Synthesis of some ester derivatives of 4'-demethoxyepipodophyllotoxin/2'-chloro-4'-demethoxyepipodophyllotoxin as insecticidal agents against oriental armyworm, Mythimna separata Walker. 2017

Jiulin Huang, and Ming Xu, and Shaochen Li, and Jiani He, and Hui Xu
Research Institute of Pesticidal Design & Synthesis, College of Sciences/Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China; School of Chemistry & Chemical Engineering, Ankang University, Ankang 725000, Shaanxi Province, China.

Podophyllotoxin is a naturally occurring non-alkaloid toxin isolated from the roots and rhizomes of Podophyllum peltatum and P. hexandrum. In continuation of our program aimed at the discovery and development of natural product-based insecticides, two series of ester derivatives of 4'-demethoxyepipodophyllotoxin/2'-chloro-4'-demethoxyepipodophyllotoxin were prepared. The structures of the target compounds were well characterized by 1H NMR, IR, optical rotation and mp. The precise three-dimensional structural information of 8j was further determined by single-crystal X-ray diffraction. Their insecticidal activity was tested against Mythimna separata Walker. These compounds showed delayed insecticidal activity. Among all derivatives, some compounds showed more potent insecticidal activity than toosendanin against M. separata; especially compounds 8k and 9k exhibited the most potent activity with the final mortality rates of 71.4%. Their structure-activity relationships were discussed.

UI MeSH Term Description Entries
D007306 Insecticides Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. Insecticide
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D009036 Moths Insects of the suborder Heterocera of the order LEPIDOPTERA. Antheraea,Giant Silkmoths,Giant Silkworms,Silkmoths, Giant,Silkworms, Giant,Antheraeas,Giant Silkmoth,Giant Silkworm,Moth,Silkmoth, Giant,Silkworm, Giant
D011034 Podophyllotoxin A lignan (LIGNANS) found in PODOPHYLLIN resin from the roots of PODOPHYLLUM plants. It is a potent spindle poison, toxic if taken internally, and has been used as a cathartic. It is very irritating to skin and mucous membranes, has keratolytic actions, has been used to treat warts and keratoses, and may have antineoplastic properties, as do some of its congeners and derivatives. Epipodophyllotoxin,CPH86,Condyline,Condylox,Podocon-25,Podofilm,Podofilox,Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 alpha))-Isomer,Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 beta))-Isomer,Podophyllotoxin, (5R-(5 alpha,5a alpha,8a beta,9 alpha))-Isomer,Podophyllotoxin, (5R-(5 alpha,5a beta,8a alpha,9 beta))-Isomer,Wartec,Warticon
D011035 Podophyllum A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA. Podophyllums
D004305 Dose-Response Relationship, Drug The relationship between the dose of an administered drug and the response of the organism to the drug. Dose Response Relationship, Drug,Dose-Response Relationships, Drug,Drug Dose-Response Relationship,Drug Dose-Response Relationships,Relationship, Drug Dose-Response,Relationships, Drug Dose-Response
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

Related Publications

Jiulin Huang, and Ming Xu, and Shaochen Li, and Jiani He, and Hui Xu
January 2015, Bioorganic & medicinal chemistry letters,
Jiulin Huang, and Ming Xu, and Shaochen Li, and Jiani He, and Hui Xu
April 2014, Journal of agricultural and food chemistry,
Jiulin Huang, and Ming Xu, and Shaochen Li, and Jiani He, and Hui Xu
January 2015, Bioorganic & medicinal chemistry letters,
Jiulin Huang, and Ming Xu, and Shaochen Li, and Jiani He, and Hui Xu
January 2019, Frontiers in physiology,
Jiulin Huang, and Ming Xu, and Shaochen Li, and Jiani He, and Hui Xu
February 2024, International journal of biological macromolecules,
Jiulin Huang, and Ming Xu, and Shaochen Li, and Jiani He, and Hui Xu
January 2015, Mitochondrial DNA,
Jiulin Huang, and Ming Xu, and Shaochen Li, and Jiani He, and Hui Xu
May 2018, Scientific reports,
Jiulin Huang, and Ming Xu, and Shaochen Li, and Jiani He, and Hui Xu
June 2021, Insects,
Jiulin Huang, and Ming Xu, and Shaochen Li, and Jiani He, and Hui Xu
December 2014, Bioorganic & medicinal chemistry letters,
Jiulin Huang, and Ming Xu, and Shaochen Li, and Jiani He, and Hui Xu
September 2009, Bioorganic & medicinal chemistry letters,
Copied contents to your clipboard!