CN101863936B - 短指软珊瑚中一种具有抗菌活性的开环甾体皂苷类化合物 - Google Patents
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Abstract
本发明涉及医药技术领域，是从短指软珊瑚中分离得到的具有抗菌作用的两个开环甾体皂苷类化合物Sinularoside A和Sinularoside B，它们的化学结构通式如下：
其R基团为
其中，Sinularoside A的Sinularoside B的
Description
技术领域
本发明涉及医药技术领域，是从海洋动物短指软珊瑚中分离到的一种新的具有抗菌活性的开环甾体皂苷类化合物Sinularoside A和Sinularoside B。
背景技术
我国南海海域辽阔，地处亚热带，软珊瑚资源尤其丰富，是世界上软珊瑚集中分布的海域之一。短指软珊瑚在南海海域内广泛分布，数量众多。短指软珊瑚(Sinularia.sp)属腔肠动物门(Coelenterata)珊瑚虫纲(Anthoaoa)八放珊瑚亚纲(Octocorallia)软珊瑚目(Alcyonacea)软珊瑚科(Alcyoniidae)动物。短指软珊瑚化学成分研究始于1975年，多年来对该属软珊瑚的研究一直非常活跃。到目前为止，已研究了该属中42个的化学成分。这些化学成分主要有萜类(尤其是西松烯二萜)、甾醇类、含氮化台物和一些长链脂肪酸、酯、醇类等。已从该种珊瑚中分离得到开环甾体类化合物，但未见有关从该种珊瑚甚至整个珊瑚动物中提取分离得到开环甾体苷成分的报道。
发明内容
本发明提供一种从短指软珊瑚中提取分离到的两个开环甾体苷类化合物，化学式分别为C36H58O8和C34H56O7，分别命名为Sinularoside A和Sinularoside B，它们的化学结构通式如下：
其R基团为
其中，
Sinularoside A的
Sinularoside B的
Sinularoside A为无色油状固体，由高分辨质谱(HR-ESI-MS+)中准分子离子峰提供的精确分子量m/z 641.4026[M+Na]+，(Calcd.forC36H58O8Na，6418.4026)，给出该化合物的分子式C36H58O8，分子量618；红外光谱：3418(OH)，2956；2927(CH3，CH2)，1738(C＝O)，1716(C＝O)，1671(C＝C)；1H和13C核磁共振数据见表1。
Sinularoside B为无色油状固体，由高分辨质谱(HR-ESI-MS+)中准分子离子峰提供的精确分子量m/z599.3929[M+Na]+，(Calcd.forC34H56O7Na，6418.4026)，给出该化合物的分子式C34H56O7，分子量576.3929；红外光谱：3359(OH)，3192(C＝C)，2923；2852(CH3，CH2)，1633(C＝O)，1658(C＝C)；1H和13C核磁共振数据见表1。
表1.Sinularoside A和Sinularoside B的1H和13C核磁共振数据(600MHz/125MHz)
J值：偶合常数
本发明Sinularoside A和Sinularoside B的制备方法如下：
1.制备总浸膏：
取新鲜的短指软珊瑚洗净剪碎，用重量比为5～10倍的丙酮超声提取至提取液无色，减压回收丙酮至干，用等体积水分散，乙醚分次萃取，合并萃取液，减压回收乙醚浓缩至干，得总浸膏；
2.分离纯化
将总浸膏用正相硅胶色谱(200～300目)分离，用石油醚/丙酮系统梯度洗脱，根据薄层板检测监测，分别收集、合并得部分1和部分2。部分1经过Sephandex LH-20凝胶柱色谱，流动相体积比为1∶1的三氯甲烷/甲醇洗脱，根据薄层板检测监测，分别收集、合并得部分a和b。将a部分进行反相高效液相色谱分离，以甲醇∶水的体积比为90∶10的混合溶剂进行洗脱，根据示差检测器监测，收集含Sinularoside A流份，减压回收甲醇并浓缩至干，得Sinularoside A。将部分2进行反相高效液相色谱分离，以甲醇∶水的体积比为90∶10的混合溶剂进行洗脱，根据示差检测器监测，减压回收甲醇并浓缩至干，得Sinularoside B。
对Sinularoside A和Sinularoside B进行的体外抗菌试验表明，它们对于试验用真菌、细菌和藻类具有明显的抑制效果，因此，可用于制备抗菌药物。
本发明为研制新的抗菌药物提供了新的先导化合物，为开发利用中国的海洋药用生物资源具有重要意义。
具体实施方式
现结合实施例对本发明作详细描述。
实施例1.制备Sinularoside A和Sinularoside B
取中国广西涠洲岛海域的短指软珊瑚(Sinularia.sp)2600克，洗净，剪碎，用6倍重量的丙酮超声提取，减压回收丙酮至无丙酮味，用等体积水分散，乙醚萃取6次，每次1000毫升，合并萃取液，回收乙醚并浓缩至干，得总浸膏14.6g。将总浸膏经正相硅胶色谱(200～300目)分离，以体积比为1∶1～0∶1的石油醚/丙酮梯度洗脱，根据薄层板监测，收集并合得部分1(0.21g)和部分2(0.43g)。部分1经过Sephandex LH-20凝胶柱色谱，流动相体积比为1∶1的三氯甲烷/甲醇洗脱，根据薄层板监测，分别收集、合并，得部分a和b。将a部分进行反相高效液相色谱分离，以甲醇∶水的体积比为90∶10的混合溶剂进行洗脱，根据示差检测器监测，收集含Sinularoside A流份，减压回收甲醇并浓缩至干，得Sinularoside A 6.5毫克。将部分2进行反相高效液相色谱分离，以甲醇∶水的体积比为90∶10的混合溶剂进行洗脱，根据示差检测器监测，收集含Sinularoside B流份，减压回收甲醇并浓缩至干，得Sinularoside B 4.8毫克。
体外抗菌试验
一、试验用真菌、细菌和藻类
1.试验用真菌：花药黑粉菌(Microbotryum violaceum)、灰霉菌(Botrytiscinerea)和壳针孢叶枯病菌(Septoria tritici)；
2.试验用细菌：大肠杆菌(Escherichia coli)、巨大芽孢杆菌(Bacillusmegaterium)；
3.试验用藻类：小球藻(Chlorella fusca)。
二、实验用药
1.阳性对照药：青霉素(Penicillin)、链霉素(Streptomycin)；
2.阴性对照品：丙酮(Acetone)；
3.Sinularoside A和Sinularoside B，由实施例1制备
三.实验方法：
1.配制药物溶液：将青霉素、链霉素、Sinularoside A和SinularosideB分别用丙酮配制成浓度为1mg/ml的溶液，单次测试用量50μl。
2.将上述3种真菌、2种细菌和1种藻类按无菌操作的要求分别用7ml灭菌水配制成菌液，各用喷雾器取4ml菌液，分别均匀喷洒于各自培养皿的培养基表面，再在每个培养皿内分别放置直径约1cm灭菌滤纸两块，覆盖于培养基表面，然后分别取上述配制的药液50μl滴于滤纸上，盖上培养基盖子进行培养。各培养皿盖子上均注明相应培养基种类、菌种、化合物名称、接种时间。花药黑粉菌室温4天，灰霉菌室温5天，壳针孢叶枯病菌20℃4天，大肠杆菌37度24小时，巨大芽孢杆菌37℃24小时，小球藻20℃5天。按时观察结果，测量抑菌圈的大小(直径)，平行试验3次，结果见表2。
表2.琼脂扩散实验活性筛选(mm)
由表2可见，本发明inularoside A和Sinularoside B对花药黑粉菌、壳针孢叶枯病菌、巨大芽孢杆菌和小球藻均具有显著的抑制作用，因此可用于制备抗菌药物。
Claims (2)
1.一种开环甾体皂苷类化合物Sinularoside A和Sinularoside B，其特征在于它们的化学结构通式如下：
其R基团为
其中，
Sinularoside A的
Sinularoside B的
2.权利要求1所述的开环甾体皂苷类化合物Sinularoside A或Sinularoside B在制备抗菌药物中的应用。
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