Comparison of the phytoestrogen trans‐resveratrol (3,4′,5‐trihydroxystilbene) structures from x‐ray diffraction and solution NMR

Abstract

The NMR-derived solution structure of trans-3,4',5-trihydroxystilbene (resveratrol) was compared with two recent literature crystal x-ray structures, resveratrol in complex with human transthyretin (TTR-RES) from 1DVS.pdb and resveratrol bound to chalcone synthase (CHS-RES) from 1CGZ.pdb. 1H and 13C NMR spectra of resveratrol were acquired in DMSO-d6. Assignments were obtained from an analysis of DQF-COSY, TOCSY, DEPT, HMQC/HSQC, HMBC and INADEQUATE NMR spectra. Past 1H and 13C NMR literature assignments are corrected. The dihedral angle 2-1-1'-2' provides an indication of the relative spatial orientation of the two phenolic rings. Values of 1.62, - 54.10 and 12.6 +/- 1.1 degrees were found for the 1DVS.pdb, 1CGZ.pdb and NMR resveratrol structures, respectively. The 1DVS.pdb resveratrol structure is 'flat' with the two phenolic rings along the same plane. The 1CGZ.pdb structure has these two rings almost orthogonal to each other, and the NMR structure has these two rings much closer to being along the same plane. The angles 1-alpha--alpha' and 1'-alpha'--alpha are along the same trace and of similar magnitude for the 1CGZ.pdb and NMR resveratrol structures. For the 1DVS.pdb resveratrol structure, these angles are about 7-10 degrees greater, with alpha and alpha' being 180 degrees out-of-phase from the other two structures. The alpha rings did not overlap, with the NMR result representing a 'median model' of the two x-ray structures.

Facile Synthesis and Cytotoxic Activity of the First Ferrocene-Resveratrol Conjugate

“…The NMR assignments in the present study are in a good agreement with previously published data for RSV [9,10] and its 3-substituted RSV-glycoside [11] (Table 1). …”

“…Table 1. NMR (δ in ppm) spectroscopic data of RSV, [9,10] RSV-glycoside [11] and ferrocene-RSV conjugate III (c = 110 −3 mol dm −3 ) …”

Determination of Phytochemical Compounds, and Tyrosinase Inhibitory and Antimicrobial Activities of Bioactive Compounds from <i>Streblus ilicifolius</i> (S Vidal) Corner

“…The structures of the isolated compounds, identified by physical properties and spectroscopic data, including UV, IR, NMR and MS data and confirmed by comparison with previously reports are as (E)-2,4-dihydroxy-3-(3,7-dimethyl-2,6-octadienyl) benzaldehyde (1) [14], p-hydroxy benzoic acid methyl ester (2) [15], umbelliferone (3) [16], moracin M (4) [17] and trans-resveratrol (5) [18]. Their spectral data are given as follow: 2,4-Dihydroxy-3-(3,7-dimethyl-2 …”

Stacking interaction study of trans‐resveratrol (trans‐3,5,4′‐trihydroxystilbene) in solution by Nuclear Magnetic Resonance and Fourier Transform Infrared Spectroscopy

“…The assignment was checked by two-dimensional COSY and NOESY experiments (data not shown) and was in agreement with previous work. [17,18] To investigate the dynamic conditions of trans-RSV (2 × 10 −2 M), proton non-selective (R These results put in evidence the drastic change that occurred in RSV dynamics, with concentration. It can be noted that at high concentration, the increase of R 1 with increasing temperature indicates the existence of RSV slow dynamics.…”