Volume 42, Issue 18 pp. 2180-2186
Concise Report

Hyperlanins A and B, Two Highly Rearranged Meroterpenoids from Hypericum lancasteri

Jin-Qiu You

Jin-Qiu You

Shanghai Frontiers Science Center of Drug Target Identification and Delivery, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai, 200240 China

National Key Laboratory of Innovative Immunotherapy, Shanghai Jiao Tong University, Shanghai, 200240 China

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Yun-Qi Jin

Yun-Qi Jin

Shanghai Frontiers Science Center of Drug Target Identification and Delivery, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai, 200240 China

National Key Laboratory of Innovative Immunotherapy, Shanghai Jiao Tong University, Shanghai, 200240 China

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Meng-Yu Li

Meng-Yu Li

Shanghai Frontiers Science Center of Drug Target Identification and Delivery, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai, 200240 China

National Key Laboratory of Innovative Immunotherapy, Shanghai Jiao Tong University, Shanghai, 200240 China

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Bo-Chao Zhang

Bo-Chao Zhang

Shanghai Jiao Tong University School of Medicine, Shanghai, 200025 China

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Xin-Yu Sun

Xin-Yu Sun

Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203 China

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Chun-Yong Ding

Chun-Yong Ding

Shanghai Frontiers Science Center of Drug Target Identification and Delivery, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai, 200240 China

National Key Laboratory of Innovative Immunotherapy, Shanghai Jiao Tong University, Shanghai, 200240 China

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Jing-Ya Li

Jing-Ya Li

Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203 China

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Ai-Jun Hou

Corresponding Author

Ai-Jun Hou

Shanghai Frontiers Science Center of Drug Target Identification and Delivery, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai, 200240 China

National Key Laboratory of Innovative Immunotherapy, Shanghai Jiao Tong University, Shanghai, 200240 China

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First published: 14 May 2024
Citations: 4

Comprehensive Summary

Hyperlanins A (1) and B (2), two highly rearranged polycyclic polyprenylated acylphloroglucinol (PPAP)-related meroterpenoids based on different new carbon skeletons, were isolated from Hypericum lancasteri. Compound 1 incorporates an unprecedented 5/6/7/5 ring system featuring a 3,13-dioxatetracyclo[9.2.1.12,5.01,8]pentadecane core. Compound 2 possesses a unique compact 6/6/5/6/6/5/6 ring system with a caged tetracyclo[6.2.1.13,8.05,11]dodecane motif. Their structures were established by spectroscopic data, X-ray diffraction, and computational approaches. Both compounds showed anti-inflammatory activity in vitro. Compounds 1 and 2 could decrease the lipopolysaccharide (LPS)-/nigericin-induced IL-1β release in THP-1 cells. Both compounds also showed inhibition in hypoxia-inducible factor-1α (HIF-1α) pathway luciferase reporter assay.

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