Amomaxyz A and B, Sesquiterpene-Indole Alkaloids from Fruits of Amomum maximum Roxb

Two unprecedented 4/9/5-membered ring sesquiterpene-indole alkaloids, amomaxyz A (1) and B (2), along with one known compound caryolane-1,9β-diol (3), were isolated from the fruit of Amomum maximum Roxb. Their structures and absolute configurations were elucidated through comprehensive spectroscopic analyses, including NMR, electronic circular dichroism (ECD), X-ray single-crystal diffraction, and DP4 probability analysis of calculated NMR data. Biological evaluation revealed distinct anti-inflammatory and anticancer activities. 1 demonstrated dose-dependent anti-inflammatory activity by suppressing NO release in LPS/IFN-γ-activated RAW264.7 macrophages (25.9% at 10 μM, 29.9% at 20 μM; P 2 and 3 exhibited weaker effects. Moreover, 1 (IC50 = 30.62 μM) and 2 (IC50 = 23.43 μM) showed moderate inhibitory effects against HepG2 cells, which reveals the potential of their biological activity.本研究从益智（Amomum maximum Roxb.）的果实中分离得到2个前所未有的4/9/5元环倍半萜吲哚类生物碱amomaxyz A（1）与B（2），以及1个已知化合物石竹烷-1,9β-二醇（caryolane-1,9β-diol，3）。其化学结构与绝对构型通过综合波谱分析手段得以解析，涵盖核磁共振波谱（nuclear magnetic resonance, NMR）、电子圆二色谱（electronic circular dichroism, ECD）、X射线单晶衍射（X-ray single-crystal diffraction）以及计算NMR数据的DP4概率分析（DP4 probability analysis）。生物学活性评价结果显示，该类化合物兼具显著的抗炎与抗肿瘤活性：化合物1可通过抑制脂多糖/干扰素-γ（lipopolysaccharide/interferon-γ, LPS/IFN-γ）激活的RAW264.7巨噬细胞释放一氧化氮（nitric oxide, NO），呈现剂量依赖性抗炎活性，在10 μM浓度下抑制率为25.9%，20 μM浓度下抑制率为29.9%（P<0.05）；化合物2与3的抗炎活性相对较弱。此外，化合物1（半数抑制浓度IC50=30.62 μM）与2（IC50=23.43 μM）对HepG2细胞展现出中等强度的增殖抑制活性，揭示了其生物学活性的应用潜力。