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A biomimetic semisynthesis enables structural elucidation of selaginellin U: a tautomeric cyclic alkynylphenol from Selaginella tamariscina

Two new lactone-containing selaginellins T and U (1 and 2) together with eleven known selaginellin derivatives (3 and 7–16) were isolated from the whole plant of Selaginella tamariscina. The structure of tautomeric selaginellin U along with its biogenetic pathway was confirmed and proposed by a cros...

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Detalles Bibliográficos
Autores principales: Zhu, Qin-Feng, Bao, Ying, Zhang, Zhi-Jun, Su, Jia, Shao, Li-Dong, Zhao, Qin-Shi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society Publishing 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5541560/
https://www.ncbi.nlm.nih.gov/pubmed/28791165
http://dx.doi.org/10.1098/rsos.170352
Descripción
Sumario:Two new lactone-containing selaginellins T and U (1 and 2) together with eleven known selaginellin derivatives (3 and 7–16) were isolated from the whole plant of Selaginella tamariscina. The structure of tautomeric selaginellin U along with its biogenetic pathway was confirmed and proposed by a cross-validation of the semisynthesis of compound 4 from selaginellin (3) and derivation from 2 to 4. Additionally, compounds 3, 13 and 16 exhibited good inhibitory activities against β-site amyloid precursor protein cleaving enzyme 1 (BACE1) with IC(50) values of 81.17, 51.13 and 48.89 µM, respectively.