柳叶五层龙正丁醇提取部分中的3个新酚性成分及其α-葡萄糖苷酶抑制活性
|
摘要
采用多种色谱分离方法从柳叶五层龙(Salacia cochinchinensis Lour)的茎叶中分离得到5个化合物.通过一维(1D)及二维核磁共振波谱(2D NMR),包括核磁共振氢谱(1H NMR)、核磁共振碳谱(13C NMR)、异核单量子相关(HSQC)、异核多键相关(HMBC)、氢氢相关(1H-1H COSY)和旋转坐标中的欧沃豪斯增强光谱(ROESY),以及红外光谱(IR)和电喷雾电离高分辨质谱(ESI-HRMS)等方法,鉴定其结构分别为Salaciaco-chinoside A (1),5'-O-3,4,5-trimethoxybenzoyl-β-D-apiofuranoside (2),5-methoxy-anticerol A (3),21α,30-dihydroxy-D∶A-friedooleanan-3-one(4)和21α,26-dihydroxyfriedelan-3-one(5).化合物1～3为新化合物.α-葡萄糖苷酶抑制活性测试结果显示,化合物1和3对α-葡萄糖苷酶具有显著的抑制作用,其IC50值分别为0. 32和0. 59μmol/L;化合物2,4和5未表现出α-葡萄糖苷酶抑制活性.
Five compounds were isolated from the stems and leaves of Salacia cochinchinensis Lour. By comprehensive spectroscopic analyses including mass spectroscopy( MS),infrared radiation( IR),1 D and 2 D nuclear magnetic resonance( NMR) [heteronuclear single quantum coherence( HSQC),heteronuclear multiple bond correlation( HMBC),1 H-1 H chemical-shift correlation spectroscopy(1 H-1 H COSY) and rotating frame overhauser effect spectroscopy( ROESY) ],their structures were elucidated as Salaciacochinoside A( 1),5'-O-3,4,5-trimethoxybenzoyl-β-D-apiofuranoside( 2),5-methoxy-anticerol A( 3),21α,30-dihydroxy-D ∶A-friedooleanan-3-one( 4) and 21α,26-dihydroxyfriedelan-3-one( 5),respectively. Compounds 1—3 were new compounds. All the compounds were assayed for the anti-diabetic activities. Compounds 1 and 3 exhibited remarkable bioactivity,inhibiting α-glucosidase with IC50 values of 0. 32 and 0. 59 μmol/L,respectively.Compounds 2,4 and 5 showed none anti-diabetic activity in current experiment.
Five compounds were isolated from the stems and leaves of Salacia cochinchinensis Lour. By comprehensive spectroscopic analyses including mass spectroscopy( MS),infrared radiation( IR),1 D and 2 D nuclear magnetic resonance( NMR) [heteronuclear single quantum coherence( HSQC),heteronuclear multiple bond correlation( HMBC),1 H-1 H chemical-shift correlation spectroscopy(1 H-1 H COSY) and rotating frame overhauser effect spectroscopy( ROESY) ],their structures were elucidated as Salaciacochinoside A( 1),5'-O-3,4,5-trimethoxybenzoyl-β-D-apiofuranoside( 2),5-methoxy-anticerol A( 3),21α,30-dihydroxy-D ∶A-friedooleanan-3-one( 4) and 21α,26-dihydroxyfriedelan-3-one( 5),respectively. Compounds 1—3 were new compounds. All the compounds were assayed for the anti-diabetic activities. Compounds 1 and 3 exhibited remarkable bioactivity,inhibiting α-glucosidase with IC50 values of 0. 32 and 0. 59 μmol/L,respectively.Compounds 2,4 and 5 showed none anti-diabetic activity in current experiment.
引文
[1] Li L.,Zou J. Y.,Xia Q.,Cui H. M.,You S. Y.,Liu Y. X.,Wang Q. M.,Chem. Res. Chinese Universities,2018,34(5),697—699
[2] Liu Y.,Li X. W.,Zhang H. Q.,Wu Q.,Shi X. L.,Jin Y. R.,Chem. Res. Chinese Universities,2018,34(3),382—388
[3] Editorial Committee of Flora of China,Chinese Academy of Sciences,Flora of China,Science Press,Beijing,1981,46,1—4(中国科学院中国植物志编辑委员会.中国植物志,北京:科学出版社,1981,46,1—4)
[4] Tezuka Y.,Kikuchi T.,Dhanabalasingham B.,Karunaratne V.,Gunatilaka A. A. L.,Nat. Prod. Lett.,1993,3(4),273—276
[5] Setzer W. N.,Holland M. T.,Bozeman C. A.,Rozmus G. F.,Setzer M. C.,Moriarity D. M.,Reeb S.,Vogler B.,Bates R. B.,HaberW. A.,Planta Med.,2001,67(1),65—69
[6] Duarte L. P.,Figueiredo R. C.,Sousa G. F.,Silva Soares D. B. D.,Rodrigues S. B. V.,Fatima Silva F. C. S. G. D.,Quim. Nova,2010,33(4),900—903
[7] Agius B. R.,Vogler B.,Stokes S. L.,Setzer W. N.,Nat. Prod. Commun.,2007,2(11),1083—1084
[8] Gunatilaka A. A. L.,Dhanabalasingham B.,Karunaratne V.,Kikuchi T.,Tezuka Y.,Tetrahedron,1993,49(45),10397—10404
[9] Pu J.,Feng F.,Guo Q. L.,Xie N.,Chin. J. Modern Appl. Pharm.,2009,26(11),916—918(濮江,冯锋,郭青龙,谢宁.中国现代应用药学,2009,26(11),916—918)
[10] Guo Z. H.,Xi R. G.,Wang X. B.,Wu L. J.,Gao H. Y.,Acta Pharm. Sin.,2009,44(10),1123—1126(郭正红,袭荣刚,王晓波,吴立军,高慧媛.药学学报,2009,44(10),1123—1126)
[11] Zhang Y.,Nakamura S.,Wang T.,Matsuda H.,Yoshikawa M.,Tetrahedron,2008,64(30/31),7347—7352
[12] Gao H. Y.,Guo Z. H.,Cheng P.,Xu X. M.,Wu L. J.,J. Asi. Nat. Prod. Res.,2010,12(10),834—842
[13] Kishi A.,Morikawa T.,Matsuda H.,Yoshikawa M.,Chem. Pharm. Bull.,2003,51(9),1051—1055
[14] Hisham A.,Kumar G. J.,Fujimoto Y.,Hara N.,Phytochem.,1995,40(4),1227—1231
[15] Subhadhirasakul S.,Keawpradub N.,Promwong C.,Yuenyongsawad S.,Nat. Prod. Commun.,2008,3(2),211—214
[16] Morikawa T.,Kishi A.,Pongpiriyadacha Y.,Matsuda H.,Yoshikawa M.,J. Nat. Prod.,2003,66(9),1191—1196
[17] Dhanabalasingham B.,Karunaratne V.,Tezuka Y.,Kikuchi T.,Gunatilaka A. A. L.,Phytochem.,1996,42(5),1377—1385
[18] Hisham A.,Jayakumar G.,Fujimoto Y.,Hara N.,Phytochem.,1996,43(4),843—845
[19] Kumar V.,Wijeratne D. B. T.,Abeygunawardena C.,Phytochem.,1990,29(1),333—335
[20] Matsuda H.,Murakami T.,Yashiro K.,Yamahara J.,Yoshikawa M.,Chem. Pharm. Bull.,1999,47(12),1725—1729
[21] Zhang Y.,Nakamura S.,Pongpiriyadacha Y.,Matsuda H.,Yoshikawa M.,Chem. Pharm. Bull.,2008,56(4),547—553
[22] Nakamura S.,Zhang Y.,Wang T.,Heterocycles,2008,75(6),1435—1446
[23] Yoshikawa M.,Xu F.,Nakamura S.,Wang T.,Matsuda H.,Tanabe G.,Muraoka O.,Heterocycles,2008,75(6),1397—1405
[24] Ma C. M.,Hattori M.,Daneshtalab M.,Wang L. L.,J. Med. Chem.,2008,51,6188—6194
[25] Ouyang M. A.,Kuo Y. H.,J. Asi. Nat. Prod. Res.,2006,8(7),625—630
[26] Suo M.,Isao H.,Kato H.,Takano F.,Ohta T.,Fitoterapia,2012,83(8),1484—1488
[27] Li X. S.,Zhu J. J.,Zhao H.,Li S. L.,Hao X. J.,Yao X. S.,Tang J. S.,Phytochem. Lett.,2015,13,182—186
[2] Liu Y.,Li X. W.,Zhang H. Q.,Wu Q.,Shi X. L.,Jin Y. R.,Chem. Res. Chinese Universities,2018,34(3),382—388
[3] Editorial Committee of Flora of China,Chinese Academy of Sciences,Flora of China,Science Press,Beijing,1981,46,1—4(中国科学院中国植物志编辑委员会.中国植物志,北京:科学出版社,1981,46,1—4)
[4] Tezuka Y.,Kikuchi T.,Dhanabalasingham B.,Karunaratne V.,Gunatilaka A. A. L.,Nat. Prod. Lett.,1993,3(4),273—276
[5] Setzer W. N.,Holland M. T.,Bozeman C. A.,Rozmus G. F.,Setzer M. C.,Moriarity D. M.,Reeb S.,Vogler B.,Bates R. B.,HaberW. A.,Planta Med.,2001,67(1),65—69
[6] Duarte L. P.,Figueiredo R. C.,Sousa G. F.,Silva Soares D. B. D.,Rodrigues S. B. V.,Fatima Silva F. C. S. G. D.,Quim. Nova,2010,33(4),900—903
[7] Agius B. R.,Vogler B.,Stokes S. L.,Setzer W. N.,Nat. Prod. Commun.,2007,2(11),1083—1084
[8] Gunatilaka A. A. L.,Dhanabalasingham B.,Karunaratne V.,Kikuchi T.,Tezuka Y.,Tetrahedron,1993,49(45),10397—10404
[9] Pu J.,Feng F.,Guo Q. L.,Xie N.,Chin. J. Modern Appl. Pharm.,2009,26(11),916—918(濮江,冯锋,郭青龙,谢宁.中国现代应用药学,2009,26(11),916—918)
[10] Guo Z. H.,Xi R. G.,Wang X. B.,Wu L. J.,Gao H. Y.,Acta Pharm. Sin.,2009,44(10),1123—1126(郭正红,袭荣刚,王晓波,吴立军,高慧媛.药学学报,2009,44(10),1123—1126)
[11] Zhang Y.,Nakamura S.,Wang T.,Matsuda H.,Yoshikawa M.,Tetrahedron,2008,64(30/31),7347—7352
[12] Gao H. Y.,Guo Z. H.,Cheng P.,Xu X. M.,Wu L. J.,J. Asi. Nat. Prod. Res.,2010,12(10),834—842
[13] Kishi A.,Morikawa T.,Matsuda H.,Yoshikawa M.,Chem. Pharm. Bull.,2003,51(9),1051—1055
[14] Hisham A.,Kumar G. J.,Fujimoto Y.,Hara N.,Phytochem.,1995,40(4),1227—1231
[15] Subhadhirasakul S.,Keawpradub N.,Promwong C.,Yuenyongsawad S.,Nat. Prod. Commun.,2008,3(2),211—214
[16] Morikawa T.,Kishi A.,Pongpiriyadacha Y.,Matsuda H.,Yoshikawa M.,J. Nat. Prod.,2003,66(9),1191—1196
[17] Dhanabalasingham B.,Karunaratne V.,Tezuka Y.,Kikuchi T.,Gunatilaka A. A. L.,Phytochem.,1996,42(5),1377—1385
[18] Hisham A.,Jayakumar G.,Fujimoto Y.,Hara N.,Phytochem.,1996,43(4),843—845
[19] Kumar V.,Wijeratne D. B. T.,Abeygunawardena C.,Phytochem.,1990,29(1),333—335
[20] Matsuda H.,Murakami T.,Yashiro K.,Yamahara J.,Yoshikawa M.,Chem. Pharm. Bull.,1999,47(12),1725—1729
[21] Zhang Y.,Nakamura S.,Pongpiriyadacha Y.,Matsuda H.,Yoshikawa M.,Chem. Pharm. Bull.,2008,56(4),547—553
[22] Nakamura S.,Zhang Y.,Wang T.,Heterocycles,2008,75(6),1435—1446
[23] Yoshikawa M.,Xu F.,Nakamura S.,Wang T.,Matsuda H.,Tanabe G.,Muraoka O.,Heterocycles,2008,75(6),1397—1405
[24] Ma C. M.,Hattori M.,Daneshtalab M.,Wang L. L.,J. Med. Chem.,2008,51,6188—6194
[25] Ouyang M. A.,Kuo Y. H.,J. Asi. Nat. Prod. Res.,2006,8(7),625—630
[26] Suo M.,Isao H.,Kato H.,Takano F.,Ohta T.,Fitoterapia,2012,83(8),1484—1488
[27] Li X. S.,Zhu J. J.,Zhao H.,Li S. L.,Hao X. J.,Yao X. S.,Tang J. S.,Phytochem. Lett.,2015,13,182—186