TWI827814B - 新穎化合物及其應用 - Google Patents
新穎化合物及其應用 Download PDFInfo
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- TWI827814B TWI827814B TW109108060A TW109108060A TWI827814B TW I827814 B TWI827814 B TW I827814B TW 109108060 A TW109108060 A TW 109108060A TW 109108060 A TW109108060 A TW 109108060A TW I827814 B TWI827814 B TW I827814B
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- 239000003860 topical agent Substances 0.000 description 1
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- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
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- 239000008170 walnut oil Substances 0.000 description 1
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Abstract
Description
本發明係關於一種新穎化合物及其應用。更具體而言,本發明係關於一種新穎化合物、包含該新穎化合物之組成物、包含該新穎化合物之化妝品組成物或抗氧化劑等。
由微生物所生產之代謝產物,大多對人類而言為有用的物質,傳統上被應用作醫藥、化妝品等之有效成分。
例如,從青黴菌分離出具有抗菌活性的青黴素等為知名的典故。此外,作為近年之事例,如專利文獻1及2所記載,已被報導從放線菌中獲得具有膜脂質障礙抑制作用、抗菌活性、抗氧化作用等之機能的崔杭傑林(Trehangelin)的物質。
如此從微生物獲得有用物質的例子不勝枚舉,使用微生物之新穎有用物質的探索,仍潛藏許多可能性。
【先前技術文獻】
【專利文獻】
【專利文獻1】國際公開第2014/034147號公報
【專利文獻2】日本公開專利公報「特開2015-24985號公報」
在此狀況下,本發明之一態樣之目的在於提供一種具有抗氧化作用之新穎化合物及其應用技術。
本發明之發明人,為了解決上述課題而反覆深入探討後,結果成功地從特定微生物中鑑定出具有抗氧化作用的新穎化合物,進一步具體而言,是從放線菌菌株Streptomyces lividans 1326中鑑定出,進而完成了本發明。亦即,本發明之一態樣係下述式(1)表示的化合物。
(式中,R1~R3中任1個為氫、乙醯基、2-丁烯醯基或2-甲基-2-戊烯
醯基,剩餘2個為氫,且R4~R6中任1個為2-甲基-2-丁烯醯基,剩餘2個為氫)。
根據本發明之一態樣,可提供一種具有抗氧化作用的新穎化合物。
【圖1】表示本發明之一態樣中化合物之抗氧化作用之評價結果的圖。
以下詳細說明本發明的實施型態之一。
又,本說明書中未特別記載下,表示數值範圍之「A~B」,係意味著「A以上,B以下」。此外,本說明書之結構式中未特別表示立體結構等時,本說明書之結構式所表示之化合物,係包含互變異構物、幾何異構物、光學異構物等之各種立體異構物,以及此等之混合物(包含消旋物)。
〔1.化合物〕
本發明之發明人,為了探索具有抗氧化作用的新穎化合物,對各種微生物進行了詳細的探討。其中,從已轉殖特定化合物之合成路徑相關基因的放線菌之鏈黴菌(Streptomyces lividans)菌株1326,成功鑑定出具有抗
氧化作用的新穎化合物。
本發明之一實施型態的化合物(以下,稱作「本化合物」),為上述式(1)所表示之化合物。本化合物,如後述實施例所示,具有優異的抗氧化作用。該化合物之具體例請見以下說明。又,本發明之化合物亦可為溶劑合物,例如水合物之型態,且此種溶劑合物亦包含於本化合物之範圍。此外,本說明書中,「2-丁烯醯基」係以與巴豆醯基及異巴豆醯基相同含義而使用,「2-甲基-2-丁烯醯基」係以與當歸醯基相同含義而使用。
本發明之一實施型態中,本化合物,較佳係上述式(1)中,R2為氫、乙醯基、2-丁烯醯基或2-甲基-2-戊烯醯基,R5為2-甲基-2-丁烯醯基,R1、R3、R4及R6為氫。
上述較佳態樣中,上述式(1)中的R2為「氫(H)」的化合物,為3-O-當歸醯基海藻糖(3-O-angeloyltrehalose),並由下述式(2)所表示。
本說明書中,3-O-當歸醯基海藻糖,為具有以下物理性質的化合物。
(1)性狀:白色粉末
(2)分子量:424
(3)分子式:C17H28O12
(4)熔點:117~120℃
(5)高解析質譜法之[M+NH4]+理論值(m/z):442.1925,實測數值(m/z):442.1901
(6)紫外線吸收最大值(甲醇中):220nm
(7)1H-NMRδ ppm:1.86(3H,dd,J1=1.5Hz,J2=1.5Hz),1.93(3H,dd,J1=7.2Hz,J2=1.5Hz),3.15(1H,ddd,J1=9.5Hz,J2=9.1Hz,J3=5.7Hz),3.2~3.7(9H,m),3.78(1H,ddd,J1=10.0Hz,J2=4.0Hz,J3=2.3Hz),4.37(1H,t,J=5.9Hz),4.48(1H,t,J=5.9Hz),4.72(1H,d,J=6.4Hz),4.77(1H,d,J=5.6Hz),4.84(1H,d,J=5.7Hz),4.84(1H,d,J=6.7Hz),4.91(1H,d,J=3.6Hz),4.95(1H,d,J=3.6Hz),5.02(1H,d,J=7.0Hz),5.21(1H,t,J=9.5Hz),6.04(1H,dq,J1=7.2Hz,J2=1.5Hz)
(8)對溶劑之溶解性:難溶於甲醇
上述較佳態樣中,上述式(1)中的R2為「乙醯基((CO)CH3)」的化合物,為3-O-乙醯基-3’-O-當歸醯基海藻糖(3-O-acetyl-3’-O-angeloyltrehalose),並由下述式(3)所表示。
本說明書中,3-O-乙醯基-3’-O-當歸醯基海藻糖,為具有以下物理性質的化合物。
(1)性狀:白色粉末
(2)分子量:466
(3)分子式:C19H30O13
(4)熔點:160~161℃
(5)高解析質譜法之[M+NH4]+理論值(m/z):484.2030,實測數值(m/z):484.2001
(6)紫外線吸收最大值(甲醇中):219nm
(7)1H-NMRδ ppm:1.87(3H,dd,J1=1.4Hz,J2=1.4Hz),1.93(3H,dd,J1=7.1Hz,J2=1.4Hz),2.05(3H,s),3.2~3.5(2H,m),3.4~3.7(6H,m),3.7~3.8(2H,m),4.45(1H,t,J=5.6Hz),4.48(1H,t,J=5.6Hz),4.94(1H,d,J=7.3Hz),4.95(1H,d,J=6.7Hz),4.97(2H,d,J=3.7Hz),5.02(1H,d,J=6.2Hz),5.03(1H,d,J=7.0Hz),5.14(1H,t,J=9.5Hz),5.24(1H,t,J=9.5Hz),6.05(1H,dq,J1=7.1Hz,J2=1.4Hz)
(8)對溶劑之溶解性:難溶於甲醇
上述較佳態樣中,上述式(1)中的R2為「異巴豆醯基((CO)HC=CHCH3)」的化合物,為3-O-當歸醯基-3’-O-異巴豆醯基海藻糖(3-O-angeloyl-3’-O-isocrotonyltrehalose),並由下述式(4)所表示。
本說明書中,3-O-當歸醯基-3’-O-異巴豆醯基海藻糖,為具有以下物理性質的化合物。
(1)性狀:白色粉末
(2)分子量:492
(3)分子式:C21H32O13
(4)熔點:155~158℃
(5)高解析質譜法之[M+NH4]+理論值(m/z):510.2187,實測數值(m/z):510.2225
(6)紫外線吸收最大值(甲醇中):227nm
(7)1H-NMRδ ppm:1.87(3H,dd,J1=1.4Hz,J2=1.4Hz),1.94(3H,dd,J1=7.1Hz,J2=1.4Hz),2.10(3H,dd,J1=7.2Hz,J2=1.7Hz),3.2~3.5(2H,m),
3.4~3.7(6H,m),3.7~3.8(2H,m),4.46(1H,t,J=5.9Hz),4.48(1H,t,J=5.9Hz),4.92(1H,d,J=7.2Hz),4.93(1H,d,J=7.2Hz),4.97(1H,d,J=3.1Hz),4.98(1H,d,J=3.1Hz),5.01(1H,d,J=7.3Hz),5.02(1H,d,J=7.4Hz),5.23(1H,t,J=9.5Hz),5.26(1H,t,J=9.5Hz),5.85(1H,dd,J1=11.5Hz,J2=1.7Hz),6.05(1H,dq,J1=7.1Hz,J2=1.4Hz),6.39(1H,dq,J1=11.5Hz,J2=7.2Hz)
(8)對溶劑之溶解性:難溶於甲醇
上述較佳態樣中,上述式(1)中的R2為「2-甲基-2-戊烯醯基((CO)C(CH3)=CHCH2CH3)」的化合物,為3-O-(2-甲基-2-丁烯醯基)-3’-O-(2-甲基-2-戊烯醯基)海藻糖(3-O-(2-methyl-2-butenoyl)-3’-O-(2-methyl-2-pentenoyl)trehalose),並由下述式(5)所表示。
本說明書中,3-O-(2-甲基-2-丁烯醯基)-3’-O-(2-甲基-2-戊烯醯基)海藻糖,具有由上述式(5)所表示之結構,並且具有以下物理性質的
化合物。
(1)性狀:白色粉末
(2)分子量:520
(3)分子式:C23H36O13
(4)熔點:176~180℃
(5)高解析質譜法之[M+NH4]+理論值(m/z):538.2500,實測數值(m/z):538.2495
(6)紫外線吸收最大值(甲醇中):227nm
(7)1H-NMRδ ppm:0.98(3H,t,J=7.5Hz),1.8~1.9(6H,m),1.94(3H,dd,J1=7.2Hz,J2=1.5Hz),2.41(2H,ddq,J1=7.5Hz,J2=7.5Hz,J3=1.1Hz),3.2~3.5(2H,m),3.4~3.7(6H,m),3.7~3.8(2H,m),4.48(2H,t,J=5.6Hz),4.917(1H,d,J=7.3Hz),4.925(1H,d,J=7.3Hz),4.98(2H,d,J=3.7Hz),5.01(2H,d,J=7.4Hz),5.26(1H,t,J=9.6Hz),5.27(1H,t,J=9.5Hz),5.93(1H,dt,J1=7.5Hz,J2=1.4Hz),6.05(1H,dq,J1=7.2Hz,J2=1.5Hz)
(8)對溶劑之溶解性:難溶於甲醇
〔2.組成物〕
本發明之一實施型態之組成物(以下,稱為「本組成物」),係含有上述式(1)~(5)所表示之本化合物中的至少一種。
此外,另一實施型態中,本組成物,較佳係進一步含有下述式(6)~(8)所表示之化合物中的至少一種。
上述式(6)~(8)所表示之化合物,分別被稱為「崔杭傑林A」、「崔杭傑林B」及「崔杭傑林C」。此外,本說明書中,將上述式(6)~(8)所表示之化合物統稱為「崔杭傑林」。
本組成物所含有之本化合物,由於具有抗氧化作用,因此
可應用於需要抗氧化物質的各種領域,例如化妝品、醫藥、食品、飲料品、香料、顏料、合成樹脂、接著劑、燃料等之領域。此外,上述式(6)~(8)所表示之化合物,由於具有膜脂質障礙抑制作用、抗菌活性、抗氧化作用等機能,因此藉由使本組成物含有此等化合物,可期待更廣泛的效能、與抗氧化作用之相乘效應等。
本組成物所含有之本化合物之配合量,例如可列舉約0.00001重量%~5重量%為較佳,但因應使用劑型、使用對象等各種條件,可適宜調整其配合量。其中,本組成物所含有之本化合物之配合量,較佳為0.00001重量%~0.5重量%,進一步較佳為0.0001重量%~0.05重量%。
此外,本組成物所含有之上述式(6)~(8)所表示之化合物的配合量,例如可列舉約0.0001重量%~10重量%為較佳,但因應使用劑型、使用對象等各種條件,可適宜調整其配合量。其中,本組成物所含有之上述化合物之配合量,較佳為0.0001重量%~1重量%,進一步較佳為0.001重量%~0.1重量%。
本組成物中,本發明之式(1)所表示之化合物與崔杭傑林之配合比,例如,可為0.01:1~10:1,較佳為0.4:1。
本組成物中,本發明之式(2)所表示之化合物與崔杭傑林之配合比,例如,可為0.01:1~10:1,較佳為0.2:1。
本組成物中,本發明之式(3)所表示之化合物與崔杭傑林之配合比,例如,可為0.01:1~10:1,較佳為0.04:1。
本組成物中,本發明之式(4)所表示之化合物與崔杭傑林之
配合比,例如,可為0.01;1~10:1,較佳為0.05:1。
本組成物中,本發明之式(5)所表示之化合物與崔杭傑林之配合比,例如,可為0.01:1~10:1,較佳為0.05:1。
本組成物中,本發明之式(2)~(5)所表示之化合物與崔杭傑林之配合比,例如,可為0.01:1~10:1,較佳為0.34:1。
本組成物,亦可含有崔杭傑林以外的各種物質。
以下,說明作為本組成物之一例的「化妝品組成物」及「抗氧化劑」。
〔3.化妝品組成物〕
本發明之一實施型態中,本組成物,理想為化妝品組成物(以下,稱作「本化妝品組成物」)。
本化妝品組成物,較佳係含有上述式(1)~(5)中至少任一種化合物,進一步較佳係更含有上述式(6)~(8)所表示化合物中的至少一種。
本化妝品組成物,除了上述化合物之外,亦可含有如植物油之油脂類、高級脂肪酸、高級醇、聚矽氧(silicone)、陰離子界面活性劑、陽離子界面活性劑、兩性界面活性劑、非離子界活性劑、防腐劑、醣類、螯合劑、如水溶性高分子之高分子、增稠劑、粉體成分、紫外線吸收劑、紫外線遮蔽劑、如玻尿酸之保濕劑、香料、pH調整劑、乾燥劑等。此外,本化妝品組成物,亦可含有維生素類、皮膚活化劑、血液循環促進劑、常駐菌控制劑、活性氧消除劑、抗發炎劑、抗癌劑、美白劑、殺菌劑等之其他藥效成分、生理活性成分等。
油脂類,例如,可列舉山茶油、月見草油、澳洲胡桃油、
橄欖油、菜籽油、玉米油、芝麻油、荷荷芭油、胚芽油、小麥胚芽油、三酸甘油酯、三辛酸甘油酯等之液體油脂;可可脂、椰子油、氫化椰子油、棕櫚油、棕櫚仁油、木蠟、木蠟核油、氫化油、氫化蓖麻油等之固體油脂;蜂蠟、堪地里拉蠟、棉蠟、糠蠟、羊毛脂、醋酸羊毛脂、液狀羊毛脂、甘蔗蠟等蠟類;流動石蠟;鯊烯;鯊烷;微晶蠟等。
高級脂肪酸,例如,可列舉月桂酸、肉荳蔻酸、棕櫚酸、硬酯酸、油酸、亞麻油酸、蘇子油酸、二十二碳六烯酸(DHA)、二十碳五烯酸(EPA)等。
高級醇,例如,可列舉月桂醇、硬脂醇、鯨蠟醇、鯨蠟硬脂醇等之直鏈醇;單硬脂甘油醚、羊毛脂醇、膽固醇、植物固醇、辛基十二醇等之支鏈醇等。
聚矽氧,例如,可列舉鏈狀聚矽氧烷之二甲基聚矽氧烷、甲基苯基聚矽氧烷等;環狀聚矽氧烷之十甲基聚矽氧烷等。
陰離子界面活性劑,例如,可列舉月桂酸鈉等之脂肪酸鹽、硫酸月桂酯鈉等之高級烷基硫酸酯鹽、POE月桂基硫酸三乙醇胺等之烷基醚硫酸酯鹽、N-醯基肌胺酸、磺琥珀酸鹽、N-醯基胺基酸鹽等。
陽離子界面活性劑,例如,可列舉硬脂基三甲基氯化銨等之烷基三甲基銨鹽、氯化苄烷銨、氯化苯索寧等。
兩性界面活性劑,例如,可列舉烷基甜菜鹼、醯胺基甜菜鹼等甜菜鹼系界面活性劑等。
非離子界面活性劑,例如,可列舉例如山梨糖醇酐單油酸酯等山梨糖醇酐脂肪酸酯類、氫化蓖麻油衍生物等。
防腐劑,例如,可列舉對羥苯甲酸甲酯、對羥苯甲酸乙酯等。
螯合劑,例如,可列舉乙二胺四乙酸、乙二胺四乙酸鈉鹽等。
高分子,例如,可列舉阿拉伯膠、黃蓍膠、聚半乳糖、瓜爾膠、鹿角菜膠、果膠、洋菜膠、榅桲籽、聚葡萄醣、聚三葡萄糖、羧甲基澱粉、膠原蛋白、酪蛋白、明膠、甲基纖維素、甲基羥丙基纖維素、羥乙基纖維素、羧甲基纖維素鈉(CMC)、藻酸鈉、羧乙烯聚合物(CARBOPOL等)等之乙烯系高分子、皂土等。
增稠劑,例如,可列舉鹿角菜膠、黃蓍膠、榅桲籽、酪蛋白、糊精、明膠、CMC、羥乙基纖維素、羥丙基纖維素、羧乙烯聚合物、瓜爾膠、三仙膠等。
粉末成分,例如,可列舉滑石、高嶺土、雲母、矽石、沸石、聚乙烯粉末、聚苯乙烯粉末、纖維素粉末、無機白色顏料、無機紅色系顏料、氧化鈦塗覆雲母、氧化鈦塗覆滑石、著色氧化鈦塗覆雲母等珠光顏料;紅色201號、紅色202號等有機顏料等。
紫外線吸收劑,例如,可列舉對胺苯甲酸、柳酸苯酯、對甲氧基肉桂酸異丙酯、對甲氧基肉桂酸辛酯、2,4-二羥二苯基酮等。
紫外線遮蔽劑,例如,可列舉氧化鈦、滑石、卡紅(carmine)、皂土、高嶺土、氧化鋅等。
保濕劑,例如,可列舉聚乙二醇、丙二醇、二丙烯甘醇、1,3-丁二醇、甘油、二甘油、聚甘油、木糖醇、麥芽糖醇、麥芽糖、山梨
醇、葡萄糖、果糖、軟骨素硫酸鈉、玻尿酸鈉、乳酸鈉、吡咯啶酮羧酸、環糊精等。
藥效成分,例如,可列舉下述維生素類:維生素A油、視黃醇等維生素A類;核黃素等維生素B2類;鹽酸吡多辛等維生素B6類;L-抗壞血酸、L-抗壞血酸磷酸酯、L-抗壞血酸單棕櫚酸酯、L-抗壞血酸二棕櫚酸酯、L-抗壞血酸-2-葡萄糖苷等維生素C類;泛酸鈣等泛酸類;維生素D2、膽鈣化固醇等維生素D類;α-生育酚、生育酚乙酸酯、菸鹼酸、DL-α-生育酚等維生素E類。
本化妝品組成物中可含有的物質,此外還可列舉胎盤素、麩胱甘肽、虎耳草萃取物等美白劑;蜂王漿、櫸萃取物等皮膚活化劑;辣椒素、薑酮、斑蝥酊劑、魚石脂、咖啡因、單寧酸、γ-米糠醇等血液循環促進劑;甘草酸(glycyrrhizinic acid)衍生物、甘草次酸(glycyrrhetinic acid)衍生物、甘菊藍等消炎劑;精胺酸、絲胺酸、白胺酸、色胺酸等胺基酸類;麥芽糖蔗糖縮合物等常駐菌控制劑;氯化溶菌酶等。
進一步地,本化妝品組成物中可含有的物質,可列舉洋甘菊萃取物、香芹萃取物、櫸萃取物、葡萄酒酵母、葡萄柚萃取物、忍冬萃取物、米萃取物、葡萄萃取物、啤酒花萃取物、米糠萃取物、枇杷萃取物、黃柏樹皮萃取物、薏苡仁萃取物、當藥萃取物、草木樨萃取物、樺萃取物、甘草萃取物、芍藥萃取物、肥皂草萃取物、絲瓜萃取物、辣椒萃取物、檸檬萃取物、龍膽萃取物、紫蘇萃取物、蘆薈萃取物、迷迭香萃取物、鼠尾草萃取物、百里香萃取物、茶萃取物、海藻萃取物、黃瓜萃取物、丁香萃取物、胡蘿蔔萃取物、歐洲七葉樹萃取物、金縷梅萃取物、桑
萃取物等各種萃取物。
本化妝品組成物,例如能以下述型態適用:水溶液、油劑、洗劑(lotion)、懸浮液等之液劑;凝膠、乳霜等之半固形劑;粉末、顆粒、膠囊、微膠囊、固體等之固體劑。可藉由傳統公知的方法調製為此等型態,使其為乳液劑、乳劑、凝膠劑、乳霜劑、軟膏、硬膏、泥敷劑、噴霧劑、栓劑、注射劑、粉末劑、顆粒劑、錠劑、丸劑、糖漿劑、喉錠劑等各種劑型。可藉由將此等塗佈、貼附、噴霧、飲用等施加至身體上而適用。此等劑型中,洗劑、乳劑、乳霜劑、軟膏劑、硬膏劑、泥敷劑(poultice)、噴霧劑等特別適用於皮膚外用劑。
本化妝品組成物,可為化妝水、乳液、乳霜、泥膜等之皮膚化妝品;如化妝基底乳、化妝乳霜、乳液狀或乳霜狀或軟膏型之粉底、口紅、眼彩、頰彩等之化妝品;護手霜、護腿霜、身體乳等之身體用化妝品;入浴劑、口腔化妝品、毛髮化妝品等。
〔4.抗氧化劑〕
本發明之一實施型態中,本組成物,較佳為抗氧化劑(以下,稱作「本抗氧化劑」)。
本抗氧化劑,可使用一般藥學上可接受之載體,並藉由常規方法製劑化。
調製為口服用固體製劑的情形下,可於主藥中添加賦形劑,並進一步因應需要添加結合劑、崩散劑、潤滑劑等後,藉由常規方法,製作為溶劑、顆粒劑、散劑、膠囊劑等。
調製為注射劑的情形下,可因應需要於主藥中添加pH調
整劑、緩衝劑、安定劑、助溶劑等,藉由常規方法,製作為皮下或靜脈內用注射劑。
調製為皮膚外用劑的情形下,可根據前述本化妝品組成物來調製。例如,可為軟膏劑,前述軟膏劑係由選自將上述式(1)~(5)所表示之本化合物溶解的脂肪酸酯類、高級醇類及碳酸丙烯酯所成群中的一種或兩種以上的混合物作為疏水性或無水性之溶劑,以及選自白色凡士林、黃色凡士林、流動石蠟及流動石蠟之聚乙烯凝膠中的一種或兩種以上的混合物作為親油性基劑而成。
此外,乳霜劑,可包含本化合物、油相成分、水相成分、2種以上的2.5~7.5重量份的界面活性劑,前述油相成分,可由5~20重量份的白色凡士林及5~15重量份的高級醇類組成之固體油份及由3~10重量份的鯊烷組成之液體油份組成。乳霜劑的油相成分中,除了上述白色凡士林、高級醇類、鯊烷以外,亦可添加其他固體油份、液體油份。
可在主藥中,因應需要,添加pH調整劑、緩衝劑、安定劑、助溶劑等,並藉由常規方法作成軟膏或乳霜等半固體劑、洗劑等液劑、或如貼布之外用劑。
本抗氧化劑,可全身性或局部性投予。
全身性投予之情形下,作為注射劑、口服劑、鼻用劑等,能以水性注射劑、油性注射劑、錠劑、顆粒劑、液劑、膠囊劑、軟膠囊劑、鼻用液劑、鼻用粉劑等劑型而投予至血管內、組織內、胃腸道、黏膜等。投予量,係因症狀程度、年齡、疾病之種類等而異,但一般成人係每1日分為1次~數次下每日投予50~500mg。
此外,局部性投予之情形下,作為外用劑,能以軟膏或乳霜等半固體劑、洗劑等液劑、或貼布劑型而直接投予至皮膚的疾病部位。投予量,係因症狀程度、年齡、疾病之種類等而異,但可根據一般抗發炎用之皮膚外用劑的適用方法。例如,可配合症狀將適量的外用劑1日塗佈1次~數次,亦可配合症狀多次塗佈。
〔5.本化合物之製造方法〕
本發明之一實施型態之本化合物之製造方法(以下,稱作「本製造方法」),係包含:(A)在培養基中培養具有生產上述式(1)~(5)所表示之本化合物之能力的微生物的步驟;及(B)從上述培養物中收集上述式(1)~(5)所表示之本化合物的步驟。
本化合物,可藉由在培養基中培養具有生產本化合物之能力的微生物,在培養物中蓄積本化合物,並且從該培養物中收集本化合物(分離、萃取、純化)而製造。
本製造方法中,「具有生產本化合物之能力的微生物」,只要是具有生產本化合物之能力的微生物,並無特別限定。此外,以此等之突變株為首,基因重組株、未被鑑定之未知的野生株等之所有具有生產本化合物之能力的菌,皆包含在可用於本製造方法的菌株。
微生物是否為「具有生產本化合物之能力的微生物」的判斷,可藉由在受驗對象之微生物可適度增殖的條件下(培養溫度、pH、培養基成分等)進行培養,並調查培養物中本化合物之有無來執行。上述培養物中,若存在本化合物,則可認定該微生物為具有生產本化合物之能力的微生物。又,上述受驗對象之微生物可適度增殖的條件,可因應培養的
微生物而做適當設定。
本說明書,「突變株」係指人工或自然界中藉由突變誘導刺激,從而具有與具有生產本化合物之能力之微生物不同的菌學性狀或基因的株,如此突變株,除了由具有生產本化合物之能力之微生物衍生的菌株外,亦包含衍生出具有生產本化合物之能力之微生物的原菌株。本說明書中,突變株不論是否具有實際衍生痕跡,例如,具有與具有生產本化合物之能力之微生物的基因(例如,16S rRNA基因)具高度相似性(例如,80%以上、85%以上、90%以上、95%以上等)之基因的菌株亦包含於突變株。此外,如此突變株,只要可維持本化合物之產能,則不論為人工製造者,或由自然收集者。
本說明書中,「基因重組株」係意指從外部人工地對微生物之野生株導入基因的株。基因重組株,只要具有生產本化合物之能力,則無特別限定。基因重組株亦稱為形質轉換體。
基因重組株之宿主,無特別限定,例如,可使用基因體上不具本化合物之合成基因的微生物。此情形下,可藉由在該微生物中導入本化合物之合成基因來製造本化合物。
此外,另一實施型態中,可使用基因體上具有本化合物之合成基因之微生物作為宿主。如此微生物,即使不導入基因,亦具有製造本化合物之能力,但在對如此微生物中導入本化合物之合成基因之情形下,則具有增加本化合物之製造量等優點。如此微生物,例如,可列舉紅多形孢菌(Polymorphospora rubra)K07-0510株(日本寄存編號NITE BP-01411)等。又,紅多形孢菌(Polymorphospora rubra)K07-0510株,如上
所述,由於能以其單體來製造本化合物,因此即使不導入基因之情形下,亦包含於「具有生產本化合物之能力的微生物」。
基因重組株之宿主,例如,可列舉屬於Escherichia屬、Corynebacterium屬、Brevibacterium屬、Bacillus屬、Microbacterium屬、Serratia屬、PSEudomonas屬、Agrobacterium屬、Alicyclobacillus屬、Anabaena屬、Anacystis屬、Arthrobacter屬、Azobacter屬、Chromatium屬、Erwinia屬、Methylobacterium屬、Phormidium屬、Rhodobacter屬、RhodopSEudomonas屬、Rhodospirillum屬、Scenedesmun屬、Streptomyces屬、Synnecoccus屬、Zymomonas屬的微生物等。較佳為,屬於Escherichia屬、Corynebacterium屬、Brevibacterium屬、Bacillus屬、PSEudomonas屬、Agrobacterium屬、Alicyclobacillus屬、Anabaena屬、Anacystis屬、Arthrobacter屬、Azobacter屬、Chromatium屬、Erwinia屬、Methylobacterium屬、Phormidium屬、Rhodobacter屬、RhodopSEudomonas屬、Rhodospirillum屬、Scenedesmun屬、Streptomyces屬、Synnecoccus屬、Zymomonas屬的微生物等。放線菌,例如,可列舉Streptomyces albus、Streptomyces lividans、Streptomyces chromofuscus、Streptomyces exfoliatus、Streptomyces argenteorus等。
基因重組株之宿主,只要是從外部人工地導入期望的基因時具有生產本化合物之能力者,則無特別限制,較佳為放線菌,進一步較佳為Streptomyces屬之放線菌,特別佳為Streptomyces lividans。
基因重組株的製作,例如,可藉由日本專利特開2017-158546號公報所記載之方法進行。簡潔來說,基於日本專利特開2017-
158546號公報的記載,取得編碼與崔杭傑林之合成相關酵素群(烯醯基輔酶A水合酶(enoyl-CoA hydratase)、3-酮醯基-輔酶A合成酶(3-ketoacyl-CoA synthase)、醯基轉移酶、3-酮醯基-輔酶A還原酶(3-ketoacyl-CoA reductase))的基因,並且基於同一文獻的記載,藉由將取得之基因組入載體中並導入宿主,從而獲得包含於「具有生產本化合物之能力的微生物」的基因重組株(形質轉換體)。
亦即,本發明的另一實施型態中,本化合物之製造方法,係包含:(C)在培養基中培養已導入編碼與崔杭傑林之合成相關酵素的基因的形質轉換體(例如,放線菌)的步驟;及(D)從上述培養物中收集上述式(1)~(5)所表示之本化合物的步驟。
本實施型態中,本化合物,可藉由在培養基中培養已組入與崔杭傑林之合成相關酵素群的形質轉換體(例如,放線菌),在培養物中蓄積本化合物,並且從該培養物中收集(分離、萃取、純化)本化合物而製造。
用於培養具有生產本化合物之能力之微生物的培養基,只要是可用作微生物之營養源的培養基即可。例如,可單獨或組合使用:市售的蛋白腖、肉萃、玉米浸液、棉籽粉、花生粉、大豆粉、酵母萃取物、NZ胺(NZ-amine)、酪蛋白的水合物、硝酸鈉、硝酸銨、硫酸銨等之氮源;甘油、澱粉、葡萄糖、半乳糖、甘露糖等之碳水化合物;或脂肪等之碳源;及食鹽、磷酸鹽、碳酸鈣、硫酸鎂等之無機鹽。除此之外,因應需要,亦可添加微量的金屬鹽、作為消泡劑之動物油、植物油、礦物油等。此等中只要是有助於利用生產菌來生產本化合物者皆可,可使用所有公知
的微生物的培養材料。
此外,具有生產本化合物之能力之微生物的培養,可藉由在能使生產菌發育並生產本化合物的溫度範圍下(例如10~40℃,較佳為25~30℃),振盪培養數日~2週而進行。培養條件,可參照本說明書之記載,因應所使用的本化合物之生產菌的性質,適宜選擇而進行。
本化合物之收集,可藉由使用乙酸乙酯等之水不互溶性的有機溶劑從培養液萃取而進行。除了本萃取法以外,亦可藉由適當組合或重複進行用於收集脂溶性物質之公知方法如吸收層析法、分配層析法、膠濾層析法、薄層層析法的抽取、離心逆流分配層析法、高速液相層析法等,以純化到純粹。
本化合物之收集,例如,可藉由實施例所記載之方法進行。
本發明之一實施型態,係包含以下構成。
<1>一種下述式(1)所表示之化合物。
(式中,R1~R3中任1個為氫、乙醯基、2-丁烯醯基或2-甲基-2-戊烯醯基,剩餘2個為氫,且R4~R6中任1個為2-甲基-2-丁烯醯基,剩餘2個為氫)。
<2>一種<1>所記載之化合物,其中,上述式(1)中,R2為氫、乙醯基、2-丁烯醯基或2-甲基-2-戊烯醯基,R5為2-甲基-2-丁烯醯基,R1、R3、R4及R6為氫。
<3>一種組成物,其係包含<1>或<2>所記載之化合物。
<4>一種<3>所記載之組成物,其中,進一步含有下述式(6)~(8)所表示之化合物中的至少一種。
<5>一種<3>或<4>所記載之組成物,其中,上述組成物為化妝品組成物或抗氧化劑。
<6>一種<1>或<2>所記載之化合物的製造方法,該方法係包含:
(A)在培養基中培養具有生產<1>或<2>所記載之化合物之能力的微生物的步驟;及
(B)從上述培養物中收集上述<1>或<2>所記載之化合物的步驟。
本發明並未限定於上述各實施型態,可在申請專利範圍中所示之範圍內進行各種變更,且分別將不同實施型態所開示的技術手段適當組合而得之實施型態亦包含於本發明之技術範圍。
【實施例】
以下藉由實施例進一步詳細說明本發明,惟本發明並非僅限定於該實施例。
〔1.生產菌株之製作〕
在含有1%酵母萃取物及1%葡萄糖之YD培養基中,將放線菌之Polymorphospora rubra K07-0510株在適當溫度(例如,27℃)下培養數日。培養後,藉由離心分離而從所得培養液中取得菌體。接著,根據常規方法(Molecular Cloning第二版),從所得菌體中分離純化染色體DNA。
方便起見,將SEQ ID NO:1之4個開讀框(orf),從鹼基序列編號小的開始,依序命名為orfA、orfB、orfC、orfD。orfA~D在SEQ ID NO:1中的位置與機能如下述。
orfA(SEQ ID NO:2,位於SEQ ID NO:1的鹼基編號1-828,編碼烯醯基輔酶A水合酶);
orfB(SEQ ID NO:3,位於SEQ ID NO:1的鹼基編號875-1900,編碼3-酮醯基-輔酶A合成酶);
orfC(SEQ ID NO:4,位於SEQ ID NO:1的鹼基編號1905-2684,編碼醯基轉移酶);
orfD(SEQ ID NO:5,位於SEQ ID NO:1的鹼基編號2681-3475,編碼3-酮醯基-輔酶A還原酶)。
使用PCR法〔Science,230,1350(1985)〕藉由下述方法構築能使上述4個基因充分表現的重組體質體。
以放線菌之Polymorphospora rubra K07-0510株的染色體DNA作為模板,藉由使用SEQ ID NO:6表示的5’末端具有PstI限制酶切位點及核糖體結合序列的正股引子、SEQ ID NO:7表示的5’末端具有StuI限制酶切位點的反股引子、及Taq DNA聚合酶(羅氏生命科學公司製),利用DNA熱循環器(應用生物系統公司製)進行PCR,從而增幅表現orfA、orfB、orfC及orfD(以下,稱為「orfABCD」)的DNA。PCR,係以95℃ 30秒、68℃ 30秒、72℃ 4分鐘的反應步驟為1個循環,進行30個循環後,在72℃進行反應10分鐘。藉由瓊脂糖凝膠電泳純化增幅的DNA片段,經限制酶PstI及StuI的切割,從而取得含有經PstI及StuI處理之表現orfABCD之DNA的DNA片段(以下,稱作「含orfABCD之DNA片段」)。
將pOSV556t(Nat.chem.,3,338,2011)以限制酶PstI及StuI切割,取得經PstI及StuI處理的pOSV556t片段。將上述所取得的經PstI及StuI處理的含orfABCD之DNA片段與經PstI及StuI處理的pOSV556t片段混合後,進行接合反應,藉此取得重組體DNA。
使用該重組體DNA,根據常規方法對E.coli Top10株形質
轉換後,將該形質轉換體塗佈於含100μg/ml之安比西林的LB瓊脂培養基,37℃下隔夜培養。根據規定方法從該形質轉換體中分離出含重組DNA之質體。藉由對DNA序列定序,確定該重組體DNA為orfABCD,將此質體命名為pOSV556-orfABCD。
藉由常規方法將pOSV556-orfABCD導入E.coli ET12567/pUZ8002株(Practical Streptomyces Genetics,2000),取得對50μg/ml之康黴素、25μg/ml之氯黴素及100μg/ml之安比西林表現抗性的E.coli ET12567/pUZ8002/pOSV556-orfABCD株。進一步,藉由常規方法使pOSV556-orfABCD從E.coli ET12567/pUZ8002株接合傳遞至放線菌之Streptomyces lividans 1326株(獨立行政法人製品評價技術基盤機構生物科技本部生物遺傳資源部門(NBRC):NBRC編號15675),從而獲得對50μg/ml之濕黴素表現抗性的Streptomyces lividans/pOSV556-orfABCD。
〔2.新穎化合物的分離及鑑定〕
將上述所得之Streptomyces lividans/pOSV556-orfABCD在含有1%酵母萃取物及1%葡萄糖的500ml液體培養基中,27℃下振盪培養1日。接著,添加50ml的20%海藻糖水溶液後,進一步在27℃下振盪培養4日。於所得培養液中加入500ml的乙醇且攪拌1小時。接著,減壓餾出此萃取液中的乙醇,於所得水溶液中加入250ml的乙酸乙酯且充分攪拌後,回收乙酸乙酯層。其後,濃縮乾燥,使之溶解在100ml的0.1%甲酸中。
使用源自上述所得500mL之培養液的濃縮乾燥樣本,進行新穎化合物之純化。純化中,係使用以下管柱及溶出溶劑。
<第1次的純化>
管柱:ULTRA PACK ODS-SM-50B φ26×300mm(山善公司製)
溶出溶劑:水/乙腈/甲酸(850/150/1)
<第2次的純化>
管柱:開放管柱(open column)中使用10g的Silica PSQ-100B
溶出溶劑:乙酸乙酯
純化途中分液的純度確認係以HPLC進行。回收LC純度95%以上的樣品,冷凍乾燥,純化。又,HPLC及LC/MS,係藉由以下的分析條件進行。
<HPLC分析條件>
裝置:Prominence UFLC系統(島津公司製)
管柱:YMC-Pack ODS-AQ(YMC股份公司製)
移動相:水/乙腈/甲酸(850/150/1)
流速:1毫升/分鐘
偵測:220nm
<LC/MS分析條件>
裝置:Agilent Technologies 6224 TOF LC/MS(Agilent Technologies公司製)
管柱:YMC-Pack ODS-AQ(YMC股份公司製)
移動相:水/乙腈/甲酸(850/150/1)
流速:0.5毫升/分鐘
藉此,獲得新穎化合物A(25mg)、新穎化合物B(12mg)、新穎化合物C(15mg)及新穎化合物D(20mg)。對此等化合物,進行以下熔點及
NMR分析。
(熔點及NMR分析結果)
對上述新穎化合物A、B、C及D,藉由以下分析條件,測定熔點及NMR。
<熔點測定條件>
裝置:BUCHI Melting Point B-545(BUCHI公司製)
<NMR分析條件>
裝置:BRUKER AMX 400(Bruker公司製)
溶劑:DMSO-d6
內標:TMS
其結果,新穎化合物A、B、C及D,分別被鑑定為3-O-當歸醯基海藻糖、3-O-乙醯基-3’-O-當歸醯基海藻糖、3-O-當歸醯基-3’-O-異巴豆醯基海藻糖及3-O-(2-甲基-2-丁烯醯基)-3’-O-(2-甲基-2-戊烯醯基)海藻糖。
〔3.生理機能評價〕
對上述所得化合物,進行生理機能的評價。生理機能的評價,係使用Carnosic acid,a catechol-type electrophilic compound,protects neurons both in vitro and in vivo through activation of the Keap1/Nrf2 pathway via S-alkylation of targeted cysteines on Keap1.Takumi Satoh et al.,Journal of Neurochemistry.Vol.104,pp.1116-1131,(2008)所記載的工具進行。
簡潔來說,使用10%FBS-DMEM/F12培養基(GIBCO公司製),將ARPE-19細胞播種於24孔盤上,以使其匯聚度達到50%。24
小時後,每一孔的用量下,調製(1)0.5μg的pGL3-GSTYaARE-Luciferase載體、0.5μg的pSV-betaGAL載體與50μL的Opti-MEM I(GIBCO公司製)的混合溶液(載體的溶液);及(2)2μL的lipofectamine 2000(賽默飛世爾科技公司製)與50μL的Opti-MEM I(GIBCO公司製)的混合溶液(lipofectamine 2000的溶液),並於室溫下靜置5分鐘。將該載體的溶液與該lipofectamine 2000的溶液混合,於室溫下靜置20分鐘。將此混合液(每1孔100μL)加入培養細胞(ARPE-19細胞)中,在CO2培養器中培養6小時。接著,將培養基交換為新的10%FBS-DMEM/F12培養基(0.5毫升/孔),培養18小時。其後,將培養基交換為新的10%FBS-DMEM/F12培養基(0.3毫升/孔)或含有20mg/mL的各種崔杭傑林衍生物的10%FBS-DMEM/F12培養基(0.3毫升/孔),培養24小時。去除培養基後,加入150μL的被動裂解緩衝液(Passive Lysis Buffer,Promega公司製),以調製細胞溶解液。
於96孔盤中逐孔加入100μL的細胞溶解液,加入100μL的βGAL分析套組溶液(Promega公司製),37℃下培養3小時。其後,藉由測定405nm的吸光度來確認βGAL活性。
在不同於上述之另一個96孔盤中逐孔加入20μL的細胞溶解液,並逐孔加入100μL的螢光素酶分析套組液(Promega公司製)。其後,藉由測定螢光來測定螢光素酶活性。藉由除以βGAL活性的結果來修正所得螢光素酶活性的結果,計算出抗氧化反應元件(antioxidant responsive element)轉錄活性。結果示於圖1。
(結果)
根據圖1,3-O-當歸醯基海藻糖、3-O-乙醯基-3’-O-當歸醯基海藻糖、3-O-當歸醯基-3’-O-異巴豆醯基海藻糖及3-O-(2-甲基-2-丁烯醯基)-3’-O-(2-甲基-2-戊烯醯基)海藻糖,與對照相比,均表現1.24~2.09倍的螢光素酶活性。據此,可知3-O-當歸醯基海藻糖、3-O-乙醯基-3’-O-當歸醯基海藻糖、3-O-當歸醯基-3’-O-異巴豆醯基海藻糖及3-O-(2-甲基-2-丁烯醯基)-3’-O-(2-甲基-2-戊烯醯基)海藻糖具有抗氧化作用。
此外,與公知物質的崔杭傑林A相比,可知3-O-當歸醯基海藻糖具有與崔杭傑林A相同程度的抗氧化作用,至於3-O-當歸醯基-3’-O-異巴豆醯基海藻糖及3-O-(2-甲基-2-丁烯醯基)-3’-O-(2-甲基-2-戊烯醯基)海藻糖具有比崔杭傑林A更高的抗氧化作用。
〔4.處方例〕
(化妝水)
作為包含本發明之一實施型態之化合物的化妝品,由下述組成來製造化妝水。室溫下,於下述成分(11)中加入成分(1)~(10)並攪拌。其後,加入成分(12)並均勻溶解,從而得到洗劑(單位為重量%)。
(1)甘油 9.5
(2)1,3-丁二醇 4.5
(3)葡萄糖 1.5
(4)乙醇 5.0
(5)羧乙烯聚合物 0.02
(6)甘草酸二鉀 0.1
(7)玻尿酸鈉 0.1
(8)本發明之一實施型態之化合物 0.1
(9)檸檬酸 0.05
(10)檸檬酸鈉 0.1
(11)離子交換水 剩餘組分
(12)氫氧化鉀 0.01
【產業利用性】
本發明係一種具有抗氧化作用之新穎化合物,其可應用於化妝品、醫藥等領域。
<110> 日商長瀨產業股份有限公司 學校法人北里研究所
<120> 新穎化合物及其應用
<130> NGS19461
<150> JP 2019-068164
<151> 2019-03-29
<160> 7
<170> PatentIn version 3.5
<210> 1
<211> 3475
<212> DNA
<213> Polymorphospora rubra
<400> 1
<210> 2
<211> 828
<212> DNA
<213> Polymorphospora rubra
<400> 2
<210> 3
<211> 1026
<212> DNA
<213> Polymorphospora rubra
<400> 3
<210> 4
<211> 780
<212> DNA
<213> Polymorphospora rubra
<400> 4
<210> 5
<211> 795
<212> DNA
<213> Polymorphospora rubra
<400> 5
<210> 6
<211> 37
<212> DNA
<213> 人工序列
<220>
<223> 引子
<400> 6
<210> 7
<211> 30
<212> DNA
<213> 人工序列
<220>
<223> 引子
<400> 7
Claims (8)
- 如申請專利範圍第1項所記載之化合物,其中,前述式(1)中,R2為氫、乙醯基、2-丁烯醯基或2-甲基-2-戊烯醯基;R5為2-甲基-2-丁烯醯基;R1、R3、R4及R6為氫。
- 一種組成物,其特徵係其包含申請專利範圍第1項所記載之化合物。
- 一種組成物,其特徵係其包含申請專利範圍第2項所記載之化合物。
- 如申請專利範圍第3至6項中任一項所記載之組成物,其中,前述組成物為化妝品組成物或抗氧化劑。
- 一種申請專利範圍第1或2項所記載之化合物的製造方法,其特徵係其包 含:(A)在培養基中培養具有生產申請專利範圍第1或2項所記載之化合物之能力的微生物的步驟,其中前述微生物係已導入編碼與崔杭傑林之合成相關酵素群的基因的形質轉換體,前述與崔杭傑林之合成相關酵素群包含烯醯基輔酶A水合酶(enoyl-CoA hydratase)、3-酮醯基-輔酶A合成酶(3-ketoacyl-CoA synthase)、醯基轉移酶及3-酮醯基-輔酶A還原酶(3-ketoacyl-CoA reductase);及(B)從上述培養物中收集申請專利範圍第1或2項所記載之化合物的步驟。
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US5049664A (en) * | 1988-08-26 | 1991-09-17 | Sawai Pharmaceutical Co., Ltd. | Trehalose derivatives |
JP3512147B2 (ja) * | 1997-09-25 | 2004-03-29 | ポーラ化成工業株式会社 | α,αグルコシルグルコシド含有石鹸 |
SE0401300D0 (sv) * | 2004-05-21 | 2004-05-21 | Forskarpatent I Syd Ab | Novel Galactoside Inhibitors of Galectins |
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Title |
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期刊 Inahashi Y, et al. Biosynthesis of Trehangelin in Polymorphospora rubra K07-0510: Identification of Metabolic Pathway to Angelyl-CoA. Chembiochem. 17(15):1442-7. Epub 2016/06/17. * |
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