LI Wei-Xian, XU Wen-Jun, LUO Jun, YANG Lei, KONG Ling-Yi. Type B polycyclic polyprenylated acylphloroglucinols from the roots of Hypericum beanii [J]. Chin J Nat Med, 2021, 19(5): 385-390. DOI: 10.1016/S1875-5364(21)60037-7
Citation: LI Wei-Xian, XU Wen-Jun, LUO Jun, YANG Lei, KONG Ling-Yi. Type B polycyclic polyprenylated acylphloroglucinols from the roots of Hypericum beanii [J]. Chin J Nat Med, 2021, 19(5): 385-390. DOI: 10.1016/S1875-5364(21)60037-7
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Type B polycyclic polyprenylated acylphloroglucinols from the roots of Hypericum beanii

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  • Two new type B polycyclic polyprenylated acylphloroglucinols (PPAPs) ( 1 and 2 ) and a known biogenetic precursor hyperbeanol Q ( 3 ) were isolated from the root extract of Hypericum beanii, a medicinal plant widespread in southwest China. Their chemical structures were elucidated by 1D/2D NMR and HRESIMS data analysis, and absolute configurations were determined through detailed electric circular dichroism (ECD) analysis including ECD exciton chirality, Mo2(OAc)4-induced ECD, and ECD comparison. Of these compounds, hyperbeone A ( 1 ) is a typical 3.3.1-type B PPAP with an unusual C-1 geranyl side chain, and hyperberin C ( 2 ) possesses a rare bicyclo5.3.1hendecane core. Taking compound 3 as a starting point, a plausible biosynthetic pathway to the bicyclic type B frameworks of 1 and 2 was proposed.
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