Phenylpropanoid Glycerol Glucosides Attenuate Glucose Production in Hepatocytes

Murray, Anne F.; Palatini, Kimberly; Komarnytsky, Slavko; Gianfagna, Thomas J.; Munafo, John P.

doi:10.1021/acsomega.9b00751

Cited by 13 publications

(15 citation statements)

References 20 publications

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“…Studies have shown that regalosides have anti-oxidation, bacteriostasis, anti-inflammatory and other functions. Murray et al [45] proved that phenylpropanoid glycerol glucosides can be used as an inhibitor of hepatic glucose production and may have potential to regulate metabolic syndrome and delay type II diabetes. The total glycosides of lily, including six regalosides, can protect cardiomyocytes by protecting mitochondria [46].…”

Section: Profiling Of Secondary Metabolitesmentioning

confidence: 99%

Comprehensive Analysis of Secondary Metabolites in the Extracts from Different Lily Bulbs and Their Antioxidant Ability

Tang

Liu

et al. 2021

Antioxidants

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The genus Lilium contains more than 100 wild species and numerous hybrid varieties. Some species of them have been used as medicine and food since ancient times. However, the research on the active components and the medical properties of lilies has only focused on a few species. In this study, the total phenolic acid content (TPC), total flavonoid content (TFC), and antioxidant capacity of 22 representative lilies were systematically investigated. The results showed that the TPC, TFC and antioxidant activity were highly variable among different lilies, but they were significantly positively correlated. Hierarchical cluster analysis indicated that L. henryi and L. regale were arranged in one group characterized by the highest TPC, TFC and antioxidant capacity, followed by Oriental hybrids and Trumpet and Oriental hybrids. The traditional edible and medicinal lilies were clustered in low TPC, TFC and antioxidant capacity group. A total of 577 secondary metabolites, including 201 flavonoids, 153 phenolic acids, were identified in the five species with great differences in antioxidant capacity by extensive targeted metabonomics. Differentially accumulated metabolites (DAMs) analysis reviewed that the DAMs were mainly enriched in secondary metabolic pathways such as isoflavonoid, folate, flavonoid, flavone, flavonol, phenylpropanoid, isoquinoline alkaloid biosynthesis, nicotinate and nicotinamide metabolism and so on. Correlation analysis identified that 64 metabolites were significantly positively correlated with antioxidant capacity (r ≥ 0.9 and p < 0.0001). These results suggested that the genus Lilium has great biodiversity in bioactive components. The data obtained greatly expand our knowledge of the bioactive constituents of Lilium spp. Additionally, it also highlights the potential application of Lilium plants as antioxidants, functional ingredients, cosmetic products and nutraceuticals.

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Section: Profiling Of Secondary Metabolitesmentioning

confidence: 99%

Comprehensive Analysis of Secondary Metabolites in the Extracts from Different Lily Bulbs and Their Antioxidant Ability

Tang

Liu

et al. 2021

Antioxidants

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“…Rosmarinic acid esters exhibited a broad spectrum of biological effects (Shen et al, 2018;Liang et al, 2017;Thammason et al, 2018). Glycerol phenylpropanoid glucosides act as hepatic glucose production inhibitors; structure-activity relationships indicated that the hydroxylation pattern of the hydroxycinnamic acid moiety and acetylation accounted for differences in activity (Murray et al, 2019).…”

Section: Discussionmentioning

confidence: 99%

GC-MS and HPLC-ESI-MS-MS Characterization of Sanchezia oblonga (Acanthaceae) Extracts

Ravasi¹,

Negri²,

Salatino³

et al. 2020

JFR

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The genus Sanchezia (Acanthaceae) comprises neotropical herbs and shrubs with showy flowers. Sanchezia oblonga (syn. S. nobilis) is a shrub of the rainforests of central and south America. The ethanolic extracts of leaves and stems from S. oblonga were analyzed by GC-EI-MS and RPHPLC-DAD-ESI-MS/MS. Fatty acids (free and esterified) and phytosterols were detected by the former method. Benzyl alcohol glycosides (21 and 25), sinapic acid glycoside esters (29 and 31), ethyl rosmarinate (24), sinapic acid-O-glucoside (28), dihydrosinapic acid-O-glucoside (26), catechin-O-arabinoside (36), in addition to flavonols glycosides (23, 32, 33 and 35) and rosmarinic acid-3’-O-glucoside (34) were detected by RPHPLC-DAD-ESI-MS/MS. Three new compounds, detected only in leaves, were tentatively identified as phenylpropane glyceride derivatives 1-O-coumaroyl-2-hydroxy propanal (20) and 1-O-coumaroyl-2-O-glycosyl propanal (22, 30). Compounds 20, 22 and 30 from S. oblonga are similar with phenylpropane glycerides present in red sorghum (Sorghum bicolor L. (Moench) and Lilium longiflorum Thunb. It is noteworthy that S. oblonga could be used in cooking as a complement after more detailed studies. Sorghum grain foods exhibit potential health benefits against chronic diseases related to over-nutrition. Lilium longiflorum possess flower buds and bulbs that are used for both culinary and medicinal purposes in many parts of the world. Studies on chemical composition and biological activity of the genus Sanchezia are scarce. The presence of phytosterols and flavonol glycosides were recently reported in leaves from this species. However, the chemical profile of the extracts analyzed in this work differs from that previously reported for aerial parts of S. nobilis (sin. S. oblonga). Further studies, including statistical methods, such as principal component analysis and hierarchical cluster analysis will be needed to evaluate chemical markers for this species.

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“…For example, Baihe Wuyao decoction (BWD), a prescription of Traditional Chinese Medicines, composed of Lilii Bulbus and Linderae Radix, has been used to treat epigastric pain and superficial gastritis for hundreds of years in China [3] . Previous phytochemical investigations indicated that Lilium contains several steroidal saponins, phenylpropanoid glycosides as well as phenyl glycosides [4–8] …”

Section: Introductionmentioning

confidence: 99%

“…[3] Previous phytochemical investigations indicated that Lilium contains several steroidal saponins, phenylpropanoid glycosides as well as phenyl glycosides. [4][5][6][7][8] To search for new bioactive constitutes of Lilium. Lilium regale Wilson was selected and three new chlorophenyl glycosides (1)(2)(3) were obtained from its bulb subsequently (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Three Previously Undescribed Chlorophenyl Glycosides from the Bulbs of Lilium regale

Yan

Guo

Zhou

et al. 2021

Chemistry & Biodiversity

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Three previously undescribed chlorophenyl glycosides, (2,4,6‐trichloro‐3‐hydroxy‐5‐methoxyphenyl)methyl β‐D‐glucopyranoside (1), (2,4‐dichloro‐3,5‐dimethoxyphenyl)methyl 6‐O‐β‐D‐glucopyranosyl‐β‐D‐glucopyranoside (2) and 4‐chloro‐3‐methoxy‐5‐methylphenyl 6‐O‐(6‐deoxy‐β‐L‐mannopyranosyl)‐β‐D‐glucopyranoside (3) were obtained from Lilium regale. The absolute configurations of these new finds were elucidated by comprehensive analyses of spectroscopic data combined with acid hydrolysis derivatization. (2,4‐dichloro‐3,5‐dimethoxyphenyl)methyl 6‐O‐β‐D‐glucopyranosyl‐β‐D‐glucopyranoside (2) can inhibit the proliferation of lung carcinoma A549 cells with an IC50 value of 29 μΜ.

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Phenylpropanoid Glycerol Glucosides Attenuate Glucose Production in Hepatocytes

Cited by 13 publications

References 20 publications

Comprehensive Analysis of Secondary Metabolites in the Extracts from Different Lily Bulbs and Their Antioxidant Ability

Comprehensive Analysis of Secondary Metabolites in the Extracts from Different Lily Bulbs and Their Antioxidant Ability

GC-MS and HPLC-ESI-MS-MS Characterization of Sanchezia oblonga (Acanthaceae) Extracts

Three Previously Undescribed Chlorophenyl Glycosides from the Bulbs of Lilium regale

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