Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from <i>Perilla frutescens</i>
<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 r...
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MDPI AG
2022-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/18/6102 |
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| author | Jing Zuo Tian-Hao Zhang Liang Xiong Lu Huang Cheng Peng Qin-Mei Zhou Ou Dai |
| author_facet | Jing Zuo Tian-Hao Zhang Liang Xiong Lu Huang Cheng Peng Qin-Mei Zhou Ou Dai |
| author_sort | Jing Zuo |
| collection | DOAJ |
| description | <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>. |
| first_indexed | 2024-03-09T23:00:17Z |
| format | Article |
| id | doaj.art-a842ea98b6ce4cce8c98993b0dd520a5 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T23:00:17Z |
| publishDate | 2022-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a842ea98b6ce4cce8c98993b0dd520a52023-11-23T18:04:18ZengMDPI AGMolecules1420-30492022-09-012718610210.3390/molecules27186102Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from <i>Perilla frutescens</i>Jing Zuo0Tian-Hao Zhang1Liang Xiong2Lu Huang3Cheng Peng4Qin-Mei Zhou5Ou Dai6State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China<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>.https://www.mdpi.com/1420-3049/27/18/6102<i>Perilla frutescens</i>cyclolignansenantiomersanti-inflammatory activityRAW 264.7 macrophages |
| spellingShingle | Jing Zuo Tian-Hao Zhang Liang Xiong Lu Huang Cheng Peng Qin-Mei Zhou Ou Dai Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from <i>Perilla frutescens</i> Molecules <i>Perilla frutescens</i> cyclolignans enantiomers anti-inflammatory activity RAW 264.7 macrophages |
| title | Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from <i>Perilla frutescens</i> |
| title_full | Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from <i>Perilla frutescens</i> |
| title_fullStr | Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from <i>Perilla frutescens</i> |
| title_full_unstemmed | Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from <i>Perilla frutescens</i> |
| title_short | Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from <i>Perilla frutescens</i> |
| title_sort | two pairs of 7 7 cyclolignan enantiomers with anti inflammatory activities from i perilla frutescens i |
| topic | <i>Perilla frutescens</i> cyclolignans enantiomers anti-inflammatory activity RAW 264.7 macrophages |
| url | https://www.mdpi.com/1420-3049/27/18/6102 |
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