Annonaceous acetogenins from seeds of Annona squamosa / 中草药

Objective To study the chemical composition from the seeds of Annona squamosa. Methods The components of annonaceous acetogenins from the seeds of A. squamosa were isolated and purified by extracting and chromatography separation. The structures of the compounds were identified by their physicochemical properties, UV, NMR, and mass spectrometry data. Results Seven annonaceous acetogenins were isolated from the ethyl acetate extract of the seeds from A.squamosa. They are 3-[7-[5- [1,4-dihydroxy-4-[5-(1-hydroxytridecyl)-2-furanyl] butyl] tetrahydro-2-furanyl]-2-hydroxyheptyl]-5-methyl-2(5H)-furanone (1), 3-[9-[5-(1-hydroxy-4-heptadeceneyl) tetrahydro-2-furanyl] hydroxynonyl]-5-methyl-2 (5H)-furanone (2), bullatalicin (3), squamostatin A (4), squamostatin D (5), bullatacin (6), and 10-hydroxyasimicin (7). Conclusion Compounds 1 and 2 are two new compounds, named as trilobalicin I (1) and D20-solamin B (2), respectively.

Two new annonaceous acetogenins from seeds of Annona squamosa / 中草药

Objective: To study the chemical constituents from the seeds of Annona squamosa. Methods: Modern methods such as silica gel column and preparation liquid phase were used to isolate and purify the components of annonaceous acetogenins from the seeds of A. squamosa. The structures of the compounds were identified by their physico-chemical properties, UV, NMR and mass spectrometry data. Results: Ten adjacent bistetrahydrofuran annonaceous acetogenins were isolated from CO2 supercritical extract of the seeds from A. squamosa. They were 3-((13R)-13-((2R,2'R,5R,5'R)-5'-((1S)-1,5-dihydroxynonyl) octahydro-[2,2'-bifuran]-5-yl)-13-hydroxytridecyl)-5-methylfuran-2 (5H)-one (1), 3-((2R,9R)-2,9-dihydroxy-9-((2R,2'R,5R,5'R)-5'-((S)-1-hydroxypentadecyl) octahydro-[2,2'-bifuran]-5-yl) nonyl)-5-methylfuran-2 (5H)-one (2), 6-hydroxy-desacetyl-uvaricin (3), 6-hydroxy-4-deoxy-squamotacin (4), bullanin (5), 10-hydroxy-asimicin (6), folianin A (7), annosquacin I (8), annosquacin C (9), and squamocin I (10). Conclusion: Compounds 1 and 2 are two new compounds named as 28-hydroxy-squamocin L (1) and 4-hydroxy-squamocin Y (2), respectively. Compounds 3-7 are isolated from A. squamosa for the first time.

Searching for promising sources of grain protectors in extracts from neotropical annonaceae / Búsqueda de fuentes prometedoras de protectores de granos en extractos de anonaceas neotropicales

To investigate potential sources of novel grain protector compounds against Sitophilus zeamais (Coleoptera: Curculionidae), which is an important insect pest of stored cereals, this study evaluated the bioactivity of ethanolic extracts (66) prepared from 29 species belonging to 11 different genera of Neotropical Annonaceae. A screening assay demonstrated that the most pronounced bioactive effects on S. zeamais were caused by ethanolic extracts from Annona montana, A. mucosa, A. muricata, and A. sylvatica seeds, causing the death of all weevils exposed, almost complete inhibition of the F1 progeny and a drastic reduction in grain losses. Furthermore, the ethanolic extracts obtained from the leaves of A. montana, A. mucosa, A. muricata, and Duguetia lanceolata, especially A. montana and A. mucosa, demonstrated significant bioactive effects on the studied variables; however, the activity levels were less pronounced than in the seed extracts, and the response was dependent on the concentration used. This study is the first to report the activity of secondary metabolites from D. lanceolata on insects as well as the action of A. sylvatica on pests associated with stored grains.

Para investigar las posibles fuentes de nuevos compuestos protectores de granos contra Sitophilus zeamais (Coleoptera: Curculionidae), una importante plaga de los cereales almacenados, este estudio evaluó la bioactividad de los extractos etanólicos (66) preparados a partir de 29 especies pertenecientes a 11 géneros distintos de Anonaceas Neotropicales. Un ensayo de selección demostró que los efectos bioactivos más relevantes sobre S. zeamais fueron causados por los extractos etanólicos de las semillas de Annona montana, de A. mucosa, de A. muricata y de A. sylvatica, que causaron la muerte de todos los gorgojos expuestos, la inhibición parcial de la progenie F1 y una drástica reducción de las pérdidas de grano. Además, los extractos etanólicos obtenidos de las hojas de A. montana, de A. mucosa, de A. muricata y de Duguetia lanceolata, especialmente de A. montana y de A. mucosa, demostraron efectos bioactivos significativos sobre las variables estudiadas. Sin embargo, los niveles de bioactividad fueron menores en comparación con los extractos de semillas, y la respuesta fue dependiente de la concentración utilizada. Este estudio es el primer relato sobre la actividad de los metabolitos secundarios de D. lanceolata sobre insectos, así como la acción de A. sylvatica sobre plagas asociadas a los granos almacenados.

Antimicrobial and cytotoxic acetogenin from Polyalthia debilis.

The objective of the study was to isolate bioactive acetogenin compound and to investigate antimicrobial, antioxidant as well as cytotoxic activities of the isolate, fractions and extracts of Polyalthia debilis. The P. debilis (roots) extracts and isolated compound were tested for their antimicrobial (agar dilution method) against twentyseven strains of microorganisms (gram positive and gram negative bacteria, and diploid fungus), antioxidant (DPPH assay) and cytotoxic activities. The plant extracts were isolated by column chromatography and structure of compound was confirmed by spectral data. The plant extracts and isolated fractions exhibited antioxidant and cytotoxic activities. The isolated acetogenin 1 (debilisone E) displayed antimicrobial activity against Morexella catarrhalis with the MIC of 64 g/mL, Corynebacterium diphtheriae NCTC 10356 and Streptococcus pyogenes with partial inhibition (50-75%) at 128 g/mL. The compound 1 exerted cytotoxic activity against 5 cancer cells (HepG2, A549, HCC-S102,HL-60 and P388) with IC50 values 18.4 - 40.3g/mL. The results demonstrate novel bioactivities of P. debilis as antimicrobials and anticancer agents.

Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae / Xymarginatin: uma nova acetogenina inibidora do transporte mitocondrial eletrônico de Xylopia emarginata Mart., Annonaceae

A new Annonaceous acetogenin, xymarginatin (1), was isolated from the twigs of Xyliopia emarginata Mart. (Annonaceae) by bioactivity-directed fractionation using lethality to brine shrimp. The compound 1 represents a linear C-35 Annonaceous acetogenin, lacking either tetrahydrofuran (THF) or epoxide rings, bearing a keto group at C-10, and possessing two cis-double bonds separated by two methylenes units. The structure of 1 was elucidated by ¹H and 13C-NMR, COSY, HMBC, HMQC and HRMS. The ability to inhibit the mitochondrial respiratory chain of Xymarginatin (1) was tested in a rat liver mitochondrial oxygen uptake assay, with IC50 value of 1720 nM; Rotenone as a positive control gave IC50 34.8 nM. The toxicity of compound 1 against Artemia salina Leach gave LC50 of 127 μg/mL.

Uma nova acetogenina de Anonaceae, xymarginatin (1), foi isolada dos caules de Xyliopia emarginata Mart. (Annonaceae) por fracionamento biodirecionado usando o teste de letalidade em Artemia salina. A substância 1 representa uma acetogenina linear C-35, sema neis tetrahidrofureano ou epóxidos, mas com um grupo cetônico em C-10 e com uma dupla ligação cis separada por duas unidades metilênicas. A estrutura de 1 foi elucidada por ¹H e 13C-RNM, COSY, HMBC, HMQC e HRMS. A habilidade de inibir a cadeia respiratória mitocondrial de 1 foi testada em ensaios de produção de oxigênio mitocondrial em fígado de ratos, com IC50 de 1720 nM; rotenona, controle positivo, apresentou IC50 de 34,8 nM. A toxicidade da substância 1 contra Artemia salina Leach foi de LC50 127 μg/mL.

Effect of Annonaceous Acetogenin on Proliferation and Apoptosis of Raji Cell / 中国中医药信息杂志

Objective To investigate the effects of annonaceous acetogenin on proliferation and apoptosis in Raji cells and its mechanism.Methods Raji cells cultured in vitro were divided into control group,annonaceous acetogenin group and adriamycin group.Raji cells were effected by 6.25,12.5,25,50 ?g/mL annonaceous acetogenin.Proliferation of Raji cells were evaluated by MTT assays,apoptosis percentage was assessed by flow cytometry.Caspase-9 protein was detected by immunohistochemistry.Results The Raji cell proliferation rate of annonaceous acetogenin decreased compared with the control,that of 25,50 ?g/mL group were lower than adriamycin group,and it was related to the concentration,relying on the incubating time.The apoptosis rate was higher than control,that of 25,50 ?g/mL group were higher than adriamycin group,and it was related to the concentration and the incubating time.The expression of caspase-9 protein of annonaceous acetogenin group was higher than control,and it had a positively relationship with the concentration and incubating time.Conclusions Annonaceous acetogenin could inhibit cell proliferation in a dose-dependent and time-dependent manner in Raji cells,and it may induce Raji cells apoptosis by up-regulating caspase-9 expression.