환이 나타나지 않았으며, 에탄올 추출물에서 지름 약 15㎜의 저해환을 나타내었다. 그 결과를 하기 표 1에 나타내었다.As a result of searching for a substance inhibiting the Helicobacter pylori bacteria with the mulberry leaf extract of Example 1, the water extract of the mulberry leaves did not show the deterrent ring, the ethanol extract showed an inhibitory ring of about 15㎜ in diameter. The results are shown in Table 1 below.
실시 예 3 Example 3
시료 추출물의 HPLC 분석HPLC analysis of sample extract
뽕잎 추출물 중에서 페놀성 물질의 존재유무를 알아보기 위해 HPLC 분석을 통해서 페놀(simple phenol)양을 알아보기 위해 표준품으로 프로토카테큐익산, 카페인산, 클로로겐산, 큐마릭산, 로즈마릭산 등 5종을 에탄올에 용해시켜 사용하였고, 시료는 0.2 ㎍ 필터로 2㎖를 여과하고, 그 중 5㎕를 주입하여 분석하였다. 분석 조건 칼럼(column)은 애질런트(Agilent) zorbaxTM(SB-C18, 250ㅧ4.6㎜)를 30℃로 유지하였고, 검출기는 VWD UV 검출기(detector)를 사용하여 306㎚에서 측정하였다. 이동상은 메탄올과 인산(pH 2.5)의 비율을 달리 하여 사용하였고, 이때 흐름 속도는 1㎖/min이었다. In order to determine the presence of phenolic substances in mulberry leaf extract, five kinds of protocatecuic acid, caffeic acid, chlorogenic acid, cumaric acid, and rosemary acid were used as standard products to determine the amount of phenol (simple phenol) through HPLC analysis. The solution was dissolved in ethanol, and the sample was analyzed by filtering 2 ml with a 0.2 µg filter and injecting 5 µl. Analytical conditions The column maintained the Agilent zorbax ™ (SB-C18, 250 × 4.6 mm) at 30 ° C. and the detector was measured at 306 nm using a VWD UV detector. The mobile phase was used with varying ratios of methanol and phosphoric acid (pH 2.5), with a flow rate of 1 ml / min.
위의 방법으로 측정한 결과, 80%의 에탄올 추출물의 페놀 프로파일(phenol profile)은 클로로겐산이 8.04 mg/g으로 가장 높은 함량을 나타났으며, 다음으로는 로즈마릭산이 0.16 mg/g, 카페인산이 0.06 mg/g 순으로 검출되었다. 그 결과를 하기 표 2에 나타내었다.The phenol profile of the 80% ethanol extract showed the highest content of chlorogenic acid (8.04 mg / g), followed by rosemaric acid (0.16 mg / g) and caffeic acid. It was detected in order of 0.06 mg / g. The results are shown in Table 2 below.
실시 예 4 Example 4
뽕잎 추출물의 정제Purification of Mulberry Leaf Extract
가. 세파텍스(Sephadex) LH-20에 의한 분획end. Fraction by Sephadex LH-20
뽕잎 추출물로부터 페놀성 물질을 분획하기 위하여 세파텍스(Sephadex) LH-20 컬럼(column)을 사용하여 60%의 에탄올로 실시 예 1의 방법과 같이 용출시킨 결과, 주 피크(peak) 하나와 작은 피크 2개로 분획되었으며, 헬리코박터 파이로리에 대한 저해 활성은 하기 표 3에서와 같이 주 피크에서 나타나 분획물 중, 주 피크에 해당하는 분획물만 모아서, 농축, 동결건조시켜 정제에 사용하였다.In order to fractionate phenolic substance from the mulberry leaf extract, eluting with 60% ethanol in the same manner as in Example 1 using Sephadex LH-20 column, one main peak and one small peak were obtained. Fractionated into two, inhibitory activity against Helicobacter pylori appeared in the main peak as shown in Table 3 below, only the fractions corresponding to the main peak of the fractions collected, concentrated, lyophilized and used for purification.
나. C18 칼럼(column) 및 MCI-gel CHP-20 칼럼(column)에 의한 정제I. Purification by C 18 column and MCI-gel CHP-20 column
세파덱스(Sephadex) LH-20 분획물 중 활성분획을 농축하여 도 2와 같이, C18 칼럼(Flash cartridge)을 사용하여 역상 타입(revers phase type)인 에탄올 0%에서 100%로 용액의 농도를 증가시키며 20 ㎖/min의 유속으로 검출기(Detector) (UV-VIS, UV-9000, Eyela)를 사용하여 분획하였다. 그 결과 도 2와 같이 9개의 분획물로 분리되었다. 각 분획물의 페놀 함량은 하기 표 4에서와 같이 분획물 1이 147.4ㅁ0.3㎍/㎖, 분획물 2는 232.3ㅁ2.7㎍/㎖, 분획물 3은 224.7ㅁ1.8㎍/㎖, 분획물 4는 235.4ㅁ0.2㎍/㎖, 분획물 5는 196.1ㅁ2.5㎍/㎖, 분획물 6은 150.0ㅁ0.4㎍/㎖, 분획물 7은 126.1ㅁ2.5㎍/㎖, 분획물 8은 81.5ㅁ0.4㎍/㎖, 분획물 9는 68.9ㅁ25㎍/㎖의 페놀 함량을 나타내었다. 또한 각 분획물 1∼9의 9종을 사용하여 디스크 방법(disc method)를 이용한 H. pylori의 저해활성 실험을 한 결과, 하기 표 4와 도 2에서와 같이 분획물 7과 분획물 8에서 11㎜와 12㎜의 클리어 영역(clear zone)이 형성하여 단일물질로 분리하기 위하여 분획물 7 및 8을 다시 MCI-gel CHP-20 column을 이용하여 정상 상 타입(Normal phase type)인 에탄올 100%에서 0%로 농도를 감소시키며 10㎖/min의 유속 용출한 결과, 9개의 단일 물질 분획을 얻을 수 있었으며, 각 분획물은 TLC에 의한 Rf치에 의해 화합물 A∼F까지 6개의 물질로 분류하였고, 각 단일 분획물은 HPLC로 순도 검정을 하여 단일물질임을 확인하였다(도 3 참조).Concentrate the active fraction in Sephadex LH-20 fraction and increase the concentration of the solution from 0% to 100% of ethanol, a reverse phase type, using a C 18 column (Flash cartridge) as shown in FIG. And fractionated using a detector (UV-VIS, UV-9000, Eyela) at a flow rate of 20 ml / min. As a result, it was separated into nine fractions as shown in FIG. The phenol content of each fraction is 147.4 W 0.3 μg / mL in
다. 정제물의 헬리코박터 파이로리 균에 대한 저해효과All. Inhibitory Effect on Purified Helicobacter Pylori
정제물질인 화합물 A, B, C, D, E 및 F를 이용하여 헬리코박터 파이로리 균에 대한 항균효과를 알아보기 위해 디스크 방법(disc method)로 측정한 결과, 하기 표 5에서와 같이 화합물 A, B, C, D, E 및 F를 단일물질로 헬리코박터 파이로리 균에 처리하였을 때, 디스크 방법에 의한 클리어 영역(clear zone)이 매우 약하게 형성되었으며, 200㎍ 페놀/100㎕의 농도로 화합물 B와 C, 화합물 C와 F, 화합물 B와 F를 혼합하여 처리했을 경우에 헬리코박터 파이로리 균에 대한 항균력이 13㎜, 14㎜, 13㎜의 클리어 영역을 형성하는 것을 관찰할 수 있었고, 화합물 B, C 및 F 3가지를 같이 혼합하여 처리하였을 때 16㎜ 가까운 클리어 영역이 형성되어 저해활성이 높아지는 것을 알 수 있었다. 또한 화합물 A와 E 단일물질 처리시와 화합물 A나 E가 혼합된 실험군에서는 클리어 영역이 검출되지 않았다. 이러한 결과로 볼 때 뽕잎 추출물에서도 단일 물질에 의해 헬리코박터 파이로리 균의 저해를 일으키기 보다는 2종 이상의 다중 물질에 의한 시너지 효과에 의해서 헬리코박터 파이로리 균에 대한 저해가 나타난다고 판단된다. 이러한 현상은 분리된 페놀성분(simple phenol)들이 헬리코박터 파이로리 균의 세포벽(cell wall)을 단일 성분보다 효율적으로 공격하는 것으로 판단된다.In order to determine the antimicrobial effect of Helicobacter pylori bacteria using the purified compounds A, B, C, D, E and F, as a result of the disk method (disc method), as shown in Table 5 Compound A, B When C, D, E and F were treated with Helicobacter pylori bacteria as a single substance, the clear zone was very weakly formed by the disk method, and the compounds B, C, When compound C and F and compound B and F were mixed and treated, it was observed that the antimicrobial activity against Helicobacter pylori bacteria formed clear areas of 13 mm, 14 mm, and 13 mm, and the compounds B, C, and
1): Not detected1): Not detected
라. 화합물 B의 구조 동정la. Structure Identification of Compound B
화합물 B는 녹는점(melting point)이 208℃이며, 음(negative)의 FAB-MS에서 354의 분자량을 얻었다. IR 스펙트럼은 3250에서 OH기가 1710에서 COO기가 확인되었으며, 선광도는 -35.2를 나타내었다. 1H-NMR 스펙트럼은 2.10 ppm(dd, J=10,12 Hz), 2.12 ppm(m), 2.26 ppm(ddd, J=2, 4, 12 Hz), 3.76 ppm(dd, J=2, 9 Hz-H), 4.22 ppm(m) 및 5.38 ppm(ddd, J=4, 9, 10 Hz), 6.29 ppm(d, J=16 Hz), 6.87 ppm(d, J=8 Hz). 7.02 ppm(d, J=12 Hz) 및 7.18 ppm(d, J=2 Hz) 등으로 정제된 화합물 B는 클로로겐산으로 동정하였다.Compound B had a melting point of 208 ° C. and a molecular weight of 354 in negative FAB-MS. The IR spectrum showed an OH group at 3250 and a COO group at 1710, and the photoluminescence was -35.2. The 1 H-NMR spectrum is 2.10 ppm (dd, J = 10,12 Hz), 2.12 ppm (m), 2.26 ppm (ddd, J = 2, 4, 12 Hz), 3.76 ppm (dd, J = 2, 9 Hz-H), 4.22 ppm (m) and 5.38 ppm (ddd, J = 4, 9, 10 Hz), 6.29 ppm (d, J = 16 Hz), 6.87 ppm (d, J = 8 Hz). Compound B purified to 7.02 ppm (d, J = 12 Hz) and 7.18 ppm (d, J = 2 Hz) was identified as chlorogenic acid.
1H-NMR : δ: 2.10 (1H, dd, J=10, 12 Hz, 2-H), 2.12(m, 6-H), 2.26(1H, ddd, J=2, 4, 12 Hz, 2-H), 5.38(1H, ddd, J=4, 9, 10 Hz, 3-H), 3.76(1H, dd, J=2, 9 Hz, 4-H), 4.22(m, 5-H), 6.29(1H, d, J=16 Hz, olefin alpha), 6.87(1H, d, J=8 Hz, 5-H). 7.02(1H, d, J=12 Hz, 6-H), 7.18(1H, d, J=2 Hz, 2-H) 1 H-NMR: δ: 2.10 (1H, dd, J = 10, 12 Hz, 2-H), 2.12 (m, 6-H), 2.26 (1H, ddd, J = 2, 4, 12 Hz, 2 -H), 5.38 (1H, ddd, J = 4, 9, 10 Hz, 3-H), 3.76 (1H, dd, J = 2, 9 Hz, 4-H), 4.22 (m, 5-H) , 6.29 (1H, d, J = 16 Hz, olefin alpha), 6.87 (1H, d, J = 8 Hz, 5-H). 7.02 (1H, d, J = 12 Hz, 6-H), 7.18 (1H, d, J = 2 Hz, 2-H)
13C-NMR: δ: 176.4, 168.2, 149.3, 146.6, 127.5, 122.9, 116.6, 115.6, 115.3, 76.2, 73.5, 71.7, 71.4, 39.1, 38.0 13 C-NMR: δ: 176.4, 168.2, 149.3, 146.6, 127.5, 122.9, 116.6, 115.6, 115.3, 76.2, 73.5, 71.7, 71.4, 39.1, 38.0
마. 화합물 C의 구조 동정hemp. Structure Identification of Compound C
화합물 C는 녹는점이 161∼164℃이며, 음의 FAB-MS에서 분자량 180을 얻었다. IR 스펙트럼은 3440에서 OH기가 1646에서 COOH가 확인되었으며, 또한 6.08 ppm(d, J=16 Hz), 아로마틱(aromatic) 영역에서 3H분의 6.73∼6.97 ppm(m) 및 7.39 ppm(d, J=16 Hz) 등의 1H-NMR 스펙트럼과 13C-NMR의 스펙트럼은 카페인산으로 동정하였다.(Fig. 9~13)Compound C had a melting point of 161 to 164 ° C and obtained a molecular weight of 180 by negative FAB-MS. IR spectra showed OH groups at 3440 and COOH at 1646. Also, 6.08 ppm (d, J = 16 Hz), 6.73-6.97 ppm (m) and 7.39 ppm (d, J = 3H) in the aromatic region. 1H-NMR spectra and 13C-NMR spectra were identified as caffeic acid (Fig. 9 ~ 13).
1H-NMR: δ: 6.08(1H, d, J=16 Hz, alpha-H), 6.73~6.97(3H,m,aromatic-H), 7.39(1H, d, J=16 Hz, beta-H) 1 H-NMR: δ: 6.08 (1H, d, J = 16 Hz, alpha-H), 6.73-6.97 (3H, m, aromatic-H), 7.39 (1H, d, J = 16 Hz, beta-H )
13C-NMR: δ: 113.9, 114.8, 115.3, 120.9, 126.0, 144.5, 144.9, 147.3, 13 C-NMR: δ: 113.9, 114.8, 115.3, 120.9, 126.0, 144.5, 144.9, 147.3,
168.4 168.4
바. 화합물 F의 구조 동정bar. Structure Identification of Compound F
화합물 F는 녹는점이 204℃이고 선광도는 +145ㅀ이며, 음의 FAB-MS에서 360의 분자량을 얻었다. 1H-NMR 스펙트럼은 2.18 ppm(d, J=8 Hz), 5.08 ppm(m), 6.14 ppm(d, J=16 Hz), 6.52 ppm(d, J=8 Hz), 6.63 ppm(d, J=8 Hz), 6.69 ppm(s), 6.74 ppm(d, J=8 Hz), 6.83 ppm(d, J=8 Hz), 6.98 ppm(s) 및 7.42 ppm(d, J=16 Hz) 등으로 로즈마릭산으로 동정하였다.Compound F had a melting point of 204 DEG C and a photoluminescence of +145 GPa and a molecular weight of 360 was obtained in negative FAB-MS. 1 H-NMR spectra were 2.18 ppm (d, J = 8 Hz), 5.08 ppm (m), 6.14 ppm (d, J = 16 Hz), 6.52 ppm (d, J = 8 Hz), 6.63 ppm (d, J = 8 Hz), 6.69 ppm (s), 6.74 ppm (d, J = 8 Hz), 6.83 ppm (d, J = 8 Hz), 6.98 ppm (s) and 7.42 ppm (d, J = 16 Hz) Rosemaric acid was identified as the back.
1H-NMR : δ: 2.18(2H, brs 5.08, 11-H), 6.52(1H, m, 10-H), 6.14(1H, d, J=16 Hz, 8-H), 6.52(1H, d, J=8 Hz, 17=H), 6.63(1H, d, J=8 Hz, 16-H), 6.69(1H, s, 13-H), 6.74(1H, 5-H), 6.83(1H, d, J=8 Hz, 6-H), 6.98(1H, s, 2-H), 7.42(1H, d, J=16 Hz, 7-H). 1 H-NMR: δ: 2.18 (2H, brs 5.08, 11-H), 6.52 (1H, m, 10-H), 6.14 (1H, d, J = 16 Hz, 8-H), 6.52 (1H, d, J = 8 Hz, 17 = H), 6.63 (1H, d, J = 8 Hz, 16-H), 6.69 (1H, s, 13-H), 6.74 (1H, 5-H), 6.83 ( 1H, d, J = 8 Hz, 6-H), 6.98 (1H, s, 2-H), 7.42 (1H, d, J = 16 Hz, 7-H).
13C-NMR: δ: 36.2, 72.6, 113.2, 114.2, 115.1, 115.4, 116.4, 119.9, 121.2, 125.4, 127.3, 143.6, 144.5, 145.2, 145.5, 148.1, 165.8, 170.9 13 C-NMR: δ: 36.2, 72.6, 113.2, 114.2, 115.1, 115.4, 116.4, 119.9, 121.2, 125.4, 127.3, 143.6, 144.5, 145.2, 145.5, 148.1, 165.8, 170.9
도 1은 에탄올 농도에 따른 뽕잎으로부터 페놀성 물질의 추출량을 나타낸 그래프이다.1 is a graph showing the extraction amount of phenolic substances from mulberry leaves according to the ethanol concentration.
도 2는 본 발명에 따라 뽕잎 추출물로부터 페놀성 물질의 분리 공정도이다.Figure 2 is a separation process of the phenolic substance from the mulberry leaf extract in accordance with the present invention.
도 3은 본 발명에 따라 정제된 화합물의 HPLC 디아그램으로, 도 3a는 화합물 B에 대한 HPLC 디아그램이고, 도 3b는 화합물 C에 대한 HPLC 디아그램이며, 도 3c은 화합물 F에 대한 HPLC 디아그램이다.FIG. 3 is an HPLC diagram of a compound purified according to the present invention, FIG. 3a is an HPLC diagram for compound B, FIG. 3b is an HPLC diagram for compound C, and FIG. 3c is an HPLC diagram for compound F to be.
Claims (4)
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