1. Structurally diverse isoquinoline alkaloids from the barks of Alangium salviifolium (L. f.) Wangerin and their cytotoxicity.
- Author
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Wei, Yan-Mei, Zhang, Xuan, Cen, Fu-Ling, Du, Yi-Yi, Liu, Yuan-Ling, Han, Qiao-Yuan, Yu, Zhang-Xin, and Chen, Guang-Ying
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CYTOTOXINS , *ISOQUINOLINE alkaloids , *ALKALOIDS , *STRUCTURE-activity relationships , *X-ray diffraction , *CELL lines , *DOXORUBICIN - Abstract
Eleven undescribed isoquinoline alkaloids (1 − 8 , 14 , 15 , and 24), along with 19 analogues (9 − 13 , 16 − 23 , and 25 − 30) were isolated from the barks of Alangium salviifolium. The structures of the undescribed compounds were elucidated through the analysis of their HR-ESI-MS, 1D and 2D NMR, IR, UV, and X-ray diffraction. The absolute configuration of 8 was established via the ECD calculation. Notably, compounds 1 / 2 and 3 / 4 were two pairs of C-14 epimers. The isolated alkaloids were evaluated for their cytotoxicity against various cancer cell lines, including SGC-7901, HeLa, K562, A549, BEL-7402, HepG2, and B16, β -carboline-benzoquinolizidine (14 − 22) and cepheline-type (24 − 28) alkaloids exhibited remarkable cytotoxicity, with IC 50 values ranging from 0.01 to 48.12 μM. Remarkably, compounds 17 and 21 demonstrated greater cytotoxicity than the positive control doxorubicin hydrochloride. Furthermore, a significant proportion of these bioactive alkaloids possess a C-1′ epimer configuration. The exploration of their structure-activity relationship holds promise for directing future investigations into alkaloids derived from Alangium , potentially leading to novel insights and therapeutic advancements. [Display omitted] • Eleven undescribed alkaloids were identified from Alangium salviifolium. • All structures were elucidated by spectroscopic, X-ray crystallographic data, and ECD analyses. • β -carboline-benzoquinolizidine and cepheline-type alkaloids exhibited cytotoxicity. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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