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. 2014 Mar 10;19(3):3055-67.
doi: 10.3390/molecules19033055.

Five new alkaloids from the stem bark of Daphniphyllum macropodum

Yunyang Lu  1 , Kai Gao  2 , Xiaoyang Wang  3 , Wei Zhang  4 , Ning Ma  5 , Haifeng Tang  6
Affiliations

Five new alkaloids from the stem bark of Daphniphyllum macropodum

Yunyang Lu et al. Molecules. .

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.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of compounds 1–9.
Figure 2
Figure 2
Selected 2D NMR correlations of daphnicyclidin M (1).
Figure 3
Figure 3
Key NOESY correlations of daphnicyclidin M (1).
Figure 4
Figure 4
Selected 2D NMR correlations of calyciphylline Q (3).
Figure 5
Figure 5
Key NOESY correlations of calyciphylline Q (3).
See this image and copyright information in PMC

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