Alkaloids with cytotoxic activities from Zanthoxylum nitidum

IF 2.6 3区医学 Q3 CHEMISTRY, MEDICINAL

Fitoterapia Pub Date : 2025-09-29 DOI:10.1016/j.fitote.2025.106913

Wei Wei , Jing-Hui Yin , Bang-Yong Wang , Lin-Lin Luo , Xiao-Xiao Mo , Qin-Gang Tan

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Abstract

Two previously undescribed alkaloids, 8-O-demethylmaclekarpine D (1) and zanthonitine (2), along with a pair of inseparable rotamers, 4-hydroxyl-beecheyamide (3a) and (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenethyl)-N-methylacrylamide (3b), were isolated from Zanthoxylum nitidum. These compounds were accompanied by 35 known alkaloids, including benzophenanthridines (4–21), quinolines (22−31), aporphines (32–35) and other structural types (36–38). Structural elucidation was achieved through comprehensive spectroscopic analyses, including NMR, HRESIMS, X-ray crystallography, ECD and calculated ¹³C NMR DP4+ analysis. Cytotoxicity evaluation revealed compounds 6, 7, 18 and 33 (IC₅₀ = 7.29–22.90 μM) exhibited potent inhibitory effects on the proliferation of HepG2 cells, outperforming the efficacy of doxorubicin (IC₅₀ = 28.92 ± 0.48 μM). Similarly, compounds 9, 16 and 21 (IC₅₀ = 21.77–25.13 μM) suppressed SW480 cells, superior to doxorubicin (IC₅₀ = 31.15 ± 0.24 μM).

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花椒中具有细胞毒活性的生物碱。

从nitidum花椒中分离出了两个先前未被描述的生物碱，8-O-demethylmaclekarpine D(1)和zananthonitine(2)，以及一对不可分离的旋体，4-羟基-beecheyamide （3a）和(E)-3-（4-羟基-3-甲氧基苯基）- n -（4-甲氧基苯基）- n -甲基丙烯酰胺（3b）。这些化合物含有35种已知的生物碱，包括苯并苯胺类（4-21）、喹啉类（22-31）、阿啡类（32-35）和其他结构类型（36-38）。通过全面的光谱分析，包括NMR， hresms， x射线晶体学，ECD和计算的13CNMR DP4+分析，实现了结构解析。细胞毒性评价显示，化合物6、7、18和33 （IC50 = 7.29-22.90 μM）对HepG2细胞的增殖具有较强的抑制作用，优于阿霉素（IC50 = 28.92 ± 0.48 μM）。同样，化合物9、16和21 （IC50 = 21.77 ~ 25.13 μM）对SW480细胞的抑制作用优于阿霉素（IC50 = 31.15 ± 0.24 μM）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Fitoterapia 医学-药学

CiteScore

5.80

自引率

2.90%

发文量

198

审稿时长

1.5 months

期刊介绍： Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.