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New bakuchiol dimers from Psoraleae Fructus and their inhibitory activities on nitric oxide production

BACKGROUND: Dried fruits of Psoralea corylifolia L. (Psoraleae Fructus) is one of the most popular traditional Chinese medicine with treatment for nephritis, spermatorrhea, pollakiuria, asthma, and various inflammatory diseases. Bakuchiol is main meroterpenoid with bioactive diversity from Psoraleae...

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Autores principales: Xu, Qingxia, lv, Qian, Liu, Lu, Zhang, Yingtao, Yang, Xiuwei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: BioMed Central 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8499495/
https://www.ncbi.nlm.nih.gov/pubmed/34620201
http://dx.doi.org/10.1186/s13020-021-00499-y
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author Xu, Qingxia
lv, Qian
Liu, Lu
Zhang, Yingtao
Yang, Xiuwei
author_facet Xu, Qingxia
lv, Qian
Liu, Lu
Zhang, Yingtao
Yang, Xiuwei
author_sort Xu, Qingxia
collection PubMed
description BACKGROUND: Dried fruits of Psoralea corylifolia L. (Psoraleae Fructus) is one of the most popular traditional Chinese medicine with treatment for nephritis, spermatorrhea, pollakiuria, asthma, and various inflammatory diseases. Bakuchiol is main meroterpenoid with bioactive diversity from Psoraleae Fructus. This study was designed to seek structural diverse bakuchiol derivants with anti-inflammatory activities from this plant. METHODS: Various column chromatography methods were used for isolation experiment. Structures and configurations of these compounds were determined by spectroscopic methods and single-crystal X-ray diffraction. Their inhibition on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages were evaluated by the Griess reaction. RESULTS: Twelve unpresented bakuchiol dimmers, bisbakuchiols M–U (1–9) and bisbakuchiol ethers A–C (10–12), along with five known compounds (13–17), were isolated from the fruits of Psoralea corylifolia L. Compounds 1–3, 10–12, 16 and 17 exhibited inhibitory activities against LPS-induced NO production in RAW264.7 macrophages, and the inhibition of compound 1 (half maximal inhibitory concentration (IC(50)) value = 11.47 ± 1.57 μM) was equal to that of L-N(6)-(1-iminoethyl)-lysine (IC(50) = 10.29 ± 1.10 μM) as a positive control. CONCLUSIONS: Some compounds exhibited inhibitory activities against NO production, and the study of structure–activity relationship suggested that uncyclized compounds with oxygen substitution at C-12/12′ showed strong inhibitory activities, and carbonyl units contributed to enhanced activities. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13020-021-00499-y.
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spelling pubmed-84994952021-10-08 New bakuchiol dimers from Psoraleae Fructus and their inhibitory activities on nitric oxide production Xu, Qingxia lv, Qian Liu, Lu Zhang, Yingtao Yang, Xiuwei Chin Med Research BACKGROUND: Dried fruits of Psoralea corylifolia L. (Psoraleae Fructus) is one of the most popular traditional Chinese medicine with treatment for nephritis, spermatorrhea, pollakiuria, asthma, and various inflammatory diseases. Bakuchiol is main meroterpenoid with bioactive diversity from Psoraleae Fructus. This study was designed to seek structural diverse bakuchiol derivants with anti-inflammatory activities from this plant. METHODS: Various column chromatography methods were used for isolation experiment. Structures and configurations of these compounds were determined by spectroscopic methods and single-crystal X-ray diffraction. Their inhibition on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages were evaluated by the Griess reaction. RESULTS: Twelve unpresented bakuchiol dimmers, bisbakuchiols M–U (1–9) and bisbakuchiol ethers A–C (10–12), along with five known compounds (13–17), were isolated from the fruits of Psoralea corylifolia L. Compounds 1–3, 10–12, 16 and 17 exhibited inhibitory activities against LPS-induced NO production in RAW264.7 macrophages, and the inhibition of compound 1 (half maximal inhibitory concentration (IC(50)) value = 11.47 ± 1.57 μM) was equal to that of L-N(6)-(1-iminoethyl)-lysine (IC(50) = 10.29 ± 1.10 μM) as a positive control. CONCLUSIONS: Some compounds exhibited inhibitory activities against NO production, and the study of structure–activity relationship suggested that uncyclized compounds with oxygen substitution at C-12/12′ showed strong inhibitory activities, and carbonyl units contributed to enhanced activities. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13020-021-00499-y. BioMed Central 2021-10-07 /pmc/articles/PMC8499495/ /pubmed/34620201 http://dx.doi.org/10.1186/s13020-021-00499-y Text en © The Author(s) 2021 https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/ (https://creativecommons.org/publicdomain/zero/1.0/) ) applies to the data made available in this article, unless otherwise stated in a credit line to the data.
spellingShingle Research
Xu, Qingxia
lv, Qian
Liu, Lu
Zhang, Yingtao
Yang, Xiuwei
New bakuchiol dimers from Psoraleae Fructus and their inhibitory activities on nitric oxide production
title New bakuchiol dimers from Psoraleae Fructus and their inhibitory activities on nitric oxide production
title_full New bakuchiol dimers from Psoraleae Fructus and their inhibitory activities on nitric oxide production
title_fullStr New bakuchiol dimers from Psoraleae Fructus and their inhibitory activities on nitric oxide production
title_full_unstemmed New bakuchiol dimers from Psoraleae Fructus and their inhibitory activities on nitric oxide production
title_short New bakuchiol dimers from Psoraleae Fructus and their inhibitory activities on nitric oxide production
title_sort new bakuchiol dimers from psoraleae fructus and their inhibitory activities on nitric oxide production
topic Research
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8499495/
https://www.ncbi.nlm.nih.gov/pubmed/34620201
http://dx.doi.org/10.1186/s13020-021-00499-y
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