KR101249850B1 - Composition and Method for Controling Post-harvest Disease of Citrus Fruit or Sweet Potato Using a Fruit Extract of Pittosporum tobira Ait or Saponin ⅢA3 Isolated from the Fruit Extract - Google Patents
Composition and Method for Controling Post-harvest Disease of Citrus Fruit or Sweet Potato Using a Fruit Extract of Pittosporum tobira Ait or Saponin ⅢA3 Isolated from the Fruit Extract Download PDFInfo
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Abstract
본 발명은 돈나무 열매 추출물, 돈나무 열매 추출물로부터 분리한 샤포닌 ⅢA3를 이용한 감귤 또는 고구마 저장병 방제제 조성물과 감귤 또는 고구마 저장병 방제 방법을 개시한다. 상기 돈나무 열매 추출물과 샤포닌 ⅢA3는 모두 감귤 또는 고구마 저장병의 주요 병원균인 페니실리움 디지타텀 및/또는 페니실리움 이탈리컴에 대해서 항곰팡이 활성을 보인다.The present invention discloses a citrus fruit or sweet potato storage bottle control composition and a method of controlling citrus fruit or sweet potato storage bottle using shaponin IIIA 3 isolated from the extract of the bilberry fruit and the bilberry fruit. Both the extract and Shaponin IIIA 3 show antifungal activity against penicillium digititatum and / or penicillium italicum, which are the main pathogens of citrus or sweet potato storage diseases.
Description
본 발명은 돈나무 열매 추출물 또는 그것으로 분리한 샤포닌 ⅢA3(saponin ⅢA3)를 이용한 감귤 또는 고구마 저장병 방제제 조성물 및 감귤 또는 고구마 저장병 방제 방법에 관한 것이다.
The present invention relates to a citrus or sweet potato storage bottle control composition and a method of controlling citrus fruit or sweet potato storage bottle using the extract of Donna fruit or saponin IIIA 3 (saponin IIIA 3 ) separated therefrom.
감귤 수확 후 유통 및 저장 중에 가장 문제가 되는 것은 페니실린계 곰팡이(Penicillium spp.)에 의해 감귤이 부패하는 감귤 저장병으로, 특히 저장 중에 심하게 발생하여 막대한 피해를 주고 있다. The biggest problem during distribution and storage after citrus harvesting is citrus storage bottle, which is corrupted by penicillium spp., Especially during storage, causing severe damage.
감귤 저장병을 일으키는 페니실린계 균들에는 감귤에 녹색 곰팡이병을 일으키는 페니실리움 디지타텀(P. digitatum), 청색곰팡이병을 일으키는 페니실리움 이탈리컴(P. italicum), 그리고 whisker mold를 일으키는 페니실리움 울라이엔세(P. ulaiense) 등이 보고되어 있으며, 그 중 대부분의 피해는 페니실리움 디지타텀(P. digitatum)과 페니실리움 이탈리컴(P. italicum)에 의한 것이다(Brown & Eckert, Compendium of Citrus Diseases 2nd, pp.41~42, 2000; Holmes et al., Phytopathology, 84, pp719~727, 1994).Penicillin-based gyundeul causing citrus storage disease, the cause of green mold disease on citrus Penny Room Solarium digital Tatum (P. digitatum), causing the blue mildew Penny Room Solarium Italy Com (P. italicum), and Penny chamber causing whisker mold Leeum Ulla two yen year-old is looking like (P. ulaiense), and most of that damage is due to the Penny room Solarium digital Tatum (P. digitatum) and Penny room Solarium Italy Com (P. italicum) (Brown & Eckert , Compendium of Citrus Diseases 2nd, pp. 41-42, 2000; Holmes et al., Phytopathology , 84, pp719-727, 1994).
이들에 대한 방제로는 약제 방제를 비롯한 여러 가지 방법들이 개발되고 있는데, 특히 미국에서는 이마자릴(Imazalil)를 이용한 약제방제가 보편화되고 있으며(Eckert 등, Plant Disease, 78, pp971~974, 1994; Schirra 등, Proc. Int. Soc. Citriculture, pp1060~1063, 1992; Smilanick 등, Plant Disease, 81, pp379~382, 1997), 여러 가지 무기성분들을 이용한 방제도 시도되고 있다. 또한 효모인 캔디다 올레오필라(Candida oleophila)와 세균인 슈도모나스 시린개(Pseudomonas syringae)를 이용한 미생물농약이 이미 상품화되어 각각 AspireTM와 BiosaveTM이란 상표명으로 시판되고 있으며, 이외에도 여러 가지 미생물을 이용한 생물적 방제가 시도되고 있다(Droby 등, Biological Control, 12, pp97~101, 1998; Arras, Postharvest Biology and Technology, 8, pp191~198, 1996).In order to control them, various methods including drug control have been developed. In particular, drug control using Imazalil is widely used in the United States (Eckert et al., Plant Disease, 78, pp971 to 974, 1994; Schirra). Et al., Proc. Int. Soc. Citriculture, pp 1060-1063, 1992; Smilanick et al., Plant Disease, 81, pp 379-382, 1997). Further biological using a number of micro-organisms in addition to yeast is Candida oleo pillar of microbial pesticides using (Candida oleophila) and the bacterium Pseudomonas ache dog (Pseudomonas syringae) is already commercialized, and is commercially available in the Aspire TM and Biosave TM is the tradename, respectively, Control has been attempted (Droby et al., Biological Control , 12, pp 97-101, 1998; Arras, Postharvest Biology and Technology , 8, pp 191-198, 1996).
한편 페니실리움 이탈리컴은 고구마를 16℃ 이하에서 저장할 때 다른 병원균에 고구마 조직이 병들었거나 상처가 생겼을 때 침입하여 고구마 저장병(고구마 푸른곰팡이병이라고도 함)을 일으킨다.On the other hand, when penicillium italicum stores sweet potatoes at 16 ° C or less, it invades other pathogens when the sweet potato tissue is sick or injured, causing sweet potato storage disease (also called sweet potato blue mold disease).
고구마의 병든 조직은 다소 단단한 편이며, 마르거나 약간 축축하기도 하며 갈색을 띤다. 병든 조직위에 푸른곰팡이가 피는 것이 특징이며 흰 균사덩어리가 보이기도 하는데 결국에는 푸른곰팡이 포장덩어리가 균사 위에 생긴다. The sweet tissue of sweet potatoes is rather hard, dry, slightly moist, and brown. It is characterized by the growth of blue mold on the diseased tissue, and the appearance of white mycelium masses. Eventually, the blue mold packaging mass forms on the hyphae.
고구마 저장병의 효과적인 방제 방법은 없으며, 다만 저장 시 상처가 생기지 않도록 주의하여 관리하고 저장 시 온도가 16℃ 이하가 되지 않도록 하는 방법들이 제안되고 있다. There is no effective control method for sweet potato storage bottles. However, methods are proposed to manage them carefully so as not to injure them during storage and to keep the temperature below 16 ° C.
본 발명은 감귤 또는 고구마 저장병을 일으키는 페니실리움 디지타텀 또는 페니실리움 이탈리컴에 항곰팡이 활성을 가지는 돈나무(Pittosporum tobira Ait.) 열매 추출물과 그 추출물에서 분리한 샤포닌 ⅢA3을 개시한다.
The present invention has antifungal activity against penicillium digititatum or penicillium italicomb causing citrus or sweet potato storage disease ( Pittosporum tobira Ait.) Fruit extract and chaponin IIIA 3 isolated from the extract are disclosed.
본 발명의 목적은 돈나무(Pittosporum tobira Ait.) 열매 추출물과 그 추출물에서 분리한 샤포닌 ⅢA3를 이용한 감귤 또는 고구마 저장병 방제제 조성물을 제공하는 데 있다.An object of the present invention is a Pittosporum tobira Ait.) The present invention provides a tangerine or sweet potato storage bottle control composition using fruit extract and chaponin IIIA 3 isolated from the extract.
본 발명의 다른 목적은 상기 조성물을 이용한 감귤 또는 고구마 저장병의 방제 방법을 제공하는 데 있다.
Another object of the present invention is to provide a method for controlling citrus or sweet potato storage bottles using the composition.
본 발명은 돈나무 열매의 80% 에탄올 추출물, 그 추출물의 부탄올 등의 분획물 그리고 그 분획물로부터 분리한 단일물질인 샤포닌 ⅢA3(saponin ⅢA3)이 감귤 또는 고구마 저장병의 주요 병원균인 페니실리움 디지타텀 및/또는 페니실리움 이탈리컴에 대해서 항곰팡이 활성을 가짐을 확인함으로써 완성된 것이다. The
돈나무 열매로부터 분리한 샤포닌 ⅢA3는 공지의 물질이고(Joseph D. Connolly et al., Nat . Prod . Rep ., 2005, 22:230-248; H. D'Acquarica et al., Tetrahedron 2002, 58:10127-10136), 그 화학식은 아래의 [화학식 1]에서 확인할 수 있으며, 그것의 IUPAC 명칭은 12-oleanene-3,15,16,28-tetraol-21-angeloyl-22-acetyl-3-O-[β-D-glucopyranosyl-(1→2)]-[a-L-arabinopyranosyl-(1→3)]-[α-L-arabinofuranosyl-(1→4)]-β-D-glucuronopyranoside이다.Chaponin IIIA 3 isolated from nectar fruit is a known substance (Joseph D. Connolly et al., Nat . Prod . Rep . , 2005, 22: 230-248; H. D'Acquarica et al., Tetrahedron 2002, 58: 10127-10136), its chemical formula can be found in [Formula 1] below, its IUPAC name is 12-oleanene-3,15,16,28- tetraol-21-angeloyl-22-acetyl-3-O- [β-D-glucopyranosyl- (1 → 2)]-[aL-arabinopyranosyl- (1 → 3)]-[α-L-arabinofuranosyl- (1 → 4)]-β-D-glucuronopyranoside.
상기 샤포닌 ⅢA3는 상기 인용된 문헌에 개시된 방법 또는 본 발명의 아래의 실시예에서 개시된 방법에 따라 분리될 수 있다. 상기 인용된 문헌은 본 명세서의 일부로서 간주 된다.
The chaponin IIIA 3 can be separated according to the method disclosed in the above cited document or the method disclosed in the following examples of the present invention. The documents cited above are considered part of this specification.
<샤포닌 ⅢA3>
<Shaponin IIIA 3>
전술한 바를 고려할 때, 본 발명의 감귤 또는 고구마 저장병 방제제 조성물은 돈나무 열매 추출물, 돈나무 열매 추출물의 분획물, 또는 그 돈나무 열매 추출물로부터 분리될 수 있는 샤포닌 ⅢA3를 유효성분으로 포함함을 특징으로 한다. In view of the foregoing, the tangerine or sweet potato storage bottle control composition of the present invention is characterized in that it comprises a saponin IIIA 3 which can be separated from the nectar fruit extract, a fraction of the nectar fruit extract, or the nectar fruit extract as an active ingredient. It is done.
본 명세서에서, 상기 "유효성분"의 의미는 단독으로 목적하는 활성을 나타내거나 또는 그 자체는 활성이 없는 담체와 함께 활성을 나타낼 수 있는 성분을 의미한다.In the present specification, the term "active ingredient" means a component that can exhibit activity alone or in combination with a carrier which is not active in itself.
또한 본 명세서에서, "돈나무 열매 추출물"은 추출 방법을 불문하고 추출 대상인 돈나무 열매를 메탄올, 에탄올, 부탄올 등의 탄소수 1 내지 5의 저급 알콜, 아세톤, 헥산, 에틸아세테이트, 디클로로메탄, 물 또는 이들의 혼합 용매로 추출하여 얻어진 추출물을 의미한다. 추출 방법을 불문하므로, 추출 대상을 추출 용매에 침지시키는 단계를 통하여 추출되는 한, 추출 방법은 냉침, 환류, 가온, 초음파 방사 등 임의의 방식이 모두 적용될 수 있는 것으로 이해되어야 한다. 그럼에도 상기 "돈나무 열매 추출물"은 바람직하게는 물, 에탄올 또는 이들의 혼합 용매, 더 바람직하게는 물과 에탄올의 혼합 용매, 특히 70~90%의 에탄올로 추출하고 얻어진 추출물을 의미한다. 추출물은 여과, 농축될 수 있으며 성상은 액상 또는 분말상일 수 있다. In addition, in the present specification, "pig tree fruit extract" refers to a pig tree fruit to be extracted, regardless of the extraction method, lower alcohols having 1 to 5 carbon atoms, such as methanol, ethanol, butanol, acetone, hexane, ethyl acetate, dichloromethane, water or their The extract obtained by extraction with a mixed solvent is meant. Regardless of the extraction method, it is to be understood that the extraction method may be applied to any method such as cooling, refluxing, heating, ultrasonic radiation, and the like, as long as the extraction object is extracted through immersion in the extraction solvent. Nevertheless, the term "donberry fruit extract" means an extract obtained by extracting with water, ethanol or a mixed solvent thereof, more preferably a mixed solvent of water and ethanol, in particular 70-90% ethanol. The extract may be filtered, concentrated and the phase may be liquid or powder.
또한 본 명세서에서, "돈나무 열매 추출물의 분획물"은 상기 돈나무 열매 추출물 바람직하게는 물과 에탄올의 혼합 용매, 특히 70~90%의 에탄올로 얻어진 돈나무 열매 추출물을 메탄올과 물의 혼합 용매 특히 10~40% 메탄올에 현탁시킨 후, 부탄올, 디클로로메탄, 에틸아세테이트 또는 헥산으로 분획하여 얻어진 어느 한 용매층의 분획물, 바람직하게는 부탄올로 분획하여 얻어진 어느 한 용매층의 분획물을 의미하며, 나아가 상기 돈나무 열매 추출물을 메탄올과 물의 혼합 용매 특히 10~40% 메탄올에 현탁시킨 후, 헥산, 디클로로메탄, 에틸아세테이트 및 부탄올을 이용하여 순차적으로 분획하여 얻어진 추출물, 바람직하게는 부탄올층의 분획물을 의미한다. 여기서 "순차적으로 분획한다"는 것의 의미는 물과 메탄올층의 분획물을 분획 후에도 계속 사용하여 상기 열거된 순서의 용매로 분획한다는 의미이다.In addition, in the present specification, "fraction of the bilberry fruit extract" is a bilberry fruit extract, preferably a mixture of water and ethanol, in particular 70 to 90% ethanol extract obtained from ethanol mixed solvent of methanol and water, particularly 10 to 40% After suspension in methanol, it means a fraction of any solvent layer obtained by fractionation with butanol, dichloromethane, ethyl acetate or hexane, preferably a fraction of any solvent layer obtained by fractionation with butanol. Means an extract obtained by suspending in a mixed solvent of methanol and water, in particular 10-40% methanol, and then sequentially fractionating with hexane, dichloromethane, ethyl acetate and butanol, preferably a fraction of the butanol layer. By "sequentially fractionating" here is meant that fractions of water and methanol layer continue to be used after fractionation with solvents in the order listed above.
또한 본 명세서에서, "방제"는 감귤 또는 고구마 저장병의 예방, 치료 또는 증상의 완화를 의미한다.Also herein, "control" means the prevention, treatment or alleviation of symptoms of citrus or sweet potato storage disease.
또한 본 명세서에서, "감귤"의 의미에는 하귤(C. natsudaidai Hayata), 유럽 남부 등지에서 재배되는 시트론(citron), 미국 캘리포니아 등지에서 재배되는 레몬(lemon), 열대 지방 등지에서 재배되는 문단이나 자몽 등의 문단류, 미국의 플로리디 등지에 재배되는 문단의 돌연변이종인 그레이프 프루트(grape fruit), 인도, 이탈리아 등지에서 재배되는 광귤(sour orange), 인도 등 세계 각지에서 재배되는 당귤, 중국이나 우리나라에서 재배되는 유자(柚子), 우리나라 제주도 등에서 재배되는 귤, 중국 등에서 재배되는 금감, 기타 탱귤 등이 모두 포함된다. In addition, in the present specification, "citrus" means a citrus ( C. natsudaidai Hayata), citron grown in southern Europe, lemon (lemon) grown in California, the United States, paragraph or grapefruit grown in the tropics, etc. Paragraphs, such as grape fruit grown in the US, Floridi, etc., grape fruit, sour oranges grown in India, Italy, etc. It includes all the citrons grown in Korea, tangerines grown in Jeju Island, Korea, gold persimmons grown in China, and other tangerines.
본 발명의 방제제 조성물에서 유효성분은 본 발명의 방제제 조성물 전체 중량을 기준으로 그것의 제형, 그것의 사용 시기(수확 직후, 수확 후 저장 직전 등) 등에 따라 1 내지 99 중량%의 범위 내에서 임의의 양으로 포함될 수 있는데, 통상적으로는 1 내지 30 중량%의 범위로 포함될 것이며, 액제에서는 통상 10 내지 20 중량%, 분제에서는 통상 30 내지 40 중량% 범위로 포함될 것이다.The active ingredient in the control composition of the present invention is in the range of 1 to 99% by weight based on the total weight of the control composition of the present invention according to its formulation, its use time (right after harvest, immediately after harvest, etc.), and the like. It may be included in any amount, it will usually be included in the range of 1 to 30% by weight, usually in the liquid formulation will be included in the range of 10 to 20% by weight, in powder powder usually 30 to 40% by weight.
본 발명의 방제제 조성물은 유효성분들의 제형 그대로 제조되거나, 농약학적으로 허용 가능한 담체와 혼합되어 유제, 용액제, 현탁제, 수화제, 유동제, 분제, 과립제, 분산제 등으로 제형화될 수 있다. The control composition of the present invention may be prepared as a formulation of the active ingredients, or may be mixed with an agriculturally acceptable carrier to be formulated into an emulsion, solution, suspension, hydrating agent, flow agent, powder, granule, dispersant, and the like.
상기에서 "농약학적으로 수용 가능한 담체"는 본 발명의 방제제 조성물의 유효성분과 배합되어 그 유효성분의 활성을 저해하지 않으면서 그 유효성분의 살포, 저장 및/또는 운반을 촉진시키거나 저해시키지 않고 식물이나 인체에 허용 가능한 이상의 독성을 나타내지 않는 임의의 물질을 말한다. In the above, "agrochemically acceptable carrier" is combined with the active ingredient of the control agent composition of the present invention without promoting or inhibiting the spreading, storage and / or transport of the active ingredient without inhibiting the activity of the active ingredient. Any substance that does not exhibit more than acceptable toxicity to plants or the human body.
사용될 수 있는 담체는 토양 천연 광물(예를 들면 카올린, 점토, 활석, 초크), 토양 합성 광물(예를 들면 고분산 실리카, 실리케이트), 탄소 기재 물질(목탄, 역청 등), 황, 천연 또는 합성 수지, 비료, 셀룰로스 기재 물질(톱밥 및 옥수수 속대), 물, 방향족 용매(예: 솔베소 프로덕츠, 자일렌), 파라핀(예를 들면 광유 분획), 알코올(예를 들면 메탄올, 부탄올, 펜탄올, 벤질 알코올), 케톤(예를 들면 시클로헥사논, 메틸 히드록시부틸 케톤, 디아세톤 알코올, 메시틸 옥사이드, 이소포론), 락톤(예를 들면 감마-부티로락톤), 피롤리돈(피롤리돈, N-메틸피롤리돈, N-에틸피롤리돈, n-옥틸피롤리돈), 아세테이트(글리콜 디아세테이트), 글리콜, 디메틸 지방산 아미드, 지방산, 지방산 에스테르, 및 이들의 혼합물 등을 들 수 있다.Carriers that can be used are soil natural minerals (e.g. kaolin, clay, talc, chalk), soil synthetic minerals (e.g. highly dispersed silica, silicate), carbon based materials (charcoal, bitumen, etc.), sulfur, natural or synthetic Resins, fertilizers, cellulose based materials (sawdust and corncobs), water, aromatic solvents (e.g. Solvesso products, xylene), paraffins (e.g. mineral oil fractions), alcohols (e.g. methanol, butanol, pentanol, Benzyl alcohol), ketones (e.g. cyclohexanone, methyl hydroxybutyl ketone, diacetone alcohol, mesityl oxide, isophorone), lactones (e.g. gamma-butyrolactone), pyrrolidone (pyrrolidone) , N-methylpyrrolidone, N-ethylpyrrolidone, n-octylpyrrolidone), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids, fatty acid esters, and mixtures thereof. .
본 발명의 방제제 조성물은 또한 습윤제, 분산제, 부동제, 증점제, 보존제, 전착제 등 하나 이상의 보조제를 포함할 수 있다.The control composition of the present invention may also include one or more adjuvants such as wetting agents, dispersants, antifreezes, thickeners, preservatives, electrodeposition agents.
이러한 보조제는 당업계에서 공지된 것들 중에서 적절한 것을 선택하여 사용할 수 있는데, 예컨대 습윤제로서는 알킬나프탈렌 술포네이트(특히 디이소프로필나프탈렌술포네이트 또는 디이소부틸나프탈렌술포네이트)를 사용할 수 있고, 분산제로서는 비이온성 분산제(에틸렌 옥사이드/프로필렌 옥사이드 블록중합체, 알킬페놀 폴리글리콜 에테르, 트리스티릴페놀 폴리글리콜 등), 음이온성 분산제(리그닌술폰산, 나프탈렌술폰산, 페놀술폰산, 디부틸나프탈렌술폰산, 알킬아릴술포네이트, 알킬 술페이트, 알킬술포네이트 등) 또는 이들의 혼합물을 사용할 수 있으며, 부동제로서는 메탄올, 에탄올, 이소프로판올, 부탄올, 글리콜, 글리세린, 디에틸렌글리콜 등을 사용할 수 있고, 증점제로서는 셀룰로즈 유도체, 폴리아크릴산 유도체, 잔탄, 개질된 점토 등을 사용할 수 있으며, 보존제로서는 디클로로펜, 이소티아졸렌, 벤질 알코올 등을 사용할 수 있으며, 전착제는 폴리비닐알코올, 폴리비닐피롤리돈, 폴리아크릴레이트, 폴리메타크릴레이트, 폴리부텐, 폴리이소부틸렌, 폴리스티렌, 폴리에틸렌아민, 폴리에틸렌아미드, 폴리에틸렌이민, 폴리에테르 등을 사용할 수 있다.Such adjuvants may be selected and used appropriately from those known in the art, for example, alkylnaphthalene sulfonate (particularly diisopropylnaphthalenesulfonate or diisobutylnaphthalenesulfonate) may be used as the wetting agent, and nonionic as a dispersant. Dispersants (ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers, tristyrylphenol polyglycols, etc.), anionic dispersants (ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfides) Pate, alkylsulfonate, etc.) or mixtures thereof, methanol, ethanol, isopropanol, butanol, glycol, glycerin, diethylene glycol and the like can be used, and as a thickener, cellulose derivatives, polyacrylic acid derivatives, xanthan Modified clay As the preservative, dichlorophene, isothiazolene, benzyl alcohol, etc. can be used, and the electrodeposition agent is polyvinyl alcohol, polyvinylpyrrolidone, polyacrylate, polymethacrylate, polybutene, polyisobutylene , Polystyrene, polyethyleneamine, polyethyleneamide, polyethyleneimine, polyether and the like can be used.
다른 측면에 있어서, 본 발명은 전술한 바의 본 발명의 방제제 조성물을 이용한 감귤 또는 고구마 저장병 방제 방법에 관한 것이다.In another aspect, the present invention relates to a method for controlling citrus or sweet potato storage bottles using the control composition of the present invention as described above.
본 발명의 감귤 또는 고구마 저장병 방제 방법은 본 발명의 방제제 조성물을 감귤 또는 고구마에 접촉시키는 단계를 포함함을 특징으로 한다.The method for controlling citrus or sweet potato storage bottles of the present invention is characterized by comprising the step of contacting the control composition of the present invention with citrus or sweet potato.
상기 접촉시키는 단계는 통상적으로 수확 후 또는 유통 중의 감귤 또는 고구마에 직접적으로 살포함으로써 이루어질 것이나, 수확 직전에 살포하거나 감귤 또는 고구마 저장고를 훈증 처리함에 의해 살포할 수도 있다.
The contacting step will typically be accomplished by spraying directly on the citrus or sweet potato after harvest or in circulation, but may also be applied by spraying just before harvest or by fumigation of the citrus or sweet potato cellar.
전술한 바와 같이, 본 발명에 따르면, 돈나무 열매 추출물과 그 추출물에서얻은 분획물, 또는 그 분획물로부터 분리한 활성물질을 이용한 감귤 또는 고구마 저장병 방제제 조성물과 그 조성물을 이용한 감귤 또는 고구마 저장병 방제제 조성물을 제공할 수 있다.
As described above, according to the present invention, a citrus or sweet potato storage bottle control composition using a donut fruit extract and a fraction obtained from the extract, or an active substance isolated from the fraction and a tangerine or sweet potato storage bottle control agent using the composition A composition can be provided.
도 1은 돈나무 열매 80% 에탄올 추출물 및 그것의 분획물 제조 과정의 모식도이다.
도 2는 돈나무 열매 80% 에탄올 추출물과 그것의 분획물의 항곰팡이 활성을 나타낸 결과이다.
도 3은 돈나무 열매 부탄올 분획물의 14개 1차 정제물의 항곰팡이 활성을 나타낸 결과이다.
도 4는 1차 정제물 중 가장 항곰팡이 활성이 우수한 12번 정제물로부터 얻은 13개의 2차 정제물 중 가장 활성이 높은 11번 정제물의 항곰팡이 활성을 나타낸 결과이다.
도 5는 활성물질 분리 과정의 모식도이다.
도 6은 활성물질인 샤포닌 ⅢA3(2차 정제물 중 11번 정제물)의 1H NMR 스펙트럼이다.
도 7은 활성물질인 샤포닌 ⅢA3(2차 정제물 중 11번 정제물)의 13C NMR 스펙트럼이다.
도 8은 활성물질인 샤포닌 ⅢA3(2차 정제물 중 11번 정제물)의 DEPT 스펙트럼이다.
도 9는 활성물질인 샤포닌 ⅢA3(2차 정제물 중 11번 정제물)의 LC-MS/MS 스펙트럼이다.Figure 1 is a schematic diagram of the production process of 80% ethanol extract and fractions thereof.
Figure 2 is a result showing the antifungal activity of 80% ethanol extract and its fractions.
Figure 3 is the result showing the antifungal activity of the 14 primary purification of the Prunus butanol fraction.
Figure 4 shows the antifungal activity of the eleventh tablet of the highest activity among the 13 secondary tablets obtained from the
5 is a schematic diagram of an active material separation process.
FIG. 6 is a 1H NMR spectrum of an active substance, chaponin IIIA 3 (purification No. 11 in the secondary purification).
Figure 7 is a 13C NMR spectrum of the active substance chaponin IIIA 3 (
8 is a DEPT spectrum of an active substance, saponin IIIA 3 (purification No. 11 in the secondary purification).
9 is an LC-MS / MS spectrum of the active substance chaponin IIIA 3 (
이하 본 발명을 실시예 및 실험예를 참조하여 설명한다. 그러나 본 발명의 범위가 이러한 실시예 및 실험예에 한정되는 것은 아니다.Hereinafter, the present invention will be described with reference to Examples and Experimental Examples. However, the scope of the present invention is not limited to these examples and experimental examples.
<< 실시예Example 1> 1> 돈나무Wicker 열매 추출물 및 Fruit extract and 분획물의Fraction 제조 Produce
분쇄한 돈나무 열매 1kg을 80% 에탄올에 넣고 48시간 동안 침지시켜 3회 반복 추출한 후 여과하여 얻어진 추출액을 감압 농축하여 용매를 제거하고 동결건조하여 분말상의 추출물 228g(22.8%)을 얻었다.1 kg of crushed pork fruit was put in 80% ethanol, immersed for 48 hours, extracted three times, and the extract obtained by filtration was concentrated under reduced pressure to remove the solvent and lyophilized to obtain 228 g (22.8%) of a powdery extract.
그리고 상기 얻어진 에탄올 추출물 100g을 100배량의 20% 메탄올로 현탁 및 용해시킨 후에 헥산(n-hexane), 디클로로메탄(CH2Cl2), 에틸아세테이트(EtOAc) 및 부탄올(BuOH)로 순차적으로 분획하여 헥산층에서 9.46g(9.46%), 디클로로메탄층에서 4.42g(4.42%), 에틸아세테이트층에서 9.71g(9.71%), 부탄올층에서 23.8g(23.8%) 및 잔여 물층에서 52.12g(52.12%)의 분획물을 얻었다.Then, 100 g of the obtained ethanol extract was suspended and dissolved in 100% of 20% methanol, and then sequentially partitioned into hexane (n-hexane), dichloromethane (CH 2 Cl 2 ), ethyl acetate (EtOAc) and butanol (BuOH). 9.46g (9.46%) in hexane layer, 4.42g (4.42%) in dichloromethane layer, 9.71g (9.71%) in ethyl acetate layer, 23.8g (23.8%) in butanol layer and 52.12g (52.12%) in residual water layer Fractions).
상기 80% 에탄올 추출물 및 80% 에탄올 추출물로부터의 분획물의 제조 과정의 모식도를 도 1에 도시되어 있다.A schematic diagram of the preparation of fractions from the 80% ethanol extract and 80% ethanol extract is shown in FIG. 1.
<< 실시예Example 2> 2> 돈나무Wicker 열매 추출물과 Fruit extract 분획물의Fraction 녹색곰팡이병Green mold disease 곰팡이( mold( P. digitatumP. digitatum ) 및 ) And 청색곰팡이병Blue Mold Disease 곰팡이( mold( P. P. italicumitalicum )에 대한 ) For 항곰팡이Antifungal 활성 평가 Activity evaluation
돈나무 열매 추출물의 곰팡이에 대한 균사체 형성 억제능력을 평가하기 위하여, 녹색곰팡이병 및 청색곰팡이병 곰팡이 각각을 감자한천배지(PDA, potato dextrose agar) 상에서 5일간 배양 후 균총들의 가장자리에서 직경 6mm의 균사절편을 채취하여 50mg/mL 농도의 돈나무 열매 추출물과 분획물 40㎕를 직경이 8mm인 paper disk에 떨어뜨린 후 감자한천 배지에 접종하고 27℃에서 7일간 배양하여 균총의 생성을 측정하였다. To evaluate the mycelial formation inhibitory ability of fungi extracts on fungi, green fungal and blue fungal fungi were cultured on potato agar medium (PDA, potato dextrose agar) for 5 days and then mycelial slices of
그 결과를 도 2에 나타내었는데, 돈나무 분획물 중 부탄올 분획물에서 80% 에탄올 추출물 대비 가장 뛰어난 항곰팡이 활성이 관찰되었다(1과 5, (-)control; 2, 물 분획물; 3, 80% EtOH; 4, 부탄올 분획물; 6, 에틸아세테이트 분획물; 7, 디클로로메탄 분획물; 8, 헥산 분획물).The results are shown in Figure 2, the best anti-fungal activity was observed in the butanol fraction of the Pleurotus fraction compared to 80% ethanol extract (1 and 5, (-) control; 2, water fraction; 3, 80% EtOH; 4 , Butanol fraction; 6, ethyl acetate fraction; 7, dichloromethane fraction; 8, hexane fraction).
<< 실시예Example 3> 3> 돈나무Wicker 열매 Fruit 분획물Fraction 중 유효성분 분리·정제 및 그 Active ingredient separation and purification and its 정제물의Purified 녹rust 색곰팡이병 곰팡이(Mold fungus P. P. digitatumdigitatum ) 및 ) And 청색곰팡이병Blue Mold Disease 곰팡이( mold( P. P. italicumitalicum )에 대한 ) For 항term 곰팡이 활성 평가Fungal activity evaluation
상기에서 가장 활성이 뛰어난 것으로 확인된 부탄올 분획물 10g을 역상실리카겔을 이용해 컬럼크로마토그래피를 실시하여 총 14개의 1차 정제물을 얻었다. 컬럼의 크기는 7cm X 15cm 이며 20, 40, 60, 80, 100% 메탄올을 이동상으로 사용하였다. 14개의 1차 정제물에 대해서 상기 <실시예 2>와 동일한 방법으로 항곰팡이 활성을 평가하였는데, 그 결과 도 3에서 확인되는 바와 같이 12번(PTO-B-12)의 정제물의 항곰팡이 활성이 우수하여 12번 정제물 1.2g에 대해 순상실리카겔 컬럼크로마토그래피를 실시하였다. 컬럼의 크기는 2.5cm X 50cm 이며 클로로포름 : 메탄올(3:1, 1:1, v/v)을 이동상으로 사용하였다. 분당 1.5ml의 속도로 이동상을 흘려주었으며 총 13개의 2차 정제물을 얻었다.10 g of butanol fraction identified as the most active above was subjected to column chromatography using reverse phase silica gel to obtain a total of 14 primary purified products. The column size was 7 cm × 15 cm and 20, 40, 60, 80, 100% methanol was used as the mobile phase. Antifungal activity of 14 primary tablets was evaluated in the same manner as in <Example 2>. As a result, the antifungal activity of the purified product of No. 12 (PTO-B-12) was Pure silica gel column chromatography was performed on 1.2 g of the purified product No. 12. The column size was 2.5 cm × 50 cm and chloroform: methanol (3: 1, 1: 1, v / v) was used as the mobile phase. The mobile phase was flowed at a rate of 1.5 ml per minute and a total of 13 secondary purifications were obtained.
상기 총 13개의 2차 정제물에 대해서도 마찬가지로 상기 <실시예 2>와 동일한 방법으로 항곰팡이 활성을 평가하였는데, 그 결과 2차 정제물 중 11번 정제물(PTO-B-12-11)의 활성이 가장 높게 나타났다. 11번 2차 정제물의 항곰팡이 활성을 도 4에 나타내었다.Similarly, the antifungal activity was evaluated in the same manner as in <Example 2> with respect to the total 13 secondary tablets, and as a result, the activity of the 11th purified product (PTO-B-12-11) in the secondary tablets Was the highest. The antifungal activity of No. 11 secondary tablets is shown in FIG. 4.
상기 11번 정제물을 TLC(실리카겔 60 F 254 , 클로로포름;메탄올=2:3, v/v)에 전개했을 때 Rf는 0.7이며 단일 스팟으로 나타났다. The purified
도 5에 활성물질의 분리 과정을 모식도로 나타내었다. 5 is a schematic diagram showing the separation process of the active material.
<< 실시예Example 4> 4> 활성물질의 동정Identification of active substances
분리된 활성물질의 구조를 분석하기 위해 정제물 20mg을 메탄올-d4에 녹여 NMR spectrum을 측정하였다. 1H NMR 스펙트럼(도 6)에서 10개의 메틸기를 확인했으며 그 중 하나는 아세틸기에 연결된 메틸기(d 2.04ppm ,s)임을 확인했다. 또한 5-3.0ppm 부근의 시그널들로 미루어 배당체 형태임을 예상하였으며 5.5-5.8ppm부근의 시그널로 미루어 이중결합의 존재를 확인할 수 있었다. To analyze the structure of the isolated active material, 20 mg of the purified product was dissolved in methanol-d4 and the NMR spectrum was measured. In the 1 H NMR spectrum (FIG. 6), 10 methyl groups were identified, and one of them was identified as a methyl group (d 2.04 ppm, s) linked to an acetyl group. In addition, it was expected that the glycoside was formed by the signals around 5-3.0ppm, and the presence of the double bond was confirmed by the signal around 5.5-5.8ppm.
13C NMR 스펙트럼(도 7)에서 아세틸기의 카르보닐 탄소(173.0ppm)와 더불어 2개(176.3, 169.5ppm)의 카르보닐기의 존재를 확인하였다. 또한 127.0, 129.4, 139.2, 143.6ppm 의 시그널로 미루어 2개의 이중결합을 확인하였고 108.3, 105.8, 104.2, 103.0에서 당 4개의 아노머탄소들로 미루어 4개의 당이 배당체로 붙어 있음을 예상하였다. 13C NMR spectrum (FIG. 7) confirmed the presence of two carbonyl groups (176.3, 169.5 ppm) together with carbonyl carbon (173.0 ppm) of the acetyl group. In addition, two double bonds were identified by signals of 127.0, 129.4, 139.2, and 143.6ppm, and four sugars were expected to be attached as glycosides with four anomer carbons per 108.3, 105.8, 104.2, and 103.0.
또한 DEPT 스펙트럼(도 8)에서 11개의 4차 탄소, 28개의 CH, 10개의 CH2, 10개의 CH3를 확인하여 화합물의 총 탄소수는 59임을 알 수 있었다. 따라서 문헌[H. D'Acquarica et al., Tetrahedron 2002, 58: 10127-10136]을 검색한 결과 활성물질의 구조는 Saponin IIIA3 로 동정하였다.In addition, 11 quaternary carbons, 28 CH, 10 CH 2 , and 10 CH 3 were identified in the DEPT spectrum (FIG. 8), and the total carbon number of the compound was 59. Thus, H. D'Acquarica et al., Tetrahedron 2002, 58: 10127-10136] identified the structure of the active substance as Saponin IIIA 3 .
동정된 물질의 분자량을 측정하기 위해 LC-MS/MS 분석을 실시했다. Saponin IIIA3의 분자량은 1232.58이며 LC-MS/MS 분석결과 소듐이 결합된 형태인 1256.12로 분석되었다. 좀 더 정확한 구조 확인을 위해 MS/MS를 수행한 결과 도 9과 같이 Saponin IIIA3 고유의 쪼개짐 패턴을 얻을 수 있었다.
LC-MS / MS analysis was performed to determine the molecular weight of the identified material. Saponin IIIA 3 had a molecular weight of 1232.58 and was analyzed to be 1256.12 in sodium-bound form by LC-MS / MS analysis. As a result of performing MS / MS for more accurate structure confirmation, a cleavage pattern unique to Saponin IIIA 3 was obtained as shown in FIG. 9.
Claims (7)
A citrus fruit or sweet potato reservoir control composition comprising (i) a bilberry fruit extract, (ii) a fraction of a bilberry fruit extract, and (iii) at least one selected from the group consisting of chaponin IIIA 3 as an active ingredient.
상기 추출물은 물과 에탄올의 혼합 용매에 돈나무 열매를 침지시켜 얻어진 것을 특징으로 하는 감귤 또는 고구마 저장병 방제제 조성물.
The method of claim 1,
The extract is citrus or sweet potato storage bottle control composition, characterized in that obtained by immersing the donut fruit in a mixed solvent of water and ethanol.
상기 분획물은 하기 (Ⅰ) 및 (Ⅱ) 중 하나인 것을 특징으로 하는 감귤 또는 고구마 저장병 방제제 조성물
(Ⅰ) 물과 에탄올의 혼합 용매에 돈나무 열매를 침지시켜 얻어진 추출물을 메탄올과 물의 혼합 용매에 현탁시킨 후, 부탄올로 분획하여 얻어진 부탄올층의 분획물; 및
(Ⅱ) 물과 에탄올의 혼합 용매에 돈나무 열매를 침지시켜 얻어진 추출물을 메탄올과 물의 혼합 용매에 현탁시킨 후 헥산, 디클로로메탄, 에틸아세테이트 및 부탄올을 이용하여 순차적으로 분획하였을 때 얻어지는 부탄올층의 분획물.
The method of claim 1,
The fraction is a citrus or sweet potato storage bottle control composition, characterized in that one of the following (I) and (II)
(I) a fraction of the butanol layer obtained by dividing the extract obtained by immersing a bilberry fruit in a mixed solvent of water and ethanol in a mixed solvent of methanol and water, and then fractionating with butanol; And
(II) Fraction of the butanol layer obtained when the extract obtained by immersing the donut fruit in the mixed solvent of water and ethanol is suspended in the mixed solvent of methanol and water, and then fractionated using hexane, dichloromethane, ethyl acetate, and butanol sequentially.
상기 에탄올과 물의 혼합 용매는 70~90%의 에탄올인 것을 특징으로 하는 감귤 또는 고구마 저장병 방제제 조성물.
The method of claim 2,
The mixed solvent of ethanol and water is citrus or sweet potato storage bottle control composition, characterized in that 70 to 90% ethanol.
상기 에탄올과 물의 혼합 용매는 70~90%의 에탄올이고, 상기 메탄올과 물의 혼합 용매는 10~40%의 메탄올인 것을 특징으로 하는 감귤 또는 고구마 저장병 방제제 조성물.
The method of claim 3,
The mixed solvent of ethanol and water is 70 to 90% ethanol, the mixed solvent of methanol and water is 10 to 40% methanol, citrus or sweet potato storage bottle control composition.
상기 조성물은 농약학적으로 허용 가능한 담체와, 습윤제, 분산제, 부동제, 증점제, 보존제 및 전착제로 구성된 군에서 선택된 하나 이상의 보조제를 추가로 포함하는 것을 특징으로 하는 감귤 또는 고구마 저장병 방제제 조성물.
The method of claim 1,
The composition of claim 1, wherein the composition further comprises an agriculturally acceptable carrier and at least one auxiliary agent selected from the group consisting of wetting agents, dispersants, antifreeze agents, thickeners, preservatives and electrodeposition agents.
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