Chemical Composition of the Essential Oil from the Fresh Fruits of <i>Xylopia Laevigata</i> and its Cytotoxic Evaluation

Costa, Emmanoel V.; Silva, Thanany Brasil da; Costa, Cinara O. d´S.; Soares, Milena Botelho Pereira; Bezerra, Daniel Pereira

doi:10.1177/1934578x1601100324

Cited by 6 publications

(4 citation statements)

References 9 publications

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“…The in vitro cytotoxic activity of the EO from fresh fruits of Xylopia laevigata and its main constituents (limonene, α-pinene, and β-pinene) was evaluated against four tumor cell lines (mouse melanoma, human hepatocellular carcinoma, human promyelocytic leukemia, and chronic myelocytic leukemia) and non-tumor cells (human peripheral blood mononuclear cells). Neither the EO nor its major constituents showed cytotoxic activity (IC 50 > 25.0 µg•mL −1 ) [77].…”

Section: Antiproliferative and Cytotoxic Activitiesmentioning

confidence: 90%

Essential Oils from Annonaceae Species from Brazil: A Systematic Review of Their Phytochemistry, and Biological Activities

Cascaes

Carneiro

Nascimento

et al. 2021

IJMS

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The present work involves a systematic review of the chemical composition and biological effects of essential oils from the Annonaceae species collected in Brazil from 2011 to 2021. Annonaceae is one of the most important botanical families in Brazil, as some species have economic value in the market as local and international fruit. In addition, the species have useful applications in several areas—for instance, as raw materials for use in cosmetics and perfumery and as medicinal plants. In folk medicine, species such as Annona glabra L. and Xylopia sericea A. St.-Hil. are used to treat diseases such as rheumatism and malaria. The species of Annonaceae are an important source of essential oils and are rich in compounds belonging to the classes of mono and sesquiterpenes; of these compounds, α-pinene, β-pinene, limonene, (E)-caryophyllene, bicyclogermacrene, caryophyllene oxide, germacrene D, spathulenol, and β-elemene are the most abundant. The antimicrobial, anti-inflammatory, antileishmania, antioxidant, antiproliferative, cytotoxic, larvicidal, trypanocidal, and antimalarial activities of essential oils from the Annonaceae species in Brazil have been described in previous research, with the most studies on this topic being related to their antiproliferative or cytotoxic activities. In some studies, it was observed that the biological activity reported for these essential oils was superior to that of drugs available on the market, as is the case of the essential oil of the species Guatteria punctata (Aubl.) R. A. Howard., which showed a trypanocidal effect that was 34 times stronger than that of the reference drug benznidazol.

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Section: Antiproliferative and Cytotoxic Activitiesmentioning

confidence: 90%

Essential Oils from Annonaceae Species from Brazil: A Systematic Review of Their Phytochemistry, and Biological Activities

Cascaes

Carneiro

Nascimento

et al. 2021

IJMS

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“…The chemical composition of essential oil from the leaves of X. laevigata included γ-muurolene, δ-cadinene, germacrene B, α-copaene, germacrene D, bicyclogermacrene and ( E )-caryophyllene as the major constituents [1,3,4,5]. The essential oil from its fresh fruits contained limonene, α-pinene and β-pinene as the major compounds [6]. Moreover, isoquinoline alkaloids were also found in its leaves [7].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Alkaloids from the Stem of Xylopia laevigata

et al. 2016

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Xylopia laevigata (Annonaceae), known locally as "meiú" or "pindaíba", is widely used in folk medicine in Northeastern Brazil. In the present work, we performed phytochemical analyses of the stem of X. laevigata, which led to the isolation of 19 alkaloids: (´)-roemerine, (+)-anonaine, lanuginosine, (+)-glaucine, (+)-xylopine, oxoglaucine, (+)-norglaucine, asimilobine, (´)-xylopinine, (+)-norpurpureine, (+)-N-methyllaurotetanine, (+)-norpredicentrine, (+)-discretine, (+)-calycinine, (+)-laurotetanine, (+)-reticuline, (´)-corytenchine, (+)-discretamine and (+)-flavinantine. The in vitro cytotoxic activity toward the tumor cell lines B16-F10 (mouse melanoma), HepG2 (human hepatocellular carcinoma), K562 (human chronic myelocytic leukemia) and HL-60 (human promyelocytic leukemia) and non-tumor peripheral blood mononuclear cells (PBMCs) was tested using the Alamar Blue assay. Lanuginosine, (+)-xylopine and (+)-norglaucine had the highest cytotoxic activity. Additionally, the pro-apoptotic effects of lanuginosine and (+)-xylopine were investigated in HepG2 cells using light and fluorescence microscopies and flow cytometry-based assays. Cell morphology consistent with apoptosis and a marked phosphatidylserine externalization were observed in lanuginosine-and (+)-xylopine-treated cells, suggesting induction of apoptotic cell death. In addition, (+)-xylopine treatment caused G 2 /M cell cycle arrest in HepG2 cells. These data suggest that X. laevigata is a potential source for cytotoxic alkaloids.

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“…Kouame et al [ 65 ] found that the EOs of the leaves and fruits of a sample of X. aethopica were also characterized by β-pinene (16.01–20.50%) and α-pinene (10.39–17.77%). Costa et al [ 66 ] identified high levels of α-pinene (28.00 ± 1.50%) and β-pinene (5.50 ± 0.10%) in the EO of the fruit of X. laevigata . Maia et al [ 67 ] stated that α- and β-pinene are the major components of the EO of X. cayennensis , with contents of 29.20% and 16.50%, respectively.…”

Section: Resultsmentioning

confidence: 99%

Chemical Evaluation, Phytotoxic Potential, and In Silico Study of Essential Oils from Leaves of Guatteria schomburgkiana Mart. and Xylopia frutescens Aubl. (Annonaceae) from the Brazilian Amazon

et al. 2023

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The essential oils (EOs) of Guatteria schomburgkiana (Gsch) and Xylopia frutescens (Xfru) (Annonaceae) were obtained by hydrodistillation, and their chemical composition was evaluated by gas chromatography-mass spectrometry (GC/MS). Herbicide activity was measured by analyzing the seed germination percentage and root and hypocotyl elongation of two invasive species: Mimosa pudica and Senna obtusifolia. The highest yield was obtained for the EO of Xfru (1.06%). The chemical composition of Gsch was characterized by the presence of the oxygenated sesquiterpenes spathulenol (22.40%) and caryophyllene oxide (14.70%). Regarding the EO of Xfru, the hydrocarbon monoterpenes α-pinene (35.73%) and β-pinene (18.90%) were the components identified with the highest concentrations. The germination of seeds of S. obtusifolia (13.33 ± 5.77%) showed higher resistance than that of seeds of M. pudica (86.67 ± 5.77%). S. obtusifolia was also more sensitive to the EO of Xfru in terms of radicle (55.22 ± 2.72%) and hypocotyl (71.12 ± 3.80%) elongation, while M. pudica showed greater sensitivity to the EO of Gsch. To screen the herbicidal activity, the molecular docking study of the major and potent compounds was performed against 4-hydroxyphenylpyruvate dioxygenase (HPPD) protein. Results showed good binding affinities and attributed the strongest inhibitory activity to δ-cadinene for the target protein. This work contributes to the study of the herbicidal properties of the EOs of species of Annonaceae from the Amazon region.

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Chemical Composition of the Essential Oil from the Fresh Fruits of Xylopia Laevigata and its Cytotoxic Evaluation

Cited by 6 publications

References 9 publications

Essential Oils from Annonaceae Species from Brazil: A Systematic Review of Their Phytochemistry, and Biological Activities

Essential Oils from Annonaceae Species from Brazil: A Systematic Review of Their Phytochemistry, and Biological Activities

Cytotoxic Alkaloids from the Stem of Xylopia laevigata

Chemical Evaluation, Phytotoxic Potential, and In Silico Study of Essential Oils from Leaves of Guatteria schomburgkiana Mart. and Xylopia frutescens Aubl. (Annonaceae) from the Brazilian Amazon

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