Leptosperols A and B, Two Cinnamoylphloroglucinol-Sesquiterpenoid Hybrids from Leptospermum scoparium: Structural Elucidation and Biomimetic Synthesis.

Ji-Hong Gu, Wen-Jing Wang, Jun-Zi Chen, Jun-Shan Liu, Ni-Ping Li, Min-Jing Cheng, Li-Jun Hu, Chuang-Chuang Li, Wen-Cai Ye, Lei Wang

Organic letters 2020 Mar 06

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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.

Citation

Ji-Hong Gu, Wen-Jing Wang, Jun-Zi Chen, Jun-Shan Liu, Ni-Ping Li, Min-Jing Cheng, Li-Jun Hu, Chuang-Chuang Li, Wen-Cai Ye, Lei Wang. Leptosperols A and B, Two Cinnamoylphloroglucinol-Sesquiterpenoid Hybrids from Leptospermum scoparium: Structural Elucidation and Biomimetic Synthesis. Organic letters. 2020 Mar 06;22(5):1796-1800