Stem bark, root bark, and leaf extracts of Erythroxylum pungens were subjected to phytochemical analysis. N,N-dimethyltryptamine (DMT) was isolated and characterized from E. pungens roots. This unprecedented result is remarkable since no indole alkaloid has been previously reported from Erythroxylaceae so far. Eleven known tropane alkaloids were identified by their mass spectra and 3-(2-methylbutyryloxy)tropan-6,7-diol as well as 3-(2-methylbutyryloxy)nortropan-6,7-diol were isolated and characterized based on mass spectrometry, 1H, 13C, COSY, and NOESY NMR analysis. The complete NMR data are reported for the first time. Inverse Structure-based and Ligand-Based virtual screening were carried out to identify possible targets for 3-(2-methylbutyryloxy)tropan-6,7-diol. The level of cytotoxicity of this tropane alkaloid aliphatic ester was discrete with potencies on the order of 0.3-1.0 mg/mL and better results against HeLa (50% cell viability reduction). Otherwise, atropine (0.3 mg/mL), a Solanaceae tropane alkaloid, and DMT (0.5 mg/mL) from E. pungens roots impaired at 50% the cell viability against HeLa, SiHa, PC3, and 786-0. This study stimulates scientific investigation of the impact of edaphoclimatic features in a semi-arid environment on tropane alkaloid biosynthesis.

中文翻译：

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Erythroxylum pungens OE Shulz 生物碱的分离、光谱表征、分子对接和细胞毒活性

对 Erythroxylum pungens 的茎皮、根皮和叶提取物进行植物化学分析。N，N-二甲基色胺 (DMT) 是从 E. pungens 根中分离和表征的。这一史无前例的结果是显着的，因为迄今为止还没有从赤藓科植物中报道过吲哚生物碱。通过质谱鉴定了 11 种已知的托烷类生物碱，并基于质谱法分离并表征了 3-(2-methylbutyryloxy)tropan-6,7-diol 和 3-(2-methylbutyryloxy)nortropan-6,7-diol 、1H、13C、COSY 和 NOESY NMR 分析。首次报道完整的核磁共振数据。进行了基于反向结构和基于配体的虚拟筛选，以确定 3-(2-methylbutyryloxy)tropan-6,7-diol 的可能目标。这种托烷生物碱脂肪族酯的细胞毒性水平是离散的，效力约为 0.3-1.0 毫克/毫升，对 HeLa 的效果更好（细胞活力降低 50%）。否则，阿托品 (0.3 毫克/毫升)、茄科托烷生物碱和来自 E. pungens 根的 DMT (0.5 毫克/毫升) 对 HeLa、SiHa、PC3 和 786-0 的细胞活力降低了 50%。这项研究激发了对半干旱环境中土壤气候特征对托烷生物碱生物合成的影响的科学调查。