Synthesis and insecticidal activity of novel hydrazone compounds derived from a naturally occurring lignan podophyllotoxin against Mythimna separata (Walker)

被引:25
作者
Wang, Yi [1 ,2 ]
Yu, Xiang [1 ]
Zhi, Xiaoyan [1 ]
Xiao, Xiao [1 ]
Yang, Chun [1 ]
Xu, Hui [1 ]
机构
[1] Northwest A&F Univ, Coll Sci, Lab Pharmaceut Design & Synth, Yangling 712100, Shaanxi Provinc, Peoples R China
[2] Shanxi Agr Univ, Coll Agr, Taigu 030801, Shanxi Province, Peoples R China
基金
中国国家自然科学基金;
关键词
Podophyllotoxin; Insecticidal activity; Botanical insecticide; Structural modification; Mythimna separata Walker; ACTIVITY-RELATIONSHIP QSAR; BIOLOGICAL-ACTIVITIES; ANTIFUNGAL ACTIVITY; DERIVATIVES; SEMISYNTHESIS; BIOSYNTHESIS; COMPONENTS; MODE;
D O I
10.1016/j.bmcl.2014.04.074
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, a series of novel hydrazone derivatives of podophyllotoxin, which is a naturally occurring aryltetralin lignan and isolated as the main secondary metabolite from the roots and rhizomes of Podophyllum species, were synthesized and evaluated as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. Especially compounds 8i, 8j, 8t, and 8u showed the more potent insecticidal activity with the final mortality rates greater than 60%. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2621 / 2624
页数:4
相关论文
共 29 条
[1]   Anti-mycobacterial natural products from the Canadian medicinal plant Juniperus communis [J].
Carpenter, Caitlyn D. ;
O'Neill, Taryn ;
Picot, Nadia ;
Johnson, John A. ;
Robichaud, Gilles A. ;
Webster, Duncan ;
Gray, Christopher A. .
JOURNAL OF ETHNOPHARMACOLOGY, 2012, 143 (02) :695-700
[2]   Insight into dihalogenation of E-ring of podophyllotoxins, and their acyloxyation derivatives at the C4 position as insecticidal agents [J].
Che, Zhiping ;
Yu, Xiang ;
Fan, Lingling ;
Xu, Hui .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (20) :5592-5598
[3]   Isolation and Identification of Secondary Metabolites of Clitocybe nuda Responsible for Inhibition of Zoospore Germination of Phytophthora capsici [J].
Chen, Jin-Tong ;
Su, Huey-Jen ;
Huang, Jenn-Wen .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (30) :7341-7344
[4]   Natural products in crop protection [J].
Dayan, Franck E. ;
Cantrell, Charles L. ;
Duke, Stephen O. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (12) :4022-4034
[5]   Isolation, Characterization and Antifungal Activity of Major Constituents of the Himalayan Lichen Parmelia reticulata Tayl. [J].
Goel, Mayurika ;
Dureja, Prem ;
Rani, Archna ;
Uniyal, Prem L. ;
Laatsch, Hartmut .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2011, 59 (06) :2299-2307
[6]   Podophyllotoxin:: distribution, sources, applications and new cytotoxic derivatives [J].
Gordaliza, M ;
García, PA ;
del Corral, JMM ;
Castro, MA ;
Gómez-Zurita, MA .
TOXICON, 2004, 44 (04) :441-459
[7]   Regioselective synthesis of fraxinellone-based hydrazone derivatives as insecticidal agents [J].
Guo, Yong ;
Yan, Yuan-Yuan ;
Yang, Chun ;
Yu, Xiang ;
Zhi, Xiao-Yan ;
Xu, Hui .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (17) :5384-5387
[8]   Synthesis and Insecticidal Activity of Some Novel Fraxinellone-Based Esters [J].
Guo, Yong ;
Yan, Yuanyuan ;
Yu, Xiang ;
Wang, Yi ;
Zhi, Xiao-Yan ;
Hu, Ying ;
Xu, Hui .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (28) :7016-7021
[9]   Insecticide Resistance After Silent Spring [J].
Heckel, David G. .
SCIENCE, 2012, 337 (6102) :1613-1614
[10]  
INAMORI Y, 1986, CHEM PHARM BULL, V34, P2542