Glechomanamides A–C, Germacrane Sesquiterpenoids with an Unusual Δ8-7,12-Lactam Moiety from Salvia scapiformis and Their Antiangiogenic Activity
| العنوان: | Glechomanamides A–C, Germacrane Sesquiterpenoids with an Unusual Δ8-7,12-Lactam Moiety from Salvia scapiformis and Their Antiangiogenic Activity |
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| المؤلفون: | Sang Kook Lee, Ri Zhen Huang, Yan Kui Zhu, Heng-Shan Wang, Dong Liang, Cai Yi Wang, Dong-Chan Oh, Donghwa Kim |
| المصدر: | Journal of Natural Products. 82:3056-3064 |
| بيانات النشر: | American Chemical Society (ACS), 2019. |
| سنة النشر: | 2019 |
| مصطلحات موضوعية: | Pharmacology, Tube formation, 010405 organic chemistry, Stereochemistry, Angiogenesis, Chemical structure, Organic Chemistry, Pharmaceutical Science, 01 natural sciences, 0104 chemical sciences, Analytical Chemistry, 010404 medicinal & biomolecular chemistry, chemistry.chemical_compound, Complementary and alternative medicine, chemistry, Drug Discovery, Lactam, Molecular Medicine, Moiety, Hemiacetal, Lead compound, Two-dimensional nuclear magnetic resonance spectroscopy |
| الوصف: | Three new germacrane sesquiterpenoid-type alkaloids with an unusual Δ8-7,12-lactam moiety, glechomanamides A-C (1-3), and two pairs of 7,12-hemiketal sesquiterpenoid epimers (4a/b, 5a/b) were isolated from Salvia scapiformis. Their structures were elucidated by spectroscopic methods including HRESIMS, IR, UV, and 1D and 2D NMR and also confirmed by single-crystal X-ray diffraction analysis. The chemical transformation of compounds 1-5 in a solution environment was analyzed by 2D NMR spectroscopy. The aza acetallactams (1-3) were stable in organic solvent, while single crystals of the hemiacetal esters (4a/b, 5a/b) underwent a tautomeric equilibrium after being dissolved. Single crystals of 4a, 4b, and 5a were obtained for the first time as their naturally occurring forms. Glechomanamide B (2) exhibited antiangiogenic activity by suppression of vascular endothelial growth factor (VEGF)-induced tube formation through modulation of VEGF receptor 2 (VEGFR2)-mediated signaling pathways in human umbilical vascular endothelial cells (HUVECs). In addition, compound 2 also showed the significant suppression of mRNA expression associated with glycolysis and angiogenesis biomarkers in high glucose (30 mM)-induced HUVECs. These findings suggest that compound 2 might be a potential lead compound candidate for the management of diabetic retinopathy. |
| تدمد: | 1520-6025 0163-3864 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::d5e3289604f651065353fbba47abf4e4 https://doi.org/10.1021/acs.jnatprod.9b00648 |
| حقوق: | CLOSED |
| رقم الأكسشن: | edsair.doi...........d5e3289604f651065353fbba47abf4e4 |
| قاعدة البيانات: | OpenAIRE |
Find this issue from the American Chemical Society | تدمد: | 15206025 01633864 |
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