دورية أكاديمية
Isolation and biomimetic synthesis of phenylpropionyl phenylethylamines from Chloranthus henryi.
| العنوان: | Isolation and biomimetic synthesis of phenylpropionyl phenylethylamines from Chloranthus henryi. |
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| المؤلفون: | Wang N; Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 211198, China., Zhang D; Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 211198, China., Wang X; Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 211198, China., Wen J; Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 211198, China., Li Q; Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 211198, China., Zan Z; Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 211198, China., Zhao S; Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 211198, China., Kong L; Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 211198, China. Electronic address: cpu_lykong@126.com., Luo J; Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 211198, China. Electronic address: luojun@cpu.edu.cn. |
| المصدر: | Phytochemistry [Phytochemistry] 2024 Jun; Vol. 222, pp. 114090. Date of Electronic Publication: 2024 Apr 09. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: Elsevier Country of Publication: England NLM ID: 0151434 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-3700 (Electronic) Linking ISSN: 00319422 NLM ISO Abbreviation: Phytochemistry Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: 2003- : London : Elsevier Original Publication: 1961-2003: Oxford : Pergamon Press. |
| مواضيع طبية MeSH: | Phenethylamines*/chemistry , Phenethylamines*/isolation & purification , Phenethylamines*/pharmacology , Phenethylamines*/chemical synthesis , Nitric Oxide*/biosynthesis , Nitric Oxide*/antagonists & inhibitors, Mice ; Animals ; RAW 264.7 Cells ; Molecular Structure ; Amaryllidaceae/chemistry ; Biomimetics ; Dose-Response Relationship, Drug ; Structure-Activity Relationship |
| مستخلص: | In this study, ten phenylpropionyl phenylethylamines, including five previously undescribed ones (1a/b, 2a/b, and 3), five known analogues (4-8), and two established phenylpropanoids precursors (9, 10) were isolated from the aerial parts of Chloranthus henryi Hemsl. Their structures, including absolute configurations, were determined by high-resolution mass spectrometry, enantio-separation, electronic circular dichroism calculation, and single crystal diffraction. Compounds 1a and 1b were the first examples of natural hetero-[2 + 2] cycloaddition products between phenylpropionyl phenylethylamine and phenylpropene. The plausible hetero-[2 + 2] biosynthesis pathway was confirmed by a photocatalytic biomimetic synthesis in eight steps, which also led to the production of three other potential natural homo-[2 + 2] adducts (1'a/b, 2', and 3'). Bioactivity screening indicated that these adducts bear medium inhibitory activity on nitric oxide generation, with IC Competing Interests: Declaration of competing interest No compete in financial interests. (Copyright © 2024 Elsevier Ltd. All rights reserved.) |
| فهرسة مساهمة: | Keywords: Biomimetic synthesis; Chloranthaceae; Chloranthus henryi hemsl; Phenylpropionyl phenylethylamines; [2 + 2] cycloaddition |
| المشرفين على المادة: | 0 (Phenethylamines) 31C4KY9ESH (Nitric Oxide) |
| تواريخ الأحداث: | Date Created: 20240410 Date Completed: 20240508 Latest Revision: 20240508 |
| رمز التحديث: | 20240509 |
| DOI: | 10.1016/j.phytochem.2024.114090 |
| PMID: | 38599509 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1873-3700 |
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| DOI: | 10.1016/j.phytochem.2024.114090 |