The styrylpyrone dehydrogoniothalamin (1) and two of its dimers (2 and 3) were isolated from the leaves of Aniba heringeri (Lauraceae). Compound 3 is new, while 1 and 2 are being reported for the first time in this species. Structures were determined by 1D- and 2D-NMR spectroscopy, mass spectrometry, and optical rotation data. Cytotoxic effects and selectivity indices were evaluated in five neoplastic cell lines—PC-3 (prostate), 786-0 (renal), HT-29 (colon), MCF-7, and MDA-MB-231 (breast)—and a non-neoplastic cell line, (NIH/3T3, murine fibroblast). Compound 1 inhibited cell growth by 50% (GI₅₀) at concentrations in the 90.4-175.7 μM range, while 2 proved active against MCF-7 and MDA-MB-231 breast cells (GI₅₀ = 12.24, and 34.22 μM, respectively). Compound 3 showed strong cytotoxicity (GI₅₀ = 4.4 μM) against MDA-MB-231 (an established basal triple-negative breast carcinoma (TNBC) cell line), with a high selective index of 35. This compound was subsequently evaluated for apoptosis induction in MDA-MB-231 cells, using GI₅₀ and 50% lethal concentrations (LC₅₀). Flow cytometry analysis showed that at LC₅₀ compound 3 induced cell death with phosphatidylserine externalization and caspase-3 activation. Apoptotic genes were measured by RT-qPCR, revealing an upregulation of BAX, with an increase in expression of the BAX/BCL2 ratio in treated cells. Fluorescence microscopy disclosed morphological changes related to apoptosis. Overall, these findings showed compound 3 to be a promising prototype against TNBC cells that tend to respond poorly to conventional therapies.

从Aniba heringeri（樟科）的叶子中分离出苯乙烯吡喃酮脱氢角草胺（1）及其两个二聚体（2和3）。化合物3是新的，而1和2是该物种中首次报道。结构由 1D-和 2D-​​NMR 光谱、质谱和旋光数据确定。在五种肿瘤细胞系——PC-3（前列腺）、786-0（肾）、HT-29（结肠）、MCF-7 和 MDA-MB-231（乳腺）——以及一种非肿瘤细胞系，（NIH/3T3，鼠成纤维细胞）。化合物1抑制细胞生长 50% (GI ₅₀) 浓度在 90.4-175.7 μM 范围内，而2证明对 MCF-7 和 MDA-MB-231 乳腺细胞有活性（GI _{50 分别}为 12.24 和 34.22 μM）。化合物3对 MDA-MB-231（一种已建立的基底三阴性乳腺癌 (TNBC) 细胞系）显示出强烈的细胞毒性（GI ₅₀ = 4.4 μM），具有 35 的高选择指数。随后评估了该化合物的细胞凋亡诱导在 MDA-MB-231 细胞中，使用 GI ₅₀和 50% 致死浓度 (LC ₅₀ )。流式细胞术分析表明，在 LC _{50 时，}化合物3通过磷脂酰丝氨酸外化和 caspase-3 激活诱导细胞死亡。通过 RT-qPCR 测量凋亡基因，显示BAX上调，处理细胞中BAX / BCL2比率的表达增加。荧光显微镜揭示了与细胞凋亡相关的形态学变化。总体而言，这些发现表明化合物3是一种有前景的原型，可以对抗对常规疗法反应不佳的 TNBC 细胞。