Isolation, synthesis, and biological activity of tomentosenol A from the leaves of Rhodomyrtus tomentosa
Isolation, synthesis, and biological activity of tomentosenol A from the leaves of Rhodomyrtus tomentosa
复制标题
毛桃金娘叶中毛桃醇A的分离、合成及生物活性
DOI：
10.1039/c6ra01594h
复制
发表时间：
2016-01-01
期刊：
影响因子：
3.9
通讯作者：
Qiu, Sheng-Xiang
中科院分区：
文献类型：
--
作者：
Liu, Hong-Xin;Zhang, Wei-Min;Qiu, Sheng-Xiang
Tomentosenol A (1) 以及一对差向异构体 4S-focifolidione (2) 和 4R-focifolidione (3) 从毛白桃金娘 (Rhodomyrtus tomentosa) 的叶子中分离出来。 1是新的类萜类的第一个例子，具有独特的骨架，含有游离的合果酸和萜类化合物单元，并表现出优异的抗菌和细胞毒活性。 1的绝对构型是通过1和预定的2之间的化学转化明确确定的。与先前报道的类萜生物合成中所体现的常见杂狄尔斯-阿尔德环加成相反，Alder-ene反应被认为是解释1生物合成的关键转化，并通过仿生全合成证实了这一点。
Tomentosenol A (1), along with a pair of epimers, 4S-focifolidione (2) and 4R-focifolidione (3), were isolated from the leaves of Rhodomyrtus tomentosa. 1 was the first example of a new meroterpenoid class with a unique skeleton that contained a free syncarpic acid coupled with a terpenoid unit, and showed excellent antimicrobial and cytotoxic activities. The absolute configuration of 1 was unambiguously determined by a chemical conversion between 1 and the predetermined 2. In contrast to the common hetero Diels–Alder cycloaddition embodied in previously reported meroterpenoid biosynthesis, an Alder-ene reaction was proposed as the key transformation to account for the biosynthesis of 1, which was confirmed by a biomimetic total synthesis.