Glycosides rutin

The flavonol glycoside rutin (Figure 4.42) from buckwheat (Fagopyrum esculentum Polygo-naceae) and rue (Ruta graveolens Rutaceae), and the flavanone glycoside hesperidin from Citrus... 

Flavonoids, widely distributed in the plant kingdom, are present in many medicinal plants. The widespread flavonol glycosides rutin 79 and narcissin 65 have been isolated from Mercurialis annua L., a poisonous herb endemic in southern Italy and used in veterinary medicine, as are the minor flavonol glycosides 80,67 and 66. The latter is a new natural compound with a glucopyranosyl unit... 

Fig. (11). Chemical structure of flavonoids isolated from Slachys spruney (family Lamiaceae) quercetin (a) and its glycoside rutin (c), isoscutellarein (b) and its glycoside...

The flavonols and their glycosides contribute to specific taste characteristics such as bitterness and astringency in berry fruits and their products (Shahidi and Naczk, 1995). The molecular structure of flavonols lacks the conjugated double bonds of the anthocyanins, and they are thereby colorless. They may, however, contribute to discoloration of berry fruits, as they are readily oxidized by O-phenoloxidase in the presence of catechin and chlorogenic acid. Discoloration may also occur as a consequence of complex formation with metallic ions. On the other hand, the flavonol glycoside rutin is known to form complexes with anthocyanins, thus stabilizing the color of these compounds. 

The methanolic extracts (la) and (2a) show, in addition to the alkaloids, tlic flavonoi glycoside rutin and the chlorogenic acid (T2), more highly concentrated in la. 

Rutae herba can be characterized by its coumarins (e.g. rutamarin), the furano-coumarins (e.g. bergapten, psoralen) as well as the furanoquinoline alkaloids (e.g, kokusagine, Y-fagarine) and the flavonol glycoside rutin. 

Quercetin glycosides rutin, hyperoside, quercitrin, quercetin-3-O-arabinoside Kaempferol -SJ-O-dirhamnoside, k-3-O-rhamnoside and -3-0-arabinoside... 

Flavonols Quercetin, kaempferol and myricetin and their glycosides (rutin, etc.) Widely distributed. Main sources Onions, apples, tea, red grapes, and broccoli, citrus fruits and maize. Antiproliferative effect [69], Inhibition of angiogenesis [108], Cardiovascular properties [115, 116], protection of DNA damage [60, 137, 138.]. 10-500... 

End products of oinnamate metabolism in buckwheat, the flavonol glycoside rutin and the depside chlorogenio acid, had little, if any, effect on the intracellular PAL-activity. The crucial question is, however, whether these compounds penetrate to the intracellular site of PA.L. Thus, any definite statement on the absence of... 

The process of auxin transport can be inhibited by a group of synthetic compounds which bind to a specific cell membrane receptor. Several flavonoids, including quercetin (7), apigenin (5), and kaempferol (6), can specifically compete with one of the synthetic compounds, naphthylphthalamic acid, at micromolar levels for binding to the receptor and, thereby, perturb auxin transport in a variety of plant tissues (Jacobs and Rubery, 1988). Although quercetin (7) was highly active, a common quercetin glycoside, rutin (35) proved inactive. 

An interesting reaction is that of the flavones with aluminum ions. The very faintly yellow-colored flavones can be made to dye tissues a bright yellow. An instance occurred within the author s experience, when a tripe-dresser complained that when boiled with onions in an aluminum kettle his tripe became bright yellow in color. This was due to the quercetin glycosides (rutin, etc.) present in the yellow-skinned onions he had happened to use. Had he chosen purple-skinned or white-skinned varieties this difficulty would probably not have been encountered, since these contain much smaller quantities of flavone (c/. p. 283). 

The extract samples 1-6 are characterized by a fairly homogeneous pattern of 6-8 blue fluorescent zones in the -range 0.15-0.80. In this I -range Mulberrosid A (Tl) can be identified at =0.30. The flavonoid Morin (T4) could be detected as blue-green fluorescent zone at =0.96. In the extract samples 2 and 6 the main constituents are hardly visible. The flavonol-glycosides Rutin (T2) and Hyperosid (T3) could be only detected in extract sample 8 (Folium Mori) which was chromatographed for comparison. The extract sample 7 (Cortex Mori), however, shows a blue fluorescent zone profile which is similar to that of Ramulus Mori. 

The hesperidin frequently is accompanied by another glycoside, erio-dictyol glycoside. This substance has been shown to be closely related to hesperidin. The methoxyl group (see above formula) is replaced by a hydroxyl group, and the sugar component is L-rhanmose rather than rutinose (10), The glycoside rutin is 3-(3,5,7,3, 4 -pentahydroxyflavone) rutinoside. 

The endocarp makes the fleshy part with usually 3 to 6 separate sections/segments. The juicy sacs inside the segments are called juice vesicles which are actually specialized hair cells (Sinha et al., 2012). F. japonicayaice (umipe fruit) has been foimd to contain flavanone glycosides poncirin, dydimin, hesperidin, flavonol glycoside (rutin) and flavone glycosides like rhoifolin (Barreca et al, 2011). 

FIGURE 1. Effects of glycosidases on the mutagenicities of flavonol glycosides. Rutin (a) and astragalin (b) were preincubated with hesperidinase ( ), jS-glucosidase (O), or no addition (A), and the mutation assay was then carried out by the preincubation method with S-9 Mix and strain TA98. 

The system was applied to monitor the radical-scavenging reaction for a number of AOXs at different pHs and reaction times. The TEAC values were found to be dependent on these parameters for almost all studied compounds (Table 31.1). Only Tr and Asc reacted rapidly (99% < 10 s) with ABTS +, and their antioxidative capacity was not affected by the end-point time. Structurally similar compounds had the same pH-dependent behavior even if they differed significantly in TEAC values, for example, the TEAC values for (-l-)-catechin and (-)-epicatechin, caffeic acid, and ferulic acid. The same was observed for quercetin and its glycoside rutin the higher activity of quercetin had been reported [74]. Independent of time and pH effects, quercetin, gallic acid, (+)-catechin, and (-)-epicatechin have shown higher activities. 

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