1174-97-6Relevant academic research and scientific papers
Synthesis and quantitative structure-activity relationship (QSAR) study of novel 4-acyloxypodophyllotoxin derivatives modified in the A and C rings as insecticidal agents
He, Shuzhen,Shao, Yonghua,Fan, Lingling,Che, Zhiping,Xu, Hui,Zhi, Xiaoyan,Wang, Juanjuan,Yao, Xiaojun,Qu, Huan
, p. 618 - 625 (2013/03/28)
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, we have synthesized three series of novel 4-acyloxy compounds derived from podophyllotoxin modified in the A and C rings, which is isolated as the main secondary metabolite from the roots and rhizomes of Podophyllum hexandrum. Their insecticidal activity was preliminarily evaluated against the pre-third-instar larvae of Mythimna separata in vivo. Compound 9g displayed the best promising insecticidal activity. It revealed that cleavage of the 6,7-methylenedioxy group of podophyllotoxin will lead to a less active compound and that the C-4 position of podophyllotoxin was the important modification location. A quantitative structure-activity relationship (QSAR) model was developed by genetic algorithm combined with multiple linear regression (GA-MLR). For this model, the squared correlation coefficient (R 2) is 0.914, the leave-one-out cross-validation correlation coefficient (Q2LOO) is 0.881, and the root-mean-square error (RMSE) is 0.024. Five descriptors, BEHm2, Mor14v, Wap, G1v, and RDF020e, are likely to influence the biological activity of these compounds. Among them, two important ones are BEHm2 and Mor14v. This study will pave the way for further design, structural modification, and development of podophyllotoxin derivatives as insecticidal agents.
Synthesis and cytotoxicity of podophyllotoxin analogues modified in the A ring
Castro, Angeles,Del Corral, Jose M. Miguel,Gordaliza, Marina,Grande, Concepcion,Gomez-Zurita, Antonia,Garcia-Gravalos, Dolores,San Feliciano, Arturo
, p. 65 - 74 (2007/10/03)
Several podophyllotoxin derivatives lacking the methylenedioxy group or with different functionalization of the A-ring of the cyclolignan skeleton have been prepared and evaluated for their cytotoxic activities on four neoplastic cell lines (P-388, A-549,
In vivo immunosuppressive activity of some cyclolignans
Gordaliza, Marina,Castro, M. Angeles,Miguel del Corral, Jose M.,Lopez-Vazquez, M. Luisa,San Feliciano, Arturo,Faircloth, Glynn T.
, p. 2781 - 2786 (2007/10/03)
Several podophyllotoxin-related cyclolignans, either lacking the lactone ring or the methylenedioxy grouping, have been prepared and evaluated for their immunosuppressive (IMS) activity in the mouse allogeneic MLR in vitro test and in the in vivo techniqu
Synthesis of podophyllotoxin A-ring pyridazine analogue
Bertounesque, Emmanuel,Imbert, Thierry,Monneret, Claude
, p. 14235 - 14246 (2007/10/03)
Podophyllotoxin A-ring pyridazine analogue 3 has been constructed in nine steps from (-)-podophyllotoxin. The Stille reaction was exploited to generate the key intermediate 4.
Antitumor agents. 124. New 4β-substituted aniline derivatives of 6,7-O,O- demethylene-4'-O-demethylpodophyllotoxin and related compounds as potent inhibitors of human DNA topoisomerase II
Wang,Hu,Chen,Cheng,Lee
, p. 871 - 877 (2007/10/02)
A series of 6,7-O,O-demethylene-4'-O-demethyl-4β-(substituted anilino)-4- desoxypodophyllotoxins (18-23), 6,7-O,O-demethylene-6,7-O,O-dimethyl-4'-O- demethyl-4β-(substituted anilino)-4-desoxypodophyllotoxins (28-31), and their corresponding 4'-O-methyl an
BIOSYNTHESIS OF PODOPHYLLUM LIGNANS - I. CINNAMIC ACID PRECURSORS OF PODOPHYLLOTOXIN IN PODOPHYLLUM HEXANDRUM
Jackson, David E.,Dewick, Paul M.
, p. 1029 - 1036 (2007/10/02)
Feeding experiments in Podophyllum hexandrum plants have established that phenylalanine, cinnamic acid and ferulic acid are good precursors of the two major aryltetralin lignans podophyllotoxin and 4'-demethylpodophyllotoxin.Sinapic and 3,4,5-trimethoxycinnamic acids were poorly utilized, showing that the substitution pattern of the pendent aryl ring is built up after coupling of the two phenylpropane units.Degradation studies on podophyllotoxin derived from ferulic acid show that the two halves of the lignan molecule are equally labelled supporting a biosynthetic sequence involving oxidative coupling of two similar phenylpropane precursors having the substitution pattern of ferulic acid.Although 3,4-methylenedioxycinnamic acid was readily incorporated, degradative studies prove that this compound is not incorporated intact, but via a metabolic sequence in which the methylenedioxy carbon atom enters the C1-pool and then labels the methylenedioxy and methoxyl substituents of podophyllotoxin.The rest of the skeleton is incorporated via ferulic acid, presumably by way of caffeic acid.Key Word Index - Podophyllum hexandrum; Podophyllaceae; aryltetralin; lignans; biosynthesis; podophyllotoxin.
