Kaempferol 3-sophoroside

Straubinger, M. et al.. Two kaempferol sophorosides from Crocus sativus, Nat. Prod. Lett., 10, 213, 1997. 

Disaccharide from Sophora japonica, obt. by hydrol. of Stevioside or Kaempferol-sophoroside. Also occurs as glycosides in Torulopsis magnoliae and prod, by various Acetobacter spp. Needles (MeOH aq.). Mp 196-198°. [a]g +33 +19.1 (c, 1.2 in H2O). 

Figure 7.7 MS2[M—H] and MS3 [(M—H) Yq] of isomeric flavonol tetragluco-sides (a) kaempferol-3-0-sophorotrioside-7-0-glucoside (b) kaempferol-3-0-sophoroside-7-O-sophoroside (Ferreres et al., 2004).

The MS3[(M—H) Yq] event (Figure 7.7) revealed the ions resulting from the fragmentation of the glycoside in position 3. The same behavior is also observed in the case of kaempferol 3-sophorotrio-side-7-sophoroside (a pentaglycoside) (Ferreres et ah, 2004) in which... 

White cabbage is rich in flavonol glucosides, where acylated and unacylated tri- and tetraglucosides of kaempferol and quercetin have been isolated and identified (Nielsen et al., 1993 1998). In broccoli florets, the main flavonol glycosides were identified as sophorosides of quercetin and kaempferol, but all the fiavonoids have not yet been determined. The fiavonols were present in raw florets at 65 mg kg and 166 mg kg fresh weight, respectively (Price et al.,... 

Oligosaccharides in combination with phenols may also be removed intact by careful hydrolysis with acid. Thus, when rutin is heated with 10% aqueous acetic acid, it yields rutinose. Dilute mineral acids can, for example, be used for the removal of sophorose from kaempferol 3-sophoroside, " and of gentiobiose from p-hydroxyphenyl 9-gentiobio-side. A comparison of the use of formic acid-cyclohexanol and hydrochloric acid-acetic acid for the partial hydrolysis of glycosides has been made by Chandler and Harper. There appears to be no general rule governing the use of these acids. 

In a study on the antioxidant effects of the components from H. diffusa on xanthine-xanthine oxidase cytochrome c, Lu et al. found that quercetin 3-0-sambubioside (22) and quercetin 3-0-sophoroside (23) are superoxide radical scavengers. The kaempferol glycoside (18) and the itidoid glycosides having cinnamoyl or feruloyl substituents on the glucose units [(31) and (33)], as well as asperuloside (48), were found to be inactive in this assay [29]. 

In the deep F range appear from I =0.65 to the start 9-10 yellow and orange fluorescent zones which can be assigned to the known or not yet identified flavon- and flavonol di-, tri- and tetraglycosides of quercetin or kaempferol (e.g. sophorosides, gentiobiosides etc.). 

Figure 7.13 Broccoli florets contain flavonol sophorosides and conjugated derivatives of sinapic acid while kaempferol-3,7-0-diglucoside is among the flavonols present in cabbage leaves.

Kaempferol 3-sophoroside Alsophila spinulosa Tryon ( = Cyathea spinulosa Wall., C.fauriei Copel., C. taiwaniana Nakai) 197 ... 

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