Secoiridoid Glycoside from the Flowers of Osmanthus fragrans var. aurantiacus Makino Inhibited the Activity of β-Secretase

Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of Fraxinus chinensis

“…Analysis of the 1 H (Table 1 and Figure S3) and 13 ; δ C 62.9 (C-6 ), 71.7 (C-4 ), 74.9 (C-2 ), 78.1 (C-3 ), 78.6 (C-5 ), 101.0 (C-1 )]. These data were nearly identical with those of (8E)-ligstroside (5) [7], except that a methoxy group [δ H 3.76 (3H, s); δ C 55.9] at C-4 of 1 replaced the 4 -hydroxy group of (8E)-ligstroside (5) [7]. This was supported by NOESY correlations between OMe-4 (δ H 3.76) and H-3 /H-5 (δ H 6.85) and by HMBC correlation between OMe-4 (δ H 3.76) and C-4 (δ C 160.0) ( Figure 2).…”

“…Analysis of the 1 H ( Table 1 and Figure S3 ) and 13 C NMR ( Table 2 and Figure S4 ) data of 1 revealed signals for a 4-methoxyphenethoxy group [δ H 2.85 (2H, t, J = 7.0 Hz, H-β), 3.76 (3H, s, OMe-4′′), 4.12, 4.24 (each 1H, each dt, J = 10.5, 7.0 Hz, H-α), 6.85 (2H, d, J = 9.0 Hz, H-3′′ and H-5′′), 7.15 (2H, d, J = 9.0 Hz, H-2′′ and H-6′′); δ C 35.2 (C-β), 55.9 (OMe-4′′), 67.0 (C-α), 115.1 (C-3′′ and C-5′′), 131.2 (C-2′′ and C-6′′), 131.5 (C-1′′), 160.0 (C-4′′)], a secoiridoid moiety [δ H 1.62 (3H, dd, J = 7.0, 1.0 Hz, H-10), 2.44 (1H, dd, J = 14.0, 9.5 Hz, H-6), 2.69 (1H, dd, J = 14.0, 5.0 Hz, H-6), 3.71 (3H, s, OMe-11), 3.95 (1H, dd, J = 9.5, 5.0 Hz, H-5), 5.92 (1H, br s, H-1), 6.06 (1H, br q, J = 7.0 Hz, H-8), 7.51 (1H, s, H-3); δ C 13.7 (C-10), 32.0 (C-5), 41.3 (C-6), 52.1 ( C H 3 OCO-4), 95.3 (C-1), 109.5 (C-4), 125.1 (C-8), 130.5 (C-9), 155.3 (C-3), 168.9 (CH 3 O C O-4), 173.4 (C-7)], and a β-glucose moiety [δ H 3.28–3.36 (3H, m, H-2′, H-4′, and H-5′), 3.42 (1H, dd, J = 8.5, 8.5 Hz, H-3′), 3.66 (1H, dd, J = 12.0, 5.5 Hz, H-6′), 3.88 (1H, dd, J = 12.0, 1.5 Hz, H-6′), 4.80 (1H, d, J = 7.5 Hz, H-1′); δ C 62.9 (C-6′), 71.7 (C-4′), 74.9 (C-2′), 78.1 (C-3′), 78.6 (C-5′), 101.0 (C-1′)]. These data were nearly identical with those of (8 E )-ligstroside ( 5 ) [ 7 ], except that a methoxy group [δ H 3.76 (3H, s); δ C 55.9] at C-4′′ of 1 replaced the 4′′-hydroxy group of (8 E )-ligstroside ( 5 ) [ 7 ]. This was supported by NOESY correlations between OMe-4′′ (δ H 3.76) and H-3′′/H-5′′ (δ H 6.85) and by HMBC correlation between OMe-4′′ (δ H 3.76) and C-4′′ (δ C 160.0) ( Figure 2 ).…”

“…The known isolates were readily identified by a comparison of their physical and spectroscopic data (UV, IR, 1 H NMR, [α] D , and MS) with those of authentic samples or literature values. They include a pyran derivative, fraxilatone (4) [8], four secoiridoids, (8E)-ligstroside (5) [7,9], oleuropein (6) [9], (8E)-3 ,4 -di-O-methyloleuropein (7) [10], and oleoside methyl ester (8) [11], seven coumarins, aesculetin (9) [12], scopoletin (10) [12,13], isoscopoletin (11) [12,14], aesculetin dimethyl ester (12) [12,15], fraxidin (13) [16,17], fraxetin (14) [18], and umbelliferone (15) [19], five phenylpropanoids, methyl isoferulate (16) [20], methyl ferulate (17) [21], methyl 3,4-dimethoxycinnamate (18) [22], methyl (E)-p-coumarate (19) [23], and (E)-ferulaldehyde (20) [24], two phenylethanoids, tyrosol (21) [25] and 4-hydroxyphenethyl acetate (22) [26], a benzenoid, p-hydroxybenzaldehyde (23) [27], two lignans, (+)-pinoresinol (24) [28] and (+)-salicifoliol (25) [29], and a α-tocopheranoid: α-tocopheryl quinone (26) [30].…”

Phenylethanoid Glycoside Profiles and Antioxidant Activities of Osmanthus fragrans Lour. Flowers by UPLC/PDA/MS and Simulated Digestion Model

“…More than 20 kinds of phytochemicals were identified in O. fragrans Lour. flowers, including acteoside, ligustroside, salidroside, rutin, (+)-phillygenin, phillyrin, (−)-phillygenin, taxiresinol, (−)-olivil, and so on. − However, information is lacking on the major antioxidant compounds of O. fragrans Lour. flowers.…”

Effects of Different Drying Methods on the Contents of Nine Components and Immunomodulatory Activities of Four Components in Osmamthus fragrans Flowers

“…13 A secoiridoid glycoside (8 E -ligstroside) and a coumaric acid analog with a monoterpene moiety (floraosmanol A) inhibit the activity of beta-secretase and nitric oxide (NO) production in lipopolysaccharide-activated RAW264.7 macrophages, respectively. 14,15 Lee and collaborators obtained seven lignans from O. fragrans flowers, of which phillygenin has a great effect on protecting liver and preventing NO production. 16,17 In addition, nine polyphenols with antioxidant properties and 8 monosaccharides were isolated and identified in ethanol extracts of O. fragrans flowers.…”