New Depsides and Neuroactive Phenolic Glucosides from the Flower Buds of Rugosa Rose (Rosa rugosa)

Abstract

The flower buds of Rosa rugosa Thunb. have been commonly used as a source of rose oil and as an ingredient in tea in eastern Asia, including China, Japan, and Korea. Repeated chromatography of a hot water extract from the flower buds of R. rugosa led to the isolation and characterization of three new depside glucosides, rosarugosides A−C (1−3), along with three phenolic compounds, one ionone glucoside, four flavonoids, and two tannins having known chemical structures. Linarionoside A and 2-phenylethyl-(6-O-galloyl)-β-D-glucopyranoside were isolated from R. rugosa for the first time in this study. The structures of the new compounds 1−3 were elucidated by interpreting one-and two-dimensional nuclear magnetic resonance spectroscopic and mass spectrometric data. Among the isolates, a new depside glucoside (1) and two major phenolic glucosides (4 and 5) improved MK-801-induced sensorimotor gating deficits, which were measured via an acoustic startle response test in mice.

Molecular Networking and Bioassay-Guided Preparation and Separation of Active Extract and Constituents from Vicia tenuifolia Roth

“…On the other hand, the MS 2 ion products showed peaks at m/z 147.2835 and 162.8927 (Figure S1, Supplementary Materials), revealing the presence of rhamnosyl and glucosyl moieties [23]. In addition, the chemical shift values of glycosidic signals were obtained from their spectroscopic data and compared to those of identical signals from reported values [24,25], respectively. The 1 H NMR spectrum of 1 revealed the presence of 2,4,6 trihydroxy-aromatic units at δ H 6.50 (1H, d, J = 2.3 Hz, H-3), 6.21 (1H, d, J = 2.3 Hz, H-5), 3,4-dihydroxy-5-methoxybenzoyl [δ H 7.16 (1H, d, J = 1.9 Hz, H-2 ), 7.11 (1H, d, J = 1.9 Hz, H-6 ), 3.78 (3H, 5-OCH 3 )] units, two anomeric protons at δ H 5.65 (1H, d, J = 1.8 Hz, H-1 ) and δ H 4.66 (1H, d, J = 7.3 Hz, H-1 ), which are suggested to respectively correspond to α-and β-glycosidic units, along with a geminal coupling constant in methylene group at δ H 3.45 (1H, d, J = 17.0 Hz, H 2 -7) and 3.62 (1H, d, J = 17.0 Hz, H 2 -7), and a secondary methyl at δ H 0.96 (3H, d, J = 6.2 Hz, H 3 -6 ) together with other carbonic signals (Table 1).…”

“…The 13 C NMR spectrum of 1 revealed 27 signals, including two carboxylic at δ C 169.3 (C-8) and 163.8 (C-7'), as well as 12 aromatic and two glycosidic groups that were classified by Dept and HMQC spectra. The spectroscopic data (Figures S1-S8, Supplementary Materials), for 1 consisted of those reported compounds [25] with some differences from the functional group of the second phenyl (B) ring and sugar unit attachment. Briefly, the HMBC spectrum showed the correlations of H-2 (δ H 7.11) to C-4 (δ C 140.3)/C-6 (δ C 111.1)/C-7 (δ C 163.8) and those of H-6 (δ H 7.16) to C-2 (δ C 105.2)/C-4 (δ C 140.3)/C-7 (δ C 163.8), establishing the B-ring partial structure.…”

Rosa platyacantha Schrenk from Kazakhstan—Natural Source of Bioactive Compounds with Cosmetic Significance

“…Galactolipids, which are also found in rose hips, have shown some anti-inflammatory and antitumor activities [ 25 ]. Flower buds of R. rugosa were shown recently to contain acidic polysaccharides with antioxidant and anti-aging properties [ 26 ] as well as neuroactive depside glucosides, flavonoids, and tannins [ 27 ]. Flavonoids, including kaempferol and quercetin derivatives, were also found in R. damascena flower buds [ 28 ].…”

Polysaccharides and polyphenol in dried Morinda citrifolia fruit tea after different processing conditions: Optimization analysis using response surface methodology

“…It is made by young leaves and/or young stems of Camellia sinensis plant in a narrow sense ( Kröppl et al, 2012 ; Taylor, Hamilton-Miller & Stapleton, 2005 ), and by leaves, flowers and fruit from any plant in a broad sense ( Pekal, Biesaga & Pyrzynska, 2013 ). Chrysanthemum morifolium flowers ( Guzelmeric, Vovk & Yesilada, 2015 ), flowers or flower buds of Lonicerae Japonicae Flos ( Cai et al, 2020 ), the flower buds of Rosa ( Chang et al., 2019 ) and the leaf of Lycium barbarum L. ( Zhao et al, 2020 ) have been widely used as tea. Now there is a various unique tea in different places such as Teng Cha (China), Apple tea (Turkey), Chamomile tea (Russia and Germany), Mate tea (Argentina), Rooibos tea (South Africa) ( Jin et al, 2016 ; Raal et al, 2012 ).…”