KR100341795B1 - Aspaoligonin - Google Patents

Aspaoligonin Download PDF

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KR100341795B1
KR100341795B1 KR1019990033413A KR19990033413A KR100341795B1 KR 100341795 B1 KR100341795 B1 KR 100341795B1 KR 1019990033413 A KR1019990033413 A KR 1019990033413A KR 19990033413 A KR19990033413 A KR 19990033413A KR 100341795 B1 KR100341795 B1 KR 100341795B1
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formula
meoh
compound
namokdae
fraction
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KR20010017748A (en
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김금숙
박창기
성재덕
김현태
한상익
곽용호
임무상
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대한민국(관리청:특허청장, 승계청:농촌진흥청장)
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Abstract

본 발명은 방울비짜루(남옥대)로부터 단리되어 천연에서 처음으로 보고되는 물질(Aspaoligonin)에 관한 것이다.The present invention relates to a substance (Aspaoligonin), which is first isolated from nature and isolated from the droplets.

Description

방울비짜루(남옥대)로부터 단리되는 신물질인 아스파올리고닌 {ASPAOLIGONIN}Aspaolinogine, a new substance isolated from nambidae (Namokdae) {ASPAOLIGONIN}

본 발명은 방울비짜루(남옥대)로부터 천연에서 처음으로 단리, 보고되는 물질 아스파올리고닌(Aspaoligonin)에 관한 것이다.FIELD OF THE INVENTION The present invention relates to the substance Aspaoligonin, which is first isolated and reported from nature from Nabidaeru (Namokdae).

방울비짜루(Asaragus oligoclonosMaxim.)는 백합과에 속하는 다년생 초본으로 약간 육질인 뿌리줄기를 약용으로 쓰며 예로부터 해수, 천식 및 가래가 배출되는 증상에 사용하였다.(중국 본초도감, 려강출판사, 185p) 중국, 일본, 한국 및 러시아에 주로 분포하고 있으며 이 식물로부터 분리된 성분은 보고된 바 없다. Asaragus oligoclonos Maxim. Is a perennial herb belonging to the family Liliaceae, which has been used as a medicinal root stem for medicinal purposes and has been used for the discharge of seawater, asthma and sputum since ancient times (Chinese Herbs, Ryeo Kang Publishing Co., 185p). It is mainly distributed in China, Japan, Korea, and Russia, and no component has been reported from this plant.

이에 본 발명자들은 방울비짜루(남옥대)로부터 지금까지 천연에서 보고 되지 않은 새로운 스테로이드계 사포닌(Steroid Saponin) 1종을 단리하였다. 단리된 화합물은 분광학적 방법으로 그 구조를 확인하였다.Therefore, the present inventors have isolated a new type of steroid-based saponin (Steroid Saponin) that has not been reported in nature so far from the drops of bizarre (Namokdae). Isolated compounds were identified for their structure by spectroscopic methods.

본 발명은 상기한 바와 같이 동작되는 종래 기술의 문제점을 해결하기 위하여 창안된 것으로서, 본 발명의 주 목적은 아스파올리고닌을 추출하려는데 있다.The present invention has been made to solve the problems of the prior art operating as described above, the main object of the present invention is to extract aspa oligonin.

도 1 은 아스파올리고닌의 화학 구조도이고,1 is a chemical structural diagram of aspaoligonin,

도 2 는 화학식 1의 화합물의 질량분석스펙트럼도1이고,2 is a mass spectrometry diagram of the compound of Formula 1;

도 3 은 화학식 1의 화합물의 질량분석스펙트럼도2이고,3 is a mass spectrometry diagram of the compound of Formula 1;

도 4 는 화학식 1의 화합물의 적외선흡광도스펙트럼도이고,4 is an infrared absorbance spectrum diagram of a compound of Formula 1,

도 5 는 화학식 1의 화합물의 수소핵자기공명스펙트럼도1이고,5 is a hydrogen nuclear magnetic resonance spectrum of the compound of Formula 1, FIG.

도 6 은 화학식 1의 화합물의 수소핵자기공명스펙트럼도2이고,6 is a hydrogen nuclear magnetic resonance spectrum of the compound of Formula 1, FIG.

도 7 은 화학식 1의 화합물의 수소핵자기공명스펙트럼도3이고,7 is a hydrogen nuclear magnetic resonance spectrum of the compound of formula 1,

도 8 은 화학식 1의 화합물의 탄소핵자기공명스펙트럼도이고,8 is a carbon nuclear magnetic resonance spectrum diagram of a compound of Formula 1,

도 9 는 화학식 1의 화합물의 무변조증강극성전달스펙트럼(DEPT)도이고,9 is a diagram showing the modulation-free enhanced polarization spectrum (DEPT) of the compound of Formula 1,

도 10 은 화학식 1의 화합물의 수소-수소 상관성분광스펙트럼도110 is a hydrogen-hydrogen correlation component light spectrum diagram of the compound of Formula 1

(1H-1H COSY 1)이고,( 1 H- 1 H COSY 1),

도 11 은 화학식 1의 화합물의 수소-수소 상관성분광스펙트럼도211 is a hydrogen-hydrogen correlation component light spectrum diagram of the compound of Formula 1

(1H-1H COSY 2)이고,( 1 H- 1 H COSY 2),

도 12 는 화학식 1의 화합물의 헤테로핵다중양자상관성스펙트럼 112 is a heteronuclear multiproton correlation spectrum 1 of the compound of Formula 1;

(HMQC 1)도이고,(HMQC 1) degrees,

도 13 은 화학식 1의 화합물의 헤테로핵다중양자상관성스펙트럼 213 is a heteronuclear multiproton correlation spectrum 2 of the compound of Formula 1;

(HMQC 2)도이고,(HMQC 2) degrees,

도 14 는 화학식 1의 화합물의 헤테로핵다중결합연결스펙트럼 114 is a heteronuclear multiple bond linkage spectrum 1 of the compound of Formula 1;

(HMBC 1)도이고,(HMBC 1) degrees,

도 15 는 화학식 1의 화합물의 헤테로핵다중결합연결스펙트럼 215 is a heteronuclear multiple bond linkage spectrum 2 of the compound of Formula 1;

(HMBC 2)도이고,(HMBC 2) degrees,

도 16 은 화학식 1의 화합물을 추출하는 방법의 흐름도이다.16 is a flowchart of a method of extracting a compound of Formula 1;

본 발명은 방울비짜루(남옥대)로부터 단리되는, 화학식 1로 표시되는 아스파 올리고닌을 제공한다.The present invention provides an aspa oligonin represented by the formula (1), which is isolated from the droplet baviru (Namokdae).

<화학식 1><Formula 1>

이하 실시예를 통하여 본 발명을 더욱 상세히 설명한다. 그러나 하기의 실시예는 본 발명의 예시일 뿐이므로 본 발명이 하기의 실시예에 의하여 한정되는 것으로 간주되어서는 안된다.The present invention will be described in more detail with reference to the following examples. However, the following examples are only illustrative of the present invention and the present invention should not be considered to be limited by the following examples.

우선 방울비짜루로부터 아스파올리고닌을 단리하는 방법에 관하여 첨부된 도면 도 16을 참고로 하여 설명한다. 건조된 방울비짜루 뿌리줄기 3킬로그램을 분쇄(S100)하여 실온에서 메탄올(MeOH)을 사용하여 5회 추출(S110)하고 여과액을 모아 진공농축(S120)하여 1062그램의 추출물을 얻었다. 이 추출물을 증류수에 현탁하여 에테르(Et2O)로 3회 탈지(S130)한 후, 수층을 다시 수포화 부탄올(n-BuOH)를 사용하여 5회 추출(S140)하여 부탄올 분획 125그램을 얻었다. 부탄올 분획 30그램을 실리카겔 칼럼 크로마토그라피(용출제, CHCl3/MeOH/H2O (20:3:1 → 6:4:1), 기울기 용출)하여 20개의 분획으로 나누었고(S150), 이 중 5번째 분획은 세팍 C18(Sep-Pak C18)를 사용하여 (용출제, H2O→20%MeOH→100%MeOH, 기울기 용출) 정제(S160)한 후 최종 아스파올리고닌 94밀리그램(S170)을 순수하게 단리하였다.First, a method for isolating aspa-oligonin from the droplet bumblebee will be described with reference to the accompanying drawings of FIG. 16. Three kilograms of the dried beech root root stem was pulverized (S100), extracted five times using methanol (MeOH) at room temperature (S110), and the filtrate was collected and concentrated in vacuo (S120) to obtain 1062 grams of extract. The extract was suspended in distilled water, degreased three times with ether (Et 2 O) (S130), and the aqueous layer was extracted five times with saturated butanol (n-BuOH) (S140) to obtain 125 g of butanol fraction. . 30 g of butanol fraction was divided into 20 fractions by silica gel column chromatography (eluent, CHCl 3 / MeOH / H 2 O (20: 3: 1 → 6: 4: 1), gradient eluting) (S150) The fifth fraction was purified using Sepak C 18 (Sep-Pak C 18 ) (eluent, H 2 O → 20% MeOH → 100% MeOH, gradient elution) (S160) and then 94 mg (S170) of the final aspagogonine (S170). ) Was isolated purely.

이후 화학식 1의 화합물의 이화학적 특성에 대하여 설명한다.Hereinafter, the physicochemical properties of the compound of Formula 1 will be described.

방울비짜루 뿌리줄기에서 분리한 화학식 1의 화합물의 이화학적 특성은 다음과 같다.The physicochemical characteristics of the compound of Formula 1 isolated from the root bulge root are as follows.

물질의 상상은 흰색 가루상이다.The imagination of matter is white powdery.

분자량은 756(FAB+(high resolution),m/z:755.5675[M]+)Molecular weight is 756 (FAB + (high resolution), m / z : 755.5675 [M] + )

화학식 1의 화합물의 질량분석(MS) 스펙트럼은 도 2, 3에 제시하였다.Mass spectrometry (MS) spectra of the compounds of Formula 1 are shown in FIGS. 2 and 3.

본 화합물의 분자식은 C39H64O14로 표현되고, 녹는점은 238~243。C(분해)이다.The molecular formula of this compound is represented by C 39 H 64 O 14 , and has a melting point of 238 to 243 ° C. (decomposition).

비선광도[α]는 -5.4545。(c=0.22, 피리딘)이고, 적외선 흡광도는:3370(OH), 982, 917, 896, 850(인텐서티 917>896, 23S스피로케탈)이다. 화학식 1의 화합물의 적외선 흡광도 스펙트럼은 첨부된 도면 도 4에 제시되어있다.Specific light intensity [α] is -5.4545 ° (c = 0.22, pyridine), and infrared absorbance is : 3370 (OH), 982, 917, 896, 850 (Intensity 917> 896, 23 S spiroketal). Infrared absorbance spectra of the compound of Formula 1 are shown in the accompanying drawings, FIG. 4.

피리딘-d5을 용매로 하여 측정한 수소 핵자기공명 스펙트럼 결과는 다음과 같고, 표 1과 2에 화학식 1의 화합물의 각 수소에 대한 스펙트럼 데이터를 제시하였고, 도 5, 6, 7에 스펙트럼을 제시하였다.Hydrogen nuclear magnetic resonance spectra measured using pyridine-d 5 as a solvent are as follows. Tables 1 and 2 show spectral data for each hydrogen of the compound of Formula 1, and the spectra are shown in FIGS. 5, 6, and 7. Presented.

(피리딘-d5, δ):- 0.96(3H, s), 1.02(3H, s), 1.07(3H, d,J=7.08Hz), 1.23(3H, d,J=7.08Hz), 4.96(1H, d,J=7.32Hz, H-1 of inner glucose), 5.40(1H, d,J=7.80Hz, H-1 of terminal glucose)(Pyridine-d 5 , δ): 0.96 (3H, s), 1.02 (3H, s), 1.07 (3H, d, J = 7.08 Hz), 1.23 (3H, d, J = 7.08 Hz), 4.96 ( 1H, d, J = 7.32 Hz, H-1 of inner glucose), 5.40 (1H, d, J = 7.80 Hz, H-1 of terminal glucose)

피리딘-d5을 용매로 하여 측정한 비당부의 탄소 핵자기 공명 스펙트럼 결과는 다음과 같고, 표 1에 화학식 1의 화합물의 비당부의 각 탄소에 대한 스펙트럼 데이터를 제시하였다.Carbon nuclear magnetic resonance spectra of the non-sugar part measured using pyridine-d 5 as a solvent are as follows. Table 1 shows spectral data for each carbon of the non-sugar part of the compound of the formula (1).

(피리딘-d5, δ): 9.50, 16.24, 17.42, 21.03, 24.05, 25.73, 26.53, 26.74, 26.81, 27.04, 27.37, 30.65, 30.95, 31.63, 32.50, 35.28, 36.12, 36.90, 40.08, 45.29, 45.46, 52.84, 64.92, 75.28, 90.02, 90.36, 110.25(Pyridine-d 5 , δ): 9.50, 16.24, 17.42, 21.03, 24.05, 25.73, 26.53, 26.74, 26.81, 27.04, 27.37, 30.65, 30.95, 31.63, 32.50, 35.28, 36.12, 36.90, 40.08, 45.29, 45.46 , 52.84, 64.92, 75.28, 90.02, 90.36, 110.25

피리딘-d5을 용매로 하여 측정한 당부의 탄소 핵자기 공명 스펙트럼 결과는 다음과 같고, 표 2에 화학식 1의 화합물의 당부의 각 탄소에 대한 스펙트럼 데이터를 제시하였다.Carbon nuclear magnetic resonance spectra of the sugar moiety measured using pyridine-d 5 as a solvent are as follows. Table 2 shows spectral data for each carbon of the sugar moiety of the compound of Formula 1.

(피리딘-d5, δ): 62.65, 62.85, 71.57, 71.76, 77.03, 77.91, 78.12, 78.20, 78.52, 83.13, 101.89, 105.94(Pyridine-d 5 , δ): 62.65, 62.85, 71.57, 71.76, 77.03, 77.91, 78.12, 78.20, 78.52, 83.13, 101.89, 105.94

첨부된 도면 도 8에 화학식 1의 화합물의 탄소 핵자기공명스펙트럼을 제시하였다. 표 1의 화학식 1의 화합물의 비당부의 수소 및 탄소핵자기공명스펙트럼 데이터와 표 2의 화학식 1의 화합물의 당부의 수소 및 탄소핵자기공명스펙트럼 데이터에 각각 비당부와 당부의 1차, 2차, 3차 등 탄소의 종류를 제시하였으며 도 9에 무변조증강극성전달스펙트럼을 제시하였다.In the accompanying drawings, the carbon nuclear magnetic resonance spectrum of the compound of Formula 1 is shown. Hydrogen and carbon nuclear magnetic resonance spectrum data of the non-sugar part of the compound of Formula 1 of Table 1 and hydrogen and carbon nuclear magnetic resonance spectrum data of the sugar part of the compound of Formula 1 of Table 2, respectively, The types of carbon,, tertiary, etc. are presented, and in FIG. 9, the modulation-free amplification polarization spectrum is shown.

도 10, 11에 화학식 1의 화합물의 수소-수소 상관성분광스펙트럼(1H-1H COSY)을 제시하였다. 도 12, 13에는 화학식 1의 화합물의 헤테로핵다중양자상관성스펙트럼을 제시하였으며 도 14, 15에는 헤테로핵다중결합연결스펙트럼(HMQC, HMBC)를 제시하였다.10 and 11 show the hydrogen-hydrogen correlated light spectrum of the compound of Formula 1 ( 1 H- 1 H COSY). 12 and 13 show heteronuclear multi-proton correlation spectra of the compound of Formula 1, and FIGS. 14 and 15 show heteronuclear multi-bond linkage spectra (HMQC and HMBC).

상기한 목적을 달성하기 위해 본 발명을 첨부 도면에 의거하여 좀더 상세히 설명하면 더욱 명백해질 것이다.BRIEF DESCRIPTION OF THE DRAWINGS The present invention will be more apparent from the following detailed description based on the accompanying drawings in order to achieve the above object.

하기에서 본 발명을 설명함에 있어, 관련된 공지 기능 또는 구성에 대한 구체적인 설명이 본 발명의 요지를 불필요하게 흐릴 수 있다고 판단되는 경우에는 그 상세한 설명은 생략할 것이다. 그리고 후술되는 용어들은 본 발명에서의 기능을 고려하여 정의된 용어들로서 이는 사용자, 운용자의 의도 또는 관례 등에 따라 달라질 수 있다. 그러므로 그 정의는 본 명세서 전반에 걸친 내용을 토대로 내려져야할 것이다.In the following description of the present invention, if it is determined that a detailed description of a related known function or configuration may unnecessarily obscure the subject matter of the present invention, the detailed description thereof will be omitted. Terms to be described later are terms defined in consideration of functions in the present invention, and may be changed according to intentions or customs of users or operators. Therefore, the definition should be made based on the contents throughout the specification.

이와 같은 본 발명에 의하면 신물질의 발명으로 이 물질의 약리활성의 검정 후 의약품으로의 개발 가능성이 있으며,According to the present invention as described above, there is a possibility of developing a pharmaceutical product after the pharmacological activity of this substance is assayed,

전통적 민간 생약인 방울비짜루(남옥대)는 유효성분이 밝혀지지 않아 지표성분의 설정이 어려우므로 본 발명으로 방울비짜루의 지표 성분 설정 및 생약의 규격화에 적용할 수 있으며,The traditional folk herbal medicine drops bijaru (Namokdae) is an active ingredient is not known because it is difficult to set the indicator component, the present invention can be applied to the specification of the medicinal herbs and standardization of herbal medicines,

방울비짜루의 성분 연구로서 새로운 약용작물을 개발, 육성하기 위한 기초 자료로 활용할 수 있는 매우 유익한 발명임이 명백하다.It is evident that this is a very beneficial invention that can be used as a basic data for developing and nurturing new medicinal crops as a research on the constituents of cherry cherries.

Claims (2)

방울비짜루(남옥대)로부터 추출된 화학식 1로 표현되는 아스파올리고닌.Aspa oligonin represented by the formula (1) extracted from the cherry bambi (Namokdae). <화학식 1><Formula 1> 방울비짜루(남옥대)에 있어서,In cherry blossoms (Namokdae), 건조된 방울비짜루 뿌리줄기 3킬로그램을 분쇄하는 제 1단계;A first step of crushing 3 kilograms of dried dried birch root stems; 상기의 분쇄된 뿌리줄기를 실온에서 메탄올(MeOH)을 사용하여 5회 추출하는 제 2단계;A second step of extracting the pulverized root stem five times using methanol (MeOH) at room temperature; 상기 추출로 인해 발생되는 여과액을 모아 진공농축하여 1062그램의 추출물을 얻는 제 3단계;Collecting a filtrate generated by the extraction and concentrating in vacuo to obtain a 1062 gram extract; 상기의 추출물을 증류수에 현탁하여 에테르(Et2O)로 3회 탈지하는 제 4단계;Suspending the extract in distilled water to degrease with ether (Et 2 O) three times; 상기에서 탈지된 물질의 수층을 다시 수포화 부탄올(n-BuOH)를 사용하여 5회 추출한 다음 부탄올 분획 125그램을 얻는 제 5단계;A fifth step of extracting the aqueous layer of the degreased material five times again using saturated butanol (n-BuOH) and then obtaining 125 grams of butanol fraction; 상기의 부탄올 분획 30그램을 실리카겔 칼럼 크로마토그라피(용출제, CHCl3/MeOH/H2O(20:3:1 → 6:4:1), 기울기 용출)하여 20개의 분획으로 나누는 제 6단계;A sixth step of dividing 30 g of the butanol fraction into 20 fractions by silica gel column chromatography (eluent, CHCl 3 / MeOH / H 2 O (20: 3: 1 → 6: 4: 1), gradient eluting); 상기의 20개의 분획중 5번째 분획을 세팍 C18(Sep-Pak C18)를 사용하여(용출제, H2O→20%MeOH→100%MeOH, 기울기 용출) 정제한 후 최종 아스파올리고닌 94밀리그램을 순수하게 단리하는 제 7단계를 포함하여 이루어지는 것을 특징으로 하는 아스파올리고닌 추출 방법.The fifth fraction of the 20 fractions was purified using Sepak C 18 (Sep-Pak C 18 ) (eluent, H 2 O → 20% MeOH → 100% MeOH, gradient elution), followed by final aspaolinin 94 Aspa oligonin extraction method comprising a seventh step of isolating milligram pure.
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JPH02129198A (en) * 1988-11-07 1990-05-17 Dowa Mining Co Ltd Method for recovering saponin from asparagus waste
JPH02247196A (en) * 1989-03-22 1990-10-02 Dowa Mining Co Ltd Recovery of purified saponin from asparagus
JPH0348694A (en) * 1989-07-18 1991-03-01 Dowa Mining Co Ltd Novel saponin substance
JPH06239755A (en) * 1993-02-16 1994-08-30 Dowa Mining Co Ltd Antifungal agent

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02129198A (en) * 1988-11-07 1990-05-17 Dowa Mining Co Ltd Method for recovering saponin from asparagus waste
JPH02247196A (en) * 1989-03-22 1990-10-02 Dowa Mining Co Ltd Recovery of purified saponin from asparagus
JPH0348694A (en) * 1989-07-18 1991-03-01 Dowa Mining Co Ltd Novel saponin substance
JPH06239755A (en) * 1993-02-16 1994-08-30 Dowa Mining Co Ltd Antifungal agent

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