|
|
|
|
|
| Synthesis and Insecticidal Activity of Novel Camptothecin Derivatives Containing Analogs of Chrysanthemic Acid Moieties |
| DENG Li, ZHANG Lan, CAO Li-dong, XIE Ru-liang, ZHANG Yan-ning, HE Wei-zhi , JIANG Hong-yun |
| State Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, P.R.China |
|
|
|
摘要 Creating high-efficient and environment-friendly pesticides is very important to produce the pollution free agriculture food and maintain the balance of the survival environmental of the human being. According to reports, camptothecin (CPT) and its derivatives are now being explored as a class of botanical insecticide in agriculture due to its novel mode of action. In order to improve the insecticidal activity of CPT, ten novel camptothecin (1) and 10-hydroxycamptothecin (2) derivatives (1a, 1b, 1c, 1d, 1e; 2a, 2b, 2c, 2d, 2e) were designed and synthesized via esterification with analogs of chrysanthemic acid, which have outstanding insecticidal activity. The results showed that compound 2a exhibited potent antifeeding effect and the best contact toxicity among the target compounds against the third-instar larvae of beet armyworm, Spodoptera exigua Hübner. Compound 2a was also found to be the most effective cytotoxic compound to the tested insect cell lines, IOZCAS-Spex-II, which were established from the fat bodies of S. exigua. It was proposed that the 10-hydroxyl group in the camptothecin derivatives is a key factor for the antifeeding activity of a compound. The nature of the substituents was considered the major factor in determining the insecticidal activity of these compounds.
Abstract Creating high-efficient and environment-friendly pesticides is very important to produce the pollution free agriculture food and maintain the balance of the survival environmental of the human being. According to reports, camptothecin (CPT) and its derivatives are now being explored as a class of botanical insecticide in agriculture due to its novel mode of action. In order to improve the insecticidal activity of CPT, ten novel camptothecin (1) and 10-hydroxycamptothecin (2) derivatives (1a, 1b, 1c, 1d, 1e; 2a, 2b, 2c, 2d, 2e) were designed and synthesized via esterification with analogs of chrysanthemic acid, which have outstanding insecticidal activity. The results showed that compound 2a exhibited potent antifeeding effect and the best contact toxicity among the target compounds against the third-instar larvae of beet armyworm, Spodoptera exigua Hübner. Compound 2a was also found to be the most effective cytotoxic compound to the tested insect cell lines, IOZCAS-Spex-II, which were established from the fat bodies of S. exigua. It was proposed that the 10-hydroxyl group in the camptothecin derivatives is a key factor for the antifeeding activity of a compound. The nature of the substituents was considered the major factor in determining the insecticidal activity of these compounds.
|
|
Received: 02 May 2013
Accepted: 06 June 2014
|
| Fund: This work has been supported by the National Natural Science Foundation of China (31171878, 31071707 and 31000851). |
|
Corresponding Authors:
JIANG Hong-yun, Tel/Fax: +86-10-62893622, E-mail: hyjiang6281@gmail.com
E-mail: hyjiang6281@gmail.com
|
| About author: DENG Li, Mobile: 15371011200, E-mail: dengli1102@126.com |
Cite this article:
DENG Li, ZHANG Lan, CAO Li-dong, XIE Ru-liang, ZHANG Yan-ning, HE Wei-zhi , JIANG Hong-yun.
2014.
Synthesis and Insecticidal Activity of Novel Camptothecin Derivatives Containing Analogs of Chrysanthemic Acid Moieties. Journal of Integrative Agriculture, 13(6): 1320-1330.
|
| Dayan F E, Cantrell C L, Duke S O. 2009. Natural products in crop protection. Bioorganic & Medicinal Chemistry, 17, 4022-4034 DeMilo A B, Borkovec A B. 1974. Camptothecin, a potent chemosterilant against the house fly. Journal of Economic Entomology, 67, 457-458 Duke S O, Cantrell C L, Meepagala K M, Wedge D E, Tabanca N, Schrader K K. 2010. Natural toxins for use in pest management. Toxins (Basel), 2, 1943-1962 Elliott M, Janes N F, Potter C. 1978. The future of pyrethroids in insect control. Annual Review of Entomology, 23, 443- 469. Gao R, Gao C, Tian X, Yu X, Di X, Xiao H, Zhang X. 2004. Insecticidal activity of deoxypodophyllotoxin, isolated from Juniperus sabina L., and related lignans against larvae of Pieris rapae L. Pest Management Science, 60, 1131-1136 He X, Lu W, Jiang X, Cai J, Zhang X, Ding J. 2004. Synthesis and biological evaluation of bis and monocarbonate prodrugs of 10-hydroxycamptothecins. Bioorganic & Medicinal Chemistry, 12, 4003-4008 Hsiang Y H, Lihou M G, Liu L F. 1989. Arrest of replication forks by drug-stabilized topoisomerase I-DNA cleavable complexes as a mechanism of cell killing by camptothecin. Cancer Research, 49, 5077-5082 Hsiang Y H, Liu L F. 1988. Identification of mammalian DNA topoisomerase I as an intracellular target of the anticancer drug camptothecin. Cancer Research, 48, 1722-1726 Hu Q, Han B Y, Ma J Y, Tang J. 2009. Field efficiency trials on Empoasca vitis Gothe with extractive from the leaf of Camptotheca acuminate. China Tea, 31, 32-33 (in Chinese) Isman M B. 2006. Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world. Annual Review of Entomology, 51, 45-66 Jiang H Y. 2008. Study on the insecticidal activity and mechanism of bioactive ingredient from the seeds of Camptotheca acuminata Decne and its derivatives. Ph D thesis, China Agricultural University, China. (in Chinese) Katsuda Y. 2012. Progress and future of pyrethroids. Topics in Current Chemistry, 314, 1-30 Li Y Y, You Q D, Wang L, Chen S, Chen X G, Li Y, Li H Y. 2006. 20(S)-20-O-camptothecin β-aminopropionate: novel synthesis and antitumor activity in vitro Chemical Research in Chinese Universities, 22, 727-731 Liu Y Q, Liu Y, Zhao Y L, Li H Y. 2010. Synthesis of novel derivatives of camptothecin as potential insecticides. Pesticide Biochemistry and Physiology, 98, 219-223 Lorence A, Medina B F, Nessler C L. 2004. Camptothecin and 10-hydroxycamptothecin from Camptotheca acuminata hairy roots. Plant Cell Reports, 22, 437-441 Oliveira F M, Barbosa L C A, Teiseira R R, Demuner A J, Maltha C R A, Silva G A, Paula V F D. 2012. Synthesis and insecticidal activity of new phosphoramidates. Journal of Pesticide Science (Tokyo, Japan), 37, 85-88 Redinbo M R. 1998. Crystal structures of human topoisomerase I in covalent and noncovalent complexes with DNA. Science, 279, 1504-1513 Riva E, Comi D, Borrelli S, Colombo F, Danieli B, Borlak J, Evensen L, Lorens J B, Fontana G, Gia O M, Via L D, Passarella D. 2010. Synthesis and biological evaluation of new camptothecin derivatives obtained by modification of position 20. Bioorganic & Medicinal Chemistry, 18, 8660-8668 Stewart L, Champoux J J. 1999. Methods in molecular biology. In: Osheroff N, Bjornsti M A, eds., Assaying DNA Topoisomerase I Relaxation Activity. vol. 95. Humana Press, Totowa, NJ. pp. 1-11 Tong S M, Wang P W, Zhang L Q, Ma J Y, Sheng X Q. 2009. Insecticidal effect of camptothecin against Nilaparvata lugens, Brevicoryne brassicae and Chilo suppressalis Walker. Acta Agriculturae Zhejiangensis, 21, 288-292 (in Chinese) Wall M E, Wani M C, Cook C E, Palmer K H, McPhail A T, Sim G A. 1966. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. Journal of the American Chemical Society, 88, 3888-3890 Wang Y, Li L, Jiang W, Larrick J W. 2005. Synthesis and evaluation of a DHA and 10-hydroxycamptothecin conjugate. Bioorganic & Medicinal Chemistry, 13, 5592- 5599. Zhang H, Zhang Y A, Qin Q, Li X, Miao L, Wang Y, Qu L, Zhang A, Yang Q. 2009. A cell strain cloned from Spodoptera exigua cell line (IOZCAS-Spex-II) highly susceptible to S. exigua nucleopolyhedrovirus infection. In Vitro Cellular & Developmental Biology-Animal, 45, 201-204 Zhang L, Zhang Y, He W, Ma D, Jiang H. 2012. Effects of camptothecin and hydroxycamptothecin on insect cell lines Sf21 and IOZCAS-Spex-II. Pest Management Science, 68, 652-657 Zhou S F, Zhang Y P, Chen M Y, Li D S, Zhang B X. 2010. Influence of camptothecin to Bactrocera dorsalis Hendel adults. Guangzhou Agricultural Sciences, 37, 89-92. (in Chinese) |
| No Suggested Reading articles found! |
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
| |
Shared |
|
|
|
|
| |
Discussed |
|
|
|
|
