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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

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

滇产圆滑番荔枝中新的acetogenins

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云南植物研究 1995年第2期17卷 224-226页

作者：李朝明孙汉董郑惠兰陶国达中国科学院昆明植物研究所植物化学开放实验室中国科学院西双版纳热带植物园

滇产圆滑番荔枝中新的ａｃｅｔｏｇｅｎｉｎｓ李朝明，孙汉董，郑惠兰，陶国达（中国科学院昆明植物研究所植物化学开放实验室，昆明６５０２０４）（中国科学院西双版纳热带植物园，云南勐腊６６６３０３）ＮＥＷＡＣＥＴＯＧＥＮＩＮ... 详细信息

滇产圆滑番荔枝中新的ａｃｅｔｏｇｅｎｉｎｓ李朝明，孙汉董，郑惠兰，陶国达（中国科学院昆明植物研究所植物化学开放实验室，昆明６５０２０４）（中国科学院西双版纳热带植物园，云南勐腊６６６３０３）ＮＥＷＡＣＥＴＯＧＥＮＩＮＳＦＲＯＭＡＮＮＯＮＡＧＬＡＢＲＡ...

关键词：圆滑番荔枝 acetogenins 番荔枝科化学成分

Muricatenol, a Linear Acetogenin from Annona muricata (Annonaceae)

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Chinese Chemical Letters 2000年第3期11卷 239-242页

作者： De Yu LI Jing Guang YU Xiu Zhen LUO Lan SUN Shi Lin YANG (Institute of Medicinal Plant Development. Chinese Academy of Medical Sciences and Peking Union Medical College. Beijing 100094) Chinese Acad Med Sci Inst Med Plant Dev Beijing 100094 Peoples R China Peking Union Med Coll Beijing 100094 Peoples R China

Muricatenol 1, a new acetogenin, has been isolated from the seeds of Annona muricata L.. Compound 1 is a C-37 acetogenin without any THF rings. with four hydroxyls and one double bond in the long aliphatic chain. The hydroxyls of 1 are located at C-4, C-10, C-18 and C-19. respectively. The vicinal diet at C-18/C-19 is threo-configuration, and the double bond at C-14/C-15 is cis-configuration.

关键词： Annona muricata Annonaceae acetogenins muricatenol

Larvicidal efficacy of plant extracts and isolated compounds from Annonaceae and Piperaceae against Aedes aegypti and Aedes albopictus

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Asian Pacific Journal of Tropical Medicine 2020年第9期13卷 384-396页

作者： Alzeir M.Rodrigues Victor Emanuel P.Martins Selene M.Morais Departamento de Ensino Instituto Federal de EducaçãoCiência e Tecnologia do Ceará(IFCE)Rodovia CE 060km 332Vila Martins63.560-000 AcopiaraCearáBrazil Programa de Pós-Graduação em Biotecnologia RENORBIOUniversidade Estadual do CearáAvenida Doutor Silas Munguba170060741-000 FortalezaCearáBrazil Instituto de Ciências Exatas e da Natureza Universidade da Integração Internacional da Lusofonia Afro-Brasileira(Unilab)Campus das AurorasRua JoséFranco de Oliveira s/n62790-970 RedençãoCearáBrasil Departamento de Química Universidade Estadual do CearáAvenida Doutor Silas Munguba170060741-000 FortalezaCearáBrazil

The Aedes(Ae.)aegypti and *** mosquitoes are vectors of epidemiologically relevant arboviruses in the public health context,such as the dengue,Zika and chikungunya *** the alternatives to synthetic insecticides for the control of these vectors,the use of natural plant products deserves *** review summarizes findings on the larvicidal potential of plant extracts on *** and ***,as well as the potential of isolated compounds from plants of the Annonaceae and Piperaceae families against these *** related to larvicidal activity of plant extracts and isolated compounds in Aedes *** the Web of Science database were used,for plant extracts considering publications between 2000 and 2019.A total of 859 articles were analyzed for plant extracts and estimates of lethal concentration values(LC50 and LC90).In the end,95 articles that presented the larvicidal potential of 150 plant species from 52 families were *** two families most studied for this activity were Fabaceae and Asterace *** plant families with the best LC50 values against mosquitoes were Piperaceae and *** activity of 50 acetogenins has already been identified on ***,and 29 of them presented LC50 below 10μg/mL,as well as the larvicidal activity of 8 compounds isolated from ***,plants of these two families are promising for the development of commercial botanical larvicides in the form of extracts and isolated substances,as well as the production via organic synthesis of the most active compounds.

关键词： Larvicidal activity Plant extracts acetogenins Aedes

A New Cytotoxic Acetogenin from the Seeds of Annona squamosa

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Chinese Chemical Letters 2003年第6期14卷 588-590页

作者： Hai Hui XIE, Xiao Yi WEI*, Ji Dong WANG, Mei Fang LIU, Ren Zhou YANG South China Institute of Botany, Chinese Academy of Sciences, Guangzhou 510650 South China Institute of Botany Chinese Academy of Sciences

A new Annonaceous acetogenin, squamostolide (1), was isolated from the seeds of Annona squamosa. Its structure was elucidated based on spectroscopic methods and comparison with known compounds. It is the first example of Annonaceous acetogenin with each of the two ends of the aliphatic chain bearing a g-lactone. The new compound exhibited cytotoxic activity in vitro against bel-7402 and CNE2 human tumor cell lines.

关键词： Annona squamosa Annona acetogenins squamostolide cytotoxicity.

Annona muricata fruit extract protects against diethylnitrosamine-induced hepatocellular cancer in rats

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Asian Pacific Journal of Tropical Medicine 2019年第6期12卷 272-282页

作者： Subin Varghese Thomas John Paul Akhila Hosur Shrungeswara Subhankar Biswas Aarti Abhishek Shah Chandrashekar Kodangala Subraya Yogendra Nayak Department of Pharmacology Manipal College of Pharmaceutical SciencesManipal Academy of Higher EducationManipalIndia Department of Pharmacy Practice Manipal College of Pharmaceutical SciencesManipal Academy of Higher EducationManipalIndia Department of Pharmacognosy Manipal College of Pharmaceutical SciencesManipal Academy of Higher EducationManipalIndia

Objective: To evaluate the anticancer potentials of Annona muricata fruit by in vitro and in vivo methods. Methods: The ethanolic extract of Annona muricata fruit was prepared by Soxhlet extraction method and further fractionated with petroleum ether, ethyl acetate and chloroform. The fractions were tested for cytotoxicity, apoptosis, scratch wound assay, and cell cycle analysis. IC50, apoptotic index and percentage cell migration were determined using HepG2 cells. For the in vivo studies, hepatocellular carcinoma was induced by administering 0.01% diethylnitrosamine(DEN) in drinking water in Wistar rats. In pre-treatment, rats were co-administered 200 mg/kg of fruit extract with DEN for 14 weeks. In post-treatment, the extract was co-administered after 8-weeks of DEN-induction for 14 weeks. Liver function test, haematological test, oxidative stress markers, relative liver weight, number of cancer nodules and histopathological parameters were ***: Annona muricata fruit extract =significantly lowered cell proliferation counts. The chloroform-fraction possessed higher activity (IC50=(53.7±4.3) μg/mL)The chloroform fraction inhibited cell migration, which was significant compared to curcumin. Further investigations regarding the mode of anticancer activity revealed that the chloroform fraction induced apoptosis. The cell cycle analysis indicated that cells were being arrested at G0/G1. In the in vivo studies, the DEN-control group showed a significant decrease in body weights with increased mortality rate, hepatic nodules, and impairment of liver function compared to normal rats. The rats pre-treated and post-treated with the extract showed positive results with significant improvement in the parameters that were adversely affected by DEN. In addition, other adverse effects of DEN, such as blood dyscrasias and hepatic endogenous antioxidant, were significantly attenuated by Annona muricata fruit ***: The Annona muricata fruit extract has

关键词： HepG2-cells Apoptosis Liver cancer acetogenins Rat liver cancer Scratch wound assay

Annona muricata:Is the natural therapy to most disease conditions including cancer growing in our backyard?A systematic review of its research history and future prospects

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Asian Pacific Journal of Tropical Medicine 2017年第9期10卷 835-848页

作者： Yahaya Gavamukulya Fred Wamunyokoli Hany A.El-Shemy Department of Molecular Biology and Biotechnology Pan African University Institute for Basic SciencesTechnology and Innovation(PAUSTI)P.O.Box62000-00200 NairobiKenya Department of Biochemistry and Molecular Biology Busitema University Faculty of Health SciencesP.O.Box1460 MbaleUganda Department of Biochemistry Jomo Kenyatta University of Agriculture and TechnologyP.O.Box62000-00200 NairobiKenya Department of Biochemistry Faculty of AgricultureCairo University12613 GizaEgypt

Annona muricata(***)is a tropical plant species belonging to family Annonaceae and known for its many medicinal *** review focuses on the research history of its traditional uses,phytochemicals,pharmacological activities,toxicological aspects of the extracts and isolated compounds,as well as the in vitro propagation studies with the objective of stimulating further studies on this plant for human consumption and *** extracts have been identified in tropical regions to traditionally treat diverse conditions ranging from fever to diabetes and *** than 200 chemical compounds have been identified and isolated from this plant,the most important being alkaloids,phenols and *** in vitro studies,its extracts and phytochemicals have been characterized as antioxidant,anti-microbial,anti-inflammatory,insecticidal,larvicidal,and cytotoxic to cancer *** vivo studies have revealed anxiolytic,antistress,anti-inflammatory,immunomodulatory,antimalarial,antidepressant,gastro protective,wound healing,hepato-protective,hypoglycemic,anticancer and anti-tumoral *** silico studies have also been *** addition,clinical studies support the hypoglycemic as well as some anticancer *** of action of some pharmacological activities have been ***,some phytochemical compounds isolated from *** have shown a neurotoxic effect in vitro and in vivo,and therefore,these crude extracts and isolated compounds need to be further investigated to define the magnitude of the effects,optimal dosage,and mechanisms of action,long-term safety,and potential side ***,more clinical studies are necessary to support the therapeutic potential of this *** studies were also found to have successfully regenerated the plant in vitro,but with limited *** reported toxicity notwithstanding,*** extracts seem to be some of the safest and promising therapeutic agents of the 21st

关键词： Annona muricata Traditional medicinal uses Phytochemicals acetogenins Bioactivity Cytotoxicity

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