JP4583934B2 - アシルCoA:コレステロールアシルトランスフェラーゼの阻害活性を有する化合物またはその塩を有効成分とする殺虫剤 - Google Patents
アシルCoA:コレステロールアシルトランスフェラーゼの阻害活性を有する化合物またはその塩を有効成分とする殺虫剤 Download PDFInfo
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Description
本発明は、アシルCoA:コレステロールアシルトランスフェラーゼの阻害活性を有する化合物またはその塩を有効成分とする殺虫剤に関する。
従来、農業生産物および加工物の生産性の増大、衛生昆虫の防除と山林保護のために、有機合成殺虫剤が広く用いられてきた。しかしながら、数十年にわたった連続使用と乱用により、天敵を用いた生物学的防除系に悪影響を及ぼし、害虫の異常発現または抵抗性害虫の出現、人間を始めとする非標的微生物への毒性発現および環境汚染などの多くの副作用を引き起こすことになった。
本発明では、幼虫のステロール代謝において、貯蔵型ステロールまたは各種のホルモン生成に重要な役割をするものと知られているステロールアシル化酵素を新たな概念の目標指向的な探索系として使用して、天然資源からは新たな活性物質を探索し、阻害活性物質を分離精製して構造を糾明し、既に合成されているアシルCoAコレステロールアシルトランスフェラーゼ阻害活性を有する有機合成物を、本発明の検索系において活性を評価し、酵素阻害活性を確認した物質を、種々の幼虫に処理した結果、活性物質が幼虫に対して生物活性を示すことを確認して、本発明を完成するに至った。
本発明の前記およびほかの目的、特徴および利点は添付図面を参考する以降の詳細な説明からより明らかに理解可能であろう。
前記目的を達成するために、本発明は、アシルCoA:コレステロールアシルトランスフェラーゼの阻害活性を有する化合物またはその塩を有効成分とする殺虫剤を提供する。
以下、本発明を添付図面を参照する下記実施例に基づいてより詳しく説明する。しかしながら、下記実施例は、単に本発明を例示するためのものであり、本発明の範囲を限定するものではない。
<アシルCoA:コレステロールアシルトランスフェラーゼ阻害物質の製造>
(1)本発明で用いられる生産菌株のペニシリウムグリセオフルビン F1959は、韓国慶尚北道蔚山において採取した土壌から分離した菌であって、菌学的研究によりペニシリウムグリセオフルビンと判明され、本発明者等は、生命工学研究所韓国種菌協会にペニシリウムグリセオフルビン F1959として寄託し、寄託番号KCTC 0387BPを付与された。
(1)紫外線−可視光線分析
前記実施例1で得られたステロール代謝活性阻害物質の構造を決定するために、紫外線−可視光線吸光度分析を行った。具体的には、前記実施例1で得られた化合物を100%メタノールに溶かし、紫外線−可視光線分光器(Shimazu社、UV−265)を用いて吸収波長を分析した。
赤外線(IR)吸光度分析は、活性物質試料2mgをクロロホルムに溶かし、AgBrを塗った後乾燥して、比率記録型赤外線分光器(Bio−Rad Digilab Division、FTS−80)で分析した。
前記実施例1で得られた化合物の分子量を分析するために、VGZAB−7070質量分析器を用いて、高分解能質量分析を行った。
前記実施例1で得られた化合物の構造を調べるために、核磁気共鳴(NMR)分析を行った。前記化合物10mgを完全乾燥し、CDCl3に溶かして、5mmNMRチューブに入れ、Varian Unity−500機種でNMR分析を行った。1H−NMRは500.13MHzで核磁気共鳴スペクトルを測定した。結果は、下記図1〜4に示した。
アシルCoA:コレステロールアシルトランスフェラーゼ活性阻害(以下、「ACAT」という。)物質の活性測定は、Brecher法を若干修正して用いた[Brecher.P and C.Chen;Biochimica Biophysica Acat 617:458〜471,1980]。この方法は、アシルCoA:コレステロールアシルトランスフェラーゼ活性酵素原としては、肝から部分精製したミクロソームを用いており、基質としてはコレステロールと放射能で標識されたオレオイルCoAを反応させるものであり、反応生成物であるコレステロールエステルに含まれた放射能の量で反応程度を測定した。
阻害活性(%)=[1−(T−B/C−B)]×100
(前記式中、T:酵素反応液に試料を入れた試験区におけるcpm値、C:酵素反応液に試料を入れなかった対照区におけるcpm値、B:酵素原を入れず、試料を入れた対照区のcpm値。)
前記ACAT阻害率を測定した結果、
pyripyropene A(化学式1)は、酵素の活性を50%阻害する濃度、すなわちIC50が35ng/mlであり、分子量が583であるので、0.060nMとして計算された。
本発明で用いられる試験昆虫としてのコナガの幼虫は、2001年4月韓国大田市儒城区魚隠洞所在の韓国生命工学研究院昆虫資源質から分譲され、実験昆虫として用いた。本発明のACAT阻害活性を有する化合物は、正確に重量を測定し、アセトンに適正量を溶かした後、triton X−100 100ppm水溶液9倍と混合し順次希釈して、処理すべき活性検索物質溶液を調製した。コナガ幼虫の餌としては、均一な発育状態のキャベツ葉のディスク(径3.0cm)を打ち抜き、用意された活性検索物質溶液に30秒間十分に浸る程度に浸漬してから取り出し、フード内で60分間乾燥した。蒸留水で濡らしたろ紙ディスクのシャーレ(55×20mm)に、活性検索物質が処理された葉を載せ、コナガの2齢幼虫を虫体が損なわないように柔らかなブラシで幼虫を移動させ、10匹ずつ3回繰り返して接種した。活性検索物質が処理されたコナガ幼虫は、恒温室(25±1℃、相対湿度40〜45%、16L:8D)で飼育し、24時間目、48時間目の殺虫率を調査した。無処理区は、処理された抽出物を除いたアセトン10%溶液にtriton X−100 100ppm水溶液9倍を処理して、活性検索物質の処理方法と同様にして処理した。活性検索実験は、3回繰り返して行い、Finney(1982)のプロビット法によって半数致死濃度(LC50)を算出した。
本発明で用いられるACAT阻害剤のうち、phenylpyropene A、B、C(化学式2〜4)により、幼虫の体重減少活性を実験した。試験昆虫としてのチャイロゴミムシダマシ幼虫は、韓国生命工学研究院昆虫資源質から分譲され、実験で用いた。チャイロゴミムシダマシの2齢幼虫(10〜12mm)を、活性評価実施の24時間前に健康な幼虫を選んで試験毎に用いた。化学式2〜4の化合物をそれぞれアセトン10%溶液を用いて、1mg/1mlの濃度で溶解させた後、順次希釈して、餌として用いるふすま1g当たり溶液1mlを入れて混合した。前記化合物が混合されたふすまをガラスシャーレ(90×20mm)に入れ、デシケーターに入れて約2時間減圧下で有機溶媒を除去させた後、活動性の良好な幼虫の体重を10匹単位で測定した後、ろ紙ディスクのシャーレ(87×15mm)に、適正量の活性検索物質を処理したふすまと一緒に入れた。室内温度25±1℃、相対湿度40〜45%、16時間明/8時間暗の条件で飼育しながら前記化合物を処理し、72時間の経過後、3日おきに幼虫の体重と摂食量を調査した。実験は3回繰り返して行い、無処理区はアセトン10%溶液を用いた。その結果を図8に示した。
以上のように、本発明は、アシルCoA:コレステロールアシルトランスフェラーゼの阻害活性を有する化合物またはその塩を有効成分とする殺虫剤に関するものであり、前記アシルCoA:コレステロールアシルトランスフェラーゼの阻害活性を有する化合物は、害虫の生体内でのステロール代謝を抑制して、幼虫の殺虫活性に優れ、かつ、安定性の高い殺虫剤として用いることができる。また、ペニシリウムグリセオフルビン F1959を用いて、アシルCoA:コレステロールアシルトランスフェラーゼの阻害活性を有する化合物を容易に得ることができる。
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KR20030000825A KR100522446B1 (ko) | 2003-01-07 | 2003-01-07 | 아실 코에이:콜레스테롤 아실 트란스퍼라제의 저해활성을갖는 화합물 또는 그 염을 유효성분으로 하는 살충제 |
PCT/KR2003/002711 WO2004060065A1 (en) | 2003-01-07 | 2003-12-11 | Insecticidal compositions comprising compounds having inhibitory activity versus acyl coa: cholesterol acyltransferase or salts thereof as effective ingredients |
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JP2006513233A JP2006513233A (ja) | 2006-04-20 |
JP4583934B2 true JP4583934B2 (ja) | 2010-11-17 |
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JP5037164B2 (ja) * | 2005-06-01 | 2012-09-26 | Meiji Seikaファルマ株式会社 | 害虫防除剤 |
US7491738B2 (en) | 2005-06-01 | 2009-02-17 | Meiji Seika Kaisha, Ltd. | Pest control agents |
TWI388282B (zh) | 2005-06-01 | 2013-03-11 | Meiji Seika Pharma Co Ltd | 害蟲控制劑 |
KR100943983B1 (ko) * | 2006-07-27 | 2010-02-26 | 한국생명공학연구원 | 피리피로펜 유도체 및 이를 포함하는 살충제 조성물 |
US8202890B2 (en) | 2006-11-30 | 2012-06-19 | Meiji Seika Pharma Co., Ltd. | Pest control agent |
KR101486094B1 (ko) * | 2007-03-08 | 2015-01-28 | 메이지 세이카 파루마 가부시키가이샤 | 유해생물 방제용 조성물 |
EP2186815A4 (en) | 2007-08-13 | 2012-01-25 | Meiji Seika Kaisha | PROCESS FOR PREPARING A PYRIPYROPEN DERIVATIVE AND INTERMEDIATE PRODUCT |
KR100928867B1 (ko) * | 2007-12-18 | 2009-11-30 | 한국생명공학연구원 | 복분자 추출물을 포함하는 살충제 |
AU2008342070B2 (en) | 2007-12-21 | 2014-07-31 | Meiji Seika Pharma Co., Ltd. | Novel systemic pesticide |
US8110608B2 (en) | 2008-06-05 | 2012-02-07 | Ecolab Usa Inc. | Solid form sodium lauryl sulfate (SLS) pesticide composition |
ES2453665T3 (es) * | 2008-07-24 | 2014-04-08 | Meiji Seika Pharma Co., Ltd. | Genes biosintéticos de piripiropeno A |
KR101067196B1 (ko) * | 2009-04-17 | 2011-09-22 | 고려대학교 산학협력단 | 포르핀계 화합물인 페어포비드 에이 메틸에스터 또는 감잎 추출물을 유효성분으로 함유하는 아실-코에이:콜레스테롤 아실트란스퍼라제의 활성 저해제 및 살충제용도 |
EP2426124B1 (en) | 2009-05-13 | 2013-08-07 | Meiji Seika Pharma Co., Ltd. | Process for producing pyripyropene derivative |
RU2012136447A (ru) | 2010-01-26 | 2014-03-10 | Мейдзи Сейка Фарма Ко., Лтд. | Способ получения пирипиропеновых производных ферментативным способом |
BR112012019456B8 (pt) | 2010-01-26 | 2022-08-02 | Mmag Co Ltd | Plasmídio compreendendo um ou mais polinucleotídeos e um promotor que é heterólogo para o um ou mais polinucleotídeos |
BR112012019458B8 (pt) | 2010-01-26 | 2022-08-02 | Mmag Co Ltd | construção de ácidos nucleicos, transformante, e métodos para produzir piripiropenos |
UA111151C2 (uk) | 2010-03-01 | 2016-04-11 | Мейдзі Сейка Фарма Ко., Лтд. | Спосіб одержання похідних пірипіропену |
CN103025161A (zh) * | 2010-05-24 | 2013-04-03 | 明治制果药业株式会社 | 有害生物防治剂 |
TWI584733B (zh) * | 2010-05-28 | 2017-06-01 | 巴地斯顏料化工廠 | 包含阿巴汀之農藥混合物、其用途及使用該混合物之方法 |
JP2013166704A (ja) * | 2010-06-16 | 2013-08-29 | Meiji Seikaファルマ株式会社 | 新規殺虫剤 |
CN103118537B (zh) | 2010-09-14 | 2015-08-12 | 巴斯夫欧洲公司 | 含有pyripyropene杀虫剂和碱的农药组合物 |
AU2011303970B2 (en) | 2010-09-14 | 2015-08-13 | Basf Se | Composition containing a pyripyropene insecticide and an adjuvant |
US8968757B2 (en) | 2010-10-12 | 2015-03-03 | Ecolab Usa Inc. | Highly wettable, water dispersible, granules including two pesticides |
US9596843B2 (en) | 2012-03-12 | 2017-03-21 | Basf Se | Liquid concentrate formulation containing a pyripyropene insecticide I |
MX360700B (es) | 2012-03-12 | 2018-11-14 | Basf Se | Formulacion concentrada liquida que contiene un insecticida de piripiropeno ii. |
KR102056608B1 (ko) | 2012-03-12 | 2019-12-17 | 바스프 에스이 | 피리피로펜 살곤충제의 수성 현탁액 농축물 제형의 제조 방법 |
CN105102625A (zh) | 2013-03-28 | 2015-11-25 | 巴斯夫欧洲公司 | 自干生物质制备啶南平 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5428818A (en) * | 1977-08-05 | 1979-03-03 | Fumakilla Ltd | Method of enhancing effect of pesticide smoked in short time |
AU654688B2 (en) * | 1990-10-30 | 1994-11-17 | Warner-Lambert Company | Oxysulfonyl carbamates |
US5484727A (en) * | 1992-10-14 | 1996-01-16 | Trustees Of Dartmouth College | Cloned gene encoding acylcoenzyme A: cholesterol acyltransferase (ACAT) |
JPH0948625A (ja) * | 1995-08-03 | 1997-02-18 | Koa Glass Kk | ガラス表面の研磨方法 |
US5968748A (en) * | 1998-03-26 | 1999-10-19 | Isis Pharmaceuticals, Inc. | Antisense oligonucleotide modulation of human HER-2 expression |
ES2260051T3 (es) * | 1999-09-14 | 2006-11-01 | Trustees Of Tufts College | Metodo para preparar tetraciclinas substituidas con quimicas basadas en metales de transicion. |
KR100436920B1 (ko) * | 2001-08-03 | 2004-06-22 | 한국생명공학연구원 | 인삼으로부터 추출한 신규한 폴리아세틸렌계 화합물, 그의추출방법 및 이를 함유하는 비만치료제 |
KR100399036B1 (ko) * | 2001-08-04 | 2003-09-22 | 한국생명공학연구원 | 신규한 페닐피로펜 씨, 이의 생산방법 및 이를 포함하는약학적 조성물 |
KR100443265B1 (ko) * | 2002-04-30 | 2004-08-04 | 한국생명공학연구원 | 신규 화합물 페닐피로펜 α와 페닐피로펜 β, 이의생산방법 및 이를 포함하는 약제 조성물 |
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- 2003-12-11 JP JP2004564582A patent/JP4583934B2/ja not_active Expired - Fee Related
- 2003-12-11 WO PCT/KR2003/002711 patent/WO2004060065A1/en active Application Filing
- 2003-12-11 BR BR0317269-4A patent/BR0317269A/pt not_active IP Right Cessation
- 2003-12-11 CA CA002512728A patent/CA2512728A1/en not_active Abandoned
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- 2003-12-11 CN CNA2003801095460A patent/CN1744817A/zh active Pending
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JP2006513233A (ja) | 2006-04-20 |
RU2305403C2 (ru) | 2007-09-10 |
EP1589816A4 (en) | 2006-06-28 |
KR100522446B1 (ko) | 2005-10-18 |
US20060135564A1 (en) | 2006-06-22 |
WO2004060065A1 (en) | 2004-07-22 |
AU2003303489A1 (en) | 2004-07-29 |
CN1744817A (zh) | 2006-03-08 |
AU2003303489B2 (en) | 2007-08-23 |
EP1589816A1 (en) | 2005-11-02 |
CA2512728A1 (en) | 2004-07-22 |
AU2003303489C1 (en) | 2009-09-03 |
RU2005125040A (ru) | 2006-01-20 |
KR20040063416A (ko) | 2004-07-14 |
US20090182014A1 (en) | 2009-07-16 |
BR0317269A (pt) | 2005-11-08 |
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