KR100388357B1 - Antimicrobial Active Compound Isolated from the Leaves and Stems of Hovenia dulcis Thunb and Isolation Method Thereof - Google Patents
Antimicrobial Active Compound Isolated from the Leaves and Stems of Hovenia dulcis Thunb and Isolation Method Thereof Download PDFInfo
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Abstract
본 발명은 헛개나무(Hovenia dulcisThunb)의 줄기와 잎에서 분리한 천연항균활성물질 및 그의 분리방법에 관한 것이다. 보다 상세하게는 헛개나무의 어린 줄기를 포함한 잎으로부터 피리딘 골격 구조를 갖는 호베니딘 B6 (hovenidine B6)로 명명한 천연항균활성물질을 발견하였다.The present invention relates to a natural antimicrobial active material isolated from the stems and leaves of the Hovenia dulcis Thunb and a method for separating the same. More specifically, a natural antimicrobial active substance named hobenidine B6 having a pyridine skeleton structure was found from the leaves including the young stems of the larvae.
헛개나무의 줄기와 잎을 열수로 추출하여 얻어진 물추출물을 동결건조한 다음, 메탄올로 용해하여 얻어진 메탄올 가용 추출물을 농축하여 메탄올을 제거하고, 용매분획, 실리카겔 흡착 컬럼 크로마토그라피, 세파덱스 LH-20 컬럼 크로마토그라피, 옥타데실실란 컬럼 크로마토그라피, HPLC등의 단계를 거쳐 최종적으로 호베니딘 B6를 단리하였으며 호베니딘 B6의 구조는 MS, NMR 분석에 의해 결정되었다.After extracting the stem and leaves of the bark tree with hot water, the water extract obtained was lyophilized. Then, the methanol soluble extract obtained by dissolving with methanol was concentrated to remove methanol. Solvent fractionation, silica gel adsorption column chromatography, Sephadex LH-20 column Chromatography, octadecyl column column chromatography, HPLC and the like were finally isolated and the homobenidine B6 structure was determined by MS, NMR analysis.
본 발명의 호베니딘 B6는 새로운 천연 항균제로 식품 및 약품으로 이용될 수 있을 뿐만 아니라 다양한 활성물질 유도체의 선도물질(lead compound)로써의 이용등 광범위한 용도를 제공하게 될 것이다.Hovenidine B6 of the present invention may be used as food and medicine as a novel natural antimicrobial agent, and will provide a wide range of uses, such as the use of various active substance derivatives as lead compounds.
Description
본 발명은 헛개나무의 줄기와 잎에서 분리한 항균물질인 호베니딘 B6 및 그의 분리방법에 관한 것이다. 보다 상세하게는 헛개나무의 어린 줄기를 포함한 잎으로부터 피리딘 골격 구조를 갖는 호베니딘 B6 (hovenidine B6)로 명명한 천연항균활성물질을 발견하였다.The present invention relates to a hivenidine B6 and an isolation method thereof, which is an antimicrobial substance isolated from the stems and leaves of the larvae. More specifically, a natural antimicrobial active substance named hobenidine B6 having a pyridine skeleton structure was found from the leaves including the young stems of the larvae.
헛개나무는 우리 나라의 산야에 자생 또는 재배되고 있는 식물로 잎을 구토, 주독 제거의 목적으로 전즙하여 음용하였으며[신민교, 정보섭; 도해 향약(생약) 대사전(식물편), p 291, 영림사, 1990], 간독소해독물질로 (+)-ampelopsin [Hase-K, Ohsugi-M 등; Biological Pharmaceutical Bulletin, 20(4), p 381-385, 1997]이 보고된 바 있다.Barn tree is a plant native to Korea or cultivated in the field of Korea, and its leaves are juiced for the purpose of vomiting and eliminating poisoning. Illustrated Herbal Medicine (Medicinal Herbs) Metabolism (Plant), p 291, Younglimsa, 1990], (+)-ampelopsin [Hase-K, Ohsugi-M, etc .; Biological Pharmaceutical Bulletin, 20 (4), p 381-385, 1997.
본 발명과 관련된 종래의 논문은, 헛개나무의 줄기와 잎에 함유된 항균 및 항산화 물질로 페룰릭산(ferulic acid)과 바닐릭산(vanillic acid)의 존재를 발명자들이 보고(한국식품과학회 제 64차 학술발표회, p 308, 2000년 5월)한 바 있으나, 헛개나무에서 본 발명의 항균활성물질인 호베니딘 B6에 관한 보고는 없다.Conventional papers related to the present invention report the presence of ferulic acid and vanillic acid as antimicrobial and antioxidant substances contained in the stems and leaves of the bark tree. Presentation, p 308, May 2000), but there is no report on the hivenidine B6, the antimicrobial active substance of the present invention in the bark.
본 발명은 헛개나무(Hovenia dulcisThunb)의 줄기와 잎에서 피리딘 골격 구조를 갖는 호베니딘 B6 (hovenidine B6)로 명명한 천연항균활성물질을 분리하고 구조결정을 함으로써 새로운 천연의 항균활성물질을 발견하였다.The present invention finds a new natural antimicrobial active substance by separating and structuring a natural antimicrobial active substance named hobenidine B6 having a pyridine skeleton in the stem and leaves of Hovenia dulcis Thunb. It was.
본 발명은 헛개나무의 줄기와 잎을 열수추출하여 얻어진 물추출물을 동결건조한 다음, 메탄올로 용해하여 얻어진 메탄올 가용 추출물을 농축하여 메탄올을 제거하고, 용매분획, 실리카겔 흡착 컬럼 크로마토그라피, 세파덱스 LH-20 컬럼 크로마토그라피, 옥타데실실란 컬럼 크로마토그라피, HPLC등의 단계를 거쳐 최종적으로 호베니딘 B6를 단리하였으며, 호베니딘 B6의 구조는 MS, NMR 분석에 의해 결정되었다.The present invention freeze-dried the water extract obtained by hot water extraction of the stem and leaves of the bark, and then concentrated by methanol soluble extract obtained by dissolving with methanol to remove methanol, solvent fractions, silica gel adsorption column chromatography, Sephadex LH- Hobenidine B6 was finally isolated through 20 column chromatography, octadecyl column chromatography, HPLC, and the like. The structure of hobenidine B6 was determined by MS and NMR analysis.
이하, 하기 실시예에 의거하여 본 발명을 구체적으로 설명한다.Hereinafter, the present invention will be specifically described based on the following examples.
(실시예 1) 천연항균활성물질 호베니딘 B6의 분리Example 1 Isolation of Natural Antibacterial Active Material Hobenidine B6
헛개나무(Hovenia dulcisThunb)는 전라남도 보성군에서 재배된 식물로, 6월에 어린 줄기를 포함한 잎을 채취하여 음건한 후, 분쇄기 (BM-2 Nissei bio-mixer, Nihonseiki Kaiseiki LTD, Tokyo, Japan)로 분쇄하여 시료로 사용하였다. 이 시료(1.3 kg)를 열수추출(70-99℃, 15분)하여 원심분리(959x g, 15분; VS-30000MT, Vision, Seoul, Korea)한 후, 얻어진 상등액을 동결건조(FDU-500, Eyela, Tokyo, Japan)하여 분말화된 물추출물(164 g)을 얻었다. 이를 메탄올 (5 L)로 녹이고 여과하여 얻어진 여액을 38℃에서 감압농축하여 메탄올이 제거된 메탄올 가용추출물(48 g)을 얻었다. Hovenia dulcis Thunb is a plant cultivated in Boseong-gun, Jeollanam-do, in June. It was ground and used as a sample. This sample (1.3 kg) was subjected to hot water extraction (70-99 ° C., 15 minutes) and centrifuged (959x g, 15 minutes; VS-30000MT, Vision, Seoul, Korea), and the obtained supernatant was lyophilized (FDU-500). , Eyela, Tokyo, Japan) to obtain a powdered water extract (164 g). This was dissolved in methanol (5 L) and the filtrate was filtered and concentrated under reduced pressure at 38 ℃ to obtain a methanol soluble extract (48 g) from which methanol was removed.
메탄올 가용 추출물을 에칠아세테이트와 완충 용액(0.2 M glycine-0.2 MHCl, pH 3)으로 수상 획분과 에칠아세테이트 가용 산성·중성 획분(EtOAc-soluble acidic·neutral fraction)으로 분획하였다. 에칠아세테이트 가용 산성·중성 획분을 완충 용액(0.2 M Na2HPO4-0.2 M NaH2PO4, pH 8)으로 분배하여 에칠아세테이트 가용 중성 획분(EtOAc-soluble neutral fraction)과 수상 획분으로 분획하였고, 얻어진 수상 획분에 0.1 N HCl을 가하여 pH 3.0으로 조절한 후 에칠아세테이트로 분배하여 에칠아세테이트 가용 산성 획분(EtOAc-soluble acidic fraction)과 수상획분으로 분획하였다. 얻어진 획분의 항균활성을 페이퍼 디스크법(Zaika, L.L.,J.food safety, 9, p 97-118 , 1988)으로 스트렙토코코스 아우레우스(Staphylococcus aureus)와 에스체리치아 코리(Escherichia coli)를 사용하여 검정한 결과, 에칠아세테이트 가용 산성획분은 항균활성을 나타냈으며, 이후 활성물질의 정제과정에서의 항균활성검정은 스트렙토코코스 아우레우스에 대한 활성여부를 검정하여 수행하였다.The methanol soluble extract was fractionated into an aqueous fraction and an ethyl acetate soluble acidic and neutral fraction (EtOAc-soluble acidic and neutral fraction) with an ethyl acetate and a buffer solution (0.2 M glycine-0.2 MHCl, pH 3). The ethyl acetate soluble acidic and neutral fractions were partitioned into a buffer solution (0.2 M Na 2 HPO 4 -0.2 M NaH 2 PO 4 , pH 8) and fractionated into an ethyl acetate soluble neutral fraction (EtOAc-soluble neutral fraction) and an aqueous phase fraction. 0.1 N HCl was added to the obtained aqueous fraction to adjust the pH to 3.0, and then partitioned into ethyl acetate and fractionated into an ethyl acetate soluble acidic fraction (EtOAc-soluble acidic fraction) and an aqueous phase fraction. The antimicrobial activity of the obtained fractions was analyzed by the paper disk method (Zaika, LL, J. food safety , 9, p 97-118, 1988) using Streplococcus aureus and Escherichia coli . As a result, the ethyl acetate soluble acid fraction showed antimicrobial activity, and the antimicrobial activity assay during the purification of the active substance was performed by assaying the activity against Streptococcus aureus.
에칠아세테이트 가용 산성획분(1.9 g)을 실리카겔 흡착 컬럼 크로마토그라피를 이용하여 에칠아세테이트 용액에서 메탄올 농도를 점진적으로 높여 용출분획한 결과, 활성은 에칠아세테이트-메탄올(100:0, v/v)획분에 나타나, 활성획분 1.1 g이 얻어졌다. 이어 이 활성물질을 세파덱스 LH-20 컬럼 크로마토그라피(이동상: 메탄올-크로로포름, 4:1, v/v)에 의하여 분획하였다. 활성은 Ve/Vt (elutionvolume/column bed volume) 0.80∼0.96의 위치에서 용출된 획분에서 활성이 나타났다. 이 활성획분(322 mg)은 옥타데실실란 컬럼 크로마토그라피(이동상: 메탄올-물)로 정제하였다. 메탄올-물의 50:50 (v/v) 획분에서 활성 획분(263 mg)을 얻었다. 이어 이 획분은 역상컬럼을 탑재한 HPLC (Senshu pak, 70% 메탄올)에 의해 미황색의 분말형태로 254 mg을 성공적으로 단리(isolation)하였으며 이 물질을 호베니딘 B6로 명명하였다. 스트렙토코코스 아우레우스에 대한 성장억제 활성은 6 mm 페이퍼디스크에 800 ㎍의 호베니딘 B6를 제공할 때 생육억제환의 크기는 14 mm로 나타났다. 같은 조건에서 대조군으로 사용한 벤조산(200 ㎍)은 10 mm의 억제효과를 나타냈다.Elution fractionation of ethyl acetate soluble acid fraction (1.9 g) with silica gel adsorption column chromatography gradually increased the methanol concentration in the ethyl acetate solution. It showed, and the active fraction 1.1g was obtained. This active material was then fractionated by Sephadex LH-20 column chromatography (mobile phase: methanol-chloroform, 4: 1, v / v). The activity was found in the fraction eluted at the position of Ve / Vt (elutionvolume / column bed volume) 0.80-0.96. This active fraction (322 mg) was purified by octadecyl column column chromatography (mobile phase: methanol-water). An active fraction (263 mg) was obtained in a 50:50 (v / v) fraction of methanol-water. This fraction was then successfully isolated by 254 mg of a pale yellow powder by HPLC with reversed phase column (Senshu pak, 70% methanol), which was named Hobenidine B6. Growth inhibitory activity against Streptococcus aureus showed that the growth inhibitory ring size was 14 mm when 800 μg of Hobenidine B6 was supplied to 6 mm paper disk. Benzoic acid (200 μg) used as a control under the same conditions showed an inhibitory effect of 10 mm.
(실시예 2) 기기분석에 의한 호베니딘 B6의 구조결정Example 2 Structure Determination of Hobenidine B6 by Instrumental Analysis
호베니딘 B6의 구조를 결정하기 위하여 질량분석기(MS, Jeol JNM-AX 505 WA)의해 측정된 호베니딘 B6의 질량분석치는 분자이온인 M+가m/z171로 측정되었으며, 고분해 질량분석에 의해 분석된 분자식은 C7H9O4N1로 측정되었다. 또한 스펙트로포토메타(Jasco U550)에 의해 측정된 λmax (메탄올)를 나타내는 파장은 235 nm이었다.The mass spectrometry of hobenidine B6 measured by mass spectrometer (MS, Jeol JNM-AX 505 WA) to determine the structure of hobenidine B6 was measured by the molecular ion M + of m / z 171, high resolution mass The molecular formula analyzed by analysis was determined as C 7 H 9 O 4 N 1 . Moreover, the wavelength which shows (lambda) max (methanol) measured by the spectrophotometer (Jasco U550) was 235 nm.
기기(Jeol LNM-LA 400)에 의해 분석된1H-NMR (400MHz, CD3OD)의 측정값은 δ6.92(s,1H, H-5), 3.89(s, 2H, C-4-CH2), 3.67(s, 3H, C-6-OCH3)이며,13C-NMR(100MHz, CD3OD)에 의해 분석된 측정값은 δ172.46(C-6), 168.96(C-3),168.28(C-2), 141.22(C-4), 130.71(C-5), 52.50(C-6-OCH3), 33.63(C-4-CH2)이었다.Measurements of 1 H-NMR (400 MHz, CD 3 OD) analyzed by instrument (Jeol LNM-LA 400) were δ6.92 (s, 1H, H-5), 3.89 (s, 2H, C-4- CH 2 ), 3.67 (s, 3H, C-6-OCH 3 ), and the measured values analyzed by 13 C-NMR (100 MHz, CD 3 OD) were δ 172.46 (C-6), 168.96 (C- 3), 168.28 (C-2), 141.22 (C-4), 130.71 (C-5), 52.50 (C-6-OCH 3 ), and 33.63 (C-4-CH 2 ).
이상의 MS,1H-NMR,13C-NMR등의 기기분석결과로부터 호베니딘 B6의 구조를 하기와 같이 결정하였다.From the results of the instrumental analysis of MS, 1 H-NMR, and 13 C-NMR, the structure of hobenidine B6 was determined as follows.
호베니딘 B6의 구조Structure of Hobenidine B6
(실시예 3) 호베니딘 B6의 항균활성 검정Example 3 Antibacterial Activity Assay of Hobenidine B6
실시예 1에서 기술한 방법으로 헛개나무의 줄기와 잎에서 단리된 호베니딘 B6의 항균활성검정을 페이퍼 디스크법(Zaika, L.L.,J.Food safety, 9, p 97-118, 1988)으로 실시하였다. 즉, 푸어 플레이트 방법(pour-plate method)에 의해 45℃로 조절된 멸균배지 15 mL에 스타필로코코스 아우레우스(Staphylococcus aureusATCC 5383)와 에스체리치아 코리(Escherichia coliATCC 10563)의 전배양액 0.1 mL를 혼합시킨 후 페트리디시에 넣고 응고시킨 다음, 6 mm의 페이퍼 디스크에 올리고 0.85% 식염수로 확산시켜 30℃에서 16시간 배양하여 생육저해환의 크기(mm)로 효과를 측정하였다. 배지는 뉴트리언트 (Nutrient) 배지(Difco)를 사용하였으며, 동일조건에서 벤조산(benzoic acid)을 대조구로 사용하였다. 얻어진 결과는 표 1과 같다.Example 1 No. Benny Dean B6 paper disk method for antibacterial activity of a test method described was isolated from the stem and leaves of a tree in heotgae (Zaika, LL, J. Food safety, 9, p 97-118, 1988) carried out with It was. In other words, the pre-culture of Staphylococcus aureus ATCC 5383 and Escherichia coli ATCC 10563 in 15 mL of sterile medium adjusted to 45 ° C. by the pour-plate method. After mixing the mL and put the petri dish into the coagulation, and then placed on a 6 mm paper disk, and diffused with 0.85% saline and incubated for 16 hours at 30 ℃ to measure the effect (mm) of growth inhibition ring. Nutrient medium (Difco) was used as the medium, and benzoic acid was used as a control under the same conditions. The obtained results are shown in Table 1.
[표 1] 스타필로코코스 아우레우스와 에스체리치아 코리에 대한 호베니딘 B6의 항균활성Table 1 Antimicrobial Activity of Hobenidin B6 against Staphylococcus aureus and Escherichia Cory
즉, 호베니딘 B6는 그람양성세균인 스타필로코코스 아우레우스 및 그람음성세균인 에스체리치아 코리에 대해 항균활성을 나타냈다.In other words, Hobenidine B6 showed antimicrobial activity against Gram-positive bacteria Staphylococcus aureus and Gram-negative bacteria Escherichia cori.
본 발명의 헛개나무의 줄기와 잎에서 천연항균활성물질로 분리되고 구조결정된 호베니딘 B6는 새로운 천연항균제로 식품 및 약품에 이용될 수 있으며, 호베니딘 B6는 특이한 구조를 갖는 천연항균활성물질이어서 다양한 활성물질의 선도물질(lead compound)로 사용이 기대된다.Hobenidine B6 isolated and structured as a natural antimicrobial active material from the stems and leaves of the bark of the present invention can be used in food and medicine as a new natural antimicrobial agent, Hobenidine B6 is a natural antimicrobial active material having a specific structure Subsequently, it is expected to be used as a lead compound of various active substances.
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