Magterpenes A–C: Three Meroterpenoids with an Unprecedented 6/6/6/6/6 Polycyclic Skeleton Extracted from Magnolia officinalis Rehd. et Wils

化学 厚朴 立体化学 电喷雾电离 圆二色性 木兰科 高分辨率 质谱法 色谱法 植物 地质学 生物 病理 医学 中医药 替代医学 遥感
作者
Jing-ying Sun,Jie Ma,Sen Zhang,Lingzhi Zhang,Xinyue Tao,Chuang‐Jun Li,Yingda Zang,Ming Ji,Anhua Tao,Dongming Zhang
出处
期刊:Journal of Organic Chemistry [American Chemical Society]
卷期号:89 (12): 8871-8877
标识
DOI:10.1021/acs.joc.4c00739
摘要

Magterpenes A–C (1–3), three unprecedented meroterpenoids featuring a unique 6/6/6/6/6 polycyclic skeleton, were isolated from the ethanol extract of Magnolia officinalis Rehd. et Wils. The compounds were obtained as racemic mixtures that were completely resolved through chiral columns. Their structures were elucidated by extensive analyses of one-dimensional (1D) and 2D nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, chemical calculations of 1H/13C NMR, and electronic circular dichroism calculations. The compounds were constructed via two Diels–Alder reactions in the proposed biosynthetic pathway. All isolates were evaluated for their nephroprotective and hepatoprotective activities. The results demonstrated that (+)-1 and (−)-1 possessed promising nephroprotective activities in a dose-dependent manner, while (−)-2 and (+)-3 exhibited moderate hepatoprotective activities.
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