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Meroterpenoids with bicyclic polyprenylated acylphloroglucinol scaffold and anti-inflammatory activity from Hypericum
Jin-Qiu You1, Yun-Qi Jin2, Yu-Meng Miao3
1Shanghai Frontiers Science Center of Drug Target Identification and Delivery, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai, 200240, People's Republic of China; Department of Pharmacy, The Fourth Affiliated Hospital of Soochow University, Suzhou Dushu Lake Hospital, Medical Center of Soochow University, Suzhou, 215123, People's Republic of China.
Abstract:
Twelve undescribed meroterpenoids possessing bicyclic polyprenylated acylphloroglucinol (BPAP) scaffold, (±)-lancasternoids A-D and lancasternoids E-H, together with fourteen known analogues, were isolated from Hypericum lancasteri (Hypericaceae) and structurally characterized. (±)-Lancasternoids A-D are the first examples of bicyclo[3.2.1]octane-type BPAP meroterpenoids present as enantiomeric pairs, while (±)-lancasternoids A-C incorporate an unprecedented 5-oxatetracyclo[7.5.1.04,9.01,11]pentadecane system. Lancasternoids E-H are two pairs of epimers with [3.3.1]-type BPAP scaffold. Some of the isolates showed inhibition in hypoxia-inducible factor-1α (HIF-1α) responsive element (HRE) luciferase assay, and uraloidin A further decreased the lipopolysaccharide (LPS)-induced pro-inflammatory factor IL-1β expression level in RAW 264.7 cells.
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