JP6292671B2 - ミモシン誘導体並びにこれを含有する殺虫剤、抗線虫剤および日焼け防止剤 - Google Patents
ミモシン誘導体並びにこれを含有する殺虫剤、抗線虫剤および日焼け防止剤 Download PDFInfo
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- JP6292671B2 JP6292671B2 JP2014125504A JP2014125504A JP6292671B2 JP 6292671 B2 JP6292671 B2 JP 6292671B2 JP 2014125504 A JP2014125504 A JP 2014125504A JP 2014125504 A JP2014125504 A JP 2014125504A JP 6292671 B2 JP6292671 B2 JP 6292671B2
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- mimosine
- mimosinol
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- WZNJWVWKTVETCG-YFKPBYRVSA-N L-mimosine Chemical class OC(=O)[C@@H](N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-YFKPBYRVSA-N 0.000 title claims description 52
- 230000001679 anti-nematodal effect Effects 0.000 title claims description 20
- 239000002917 insecticide Substances 0.000 title claims description 14
- 239000000516 sunscreening agent Substances 0.000 title description 2
- 230000000475 sunscreen effect Effects 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 230000002087 whitening effect Effects 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 125000004431 deuterium atom Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 35
- WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 229950002289 mimosine Drugs 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 230000000694 effects Effects 0.000 description 19
- 230000002401 inhibitory effect Effects 0.000 description 18
- 102000012440 Acetylcholinesterase Human genes 0.000 description 17
- 108010022752 Acetylcholinesterase Proteins 0.000 description 17
- 241000244206 Nematoda Species 0.000 description 17
- 241000256602 Isoptera Species 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229940022698 acetylcholinesterase Drugs 0.000 description 15
- 102000003425 Tyrosinase Human genes 0.000 description 13
- 108060008724 Tyrosinase Proteins 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- -1 inhartase Proteins 0.000 description 11
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
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- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 4
- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 4
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- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 2
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Description
を示す ]
で表されるミモシン誘導体である。
トリス(トリエチルシリル)シラン、ロテノン、5,5−ジチオビス−(2−ニトロベンゾイック酸)、ヨウ化アセチルコリンおよび重水素化ホウ素ナトリウム(NaBD4)は、シグマ−アルドリッチ社から購入した。L−チロシン、水素化ホウ素ナトリウム(NaBH4)は和光純薬株式会社から購入した。
すべての統計的分析は、ウインドウズ用SASバージョン9.1.3を使用し、行われた。有意差分析は、データをワン−ウエイANOVAで分析し、ミーンは、p=0.01でのダンカン テストにより分離された。計算は、エクセル、マイクロソフトオフィス2003で行われた。IC50値は、50%阻害活性を与えるために各化合物において必要とされる濃度としててグラフィカルに決定した。
ギンネム(L. leucocephala)葉からのミモシンの単離
ギンネム葉サンプルは、26゜N、127゜Eに位置する琉球大学農学部の周囲から採取したものを使用した。ギンネムの新鮮な葉1.5kgを、10分間、5Lの熱水で処理した。
ミモシノール(1)および重水素化ミモシトール(2)の合成:
トリフルオロメチルスルホン酸(187μL、2mmol)のジクロロメタン(CH2Cl2)3.4mlを、25mL容の丸底フラスコに取り、これを室温で撹拌した。次いで、トリス(トリエチルシリル)シラン(618μL、2mmol)の溶液を滴加し、この混合物を溶液が透明になるまで3時間、室温で撹拌した。
1H−NMR(D2O,400MHz)δ:
8.16 (s, 1H, OH), 7.93 (s, 1H, CH), 7.28 (s, 1H, CH), 3.02-2.86 (d, 2H,
CH),2.72 (s, 2H, NH2), 2.68 (s, 1H, OH), 2.08-1.91 (s, 2H, CH2), 1.58-
1.54 (m, 2H, CH2), 1.22-1.11 (m, 1H, CH).
1H−NMR(D2O,400MHz)δ:
8.23 (s, 1H, OH), 7.93 (s, 1H, CH), 7.24 (s, 1H, CH), 3.02-2.86 (d, 2H,
CH), 2.72 (s, 2H, NH2), 2.68 (s, 1H, OH), 1.58-1.54 (m, 2H, CH2), 1.22-
1.11 (m, 1H, CH).
ミモシンのホスホアミドチオネート誘導体の調製:
(1)ミモシノール(1mmol)とトリエチルアミン(2mmol)を含むジオキサン溶液5mLを、氷浴で冷やした。これに、チオホスホリルクロライド(1mmol)を含むジオキサン5mLを滴下し、次いで、反応混合物を1時間撹拌した。
重水素化ミモシンのホスホアミドチオネート誘導体の調製:
D−ミモシノール(1mmol)とトリエチルアミン(2mmol)のジオキサン溶液10mLを、氷浴で冷やし、そして、チオホスホリルクロライド(1mmol)のジオキサン溶液10mLが滴下された。反応混合物は10分間、10℃以下の温度で撹拌された。
4(1H)−オン ]
黄色結晶
1H−NMR(D2O,400MHz)δ:
9.09 (s, 1H, OH), 8.69 (s, 1H, CH), 7.92 (s, 1H, CH), 7.47 (s, 1H, CH),
3.96-4.00 (m, 2H, CH2), 3.90-3.94 (m, 3H, CH3), 3.16-3.22 (m, 2H, CH2),
1.27 (s, 1H, NH).
2−オキサアザホスホリジン−4−イル)メチル)ヒドロキシピリジン−4
(1H)−オン ]
黄色結晶
1H−NMR(D2O,400MHz)δ:
9.09 (s, 1H, OH), 8.69 (s, 1H, CH), 7.92 (s, 1H, CH), 7.47 (s, 1H, CH),
3.98-4.02 (m, 2H, CH2), 3.95-3.98 (m, 3H, CH3), 3.62 (m, 2H, CH2), 3.18-
3.20 (m, 2H, CH2), 1.27 (s, 1H, NH).
スルフィド−1,3,2−オキサアザホスホリジン−4−イル)メチル)ピリジ
ン−4(1H)−オン ]
黄色結晶
1H−NMR(D2O,400MHz)δ:
9.09 (s, 1H, OH), 8.69 (s, 1H, CH), 7.92 (s, 1H, CH), 7.47 (s, 1H, CH),
3.98-4.00 (m, 2H, CH2), 3.95-3.98 (m, 3H, CH3), 3.62 (m, 2H, CH2), 3.18
-3.20 (m, 2H, CH2), 1.27 (s, 1H, NH), 0.94-0.89 (m, 2H, CH2).
2−スルフィド−1,3,2−オキサアザホスホリジン−4−イル)メチル)ピリ
ジン−4(1H)−オン ]
黄色結晶
1H−NMR(D2O,400MHz)δ:
9.09 (s, 1H, OH), 8.69 (s, 1H, CH), 7.92 (s, 1H, CH), 7.47 (s, 1H, CH),
3.90-3.94 (m, 3H, CH3), 3.16-3.22 (m, 2H, CH2), 1.27 (s, 1H, NH).
1,3,2−オキサアザホスホリジン−4−イル)メチル)ヒドロキシピリジン−
4(1H)−オン ]
黄色結晶
1H−NMR(D2O,400MHz)δ:
9.09 (s, 1H, OH), 8.69 (s, 1H, CH), 7.92 (s, 1H, CH), 7.47 (s, 1H, CH),
3.95-3.98 (m, 3H, CH3), 3.62 (m, 2H, CH2), 3.18-3.20 (m, 2H, CH2),
1.27 (s, 1H, NH).
−2−スルフィド−1,3,2−オキサアザホスホリジン−4−イル)メチル)ピ
リジン−4(1H)−オン ]
黄色結晶
1H−NMR(D2O,400MHz)δ:
9.09 (s, 1H, OH), 8.69 (s, 1H, CH), 7.92 (s, 1H, CH), 7.47 (s, 1H, CH),
3.95-3.98 (m, 3H, CH3), 3.62 (m, 2H, CH2), 3.18-3.20 (m, 2H, CH2),
1.27 (s, 1H, NH), 0.94-0.89 (m, 2H, CH2).
シロアリに対する外用アッセイ:
各実施例で得られた化合物の、急性毒性の生化学的アッセイは、これを働きシロアリへの外用投与によって実施した。各化合物をエタノールに溶解し、その少量(0.5μL)を、各シロアリ1匹に投与した場合、それぞれ0.25、0.5、1.5、2.5、7.5、12.5および25μgとなるよう7つの異なる投与溶液を調製した。コントロールとしては、エタノールのみのものを利用し、陽性コントロールとしては、フェニトロチオンとロテノンを使用した。
シロアリに対する非選択的アッセイ:
殺虫活性の評価のための非選択的バイオアッセイは、多和田らの手法(Tawata, S.ら、“Biosci., Biotechno., Biochem.”(1996), 60, 1643-1645.)にしたがっておこなわれた。試験化合物は、エタノールおよびアセトン中に3つの濃度(50、100、250ppm)となるように溶解し、ペトリ皿(直径8.5cm)に入れられたフィルターペーパーに適用した。また、コントロールとしては、エタノールおよびアセトンで処理されたフィルターペーパーを使用した。ロテノンとフェニトロチオンを陽性コントロールとして使用した。
C.エレガンスを用いる抗線虫活性アッセイ:
アッセイは、以前に説明された手順(Jang, S.-H.ら、“Biotechnology Letters.” (2004), 26, 287-291.およびSolis, G. M.ら、“ J. Visualized experiments.” (2011), 49, 1-6.)に若干の修正を加えて行った。線虫、カエノラブディテス・エレガンス(Caenorhabditis elegans)は、大腸菌OP50で覆われた、線虫培養培地(NGM)[3gのNaCl、15gの寒天、2.5gのポリペプトン、136.1gのKH2PO4、17.9g のKOH、1MのMgSO4の1mL、1MのCaCl2の1mL、コレステロールの1mL(5mg/mL)、アンピシリンの500μL(100μg/mL)]プレートで培養された。耐アンピシリンのOP50は、虫培養物の交差汚染を防ぐためのフィードソースとして使用した。
アセチルコリンエステラーゼ(AChE)阻害活性測定:
シロアリ全虫体(20mg)を0.1Mの燐酸塩バッファ(pH8.0)でホモゲナイズし、得られたホモジェネートを、12,000rpmで20分間遠心分離した。この上清をAChEの酵素源として使用した。酵素を調製するための全ての工程は、4℃で行われた。
Ao:コントロールの吸収
AE:試験サンプルの吸収
チロシナーゼ阻害活性分析:
チロシナーゼの阻害活性分析のためマイクロプレート試験は、文献記載の手順(Tadtong, S.ら“ J Health Res.”(2009), 23, 99-102.)に従って行われた。
CE:酵素を含むコントロールの吸収
Co:酵素を含まないコントロールの吸収
SE:酵素を含む試験サンプルの吸収
So:酵素を含まない試験サンプルの吸収
Claims (4)
- 次の式(I)
を示す ]
で表されるミモシン誘導体。 - 請求項1記載の式(I)で表されるミモシン誘導体を有効成分として含有する殺虫剤。
- 請求項1記載の式(I)で表されるミモシン誘導体を有効成分として含有する抗線虫剤。
- 請求項1記載の式(I)で表されるミモシン誘導体を有効成分として含有する美白剤。
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