印度黄檀化学成分分离及结构鉴定
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摘要
目的印度黄檀主要化学成分的分离、纯化及结构鉴定。方法采用硅胶柱、C_(18)反相硅胶柱、萃取、重结晶等分离、纯化方法对印度黄檀的石油醚、三氯甲烷、乙酸乙酯部位进行分离、纯化,所得化合物通过理化、NMR及高效液相串联三重四级杆质谱仪(HPLC-QQQ-MS/MS)波谱数据鉴定结构。结果石油醚部位分离得到dalbergiphenol;三氯甲烷部位分离得到4-methoxydalbergione、O-methyldalbergin和dalbergin;乙酸乙酯部位分离纯化得到3,4,6-trihydroxy-7-methoxyflavanone、plathymenin和biochanin A。结论从印度黄檀中分离得到7种化合物,均为黄酮类化合物,为其进一步单体药效作用研究提供了良好的材料和研究基础。
Objective To isolate and purify the main chemical components of Dalbergia sissoo Roxb. Methods The compounds were isolated and purified by silica gel column,C_(18) reverse phase silica gel column,extraction method and recrystallization method from petroleum ether,chloroform and ethyl acetate parts of Dalbergia sissoo Roxb. The structures of the compounds were identified by physicochemical properties,NMR and HPLC-QQQ-MS/MS spectral data. Results Dalbergiphenol was isolated from petroleum ether part. 4-Methoxydalbergione,O-methyldalbergin and dalbergin were obtained from chloroform part; 3,4,6-trihydroxy-7-methoxyflavanone,plathymenin and biochanin A were obtained from ethyl acetate part. Conclusion All the seven compounds which have been separated from Dalbergia sissoo Roxb. are flavonoids. It provides a good foundation and material for further research on monomer efficacy.
Objective To isolate and purify the main chemical components of Dalbergia sissoo Roxb. Methods The compounds were isolated and purified by silica gel column,C_(18) reverse phase silica gel column,extraction method and recrystallization method from petroleum ether,chloroform and ethyl acetate parts of Dalbergia sissoo Roxb. The structures of the compounds were identified by physicochemical properties,NMR and HPLC-QQQ-MS/MS spectral data. Results Dalbergiphenol was isolated from petroleum ether part. 4-Methoxydalbergione,O-methyldalbergin and dalbergin were obtained from chloroform part; 3,4,6-trihydroxy-7-methoxyflavanone,plathymenin and biochanin A were obtained from ethyl acetate part. Conclusion All the seven compounds which have been separated from Dalbergia sissoo Roxb. are flavonoids. It provides a good foundation and material for further research on monomer efficacy.
引文
[1] 国家药典委员会.中华人民共和国药典:2015年版一部[M].北京:中国医药科技出版社,2015:229.
[2] 傅立国.中国植物红皮书.稀有濒危植物:1册[M].北京:科学出版社,1992:376.
[3] 马文辉,钟琼芯,符永登.海南省珍惜濒危植物和重点保护野生植物[J].海南师范学院学报(自然科学版),2003,16(4):68-71.
[4] TEWARI D N. A monograph on Dalbergia sissoo Roxb.[M]. Dehradu:International Book Distributors,1994:1-9.
[5] 中药商品知识编写组.中药商品知识:中册[M].广州:广东科技出版社,1989:157.
[6] 石雷,梁英扬,邓疆.印度黄檀引种试验研究[J].西南农业学报,2010,23(2):559-559.
[7] 林励,徐鸿华,肖省娥,等.不同品种降香质量研究[J].中药材,1997,20(7):366-370.
[8] 肖省娥,林励.不同来源的降香药材中总黄酮含量测定[J].基层中药杂志,2000,14(6):12-14.
[9] 范竹鸣,王佑华,谢瑞芳,等.降香化学成分和药理作用研究进展[J].时珍国医国药,2016,27(10):2478-2480.
[10] 杨志宏,梅超,何雪辉,等.降香化学成分、药理作用及药代特征的研究进展[J].中国中药杂志,2013,38(11):1679-1683.
[11] 王昊,梅文莉,郭志凯,等.降香的化学成分研究[J].中国中药杂志,2014,39(9):1625-1630.
[12] WANG H,MEI W L,YANG D L,et al. Phenolic compounds from the heart wood of Dalbergia odorifera T.Chen[J]. Nat Prod Res Dev,2014,26(6):856-859.
[13] KAWAII S,TOMONOY,KATASE E,et al. Effect of coumarins on HL-60 cell differentitation[J]. Anticancer Res,2000,20(4):2505-2512.
[14] 朱亮,冷红文,谭力伟,等.降香挥发油对血栓形成、血小板 cAMP 和血浆纤溶酶活性的影响[J].中成药,1992,14(4):30.
[15] 訾慧,沙明.中药降香研究进展[J].辽宁中医学院学报,2003,5(2):90-91.
[16] CHAN S C,CHANG Y S,WANG J P,et al.Three new flavonoids and antiallergic,anti-inflammatory constituents from the heartwood of Dalbergia odorifer[J]. Planta Med,1998,64(2):153-158.
[17] PARK K R,YUN H M,QUANG T H,et al. 4-methoxydalbergion suppresses growth and induces apoptosis in human osteosarcoma cells in vitro and in vivo xenograft odel through down-regulation of the JAK2/STAT3 pathway[J].Oncotarget,2016,7(6):6960-6971.
[18] MUANGNOICHAROEN N,FRAHM A W. Neoflavanoids of Dalbergia parviflora[J]. Phytochemistry,1982,21(3):767-772.
[19] BISSEL P,NAZIH A,SABLONG R,et al. Stereoselective synthesis of (R)- and (S)-4-methoxydalbergione via asymmetric catalytic hydrogenation[J]. Org Lett,1999,1(8):1283-1285.
[20] YAMAMOTO Y,KIRAI N. Synthesis of 4-arylcoumarins via Cu-catalyzed hydroarylation with arylboronic acids[J]. Org Lett,2008,10(24):5513-5516.
[21] SHRESTHA S P,NARUKAWA Y J,TAKEDA T,et al. Chemical constituents of Nepalese propolis:isolation of new dalbergiones and related compounds[J]. J Nat Med,2007,61(1):73-76.
[22] SHRESTHA S P,AMANO Y,NARUKAWA Y,et al. Takeda. Nitric oxide production inhibitory activity of flavonoids contained in trunk exudates of Dalbergia sissoo[J]. J Nat Prod,2008,71(1):98-101.
[23] 李然,林励,祁龙凯,等.HPLC法测定印度黄檀中黄檀素等3种成分含量[J].广东药学院学报,2016,32(1):51-54.
[2] 傅立国.中国植物红皮书.稀有濒危植物:1册[M].北京:科学出版社,1992:376.
[3] 马文辉,钟琼芯,符永登.海南省珍惜濒危植物和重点保护野生植物[J].海南师范学院学报(自然科学版),2003,16(4):68-71.
[4] TEWARI D N. A monograph on Dalbergia sissoo Roxb.[M]. Dehradu:International Book Distributors,1994:1-9.
[5] 中药商品知识编写组.中药商品知识:中册[M].广州:广东科技出版社,1989:157.
[6] 石雷,梁英扬,邓疆.印度黄檀引种试验研究[J].西南农业学报,2010,23(2):559-559.
[7] 林励,徐鸿华,肖省娥,等.不同品种降香质量研究[J].中药材,1997,20(7):366-370.
[8] 肖省娥,林励.不同来源的降香药材中总黄酮含量测定[J].基层中药杂志,2000,14(6):12-14.
[9] 范竹鸣,王佑华,谢瑞芳,等.降香化学成分和药理作用研究进展[J].时珍国医国药,2016,27(10):2478-2480.
[10] 杨志宏,梅超,何雪辉,等.降香化学成分、药理作用及药代特征的研究进展[J].中国中药杂志,2013,38(11):1679-1683.
[11] 王昊,梅文莉,郭志凯,等.降香的化学成分研究[J].中国中药杂志,2014,39(9):1625-1630.
[12] WANG H,MEI W L,YANG D L,et al. Phenolic compounds from the heart wood of Dalbergia odorifera T.Chen[J]. Nat Prod Res Dev,2014,26(6):856-859.
[13] KAWAII S,TOMONOY,KATASE E,et al. Effect of coumarins on HL-60 cell differentitation[J]. Anticancer Res,2000,20(4):2505-2512.
[14] 朱亮,冷红文,谭力伟,等.降香挥发油对血栓形成、血小板 cAMP 和血浆纤溶酶活性的影响[J].中成药,1992,14(4):30.
[15] 訾慧,沙明.中药降香研究进展[J].辽宁中医学院学报,2003,5(2):90-91.
[16] CHAN S C,CHANG Y S,WANG J P,et al.Three new flavonoids and antiallergic,anti-inflammatory constituents from the heartwood of Dalbergia odorifer[J]. Planta Med,1998,64(2):153-158.
[17] PARK K R,YUN H M,QUANG T H,et al. 4-methoxydalbergion suppresses growth and induces apoptosis in human osteosarcoma cells in vitro and in vivo xenograft odel through down-regulation of the JAK2/STAT3 pathway[J].Oncotarget,2016,7(6):6960-6971.
[18] MUANGNOICHAROEN N,FRAHM A W. Neoflavanoids of Dalbergia parviflora[J]. Phytochemistry,1982,21(3):767-772.
[19] BISSEL P,NAZIH A,SABLONG R,et al. Stereoselective synthesis of (R)- and (S)-4-methoxydalbergione via asymmetric catalytic hydrogenation[J]. Org Lett,1999,1(8):1283-1285.
[20] YAMAMOTO Y,KIRAI N. Synthesis of 4-arylcoumarins via Cu-catalyzed hydroarylation with arylboronic acids[J]. Org Lett,2008,10(24):5513-5516.
[21] SHRESTHA S P,NARUKAWA Y J,TAKEDA T,et al. Chemical constituents of Nepalese propolis:isolation of new dalbergiones and related compounds[J]. J Nat Med,2007,61(1):73-76.
[22] SHRESTHA S P,AMANO Y,NARUKAWA Y,et al. Takeda. Nitric oxide production inhibitory activity of flavonoids contained in trunk exudates of Dalbergia sissoo[J]. J Nat Prod,2008,71(1):98-101.
[23] 李然,林励,祁龙凯,等.HPLC法测定印度黄檀中黄檀素等3种成分含量[J].广东药学院学报,2016,32(1):51-54.