Glutarimide alkaloids and terpenoids from Croton pullei var. glabrior Lanj.

Barbosa, Patrícia; Abreu, Alcicley da S.; Batista, Elenilze F.; Guilhon, Giselle Maria Skelding Pinheiro; Müller, Adolfo Henrique; Arruda, Mara Silvia Pinheiro; Santos, Lourivaldo S.; Arruda, Alberto C.; Secco, Ricardo de S.

doi:10.1016/j.bse.2007.04.006

Cited by 17 publications

(18 citation statements)

References 22 publications

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“…Part of the hexane extract of the stem (20 g) was subjected to several column chromatography and thin layer chromatography on silica gel and eluted with hexane, EtOAc, and MeOH in increasing order of polarity, yielding 994 mg of Julocrotine. An alkaloid, julocrotine (2-[N-(2-methylbutanolyl)]-N-phenylethylglutarimide) (Fig.1), was one of the compounds isolated during plant extraction and fractioning (Barbosa et al 2007;Moreira et al 2008). One milligram of the drug was dissolved in 10 μL of chloroform and diluted in the culture medium (DMEM) and 1 mg/mL was used as the standard solution for the assay.…”

Section: Methodsmentioning

confidence: 99%

Activity of the julocrotine, a glutarimide alkaloid from Croton pullei var. glabrior, on Leishmania (L.) amazonensis

Guimarães

Rodrigues

Marinho³

et al. 2010

Parasitol Res

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The antiproliferative effect of julocrotine, an alkaloid isolated from Croton pullei var. glabrior (Euphorbiaceae), was studied in the macrophage amastigote and promastigote stages of the protozoan Leishmania (L.) amazonensis, which causes cutaneous leishmaniasis in the New World. Julocrotine showed a dose-dependent effect against the amastigote and promastigote forms, where 79 μM julocrotine inhibited promastigote growth by 54%, with an IC50 of 67 μM. To analyze the antiamastigote activity of the drug, murine peritoneal macrophages infected with L. amazonensis promastigotes were treated with different concentrations of julocrotine. An 80% inhibition of amastigote development was observed using 79 μM julocrotine for 72 h, with an IC50 of 19.8 μM. In addition, ultrastructural observation of the parasites showed a significant reduction in the number of amastigotes in the parasitophorous vacuoles and morphological changes in promastigotes, such as swelling of the mitochondrion, chromatin condensation, presence of membranous structures near the Golgi complex, and some vesicle bodies in the flagellar pocket. A colorimetric assay (MTT), which measures cytotoxic metabolic activity, showed that macrophages maintain their viability after treatment with the drug. These results suggest that julocrotine effectively inhibits the growth of parasites and does not have any cytototoxic effects on the host cell.

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Section: Methodsmentioning

confidence: 99%

Activity of the julocrotine, a glutarimide alkaloid from Croton pullei var. glabrior, on Leishmania (L.) amazonensis

Guimarães

Rodrigues

Marinho³

et al. 2010

Parasitol Res

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“…This compound was also found to be closely related to crotonimides A and B isolated from the Amazonian C. pullei var. glabrior Lanj [23]. The 1 H and 13 C NMR spectra of this compound, like those of crotonimides A and B, showed resonances for phenylethyl (H-2′ to H-8′) and glutarimide groups (H-2 to H-4) [23] with those for the N-propanoyl and N-(1-methylpropanoyl) substituents in crotonimides A and B, respectively, missing.…”

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confidence: 87%

Alienusolin, a New 4α-Deoxyphorbol Ester Derivative, and Crotonimide C, a New Glutarimide Alkaloid from the Kenyan Croton alienus

et al. 2013

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Two novel compounds, alienusolin, a 4α-deoxyphorbol ester (1), crotonimide C, a glutarimide alkaloid derivative (2), and ten known compounds, julocrotine (3), crotepoxide (4), monodeacetyl crotepoxide (5), dideacetylcrotepoxide, (6), β-senepoxide (7), α-senepoxide (8), (+)-(2S,3R-diacetoxy-1-benzoyloxymethylenecyclohex-4,6-diene (9), benzyl benzoate (10), acetyl aleuritolic (11), and 24-ethylcholesta-4,22-dien-3-one (12) were isolated from the Kenyan Croton alienus. The structures of the compounds were determined using NMR, GCMS, and HRESIMS studies.

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“…The genus Croton is the second largest genus of Euphorbiaceae with over 1300 species, and over 100 species from this genus have been studied phytochemically, resulting in the isolation and identification of more than 200 various types of diterpenoids) [21,22] comprising of different skeleton types such as clerodane (most common), kaurane, cembranoid, halimane, isopimarane, labdane, phorbol and trachylobane [23].…”

Section: Chemotaxonomic Significancementioning

confidence: 99%

NEW DITERPENOIDS FROM THE ROOTS OF Croton hirtus (EUPHORBIACEAE)

Rosandy

Azman

Khalid³

et al. 2018

MJAS

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The root of Croton hirtus was collected at Tanjung Sepat, Banting for study of its chemical compounds. This sample was dried before being ground and extracted using the methanol solvent at room temperature for three days yielding 18.25 gram of crude extract. The crude extracts obtained were analysed using thin layer chromatography (TLC) then fractionated via vacuum column chromatography (VLC) and proceed the isolation using radial chromatography (RC) to get the pure compounds. The pure compounds obtained were elucidated by nuclear magnetic resonance (NMR), Fourier Transform Infrared (FT-IR) and mass spectroscopy to confirm their structures and from that analysis, the compounds were identified as two new compounds naming (-)-5,8-dihydroxyjatrophan-3-one (1) and (+)-14,16,17-trihydroxykauran-1-on (2) with total weight 4.9 mg and 4.5 mg respectively. This two compound were reported for this time on this genus.

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Glutarimide alkaloids and terpenoids from Croton pullei var. glabrior Lanj.

Cited by 17 publications

References 22 publications

Activity of the julocrotine, a glutarimide alkaloid from Croton pullei var. glabrior, on Leishmania (L.) amazonensis

Activity of the julocrotine, a glutarimide alkaloid from Croton pullei var. glabrior, on Leishmania (L.) amazonensis

Alienusolin, a New 4α-Deoxyphorbol Ester Derivative, and Crotonimide C, a New Glutarimide Alkaloid from the Kenyan Croton alienus

NEW DITERPENOIDS FROM THE ROOTS OF Croton hirtus (EUPHORBIACEAE)

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