CN103601663B - 一种色胺衍生物类化合物及其制备方法和用途 - Google Patents
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Abstract
本发明公开了一种色胺衍生物类化合物及其制备方法和用途,特点是该色胺衍生物类化合物的结构如(I)所示,制备方法包括将假交替单胞菌保藏号为CGMCC No.6555划线接种到固体斜面培养基上,于30℃培养箱中培养1天后;将斜面培养获得的菌落接种1个菌落到400ml液体培养基中,于30℃,150rpm下摇床培养7天,获得发酵产物的步骤;将发酵产物去除菌体,取发酵液加入等体积的乙酸乙酯充分萃取3次,合并萃取液,用旋转蒸发仪将乙酸乙酯去除获得粗浸膏的步骤;最后将粗浸膏用甲醇溶解后,用半制备反相高效液相色谱进行分离纯化得到产品,优点是该化合物对金黄色葡萄球菌和大肠杆菌的生长均有较强抑制作用。
Description
技术领域
本发明涉及一种色胺衍生物,尤其是涉及一种色胺衍生物类化合物及其制备方法和用途。
背景技术
色胺衍生物类化合物是生物碱类化合物的一员,具有独特的药理及生理活性,在临床上被广泛使用。本发明人研究得知,假交替单胞菌Pseudoalteromonas rubra QD1-2(保藏于中国微生物菌种保藏管理委员会普通微生物中心,保藏号为CGMCC No.6555)液体发酵产物经乙酸乙酯提取,提取物有很好的细胞增殖抑制活性,于是对其活性成分进行了研究。研究发现目前尚未见该化合物的化学结构及抑菌活性的报道,因此市场上也尚未见有与此相关的药物。
发明内容
本发明所要解决的技术问题是提供一种对金黄色葡萄球菌和大肠杆菌的生长均有较强抑制作用的色胺衍生物类化合物及其制备方法和用途。
本发明解决上述技术问题所采用的技术方案为:
1、一种色胺衍生物类化合物,该色胺衍生物类化合物的结构式如下所示,
2、一种色胺衍生物类化合物的制备方法,具体包括如下步骤:
(1)发酵生产
将假交替单胞菌(Pseudoalterommonas rubra QD1-2)保藏号为CGMCCNo.6555划线接种到Zobell2216E固体斜面培养基上,于30℃培养箱中培养1天后;将斜面培养获得的菌落接种1个菌落到400ml Zobell2216E液体培养基中,于30℃,转速150rpm的条件下摇床培养15天,获得发酵产物;
(2)浸膏的获得
将发酵产物用离心机离心去除菌体,获得发酵液,取发酵液加入等体积的乙酸乙酯充分萃取1次,收集萃取液,再取萃余液加入等体积的乙酸乙酯重复萃取1次,收集萃取液,再将获得的萃余液加入等体积的乙酸乙酯重复萃取1次,合并三次萃取所得萃取液,用旋转蒸发仪将乙酸乙酯去除,获得粗浸膏;
(3)化合物的分离精制
将粗浸膏用甲醇溶解后,用半制备反相高效液相色谱进行分离纯化得到色胺衍生物类化合物,其结构如下所示:
所述的Zobell2216E培养基的配制方法如下:蛋白胨5.0g,酵母膏1.0g,磷酸铁0.01g,琼脂16.0g,陈海水1000ml,调pH至7.6-7.8。
所述的半制备反相高效液相色谱的洗脱液为甲醇与水按体积65:35的比例混合。
3、一种色胺衍生物类化合物的用途,该色胺衍生物类化合物具有抑制金黄色葡萄球菌和大肠杆菌的生长的作用,具有作为制备抗菌药物的潜在用途。
所述的色胺衍生物类化合物抗金黄色葡萄球菌的MIC为2.5ug/ml,抗大肠杆菌的MIC值为1.2ug/ml。
与现有技术相比,本发明的优点在于:本发明一种色胺衍生物类化合物及其制备方法和用途,通过微生物发酵培养来获色胺衍生物类化合物的发酵物,然后将发酵产物用乙酸乙酯提取,得粗浸膏,将该提取物经反相半制备高效液相色谱分离纯化得到,该色胺衍生物类化合物具有抑制抑制金黄色葡萄球菌和大肠杆菌的生长的作用。
上述假交替单胞菌(Pseudoalteromonas rubra.QD1-2),该菌为QD1-2菌株,保藏编号为CGMCCNo.6555,于2012年09月11日保藏于中国微生物菌种保藏管理委员会普通微生物中心,保藏地址为北京市朝阳区北辰西路1号院3号。
具体实施方式
以下结合实施例对本发明作进一步详细描述。
实施例1
一种色胺衍生物类化合物结构式如Ⅰ所示。
实施例2
如I式所示的色胺衍生物类化合物的制备方法,具体包括如下步骤:
(1)发酵生产
将假交替单胞菌(Pseudoalteromonas rubra QD1-2)保藏号为CGMCCNo.6555划线接种到Zobell2216E固体斜面培养基上,于30℃培养箱中培养1天后;将斜面培养获得的菌落接种1个菌落到400ml Zobell2216E液体培养基中,于30℃,转速150rpm的条件下摇床培养15天,获得发酵产物;
(2)浸膏的获得
将发酵产物用离心机离心去除菌体,获得发酵液,取发酵液加入等体积的乙酸乙酯充分萃取1次,收集萃取液,再取萃余液加入等体积的乙酸乙酯重复萃取1次,收集萃取液,再将获得的萃余液加入等体积的乙酸乙酯重复萃取1次,合并三次萃取所得萃取液,用旋转蒸发仪将乙酸乙酯去除,获得粗浸膏;
(3)化合物的分离精制
将粗浸膏用甲醇溶解后,用半制备反相高效液相色谱进行分离纯化得到色胺衍生物类化合物,其结构如下所示:
所述的Zobell2216E培养基的配制方法如下:蛋白胨5.0g,酵母膏1.0g,磷酸铁0.01g,琼脂16.0g,陈海水1000ml,调pH至7.6-7.8。
所述的半制备反相高效液相色谱的洗脱液为甲醇与水按体积65:35的比例混合而成。
该化合物Ⅰ淡黄色粉末,分子式C17H24N2O,ESI-MS m/z:295.07[M+Na]+,1H和13C-NMR数据见表1。
表1化合物Ⅰ的1H和13CNMR数据(400MHz和100MHz,in CDCl3)a
注:a)表示本表信号归属基于DEPT、1H-1H COSY、HMQC及HMBC图谱解析结果。氢信号多重度分别用s(单重峰)、d(二重峰)、t(三重峰)和q(四重峰)表;b)表示此栏中的数字和代号分别代表在1H-1H COSY谱中与相应行中的1H给出偶合相关信号的1H核;
c)表示此栏中的数字和代号分别代表在HMBC谱中与相应行中的1H给出偶合相关信号的13C核。
实施例3
体外抗菌活性的测试(96孔板抑菌测试)
(1)实验样品
被测样品溶液的配制:测试样品为上述实施例1中分离纯化的化合物Ⅰ纯品,精密称取适量样品,用甲醇配制成所需浓度的溶液,供测活性。
该实验使用的指示菌为金黄色葡萄球菌和大肠杆菌。
(2)实验方法
96孔板抑菌测试方法:配制培养基后,灭菌两个小时左右,烘干冷却后用于活化菌种。将金黄色葡萄球菌和大肠杆菌接种在固体培养基中,37℃下培养24小时。固体培养基中菌种接种到液体培养基37℃下培养12小时。菌体悬浮液加入96孔板,加入各梯度待检测化合物,待测化合物所用溶剂作为对照组,50μg/ml氯霉素作阳性对照,甲醇溶液为阴性对照,其中甲醇溶液浓度与被测样品溶液中甲醇浓度相同。37℃培养24小时。待测化合物的浓度分别为5μg/ml、10μg/ml、25μg/ml、50μg/ml。24小时之后,测定600nm下吸光值。根据如下公式计算抑制率。
抑制率(%)=(ODR-OD)/(ODR-ODB)
ODR:菌液对照孔吸光值;ODB:空白吸光值;OD:样品测定孔吸光值。
(3)实验结果
在96孔板抑菌测试中,不同浓度的化合物Ⅰ对金黄色葡萄球菌和大肠杆菌的抑制结果见表2。
表2不同浓度的化合物Ⅰ对指示菌的抑制率(%)
由上表可知化合物Ⅰ具有显著的抗金黄色葡萄球菌和大肠杆菌的作用,可用于细菌抑制剂方面的研究。
采用微量肉汤稀释法(Wang,W.et al.J.Nat.Prod.2012,75,2049-2054)测定对金黄色葡萄球菌和大肠杆菌的MIC值。结果显示,化合物Ⅰ抗金黄色葡萄球菌的MIC为2.5ug/ml,抗大肠杆菌的MIC值为1.2ug/ml。本发明的化合物Ⅰ对金黄色葡萄球菌和大肠杆菌的生长均有较强的抑制作用,具有作为制备抗菌药物的潜在用途。
上述说明并非对本发明的限制,本发明也并不限于上述举例。本技术领域的普通技术人员在本发明的实质范围内,作出的变化、改型、添加或替换,也应属于本发明的保护范围。
Claims (2)
1.一种色胺衍生物类化合物的用途,该色胺衍生物类化合物的结构式如下所示,
其特征在于:所述的色胺衍生物类化合物作为制备抑制金黄色葡萄球菌和大肠杆菌生长方面药物的应用。
2.根据权利要求1所述的一种色胺衍生物类化合物的用途,其特征在于:所述的色胺衍生物类化合物抗金黄色葡萄球菌的MIC为2.5ug/ml,抗大肠杆菌的MIC值为1.2ug/ml。
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