Abstract
Five new alkaloids, daphnicyclidins M and N (compounds 1 and 2) and calyciphyllines Q–S (compounds 3–5), along with four known ones, paxiphylline C (6), macropodumine B (7), macropodumine C (8) and daphnicyclidin A (9) were isolated from the stem bark of Daphniphyllum macropodum. Calyciphylline Q (3) is the first calyciphylline A derivative possessing a double bond between C-18 and C-19. Their structures and relative configurations were elucidated on the basis of spectroscopic methods, especially 2D NMR techniques. Compounds 1, 2, 8 and 9 exhibited cytotoxic activity against P-388 cells with IC50 values of 5.7, 6.5, 10.3 and 13.8 µM, respectively. Compounds 1 and 2 also showed cytotoxic activity against SGC-7901 cells with IC50 values of 22.4 and 25.6 µM.
Highlights
Plants of genus Daphniphyllum are mainly distributed in southeast of Asia and are well known for producing highly polycyclic and structurally diverse alkaloids, which have drawn a great deal of Molecules 2014, 19 attention from the biogenetic and synthetic points of view [1,2,3,4]
This paper presents the isolation and structural elucidation of the new compounds 1–5, along with their cytotoxic activities against four tumor cell lines, P-388, A-549, SGC-7901 and HL-60
Phytochemical investigation of the stem bark of Daphniphyllum macropodum, lead to the isolation of five new Daphniphyllum alkaloids 1–5, along with four known ones 6–9. Their structures and relative configurations were elucidated on the basis of spectroscopic methods, especially 2D NMR
Summary
Plants of genus Daphniphyllum are mainly distributed in southeast of Asia and are well known for producing highly polycyclic and structurally diverse alkaloids, which have drawn a great deal of Molecules 2014, 19 attention from the biogenetic and synthetic points of view [1,2,3,4]. A great number of Daphniphyllum alkaloids have been isolated and identified, and some of them exhibited significant cytotoxic activity against several human cancer cell lines [5,6,7,8,9,10,11,12,13,14,15,16,17,18,19]. With the purpose of searching for bioactive and structurally unique Daphniphyllum alkaloids, an investigation of the extracts from the stem bark of Daphniphyllum macropudum was conducted, and this resulted in the isolation of five new alkaloids named daphnicyclidins M and N (compounds 1 and 2). This paper presents the isolation and structural elucidation of the new compounds 1–5, along with their cytotoxic activities against four tumor cell lines, P-388 (mouse lymphocytic leukemia), A-549 (human lung carcinoma), SGC-7901 (human gastric carcinoma) and HL-60 (human promyelocytic leukemia)
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