New Flavonolignan Glycosides from the Aerial Parts of  Zizania latifolia

Lee, Seung-Su; Baek, Nam‐In; Baek, Yoon-Su; Chung, Dae‐Kyun; Song, Myoung‐Chong; Bang, Myun‐Ho

doi:10.3390/molecules20045616

Cited by 28 publications

(12 citation statements)

References 11 publications

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“…As demonstrated in our previous study, tricin and its derivatives, including a new flavonolignan salcolin D, were isolated as the active components exerting the anti-inflammatory and anti-allergic activities in ethanol extracts from the aerial parts of Z. latifolia . Lee et al [ 17 ] reported the presence of new flavonolignan groups along with tricin in this plant. In our previous study, the quantitative analysis of 11 compounds present in the ethanol extract from the aerial parts of Z. latifolia (including tricin and its derivatives) confirmed that tricin is the quantitatively major component in the extract (unpublished data).…”

Section: Resultsmentioning

confidence: 99%

Protection against UVB-Induced Wrinkle Formation in SKH-1 Hairless Mice: Efficacy of Tricin Isolated from Enzyme-Treated Zizania latifolia Extract

Moon¹,

Park

Jhee

et al. 2018

Molecules

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Tricin, a flavone found mainly in rice bran and sugarcane, has various beneficial effects. It has proven to be a clinically safe and selective potent inhibitor of different cancer cell lines. In this study, we evaluated the efficacy of enzyme-treated Zizania latifolia (ETZL) and its major active compound tricin on skin photoaging in SKH-1 hairless mice. Tricin (0.3 mg/kg) and ETZL (50, 150, and 300 mg/kg) were orally administrated to mice for 14 weeks; no cytotoxicity was observed during the entire experimental period. After UVB exposure, we observed significant increases in keratinization, coarse wrinkles, loss of moisture, thickened epidermis, and collagen fiber degradation in the dorsal skin. These features of photoaging were significantly suppressed after oral administration of tricin or ETZL. In addition, the protein expression of collagen effectively increased in ETZL (150 and 300 mg/kg)-treated mice, while the increased metalloproteinase (MMP)-1 and MMP-3 expressions were reduced after exposure to tricin or ETZL, although the effects were not dose-dependent. These data indicate that ETZL may be effective for attenuation of UVB-induced skin damage and photoaging in hairless mice, possibly by inhibiting MMPs expression.

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Section: Resultsmentioning

confidence: 99%

Protection against UVB-Induced Wrinkle Formation in SKH-1 Hairless Mice: Efficacy of Tricin Isolated from Enzyme-Treated Zizania latifolia Extract

Moon¹,

Park

Jhee

et al. 2018

Molecules

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“…It has long been studied as an extractable portion of various grasses and cereals (family Poaceae), such as wheat, bamboo, oat, maize and rice (Markley and Bailey, ; Vogel et al ., ; Harborne and Hall, ). The extractable tricin can occur in either free form (Nakano et al ., ) or in various conjugated forms, such as tricin‐glycosides (Duarte‐Almeida et al ., ; Van Hoyweghen et al ., ; Bottcher et al ., ), tricin‐lignans (Bouaziz et al ., ; Wenzig et al ., ) and (tricin‐glycoside)‐lignans (Bottcher et al ., ; Lee et al ., ), as shown in Figure . As we recently reported, not all of the tricin‐lignans may be such (Lan et al ., ); as the ones we extracted for metabolite profiling displayed no optical activity and were obviously the result of a remarkable variety of combinatorial coupling products from not just the monolignols but the monolignol acetate and p ‐coumarate conjugates, we contended that these are incipient tricin‐lignins or tricin‐(oligo)lignols or, more generally, flavonolignins or flavonolignols (Lan et al ., ).…”

Section: Introductionmentioning

confidence: 82%

“…(d) Tricin‐(acyl‐glucoside) (Duarte‐Almeida et al ., ). (e) (Tricin‐glucoside)‐lignan (Lee et al ., ).…”

Section: Introductionunclassified

Tricin‐lignins: occurrence and quantitation of tricin in relation to phylogeny

et al. 2016

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SUMMARYTricin [5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one], a flavone, was recently established as an authentic monomer in grass lignification that likely functions as a nucleation site. It is linked onto lignin as an aryl alkyl ether by radical coupling with monolignols or their acylated analogs. However, the level of tricin that incorporates into lignin remains unclear. Herein, three lignin characterization methods: acidolysis; thioacidolysis; and derivatization followed by reductive cleavage; were applied to quantitatively assess the amount of lignin-integrated tricin. Their efficiencies at cleaving the tricin-(4 0 -O-b)-ether bonds and the degradation of tricin under the corresponding reaction conditions were evaluated. A hexadeuterated tricin analog was synthesized as an internal standard for accurate quantitation purposes. Thioacidolysis proved to be the most efficient method, liberating more than 91% of the tricin with little degradation. A survey of different seed-plant species for the occurrence and content of tricin showed that it is widely distributed in the lignin from species in the family Poaceae (order Poales). Tricin occurs at low levels in some commelinid monocotyledon families outside the Poaceae, such as the Arecaceae (the palms, order Arecales) and Bromeliaceae (Poales), and the non-commelinid monocotyledon family Orchidaceae (Orchidales). One eudicotyledon was found to have tricin (Medicago sativa, Fabaceae). The content of lignin-integrated tricin is much higher than the extractable tricin level in all cases. Lignins, including waste lignin streams from biomass processing, could therefore provide a large and alternative source of this valuable flavone, reducing the costs, and encouraging studies into its application beyond its current roles.

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“…Two guaiacylglyceryl tricin isomers of molecular ion peak [M-H]at m/z 525 that were defined as salcolin A and salcolin B 28 . in addition to their glycosides that displayed molecular ion peak [M-H]at m/z 687, and tentatively identified as tricin 4′-O-(erythro-βguaiacylglyceryl ether) glucoside and its threo isomer 29…”

Section: Phytochemical Profiling Of L Chinensis Leaf Extractmentioning

confidence: 99%

Structural Characterization of Polyphenolics in Livistona chinensis Using HPLC-PDA-MS

Ahmed

El-Khrisy

El‐Kashak

et al. 2019

Journal of Advanced Pharmacy Research

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Objectives: This study focused on the identification and characterization of secondary metabolites tentatively from aqueous ethanolic leaf extract of Livistona chinensis by HPLC-PDA-ESI-MS/MS and evaluation of its cytotoxic activity. Methods: The aqueous ethanolic extract was analyzed by high performance liquid chromatography (HPLC) coupled to photodiode array detection of mass spectroscopy (PDA-MS/MS), to detect the secondary metabolites in L. chinensis leaves extract. It was also estimated for its cytotoxicity against human prostate carcinoma (PC3) and hepatocellular liver carcinoma (HepG2) cancer cell lines using SRB (3-(4, 5-dimethyl thiazol-2-yl)-2, 5-diphenyltetrazolium bromide) assay. Results: Fortytwo secondary metabolites were tentatively identified; the most major compounds were C-glycoside derivatives of apigenin, luteolin and tricin together with phenolic acids. The 70% alcoholic extract of L. chinensis leaves exhibit more antitumor activity against PC3 than against HepG2. Conclusion: L. chinensis is a privileged source of C-flavonoids that revealed the efficiency of HPLC-MS metabolomics in natural products drug discovery.

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New Flavonolignan Glycosides from the Aerial Parts of Zizania latifolia

Cited by 28 publications

References 11 publications

Protection against UVB-Induced Wrinkle Formation in SKH-1 Hairless Mice: Efficacy of Tricin Isolated from Enzyme-Treated Zizania latifolia Extract

Protection against UVB-Induced Wrinkle Formation in SKH-1 Hairless Mice: Efficacy of Tricin Isolated from Enzyme-Treated Zizania latifolia Extract

Tricin‐lignins: occurrence and quantitation of tricin in relation to phylogeny

Structural Characterization of Polyphenolics in Livistona chinensis Using HPLC-PDA-MS

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