State Key Laboratory of Component-based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, PR China.
School of Chinese Materia Medica, and Tianjin Key Laboratory of Therapeutic Substance of Traditional Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, PR China.
Bioorg Chem. 2024 Sep;150:107527. doi: 10.1016/j.bioorg.2024.107527. Epub 2024 Jun 4.
Two protoberberine alkaloids with a unique C skeleton, named xanthiumines A (1) and B (2), respectively, were isolated from the fruits of Xanthium sibiricum Patr. Their structures including absolute configurations were unequivocally established by the comprehensive NMR and MS spectroscopic data analysis together with gauge-independent atomic orbital (GIAO) NMR calculations, and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 are the first examples of natural protoberberine alkaloid with a phenolic acid group at C-13a. Their plausible biosynthetic pathway was proposed on the basis of the coexisting alkaloid monomer as the precursor. Furthermore, the effects and related molecular mechanism of compound 1 on hepatic lipid accumulation were also investigated in oleic acid (OA)-treated HepG2 cells.
从苍耳果实中分离得到两个具有独特 C 骨架的原小檗碱生物碱，分别命名为苍耳宁 A（1）和 B（2）。通过综合 NMR 和 MS 光谱数据分析以及无规坐标原子轨道（GIAO）NMR 计算和电子圆二色谱（ECD）计算，明确了它们的结构包括绝对构型。化合物 1 和 2 是首例在 C-13a 位含有酚酸基团的天然原小檗碱生物碱。基于共存的生物碱单体作为前体，提出了它们的可能生物合成途径。此外，还研究了化合物 1 在油酸（OA）处理的 HepG2 细胞中对肝脂堆积的作用及其相关分子机制。
