Acetogenins from Annonaceae: Recent Progress in Isolation, Synthesis and Mechanisms of Action

Bermejo, Almudena; Figadère, Bruno; Zafra‐Polo, M. Carmen; Martínez, Isabel Barrachina; Estornell, Ernesto; Cortés, Diego

doi:10.1002/chin.200531238

Cited by 42 publications

(79 citation statements)

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“…The reports of isolated secondary metabolites from this species were of acetogenins (Bermejo et al, 2005;Silva et al, 1998Silva et al, , 1997aSilva et al, ,b, 1996Silva et al, , 1995Yu et al, 1994), diterpenoids (Onan & Mc Phail, 1978;Orsini et al, 1977;Mussini et al,1973a,b;Ferrari et al, 1971) and pterocarpans (Darko et al, 1983;Nakagawa et al, 1982). In our previous studies, in vitro antimalarial (Fischer et al, 2004), anti-leishmanial and trypanocidal (Tempone et al, 2005) activities were found for the crude ethanol extract and for the total alkaloids.…”

Section: Introductionmentioning

confidence: 87%

Chemical constituents of the volatile oil from leaves of Annona coriacea and in vitro antiprotozoal activity

Siqueira

Oliani

Sartoratto³

et al. 2011

Rev. bras. farmacogn.

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Abstract:The essential oil of the leaves from Annona coriacea Mart., Annonaceae, was extracted by hydrodistillation in a Clevenger apparatus and analyzed by GC/MS and GC/FID. The oil yield was 0.05% m/m. Sixty compounds were identified, in a complex mixture of sesquiterpenes (76.7%), monoterpenes (20.0%) and other constituents (3.3%). Bicyclogermacrene was its major compound (39.8%) followed by other sesquiterpenes. Most of the monoterpenes were in low concentration (<1%). Only β-pinene and pseudolimonene presented the highest level of 1.6%. The volatile oil presented anti-leishmanial and trypanocidal activity against promastigotes of four species of Leishmania and trypomastigotes of Trypanosoma cruzi, showing to be more active against Leishmania (L.) chagasi (IC50 39.93 µg/mL) (95% CI 28.00-56.95 µg/mL).

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Section: Introductionmentioning

confidence: 87%

Chemical constituents of the volatile oil from leaves of Annona coriacea and in vitro antiprotozoal activity

Siqueira

Oliani

Sartoratto³

et al. 2011

Rev. bras. farmacogn.

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“…These substances are natural products, promising as insecticide prototype, being commonly found in branch and root barks, roots and seeds of plants belonging to the Annonaceae family (BERMEJO et al, 2005; CASTILLO-SÁNCHEZ; JIMÉNEZ-OSORNIO; DELGADO-HERRERA, 2010).…”

Section: Survival Mortality Weight and Larval Period Length For Xanmentioning

confidence: 99%

FIRST RECORD OF Xanthopastis timais IN AMARYLLIS AND EFFECT OF SOURSOP EXTRACT ON LARVAL MORTALITY

et al. 2017

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-The aim of this study was to report the occurrence of Xanthopastis timais (Cramer, 1780) (Lepidoptera: Noctuidae) in amaryllis (Hippeastrum hybridum Hort., Amaryllidaceae), as well as estimating lethal concentrations (LC 50 and LC 99 ) of soursop seed extract, Annona muricata L. (Annonaceae), against its larvae. The experiment was carried out at the Laboratory of Entomology of the Research Center for Agricultural Sciences, Federal University of Alagoas, in Rio Largo-AL, Brazil. First, we collected caterpillars from amaryllis plants that were reared until pupal and adult stages (parental generation). Next, part of the adults was used for species identification, and the rest were bred to produce next generation (F1), being after that applied in a laboratory bioassay. The lab trial was performed in a completely randomized design, with six treatments and five replications containing three second-instar caterpillars. These larvae were fed pieces of amaryllis leaf (4 x 4 cm), which were previously soaked in treatments for 30 seconds and, air-dried on absorbent papers for one hour. Each treatment consisted of one concentration of ethanol extract of soursop seeds (0.0, 1.0, 0.5, 0.25, 0.125 and 0.0625% w/ v) with distilled water and DMSO at 1% (v/ v), for solutions. We noted that the lethal concentrations LC 50 and LC 99 were 0.29% (w/ v) and 2.27% (w/ v), respectively. In view of our results, we can state that larval stage of X. timais were influenced by extract application in terms of survival, mortality, larvae weight and larval stage length. Besides of that, it was the first time this species was recorded in Alagoas state.Keywords: Amaryllidaceae. Annona muricata. Floriculture. Spanish moth. Seeds. REGISTRO DE Xanthopastis timais EM AMARÍLIS E EFEITO DO EXTRATO DE GRAVIOLA NA MORTALIDADE LARVALRESUMO -O objetivo deste trabalho foi relatar a ocorrência em Alagoas da espécie Xanthopastis timais (Cramer, 1780) (Lepidoptera: Noctuidae) em amarílis (Hippeastrum hybridum Hort., Amaryllidaceae) e avaliar o uso do extrato de sementes de graviola, Annona muricata L. (Annonaceae), estimando as concentrações letais (CL 50 e CL 99 ) para as lagartas, bem como os efeitos na fase larval. O experimento foi conduzido no Laboratório de Entomologia do Centro de Ciências Agrárias da Universidade Federal de Alagoas em Rio Largo-AL. Foram coletadas lagartas em plantas de amarílis que foram criadas em folhas dessa planta, até a obtenção de pupas e de adultos (geração parental). Parte dos adultos foi usada para identificação específica, e outros, deram continuidade à geração seguinte (F1), que foi utilizada no bioensaio. O delineamento experimental foi inteiramente casualizado, constituído por seis tratamentos e cinco repetições com três lagartas de segundo ínstar por repetição. As lagartas foram alimentadas com porções de folhas de amarílis (4 x 4 cm), anteriormente imersas em seus devidos tratamentos durante 30 segundos e secas ao ar sobre papel absorvente durante uma hora. Os tratamentos foram: extrato etanólico de sementes d...

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“…Characteristic constituents of these plants are the annonaceous acetogenins that possess unique structures [1] and anticancer [2] [3], cytotoxic [4], insecticidal [5] [6], antiparasitic activities and as a highly interesting new generation of antitumor drugs [7] [8] [9] [10] [11]. Furthermore, acetogenin cytotoxicity would be strongly related to the conformation adopted in the membrane [12] [13] [14].…”

Section: Introductionmentioning

confidence: 99%

Natural and Derivatized Acetogenins Promising for the Control of <i>Spodoptera frugiperda</i> Smith

Hidalgo¹,

Parellada²,

Blessing³

et al. 2016

JACEN

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Annonaceous acetogenins (ACG), belonging to the family Annonaceae, represent a class of bioactive compounds whose toxic effects have been reported for several species of insects. Given their insecticidal properties, we first carried out the isolation of the ACG from a Brazilian collection of the seeds of Annona squamosa (Annonaceae) and prepared their methoxy methylated (MOM) and acetylated (OAc) derivatives by chemical methods. ACG analogues were semi-synthesized and characterized by spectroscopic techniques ( 1 H and 13 C-NMR). We isolated ten natural acetogenins: squamocin, molvizarin, motrilin, rolliniastatin-2, almuñequin, cherimolin-1, cherimolin-2, annonacin, squamocin D and asiminecin. The main objective of this study is to report the antifeedant, toxic and nutritional effects of three of those natural acetogenins and their acetylated and methoxy methylated derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). The natural ACGs squamocin and molvizarin killed 100% of S. frugiperda larvae, followed by motrilin (80%). Acetylated derivatives had less toxic and nutritional effects that led to pupal mortality and adult fatal malformations. The addition of MOM derivatives to the larval diet has not toxic effects on larvae, but significantly reduces growth rate and efficiency in conversion of ingested food into biomass, affecting adult survival.

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Acetogenins from Annonaceae: Recent Progress in Isolation, Synthesis and Mechanisms of Action

Abstract: Organic chemistry Z 0200 Acetogenins from Annonaceae: Recent Progress in Isolation, Synthesis and Mechanisms of Action -[171 refs.]. -(BERMEJO, A.; FIGADERE, B.; ZAFRA-POLO, M.-C.; BARRACHINA, I.; ESTORNELL, E.; CORTES*, D.; Nat. Prod. Rep. 22 (2005) 2, 269-303; Dep. Farmacol.,

Cited by 42 publications

References 1 publication

Chemical constituents of the volatile oil from leaves of Annona coriacea and in vitro antiprotozoal activity

Chemical constituents of the volatile oil from leaves of Annona coriacea and in vitro antiprotozoal activity

FIRST RECORD OF Xanthopastis timais IN AMARYLLIS AND EFFECT OF SOURSOP EXTRACT ON LARVAL MORTALITY

Natural and Derivatized Acetogenins Promising for the Control of <i>Spodoptera frugiperda</i> Smith

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Acetogenins from Annonaceae: Recent Progress in Isolation, Synthesis and Mechanisms of Action

Abstract: Organic chemistry Z 0200 Acetogenins from Annonaceae: Recent Progress in Isolation, Synthesis and Mechanisms of Action -[171 refs.]. -(BERMEJO, A.; FIGADERE, B.; ZAFRA-POLO, M.-C.; BARRACHINA, I.; ESTORNELL, E.; CORTES*, D.; Nat. Prod. Rep. 22 (2005) 2, 269-303; Dep. Farmacol.,

Cited by 42 publications

References 1 publication

Chemical constituents of the volatile oil from leaves of Annona coriacea and in vitro antiprotozoal activity

Chemical constituents of the volatile oil from leaves of Annona coriacea and in vitro antiprotozoal activity

FIRST RECORD OF Xanthopastis timais IN AMARYLLIS AND EFFECT OF SOURSOP EXTRACT ON LARVAL MORTALITY

Natural and Derivatized Acetogenins Promising for the Control of &lt;i&gt;Spodoptera frugiperda&lt;/i&gt; Smith

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Natural and Derivatized Acetogenins Promising for the Control of <i>Spodoptera frugiperda</i> Smith