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

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. Compou...

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Bibliographic Details
Published in:Organic letters 2020-03, Vol.22 (5), p.1796-1800
Main Authors: Gu, Ji-Hong, Wang, Wen-Jing, Chen, Jun-Zi, Liu, Jun-Shan, Li, Ni-Ping, Cheng, Min-Jing, Hu, Li-Jun, Li, Chuang-Chuang, Ye, Wen-Cai, Wang, Lei
Format: Article
Language:English
Subjects:
Biomimetics
Leptospermum - chemistry
Molecular Structure
Phloroglucinol - analogs & derivatives
Phloroglucinol - chemistry
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00109