CN113631562B - 新化合物及其应用 - Google Patents
新化合物及其应用 Download PDFInfo
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- CN113631562B CN113631562B CN202080025804.0A CN202080025804A CN113631562B CN 113631562 B CN113631562 B CN 113631562B CN 202080025804 A CN202080025804 A CN 202080025804A CN 113631562 B CN113631562 B CN 113631562B
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Abstract
本发明目的在于提供具有抗氧化作用的新化合物及其应用技术。提供由式(1)表示的化合物,解决上述课题。[式中,R1~R3中的任意一个为氢、乙酰基、2‑丁烯酰基或2‑甲基‑2‑戊烯酰基,其余2个为氢;且R4~R6中的任意一个为2‑甲基‑2‑丁烯酰基,其余2个为氢。]。
Description
技术领域
本发明涉及一种新化合物及其应用。更具体而言,本发明涉及一种新化合物、包含该新化合物的组合物、包含该新化合物的化妆品组合物或抗氧化剂等。
背景技术
由微生物所生产的代谢产物,对人类而言大多为有用的物质,传统上被应用作医药、化妆品等有效成分。
例如,从青霉菌分离出具有抗菌活性的青霉素等为知名的典故。此外,作为近年的事例,如专利文献1及2所记载,已被报导从放线菌中获得具有膜脂质障碍抑制作用、抗菌活性、抗氧化作用等功能的Trehangelin的物质。
这样从微生物获得有用物质的例子不胜枚举,使用微生物的新的有用物质的探索,仍潜藏许多可能性。
【现有技术文献】
【专利文献】
【专利文献1】国际公开第2014/034147号公报
【专利文献2】日本公开专利公报“特开2015-24985号公报”
发明内容
发明要解决的问题
在此情形下,本发明的一个实施方式的目的在于提供一种具有抗氧化作用的新化合物及其应用技术。
用于解决问题的手段
本发明的发明人,为了解决上述课题而反复深入探讨后,结果成功地从特定微生物中、具体而言从放线菌的变铅青链霉菌(Streptomyces lividans)菌株1326中鉴定出具有抗氧化作用的新化合物,进而完成了本发明。即,本发明的一个实施方式为下述式(1)表示的化合物。
[化1]
(式中,R1~R3中的任意一个为氢、乙酰基、2-丁烯酰基或2-甲基-2-戊烯酰基,其余2个为氢,且R4~R6中的任意一个为2-甲基-2-丁烯酰基,其余2个为氢)。
发明效果
根据本发明的一个实施方式,可提供一种具有抗氧化作用的新化合物。
附图说明
[图1]表示本发明的一个实施方式的化合物的抗氧化作用的评价结果的图。
具体实施方式
以下详细说明本发明的实施方式之一。
应予说明,本说明书中未特别记载下,表示数值范围的“A~B”,意味着“A以上且B以下”。此外,本说明书的结构式中未特别表示立体结构等时,本说明书中的结构式所表示的化合物,为包含互变异构体、几何异构体、光学异构体等各种立体异构体,以及它们的混合物(包含消旋物)。
〔1.化合物〕
本发明的发明人为了探索具有抗氧化作用的新化合物,对各种微生物进行了详细的探讨。其中,从已引入了特定化合物的合成路径相关基因的放线菌的变铅青链霉菌(Streptomyces lividans)菌株1326中成功鉴定出具有抗氧化作用的新化合物。
根据本发明的一个实施方式的化合物(以下,称作“本化合物”),为上述式(1)所表示的化合物。本化合物如后述实施例所示,具有优异的抗氧化作用。对于该化合物的具体例以下进行说明。应予说明,本发明的化合物可为溶剂合物,例如水合物的形态,且这样的溶剂合物也包含于本化合物的范围。此外,本说明书中,“2-丁烯酰基”以与巴豆酰基及异巴豆酰基相同含义而使用,“2-甲基-2-丁烯酰基”以与当归酰基相同含义而使用。
本发明的一个实施方式中,本化合物,优选为上述式(1)中,R2为氢、乙酰基、2-丁烯酰基或2-甲基-2-戊烯酰基,R5为2-甲基-2-丁烯酰基,R1、R3、R4及R6为氢。
上述优选实施方式中,上述式(1)中的R2为“氢(H)”的化合物,为3-O-当归酰基海藻糖(3-O-angeloyltrehalose),并由下述式(2)所表示。
[化2]
本说明书中,3-O-当归酰基海藻糖,为具有以下物理性质的化合物。
(1)性状:白色粉末
(2)分子量:424
(3)分子式:C17H28O12
(4)熔点:117~120℃
(5)高分辨率质谱法的[M+NH4]+理论值(m/z):442.1925,实测数值(m/z):442.1901
(6)紫外线吸收最大值(甲醇中):220nm
(7)1H-NMRδppm: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)对溶剂的溶解性:难溶于甲醇
上述优选实施方式中,上述式(1)中的R2为“乙酰基((CO)CH3)”的化合物为3-O-乙酰基-3’-O-当归酰基海藻糖(3-O-acetyl-3’-O-angeloyltrehalose),并由下述式(3)所表示。
[化3]
本说明书中,3-O-乙酰基-3’-O-当归酰基海藻糖为具有以下物理性质的化合物。
(1)性状:白色粉末
(2)分子量:466
(3)分子式:C19H30O13
(4)熔点:160~161℃
(5)高分辨率质谱法的[M+NH4]+理论值(m/z):484.2030,实测数值(m/z):484.2001
(6)紫外线吸收最大值(甲醇中):219nm
(7)1H-NMRδppm: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)对溶剂的溶解性:难溶于甲醇
上述优选实施方式中,上述式(1)中的R2为“异巴豆酰基((CO)HC=CHCH3)”的化合物为3-O-当归酰基-3’-O-异巴豆酰基海藻糖(3-O-angeloyl-3’-O-isocrotonyltrehalose),并由下述式(4)所表示。
[化4]
本说明书中,3-O-当归酰基-3’-O-异巴豆酰基海藻糖为具有以下物理性质的化合物。
(1)性状:白色粉末
(2)分子量:492
(3)分子式:C21H32O13
(4)熔点:155~158℃
(5)高分辨率质谱法的[M+NH4]+理论值(m/z):510.2187,实测数值(m/z):510.2225
(6)紫外线吸收最大值(甲醇中):227nm
(7)1H-NMRδppm: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)对溶剂的溶解性:难溶于甲醇
上述优选实施方式中,上述式(1)中的R2为“2-甲基-2-戊烯酰基((CO)C(CH3)=CHCH2CH3)”的化合物,为3-O-(2-甲基-2-丁烯酰基)-3’-O-(2-甲基-2-戊烯酰基)海藻糖(3-O-(2-methyl-2-butenoyl)-3’-O-(2-methyl-2-pentenoyl)trehalose),并由下述式(5)所表示。
[化5]
本说明书中,3-O-(2-甲基-2-丁烯酰基)-3’-O-(2-甲基-2-戊烯酰基)海藻糖,具有由上述式(5)所表示的结构,并且具有以下物理性质的化合物。
(1)性状:白色粉末
(2)分子量:520
(3)分子式:C23H36O13
(4)熔点:176~180℃
(5)高分辨率质谱法的[M+NH4]+理论值(m/z):538.2500,实测数值(m/z):538.2495
(6)紫外线吸收最大值(甲醇中):227nm
(7)1H-NMRδppm: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)对溶剂的溶解性:难溶于甲醇
〔2.组合物〕
本发明的一个实施方式的组合物(以下,称为“本组合物”),为含有上述式(1)~(5)所表示的本化合物中的至少一种。
此外,另一个实施方式中,本组合物优选为进一步含有下述式(6)~(8)所表示的化合物中的至少一种。
[化6]
[化7]
[化8]
上述式(6)~(8)所表示的化合物,分别被称为“Trehangelin A”、“TrehangelinB”及“Trehangelin C”。此外,本说明书中,将上述式(6)~(8)所表示的化合物统称为“Trehangelin”。
本组合物所含有的本化合物,由于具有抗氧化作用,因此可应用于需要抗氧化物质的各种领域,例如化妆品、医药、食品、饮料品、香料、颜料、合成树脂、粘接剂、燃料等领域。此外,上述式(6)~(8)所表示的化合物,由于具有膜脂质障碍抑制作用、抗菌活性、抗氧化作用等功能,因此通过使本组合物含有这些化合物,可期待更广泛的效能、与抗氧化作用的相乘效应等。
本组合物所含有的本化合物的配合量,例如可列举约0.00001重量%~5重量%为优选,但根据使用剂型、使用对象等各种条件,可适当调整其配合量。其中,本组合物所含有的本化合物的配合量,优选为0.00001重量%~0.5重量%,进一步优选为0.0001重量%~0.05重量%。
此外,本组合物所含有的上述式(6)~(8)所表示的化合物的配合量,例如可列举约0.0001重量%~10重量%为优选,但根据使用剂型、使用对象等各种条件,可适当调整其配合量。其中,本组合物所含有的上述化合物的配合量,优选为0.0001重量%~1重量%,进一步优选为0.001重量%~0.1重量%。
本组合物中,本发明的式(1)所表示的化合物与Trehangelin的配合比,例如,可为0.01:1~10:1,优选为0.4:1。
本组合物中,本发明的式(2)所表示的化合物与Trehangelin的配合比,例如,可为0.01:1~10:1,优选为0.2:1。
本组合物中,本发明的式(3)所表示的化合物与Trehangelin的配合比,例如,可为0.01:1~10:1,优选为0.04:1。
本组合物中,本发明的式(4)所表示的化合物与Trehangelin的配合比,例如,可为0.01;1~10:1,优选为0.05:1。
本组合物中,本发明的式(5)所表示的化合物与Trehangelin的配合比,例如,可为0.01:1~10:1,优选为0.05:1。
本组合物中,本发明的式(2)~(5)所表示的化合物与Trehangelin的配合比,例如,可为0.01:1~10:1,优选为0.34:1。
本组合物也可含有Trehangelin以外的各种物质。
以下,说明作为本组合物的一例的“化妆品组合物”及“抗氧化剂”。
〔3.化妆品组合物〕
本发明的一个实施方式中,本组合物优选为化妆品组合物(以下,称作“本化妆品组合物”)。
本化妆品组合物,优选为含有上述式(1)~(5)中至少任一种化合物,进一步优选为还含有上述式(6)~(8)所表示化合物中的至少一种。
除了上述化合物以外,本化妆品组合物也可含有如植物油的油脂类、高级脂肪酸、高级醇、有机硅(silicone)、阴离子型表面活性剂、阳离子型表面活性剂、两性表面活性剂、非离子型表面活性剂、防腐剂、醣类、金属离子封锁剂、如水溶性高分子的高分子、增稠剂、粉体成分、紫外线吸收剂、紫外线遮蔽剂、如玻尿酸的保湿剂、香料、pH调整剂、干燥剂等。此外,本化妆品组合物,也可含有维生素类、皮肤活化剂、血液循环促进剂、常驻菌控制剂、活性氧消除剂、抗发炎剂、抗癌剂、美白剂、杀菌剂等其他药效成分、生理活性成分等。
作为油脂类,例如,可列举山茶油、月见草油、澳洲胡桃油、橄榄油、菜籽油、玉米油、芝麻油、荷荷芭油、胚芽油、小麦胚芽油、三酸甘油酯、三辛酸甘油酯等液体油脂;可可脂、椰子油、氢化椰子油、棕榈油、棕榈仁油、木蜡、木蜡核油、氢化油、氢化蓖麻油等的固体油脂;蜂蜡、小烛树蜡、棉蜡、糠蜡、羊毛脂、醋酸羊毛脂、液状羊毛脂、甘蔗蜡等蜡类;液体石蜡;角鲨烯;角鲨烷;微晶蜡等。
作为高级脂肪酸,例如,可列举月桂酸、肉豆蔻酸、棕榈酸、硬酯酸、油酸、亚油酸、亚麻酸、二十二碳六烯酸(DHA)、二十碳五烯酸(EPA)等。
作为高级醇,例如,可列举月桂醇、硬脂醇、鲸蜡醇、鲸蜡硬脂醇等的直链醇;单硬脂甘油醚、羊毛脂醇、胆固醇、植物甾醇、辛基十二醇等支链醇等。
作为有机硅,例如,可列举链状聚硅氧烷的二甲基聚硅氧烷、甲基苯基聚硅氧烷等;环状聚硅氧烷的十甲基聚硅氧烷等。
作为阴离子型表面活性剂,例如,可列举月桂酸钠等脂肪酸盐、硫酸月桂酯钠等的高级烷基硫酸酯盐、POE月桂基硫酸三乙醇胺等烷基醚硫酸酯盐、N-酰基肌胺酸、磺琥珀酸盐、N-酰基胺基酸盐等。
作为阳离子型表面活性剂,例如,可列举硬脂基三甲基氯化铵等烷基三甲基铵盐、苯扎氯铵、苄索氯铵等。
作为两性表面活性剂,例如,可列举烷基甜菜碱、酰胺基甜菜碱等甜菜碱为表面活性剂等。
作为非离子型表面活性剂,例如,可列举例如山梨糖醇酐单油酸酯等山梨糖醇酐脂肪酸酯类、氢化蓖麻油衍生物等。
作为防腐剂,例如,可列举对羟苯甲酸甲酯、对羟苯甲酸乙酯等。
作为金属离子封锁剂,例如,可列举乙二胺四乙酸、乙二胺四乙酸钠盐等。
作为高分子,例如,可列举阿拉伯胶、黄蓍胶、聚半乳糖、瓜尔胶、鹿角菜胶、果胶、洋菜胶、榅桲籽、聚葡萄醣、三聚葡萄糖、羧甲基淀粉、胶原蛋白、酪蛋白、明胶、甲基纤维素、甲基羟丙基纤维素、羟乙基纤维素、羧甲基纤维素钠(CMC)、藻酸钠、羧基乙烯基聚合物(CARBOPOL等)等的乙烯系高分子、皂土等。
作为增稠剂,例如,可列举鹿角菜胶、黄蓍胶、榅桲籽、酪蛋白、糊精、明胶、CMC、羟乙基纤维素、羟丙基纤维素、羧基乙烯基聚合物、瓜尔胶、三仙胶等。
作为粉末成分,例如,可列举滑石、高岭土、云母、硅石、沸石、聚乙烯粉末、聚苯乙烯粉末、纤维素粉末、无机白色颜料、无机红色系颜料、氧化钛涂覆云母、氧化钛涂覆滑石、着色氧化钛涂覆云母等珠光颜料;红色201号、红色202号等有机颜料等。
作为紫外线吸收剂,例如,可列举对氨基苯甲酸、水杨酸苯基酯、对甲氧基肉桂酸异丙酯、对甲氧基肉桂酸辛酯、2,4-二羟二苯基酮等。
作为紫外线遮蔽剂,例如,可列举氧化钛、滑石、卡红(carmine)、皂土、高岭土、氧化锌等。
作为保湿剂,例如,可列举聚乙二醇、丙二醇、二丙二醇、1,3-丁二醇、甘油、二甘油、聚甘油、木糖醇、麦芽糖醇、麦芽糖、山梨醇、葡萄糖、果糖、软骨素硫酸钠、玻尿酸钠、乳酸钠、吡咯烷酮羧酸、环糊精等。
作为药效成分,例如,可列举下述维生素类:维生素A油、视黄醇等维生素A类;核黄素等维生素B2类;盐酸吡多辛等维生素B6类;L-抗坏血酸、L-抗坏血酸磷酸酯、L-抗坏血酸单棕榈酸酯、L-抗坏血酸二棕榈酸酯、L-抗坏血酸-2-葡萄糖苷等维生素C类;泛酸钙等泛酸类;维生素D2、胆钙化甾醇等维生素D类;α-生育酚、生育酚乙酸酯、烟碱酸、DL-α-生育酚等维生素E类。
本化妆品组合物中可含有的物质,此外还可列举胎盘素、麸胱甘肽、虎耳草萃取物等美白剂;蜂王浆、榉萃取物等皮肤活化剂;辣椒素、姜酮、斑蝥酊剂、鱼石脂、咖啡因、单宁酸、γ-米糠醇等血液循环促进剂;甘草酸(glycyrrhizinic acid)衍生物、甘草次酸(glycyrrhetinic acid)衍生物、甘菊蓝等消炎剂;精胺酸、丝胺酸、白胺酸、色胺酸等氨基酸类;麦芽糖蔗糖缩合物等常驻菌控制剂;氯化溶菌酶等。
进一步地,本化妆品组合物中可含有的物质,可列举洋甘菊萃取物、香芹萃取物、榉萃取物、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、黄柏树皮萃取物、薏苡仁萃取物、当药萃取物、草木樨萃取物、桦萃取物、甘草萃取物、芍药萃取物、肥皂草萃取物、丝瓜萃取物、辣椒萃取物、柠檬萃取物、龙胆萃取物、紫苏萃取物、芦荟萃取物、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、黄瓜萃取物、丁香萃取物、胡萝卜萃取物、欧洲七叶树萃取物、金缕梅萃取物、桑萃取物等各种萃取物。
本化妆品组合物,例如能以下述形态适用:水溶液、油剂、洗剂(lotion)、悬浮液等液剂;凝胶、乳霜等半固形剂;粉末、颗粒、胶囊、微胶囊、固体等固形剂。可通过传统公知的方法配制为这些形态,使其为乳液剂、乳剂、凝胶剂、乳霜剂、软膏、硬膏、泥敷剂、喷雾剂、栓剂、注射剂、粉末剂、颗粒剂、锭剂、丸剂、糖浆剂、喉锭剂等各种剂型。可通过将其涂布、贴附、喷雾、饮用等施加至身体上而适用。这些剂型中,洗剂、乳剂、乳霜剂、软膏剂、硬膏剂、泥敷剂(poultice)、喷雾剂等特别适用于皮肤外用剂。
本化妆品组合物可为化妆水、乳液、乳霜、泥膜等的皮肤化妆品;如化妆基底乳、化妆乳霜、乳液状或乳霜状或软膏型的粉底、口红、眼彩、颊彩等化妆品;护手霜、护腿霜、身体乳等身体用化妆品;入浴剂、口腔化妆品、毛发化妆品等。
〔4.抗氧化剂〕
本发明的一个实施方式中,本组合物优选为抗氧化剂(以下,称作“本抗氧化剂”)。
本抗氧化剂,可使用一般药学上可接受的载体,并通过常规方法制剂化。
配制为口服用固形制剂的情形下,可于主药中添加赋形剂,并进一步根据需要添加结合剂、崩散剂、润滑剂等后,通过常规方法,制作为溶剂、颗粒剂、散剂、胶囊剂等。
配制为注射剂的情形下,可应需要于主药中添加pH调整剂、缓冲剂、稳定剂、助溶剂等,通过常规方法,制作为皮下或静脉内用注射剂。
配制为皮肤外用剂的情形下,可根据前述本化妆品组合物来配制。例如,可为软膏剂,前述软膏剂为由选自将上述式(1)~(5)所表示的本化合物溶解的脂肪酸酯类、高级醇类及碳酸丙烯酯中的一种或两种以上的混合物作为疏水性或无水性的溶剂,以及选自白色凡士林、黄色凡士林、液体石蜡及液体石蜡的聚乙烯凝胶中的一种或两种以上的混合物作为亲油性基料而成。
此外,作为乳霜剂,可形成包含本化合物、油相成分、水相成分、2种以上的2.5~7.5重量份的表面活性剂的乳霜剂,前述油相成分由5~20重量份的白色凡士林及5~15重量份的高级醇类组成的固体油分及由3~10重量份的角鲨烷组成的液体油分组成。乳霜剂的油相成分中,除了上述白色凡士林、高级醇类、角鲨烷以外,也可添加其他固体油分、液体油分。
可在主药中,应需要,添加pH调整剂、缓冲剂、稳定剂、助溶剂等,并通过常规方法作成软膏或乳霜等半固形剂、洗剂等液剂、或如贴布的外用剂。
本抗氧化剂,可全身性或局部性施用。
全身性施用的情形下,作为注射剂、口服剂、鼻用剂等,能以水性注射剂、油性注射剂、锭剂、颗粒剂、液剂、胶囊剂、软胶囊剂、鼻用液剂、鼻用粉剂等剂型而施用至血管内、组织内、胃肠道、粘膜等。施用量,因症状程度、年龄、疾病的种类等而异,但一般成人每1日分为1次~数次下每日施用50~500mg。
此外,局部性施用的情形下,作为外用剂,能以软膏或乳霜等半固形剂、洗剂等液剂、或贴布剂型而直接施用至皮肤的疾病部位。施用量,因症状程度、年龄、疾病的种类等而异,但可根据一般抗发炎用的皮肤外用剂的适用方法。例如,可配合症状将适量的外用剂1日涂布1次~数次,也可配合症状多次涂布。
〔5.本化合物的制造方法〕
本发明的一个实施方式的本化合物的制造方法(以下,称作“本制造方法”),包含:(A)在培养基中培养具有生产上述式(1)~(5)所表示的本化合物的能力的微生物的步骤;及(B)从上述培养物中收集上述式(1)~(5)所表示的本化合物的步骤。
本化合物,可通过在培养基中培养具有生产本化合物的能力的微生物,在培养物中积累本化合物,并且从该培养物中收集本化合物(分离、萃取、纯化)而制造。
本制造方法中,“具有生产本化合物的能力的微生物”,只要是具有生产本化合物的能力的微生物,并无特别限定。此外,以它们的突变株为首,基因重组株、未被鉴定的未知的野生株等所有具有生产本化合物的能力的菌,均包括在可用于本制造方法的菌株。
微生物是否为“具有生产本化合物的能力的微生物”的判断,可通过在受验对象的微生物可适度增殖的条件下(培养温度、pH、培养基成分等)进行培养,并调查培养物中本化合物的有无来执行。上述培养物中,若存在本化合物,则可认定该微生物为具有生产本化合物的能力的微生物。应予说明,上述受验对象的微生物可适度增殖的条件,可根据培养的微生物而做适当设定。
本说明书中,“突变株”指人工或自然界中通过突变诱导刺激,从而具有与具有生产本化合物的能力的微生物不同的菌学性状或基因的株,这样的突变株,除了由具有生产本化合物的能力的微生物衍生的菌株外,也包含衍生出具有生产本化合物的能力的微生物的原菌株。本说明书中,突变株不论是否具有实际衍生痕迹,例如,具有与具有生产本化合物的能力的微生物的基因(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)的基因的菌株也包含于突变株。此外,这样的突变株,只要可维持本化合物的产生能力,则不论为人工制造还是自然收集。
本说明书中,“基因重组株”意指从外部人工地对微生物的野生株导入基因的株。基因重组株,只要具有生产本化合物的能力,则无特别限定。基因重组株也称为基因重组体。
基因重组株的宿主,无特别限定,例如,可使用基因体上不具本化合物的合成基因的微生物。此情形下,可通过在该微生物中导入本化合物的合成基因来制造本化合物。
此外,另一个实施方式中,可使用基因体上具有本化合物的合成基因的微生物作为宿主。这样的微生物,即使不导入基因,也具有制造本化合物的能力,但在对如此微生物中导入本化合物的合成基因的情形下,则具有增加本化合物的制造量等优点。这样的微生物,例如,可列举红多形孢菌(Polymorphospora rubra)K07-0510株(日本寄存编号NITEBP-01411)等。应予说明,红多形孢菌(Polymorphospora rubra)K07-0510株,如上所述,由于能以其单体来制造本化合物,因此即使不导入基因的情形下,也包含于“具有生产本化合物的能力的微生物”。
基因重组株的宿主,例如,可列举属于埃希氏菌属(Escherichia属)、棒状杆菌属(Corynebacterium属)、短杆菌属(Brevibacterium属)、芽孢杆菌属(Bacillus属)、微杆菌属(Microbacterium属)、沙雷氏菌属(Serratia属)、假单胞菌属(PSEudomonas属)、土壤杆菌属(Agrobacterium属)、脂环酸芽孢杆菌属(Alicyclobacillus属)、鱼腥藻属(Anabaena属)、组囊蓝细菌属(Anacystis属)、节杆菌属(Arthrobacter属)、固氮菌属(Azobacter属)、着色菌属(Chromatium属)、欧文氏菌属(Erwinia属)、甲基杆菌属(Methylobacterium属)、席藻属(Phormidium属)、红杆菌属(Rhodobacter属)、红假单胞菌属(RhodopSEudomonas属)、红螺菌属(Rhodospirillum属)、栅藻属(Scenedesmun属)、链霉菌属(Streptomyces属)、Synnecoccus属、发酵单胞菌属(Zymomonas属)的微生物等。优选为,属于埃希氏菌属(Escherichia属)、棒状杆菌属(Corynebacterium属)、短杆菌属(Brevibacterium属)、芽孢杆菌属(Bacillus属)、假单胞菌属(PSEudomonas属)、土壤杆菌属(Agrobacterium属)、脂环酸芽孢杆菌属(Alicyclobacillus属)、鱼腥藻属(Anabaena属)、组囊蓝细菌属(Anacystis属)、节杆菌属(Arthrobacter属)、固氮菌属(Azobacter属)、着色菌属(Chromatium属)、欧文氏菌属(Erwinia属)、甲基杆菌属(Methylobacterium属)、席藻属(Phormidium属)、红杆菌属(Rhodobacter属)、红假单胞菌属(RhodopSEudomonas属)、红螺菌属(Rhodospirillum属)、栅藻属(Scenedesmun属)、链霉菌属(Streptomyces属)、Synnecoccus属、发酵单胞菌属(Zymomonas属)的微生物等。放线菌,例如,可列举白色链霉菌(Streptomyces albus)、变铅青链霉菌(Streptomyces lividans)、色褐链霉菌(Streptomyces chromofuscus)、脱叶链霉菌(Streptomyces exfoliatus)、银链霉菌(Streptomyces argenteorus)等。
基因重组株的宿主,只要是从外部人工地导入期望的基因时具有生产本化合物的能力者,则无特别限制,优选为放线菌,进一步优选为链霉菌属(Streptomyces属)的放线菌,特别佳为变铅青链霉菌(Streptomyces lividans)。
基因重组株的制作,例如,可通过日本专利特开2017-158546号公报所记载的方法进行。简单而言,基于日本专利特开2017-158546号公报的记载,取得编码与Trehangelin的合成相关酵素群(烯酰基辅酶A水合酶(enoyl-CoA hydratase)、3-酮酰基-辅酶A合成酶(3-ketoacyl-CoA synthase)、酰基转移酶和3-酮酰基-辅酶A还原酶(3-ketoacyl-CoAreductase))的基因,并且基于该文献的记载,通过将取得的基因组入载体中并导入宿主,从而获得包含于“具有生产本化合物的能力的微生物”的基因重组株(基因重组体)。
即,本发明的另一个实施方式中,本化合物的制造方法,包含:(C)在培养基中培养已导入编码与Trehangelin的合成相关酵素的基因的基因重组体(例如,放线菌)的步骤;及(D)从上述培养物中收集上述式(1)~(5)所表示的本化合物的步骤。
本实施方式中,本化合物,可通过在培养基中培养已组入与Trehangelin的合成相关酵素群的基因重组体(例如,放线菌),在培养物中积累本化合物,并且从该培养物中收集(分离、萃取、纯化)本化合物而制造。
用于培养具有生产本化合物的能力的微生物的培养基,只要是可用作微生物的营养源的培养基即可。例如,可单独或组合使用市售的蛋白胨、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、硝酸钠、硝酸铵、硫酸铵等氮源;甘油、淀粉、葡萄糖、半乳糖、甘露糖等碳水化合物;或脂肪等碳源;及氯化钠、磷酸盐、碳酸钙、硫酸镁等无机盐。除此以外,根据需要,也可添加微量的金属盐、作为消泡剂的动物油、植物油、矿物油等。它们中只要是有助于利用生产菌来生产本化合物者皆可,可使用所有公知的微生物的培养材料。
此外,具有生产本化合物的能力的微生物的培养,可通过在能使生产菌发育并生产本化合物的温度范围下(例如10~40℃,优选为25~30℃),振荡培养数日~2周而进行。培养条件,可参照本说明书的记载,根据所使用的本化合物的生产菌的性质,适当选择而进行。
本化合物的收集,可通过使用乙酸乙酯等的水不互溶性的有机溶剂从培养液萃取而进行。除了本萃取法以外,也可通过适当组合或重复进行用于收集脂溶性物质的公知方法如吸收层析法、分配层析法、胶滤层析法、薄层层析法的抽取、离心逆流分配层析法、高速液相层析法等,以纯化到纯粹。
本化合物的收集例如可通过实施例所记载的方法进行。
本发明的一个实施方式,包括以下构成。
<1>一种下述式(1)所表示的化合物。
[化9]
(式中,R1~R3中的任意一个为氢、乙酰基、2-丁烯酰基或2-甲基-2-戊烯酰基,其余2个为氢,且R4~R6中的任意一个为2-甲基-2-丁烯酰基,其余2个为氢)。
<2>一种<1>所记载的化合物,其中,上述式(1)中,R2为氢、乙酰基、2-丁烯酰基或2-甲基-2-戊烯酰基,R5为2-甲基-2-丁烯酰基,R1、R3、R4及R6为氢。
<3>一种组合物,其为包含<1>或<2>所记载的化合物。
<4>一种<3>所记载的组合物,其中,进一步含有下述式(6)~(8)所表示的化合物中的至少一种。
[化10]
[化11]
[化12]
<5>一种<3>或<4>所记载的组合物,其中,上述组合物为化妆品组合物或抗氧化剂。
<6>一种<1>或<2>所记载的化合物的制造方法,该方法包含:
(A)在培养基中培养具有生产<1>或<2>所记载的化合物的能力的微生物的步骤;及
(B)从上述培养物中收集上述<1>或<2>所记载的化合物的步骤。
本发明并未限定于上述各实施方式,可在权利要求范围中所示的范围内进行各种变更,且分别将不同实施方式所开示的技术手段适当组合而得的实施方式也包括于本发明的技术范围。
【实施例】
以下通过实施例进一步详细说明本发明,但本发明并非仅限定于所述实施例。
〔1.生产菌株的制作〕
在含有1%酵母萃取物及1%葡萄糖的YD培养基中,将放线菌的Polymorphosporarubra K07-0510株在适当温度(例如,27℃)下培养数日。培养后,通过离心分离而从所得培养液中取得菌体。接着,根据常规方法(Molecular Cloning第二版),从所得菌体中分离纯化染色体DNA。
方便起见,将序列号:1的4个开读框(orf),从碱基序列编号小的开始,依序命名为orfA、orfB、orfC、orfD、orfA~D在序列号:1中的位置与功能为如下。
orfA(序列号:2,位于序列号:1的碱基编号1-828,编码烯酰基辅酶A水合酶);
orfB(序列号:3,位于序列号:1的碱基编号875-1900,编码3-酮酰基-辅酶A合成酶);
orfC(序列号:4,位于序列号:1的碱基编号1905-2684,编码酰基转移酶);
orfD(序列号:5,位于序列号:1的碱基编号2681-3475,编码3-酮酰基-辅酶A还原酶)。
使用PCR法〔Science,230,1350(1985)〕通过下述方法构筑能使上述4个基因充分表现的重组体质体。
以放线菌的Polymorphospora rubra K07-0510株的染色体DNA作为模板,通过使用序列号:6表示的5’末端具有PstI限制酶切位点及核糖体结合序列的正义链引物、序列号:7表示的5’末端具有StuI限制酶切位点的反义链引物、及Taq DNA聚合酶(罗氏生命科学公司制),利用DNA热循环器(应用生物系统公司制)进行PCR,从而增幅表现orfA、orfB、orfC及orfD(以下,称为“orfABCD”)的DNA。PCR为以95℃30秒、68℃30秒、72℃4分钟的反应步骤为1个循环,进行30个循环后,在72℃进行反应10分钟。通过琼脂糖凝胶电泳纯化增幅的DNA片段,经限制酶PstI及StuI的切割,从而取得含有经PstI及StuI处理的表现orfABCD的DNA的DNA片段(以下,称作“含orfABCD的DNA片段”)。
将pOSV556t(Nat.chem.,3,338,2011)以限制酶PstI及StuI切割,取得经PstI及StuI处理的pOSV556t片段。将上述所取得的经PstI及StuI处理的含orfABCD的DNA片段与经PstI及StuI处理的pOSV556t片段混合后,进行接合反应,由此取得重组体DNA。
使用该重组体DNA,根据常规方法对E.coli Top10株形质转换后,将该基因重组体涂布于含100μg/ml的安比西林的LB琼脂培养基,37℃下隔夜培养。根据规定方法从该基因重组体中分离出含重组DNA的质体。通过对DNA序列定序,确定该重组体DNA为orfABCD,将此质体命名为pOSV556-orfABCD。
通过常规方法将pOSV556-orfABCD导入E.coli ET12567/pUZ8002株(PracticalStreptomyces Genetics,2000),取得对50μg/ml的康霉素、25μg/ml的氯霉素及100μg/ml的安比西林表现抗性的E.coli ET12567/pUZ8002/pOSV556-orfABCD株。进一步,通过常规方法使pOSV556-orfABCD从E.coli ET12567/pUZ8002株接合传递至放线菌的变铅青链霉菌(Streptomyces lividans)1326株(独立行政法人制品评价技术基盘机构生物科技本部生物遗传资源部门(NBRC):NBRC编号15675),从而获得对50μg/ml的湿霉素表现抗性的变铅青链霉菌(Streptomyces lividans)/pOSV556-orfABCD。
〔2.新化合物的分离及鉴定〕
将上述所得的变铅青链霉菌(Streptomyces lividans)/pOSV556-orfABCD在含有1%酵母萃取物及1%葡萄糖的500ml液体培养基中,27℃下振荡培养1日。接着,添加50ml的20%海藻糖水溶液后,进一步在27℃下振荡培养4日。于所得培养液中加入500ml的乙醇且搅拌1小时。接着,减压馏出此萃取液中的乙醇,于所得水溶液中加入250ml的乙酸乙酯且充分搅拌后,回收乙酸乙酯层。其后,浓缩干燥,使其溶解在100ml的0.1%甲酸中。
使用源自上述所得500mL的培养液的浓缩干燥样本,进行新化合物的纯化。纯化中,使用以下管柱及溶出溶剂。
<第1次的纯化>
管柱:ULTRA PACK ODS-SM-50B(山善公司制)
溶出溶剂:水/乙腈/甲酸(850/150/1)
<第2次的纯化>
管柱:开放管柱(open column)中使用10g的Silica PSQ-100B
溶出溶剂:乙酸乙酯
纯化途中分液的纯度确认以HPLC进行。回收LC纯度95%以上的样品,冷冻干燥,纯化。应予说明,HPLC及LC/MS,由以下的分析条件进行。
<HPLC分析条件>
装置:Prominence UFLC系统(岛津公司制)
管柱:YMC-Pack ODS-AQ(YMC股份公司制)
移动相:水/乙腈/甲酸(850/150/1)
流速:1毫升/分钟
侦测:220nm
<LC/MS分析条件>
装置:Agilent Technologies 6224TOF LC/MS(Agilent Technologies公司制)
管柱:YMC-Pack ODS-AQ(YMC股份公司制)
移动相:水/乙腈/甲酸(850/150/1)
流速:0.5毫升/分钟
由此,获得新化合物A(25mg)、新化合物B(12mg)、新化合物C(15mg)及新化合物D(20mg)。对这些化合物,进行以下熔点及NMR分析。
(熔点及NMR分析结果)
对上述新化合物A、B、C及D,通过以下分析条件,测定熔点及NMR。
<熔点测定条件>
装置:BUCHI Melting Point B-545(BUCHI公司制)
<NMR分析条件>
装置:BRUKER AMX 400(Bruker公司制)
溶剂:DMSO-d6
内标:TMS
其结果,新化合物A、B、C及D,分别被鉴定为3-O-当归酰基海藻糖、3-O-乙酰基-3’-O-当归酰基海藻糖、3-O-当归酰基-3’-O-异巴豆酰基海藻糖及3-O-(2-甲基-2-丁烯酰基)-3’-O-(2-甲基-2-戊烯酰基)海藻糖。
〔3.生理机能评价〕
对上述所得化合物,进行生理机能的评价。生理机能的评价,使用Carnosic acid,a catechol-type electrophilic compound,protects neurons both in vitro and invivo through activation of the Keap1/Nrf2 pathway via S-alkylation oftargeted cysteines on Keap1.Takumi Satoh et al.,Journal ofNeurochemistry.Vol.104,pp.1116-1131,(2008)所记载的工具进行。
简单而言,使用10%FBS-DMEM/F12培养基(GIBCO公司制),将ARPE-19细胞播种于24孔盘上,以使其汇聚度达到50%。24小时后,每一孔的用量下,配制(1)0.5μg的pGL3-GSTYaARE-Luciferase载体、0.5μg的pSV-betaGAL载体与50μL的Opti-MEM I(GIBCO公司制)的混合溶液(载体的溶液);及(2)2μL的lipofectamine 2000(赛默飞世尔科技公司制)与50μL的Opti-MEM I(GIBCO公司制)的混合溶液(lipofectamine 2000的溶液),并于室温下静置5分钟。将该载体的溶液与该lipofectamine 2000的溶液混合,于室温下静置20分钟。将此混合液(每1孔100μL)加入培养细胞(ARPE-19细胞)中,在CO2培养器中培养6小时。接着,将培养基交换为新的10%FBS-DMEM/F12培养基(0.5毫升/孔),培养18小时。其后,将培养基交换为新的10%FBS-DMEM/F12培养基(0.3[毫升/孔)或含有20mg/mL的各种Trehangelin衍生物的10%FBS-DMEM/F12培养基(0.3毫升/孔),培养24小时。去除培养基后,加入150μL的被动裂解缓冲液(Passive Lysis Buffer,Promega公司制),以配制细胞溶解液。
在96孔盘中逐孔加入100μL的细胞溶解液,加入100μL的βGAL分析套组溶液(Promega公司制),37℃下培养3小时。其后,通过测定405nm的吸亮度来确认βGAL活性。
在不同于上述的另一个96孔盘中逐孔加入20μL的细胞溶解液,并逐孔加入100μL的荧光素酶分析套组液(Promega公司制)。其后,通过测定荧光来测定荧光素酶活性。通过除以βGAL活性的结果来修正所得荧光素酶活性的结果,计算出抗氧化反应组件(antioxidant responsive element)转录活性。结果示于图1。
(结果)
根据图1,3-O-当归酰基海藻糖、3-O-乙酰基-3’-O-当归酰基海藻糖、3-O-当归酰基-3’-O-异巴豆酰基海藻糖及3-O-(2-甲基-2-丁烯酰基)-3’-O-(2-甲基-2-戊烯酰基)海藻糖,与对照相比,均表现1.24~2.09倍的荧光素酶活性。据此,可知3-O-当归酰基海藻糖、3-O-乙酰基-3’-O-当归酰基海藻糖、3-O-当归酰基-3’-O-异巴豆酰基海藻糖及3-O-(2-甲基-2-丁烯酰基)-3’-O-(2-甲基-2-戊烯酰基)海藻糖具有抗氧化作用。
此外,与作为公知物质的Trehangelin A相比,可知3-O-当归酰基海藻糖具有与Trehangelin A相同程度的抗氧化作用,而3-O-当归酰基-3’-O-异巴豆酰基海藻糖及3-O-(2-甲基-2-丁烯酰基)-3’-O-(2-甲基-2-戊烯酰基)海藻糖具有比Trehangelin A更高的抗氧化作用。
〔4.处方例〕
(化妆水)
作为包含本发明的一个实施方式的化合物的化妆品,由下述组成来制造化妆水。室温下,在下述成分(11)中加入成分(1)~(10)并搅拌。其后,加入成分(12)并均匀溶解,从而得到洗剂(单位为重量%)。
(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)羧基乙烯基聚合物 0.02
(6)甘草酸二钾 0.1
(7)玻尿酸钠 0.1
(8)本发明的一个实施方式的化合物0.1
(9)柠檬酸 0.05
(10)柠檬酸钠 0.1
(11)离子交换水 余量
(12)氢氧化钾 0.01
【工业上的可利用性】
本发明为一种具有抗氧化作用的新化合物,其可应用于化妆品、医药等领域。
序列表
<110> 长濑产业株式会社;学校法人北里研究所
<120> 新化合物及其应用
<130> CPWNHK0004
<150> JP 2019-068164
<151> 2019-03-29
<160> 7
<170> PatentIn version 3.5
<210> 1
<211> 3475
<212> DNA
<213> 红色多形孢菌(Polymorphospora rubra)
<400> 1
gtgacccgac cggacgcccc gggcccaccg gtcgccgccc cggacccggc cgacgccgtc 60
gtgacggccg tcgagccgta cgtggtccgg gcgacgatca accgaccggc ccgccgcaac 120
gccatcgacc tcgccgtgat cgagggcctc gaacgcgcca tcgacctcgc cgaggcgacc 180
ggcgcccggg tcctggtgct gcgcggcgcc ggcggcacct tctgctccgg cgccgacctg 240
cgcgtcctgg aggagatgag cgtcgacccg caccgggtgg agacgttcat ggtgcggctc 300
gccctcgtgc tgcgccggct ggagaccgcc cggttcgtct cggtcgcggt cgtcgagggg 360
cacgccgtcg cgggcggctg cgagatcctg ctcgcctgcg acgtctcggt cgccgccacc 420
gacgcccgca tcggcgaccg ccatctcgag tacgggctgg tccccgccgc cggcggctcg 480
gtacggctgg cccgcaccct gcccaaggcc cggggcaact acctgctgct cgccgccgac 540
ctgctcaccg gggagcaggc ggcgcagtgg ggactggtca gcgtcgcggt gccgccaacc 600
gacctggaac cccgggtgga cgccctggtc gggcggctcg tcggccacag cgccgacgcg 660
ctcgccgtgg tcaagaagat ggtctggacc gccgaccacg aaccccggcc ggacgccatg 720
tcctgggaac gccggctctt cctgcgccac ctcggctccg aagacgtgtc cgaggggctg 780
cgcgccttcc gcgagcggcg ccggccggcg ttccgcgccg atgactgact ccgtacggcc 840
gcccgaccgg acggcccgac cgcaaggaga ccacatgtcg acctcgacgg tgatcggaac 900
aggttcgtac ctaccccgcc gcgtcctcag cagcggcgaa ctggcccgcc gggtcggtgt 960
ggcggagaac tggatcgtgg agaagaccgg gatccgggaa cgccgggtgg ccgccgacga 1020
ggaggccacc tccgacctgg ccacccgggc cgcgcgccgg gcgctgcgga ccgcccggct 1080
ggacccggcc gacgtcgacc tgatcgtgct ggcgacctcc acaccggacc ggccgatgcc 1140
ggccaccgcc agcaccgtgc aggccaacct cggcgcccgc caggcggtcg cgttcgacgt 1200
cgacgcggtg tgcagcggct tcgtgtacgc cctcgtcgtc gcccactcga tgctgaacag 1260
cgagggctgg gcccgtaccg cgctggtgat cggcgccgac acgtactcgc gggtcctgga 1320
ctacaccgac cggcgtaccg cggtgctctt cggcgacggt gccggcgcgg tcgtcctcgg 1380
ccgggagacc ggcggcggga gcggaatccg ggccaccacc ctgggcaccg acggcaccct 1440
cgccgacctc gtccagatcc cggccggcgg cagccgccgg ccggcgagcg cgcagacggt 1500
cgaggccggc gaccactact tcgcgatgcg cggcggcgac gtccgcaggc tggccaacca 1560
ggtcttcccg gcactggtcg ggcaactgct caaggcggcc tcgctcgacc tggaccaggt 1620
cgacctgatc gccgcccacc aggccaacgg cacgatgctc accgactggt cgcgggacct 1680
cggcctgcgc ccgggggtgc tgcaccgcac cgtcgagcgg tacggcaaca ccggtgccgc 1740
ctcggtcccg gtcaccctcg acgacgccgt acgcaccggg cggctcggtg ccgccgccac 1800
cctgctgatg gtcgccttcg gcggcgggat gacctggggc ggcgtcgccc tggactggtc 1860
cgccgacccg tcggttcccc gctccaactg cgtgaggtga agtgatgacc acgtccgcac 1920
tcggcgccga accgggcgcc accgatccgc cggccgcccc gccggtctcc tacgccccgt 1980
ccggccggat gccccggacg atcaaccgct ggccgcgccc gttcgcgccg cgcaacatcc 2040
tcggcgtgct gcgggcccgg ctgcgcggcg ccacgatcag cctcaaccag gtcaagttcg 2100
acgagtccac cgcggagcgc aacgcgctgg tgatggaaca cgcgctgctg cggcacagcc 2160
acgtcgcccg gtacgcgatc gtcggcccgt tcacctcgct gttcaaggtc cgggtcggcc 2220
cgtacgccgg gatcgccgag aaggtgaccg tcggtgccct gccgcactgg ccggaactgc 2280
cgaccagtca cgtcttcccg gtcaacgccg agttcggctt ctgcgcgggg gagtggccgg 2340
aggtgcccgg caccgaggtc ggcgccgacg cgtggatcgg cgccggcgcg gtggtccggg 2400
ccggcgtccg gatcgggcac ggcgcgatcg tcgcggccgg cgcggtcgtc acccgcgacg 2460
tcgccgacta cgagatcgtg gccggggtgc cggcccgccg gctgcggtcc cggttccccg 2520
acgacctggc cgaacggctg gtcgcgctgg cctggtggga ctggccgccg gggttcatca 2580
aggccaacat cgacctgttc cagcggccgc tgaccgccga caccctggcc gcgctggagg 2640
agcgggcccg cgccctgccc acacccccgg gtggtgccgc gtgaccgccg gtacgggcca 2700
gccggtcgtc gccgcgcccg gcagggcgct cgccgaccgg gtggtggtgg tgaccggcgc 2760
cagccgcggt gtcggccgcg acctcgcccg ggtgttcgcc gaccacggcg cccgcctcgg 2820
cctgctggcc cgcagccggg acgcgctcga cgacctcggc ggcacgctca ccgccgccgg 2880
tgccgacgtc ctcgccgtgc cgtgcgacgt cggcgaaccg gactcgctgg ccggcgcggt 2940
cgacgccgtc gccgggcact tcggagggat cgactcggtc gtcgtcaacg ccggcatctc 3000
gcccgtcgcc cgtcgggcgc accacctgcc gatcgacgcc tggcacgacg tgctggcgac 3060
caacctgacc ggcgggttcg tcacggcgcg ggcggcgtat ccgcacctgg cccgctcggg 3120
gcgtggccgg ctggtgttca ccacctcggt catggccgcc accccgcggc gcgggctgag 3180
cgcgtacgcg gcgtcgaagg ccggcctgga ggggctcacc cgggccctgg ccgctgactg 3240
ggcgggggac ggaatcctgg tcaacgcggt cgcgccgggg ttcttcgaca ccgggctcgg 3300
cgccgccttc cacacctcgc agcgcctgca cgagcaggtc gtcggtcgta cgccggtggc 3360
ccggttcggc cgcgccgacg agttggccgc cgcgttcgtc ttcctggccg gtgacgcctg 3420
cggttacctg accggtcagg tgctcgccgt cgacggcggc tacggcctgg gctga 3475
<210> 2
<211> 828
<212> DNA
<213> 红色多形孢菌(Polymorphospora rubra)
<400> 2
gtgacccgac cggacgcccc gggcccaccg gtcgccgccc cggacccggc cgacgccgtc 60
gtgacggccg tcgagccgta cgtggtccgg gcgacgatca accgaccggc ccgccgcaac 120
gccatcgacc tcgccgtgat cgagggcctc gaacgcgcca tcgacctcgc cgaggcgacc 180
ggcgcccggg tcctggtgct gcgcggcgcc ggcggcacct tctgctccgg cgccgacctg 240
cgcgtcctgg aggagatgag cgtcgacccg caccgggtgg agacgttcat ggtgcggctc 300
gccctcgtgc tgcgccggct ggagaccgcc cggttcgtct cggtcgcggt cgtcgagggg 360
cacgccgtcg cgggcggctg cgagatcctg ctcgcctgcg acgtctcggt cgccgccacc 420
gacgcccgca tcggcgaccg ccatctcgag tacgggctgg tccccgccgc cggcggctcg 480
gtacggctgg cccgcaccct gcccaaggcc cggggcaact acctgctgct cgccgccgac 540
ctgctcaccg gggagcaggc ggcgcagtgg ggactggtca gcgtcgcggt gccgccaacc 600
gacctggaac cccgggtgga cgccctggtc gggcggctcg tcggccacag cgccgacgcg 660
ctcgccgtgg tcaagaagat ggtctggacc gccgaccacg aaccccggcc ggacgccatg 720
tcctgggaac gccggctctt cctgcgccac ctcggctccg aagacgtgtc cgaggggctg 780
cgcgccttcc gcgagcggcg ccggccggcg ttccgcgccg atgactga 828
<210> 3
<211> 1026
<212> DNA
<213> 红色多形孢菌(Polymorphospora rubra)
<400> 3
atgtcgacct cgacggtgat cggaacaggt tcgtacctac cccgccgcgt cctcagcagc 60
ggcgaactgg cccgccgggt cggtgtggcg gagaactgga tcgtggagaa gaccgggatc 120
cgggaacgcc gggtggccgc cgacgaggag gccacctccg acctggccac ccgggccgcg 180
cgccgggcgc tgcggaccgc ccggctggac ccggccgacg tcgacctgat cgtgctggcg 240
acctccacac cggaccggcc gatgccggcc accgccagca ccgtgcaggc caacctcggc 300
gcccgccagg cggtcgcgtt cgacgtcgac gcggtgtgca gcggcttcgt gtacgccctc 360
gtcgtcgccc actcgatgct gaacagcgag ggctgggccc gtaccgcgct ggtgatcggc 420
gccgacacgt actcgcgggt cctggactac accgaccggc gtaccgcggt gctcttcggc 480
gacggtgccg gcgcggtcgt cctcggccgg gagaccggcg gcgggagcgg aatccgggcc 540
accaccctgg gcaccgacgg caccctcgcc gacctcgtcc agatcccggc cggcggcagc 600
cgccggccgg cgagcgcgca gacggtcgag gccggcgacc actacttcgc gatgcgcggc 660
ggcgacgtcc gcaggctggc caaccaggtc ttcccggcac tggtcgggca actgctcaag 720
gcggcctcgc tcgacctgga ccaggtcgac ctgatcgccg cccaccaggc caacggcacg 780
atgctcaccg actggtcgcg ggacctcggc ctgcgcccgg gggtgctgca ccgcaccgtc 840
gagcggtacg gcaacaccgg tgccgcctcg gtcccggtca ccctcgacga cgccgtacgc 900
accgggcggc tcggtgccgc cgccaccctg ctgatggtcg ccttcggcgg cgggatgacc 960
tggggcggcg tcgccctgga ctggtccgcc gacccgtcgg ttccccgctc caactgcgtg 1020
aggtga 1026
<210> 4
<211> 780
<212> DNA
<213> 红色多形孢菌(Polymorphospora rubra)
<400> 4
atgaccacgt ccgcactcgg cgccgaaccg ggcgccaccg atccgccggc cgccccgccg 60
gtctcctacg ccccgtccgg ccggatgccc cggacgatca accgctggcc gcgcccgttc 120
gcgccgcgca acatcctcgg cgtgctgcgg gcccggctgc gcggcgccac gatcagcctc 180
aaccaggtca agttcgacga gtccaccgcg gagcgcaacg cgctggtgat ggaacacgcg 240
ctgctgcggc acagccacgt cgcccggtac gcgatcgtcg gcccgttcac ctcgctgttc 300
aaggtccggg tcggcccgta cgccgggatc gccgagaagg tgaccgtcgg tgccctgccg 360
cactggccgg aactgccgac cagtcacgtc ttcccggtca acgccgagtt cggcttctgc 420
gcgggggagt ggccggaggt gcccggcacc gaggtcggcg ccgacgcgtg gatcggcgcc 480
ggcgcggtgg tccgggccgg cgtccggatc gggcacggcg cgatcgtcgc ggccggcgcg 540
gtcgtcaccc gcgacgtcgc cgactacgag atcgtggccg gggtgccggc ccgccggctg 600
cggtcccggt tccccgacga cctggccgaa cggctggtcg cgctggcctg gtgggactgg 660
ccgccggggt tcatcaaggc caacatcgac ctgttccagc ggccgctgac cgccgacacc 720
ctggccgcgc tggaggagcg ggcccgcgcc ctgcccacac ccccgggtgg tgccgcgtga 780
<210> 5
<211> 795
<212> DNA
<213> 红色多形孢菌(Polymorphospora rubra)
<400> 5
gtgaccgccg gtacgggcca gccggtcgtc gccgcgcccg gcagggcgct cgccgaccgg 60
gtggtggtgg tgaccggcgc cagccgcggt gtcggccgcg acctcgcccg ggtgttcgcc 120
gaccacggcg cccgcctcgg cctgctggcc cgcagccggg acgcgctcga cgacctcggc 180
ggcacgctca ccgccgccgg tgccgacgtc ctcgccgtgc cgtgcgacgt cggcgaaccg 240
gactcgctgg ccggcgcggt cgacgccgtc gccgggcact tcggagggat cgactcggtc 300
gtcgtcaacg ccggcatctc gcccgtcgcc cgtcgggcgc accacctgcc gatcgacgcc 360
tggcacgacg tgctggcgac caacctgacc ggcgggttcg tcacggcgcg ggcggcgtat 420
ccgcacctgg cccgctcggg gcgtggccgg ctggtgttca ccacctcggt catggccgcc 480
accccgcggc gcgggctgag cgcgtacgcg gcgtcgaagg ccggcctgga ggggctcacc 540
cgggccctgg ccgctgactg ggcgggggac ggaatcctgg tcaacgcggt cgcgccgggg 600
ttcttcgaca ccgggctcgg cgccgccttc cacacctcgc agcgcctgca cgagcaggtc 660
gtcggtcgta cgccggtggc ccggttcggc cgcgccgacg agttggccgc cgcgttcgtc 720
ttcctggccg gtgacgcctg cggttacctg accggtcagg tgctcgccgt cgacggcggc 780
tacggcctgg gctga 795
<210> 6
<211> 37
<212> DNA
<213> 人工序列
<220>
<223> 引物
<400> 6
aaagggctgc agaggaggcg taccgtgacc cgaccgg 37
<210> 7
<211> 30
<212> DNA
<213> 人工序列
<220>
<223> 引物
<400> 7
aaagggaggc ctgctcagcc caggccgtag 30
Claims (8)
1.一种化合物,其为下述式(1)所表示的化合物:
[化1]
式中,R1~R3中的任意一个为氢、乙酰基、2-丁烯酰基或2-甲基-2-戊烯酰基,其余2个为氢;且R4~R6中的任意一个为2-甲基-2-丁烯酰基,其余2个为氢。
2.如权利要求1所述的化合物,其中,所述式(1)中,R2为氢、乙酰基、2-丁烯酰基或2-甲基-2-戊烯酰基,R5为2-甲基-2-丁烯酰基,R1、R3、R4及R6为氢。
3.包含权利要求1所述的化合物的组合物。
4.包含权利要求2所述的化合物的组合物。
5.如权利要求3所述的组合物,其中,所述组合物进一步包含下述
式(6)~(8)所表示的化合物中的至少一种,
[化6]
[化7]
[化8]
6.如权利要求4所述的组合物,其中,所述组合物进一步包含下述式(6)~(8)所表示的化合物中的至少一种,
[化6]
[化7]
[化8]
7.如权利要求3~6中任一项所述的组合物,其中,所述组合物为化妆品组合物或抗氧化剂。
8.权利要求1或2所述的化合物的制造方法,其包括:
(A)在培养基中培养具有生产权利要求1或2所述的化合物的能力的微生物的步骤;及
(B)从培养物中收集权利要求1或2所述的化合物的步骤;
所述微生物为导入编码参与合成trehangelin的酶的基因的变铅青链霉菌,所述参与合成trehangelin的酶包括:烯酰基辅酶A水合酶、3-酮酰基-辅酶A合成酶、酰基转移酶和3-酮酰基-辅酶A还原酶。
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JP2019068164 | 2019-03-29 | ||
JP2019-068164 | 2019-03-29 | ||
PCT/JP2020/004718 WO2020202790A1 (ja) | 2019-03-29 | 2020-02-07 | 新規化合物およびその利用 |
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US (1) | US20220177507A1 (zh) |
EP (1) | EP3950697A4 (zh) |
KR (1) | KR20210143901A (zh) |
CN (1) | CN113631562B (zh) |
BR (1) | BR112021019566A2 (zh) |
CA (1) | CA3134882A1 (zh) |
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WO (1) | WO2020202790A1 (zh) |
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US5049664A (en) * | 1988-08-26 | 1991-09-17 | Sawai Pharmaceutical Co., Ltd. | Trehalose derivatives |
JPH11100597A (ja) * | 1997-09-25 | 1999-04-13 | Pola Chem Ind Inc | α,αグルコシルグルコシド含有石鹸 |
WO2005113568A1 (en) * | 2004-05-21 | 2005-12-01 | Forskarpatent I Syd Ab | Novel galactoside inhibitors of galectins |
WO2014034147A1 (ja) * | 2012-09-03 | 2014-03-06 | 学校法人北里研究所 | 新規光線過敏症抑制剤トレハンジェリン物質及びその製造法 |
JP2015024985A (ja) * | 2013-06-19 | 2015-02-05 | 学校法人北里研究所 | 化粧料または皮膚外用剤 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US10202627B2 (en) * | 2016-03-04 | 2019-02-12 | The Kitasato Institute | Method for producing trehangelin |
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2020
- 2020-02-07 US US17/599,234 patent/US20220177507A1/en active Pending
- 2020-02-07 CA CA3134882A patent/CA3134882A1/en active Pending
- 2020-02-07 BR BR112021019566A patent/BR112021019566A2/pt unknown
- 2020-02-07 KR KR1020217035105A patent/KR20210143901A/ko active Search and Examination
- 2020-02-07 CN CN202080025804.0A patent/CN113631562B/zh active Active
- 2020-02-07 WO PCT/JP2020/004718 patent/WO2020202790A1/ja unknown
- 2020-02-07 EP EP20784399.6A patent/EP3950697A4/en active Pending
- 2020-03-11 TW TW109108060A patent/TWI827814B/zh active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5049664A (en) * | 1988-08-26 | 1991-09-17 | Sawai Pharmaceutical Co., Ltd. | Trehalose derivatives |
JPH11100597A (ja) * | 1997-09-25 | 1999-04-13 | Pola Chem Ind Inc | α,αグルコシルグルコシド含有石鹸 |
WO2005113568A1 (en) * | 2004-05-21 | 2005-12-01 | Forskarpatent I Syd Ab | Novel galactoside inhibitors of galectins |
WO2014034147A1 (ja) * | 2012-09-03 | 2014-03-06 | 学校法人北里研究所 | 新規光線過敏症抑制剤トレハンジェリン物質及びその製造法 |
JP2015024985A (ja) * | 2013-06-19 | 2015-02-05 | 学校法人北里研究所 | 化粧料または皮膚外用剤 |
Non-Patent Citations (2)
Title |
---|
Biosynthesis of Trehangelin in Polymorphospora rubra K07–0510: Identification of Metabolic Pathway to Angelyl-CoA;Yuki Inahashi et al.;《ChemBioChem》;第17卷(第15期);1442-1447 * |
Trehangelins A, B and C, novel photo-oxidative hemolysis inhibitors produced by an endophytic actinomycete, Polymorphospora rubra K07-0510;Takuji Nakashima et al.;《Journal of Antibiotics》;第66卷(第6期);311-317 * |
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Publication number | Publication date |
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KR20210143901A (ko) | 2021-11-29 |
TW202102199A (zh) | 2021-01-16 |
JPWO2020202790A1 (zh) | 2020-10-08 |
EP3950697A4 (en) | 2023-01-25 |
US20220177507A1 (en) | 2022-06-09 |
BR112021019566A2 (pt) | 2021-12-07 |
EP3950697A1 (en) | 2022-02-09 |
CN113631562A (zh) | 2021-11-09 |
TWI827814B (zh) | 2024-01-01 |
WO2020202790A1 (ja) | 2020-10-08 |
CA3134882A1 (en) | 2020-10-08 |
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