Leptosperols A and B, Two Cinnamoylphloroglucinol–Sesquiterpenoid Hybrids from <i>Leptospermum scoparium</i>: Structural Elucidation and Biomimetic Synthesis
Ji‐Hong Gu, Wen‐Jing Wang, Jun-Zi Chen, Jun-Shan Liu, Ni-Ping Li, Min-Jing Cheng, Lijun Hu, Chuang‐Chuang Li, Wen‐Cai Ye, Lei Wang
Abstract
Leptosperols A and B (1 and 2), two cinnamoylphloroglucinol–sesquiterpenoid hybrids featuring unprecedented 1-benzyl-2-(2-phenylethyl) cyclodecane and 2-benzyl-3-phenylethyl decahydronaphthalene backbones, along with their biosynthetic precursor (3), were isolated from Leptospermum scoparium. Compounds 1 and 2 represent the first example of phloroglucinol derivatives biogenetically constructed by a De Mayo reaction. The biomimetic synthesis of leptosperol B (2) was achieved using the proposed biosynthetic pathway. In addition, compounds 1 and 2 showed significant anti-inflammatory effects in zebrafish acute inflammatory models.