KR101514878B1 - Compound from the Rice Straw Extract and Its Algicidal Activity Against Blue-Green Algae - Google Patents

Compound from the Rice Straw Extract and Its Algicidal Activity Against Blue-Green Algae Download PDF

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KR101514878B1
KR101514878B1 KR1020130054366A KR20130054366A KR101514878B1 KR 101514878 B1 KR101514878 B1 KR 101514878B1 KR 1020130054366 A KR1020130054366 A KR 1020130054366A KR 20130054366 A KR20130054366 A KR 20130054366A KR 101514878 B1 KR101514878 B1 KR 101514878B1
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compound
rice straw
methanol
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정일민
김승현
아메드
김은혜
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건국대학교 산학협력단
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/40—Liliopsida [monocotyledons]
    • A01N65/44—Poaceae or Gramineae [Grass family], e.g. bamboo, lemon grass or citronella grass
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption

Abstract

본 발명은 신규한 볏짚 추출물 유래 화합물, 이의 남조류 생장 억제 용도에 관한 것으로,
본 발명의 화합물은 남조류 생장 억제 효과가 우수하여, 벼의 생육을 저해하는 남조류의 생장 저해 용도로 유용하게 사용될 수 있다. The present invention relates to a novel straw straw extract-derived compound, its use for inhibiting cyanobacterial growth,
The compound of the present invention has an excellent effect of inhibiting the growth of cyanobacteria and can be usefully used for inhibiting the growth of cyanobacteria which inhibits the growth of rice.

Description

볏짚 추출물 유래 화합물 및 이의 남조류 생장 억제 용도{Compound from the Rice Straw Extract and Its Algicidal Activity Against Blue-Green Algae}[Technical Field] The present invention relates to a compound derived from a rice straw extract and a method for inhibiting the growth of green algae,

본 발명은 볏짚 추출물 유래 신규 화합물 및 이의 남조류 생장 억제 용도에 관한 것이다. The present invention relates to novel compounds derived from rice straw extracts and their use for inhibiting cyanobacterial growth.

벼(Oryza sativa L.)는 벼과(Gramineae)에 속하는 1년생 초본식물로 아시아 전역에 널리 분포하고 있다. 높이는 50～100 cm이며 뿌리에 가까운 곳에서 가지를 쳐서 포기를 형성하여 자란다. 꽃이 필 때는 곧추 서지만 익을 때는 밑으로 처지며 많은 소수가 달리고 소수는 가지에 호생하며 짧은 대가 있고 1개의 꽃으로 된다. 꽃은 7~8월경에 피며 자가수분에 의하여 결실한다.Rice ( Oryza Sativa L. ) is a perennial herbaceous plant belonging to the genus Gramineae and widely distributed throughout Asia. Height is 50 ~ 100 cm. It grows by forming branches in the branches near the roots. When flowers bloom, they stand upright, but when they are ripe, they fall downward. Many minorities run. Flowers bloom around July to August, and they are eliminated by their own moisture.

벼에 대한 연구는 농업 재배적 측면에서 육종개발에 의한 생산성 향상과 병충해 질병에 대한 저항성 증대와 관련된 연구가 주로 이루어져 왔다. 쌀로부터 수종의 스테로이드(steroid), 테르페노이드(terpenoid)와 알카노이드(alkaloid)가 분리 보고되어 있으며, 그 중 에르고스테롤 퍼옥사이드(ergosterol peroxide)와 7-옥소-스티그마스테롤(7-oxo-stigmasterol)은 식물독성 효과를 가지고 있는 것으로 보고되어 있다. 쌀의 껍질인 왕겨에서의 추출물은 대표적으로 1-테트라트리아콘탄올(1-tetratriacontanol), β-시토스테롤(β-sitosterol), 모미락톤 A(momilactone A), 모미락톤 B(momilactone B), 트리신(tricin)이 보고된 바 있으며, 모미락톤 A는 제초제 활성이 모미락톤 B는 항암 활성이 보고된 바 있다. 하지만 벼의 지상부인 볏짚에 관한 성분 연구는 거의 이루어지지 않아 플라본(flavones) 인 워고닌(wogonin), 리나닌(linarin) 및 펙토리나린(pectolinarin)을 분리 보고한 연구가 전부이다.Studies on rice have been carried out mainly on the improvement of productivity due to breeding development and the increase of resistance to pest diseases in terms of agricultural cultivation. Several types of steroids, terpenoids and alkaloids have been isolated from rice, including ergosterol peroxide and 7-oxo-stigmasterol, Has been reported to have a phytotoxic effect. Extracts from rice hulls, which are the husks of rice, are typically selected from the group consisting of 1-tetratriacontanol, β-sitosterol, momilactone A, momilactone B, Tricin has been reported, and mymilactone A has been reported to have herbicide activity and mymilactone B has been reported to have anticancer activity. However, almost no studies have been done on the rice straw, which is above the rice, and all of the studies on the separation of the flavones wogonin, linarin and pectolinarin have been reported.

한편, 생태계 내에서 한 식물로부터 어떤 물질이 방출되어 다른 식물체의 생장에 영향을 주는 작용을 타감작용(allelopathy)이라고 한다. 타감작용 현상에 대해서는 제초제와 같은 농약사용을 줄이고자하는 환경친화적인 측면에서 현재 농업분야에서 많이 응용되고 있다. 벼로부터 생성되는 주요 타감작용 물질로서 푸마르산(fumaric acid)과 9, 12-옥타데카노산(9, 12-octadecanoic acid), 메틸 에스테르(methyl ester), 벤조산(benzoic acid), 4-하이드록시-3-메톡시-메틸 에스테르(4-hydroxy-3-methoxy-, methyl ester), 프레그나-5 (pregna-5), 20-디엔-3베타-올(20-dien-3.beta.-ol), p-쿠마르산(p-coumaric acid), p-하이드록시벤조산(p-hydroxybenzoic acid), 시린즈산(syringic acid), 바닐산(vanillic acid), o-하이드록시페닐아세트산(o-hydroxyphenylacetic acid), 페룰산(ferulic acid), 프로피온산(propionic acid), 아세트산(acetic acid), 부티르산(butyric acid) 등이 보고된 바 있으며 특히 남조류 생장 저해물질에 대해, 한국공개특허 10-2004-0078453호 에서 볏짚의 극성용매 추출물을 개시하고 있으나, 구체적인 활성 화합물에 대해서는 아직까지 보고된 바 없다. On the other hand, it is said that allelopathy is an action that affects the growth of another plant by releasing a substance from one plant in an ecosystem. As for the sensation of hitting sensation, it is widely applied in the agricultural field in terms of environment-friendly aspect in which the use of pesticide such as herbicide is reduced. The major sensitizing agents produced from rice are fumaric acid, 9,12-octadecanoic acid, methyl ester, benzoic acid, 4-hydroxy-3 3-methoxy-, methyl ester, pregna-5, 20-dien-3beta.-ol, p-coumaric acid, p-hydroxybenzoic acid, syringic acid, vanillic acid, o-hydroxyphenylacetic acid, Ferric acid, propionic acid, acetic acid, butyric acid and the like have been reported. In particular, Korean Patent Laid-Open Publication No. 10-2004-0078453 discloses a method for inhibiting cyanobacterial growth inhibition, , But specific active compounds have not been reported yet.

따라서 본 발명은 볏짚 추출물에서 유래된 남조류 억제 활성이 우수한 신규 화합물, 이의 제조방법 및 이의 용도를 제공하고자 한다. Accordingly, the present invention provides a novel compound having excellent antioxidative activity derived from rice straw extract, a method for its production, and its use.

상기 과제의 해결을 위해, 본 발명은 하기 화학식 1의 구조를 갖는 화합물을 제공한다. In order to solve the above problems, the present invention provides a compound having a structure represented by the following formula (1).

[화학식 1] [Chemical Formula 1]

Figure 112013042501864-pat00001
Figure 112013042501864-pat00001

상기 화학식 1에서, R1, R2 및 R3는 각각 하이드록시일 수 있다. In Formula 1, R 1 , R 2, and R 3 may each be hydroxy.

또한 본 발명은 볏짚을 메탄올에 침지시켜 볏짚의 메탄올 추출물을 제조하는 단계; 상기 메탄올 추출물과 물을 혼합하고 부탄올로 재추출하여 부탄올 추출물을 제조하는 단계; 및 상기 부탄올 추출물에 클로로폼 및 메탄올을 용리액으로 하는 컬럼 크로마토그래피를 실시하는 단계를 포함하는 볏짚으로부터 상기 화학식 1의 화합물을 추출하는 방법을 제공한다. The present invention also relates to a method for producing a methanol extract of rice straw, comprising: preparing a methanol extract of rice straw by immersing the rice straw in methanol; Mixing the methanol extract with water and re-extracting with butanol to prepare a butanol extract; And subjecting the butanol extract to column chromatography using chloroform and methanol as an eluent, to extract the compound of Formula 1 from rice straw.

또한 본 발명은 상기 화학식 1의 화합물을 유효성분으로 함유하는 남조류의 생장 억제용 조성물을 제공한다. The present invention also provides a composition for inhibiting growth of cyanobacteria comprising the compound of formula (1) as an active ingredient.

또한 본 발명은 상기 화학식 1의 화합물을 남조류 배양액에 첨가하여 배양하는 단계를 포함하는 남조류의 생장 억제 방법을 제공한다. The present invention also provides a method for inhibiting the growth of cyanobacteria comprising the step of adding the compound of formula 1 to a cyanobacterium culture solution and culturing the same.

본 발명에 따른 볏짚 추출물 유래 화합물은 남조류 생장 억제 효과가 우수하여, 벼의 생육을 저해하는 남조류의 생장 저해 용도로 유용하게 사용될 수 있다. The compound derived from rice straw extract according to the present invention is excellent in inhibiting the growth of cyanobacteria, and can be usefully used for inhibiting growth of cyanobacteria which inhibits the growth of rice.

도 1은 본 발명 실시예에 따른 화합물 1의 구조 및 이의 단편화 패턴(우측)이다.
도 2은 본 발명 실시예에 따른 화합물 2의 구조 및 이의 단편화 패턴(우측)이다.
도 3은 본 발명 실시예에 따른 화합물 3의 구조 및 이의 단편화 패턴(우측)이다.
도 4는 본 발명 실시예에 따른 화합물 4의 구조 및 이의 단편화 패턴(우측)이다.
도 5는 본 발명 실시예에 따른 화합물 5의 구조 및 이의 단편화 패턴(하단)이다.
도 6은 본 발명 화합물인 화합물 5의 조류 생장 억제 활성을 보여주는 실험 결과 그래프이다. Fig. 1 shows the structure of compound 1 according to an embodiment of the present invention and its fragmentation pattern (right).
Figure 2 shows the structure of compound 2 according to the present invention and its fragmentation pattern (right).
Figure 3 shows the structure of compound 3 according to the present invention and its fragmentation pattern (right).
4 shows the structure of compound 4 according to the present invention and its fragmentation pattern (right).
Figure 5 shows the structure of compound 5 and its fragmentation pattern (bottom) according to an embodiment of the present invention.
FIG. 6 is a graph showing an experimental result showing the activity of inhibiting the growth of algae of the compound 5 of the present invention.

본 발명은 하기 화학식 1의 구조를 갖는 화합물을 제공한다. The present invention provides a compound having a structure represented by the following formula (1).

[화학식 1] [Chemical Formula 1]

Figure 112013042501864-pat00002
Figure 112013042501864-pat00002

상기 화학식 1에서, R1, R2 및 R3는 각각 하이드록시일 수 있다. In Formula 1, R 1 , R 2, and R 3 may each be hydroxy.

삭제delete

본 발명의 한 구체예에 따르면, 상기 화학식 1의 구조를 갖는 화합물은 볏짚으로부터 추출한 것일 수 있다. 본 발명의 발명자들은 볏짚으로부터 상기 신규 화합물을 추출하여 구조를 규명하였고, 상기 화합물이 우수한 남조류 생장 억제 효과를 가짐을 확인하였다. 그러나 상기 화학식 1의 화합물은 볏짚 이외에 다른 식물로부터 추출할 수도 있으며, 또한 일반적인 화학적 합성 방법에 의해서 합성할 수도 있다. According to one embodiment of the present invention, the compound having the structure of Formula 1 may be extracted from rice straw. The inventors of the present invention have identified the structure by extracting the novel compound from rice straw and confirmed that the compound has excellent cyanobacterial growth inhibitory effect. However, the compound of formula (1) may be extracted from plants other than rice straw, or may be synthesized by a general chemical synthesis method.

또한 본 발명은 볏짚을 메탄올에 침지시켜 볏짚의 메탄올 추출물을 제조하는 단계; 상기 메탄올 추출물과 물을 혼합하고 부탄올로 재추출하여 부탄올 추출물을 제조하는 단계; 및 상기 부탄올 추출물에 클로로폼 및 메탄올을 용리액으로 하는 컬럼 크로마토그래피를 실시하는 단계를 포함하는 볏짚으로부터 상기 화합물을 추출하는 방법을 제공한다. The present invention also relates to a method for producing a methanol extract of rice straw, comprising: preparing a methanol extract of rice straw by immersing the rice straw in methanol; Mixing the methanol extract with water and re-extracting with butanol to prepare a butanol extract; And subjecting the butanol extract to column chromatography using chloroform and methanol as eluants. The present invention also provides a method for extracting the compound from rice straw.

상기 컬럼 크로마토그라피는 이에 한정되는 것은 아니지만 흡착제로서 실리카겔, 역상실리카겔, 세파덱스류, 다이아이온 레진류, 알루미나, 활성탄, 규산마그네슘, 탄산칼슘, 인산칼슘, 인산마그네슘, 마그네시아 또는 수산화칼륨 등을 사용할 수 있으며, 바람직하게는 실리카겔을 사용할 수 있다.The column chromatography may use silica gel, reversed phase silica gel, Sephadex, Diaion resins, alumina, activated carbon, magnesium silicate, calcium carbonate, calcium phosphate, magnesium phosphate, magnesia or potassium hydroxide as the adsorbent And preferably silica gel can be used.

상기 클로로폼 및 메탄올 용리액은 chloroform:methanol 의 비율이 (96-99) : (1-4) 인 혼합용액을 사용할 수 있으며, 이후 메탄올 수용액을 용리액으로 하는 컬럼 크로마토그래피가 실시될 수 있다. The chloroform and methanol eluent may be a mixed solution of chloroform: methanol having a ratio of (96-99): (1-4), followed by column chromatography using an aqueous solution of methanol as an eluent.

그러나 본 발명에 따른 화학식 1의 화합물을 제조하는 방법은 이에 제한되는 것은 아니며, 일반적인 화학적 합성 방법에 의해서 제조할 수 있음은 당업자에게 자명하다.However, the method of preparing the compound of formula (1) according to the present invention is not limited thereto, and it is apparent to those skilled in the art that the compound can be prepared by a general chemical synthesis method.

또한 본 발명은 상기 화학식 1의 화합물을 유효성분으로 함유하는 남조류의 생장 억제용 조성물을 제공한다. The present invention also provides a composition for inhibiting growth of cyanobacteria comprising the compound of formula (1) as an active ingredient.

본 발명의 한 구체예에서, 상기 남조류의 생장 억제용 조성물은 상기 화학식 1의 화합물 외에 본 발명이 목적으로 하는 주 효과를 손상시키지 않는 범위 내에서, 바람직하게는 주 효과에 상승 효과를 줄 수 있는 다른 성분 등을 함유할 수 있다. In one embodiment of the present invention, the composition for inhibiting the growth of the cyanobacterium may contain, in addition to the compound of the formula (1), a compound capable of giving a synergistic effect to the main effect Other components, and the like.

본 발명의 다른 구체예에서, 상기 남조류는 마이크로시스티스 애루기노사(Microcystis aeruginosa)일 수 있으나 이에 제한되는 것은 아니다. In another embodiment of the present invention, the cyanobacterium may be, but is not limited to, Microcystis aeruginosa .

이하의 실시예에서 확인할 수 있는 바와 같이, 본 발명의 화학식 1의 화합물은 남조류의 생장을 처리 농도에 비례하여 매우 높은 효율로 저해하는 효과가 있다. 상기 남조류는 연못이나 수계 등에서 여름철 과생장하며, 벼가 생육되는 물의 온도를 저하시키고, 광합성을 저해하여 벼의 생육을 저해하는 바, 남조류 가 성장하고 있는 배양액에 본 발명의 화학식 1의 화합물을 첨가하여 배양하는 방법을 통해 남조류의 생장을 억제할 수 있다. As can be seen from the following examples, the compound of Chemical Formula (1) of the present invention has an effect of inhibiting the growth of cyanobacteria at a very high efficiency in proportion to the treatment concentration. The cyanobacterium grows in a pond or aquatic environment in summer and lowers the temperature of the water in which the rice grows and inhibits photosynthesis and inhibits the growth of the rice. In addition, the compound of formula And then cultivating the plant to inhibit the growth of blue algae.

본 발명의 한 구체예에서, 상기 배양액에 첨가되는 화합물 농도는 5 내지 1000 mg/L일 수 있으나 이에 제한되는 것은 아니다.
In one embodiment of the present invention, the concentration of the compound added to the culture solution may be 5 to 1000 mg / L, but is not limited thereto.

이하, 본 발명의 이해를 돕기 위하여 실시예를 들어 상세하게 설명하기로 한다. 다만 하기의 실시예는 본 발명의 내용을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다. 본 발명의 실시예는 당업계에서 평균적인 지식을 가진 자에게 본 발명을 보다 완전하게 설명하기 위해 제공되는 것이다.
BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are intended to illustrate the contents of the present invention, but the scope of the present invention is not limited to the following examples. Embodiments of the present invention are provided to more fully describe the present invention to those skilled in the art.

<< 실험예Experimental Example >>

하기의 실험예들은 본 발명에 따른 각각의 실시예에 공통적으로 적용되는 실험예를 제공하기 위한 것이다.The following experimental examples are intended to provide experimental examples that are commonly applied to the respective embodiments according to the present invention.

1. 시약1. Reagents

모든 시약은 분석 등급용을 사용하였다. n-헥산, 에틸 아세테이트, 메탄올, 에탄올, 황산 및 바닐린은 Daejung Chemicals and Metals (Seoul, South Korea)에서 구입하였다. 미리 코팅된 TLC 플레이트(층 두께 0.5mm), 컬럼 크로마토그래피용 실리카 겔(70-230 mesh ASTM) 및 LiChroprep RP-18 (40-63 μm)은 Merck (Darmstadt, Germany)에서 구입하였다. β-시토스테롤, 스테아르산, 팔미트산, 올레산 및 D-자일로스의 표준품은 Sigma-Aldrich (St. Louis, MO, USA)에서 구입하였다. All reagents were of analytical grade. n-hexane, ethyl acetate, methanol, ethanol, sulfuric acid and vanillin were purchased from Daejung Chemicals and Metals (Seoul, South Korea). Precoated TLC plates (layer thickness 0.5 mm), silica gel for column chromatography (70-230 mesh ASTM) and LiChroprep RP-18 (40-63 μm) were purchased from Merck (Darmstadt, Germany). Standard products of β -sitosterol, stearic acid, palmitic acid, oleic acid and D-xylose were purchased from Sigma-Aldrich (St. Louis, Mo., USA).

2. 기기2. Device

녹는점은 Electrochemical Engineering (Electrothermal, Seoul, South Korea) model IA9100 melting point apparatus를 사용하여 측정되었다. 선광성(Optical rotation)은 Instruments Ltd (Seoul, South Korea) model AA-10 polarimeter를 사용하여 측정되었다. 1H- 및 13C -NMR 스펙트럼은 서울대학교 농업생명과학대학의 National Instrumentation Centre for Environmental Management (NICEM)에서 Bruker Avance-600 spectrometer 를 사용하여 각각 600 및 150 MHz에서 측정되었다. NMR 스펙트럼은 중수소화된 클로로폼, d5-피리딘 및 d4-메탄올 상에서 테트라메틸실란(TMS)을 내부 표준물질로 하여 측정되었고, 화학적 이동은 ppm (δ)으로, 결합 상수(J) 는 Hz로 나타내었다. 고해상도 ESI/FT 질량분석은 Dionex U 3000 HPLC system (NICEM, Seoul National University)와 함께 Thermo-Finnigan LTQ-Orbitrap instrument (Thermo Scientific, USA)상에 기록되었고, IR 스펙트럼은 한국 과학기술원의 Thermo Scientific FT-IR model Nicolet 6700 (USA) spectrophotometer 상에 기록되었다.
Melting points were measured using Electrochemical Engineering (Electrothermal, Seoul, South Korea) model IA9100 melting point apparatus. Optical rotation was measured using a Model AA-10 polarimeter from Instruments Ltd (Seoul, South Korea). 1 H- and 13 C-NMR spectra were measured at 600 and 150 MHz, respectively, using a Bruker Avance-600 spectrometer at National Instrumentation Center for Environmental Management (NICEM), Seoul National University. NMR spectra were measured with tetramethylsilane (TMS) as an internal standard on deuterated chloroform, d 5 -pyridine and d 4 -methanol, chemical shifts in ppm (δ) and coupling constants ( J ) in Hz Respectively. High resolution ESI / FT mass spectrometry was recorded on a Thermo-Finnigan LTQ-Orbitrap instrument (Thermo Scientific, USA) with a Dionex U 3000 HPLC system (NICEM, Seoul National University) and IR spectra were recorded on a Thermo Scientific FT- IR model was recorded on a Nicolet 6700 (USA) spectrophotometer.

<< 실시예Example 1> 볏짚 표본 수득 및 추출을 통한 화합물 분리  1> Rice straw sampling and separation of compounds by extraction

O. sativa 의 볏짚은 건국대학교 실험 농장에서 수득되었다. 수집 후, 샘풀은 25-30℃에서 3주간 건조되었으며, 대조 표본(레퍼런스 코드 ILPUM variety)는 건조 후 건국대학교 응용생명과학부의 식물 표본실에 보관되었다. He . Sativa 's rice straw It was obtained from Konkuk University experimental farm. After collection, the sample was dried at 25-30 ℃ for 3 weeks. The control specimen (reference code ILPUM variety) was dried and stored in the plant sampling room of Konkuk University.

건조된 O. sativa 볏짚(10 kg)은 메탄올(55L)에 1주 동안 상온에서 침지되었고, 상청액을 진공에서 농축시켜 78g의 추출물을 얻었다. 이는 물에 재분산되었고, 이후 1) 헥산, 2) 에틸 아세테이트, 3) n-부탄올로 각각 추출되어 9.4g의 헥산 추출물, 11.2g의 에틸 아세테이트 추출물, 14.2g의 n-부탄올 추출물을 얻었다. The dried O. Sativa rice straw (10 kg) was immersed in methanol (55 L) for 1 week at room temperature and the supernatant was concentrated in vacuo to obtain 78 g of extract. This was redispersed in water and then extracted with 1) hexane, 2) ethyl acetate and 3) n-butanol, respectively, to obtain 9.4 g of hexane extract, 11.2 g of ethyl acetate extract and 14.2 g of n-butanol extract.

1) One) 헥산Hexane 추출물에서의 화합물 분리  Separation of compounds from extracts

헥산 추출물은 헥산과 에틸 아세테이트 용매상에서 실리카 겔 크로마토그래피로 분리되었고, 그 결과 옥타코스-9-엔일 프로피오네이트(11mg), 1-테트라트리아콘타놀(16mg) 및 트리트리아콘탄-4,12-디엔(7mg)의 세 화합물을 얻었다. The hexane extract was separated by silica gel chromatography on a solvent of hexane and ethyl acetate, and as a result octacos-9-enyl propionate (11 mg), 1-tetra triacontanol (16 mg) -Diene &lt; / RTI &gt; (7 mg).

2) 에틸 아세테이트 추출물에서의 화합물 분리2) Separation of compounds from ethyl acetate extract

EtOAc 추출물(11.2g)은 실리카 겔-정상 상 컬럼 크로마토그래피로 분리되었고, 이하의 용리액에 따른 30분획을 얻었다: hexane 분획 1; hexane:EtOAc (9:1) 분획 2-5; hexane:EtOAc (8:2) 분획 6-11; hexane:EtOAc (7:3) 분획 12-15; hexane:EtOAc (1:1) 분획 16-20; EtOAc 분획 21-22; EtOAc:MeOH (9.5:0.5) 분획 23-26; EtOAc:MeOH (9:1) 분획 27-30. The EtOAc extract (11.2 g) was separated by silica gel-top phase column chromatography and yielded 30 fractions according to the following eluent: hexane fraction 1; hexane: EtOAc (9: 1) fraction 2-5; hexane: EtOAc (8: 2) fractions 6-11; hexane: EtOAc (7: 3) fractions 12-15; hexane: EtOAc (1: 1) fractions 16-20; EtOAc fractions 21-22; EtOAc: MeOH (9.5: 0.5) fractions 23-26; EtOAc: MeOH (9: 1) fractions 27-30.

이중 분획 6을 결정화하고, 컬럼 크로마토그래피로 정제하여 β-sitosterol (23 mg)을 얻었다. 이는 Sigma 사에서 구입한 표준 샘플과 비교되었다. 분획 11을 메틸렌 디클로라이드 및 메탄올과 함께 컬럼 크로마토그래피로 추가 정제하였고, 두 순수 화합물(n-tetracontan-15α-ol (6 mg), n-tritetracontan-5α-ol (9 mg))을 수득하였다. 분획 23-26을 실리카 겔 및 Lichroprep RP-18 (octadecyl silica [ODS]) 컬럼 크로마토그래피 후 단일 흰색 화합물을 가루 형태로 수득하였다. 이는 갈산(gallic acid, 13 mg)로 확인되었다. 분획 27을 클로로폼 및 메탄올을 이용한 컬럼 크로마토그래피 결과 하나의 순수 단일 화합물(β-sitosterol-3-O-β-D-glucoside (12 mg))을 수득하였다. The double fraction 6 was crystallized and purified by column chromatography to obtain β- sitosterol (23 mg). This was compared with standard samples purchased from Sigma. Fraction 11 was further purified by column chromatography with methylene dichloride and methanol to give two pure compounds ( n -tetracontan-15 [alpha] -ol (6 mg), n -tritetracontan-5 [ Respectively. Fraction 23-26 was chromatographed on silica gel and Lichroprep RP-18 (octadecyl silica [ODS]) column to give a single white compound in powder form. It was identified as gallic acid (13 mg). Fraction 27 was subjected to column chromatography using chloroform and methanol to obtain one pure single compound ( ? -Sitosterol-3- O-? -D-glucoside (12 mg)).

3) n-3) n- 부탄올Butanol 추출물에서의 화합물 분리 Separation of compounds from extracts

총 n-부탄올 추출물(14.2g)은 실리카 겔(800 g) 정상-상 CC 로 분리되었고, 이하의 용리액에 따른 32 분획(250 mL)을 얻었다: chloroform 분획 1; chloroform:methanol (99:1) 분획 2-5; chloroform:methanol (98:2) 분획 6-11; chloroform:methanol (97:3) 분획 12-15; chloroform:methanol (96:4) 분획 16-20; chloroform:methanol (9.5:0.5) 분획 21-24; chloroform:methanol (9:1) 분획 25-28; chloroform:methanol (8.8:1.2) 분획 29-30; chloroform:methanol (8.5:1.5) 분획 31-32. 모든 분획은 TLC로 분석되었다. 분획 21-24를 혼합하고, 이를 대상으로 dichloromethane:methanol 혼합물(9.9:01; 9.8:0.2; 9.7:0.3; 9.6:0.4; 9.5:0.5; 9.4:0.6; 9.3:0.7; 9.2:0.8; 9.1:0.9; 9:1)과 재 크로마토그래피를 수행하였고, 10개의 분획을 얻었다. 그 중 분획 6-8을 혼합하고 80, 60, 40 20, 10 및 0 %의 물을 포함하는 메탄올을 용리액으로 하여 순차적으로 Lichroprep RP-18 ODS 실리카 겔(4.2 g; 각 분획마다 50 mL) 과 재 크로마토그래피를 수행하여 화합물 1(34 mg), 화합물 2(18 mg) 및 화합물 3(22 mg)의 세 화합물을 분리하였다. 분획 9-10을 혼합하고, 80, 60, 40 20, 10 및 0 %의 물을 포함하는 메탄올을 용리액으로 하여 순차적으로 Lichroprep RP-18 ODS 실리카 겔(3.8 g; 각 분획마다 50 mL) 과 재 크로마토그래피를 수행하여 화합물 4(29 mg) 및 화합물 5(27 mg)의 두 화합물을 분리하였다. Total n-butanol extract (14.2 g) was isolated on silica gel (800 g) in normal-phase CC and yielded 32 fractions (250 mL) according to the following eluent: chloroform fraction 1; chloroform: methanol (99: 1) fraction 2-5; chloroform: methanol (98: 2) fraction 6-11; chloroform: methanol (97: 3) fraction 12-15; chloroform: methanol (96: 4) fractions 16-20; chloroform: methanol (9.5: 0.5) fractions 21-24; chloroform: methanol (9: 1) fractions 25-28; chloroform: methanol (8.8: 1.2) fractions 29-30; chloroform: methanol (8.5: 1.5) fractions 31-32. All fractions were analyzed by TLC. 9.2: 0.8, 9.1: 0.8, 9.1: 0.5, 9.4: 0.6, 9.3: 0.7, 9.2: 0.8, 9.1: 0.9; 9: 1), and 10 fractions were obtained. Among them, fractions 6-8 were mixed and Lichroprep RP-18 ODS silica gel (4.2 g; 50 mL for each fraction) was added sequentially with methanol containing 80, 60, 40, 20, 10 and 0% The re-chromatography was performed to separate three compounds: Compound 1 (34 mg), Compound 2 (18 mg) and Compound 3 (22 mg). Fractions 9-10 were mixed and sequentially purified using Lichroprep RP-18 ODS silica gel (3.8 g; 50 mL for each fraction) and methanol as eluant with 80, 60, 40, 20, 10 and 0% Chromatography was performed to separate two compounds, Compound 4 (29 mg) and Compound 5 (27 mg).

상기 화합물 1 내지 3의 1H NMR 데이터는 표 1에, 13C NMR 데이터는 표 2에 나타내었고, 화합물 4의 1H 및 13C NMR 데이터는 이하 표 3에 나타내었다. 각각의 분석 데이터는 아래와 같다. 1 H NMR data of the compounds 1 to 3 are shown in Table 1, 13 C NMR data are shown in Table 2, and 1 H and 13 C NMR data of the compound 4 are shown in Table 3 below. Each analysis data is as follows.

화합물 1:Compound 1: 5,4'-5,4'- dihydroxydihydroxy -7,3'--7,3'- dimethoxyflavonedimethoxyflavone -4'-O-β-D-xylopyranosyl-(2a→1b)-2a-O-β-D--4'-O- beta -D-xylopyranosyl- (2a-1b) -2a-O- [beta] -D- xylopyranosylxylopyranosyl -(2b→1c)-2b-O-β-D-xylopyranosyl-2c-octadecanoate (1)- (2b → 1c) -2b-O-β-D-xylopyranosyl-2c-octadecanoate (1)

노란색 고체; Rf 0.45 (CHCl3:MeOH; 9:1); mp 214 -2160; [α]D 22 - 53.2 (c 0.1, MeOH); UV (MeOH) λmax: 265, 308, 342 nm; IR (KBr) νmax: 3455, 3363, 3261, 2926, 2841, 1721, 1690, 1604, 1513, 1431, 1346, 1265, 1176, 1070, 1027, 839 cm-1; ESI/MS m/z (relative intensity): 977 [M+H]+ (C50H73O19) (5.1), 663 (11.3), 577 (4.5), 531 (6.8), 399 (11.5), 313 (9.1), 267 (24.8), 166 (43.2); HR-ESI/FTMS m/z 977.4759 (calc. for C50H73O19 977.4746).Yellow solid ; R f 0.45 (CHCl 3 : MeOH; 9: 1); mp 214-216 0 ; [?] D 22 - 53.2 ( c 0.1, MeOH); UV (MeOH) [lambda] max : 265, 308, 342 nm; IR (KBr)? Max : 3455, 3363, 3261, 2926, 2841, 1721, 1690, 1604, 1513, 1431, 1346, 1265, 1176, 1070, 1027, 839 cm -1 ; ESI / MS m / z : 977 [M + H] + (C 50 H 73 O 19 ) (5.1), 663 (11.3), 577 (4.5), 531 (6.8), 399 313 (9.1), 267 (24.8), 166 (43.2); HR-ESI / FTMS m / z 977.4759 (calc. For C 50 H 73 O 19 977.4746).

또한, 화합물 1의 산 가수분해 결과, 화합물 1은 D-자일로오스, 플라본 및 스테아르산으로 가수분해되었고, 상기 결과를 종합하여, 화합물 1은 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-β-D-xylopyranosyl-(2a→1b)-2a-O-β-D-xylopyranosyl-(2b→1c)-2b-O-β-D-xylopyranosyl-2c-octadecanoate 이며, 구조가 도 1과 같음을 알 수 있었다. 도 1은 화합물 1의 구조 및 이의 단편화 패턴(우측)이다.
As a result of acid hydrolysis of Compound 1, Compound 1 was hydrolyzed to D-xylose, flavone and stearic acid. Based on the above results, Compound 1 was found to be 5,4'-dihydroxy-7,3'-dimethoxyflavone (2a → 1b) -2a-O- 硫 -D-xylopyranosyl- (2b → 1c) -2b-O- 硫 -D-xylopyranosyl-2c-octadecanoate, 1 &lt; / RTI &gt; Figure 1 shows the structure of compound 1 and its fragmentation pattern (right).

화합물 2:Compound 2: 5,4'-5,4'- dihydroxydihydroxy -7,3'--7,3'- dimethoxyflavonedimethoxyflavone -4'-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D--4'-O-a-D-xylopyranosyl- (2a-1b) -2a-O- xylopyranosylxylopyranosyl -(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-- (2b → 1c) -2b-O-α-D-xylopyranosyl- (2c → 1d) -2c-O- xylopyranosylxylopyranosyl -2d--2d- octadecanoateoctadecanoate (2) (2)

노란색 고체; Rf 0.42 (CHCl3:MeOH; 9:1); mp 224-2250; [α]D 22 - 47.8 (c 0.1, MeOH); UV (MeOH) λmax: 261, 304, 338 nm; IR (KBr) νmax: 3447, 3379, 3283, 2993, 2903, 2837, 1722, 1678, 1606, 1513, 1452, 1344, 1260, 1069, 838 cm-1; ESI/MS m/z (relative intensity): 1109 [M+H]+ (C55H81O23) (1.3), 399 (7.8), 313 (6.1), 267 (7.3), 116 (9.5); HR-ESI/FTMS m/z 1109.5175 (calc. for C55H81O23 ; 1109.5169).Yellow solid; R f 0.42 (CHCl 3: MeOH ; 9: 1); mp 224-225 0 ; [?] D 22 - 47.8 ( c 0.1, MeOH); UV (MeOH) [lambda] max : 261, 304, 338 nm; IR (KBr)? Max : 3447, 3379, 3283, 2993, 2903, 2837, 1722, 1678, 1606, 1513, 1452, 1344, 1260, 1069, 838 cm -1 ; ESI / MS m / z : 1109 [M + H] + (C 55 H 81 O 23 ) (1.3), 399 (7.8), 313 (6.1), 267 (7.3), 116 (9.5); HR-ESI / FTMS m / z 1109.5175 (calc. For C 55 H 81 O 23 ; 1109.5169).

또한, 화합물 2의 산 가수분해 결과, 화합물 1은 D-자일로오스, 플라본 및 스테아르산으로 가수분해되었고, 상기 결과를 종합하여, 화합물 2는 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-2d-octadecanoate 이며, 구조가 도 2와 같음을 알 수 있었다. 도 2는 화합물 2의 구조 및 이의 단편화 패턴(우측)이다.
Further, as a result of acid hydrolysis of Compound 2, Compound 1 was hydrolyzed to D-xylose, flavone and stearic acid. Based on the above results, Compound 2 was found to be 5,4'-dihydroxy-7,3'-dimethoxyflavone (2a-1b) -2a-O-alpha-D-xylopyranosyl- (2b → 1c) -2b-O- 留 -D-xylopyranosyl- 2c-O-? -D-xylopyranosyl-2d-octadecanoate, and the structure was as shown in FIG. Figure 2 shows the structure of compound 2 and its fragmentation pattern (right).

화합물 3: Compound 3: KaempferolKaempferol -3-O-α-D--3-O- [alpha] -D- xylopyranosylxylopyranosyl -(2a→1b)-2a-O-α-D-- (2a-1b) -2a-O- [alpha] -D- xylopyranosylxylopyranosyl -(2b→1c)-2b-O-α-D-- (2b? 1c) -2b-O-? -D- xylopyranosylxylopyranosyl -(2c→1d)-2c-O-α-D-- (2c → 1d) -2c-O-α-D- xylopyranosylxylopyranosyl -2d--2d- hexadecanoatehexadecanoate (3) (3)

노란색 검(gum); Rf 0.37 (CHCl3:MeOH; 9:1); [α]D 22 - 42.1 (c 0.1, MeOH); UV (MeOH) λmax: 267, 311, 348, nm (log 4.2, 2.8, 2.1), IR (KBr) νmax: 3437, 3329, 3265, 2914, 2849, 1722, 1708, 1647, 1601, 1514, 1451, 1376, 1217, 1037, 841 cm-1; ESI/MS m/z : 1053 [M+H]+ (C51H73O23) (1.3), 371 (26.5), 285 (17.1), 269 (13.4), 239 (33.6), 166 (5.8); HR-ESI/FTMS m/z 1053.4551 (calc. for C51H73O23 ; 1053.4542).Yellow gum; R f 0.37 (CHCl 3 : MeOH; 9: 1); [?] D 22 - 42.1 ( c 0.1, MeOH); UV (MeOH) λ max: 267 , 311, 348, nm (log 4.2, 2.8, 2.1), IR (KBr) ν max: 3437, 3329, 3265, 2914, 2849, 1722, 1708, 1647, 1601, 1514, 1451, 1376, 1217, 1037, 841 cm &lt; -1 & gt ;; ESI / MS m / z : 1053 [M + H] + (C 51 H 73 O 23 ) (1.3), 371 (26.5), 285 (17.1), 269 (13.4), 239 (33.6), 166 ; HR-ESI / FTMS m / z 1053.4551 (calc. For C 51 H 73 O 23 ; 1053.4542).

또한, 화합물 3의 산 가수분해 결과, 화합물 3은 D-자일로오스, 캄페롤(kaempferol), 팔미트산으로 가수분해되었고, 상기 결과를 종합하여, 화합물 3은 Kaempferol-3-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-2d-hexadecanoate이며, 구조가 도 3과 같음을 알 수 있었다. 도 3은 화합물 3의 구조 및 이의 단편화 패턴(우측)이다.
Compound 3 was hydrolyzed to D-xylose, kaempferol and palmitic acid as a result of acid hydrolysis of Compound 3, and Compound 3 was found to be Kaempferol-3-O-α- D-xylopyranosyl- (2a → 1b) -2a-O-α-D-xylopyranosyl- (2b → 1c) -2b-O- xylopyranosyl-2d-hexadecanoate, and the structure was as shown in Fig. Figure 3 shows the structure of compound 3 and its fragmentation pattern (right).

화합물 4: Compound 4: MethylMethyl salicylatesalicylate -2-O-α-D--2-O- [alpha] -D- xylopyranosylxylopyranosyl -(2a→1b)-2a-O-α-D-- (2a-1b) -2a-O- [alpha] -D- xylopyranosylxylopyranosyl -(2b→1c)-2b-O-α-D-- (2b? 1c) -2b-O-? -D- xylopyranosylxylopyranosyl -(2c→1d)-2c-O-α-D-- (2c → 1d) -2c-O-α-D- xylopyranosylxylopyranosyl -(2d→1e)-2d-O-α-D-- (2d → 1e) -2d-O-α-D- xylopyranosylxylopyranosyl -(2e→1f)-2e-O-α-D-- (2e &gt; 1f) -2e-O- [alpha] -D- xylopyranosylxylopyranosyl -(2f→1g)-2f-O-α-D-- (2f? 1g) -2f-O-? -D- xylopyranosylxylopyranosyl -(2g→1h)-2g-O-α-D-- (2g → 1h) -2g-O-α-D- xylopyranosylxylopyranosyl -2h--2H- geranilangeranilan -8',10'--8 ', 10'- dioicdioic acidacid -1'--One'- oateoate (4)  (4)

밝은 갈색 고체; Rf 0.27 (CHCl3:MeOH; 9:1); [α]D 22 - 89.1 (c 0.1, MeOH); IR (KBr) νmax: 3516, 3425, 3379, 3281,1732, 1721, 1698, 1635, 1512, 1433, 1345, 1210, 1025 cm-1); ESI/MS m/z : 1423 [M+H]+ (C58H86O40) (2.3),743 (2.8), 611 (5.6), 283 (3.7), 232 (100), 215 (16.1), 151 (14.8); HR-ESI/FTMS m/z 1423.4779 (calc. for C58H86O40 ; 1423.4772).Light brown solid; R f 0.27 (CHCl 3: MeOH ; 9: 1); [?] D 22 - 89.1 ( c 0.1, MeOH); IR (KBr)? Max : 3516, 3425, 3379, 3281, 1732, 1721, 1698, 1635, 1512, 1433, 1345, 1210, 1025 cm -1 ); ESI / MS m / z : 1423 [M + H] + (C 58 H 86 O 40 ) (2.3), 743 (2.8), 611 (5.6), 283 (3.7), 232 (100) , 151 (14.8); HR-ESI / FTMS m / z 1423.4779 (calc. For C 58 H 86 O 40 ; 1423.4772).

또한, 화합물 4의 산 가수분해 결과, 화합물 4는 당으로 D-자일로오스(Rf 0.27 (n-butanol-water-acetic acid; 4:1:5); [α]20 D +18.80 (c 2., water))를 포함함을 알 수 있었고, 상기 결과를 종합하여, 화합물 4는 Methyl salicylate-2-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-(2d→1e)-2d-O-α-D-xylopyranosyl-(2e→1f)-2e-O-α-D-xylopyranosyl-(2f→1g)-2f-O-α-D-xylopyranosyl-(2g→1h)-2g-O-α-D-xylopyranosyl-2h-geranilan-8',10'-dioic acid-1'-oate이며, 구조가 도 4와 같음을 알 수 있었다. 도 4는 화합물 4의 구조 및 이의 단편화 패턴(우측)이다.
Further, as a result of acid hydrolysis of Compound 4, Compound 4 was found to be a D-xylose (R f 0.27 ( n- butanol-water-acetic acid; 4: 1: 5); [alpha] 20 D +18.8 0 ( c 2. water)). As a result, compound 4 was found to contain methyl salicylate-2-O- alpha -D-xylopyranosyl- ) -2a-O- alpha -D-xylopyranosyl- (2b → 1c) -2b-O-α-D-xylopyranosyl- (2c → 1d) -2c- (2f → 1f) -2e-O-α-D-xylopyranosyl- (2f → 1g) -2f-O- 留 -D-xylopyranosyl- O-α-D-xylopyranosyl-2h-geranilan-8 ', 10'-dioic acid-1'-oate. The structure was as shown in FIG. Figure 4 shows the structure of compound 4 and its fragmentation pattern (right).

화합물 5: Compound 5: OleioylOleioyl -β-D--D-D- arabinosidearabinoside (5) (5)

밝은 노란색 반고체; [α]D 22 - 19.1 (c 0.1, MeOH); IR (KBr) νmax: 3415, 3345, 2905, 2843, 1721, 1650, 1451, 1374, 1213, 1038, 838 cm-1; 1H NMR (MeOD; 600 MHz); δ 5.37 (1H, m, H-9), 5.28 (1H, m, H-10), 4.43 (1H, d, J =7.5 Hz, H-1'), 4.12 (1H, m, H-2'), 3.89 (1H, m, H-3'), 3.74 (1H, m, H-4'), 3.63 (2H, br s, H2- 5'), 2.32 (2H, t, J =7.2 Hz), H2-2), 2.26 (2H, m, H2-11), 2.08 (2H, m, H2-8), 1.59 (2H, m, CH2), 1.31 (2H, m, CH2), 1.27 (18H, br s, 9 x CH2), 0.86 (3H, t, J = 6.0 Hz, Me); 13C NMR (MeOD, 150 MHz); 175.26 (C-1), 131.03 (C-9), 129.25 (C-10), 105.48 (C-1'), 71.29 (C-2'), 70.01 (C-3'), 66.37 (C-4'), 64.21 (C-5'), 35.07 (C-2), 33.21 (CH2), 32.80 (CH2), 30.91 (3 x CH2), 30.70 (4 x CH2), 30.61 (CH2), 30.35 (CH2), 29.28 (CH2), 28.30 (CH2), 26.67 (CH2), 26.13 (CH2), 23.87 (CH2), 14.58 (Me-18); ESI/MS m/z 415 [M+H]+ (C23H43O6); HR-ESI/FTMS m/z 415.3067 (calc. for C23H43O6; 415.3060).Light yellow semi-solid; [?] D 22 - 19.1 ( c 0.1, MeOH); IR (KBr)? Max : 3415, 3345, 2905, 2843, 1721, 1650, 1451, 1374, 1213, 1038, 838 cm -1 ; &Lt; 1 &gt; H NMR (MeOD; 600 MHz); δ 5.37 (1H, m, H -9), 5.28 (1H, m, H-10), 4.43 (1H, d, J = 7.5 Hz, H-1 '), 4.12 (1H, m, H-2' ), 3.89 (1H, m, H-3 '), 3.74 (1H, m, H-4'), 3.63 (2H, br s, H 2 - 5 '), 2.32 (2H, t, J = 7.2 Hz ), H 2 -2), 2.26 (2H, m, H 2 -11), 2.08 (2H, m, H 2 -8), 1.59 (2H, m, CH 2), 1.31 (2H, m, CH 2 ), 1.27 (18H, br s, 9 x CH 2 ), 0.86 (3H, t, J = 6.0 Hz, Me); &Lt; 13 &gt; C NMR (MeOD, 150 MHz); (C-2), 70.01 (C-3 '), 66.37 (C-4), 175.26 (C-1), 131.03 '), 64.21 (C-5 '), 35.07 (C-2), 33.21 (CH 2), 32.80 (CH 2), 30.91 (3 x CH 2), 30.70 (4 x CH 2), 30.61 (CH 2 ), 30.35 (CH 2 ), 29.28 (CH 2 ), 28.30 (CH 2 ), 26.67 (CH 2 ), 26.13 (CH 2 ), 23.87 (CH 2 ), 14.58 (Me-18); ESI / MS m / z 415 [ M + H] + (C 23 H 43 O 6); HR-ESI / FTMS m / z 415.3067 (calc. For C 23 H 43 O 6 ; 415.3060).

또한, 화합물 5의 묽은 염산으로의 가수분해 결과, 화합물 5는 β-D-아라비노스 및 올레산으로 가수분해됨을 알 수 있었고, 상기 결과를 종합하여, 화합물 5는 Oleioyl-β-D-arabinoside 이며, 구조가 도 5와 같음을 알 수 있었다. 도 5는 화합물 5의 구조 및 이의 단편화 패턴(우측)이다. Further, as a result of hydrolysis of Compound 5 to dilute hydrochloric acid, Compound 5 was found to be hydrolyzed to ? -D-arabinose and oleic acid. Based on the above results, Compound 5 is Oleioyl-? -D-arabinoside, The structure is shown in Fig. Figure 5 shows the structure of compound 5 and its fragmentation pattern (right).

Position Position 화합물1Compound 1 화합물2Compound 2 화합물3Compound 3 22 -- -- -- 33 6.60 br s6.60 br s 6.61 br s6.61 br s -- 44 -- -- -- 55 -- -- -- 66 7.46 d (2.5)7.46 d (2.5) 7.40 d (2.5)7.40 d (2.5) 7.31 d (3.0)7.31 d (3.0) 77 -- -- -- 88 6.80 d (2.5)6.80 d (2.5) 6.79 d (2.5)6.79 d (2.5) 6.80 d (3.9)6.80 d (3.9) 99 -- -- -- 1010 -- -- -- 1'One' -- -- -- 2'2' 6.71 br s6.71 br s 6.69 br s6.69 br s 7.03 d (7.8)7.03 d (7.8) 3'3 ' -- -- 7.44 d (7.8)7.44 d (7.8) 4'4' -- -- -- 5'5 ' 7.48 d (8.4)7.48 d (8.4) 7.41 d (7.8)7.41 d (7.8) 7.10 d (8.4)7.10 d (8.4) 6'6 ' 6.91 d (8.4)6.91 d (8.4) 6.90 d (7.8)6.90 d (7.8) 6.92 d (8.4)6.92 d (8.4) 1a1a 4.40 d (7.3)4.40 d (7.3) 5.28 d (4.5)5.28 d (4.5) 4.32 d (4.2)4.32 d (4.2) 2a2a 4.06 dd (7.3, 6.5)4.06 dd (7.3, 6.5) 4.21 dd (4.5, 6.3)4.21 dd (4.5, 6.3) 4.16 dd (4.2, 6.3)4.16 dd (4.2, 6.3) 3a3a 3.81 m3.81 m 3.57 m3.57 m 3.52 m3.52 m 4a4a 3.52 m3.52 m 3.46 m3.46 m 3.30 m3.30 m 5a5a 3.86 br s3.86 br s 3.83 d (6.2), 3.81 d (6.3)3.83 d (6.2), 3.81 d (6.3) 3.64 d (6.0), 3.67 d (5.8)3.64 d (6.0), 3.67 d (5.8) 1b1b 4.39 d (7.5)4.39 d (7.5) 5.15 d (5.6)5.15 d (5.6) 5.84 d (4.8)5.84 d (4.8) 2b2b 4.33 dd (7.5, 5.8)4.33 dd (7.5, 5.8) 4.23 dd (5.6, 6.1)4.23 dd (5.6, 6.1) 4.45 dd (4.8, 6.9)4.45 dd (4.8, 6.9) 3b3b 3.79 m3.79 m 3.52 m3.52 m 3.35 m3.35 m 4b4b 3.44 m3.44 m 3.44 m3.44 m 3.42 m3.42 m 5b5b 3.65 d (6.2), 3.69 d (6.5)3.65 d (6.2), 3.69 d (6.5) 3.70 d (6.8), 3.68 d (6.8)3.70 d (6.8), 3.68 d (6.8) 3.74 d (6.0), 3.72 d (7.8)3.74 d (6.0), 3.72 d (7.8) 1c1c 4.33 d (7.8)4.33 d (7.8) 5.05 d (5.2)5.05 d (5.2) 5.39 d (3.6)5.39 d (3.6) 2c2c 4.23 dd (7.8, 6.2)4.23 dd (7.8, 6.2) 4.01 dd (5.2, 5.8)4.01 dd (5.2, 5.8) 4.03 dd (3.6, 5.8)4.03 dd (3.6, 5.8) 3c3c 3.56 m3.56 m 3.50 m3.50 m 3.99 m3.99 m 4c4c 3.38 m3.38 m 3.41 m3.41 m 4.36 m4.36 m 5c5c 3.62 d (9.0), 3.60 d (9.0)3.62 d (9.0), 3.60 d (9.0) 3.65 d (6.5), 3.63 d (6.7)3.65 d (6.5), 3.63 d (6.7) 3.81 d (7.1), 3.78 d (7.2)3.81 d (7.1), 3.78 d (7.2) 1d1d -- 4.73 d (4.1)4.73 d (4.1) 5.95 d (6.6)5.95 d (6.6) 2d2d -- 4.44 dd (4.1, 6.2)4.44 dd (4.1, 6.2) 4.73 dd (6.6, 5.4)4.73 dd (6.6, 5.4) 3d3d 3.47 m3.47 m 4.09 m4.09 m 4d4d 3.39 m3.39 m 4.25 m4.25 m 5d5d 3.61 d (6.6), 3.59 d (6.6)3.61 d (6.6), 3.59 d (6.6) 3.88 d (7.2), 3.84 d (6.2)3.88 d (7.2), 3.84 d (6.2) 1''One'' -- -- -- 2''2'' 2.31 t (7.2)2.31 t (7.2) 2.33 t (7.2)2.33 t (7.2) 2.23 t (7.2)2.23 t (7.2) 3'' - 17''3 '' - 17 '' 1.59 - 1.141.59 - 1.14 2.24 - 1.15 m2.24 - 1.15 m -- 3'' - 15''3 '' - 15 '' -- -- 1.61 - 1.261.61 - 1.26 18''18 '' 0.88 t (6.5)0.88 t (6.5) 0.88 t (6.3)0.88 t (6.3) 16''16 '' -- -- 0.88 t (6.3)0.88 t (6.3) 7, 3' (OMe)7, 3 '(OMe) 3.91, 3.943.91, 3.94 3.91 br s, 3.88 br s3.91 br s, 3.88 br s --

Position Position 화합물 1Compound 1 화합물 2Compound 2 화합물 3Compound 3 22 159.32159.32 158.95158.95 157.67157.67 33 103.41103.41 104.93104.93 136.25136.25 44 184.12184.12 184.04184.04 177.44177.44 55 163.02163.02 164.88164.88 161.31161.31 66 110.74110.74 110.68110.68 112.40112.40 77 166.31166.31 166.48166.48 162.57162.57 88 105.66105.66 105.40105.40 95.7895.78 99 161.93161.93 162.99162.99 153.63153.63 1010 110.39110.39 111.67111.67 107.80107.80 1'One' 122.01122.01 123.45123.45 121.13121.13 2'2' 116.28116.28 116.94116.94 120.18120.18 3'3 ' 149.63149.63 149.69149.69 119.06119.06 4'4' 147.52147.52 147.12147.12 142.15142.15 5'5 ' 123.50123.50 129.67129.67 123.35123.35 6'6 ' 117.88117.88 117.21117.21 117.24117.24 1a1a 104.99104.99 102.25102.25 102.77102.77 2a2a 78.2478.24 78.6278.62 88.2988.29 3a3a 77.9377.93 77.9977.99 75.3875.38 4a4a 72.2472.24 72.5172.51 71.0671.06 5a5a 63.4563.45 63.4763.47 63.5963.59 1b1b 104.65104.65 100.12100.12 101.29101.29 2b2b 80.5780.57 80.5780.57 82.7782.77 3b3b 75.2875.28 77.3977.39 75.6275.62 4b4b 71.7571.75 72.3372.33 71.3571.35 5b5b 62.8162.81 62.8162.81 62.8062.80 1c1c 102.34102.34 101.79101.79 93.7793.77 2c2c 82.7382.73 79.2279.22 78.2078.20 3c3c 75.0675.06 74.5374.53 75.2075.20 4c4c 71.4571.45 71.7571.75 69.7169.71 5c5c 62.6362.63 62.6462.64 64.5364.53 1d1d -- 101.36101.36 91.3391.33 2d2d -- 82.5782.57 78.0178.01 3d3d -- 74.1974.19 72.7772.77 4d4d -- 71.4371.43 73.9873.98 5d5d -- 62.0762.07 62.6362.63 1''One'' 172.26172.26 166.48166.48 170.31170.31 2''2'' 35.9235.92 35.5335.53 35.5035.50 3'' - 17''3 '' - 17 '' 35.53 to 21.9935.53 to 21.99 30.89 - 22.1030.89 - 22.10 3'' - 15''3 '' - 15 '' -- -- 32.39 - 222.2932.39 - 222.29 18''18 '' 14.3514.35 18.0618.06 -- 16''16 '' -- -- 14.5714.57 7, 3' (OMe)7, 3 '(OMe) 56.84, 56.5056.84, 56.50 57.20, 56.8257.20, 56.82

positionposition 1H NMR 1 H NMR 13C NMR 13 C NMR 1One -- 142.82142.82 22 -- 166.28166.28 33 8.01 dd (7.2, 2.4)8.01 dd (7.2, 2.4) 137.34137.34 44 7.80 m7.80 m 125.01125.01 55 6.79 m6.79 m 138.23138.23 66 7.24 dd (7.8, 2.7)7.24 dd (7.8, 2.7) 147.15147.15 77 -- 169.81169.81 1a1a 5.89 d (4.8)5.89 d (4.8) 90.6590.65 2a2a 4.09 m4.09 m 82.5682.56 3a3a 3.88 m3.88 m 74.9174.91 4a4a 3.66 m3.66 m 73.9373.93 5a5a 3.69 br s3.69 br s 64.0864.08 1b1b 5.71 d (4.8)5.71 d (4.8) 102.92102.92 2b2b 4.07 m4.07 m 83.3883.38 3b3b 3.90 m3.90 m 78.0978.09 4b4b 3.65 m3.65 m 73.2473.24 5b5b 3.67 br s3.67 br s 65.1465.14 1c1c 5.39 d (3.7)5.39 d (3.7) 94.0194.01 2c2c 4.03 m4.03 m 83.2583.25 3c3c 3.87 m3.87 m 74.4074.40 4c4c 3.60 m3.60 m 73.0173.01 5c5c 3.65 d (6.5)3.65 d (6.5) 64.4664.46 1d1d 5.12 d (7.3)5.12 d (7.3) 93.7593.75 2d2d 4.01 m4.01 m 83.4983.49 3d3d 3.85 m 3.85 m 75.8375.83 4d4d 3.56 3.56 72.3872.38 5d5d 3.52 br s3.52 br s 64.6164.61 1e1e 4.75 d (4.8)4.75 d (4.8) 103.23103.23 2e2e 3.95 m3.95 m 83.7583.75 3e3e 3.82 m3.82 m 76.7976.79 4e4e 3.54 m3.54 m 71.7671.76 5e5e 3.57 d (6.6)3.57 d (6.6) 64.8864.88 1f1f 4.53 d (3.8)4.53 d (3.8) 98.2398.23 2f2f 4.02 m4.02 m 84.2184.21 3f3f 3.72 m3.72 m 77.7177.71 4f4f 3.58 m3.58 m 71.4571.45 5f5f 3.58 d (6.1)3.58 d (6.1) 62.8662.86 1g1g 4.46 d (4.6)4.46 d (4.6) 90.6590.65 2g2g 4.03 m4.03 m 84.6884.68 3g3g 3.68 m3.68 m 78.9478.94 4g4g 3.72 m3.72 m 71.0471.04 5g5g 3.30 d (5.8)3.30 d (5.8) 65.7765.77 1h1h 4.40 d (3.6)4.40 d (3.6) 90.3090.30 2h2h 4.17 m4.17 m 86.5486.54 3h3h 3.70 m3.70 m 79.4779.47 4h4h 3.75 m3.75 m 69.3469.34 5h5h 3.29 m3.29 m 65.3565.35 1'One' -- 174.23174.23 2'2' 2.68 m2.68 m 41.1741.17 3'3 ' 2.55 m2.55 m 39.2439.24 4'4' 1.35 m1.35 m 35.5435.54 5'5 ' 1.31 m1.31 m 31.1231.12 6'6 ' 1.27 m1.27 m 26.9526.95 7'7 ' 2.46 m2.46 m 39.4039.40 8'8' -- 181.37181.37 9'9 ' 1.13 d (6.4)1.13 d (6.4) 25.9025.90 10'10 ' -- 178.93178.93 OMeOMe 3.78 br s3.78 br s 54.8754.87

<< 실시예Example 2> 생물학적 활성 검토  2> Review of biological activity

벼의 생육은 조류의 활발한 생장으로 인해 저해되는데, 이는 조류의 생장으로 인해 벼가 생육하는 물의 온도가 낮아지고, 빛 차단으로 인해 광합성이 저해되기 ?문이다. 따라서 조류 blue-green algae (M. aeruginosa UTEX # 2388)를 대상으로 상기 실시예 1에서 분리된 신규 화합물 1 내지 5의 조류 생장 저해 활성을 검토하였다. The growth of rice is inhibited by the vigorous growth of algae, because the growth of algae lowers the temperature of the water in which the rice grows and the photosynthesis is inhibited by the light interception. Thus, algae blue-green algae ( M. aeruginosa UTEX &amp;num; 2388) were examined to examine the algae growth inhibitory activities of the novel compounds 1 to 5 isolated in Example 1 above.

blue-green algae M. aeuruginosa UTEX 2388은 Biological Resource Center (Korea Research Institute of Biological and Biotechnology, Daejeon, Korea)로부터 수득되었고, 주마다 배지를 바꾸며 25℃에서 Allen (1968) 배지 상에서 배양하였다. 조류(algae)에 대한 민감성을 조사하기 위해, 화합물 1-5는 디메틸설폭사이드(DMSO)로 희석되었고, 0.2 μm 필터(Satorius, Gottingen, Germany)로 여과한 후, 멸균된 Allen 배지에 최종농도 1, 10 및 100 mg/L가 되도록 가하였다. 시험 조류를 접종한 후, 상기 배양액은 25℃, 10시간 암조건/14시간 명조건(light intensity 60 μmol/m2 s)을 반복하며 배양되었다. M. aeruginosa 에 대한 항조류 활성은 상기 실시예 1에서 분리된 화합물 1-5 첨가 6일 후에 측정되었다. 배양 후, 각 액체 배양액 샘플을 흡광도 670nm인 LabSystems (Helsinki, Finland) type 352 microplate reader를 사용하여 측정하였고, 측정값은 건조 중량으로 환산하여 나타내었다. blue-green algae M. aeuruginosa UTEX 2388 is a member of the Biological Resource Center Biological and Biotechnology, Daejeon, Korea) and cultured on Allen (1968) medium at 25 ° C with changing media every week. Compound 1-5 was diluted with dimethylsulfoxide (DMSO), filtered through a 0.2 [mu] m filter (Satorius, Göttingen, Germany), and placed in sterile Allen medium at a final concentration of 1 , 10 and 100 mg / L, respectively. After inoculation of the test algae, the culture was incubated at 25 ° C. for 10 hours under the dark condition / 14 hours light intensity (60 μmol / m 2 s). M. aeruginosa Was measured 6 days after the addition of the compound 1-5 isolated in Example 1 above. After incubation, each liquid culture sample was measured using a LabSystems (Helsinki, Finland) type 352 microplate reader with an absorbance of 670 nm and the measured values were expressed in terms of dry weight.

결과를 도 6에 나타내었다. 도 6을 참조하면, 본 발명의 화합물인 화합물 5가 100 ppm (mg/L) 농도에서 가장 높은 M. aeuruginosa 저해 활성을 보임을 확인할 수 있었으며, 상기 농도에서, 건조중량(Dry Weight, DW) 및 화합물 5에 의한 생장 저해 효과는 각각 0.35 ± 0.01 mg/3 mL 및 92.6 ± 0.3 %로 나타났고, 유의성이 확인되었다(P < 0.0001). 또한, 10 ppm 농도에서, 화합물 5는 다른 화합물보다 높은 M. aeuruginosa 생장(mg/L) 저해 활성(11.6 ± 8.2 %) 을 보였다. 1 ppm 농도에서는 어떤 화합물도 M. aeuruginosa 생장 저해 활성을 보이지 않았다.
The results are shown in Fig. Referring to FIG. 6, the compound of the present invention, Compound 5, has the highest M. aeuruginosa at a concentration of 100 ppm (mg / L) (Dry weight, DW) and the inhibitory effect on growth by compound 5 were 0.35 ± 0.01 mg / 3 mL and 92.6 ± 0.3%, respectively, and the significance was confirmed ( P < 0.0001). Further, at a concentration of 10 ppm, Compound 5 was higher in M. aeuruginosa And the growth (mg / L) inhibitory activity (11.6 ± 8.2%). At 1 ppm concentration, no compound was found in M. aeuruginosa Growth inhibitory activity.

이상으로 본 발명의 특정한 부분을 상세히 기술하였는 바, 당업계의 통상의 지식을 가진 자에게 있어서, 이러한 구체적 기술은 단지 바람직한 실시예일 뿐이며, 이에 의해 본 발명의 범위가 제한되는 것이 아닌 점은 명백할 것이다. 따라서, 본 발명의 실질적인 범위는 첨부된 청구항들과 그것들의 등가물에 의하여 정의된다고 할 것이다. While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that such detail is solved by the person skilled in the art without departing from the scope of the invention. will be. Accordingly, the actual scope of the present invention will be defined by the appended claims and their equivalents.

Claims (8)

하기 화학식 1의 구조를 갖는 화합물:
[화학식 1]
Figure 112015013426938-pat00003

상기 화학식 1에서,
R1, R2 및 R3는 각각 하이드록시임.A compound having a structure represented by the following formula
[Chemical Formula 1]
Figure 112015013426938-pat00003

In Formula 1,
R 1 , R 2 and R 3 are each hydroxy. 삭제delete 제1항에 있어서,
상기 화합물은 볏짚으로부터 추출한 것인 화합물.The method according to claim 1,
Wherein said compound is extracted from rice straw. 볏짚을 메탄올에 침지시켜 볏짚의 메탄올 추출물을 제조하는 단계;
상기 메탄올 추출물과 물을 혼합하고 부탄올로 재추출하여 부탄올 추출물을 제조하는 단계; 및
상기 부탄올 추출물에 클로로폼 및 메탄올을 용리액으로 하는 컬럼 크로마토그래피를 실시하는 단계를 포함하는
볏짚으로부터 제1항에 따른 화합물을 추출하는 방법.Preparing a methanol extract of rice straw by immersing rice straw in methanol;
Mixing the methanol extract with water and re-extracting with butanol to prepare a butanol extract; And
Subjecting the butanol extract to column chromatography using chloroform and methanol as an eluent
A method for extracting a compound according to claim 1 from a rice straw. 제1항 또는 제3항 중 어느 한 항에 따른 화합물을 유효성분으로 함유하는 남조류의 생장 억제용 조성물. A composition for inhibiting the growth of a cyanobacterium comprising the compound according to any one of claims 1 to 3 as an active ingredient. 제5항에 있어서,
상기 남조류는 마이크로시스티스 애루기노사(Microcystis aeruginosa)인 것인 남조류의 생장 억제용 조성물. 6. The method of claim 5,
The cyanobacteria were obtained from Microcystis aeruginosa . &lt; / RTI &gt; 제1항 또는 제3항 중 어느 한 항에 따른 화합물을 남조류 배양액에 첨가하여 배양하는 단계를 포함하는 남조류의 생장 억제 방법.4. A method for inhibiting the growth of cyanobacteria comprising the step of culturing the compound according to any one of claims 1 to 3 in a cyanobacterium culture solution. 제7항에 있어서,
상기 화합물은 남조류 배양액 내에 5 내지 1000 mg/L의 농도로 첨가되는 것인 남조류의 생장 억제 방법.8. The method of claim 7,
Wherein said compound is added in a concentration of 5 to 1000 mg / L in a cyanobacterium culture solution.
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