Abstract
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 G2/M cell cycle arrest in HepG2 cells. These data suggest that X. laevigata is a potential source for cytotoxic alkaloids.
Highlights
IntroductionThe 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]
19 alkaloids were isolated from the stem of X. laevigata, and their in vitro cytotoxic activities towardsoftumor cell lines cells were investigated
X. non-tumor laevigata resulted in the isolation of 19 alkaloids, including 11 aporphines, namely, ( ́)-oemerine [8], (+)-anonaine [9], (+)-glaucine [10], (+)-xylopine [11], 2
Summary
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 freshMolecules fruits 2016, contained limonene, α-pinene and β-pinene as the major compounds [6].2 ofMoreover, 21, 890 isoquinoline alkaloids were found in its leaves [7]. D, bicyclogermacrene and trypanocidal, antifungal, antioxidant, antitumor, anti-inflammatory and (E)-caryophyllene as the major constituents [1,3,4,5]. 19 alkaloids were isolated from the stem of X. laevigata, limonene, α-pinene and β-pinene as the major compounds [6]. The terpenoids and essential oil exhibited trypanocidal, larvicidal, antifungal, antibacterial, antioxidant, antitumor, anti-inflammatory and antinociceptive activities
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