Cyclooxygenase-2 (COX-2) is a significant therapeutic target of chronic inflammatory diseases. Soniiglucinols A–D (1–4), four new polycyclic polyprenylated acylphloroglucinols (PPAPs) with diverse architectures, were isolated from Hypericum wilsonii. Structurally, 1… Click to show full abstract
Cyclooxygenase-2 (COX-2) is a significant therapeutic target of chronic inflammatory diseases. Soniiglucinols A–D (1–4), four new polycyclic polyprenylated acylphloroglucinols (PPAPs) with diverse architectures, were isolated from Hypericum wilsonii. Structurally, 1 and 2 represent the first examples of PPAPs that are uniquely defined by the presence of a fascinating tricyclo-[7.3.1.03,7]tridecane core bearing an unusual 5/7/6 carbon skeleton. Compounds 3 and 4 were the first PPAPs sharing intriguing tricyclo-[7.3.1.02,7]tridecane and tricyclo-[6.3.1.02,6]dodecane moieties, respectively. More significantly, 1 and 2 were the first reported PPAPs functioning as potent cyclooxygenase-2 (COX-2) inhibitors with efficient anti-inflammatory activities, which provided a basis to design novel COX-2 inhibitors based on the new tricyclo-[7.3.1.03,7]tridecane fragment.
               
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