Isolation, Crystal Structure and Cytotoxic Activity of Natural Maistemonine and Comparison with the

• 作 者: WU Yi YE Qing-Mei QIN Shu-Qin JIANG Ren-Wang
• 机 构: Zhongshan Torch Polytechnic,Zhongshan 528436,China“,”Guangdong Province Key Laboratory of Pharmacody
• 出 处: 结构化学
• 发表日期: 2020年7期
• 关键词: maistemonine isolation crystal structure cytotoxic comparison synthesis

The title compound maistemonine (1) was isolated from the total alkaloid fraction of the 95％ ethanol extract of the roots of Stemona japonica,followed by preparative HPLC and recrystallization from a mixture of n-hexane and ethyl acetate.The crystal structure of 1,C23H29NO6,was determined by single-crystal X-ray diffraction analysis.The crystal belongs to orthorhombic system,space group P212121 with a =8.5698(6),b =14.0460(11),c =17.8815(17) (A),V=2152.4(3) (A)3,Z=4,Mr=415.47,Dc =1.282 g/cm3,λ =0.71079(A),μ =0.092 cm-1,F(000) =888,S =0.995,R =0.0535 and wR =0.1067.A total of 5136 unique reflections were collected,of which 3523 were observed (I ＞ 2σ(I)).The absolute configuration of 1 could be assigned by referring to the conserved configuration of the methyl groups at C(2).Compound 1 shows mild cytotoxic activity against the prostate cancer cells LNCaP and PC3 with the IC50 values of 29.4 ± 2.3 and 46.6 ± 3.1 μM,respectively.It is noteworthy that the natural maistemonine (1) is different from the synthetic compound which was a racemic with the triclinic space group P(1).The lactone rings E from the natural and synthetic 1 are almost perpendicular to each other when overlapping the remaining parts of the molecules.