Identification of new pyrrole alkaloids from the fruits of Lycium chinense

被引：0
作者：
Ui Joung Youn
Joo Yun Lee
Yun-Seo Kil
Ah-Reum Han
Chong Hak Chae
Shi Yong Ryu
Eun-Kyoung Seo
机构：
[1] Ewha Womans University,Graduate School of Pharmaceutical Sciences, College of Pharmacy
[2] Korea Research Institute of Chemical Technology,Drug Discovery Platform Technology Team
来源：
Archives of Pharmacal Research | 2016年 / 39卷
关键词：
Solanaceae; Pyrrole alkaloid; ECD; Absolute configuration;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Three new minor pyrrole alkaloids, 3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]pentanedioic acid (1), (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-1-methoxy-1-oxobutanoic acid (2), and methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate (3) were isolated from the fruits of Lycium chinense Miller (Solanaceae), along with the known compound, methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(phenyl)propanoate (4). The structures of 1–4 were elucidated by analysis of their 1D- and 2D-NMR and HRMS data. The absolute configurations of 2–4, possessing a stereogenic center in each structure, were determined by comparison of their experimental electronic circular dichroism (ECD) with those of calculated ECD values.
引用
收藏
页码：321 / 327
页数：6
相关论文
共 81 条
[1]  
Amos RIJ(2005)Annulation of pyrrole: application to the synthesis of indolizidine alkaloids Tetrahedron 61 8226-8230
[2]  
Gourlay BS(1998)Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model J Phys Chem A 102 1995-2001
[3]  
Molesworth PP(1983)1,4-Dichloro-1,4-dimethoxybutane as a mild reagent for the conversion of primary amines to pyrroles. Synthesis of a pyrrole compound from tobacco J Org Chem 48 3059-3061
[4]  
Smith JA(1991)Short, enantiogenic syntheses of (−)-indolizidine 167B and (+)-monomorine J Am Chem Soc 113 3513-3518
[5]  
Sprod OR(2003)Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model J Comput Chem 24 669-681
[6]  
Barone V(2000)A facile synthesis of polysubstituted pyrroles Org Lett 2 2283-2286
[7]  
Cossi MJ(1999)A general synthesis of 2-formyl-3-arylpyrroles Tetrahedron Lett 40 4555-4558
[8]  
Chan TH(1995)Amino acid-pyrrole J Photochem Photobiol B 30 195-200
[9]  
Lee SD(1995)-conjugates; a new class of antioxidants II. Effectiveness of singlet oxygen quenching by luminescence measurements Helv Chim Acta 78 1511-1524
[10]  
Charles WJ(1962)Short, enantiospecific syntheses of indolizidines 209B and 209D, and piclavine A from diethyl-L-glutamate J Org Chem 27 2466-2470
123456789