Kaempferol-7-O-neohesperidoside

Analysis of phenolic compounds by high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry in senescent and water-stressed tobacco.[Pubmed:22118617]

Plant Sci. 2012 Jan;182:71-8.

Evaluation of a significant part of the phenylpropanoid pathway metabolites is facilitated by the fast high-performance liquid chromatography with electrospray ionization tandem mass spectrometry (LC-MS/MS) analytical method. The technology described was applied in tobacco plants (Nicotiana tabacum L. cv. Wisconsin) to identify 20 phenolic compounds and to detect differences in phenylpropanoid profiles in two types of experiments. In the first one, senescent and non-senescent parts of flowering plants were compared, while in the second, watered plants were compared with water-stressed young plants. The 20 identified phenolic compounds were: seven hydroxycinnamoylquinic acids, seven hydroxycinnamic acid glucosides, one salicylic acid glucoside, two conjugated flavonols with disaccharides, and three hydroxycinnamic acid amides (HCAA) of putrescine. In general, the levels of phenylpropanoid compounds increased under water stress or senescent conditions, with the exception of HCAA, which decreased in senescent samples, and 4-O-p-coumaroylquinic acid and trihydroxycinamic acid-O-glucoside, which did not change in both experiments. The main product in all the samples was 5-O-caffeoylquinic acid (neochlorogenic acid). Another compound, Kaempferol-7-O-neohesperidoside, was tentatively identified for the first time in tobacco plants. This method, which can be applied in other plant species, allows a simple and efficient comparative study of metabolite profile variations (qualitative and quantitative) in response to different physiological and/or environmental plant situations.

Study of the collision-induced radical cleavage of flavonoid glycosides using negative electrospray ionization tandem quadrupole mass spectrometry.[Pubmed:12526005]

J Mass Spectrom. 2003 Jan;38(1):43-9.

Negative electrospray ionization tandem quadrupole mass spectrometry was used to study the collision-induced dissociation (CID) of the O-glycosidic bond from different commercially available flavonoid glycosides. Depending on the structure, flavonoid glycosides can undergo both a collision-induced homolytic and heterolytic cleavage of the O-glycosidic bond producing deprotonated radical aglycone ((Y(0) - H)(-*)) and aglycone (Y(0) (-)) product ions. The relative abundance of the radical aglycone to the aglycone fragment from flavonol-3-O-glycosides increased with increasing number of hydroxyl substituents in the B ring and in the order kaempferol - Kaempferol-7-O-neohesperidoside showed only a minor radical aglycone product ion as opposed to kaempferol-3-O-rutinoside. The relative abundance of the radical aglycone to the aglycone fragment from flavone-7-O-glycosides was also dependent on the substitution in the B ring. CID of apigenin-7-O-glucoside produced relatively more of the radical aglycone fragment than luteolin-7-O-glucoside, while only the aglycone fragment was found from diosmetin-7-O-rutinoside. The position of the sugar substitution also affected the fragmentation of the flavone glycosides, such that the product ion spectrum of luteolin-4'-O-glucoside showed only the aglycone fragment as opposed to luteolin-7-O-glucoside. No radical aglycone fragments were found from the flavanone-7-O-glycosides and dihydrochalcone glycoside investigated in the study.