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Abstract
In this study, the chemical diversity of polyphenols in Iris lactea var. chinensis seeds was identified by combined MS/MS-NMR analysis. Based on the annotated chemical profile, the isolation of stilbene oligomers was conducted, and consequently, stilbene oligomers (1-10) were characterized. Of these, compounds 1 and 2 are previously undescribed stilbene dimer glycoside (1) and tetramer glycoside (2), respectively. Besides, to evaluate this plant seed as a rich source of stilbene oligomers, we quantified three stilbene oligomers of I. lactea var. chinensis seeds. The contents of three major stilbene oligomers—trans-ε-viniferin (3), vitisin A (6), and vitisin B (9)—in I. lactea var. chinensis seeds were quantified as 2.32 (3), 4.95 (6), and 1.64 (9) mg/g dry weight (DW). All the isolated compounds were tested for their inhibitory activities against influenza neuraminidase. Compound 10 was found to be active with the half maximal inhibitory concentration (IC50) values at 4.76 μM. Taken together, it is concluded that I. lactea var. chinensis seed is a valuable source of stilbene oligomers with a human health benefit.
Highlights
Stilbene is a class of natural polyphenols that can construct complex oligomeric structures [1].Plant-derived stilbenes are recognized as secondary metabolites to protect host plants in the presence of exogenous stimuli or attacks, such as physical injury, UV irradiation, or pathogenic invasion [2,3,4].The structural variety of stilbene oligomers is derived from either C–C or C–O–C bonds with two, four, six, or eight linkage points on monomeric stilbene units [5], and the stilbene oligomer formation is known to be mediated by oxidative couplings
To analyze chemical diversity of I. lactea var. chinensis-derived secondary metabolites, the MS/MS molecular network analysis was carried with I. lactea var. chinensis extract together with transwhich is a typical from natural products
The stilbene contents of I. lactea var. chinensis seeds suggested that this natural product could be considered as a great source of stilbene oligomers with over 8 mg of stilbene oligomers per 1 g of the seeds
Summary
Stilbene is a class of natural polyphenols that can construct complex oligomeric structures [1]. The structural variety of stilbene oligomers is derived from either C–C or C–O–C bonds with two, four, six, or eight linkage points on monomeric stilbene units [5], and the stilbene oligomer formation is known to be mediated by oxidative couplings. These stilbene oligomers have been reported to possess many bioactivities, including anti-inflammatory, anti-microbial, antioxidant, antitumor, hepatoprotective, and metabolic disorder modulatory activities [5,6]. The stilbene oligomers are present in very small amounts in plants, and the distribution of the stilbene oligomers in the plant kingdom is not wide but seems to be limited to specific plant families like Iridaceae, Moraceae, Orchidaceae, Polygonaceae, and Vitaceae [5]
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