Citation: Chunmao Yuan, Yanrong Zeng, Lei Huang, Yu Mou, Jun Jin, Ping Yi, Yanmei Li, Xiaojiang Hao. Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum[J]. Chinese Chemical Letters, ;2025, 36(3): 109859. doi: 10.1016/j.cclet.2024.109859 shu

Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum

Chunmao Yuan ^{a, b, c, 1} ,
Yanrong Zeng ^{a, c, e, 1} ,
Lei Huang ^{a, b, c, *,} ,
Yu Mou ^{a, b, c} ,
Jun Jin ^{a, b, c} ,
Ping Yi ^{a, c} ,
Yanmei Li ^{a, b, c, *,} ,
Xiaojiang Hao ^{a, b, c, d, *,}

a.
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China
b.
School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang 550025, China
c.
Natural Products Research Center, Guiyang 550014, China
d.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming 650201, China
e.
School of Chinese Ethnic Medicine, Guizhou Minzu University, Guiyang 550025, China

xinyanghuanglei@163.com

liyanmei518@hotmail.com

haoxj@mail.kib.ac.cn

Received Date: 2 February 2024
Revised Date: 28 March 2024
Accepted Date: 3 April 2024
Available Online: 4 April 2024

Figures(4)

Hymoins A–C (1–3), three unusual polycyclic polyprenylated acylphloroglucinols (PPAPs) were isolated from the flowers of Hypericum monogynum. Hymoin A features the first intriguing 6/5/5/5/7 pentacyclic caged PPAP. Hymoin B is characterized by an unprecedented rearranged 5/6/8 tricyclic ring system, while hymoin C represents the first rearranged PPAP with a fantastic spirocyclic 5/6/7 ring system. Their structures were established by extensive spectroscopic analysis, X-ray crystallography, and computational methods. The plausible biosynthetic routes for the compounds were also proposed. In oleic acid (OA)-induced HepG2 cells, all compounds exhibited significant lipid-lowering activity at the concentrations of 2–8 µmol/L. Further mechanistic study implied that compound 1 exhibited excellent lipid-lowering activity in OA-induced HepG2 cells through inhibiting the proteins of free fatty acids synthesis and improving lipidolysis.
- Hypericum monogynum,
- Polycyclic polyprenylated acylphloroglucinols,
- Structure elucidation,
- Lipid-lowering activity,
- Mechanistic study
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沈阳化工大学材料科学与工程学院沈阳 110142