Hyperlanins A and B, Two Highly Rearranged Meroterpenoids from Hypericum lancasteri
Jin-Qiu You , Yun-Qi Jin , Meng-Yu Li , Bo-Chao Zhang , Xin-Yu Sun , Chun-Yong Ding , Jing-Ya Li , Ai-Jun Hou
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (18) : 2180 -2186.
Hyperlanins A and B, Two Highly Rearranged Meroterpenoids from Hypericum lancasteri
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[9.2.1.1 2, 5.0 1, 8]pentadecane core. Compound 2 possesses a unique compact 6/6/5/6/6/5/6 ring system with a caged tetracyclo[6.2.1.1 3, 8.0 5, 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-1 β release in THP-1 cells. Both compounds also showed inhibition in hypoxia-inducible factor-1 α (HIF-1 α) pathway luciferase reporter assay.
Natural products / Hypericum lancasteri / Meroterpenoids / Structure elucidation / Inflammation
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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