Identification and mass spectrometric characterization of glycosylated flavonoids in Triticum durum plants by high‐performance liquid chromatography with tandem mass spectrometry

Abstract

A mass spectrometric method for extensive detection and semi-quantitative determination of flavonoid glycosides in stem and leaves of young Triticum durum plants is presented. About 100 g of sample were lyophilized and ground, and the compounds of interest were then extracted, cleaned-up, and fractionated using high-performance liquid chromatography (HPLC). Tandem mass spectrometry analyses were performed using a quadrupole-linear ion trap instrument with an information-dependent data acquisition (IDA) protocol that looped two experiments, enhanced MS scan and enhanced product ion scan. Various glycoconjugates, which are all derivatives of only four flavones, apigenin, luteolin, chrysoeriol and tricin, were identified and belong to the following categories: 7 monoglycosides, 31 diglycosides, 15 triglycosides and 1 tetraglycoside. Among these some acylated glycosides were found. Tricin derivatives are present exclusively as O-glycosides, while apigenin and luteolin are present always as C-glycosides. Semi-quantitative estimation was performed by using the monoglycoside and diglycoside of quercetin as internal standards.

CYP93G2 Is a Flavanone 2-Hydroxylase Required for C-Glycosylflavone Biosynthesis in Rice

“…5C). In rice and wheat seedlings, tricin derivatives have been detected almost exclusively as O-glycosides (Cavaliere et al, 2005;Brazier-Hicks et al, 2009). Thus, our data strongly indicated that a completely different enzyme system is involved in flavone O-glycoside biosynthesis.…”

“…We have previously shown that tricin and isovitexin derivatives are the major flavonoids in vegetative tissues of rice (Shih et al, 2008). Both tricin and isovitexin are frequently O-glycosylated (Cavaliere et al, 2005), and the aglycones can be released by acid treatment. In the acid-hydrolyzed methanolic extracts of CYP93G2 mutant leaves, the levels of tricin detected were comparable to those of wild-type samples (Fig.…”

“…In maize, maysin is an O-glycosylated C-glycosylluteolin well known to confer natural resistance in silk tissues toward different lepidopteran larval pests (McMullen et al, 2004). In contrast to the above flavones, tricin (3#,5#-dimethoxylated flavone) is usually detected as O-glycosides in cereals (Cavaliere et al, 2005;Brazier-Hicks et al, 2009). Tricin and its O-glycosides have been shown to function as allelopathic compounds in rice, interfering with weeds and harmful microorganisms in paddy soil (Kong et al, 2004(Kong et al, , 2007.…”

Iron Chelating Activity of Gossypitrin Isolated from the Petals of Talipariti elatum Sw. (Fryxell) Malvaceae

“…Finally, we suggest that the ion at m/z 1278 arise by addition of a glucose residue of m/z 150 from the ion at m/z 1128 (complex E), fragment that comes from the neutral reaction between D (m/z 1072) and another iron ion (+56 Da) (Cavaliere et al, 2005;Satterfield & Brodbelt, 2001). …”

The Occurrence, Fate and Biological Activities ofC-glycosyl Flavonoids in the Human Diet

“…Various plants produce a wide variety of C-glycosyl flavonoids in the leaves, however the parts of such plants traditionally present in the human diet appear to contain a narrower range. In durum wheat (Triticum durum) for example, 29 C-glycosyl derivatives of apigenin, luteolin and chrysoeriol, including some di-C-glycosides, have been identified in the leaves (Cavaliere et al, 2005). In contrast, wheat grain is known to contain only 5 such compounds, 4 of which are derivatives of the flavone luteolin.…”