Cytotoxic Alkaloids from the Stem of Xylopia laevigata
AbstractXylopia 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. View Full-Text
- Supplementary File 1:
Supplementary (PDF, 626 KB)
Share & Cite This Article
Menezes, L.R.A.; Costa, C.O.D.; Rodrigues, A.C.B.C.; Santo, F.R.E.; Nepel, A.; Dutra, L.M.; Silva, F.M.A.; Soares, M.B.P.; Barison, A.; Costa, E.V.; Bezerra, D.P. Cytotoxic Alkaloids from the Stem of Xylopia laevigata. Molecules 2016, 21, 890.
Menezes LRA, Costa COD, Rodrigues ACBC, Santo FRE, Nepel A, Dutra LM, Silva FMA, Soares MBP, Barison A, Costa EV, Bezerra DP. Cytotoxic Alkaloids from the Stem of Xylopia laevigata. Molecules. 2016; 21(7):890.Chicago/Turabian Style
Menezes, Leociley R.A.; Costa, Cinara O.D.; Rodrigues, Ana C.B.C.; Santo, Felipe R.E.; Nepel, Angelita; Dutra, Lívia M.; Silva, Felipe M.A.; Soares, Milena B.P.; Barison, Andersson; Costa, Emmanoel V.; Bezerra, Daniel P. 2016. "Cytotoxic Alkaloids from the Stem of Xylopia laevigata." Molecules 21, no. 7: 890.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.