Abstract
In the present study, resveratrol and various oligomeric derivatives were obtained from a 14 L bioreactor culture of elicited grapevine cell suspensions (Vitis labrusca L.). The crude ethyl acetate stilbene extract obtained from the culture medium was fractionated by centrifugal partition chromatography (CPC) using a gradient elution method and the major stilbenes contained in the fractions were subsequently identified by using a 13C-NMR-based dereplication procedure and further 2D NMR analyses including HSQC, HMBC, and COSY. Beside δ-viniferin (2), leachianol F (4) and G (4′), four stilbenes (resveratrol (1), ε-viniferin (5), pallidol (3) and a newly characterized dimer (6)) were recovered as pure compounds in sufficient amounts to allow assessment of their biological activity on the cell growth of three different cell lines, including two human skin malignant melanoma cancer cell lines (HT-144 and SKMEL-28) and a healthy human dermal fibroblast HDF line. Among the dimers obtained in this study, the newly characterized resveratrol dimer (6) has never been described in nature and its biological potential was evaluated here for the first time. ε-viniferin as well as dimer (6) showed IC50 values on the three tested cell lines lower than the ones exerted by resveratrol and pallidol. However, activities of the first two compounds were significantly decreased in the presence of fetal bovine serum although that of resveratrol and pallidol was not. The differential tumor activity exerted by resveratrol on healthy and cancer lines was also discussed.
Highlights
Resveratrol and its derivatives are secondary plant metabolites widely represented in nature and described as important defense molecules acting as phytoalexins in a few plants [1,2,3,4,5].Phytostilbenes are implicated with human health benefits and possess many therapeutic actions such as anti-inflammatory [6], antioxidant [7], cardioprotective [8], anti-diabetic [9], anti-aging [10]and anticancer properties [11]
We report here on the production in a 14 L stirred bioreactor of various phytostilbenes from grapevine cell suspensions of Vitis labrusca L. (Concord), their separation by centrifugal partition chromatography (CPC) to study their activity on the cell viability of two human skin malignant melanoma cancer cell lines (HT-144 and SKMEL-28) and a healthy human dermal fibroblast Human dermal fibroblasts (HDF) line
Our results revealed tumor-specificity of resveratrol, that is,This the confirms cell viability a previous work demonstrating that resveratrol employed at similar doses on healthy or cancer cells inhibition exerted by this compound was found to be lower on the healthy human dermal fibroblasts, has no effects on the former [29]
Summary
Resveratrol and its derivatives are secondary plant metabolites widely represented in nature and described as important defense molecules acting as phytoalexins in a few plants [1,2,3,4,5].Phytostilbenes are implicated with human health benefits and possess many therapeutic actions such as anti-inflammatory [6], antioxidant [7], cardioprotective [8], anti-diabetic [9], anti-aging [10]and anticancer properties [11]. The specific chemical structure of resveratrol, which is based on a hydroxylated stilbene skeleton, was reported to be directly involved in this activity. Works have already evidenced the role of the position of hydroxyphenyl groups on the stilbene skeleton on its antioxidant properties [13] as well as the importance of its stereochemistry on cell proliferation [14]. Study of the biological properties of resveratrol derivatives (hydroxylated, methylated, isoprenylated and oligomers) which are based on the same molecular structure, would allow the development of new anticancer agents. Interest in the activity of resveratrol derivatives is not recent [15,16] as previous works have already underlined the anticancer potential of piceatannol [17], a 30 -hydroxyresveratrol and pterostilbene [18], the 3,5-dimethyl-resveratrol
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