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

ABSTRACT: 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 ?-site amyloid precursor protein cleaving enzyme 1 (BACE1) with IC50 values of 81.17, 51.13 and 48.89?µM, respectively.

SUBMITTER: Zhu QF

PROVIDER: S-EPMC5541560 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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

Zhu Qin-Feng QF Bao Ying Y Zhang Zhi-Jun ZJ Su Jia J Shao Li-Dong LD Zhao Qin-Shi QS

Royal Society open science 20170719 7

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 ...[more]

PMID: 28791165

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Project description:A new series of azomethine-functionalized compounds was synthesized from the condensation of 2-hydroxy-1,3-propanediamine and 2-thienylcarboxaldehydes in the presence of a drying agent. The derivatives were spectroscopically characterized by NMR, LC-MS, UV/Vis, IR and elemental analysis. Variable temperature 1 H-NMR (-60 to +60 °C) was performed to investigate the effect of solvent polarity; the capability of solvent to form H-bond was found to dramatically influencing the tautomerization process of the desired structures. The calculated thermochemical parameters (ΔH298 , ΔG298 and ΔS298 ) at DFT and MP2 levels of theory explained that 3 b exists in equilibrium with two tautomers. The basis of the electronic absorptions was pursued through Time-Dependent Density-Functional Theory (TD-DFT). Analysis of the structural surfaces was inspected and the molecular electrostatic potential (MEP) demonstrated that the three functionalized compounds were relatively analogous in the electronic distributions. Furthermore, the electrophilic and nucleophilic centers lying on the molecular surfaces were probably playing a key-role in stabilizing the compounds through the nonclassical C-H⋅⋅⋅π interactions and hydrogen bonding. The impact of solvent polarity on absorption spectra were investigated via solvatochromic shifts. For instance, compound 3 c displayed a gradual shift of the maximum absorption to the red area when the solvent polarity was increased, recording a 21 nm of bathochromic shift. In contrast, no significant solvent-effect on 3 a and 3 b was observed. The solvation relation was pursued between Gutmann's donicity numbers the experimental λmax ; exhibited almost positive linear performance with a minor oscillation, that ascribe to the possible weak interface between the molecules of solute and designated solvents. The bandgap energy of all products were assessed experimentally using optical absorption spectra following Tauc approach, giving -4.050 (3 a), -3.900 (3 b) and -3.210 (3 c) eV. However, the ΔE were computationally figured out from TD-DFT simulation to be -4.258 (3 a), -4.022 (3 b) and -3.390 (3 c) eV.

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

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A biomimetic semisynthesis enables structural elucidation of selaginellin U: a tautomeric cyclic alkynylphenol from <i>Selaginella tamariscina</i>.

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