Antiproliferative and antioxidant activities of a tricin acylated glycoside from sugarcane (Saccharum officinarum) juice

Duarte-Almeida, Joaquim Maurício; Negri, Giuseppina; Salatino, Antônio; Carvalho, João Ernesto de; Lajolo, Franco Maria

doi:10.1016/j.phytochem.2007.01.015

Cited by 104 publications

(71 citation statements)

References 27 publications

(33 reference statements)

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“…Flavonoids have been shown to modify eicosanoid biosynthesis (antiprostanoid and anti-inflammatory responses), protect low density lipoprotein (LDL) from oxidation (prevention of atherosclerotic plaque formation), and promote relaxation of cardiovascular smooth muscle (antihypertensive, antiarrhythmic effects). In addition, flavonoids have been shown to have antiviral and anticarcinogenic properties [49].…”

Section: Resultsmentioning

confidence: 99%

Flavonoids and phenolic acids from pearl millet (Pennisetum glaucum) based foods and their functional implications

Nambiar

Sareen

Daniel³

et al. 2012

FFHD

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Background: Pearl millet (Pennisetum glaucum), considered a poor man's cereal, may be a repository of dietary antioxidants, especially flavonoids and phenolic acids, which provide bioactive mechanisms to reduce free radical induced oxidative stress and probably play a role in the prevention of ageing and various diseases associated with oxidative stress, such as cancer, cardiovascular, and neurodegenerative diseases.

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Section: Resultsmentioning

confidence: 99%

Flavonoids and phenolic acids from pearl millet (Pennisetum glaucum) based foods and their functional implications

Nambiar

Sareen

Daniel³

et al. 2012

FFHD

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“…The 49-O site on tricin can also be glucosylated to form a flavonoid glucoside (with possible further acylation of the Glc by p-coumarate); such a compound was isolated from Acacia nilotica (Khanam et al, 2011). C-O-and C-C-linked glycosides of tricin at the 5-O-, 7-O-, and 6-Cpositions have also been reported (Bouaziz et al, 2002;Duarte-Almeida et al, 2007;Van Hoyweghen et al, 2010;Nakano et al, 2011). These compounds and others have also recently been detected in sugarcane (Bottcher et al, 2013).…”

Section: Radical Coupling Reactions Between Tricin and Monolignolsmentioning

confidence: 89%

“…Tricin and its derivatives can be solvent extracted from monocot samples such as wheat (Triticum aestivum), oat bran (Avena sativa), bamboo (Leleba oldhami), sugarcane (Saccharum officinarum), and maize (Zea mays). Extracted compounds can take the form of tricin itself, 7-O-glycosylated tricin, or the flavonolignan in which tricin is 49-O-etherified by putative coupling with coniferyl alcohol (Ju et al, 1998;Bouaziz et al, 2002;Wenzig et al, 2005;Duarte-Almeida et al, 2007;Van Hoyweghen et al, 2010;Nakano et al, 2011;Bottcher et al, 2013;Moheb et al, 2013).…”

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confidence: 99%

Tricin, a Flavonoid Monomer in Monocot Lignification

et al. 2015

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Tricin was recently discovered in lignin preparations from wheat (Triticum aestivum) straw and subsequently in all monocot samples examined. To provide proof that tricin is involved in lignification and establish the mechanism by which it incorporates into the lignin polymer, the 49-Ob-coupling products of tricin with the monolignols (p-coumaryl, coniferyl, and sinapyl alcohols) were synthesized along with the trimer that would result from its 49-O-b-coupling with sinapyl alcohol and then coniferyl alcohol. Tricin was also found to cross couple with monolignols to form tricin-(49-O-b)-linked dimers in biomimetic oxidations using peroxidase/hydrogen peroxide or silver (I) oxide. Nuclear magnetic resonance characterization of gel permeation chromatography-fractionated acetylated maize (Zea mays) lignin revealed that the tricin moieties are found in even the highest molecular weight fractions, ether linked to lignin units, demonstrating that tricin is indeed incorporated into the lignin polymer. These findings suggest that tricin is fully compatible with lignification reactions, is an authentic lignin monomer, and, because it can only start a lignin chain, functions as a nucleation site for lignification in monocots. This initiation role helps resolve a long-standing dilemma that monocot lignin chains do not appear to be initiated by monolignol homodehydrodimerization as they are in dicots that have similar syringyl-guaiacyl compositions. The term flavonolignin is recommended for the racemic oligomers and polymers of monolignols that start from tricin (or incorporate other flavonoids) in the cell wall, in analogy with the existing term flavonolignan that is used for the lowmolecular mass compounds composed of flavonoid and lignan moieties.Lignin, a complex phenylpropanoid polymer in the plant cell wall, is predominantly deposited in the cell walls of secondary-thickened cells (Vanholme et al., 2010). It is synthesized via oxidative radical coupling reactions from three prototypical monolignols, p-coumaryl, coniferyl, and sinapyl alcohols, differentiated by their degree of methoxylation ortho to the phenolic hydroxyl group. Considered within the context of the entire polymer, the main structural features of lignin can be defined in terms of its p-hydroxyphenyl (H), guaiacyl (G), and syringyl (S) units, derived respectively from these three monolignols (Ralph, 2010). Several novel monomers, all deriving from the monolignol biosynthetic pathway, have been found to incorporate into lignin in wild-type and transgenic plants. For example, monolignol acetate, p-hydroxybenzoate, and p-coumarate ester conjugates have all been shown to incorporate into lignin polymers and are the source of naturally acylated lignins (Ralph et al., 2004;Lu and Ralph, 2008); lignins derived solely from caffeyl alcohol were found in the seed coats of both monocot and dicot plants (Chen et al., 2012a(Chen et al., , 2012b; lignins derived solely from 5-hydroxyconiferyl alcohol were found in a cactus (for example, in a member of the genera Astrop...

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“…Several tricin derivatives have already been described in Saccharum species. 5,11,12,20 The hyphenated HPLC-UV-MS technique proved to be a very important tool for the on-line recording of structural information about minor compounds in a complex matrix such as that of sugarcane juice. Therefore, the on-line structural elucidation of components can offer valuable contributions to the scope of the analytical chemistry (scientific studies or technological applications such as quality assessment) of extracts of plant foods such as sugarcane and its derivatives.…”

Section: Discussionmentioning

confidence: 99%

On-line identification of minor flavones from sugarcane juice by LC/UV/MS and post-column derivatization

Colombo¹,

Yariwake²,

Queiroz³

et al. 2009

J. Braz. Chem. Soc.

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Este trabalho apresenta a identificação "on line" de flavonas minoritárias do suco da cana-deaçúcar (Saccharum officinarum), por cromatografia líquida de alta eficiência com detector UV acoplada à espectrometria de massas (CL/UV/EM) com ionização química à pressão atmosférica, dissociação induzida por colisão (IQPA-DIC-EM/EM) e derivatização pós-coluna utilizando reagentes de deslocamento de UV. As análises CLAE-UV com reagentes de deslocamento forneceram informações sobre a posição da substituição no esqueleto dos flavonóides e, em combinação com dados de EM, estas técnicas permitiram a identificação "on-line" de cinco flavonas da garapa: luteolina-8-C-glucosil-7-O-glucuronídeo; tricina-7-O-neoesperosideo-4'-O-ramnosídeo; tricina-7-O-metilglucuronato-4'-O-ramnosídeo; tricina-7-O-metilglucuronídeo; swertisina; e outras quatro substâncias foram parcialmente identificadas como flavonas glicosiladas. Somente a swertisina (7-O-metilapigenina-6-C-glicosídeo) foi anteriormente descrita no bagaço da cana-de-açúcar.This work describes the on-line characterization of minor flavones from sugarcane (Saccharum officinarum) juice by high-performance liquid chromatography coupled to diode array UV detection and mass spectrometry (LC/UV/MS) using atmospheric pressure chemical ionizationcollision-induced dissociation (APCI-CID-MS/MS) and post-column derivatization using UV shift reagents. HPLC-UV analysis with shift reagents provided information about the substitution pattern in the flavonoid skeleton and, combined with MS data, these techniques allowed for the on-line identification of five "garapa" flavones: luteolin-8-C-glucosyl-7-O-glucuronide; tricin-7-O-neohesperoside-4'-O-rhamnoside; tricin-7-O-methylglucuronate-4'-O-rhamnoside; tricin-7-O-methylglucuronide; swertisin, while four other compounds were partially identified as glycosylflavones. Only swertisin (7-O-methylapigenin-6-C-glucoside) was reported previously in sugarcane molasses.Keywords: sugarcane juice, Saccharum officinarum L. (Poaceae), flavones, LC/UV/MS, UV shift reagents IntroductionHyphenated techniques such as liquid chromatography with UV photodiode array detection (HPLC-UV) and on-line liquid chromatography-ultraviolet detection-mass spectrometry (HPLC-UV-MS) are powerful techniques for the structural identification of compounds found in extracts prepared from very small amounts of plant material. In the case of plant polyphenolic compounds such as flavonoids and xanthones, the possibility of obtaining on-line UV data by a combination with the post-column addition of UV shift reagents is a very important step to validate the structure assignments proposed for the position of oxygenated groups on the polyphenolic skeleton.1 Recently, HPLC-UV-MS and post-column UV-derivatization were employed in the study of Trifolium extracts containing clovamides, flavonoids and isoflavonoids and their UV data were discussed in detail.2 Hyphenated techniques may be the technique of choice in studies requiring analyses of several plant samples, as in metabolomic studies....

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Antiproliferative and antioxidant activities of a tricin acylated glycoside from sugarcane (Saccharum officinarum) juice

Cited by 104 publications

References 27 publications

Flavonoids and phenolic acids from pearl millet (Pennisetum glaucum) based foods and their functional implications

Flavonoids and phenolic acids from pearl millet (Pennisetum glaucum) based foods and their functional implications

Tricin, a Flavonoid Monomer in Monocot Lignification

On-line identification of minor flavones from sugarcane juice by LC/UV/MS and post-column derivatization

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