ent-Kaurane-Based Diterpenoids, Dimers, and Meroditerpenoids from Isodon xerophilus
| Autor: | Xiao-Nian Li, Kun Hu, Han-Dong Sun, Bing-Chao Yan, Pema-Tenzin Puno, Jia-Meng Dai, Xing-Ren Li |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Pharmacology
Quantum chemical 2019-20 coronavirus outbreak Coronavirus disease 2019 (COVID-19) 010405 organic chemistry Chemistry Stereochemistry Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) Chemical shift Organic Chemistry Pharmaceutical Science 01 natural sciences 0104 chemical sciences Analytical Chemistry 010404 medicinal & biomolecular chemistry Complementary and alternative medicine Drug Discovery Molecular Medicine No production Isodon xerophilus Ent kaurane |
| Zdroj: | Journal of Natural Products. 83:3717-3725 |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | Eight new diterpenoids (1-8) with varied structures were isolated from the aerial parts of Isodon xerophilus. Among them, xerophilsin A (1) was found to be an unusual meroditerpenoid representing a hybrid of an ent-kauranoid and a long-chain aliphatic ester, xerophilsins B-D (2-4) are dimeric ent-kauranoids, while xerophilsins E-H (5-8) are new ent-kauranoids. The structures of 1-8 were elucidated mainly through the analyses of their spectroscopic data. The absolute configurations of 2, 6, and 8 were confirmed by single-crystal X-ray diffraction, and the configuration of C-16 in 7 was established through quantum chemical calculation of NMR chemical shifts, as well as modeling of key interproton distances. Bioactivity evaluation of all isolated compounds revealed that 2, 3, and 5 inhibited NO production in LPS-stimulated RAW264.7 cells. |
| Databáze: | OpenAIRE |
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