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Article

Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from Perilla frutescens

by
Jing Zuo
1,2,3,†,
Tian-Hao Zhang
1,2,3,†,
Liang Xiong
1,2,3,
Lu Huang
1,2,3,
Cheng Peng
1,2,
Qin-Mei Zhou
1,2,3,4,* and
Ou Dai
1,2,3,*
1
State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China
2
School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China
3
Institute of Innovative Medicine Ingredients of Southwest Specialty Medicinal Materials, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China
4
Innovative Institute of Chinese Medicine and Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China
*
Authors to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Molecules 2022, 27(18), 6102; https://doi.org/10.3390/molecules27186102
Submission received: 29 August 2022 / Revised: 9 September 2022 / Accepted: 14 September 2022 / Published: 18 September 2022
(This article belongs to the Section Natural Products Chemistry)
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Abstract

Perilla frutescens (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 P. frutescens exert significant anti-inflammatory effects. In this research, two pairs of 7,7′-cyclolignan enantiomers, possessing a cyclobutane moiety, (+)/(−)-perfrancin [(+)/(−)-1] and (+)/(−)-magnosalin [(+)/(−)-2], were separated from P. frutescens leaves. The present study achieved the chiral separation and determined the absolute configuration of (±)-1 and (±)-2. Compounds (+)-1 and (−)-1 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 P. frutescens with anti-inflammatory activity. The present study partially elucidates the mechanisms underlying the effects of P. frutescens.
Keywords: Perilla frutescens; cyclolignans; enantiomers; anti-inflammatory activity; RAW 264.7 macrophages Perilla frutescens; cyclolignans; enantiomers; anti-inflammatory activity; RAW 264.7 macrophages

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MDPI and ACS Style

Zuo, J.; Zhang, T.-H.; Xiong, L.; Huang, L.; Peng, C.; Zhou, Q.-M.; Dai, O. Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from Perilla frutescens. Molecules 2022, 27, 6102. https://doi.org/10.3390/molecules27186102

AMA Style

Zuo J, Zhang T-H, Xiong L, Huang L, Peng C, Zhou Q-M, Dai O. Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from Perilla frutescens. Molecules. 2022; 27(18):6102. https://doi.org/10.3390/molecules27186102

Chicago/Turabian Style

Zuo, Jing, Tian-Hao Zhang, Liang Xiong, Lu Huang, Cheng Peng, Qin-Mei Zhou, and Ou Dai. 2022. "Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from Perilla frutescens" Molecules 27, no. 18: 6102. https://doi.org/10.3390/molecules27186102

APA Style

Zuo, J., Zhang, T.-H., Xiong, L., Huang, L., Peng, C., Zhou, Q.-M., & Dai, O. (2022). Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from Perilla frutescens. Molecules, 27(18), 6102. https://doi.org/10.3390/molecules27186102

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