Sesquiterpenoids, alantolactone analogues, and seco-guaiene from the roots of Inula helenium

被引:42
作者
Jiang, Hai-Long [1 ]
Chen, Jia [1 ]
Jin, Xiao-Jie [1 ]
Yang, Jun-Li [1 ]
Li, Ya [1 ]
Yao, Xiao-Jun [1 ]
Wu, Quan-Xiang [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China
关键词
Inula helenium; Dimeric eudesmanolide; Nor-eudesmanolide; seco-Guaiene; Anti-bacterial activity; OCCURRING TERPENE DERIVATIVES; VIRGAUREA SPP. OLIGOCEPHALA; EUPATORIUM-QUADRANGULARAE; CIRCULAR-DICHROISM; LACTONES; EUDESMANOLIDES; CONFORMATION; RACEMOSA; ENZYME;
D O I
10.1016/j.tet.2011.09.070
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three new sesquiterpenoids, a new unusual dimeric eudesmanolide, bialantolactone, a new nor-eudesmanolide, trinoralantolactone, and a new seco-guaiene, 7S,1(10)Z-4,5-seco-guaia-1(10),11-diene-4,5-dioxo, together with 13 known sesquiterpenoids, were isolated from the roots of Inula helenium. Their structures were elucidated by comprehensive spectroscopic analyses. The absolute configurations of bialantolactone and 75,1(10)Z-4,5-seco-guaia-1(10),11-diene-4,5-dioxo were defined via the experimental and computational optical rotation and CD data. The plausible biosynthetic pathways to bialantolactone and 7S,1(10)Z-4,5-seco-guaia-1(10),11-diene-4,5-dioxo are discussed. 16 compounds were evaluated for their anti-bacterial activities against six bacteria. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9193 / 9198
页数:6
相关论文
共 39 条
[1]   ISOLATION OF 2 SESQUITERPENES FROM PLUCHEA-ARGUTA [J].
AHMAD, VU ;
FIZZA, K ;
SULTANA, A .
PHYTOCHEMISTRY, 1989, 28 (11) :3081-3083
[2]   Oxygenated terpenoids from a Formosan soft coral Sinularia gibberosa [J].
Ahmed, AF ;
Kuo, YH ;
Dai, CF ;
Sheu, JH .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (08) :1208-1212
[3]   THE STRUCTURE AND CONFORMATION OF UMBELLIFOLIDE, A 4,5-SECOEUDESMANE DERIVATIVE [J].
APPENDINO, G ;
GARIBOLDI, P ;
CALLERI, M ;
CHIARI, G ;
VITERBO, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (11) :2705-2709
[4]  
Berova N., 2000, CIRCULAR DICHROISM P, V2nd, P337
[5]   Application of electronic circular dichroism in configurational and conformational analysis of organic compounds [J].
Berova, Nina ;
Di Bari, Lorenzo ;
Pescitelli, Gennaro .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (06) :914-931
[6]   NATURALLY OCCURRING TERPENE DERIVATIVES .142. NEW SESQUITERPENE LACTONES FROM INULA SPECIES [J].
BOHLMANN, F ;
MAHANTA, PK ;
JAKUPOVIC, J ;
RASTOGI, RC ;
NATU, AA .
PHYTOCHEMISTRY, 1978, 17 (07) :1165-1172
[7]   NATURALLY OCCURRING TERPENE DERIVATIVES .172. NEW GERMACRANOLIDE FROM MUNNOZIA-MARONII [J].
BOHLMANN, F ;
GRENZ, M .
PHYTOCHEMISTRY, 1979, 18 (02) :334-335
[8]   Antimycobacterial eudesmanolides from Inula helenium and Rudbeckia subtomentosa [J].
Cantrell, CL ;
Abate, L ;
Fronczek, FR ;
Franzblau, SG ;
Quijano, L ;
Fischer, NH .
PLANTA MEDICA, 1999, 65 (04) :351-355
[9]  
CHEVALLIER A, 2001, ENCY MED PLANTS, P109
[10]   Antimicrobial activity of Inula helenium L. essential oil against Gram-positive and Gram-negative bacteria and Candida spp. [J].
Deriu, Antonella ;
Zanetti, Stefania ;
Sechi, Leonardo A. ;
Marongiu, Bruno ;
Piras, Alessandra ;
Porcedda, Silvia ;
Tuveri, Enrica .
INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS, 2008, 31 (06) :588-590