Anthelmintic acetogenin from Annona squamosa L. Seeds

Souza, M.M.C.; Beviláqua, Cláudia Maria Leal; Morais, Selene Maia de; Costa, C.T.C.; Silva, Ana R.A.; Braz-Filho, Raimundo

doi:10.1590/s0001-37652008000200005

Cited by 32 publications

(20 citation statements)

References 16 publications

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“…The silica gel column chromatography of the alkaloid extract of A. squamosa leaves led to the isolation of O-methylarmepavine (I), a benzylisoquinolinic alkaloid; and from the methanol extract free from alkaloids, a C 37 trihydroxy adjacent bistetrahydrofuran acetogenin (II) was isolated (Figure 1). This acetogenin was shown to be identical, when compared by thin layer chromatography (TLC) and spectroscopic data, with the acetogenin previously identified in A. squamosa seeds, which showed anthelmintic activity against Haemonchus contortus, the main nematode in small ruminants in Northeastern Brazil 9 . The complete assignment of carbons and hydrogens for the structure of O-methylarmepavine was performed using one-and two-dimensional NMR spectral analysis and by comparison with data from previous studies 10,11 .…”

Section: Discussionsupporting

confidence: 53%

Leishmanicidal activity and cytotoxicity of compounds from two Annonacea species cultivated in Northeastern Brazil

Vila-Nova

Morais

Falcão

et al. 2011

Rev. Soc. Bras. Med. Trop.

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Introduction: Visceral leishmaniasis is endemic in 88 countries, with a total of 12 million people infected and 350 million at risk. In the search for new leishmanicidal agents, alkaloids and acetogenins isolated from leaves of Annona squamosa and seeds of Annona muricata were tested against promastigote and amastigote forms of Leishmania chagasi. Methods: extracts of A. squamosa leaves and A. muricata seeds were extracted with 10% phosphoric acid and organic solvents to obtain the alkaloid and acetogenin-rich extracts. These extracts were chromatographed on a silica gel column and eluted with a mixture of several solvents in crescent order of polarity. The compounds were identified by spectroscopic analysis. The isolated compounds were tested against Leishmania chagasi, which is responsible for American visceral leishmaniasis, using the MTT test assay. The cytotoxicity assay was evaluated for all isolated compounds, and for this assay, RAW 264.7 cells were used. Results: O-methylarmepavine, a benzylisoquinolinic alkaloid, and a C 37 trihydroxy adjacent bistetrahydrofuran acetogenin were isolated from A. squamosa, while two acetogenins, annonacinone and corossolone, were isolated from A. muricata. Against promastigotes, the alkaloid showed an IC 50 of 23.3 µg/mL, and the acetogenins showed an IC 50 ranging from 25.9 to 37.6 µg/mL; in the amastigote assay, the IC 50 values ranged from 13.5 to 28.7 µg/mL. The cytotoxicity assay showed results ranging from 43.5 to 79.9 µg/mL. Conclusions: These results characterize A. squamosa and A. muricata as potential sources of leishmanicidal agents. Plants from Annonaceae are rich sources of natural compounds and an important tool in the search for new leishmanicidal therapies.

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Section: Discussionsupporting

confidence: 53%

Leishmanicidal activity and cytotoxicity of compounds from two Annonacea species cultivated in Northeastern Brazil

Vila-Nova

Morais

Falcão

et al. 2011

Rev. Soc. Bras. Med. Trop.

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“…In another study, C37 trihydroxy adjacent bistetrahydrofuran acetogenin compound isolated from seeds ethyl acetate extract of A. squamosa inhibited 90% egg hatching of H. contortus at 25 mg ml −1 (Souza et al 2008). Although the A. squamosa bark methanol extract showed 100% efficiency on egg hatching and larval development of H. contortus, the concentrations used to obtain these results were high, 25 mg/ml, respectively, compared with albendazole (0.075 mg/ml) and ivermectin (0.025 mg/ml) which were used as positive controls.…”

Section: Resultsmentioning

confidence: 96%

Anthelmintic activity of botanical extracts against sheep gastrointestinal nematodes, Haemonchus contortus

Kamaraj¹,

Rahuman²,

Elango³

et al. 2010

Parasitol Res

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The source of chemical anthelmintics (levamisole, flubendazole, and thiabendazole) had limited the success of gastrointestinal nematodiasis control in sheep and goats and thus awakened interest in the study of medicinal plant extracts as alternative sources of anthelmintics. The egg hatching and larvicidal effect of indigenous plant extracts were investigated against the sheep parasite, Haemonchus contortus. The purpose of the present study was to assess the efficacy of leaf, bark, and seed ethyl acetate, acetone and methanol extracts of Andrographis paniculata (Burm.f.) Wall. ex Nees., Anisomeles malabarica (L.) R. Br., Annona squamosa L., Datura metel L., and Solanum torvum Swartz were tested against the parasitic nematode of small ruminants H. contortus using egg hatch assay (EHA) and larval development assay (LDA). The assays were run in 24-well cell culture plates at room temperature with five replicates. All plant extracts showed moderate parasitic effects after 48 and exposure for egg hatching and LDA, respectively; however, 100% egg hatching and larvicidal inhibition were found in the methanol extracts of A. paniculata, A. squamosa, D. metel, and S. torvum at 25 mg/ml and the effect was similar to positive control of Albendazole (0.075 mg/ml) and Ivermectin (0.025mg/ml) against H. contortus, respectively. The EHA result showed the ED(50) of methanol extracts of A. paniculata and D. metel, which were 2.90 and 3.08 mg/ml, and in larval development assay, the ED(50) was 4.26 and 3.86 mg/ml, respectively. These effects remain to be confirmed through in vivo studies.

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“…The main active acetogenins are asimicin, trilobacin, and bullatacin, found in the bark of stems (McLaughlin 2008). Extracts made of leaves or seeds of Annona senegalensis and Annona squamosa had in vitro anthelmintic activity against H. contortus (Alawa et al 2003;Souza et al 2008).…”

Section: Introductionmentioning

confidence: 99%

In vitro trematocidal effects of crude alcoholic extracts of Artemisia annua, A. absinthium, Asimina triloba, and Fumaria officinalis

Ferreira¹,

Peaden²,

Keiser

2011

Parasitol Res

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Trematode infections negatively affect human and livestock health, and threaten global food safety. The only approved human anthelmintics for trematodiasis are triclabendazole and praziquantel with no alternative drugs in sight. We tested six crude plant extracts against adult Schistosoma mansoni, Fasciola hepatica, and Echinostoma caproni in vitro. Mortality was best achieved by ethanolic extracts of Artemisia annua (sweet Annie), Asimina triloba (paw-paw), and Artemisia absinthium (wormwood) which, at 2 mg/mL, killed S. mansoni and E. caproni in 20 h or less (except for wormwood), F. hepatica between 16 and 23 h (sweet Annie), or 40 h (paw-paw). Some extracts were active at 0.2 mg/mL and 20 μg/mL, although more time was required to kill trematodes. However, aqueous A. annua and methanol extracts of Fumaria officinalis had no activity. Chromatographic analysis of the three best extracts established that A. annua and A. triloba extracts contained bioactive artemisinin and acetogenins (asimicin and bullatacin), respectively. The anthelmintic activity of our extracts at such low doses indicates that their anthelmintic activity deserves further testing as natural alternative controls for parasites of both animals and humans. Our results also support recent evidence that synergistic effects of multiple bioactive compounds present in crude plant extracts is worth exploring.

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Anthelmintic acetogenin from Annona squamosa L. Seeds

Cited by 32 publications

References 16 publications

Leishmanicidal activity and cytotoxicity of compounds from two Annonacea species cultivated in Northeastern Brazil

Leishmanicidal activity and cytotoxicity of compounds from two Annonacea species cultivated in Northeastern Brazil

Anthelmintic activity of botanical extracts against sheep gastrointestinal nematodes, Haemonchus contortus

In vitro trematocidal effects of crude alcoholic extracts of Artemisia annua, A. absinthium, Asimina triloba, and Fumaria officinalis

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