55332-75-7Relevant academic research and scientific papers
Pinoresinol-lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties
Davin, Laurence B.,Hwang, Julianne K.,Lewis, Norman G.,Moinuddin, Syed G. A.
, (2020)
Two western red cedar pinoresinol-lariciresinol reductase (PLR) homologues were studied to determine their enantioselective, substrate versatility, and kinetic properties. PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8- and 8′-linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can enantiospecifically metabolize different furofuran lignans with modified aromatic ring substituents, but where phenolic groups at both C4/C4′ are essential for catalysis. These results are consistent with quinone methide intermediate formation in the PLR active site. Site-directed mutagenesis and kinetic measurements provided additional insight into factors affecting enantioselectivity and kinetic properties. From these data, PLRs can be envisaged to allow for the biotechnological potential of generation of various lignan skeleta, that could be differentially “decorated” on their aromatic ring substituents, via the action of upstream dirigent proteins.
Isolation of enantiomeric furolactones and furofurans from Rubus idaeus L. with neuroprotective activities
Zhou, Le,Han, Feng-Ying,Lu, Li-Wei,Yao, Guo-Dong,Zhang, Ying-Ying,Wang, Xiao-Bo,Lin, Bin,Huang, Xiao-Xiao,Song, Shao-Jiang
, p. 122 - 129 (2019/05/29)
A phytochemical study on the fruits of Rubus idaeus L. (Rosaceae) yielded eight pairs of enantiomeric lignans, including one undescribed furolactone named (?)-idaeusinol A and six undescribed furofuran derivatives named (+/?)-idaeusinol B–D. The structures of these isolated compounds were elucidated by spectroscopic analyses and a combination of computational techniques including gauge-independent atomic orbital (GIAO) calculation of 1D NMR data and TD-DFT calculation of electronic circular dichroism (ECD) spectra. Bioactivity screenings suggested that (+)-idaeusinol D exhibited the most significant protective effect against H2O2-induced neurotoxicity at the concentration of 25 μM. In contrast, (?)-idaeusinol D, as the enantiomer of (+)-idaeusinol D, showed no effect against H2O2-induced neurotoxicity at both 25 and 50 μM concentration.
