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Eight new cytotoxic annonaceous acetogenins from the seeds of Annona squamosa

Chinese Journal of Natural Medicines 2019年第4期17卷 291-297页

作者： MA Cheng-Yao LU Jia-Hui LI Xiang LIU Xiao CHEN Jian-Wei Pharmaceutical Institute Nanjing University of Chinese Medicine Engineering Center of State Ministry of Education for Standardization of Chinese Medicine Processing

Eight new annonaceous acetogenins, squamotin A–D(1–4), annosquatin IV–V(5 and 6), muricin O(7) and squamosten B(8), together with four known ones(9–12) were isolated from the seeds of Annona squamosa. Their structures were elucidated by chemical methods and spectral data. The inhibitory activities of compound 1–9 against three multidrug resistance cell lines were evaluated. All tested compounds showed strong cytotoxicity.

关键词： Annona squamosa annonaceous acetogenins Cytotoxicity Multidrug resistance

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Structural Factors of annonaceous Acetogenins and Their Semisynthetic Analogues Related with the Toxicity on Spodoptera frugiperda

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Journal of Agricultural Chemistry and Environment 2015年第2期4卷 56-61页

作者： Lilian Di Toto Blessing Florencia Budeguer Juan Ramos Alicia Bardón Sonia Diaz Margarita Brovetto Gustavo Seoane Adriana Neske Instituto de Química Orgánica Facultad de Bioquímica Química y Farmacia Universidad Nacional de Tucumán Ayacucho Argentina Instituto de Química Física Facultad de Bioquímica Química y Farmacia Universidad Nacional de Tucumán Ayacucho Argentina INQUINOA-CONICET Tucumán Argentina Dpto de Química Orgánica Fac de Química UdelaR Montevideo Uruguay

Toxic and nutritional effects of annonaceous acetogenins and their semisynthetic analogues on Spodoptera frugiperda were evaluated. Structural modification of the natural ACG, blocking the OH flanking THF with MOM, allowed us to suggest the mode of action of ACG in the membrane. Our study emphasizes the role of the flanking OH and acetyl groups of THF with the membrane hydrophilic polar head groups. They are essential structural factors in the ACG that facilitate the intermolecular interaction that dehydrates the membrane and makes it potentially toxic against Spodoptera frugiperda.

关键词： annonaceous Acetogenins Polyphagous Lepidopteran Toxicity Nutritional Alterations

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Insecticidal Activity of annonaceous Acetogenins and Their Derivatives on <em>Spodoptera frugiperda</em>Smith (Lepidoptera: Noctuidae)

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Journal of Agricultural Chemistry and Environment 2018年第3期7卷 105-116页

作者： José Ruiz Hidalgo Eduardo A. Parellada Alicia Bardón Nancy Vera Adriana Neske Instituto de Química Orgánica Facultad de Bioquímica Química y Farmacia UNT Tucumán Argentina Inquinoa-Conicet Facultad de Bioquímica Química y Farmacia UNT Tucumán Argentina Instituto de Farmacia Facultad de Bioquímica Química y Farmacia UNT Tucumán Argentina

Background: annonaceous acetogenins enclose a large number of biological activities, among which the insecticidal stands out. Methods: We report herein the biocide effects of natural acetogenins from Annona squamosa, A.?muricata and A. montana seeds: annonacin, cis-annonacin, cis-annonacin-10- one, asimicin, rolliniastatin-2, cherimolin-1, cherimolin-2, almuñequin, and two β-OH acetogenins: laherradurin and itrabin on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). Also, some acetylated and methoxy methylated ACG derivatives were synthesized and evaluated: annonacin (3 OAc), annonacin (4 OAc), asimicin (3 OAc), rolliniastatin-2 (3 OAc), rolliniastatin-2 (MOM), laherradurin (3 OAc) and itrabin (3 OAc). Results: The natural acetogenin rolliniastatin-2 (100 μg·g-1 of diet) produced the most important toxic action causing 100% mortality of early instar larvae. Derivatization of ACG yielded compounds that produced nutritional alterations. The incorporation of rolliniastatin-2 (3 OAc) and rolliniastatin-2 (3 MOM) (100 μg·g-1) into the artificial diet of Spodoptera frugiperdadisplayed the strongest antifeedant effects causing marked decreasings in larval growth and adult lethal malformations. Conclusion: Natural acetogenins are promising metabolites for insect control. Derivatization of these compounds reduces their toxicity to early instar larvae.

关键词： annonaceous Acetogenins Biocides Spodoptera frugiperda

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Insecticidal Effects of the annonaceous Acetogenin Squamocin and the Acetogenin Fraction of Seeds of <i>Rollinia occidentalis</i>on Soybean and Corn Pests

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Journal of Agricultural Chemistry and Environment 2014年第4期3卷 156-160页

作者： Diego Tolosa José Ruiz Hidalgo Pedro Eugenio Sal Susana Popich Alicia Bardón Adriana Neske Instituto de Química Orgánica Facultad de Bioquímica Química y Farmacia Universidad Nacional de Tucumán Ayacucho Argentina Universidad Nacional de Chilecito Chilecito Argentina INQUINOA-CONICET Tucumán Argentina

A treatment based on the acetogenin fraction of the methanol extract of Rollinia occidentalis seeds was applied to soybean crops for three consecutive years. In relation to the control population, the treatment reduced the population of Anticarsia gemmatalis, Rachiplusia nu, Pseudoplusia includens, Loxostege bifidalis and Spodoptera frugiperda to 52% and 65% after 48 h of application at concentrations of 500 and 750 μg/mL respectively, while low toxic effects were detected on natural enemies. The extract treatment at 500 μg/mL and a solution of the annonaceous acetogenin, squamocin, at 50 and 100 μg/mL, were also applied to a corn field to produce 75%, 93% and 100% mortality rates on the population of S. frugiperda, respectively, after 72 h of application. In addition, damages caused by lepidopterans in treated crops were lower than those observed in non treated fields, evaluated by residual biomass. This statement is based on data from trials with the commercially available insecticides lufenuron and cypermethrin.

关键词： annonaceous Acetogenins Polyphagous Lepidopteran Soybean Crops Corn Crops Spodoptera frugiperda

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Chemical Biology Studies on Molecular Diversity of annonaceous Acetogenins

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合成化学 2004年第z1期12卷 131-131页

作者： Yao Zhu-Jun State Key Laboratory of Bioorganic and Natural Products Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 354 Fenglin Road Shanghai 200032 China

annonaceous acetogenins, isolated from the Annonaceae plants, have been attracting worldwide attention in recent years due to their biological activities, especially as growth inhibitors of certain tumor ceils [ 1 ]. They have been shown to function by blocking complex I in mitochondria [2] as well as ubiquinone-linked NADPH oxidase in the cells of specific tumor cell lines, including some multidrug-resistant ones [3]. These features make these acetogenins excellent leads for the new antitumor agents. In our previous work, the compounds 1a to 1d (Figure 1), which relies on structure simplification while maintaining all essential functionalities of the acetogenins, was in vitro tested against several human solid tumor cell lines and showed interesting cell selectivity [4]. All four analogues show remarkable activity against the HCT-8 and HT-29 cell lines, while compound 1c was found the best [4bi. In order to further investigate the effects of key structural features, a convergent parallel fragments assembly strategy was developed [4e]. In addition, the biological relevancies of typical annonaceous acetogenin mimetics were also studied [4f].

关键词： annonaceous acetogenins, mimicking, fragment assembly, chemical biology,anticancer.

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