| Summary: | <i>Perilla frutescens</i> (L.) Britt. (Labiatae), a medicinal plant, has been widely used for the therapy of multiple diseases since about 1800 years ago. It has been demonstrated that the extracts of <i>P. frutescens</i> exert significant anti-inflammatory effects. In this research, two pairs of 7,7′-cyclolignan enantiomers, possessing a cyclobutane moiety, (+)/(−)-perfrancin [(+)/(−)-<b>1</b>] and (+)/(−)-magnosalin [(+)/(−)-<b>2</b>], were separated from <i>P. frutescens</i> leaves. The present study achieved the chiral separation and determined the absolute configuration of (±)-<b>1</b> and (±)-<b>2</b>. Compounds (+)-<b>1</b> and (−)-<b>1</b> have notable anti-inflammatory effects by reducing the secretion of pro-inflammatory factors (NO, TNF-α and IL-6) and the expression of pro-inflammatory mediators (iNOS and COX-2). These findings indicate that cyclolignans are effective substances of <i>P. frutescens</i> with anti-inflammatory activity. The present study partially elucidates the mechanisms underlying the effects of <i>P. frutescens</i>.
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