A biomimetic semisynthesis enables structural elucidation of selaginellin U: a tautomeric cyclic alkynylphenol from Selaginella tamariscina
نویسندگان
چکیده
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 IC50 values of 81.17, 51.13 and 48.89 µM, respectively.
منابع مشابه
Bioactive selaginellins from Selaginella tamariscina (Beauv.) Spring
A new selaginellin named selaginellin O (1), along with three other known selaginellins (2-4) were isolated from Selaginella tamariscina (Beauv.) Spring. On the basis of spectroscopic analysis, the structure of selaginellin O was demonstrated to be 4-[(4'-hydroxy-4-formyl-3-((4-hydroxyphenyl)ethynyl)biphenyl-2-yl)(4-hydroxyphenyl)methylene]cyclohexa-2,5-dien-1-one. Compound 1, 2 and 3 exhibited...
متن کاملIsolation and cytotoxic activity of selaginellin derivatives and biflavonoids from Selaginella tamariscina.
Five selaginellin derivatives, including two new selaginellins termed selaginellins M (1) and N (2), and three previously identified compounds, selaginellin (3), selaginellin A (4), and selaginellin C (5), were isolated from the Selaginella tamariscina (Beauv.) Spring plant. In addition, four known biflavonoids, namely neocryptomerin ( 6), hinokiflavone (7), pulvinatabiflavone (8), and 7''- O-m...
متن کاملSoluble Epoxide Hydrolase Inhibitory Activity of Selaginellin Derivatives from Selaginella tamariscina.
Selaginellin derivatives 1-3 isolated from Selaginella tamariscina were evaluated for their inhibition of soluble epoxide hydrolase (sEH) to demonstrate their potential for the treatment of cardiovascular disease. All selaginellin derivatives (1-3) inhibited sEH enzymatic activity and PHOME hydrolysis, in a dose-dependent manner, with IC50 values of 3.1 ± 0.1, 8.2 ± 2.2, and 4.2 ± 0.2 μM, respe...
متن کاملInhibitory Effect of Selaginellins from Selaginella tamariscina (Beauv.) Spring against Cytochrome P450 and Uridine 5'-Diphosphoglucuronosyltransferase Isoforms on Human Liver Microsomes.
Selaginella tamariscina (Beauv.) has been used for traditional herbal medicine for treatment of cancer, hepatitis, and diabetes in the Orient. Numerous bioactive compounds including alkaloids, flavonoids, lignans, and selaginellins have been identified in this medicinal plant. Among them, selaginellins having a quinone methide unit and an alkylphenol moiety have been known to possess anticancer...
متن کاملSelaginellin A and B, two novel natural pigments isolated from Selaginella tamariscina.
Two new unusual natural pigments were first isolated from the whole herbs of Selaginella tamariscina. The structure of selaginellin A (1) was established as (R,S)-4-[(4'-hydroxy-3-((4-hydroxyphenyl)ethynyl)biphenyl-2-yl)(4-hydroxyphenyl)methylene]-2,5-cyclohexadien-1-one and selaginellin B (2) as (R,S)-4-[(4'-methoxy-4-(methyl)-3-((4-methoxyphenyl)ethynyl)biphenyl-2-yl)(4-methoxyphenyl)methylen...
متن کامل