In Silico-Assisted Isolation of trans-Resveratrol and trans-ε-Viniferin from Grapevine Canes and Their Sustainable Extraction Using Natural Deep Eutectic Solvents (NADES)

Abstract

Grapevine canes are an important source of bioactive compounds, such as stilbenoids. This study aimed to evaluate an in silico method, based on the Conductor-like Screening Model for Real Solvents (COSMO-RS) to isolate stilbenoids from a grapevine cane extract by offline heart-cut high-performance countercurrent chromatography (HPCCC). For the following extraction of resveratrol and ε-viniferin from grapevine canes, natural deep eutectic solvents (NADES) were used as an environmentally friendly alternative to the traditionally used organic solvents. In order to evaluate a variety of combinations of hydrogen bond acceptors (HBAs) and hydrogen bond donors (HBDs) for the targeted extraction of stilbenoids, COSMO-RS was applied. In particular, ultrasonic-assisted extraction using a solvent mixture of choline chloride/1,2-propanediol leads to higher extraction yields of resveratrol and ε-viniferin. COSMO-RS calculations for NADES extraction combined with HPCCC biphasic solvent system calculations are a powerful combination for the sustainable extraction, recovery, and isolation of natural products. This in silico-supported workflow enables the reduction of preliminary experimental tests required for the extraction and isolation of natural compounds.

Sustainable In Silico-Supported Ultrasonic-Assisted Extraction of Oligomeric Stilbenoids from Grapevine Roots Using Natural Deep Eutectic Solvents (NADES) and Stability Study of Potential Ready-to-Use Extracts

“…Amberlite ® XAD-16N, choline chloride (>98%), and 1,2-propanediol (99%) were purchased from Sigma-Aldrich (Deisenhofen, Germany). Trans-resveratrol standard (>98%) was obtained from Carl Roth (Karlsruhe, Germany), and trans-ε-viniferin (>94%, λ 280 nm, in-house method, [35]) was isolated from the commercial product Vineatrol ® 30 (Breko GmbH, Bremen, Germany). Stilbenoid tetramers r-2-viniferin (95%, λ 280 nm) and r-viniferin (91%, λ 280 nm) were isolated from de-colored Vitisin ® Powder (Actichem, Montauban, France) using an in-house method [46].…”

“…A previous study evaluated the suitability of HBA and HBD combinations as potential NADES extractants for trans-resveratrol and ε-viniferin [35]. A software-based calculation applying the Conductor-like Screening Model for Real Solvents (COSMO-RS) was used to calculate the activity coefficient (γ) of trans-resveratrol and ε-viniferin in different NADES systems.…”

“…The extraction procedure was performed according to Kiene and co-workers with slight modifications [35]. Approximately 200 mg of the lyophilized and ground grapevine roots were placed in centrifuge tubes (20 mL), mixed with 2 g of NADES or organic extraction solvents, and mixed with a vortex mixer.…”

“…Resveratrol containing NADES extracts with potential use in cosmetic formulations was already described using materials from Polygonum cuspidatum or Gnetum gnemon [10,11]. The successful extraction of resveratrol and ε-viniferin from grapevine canes of different Vitis species [35,44,45] demonstrates the potential of the NADES as an extractant for stilbenoids, although there is still a scientific gap in the NADES extraction of tetrameric stilbenoids. Furthermore, the storage stability of the NADES extracts containing oligomeric stilbenoids, which could be used as ready-to-use extracts in cosmetic formulations, has not been studied.…”

“…In a screening, the calculated activity coefficient was used to show the solubility trend of the stilbenoids in the NADES mixtures, where a lower activity coefficient indicates a better solubility of the stilbenoids in the respective NADES systems. In previous studies, the COSMO-RS approach had been used to select suitable NADES to extract polyphenols from various plant materials [33][34][35].…”