Total Syntheses of (−)-Spirooliganones A and B and Their Diastereoisomers: Absolute Stereochemistry and Inhibitory Activity against Coxsackie Virus B3

To investigate the effects of configuration on bioactivity, spirooliganones A and B and their six diastereoisomers (<b>1</b>–<b>8</b>) were synthesized in 11 steps. The key benzopyran core was assembled by intermolecular [4 + 2] hetero-Diels–Alder cycloaddition between (−)-sabinene and <i>o</i>-quinone methide, which was generated from the corresponding <i>o</i>-hydroxybenzyl alcohol. After establishing the absolute configuration, the inhibitory activities of spirooliganones <b>1</b>–<b>8</b> against Coxsackie virus B3 were evaluated, and the primary structure–activity relationships were analyzed. Compound <b>3</b> was the most potent compound, with an IC₅₀ of 0.41 μM

Polyketides with New Delhi Metallo-β-lactamase 1 Inhibitory Activity from <i>Penicillium</i> sp.

Three new polyketide compounds (<b>1–3</b>), a new quinolone alkaloid (<b>4</b>), and seven known polyketide derivatives were identified from the cultures of <i>Penicillium</i> sp. I09F 484, a strain isolated from the rhizosphere soil of the plant <i>Picea asperata</i> from Kanas Lake, Xinjiang, China. Their structures were elucidated by extensive spectroscopic data analysis. The absolute configurations of <b>1</b> and <b>4</b> were established by quantum chemical time-dependent density functional theory electronic circular dichroism calculation and Marfey’s method, respectively. Compounds <b>1</b> and <b>2</b> displayed inhibitory activity against New Delhi metallo-β-lactamase 1 with IC₅₀ values of 94.9 and 87.9 μM, respectively