基于活性筛选和化学筛选的短萼仪花茎皮活性成分的研究
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摘要
短萼仪花(Lysidice brevicalyx Wei)为豆科(Leguminosae)仪花属(LysidiceHance)属植物,又名麻忆木,分布于广东、广西、云南、贵州等地。其根、茎、叶可入药,能散瘀消肿,止血止痛。
     在文献调研和本实验室的工作基础上,本文设计了基于活性筛选和化学筛选来研究短萼仪花活性成分的整体研究思路,为建立高效、快速发现新型结构活性天然产物的研究方法作出有意义的探索。
     在药理活性筛选的基础上,主要利用LC/UV和LC/ESI-MS~n等化学筛选手段,对短萼仪花茎皮95%乙醇提取物中具抗氧化活性的组分进行快速筛选,一共获取了53个成分的结构信息,初步判断了它们的结构类型并推测了部分成分的可能结构,发现16个值得研究的未知成分。
     根据化学筛选结果,锁定并分离得到这16个可能为新化合物的未知成分,采用波谱和化学方法确定其结构为:(E)-5,4′-二羟基-二苯乙烯3-O-β-D-吡喃木糖-(1→6)-β-D-吡喃葡萄糖苷(1)、(E)-5,4′-二羟基-二苯乙烯3-O-β-D-吡喃葡萄糖-(1→2)-β-D-吡喃木糖苷(2)、(E)-5,4′-二羟基-二苯乙烯3-O-α-L-吡喃鼠李糖-(1→2)-β-D-吡喃葡萄糖苷(3)、(Z)-5,4′-二羟基-二苯乙烯3-O-α-L-吡喃鼠李糖-(1→2)-β-D-吡喃葡萄糖苷(4)、(Z)-5,4′-二羟基-二苯乙烯3-O-α-L-吡喃鼠李糖-(1→6)-β-D-吡喃葡萄糖苷(5)、(E)-5,4′-二羟基-二苯乙烯3-O-{α-L-吡喃鼠李糖-(1→2)-[α-L-吡喃鼠李糖-(1→6)]-β-D-吡喃葡萄糖苷(6)、(Z)-5,4′-二羟基-二苯乙烯3-O-{α-L-吡喃鼠李糖-(1→2)-[α-L-吡喃鼠李糖-(1→6)]-β-D-吡喃葡萄糖苷(7)、(E)-5,4′-二羟基-二苯乙烯-3-O-(6-O-邻甲氧基苯甲酰基)-β-D-葡萄糖苷(8)、(E)-5,4′-二羟基-二苯乙烯-3-O-[(6-O-(3-甲氧基-4-羟基)苯甲酰基)]-β-D-葡萄糖苷(9)、(E)-5,4′-二羟基-二苯乙烯-3-O-(6-O-4-羟基苯甲酰基)-β-D-葡萄糖苷(10)、(+)lyoniresinol 3a-O-[6-(3,5-dimethoxy-4-hydroxy)-benzoyl]-β-D-glucopyranoside(11)、(+)peltogynolside(12)、(E)-5,4′-二羟基-二苯乙烯3-O-α-L-吡喃鼠李糖-(1→6)-β-D-吡喃葡萄糖苷(13)、(E)-5,4′-二羟基-二苯乙烯-3-O-[(6-O-(3,5-二甲氧基-4-羟基苯甲酰基)]-β-D-葡萄糖苷(14)、fernandoside(15)、mopanolside(16)。这些化合物中包括12个二苯乙烯苷,2个黄烷醇苷以及2个木脂素苷;其中化合物1~12为新化合物,化合物13~15为首次从本属植物中分离得到的已知化合物。
     药理活性测试结果表明化合物8~10、14~16具有一定的抗氧化活性,其中化合物9在10~(-4)M、10~(-5)M、10~(-6)M三个浓度下都具有良好的抗氧化作用,其活性强于阳性对照维生素E。
     对本属植物中获得的13个二苯乙烯苷类化合物进行(±)ESI-MS~n质谱裂解行为的研究。一方面,考察相同碰撞能条件下不同化合物的质谱裂解行为,发现在负离子检测模式下的ESI-MS~n对二苯乙烯苷类化合物具有较好的鉴别作用,它可以用于区别糖链部分为1→6连接或1→2连接的二苯乙烯苷,并对其裂解行为的差异作了较为合理的解释;另一方面,我们还考察了不同碰撞能条件下同一化合物的裂解行为的变化,从而保证所总结的裂解规律适用于LC-MS分析的条件;在此基础上,提出了鉴别二苯乙烯苷类化合物并确定糖链连接方式的分析方法,为快速鉴定该化合物提供依据。
     根据已总结的质谱裂解规律,通过HPLC/HRMS,HPLC-DAD/ESI-MS~n等在线结构分析方法,对短萼仪花中的微量成分进行了在线结构分析,获取了24个成分的结构信息,其中12个化合物指认为已分离鉴定的化合物,另外初步确定了12个化合物的结构,其中包括9个新化合物。新化合物结构分别为:(E)-白藜芦醇3-O-葡萄糖-(1→6)-葡萄糖苷(W2)、(E)-白藜芦醇3-O-葡萄糖-(1→2)-葡萄糖苷(W3)、(E)-5,4′-二羟基-二苯乙烯3-O-木糖-(1→2)-[鼠李糖-(1→6)]-葡萄糖苷(W5)、(E)-5,4′-二羟基-二苯乙烯3-O-木糖-(1→2)-鼠李糖苷(W10)、5,4′-二羟基-二苯基乙烷3-O-鼠李糖-(1→2)-葡萄糖苷(W12)、(E)-5,4′-二羟基-二苯乙烯3-O-木糖-(1→2)-木糖苷(W15)、(E)-5,4′-二羟基-3'-甲氧基-二苯乙烯3-O-鼠李糖-(1→2)-木糖苷(W21)、(Z)-5,4′-二羟基-二苯乙烯3-O-葡萄糖-(1→2)-木糖苷(W22)、(E)-5,4′-二羟基-二苯乙烯3-O-鼠李糖-(1→2)-鼠李糖苷(W23)。
     本文的研究结果表明基于活性筛选和化学筛选的天然产物研究方法,在一定程度上降低了传统天然产物研究方法的盲目性、重复性和耗时性,提高了发现新颖结构活性天然产物的几率和效率,为建立高效、快速、微量的天然产物研究方法奠定了基础并提供了较为成功的范例。
Lysidice brevicalyx Wei belongs to the genus Lysidice in the family Fabaceae.L. brevicalyx Wei is widely distributed in Guangdong,Guangxi,Yunnan,Guizhou Provinces etc.,in China,and its roots,barks and leafs can be used as Chinese traditional medicine with the main actions of detumescence,hemostasis and analgesia.
     A procedure based on biological and chemical screening was designed to investigate the novel bioactive constituents from the barks of Lysidice brevicalyx Wei.It was a significant attempt to obtain novel bioactive natural products efficiently and rapidly.
     Experimently,LC/UV and LC/ESI-MS~n was used as method for chemical screening of antioxidant fractions.The structure information of 53 constituents from four fractions was obtained,and 16 interesting unknown constituents were likely to be new compounds.
     According to the results of chemical screening,the 16 unknown constituents were isolated and their structures were established as(E)-5,4′-dihydroxystilbene 3-O-[β-D-xylopyranosyl-(1→6)]-β-D-glucopyranoside(1),(E)- 5,4′-dihydroxystilbene 3-O -[β-D-glucopyranosyl-(1→2)]-β-D-xylopyranoside(2),(E)-5,4′-dihydroxystilbene 3-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside(3),(Z)-5,4′-dihydroxy stilbene 3-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside(4),(Z)-5,4′- dihydroxystilbene 3-O-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside(5),(E)-5,4′-dihydroxystilbene 3-O-{α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]}-β-D-glucopyranoside (6),(Z)-5,4′-dihydroxystilbene 3-O-{α-L- rhamnopyranosyl-(1→2) -[α-L-rhamnopyranosyl-(1→6)]}-β-D-glucopyranoside(7),(E)-5,4′-dihydroxystilbene 3-O-[6-O-(2-methoxy)-benzoyl]-β-D-glucopyranoside(8),(E)-5,4′-dihydroxystilbene 3-O-[6-O-(3-methoxy-4-hydroxy)-benzoyl]-β-D- glucopyranoside(9),(E)-5,4′-dihydroxystilbene 3-O-[6-O-(4-hydroxyl)-benzoyl]-β- D-glucopyranoside(10),(+) lyoniresinol 3a-O-[6-(3,5-dimethoxy-4-hydroxy)- benzoyl]-β-D-glucopyranoside(11), (+)peltogynolside(12),(E)-5,4′-dihydroxy- stilbene 3-O-[α-L-rhamnopyranosyl-(1→6)] -β-D-glucopyranoside(13),(E)-5,4′-dihydroxystilbene 3-O-[6-O-(3,5- dimethoxy-4 -hydroxy)-benzoyl]-β-D-glucopyranoside(14),(+)lyoniresinol 3a-O-[6-(3-methoxy-4 -hydroxy)-benzoyl]-β-D-glucopyranoside(15),mopanolside(16).Among them,1-12 are new compounds,and 13-15 were isolated from the plants of this genus for the first time.
     Antioxidant activities of the isolated compounds were investigated.Compounds 8~10,14~16 exhibited obvious antioxidant effect,and especially,compound 9 was proved to be active at low,middle and high concentrations,which was stronger than those of the positive control agent vitamin E.
     The(+)ESI-MS~n fragmentation behaviors of thirteen stilbene glycosides isolated from the genus Lysidice were investigated.The characteristic fragmentation patterns of the compounds were discussed in detail to give some valuable conclusions.On the basis of above conclusions,the fraction including trace constituents with similar structures was investigated by HPLC/HR-MS,HPLC-DAD/ESI-MS~n analyses.As a result,the possible structures of 24 trace constituents were deduced,in which 12 ones have been obtained or identified previously in our investigation,while other 9 compounds were identified as new ones.
     Through the procedure based on Biological and chemical screening,the time-consuming isolation of common natural products might be avoided and the hit of success in discovering new and/or bioactive compounds might be increased dramatically.
引文
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