Flavonoid Glycosides From the Bulbs of Lilium speciosum var. gloriosoides and their Potential Antiviral Activity Against RSV

Chen, Wen; Zhang, Hui; Wang, Jianfen; Hu, Xiaojian

doi:10.1007/s10600-019-02714-7

Cited by 7 publications

(5 citation statements)

References 17 publications

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“…Glycosides are secondary metabolites that widely exist in all organs of plants, such as flowers, fruits, leaves, skins, and roots, etc ( Gruner et al, 2002 ), and previous studies found that glycosides had a wide range of pharmacological activities, such as antiviral ( Chen W. et al, 2019 ; Khodair et al, 2019 ), antibacterial ( Mohammed et al, 2019 ), anticancer ( Gurung et al, 2018 ; Rahim et al, 2020 ), antioxidant ( Jiang et al, 2018 ; Hawas et al, 2019 ), and anti-HIV ( He et al, 2019 ) activities. Meanwhile, studies also found that glycoside derivatives showed exceeding inhibitory activities against plant pathogens.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides

Chen

Zhang

et al. 2021

Front. Chem.

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A series of novel 1,3,4-thiadiazole derivatives of glucosides were synthesized by the starting materials d-glucose and 5-amino-1,3,4-thiadiazole-2-thiol in good yields with employing a convergent synthetic route. The results of bioactivities showed that some of the target compounds exhibited good antifungal activities. Especially, compounds 4i showed higher bioactivities against Phytophthora infestans (P. infestans), with the EC50 values of 3.43, than that of Dimethomorph (5.52 μg/ml). In addition, the target compounds exhibited moderate to poor antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas campestris pv. citri (Xcc).

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Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides

Chen

Zhang

et al. 2021

Front. Chem.

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“…Besides the well-known flavonoid C -glycosides vitexin, isovitexin, orientin, isoorientin, schaftoside, isoshaftoside, neoshaftoside, and their O -glycosylated and or O -acylated derivatives, more and more flavonoid C -glycosides were disclosed. These 6- or 8- C - β -D-glucopyranosides can be divided into five groups: (1) mono- C -glycosylated flavonoids 1 – 3 [ 12 , 37 ], 39 – 42 [ 12 , 13 , 37 ]; (2) 6, 8-di- C -glycosylated flavonoids 4 [ 38 ], 43 [ 39 ]; (3) flavonoid 6- or 8- C - β -D-glucopyranoside-7- O - β -D-glucopyranosides 5 – 10 [ 40 , 41 , 42 , 43 ], 44 [ 44 ]; (4) 2″- or 6″- O -glycosylated flavonoid 6- or 8- C - β -D-glucopyranosides 11 – 31 [ 9 , 38 , 45 , 46 , 47 , 48 , 49 , 50 ], 45 – 55 [ 14 , 51 , 52 , 53 , 54 , 55 , 56 , 57 ]; (5) 2″- or 6″- O -acylated flavonoid 6- or 8- C - β -D-glucopyranosides 32 – 38 [ 10 , 11 , 55 , 56 ], 56 – 80 [ 57 , 58 , 59 , 60 ,…”

Section: Structuresmentioning

confidence: 99%

“…Speciflavoside A ( 32 ), isolated from a 70% methanolic extract of Lilium speciosum var. gloriosoides Baker, showed potent antiviral activity against RSV, with an IC 50 value of 2.9 μg/mL, comparable to that of ribavirin, an approved drug for the treatment of RSV infections in humans [ 10 ].…”

Section: Pharmacological Activitymentioning

confidence: 99%

Recent Advances on Natural Aryl-C-glycoside Scaffolds: Structure, Bioactivities, and Synthesis—A Comprehensive Review

Liu

2022

Molecules

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Aryl-C-glycosides, of both synthetic and natural origin, are of great significance in medicinal chemistry owing to their unique structures and stability towards enzymatic and chemical hydrolysis as compared to O-glycosides. They are well-known antibiotics and potent enzyme inhibitors and possess a wide range of biological activities such as anticancer, antioxidant, antiviral, hypoglycemic effects, and so on. Currently, a number of aryl-C-glycoside drugs are on sale for the treatment of diabetes and related complications. This review summarizes the findings on aryl-C-glycoside scaffolds over the past 20 years, concerning new structures (over 200 molecules), their bioactivities—including anticancer, anti-inflammatory, antioxidant, antivirus, glycation inhibitory activities and other pharmacological effects—as well as their synthesis.

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“…Especially, the scaly bulbs of Lilium species have been used to treat coughs, sore throats, and hemoptysis because of dry lung or lung heat, and insomnia associated with hallucinations, restlessness, and irritability . Previous phytochemical studies investigating Lilium species reported the role of flavonoids, , steroidal saponins, − and phenypropanoids, ,− as major constituents. These compounds exhibit diverse biological activities including antiviral, antitumor, , antidiabetic, anti-inflammatory, and anti-oxidant activities .…”

Section: Introductionmentioning

confidence: 99%

“…Previous phytochemical studies investigating Lilium species reported the role of flavonoids, , steroidal saponins, − and phenypropanoids, ,− as major constituents. These compounds exhibit diverse biological activities including antiviral, antitumor, , antidiabetic, anti-inflammatory, and anti-oxidant activities . Steroidal saponins isolated from the bulbs of Lilium longiflorum showed inhibitory activity against 12- O -tetradecanoylphorbol-13-acetate-stimulated 32 P-incorporation into phospholipids of HeLa cells and promoted scratch wound closure by stimulating fibroblast activation and migration via selective upregulation of TGF-β type I receptors .…”

Section: Introductionmentioning

confidence: 99%

Purification of Phenylpropanoids from the Scaly Bulbs of Lilium Longiflorum by CPC and Determination of Their DPP-IV Inhibitory Potentials

et al. 2020

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The scaly bulbs of Lilium longiflorum (Liliaceae) are used as a food ingredient and a traditional medicine in East Asia. A preliminary study revealed that treatment with 100 μg/mL of the ethyl acetate fraction of this plant material inhibited dipeptidyl peptidase IV (DPP-IV) to 58.99%. Phytochemical studies were conducted to identify the active ingredient, and five compounds, namely, 1 (2.9 mg, 75.8% purity at 320 nm), 2 (12.2 mg, 97.9% purity at 320 nm), 3 (3.1 mg, 66.5% purity at 320 nm), 4 (6.8 mg, 96.9% purity at 320 nm), and 5 (6.2 mg, 90.2% purity at 320 nm) were purified from 200 mg of the ethyl acetate fraction of L. longiflorum via centrifugal partition chromatography (CPC) with a two-phase solvent system composed of chloroform/methanol/isopropanol/water (5:2:2:4, v/v/v/v) in an ascending mode. Their structures were identified as 1-O-p-coumaroyl-2-O-β-glucopyranosylglycerol (regaloside D, 1), 3,6′-O-diferuloylsucrose (2), 1-O-p-coumaroyl-2-O-β-glucopyranosyl-3-O-acetylglycerol (regaloside B, 3), 1-O-p-coumaroylglycerol (4), and 4-O-acetyl-3,6′-O-diferuloylsucrose (5), respectively, by 1H and 13C NMR and MS analysis. Compounds 2 and 5 exhibited DPP-IV inhibitory activities with IC50 values of 46.19 and 63.26 μM, respectively. Compounds 1, 3, and 4 did not show activities, indicating that biphenylpropanoids linked via the sugar moiety are more effective than phenylpropanoids with glycerol or glyceryl glucoside. This is the first report of simultaneous separation of five phenylpropanoids from L. longiflorum by CPC and evaluation of their DPP-IV inhibitory activities.

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Flavonoid Glycosides From the Bulbs of Lilium speciosum var. gloriosoides and their Potential Antiviral Activity Against RSV

Cited by 7 publications

References 17 publications

Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides

Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides

Recent Advances on Natural Aryl-C-glycoside Scaffolds: Structure, Bioactivities, and Synthesis—A Comprehensive Review

Purification of Phenylpropanoids from the Scaly Bulbs of Lilium Longiflorum by CPC and Determination of Their DPP-IV Inhibitory Potentials

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