kaempferol-3-O-rutinoside Research Articles

Clerodane and labdane diterpene glycosides from a Malagasy endemic plant, Cussonia racemosa

Four clerodane glycosides, cussosides A–D, and one labdane glycoside, cussoside E were isolated from the dried leaves of Cussonia racemosa, along with two known flavonol glycosides identified as rutin and kaempferol rutinoside. The structures of the compounds were deduced on the basis of their physical and spectral data.

Preventive effects of Impatiens balsamina on the hen egg-white lysozyme (HEL)-induced decrease in blood flow.

Monitoring the blood flow of unanesthesized mice was found to be a reliable and effective method for studying their anaphylactic responses, in addition to the known method of monitoring blood pressure. Hen egg-white lysozyme (HEL)-specific anaphylaxis in mice was estimated by monitoring the decrease in blood flow with a Doppler blood flow meter. This method is convenient for searching for both anaphylaxis and anti-anaphylactic substances from natural products. Using this system, we estimated the anti-anaphylactic effects of the 35% ethanol extract (IB) of petals of Impatiens balsamina L., as well as those of anti-allergic agents currently used. Kaempferol 3-rutinoside and lawsone from IB significantly inhibited the decrease of blood flow. We also found that platelet-activating factor (PAF) and serotonin participate in decreasing the blood flow, but histamine does not.

Antipruritic and antidermatitic effect of extract and compounds of Impatiens balsamina L. in atopic dermatitis model NC mice.

We examined the effects of a 35% ethanol extract (IB) from the petals of Impatiens balsamina L. and the principal active compounds from IB on chronic and serious pruritus and the development of dermatitis using NC mice, a model of atopic dermatitis. IB at 100 mg/kg significantly inhibited serious scratching behaviour in the NC mouse with established dermatitis when administered i.v. 1 h before, or p.o. 24 h before the measurement. A 10 microg/kg dose of kaempferol 3-rutinoside and 2-hydroxy-1,4-naphthoquinone (lawsone) isolated from IB also inhibited scratching behaviour in the NC mouse with established dermatitis. When 4-week-old NC mice with no symptoms were administered orally 100 mg/kg/day of IB until 13 weeks of age, protection was also noted against scratching behaviour during the development of dermatitis. IB was effective for the prevention and treatment of atopic dermatitis.

Flavonoid content of commercial capers ( Capparis spinosa, C. sicula and C. orientalis ) produced in mediterranean countries

The flavonol content of commercial capers (pickled flower buds of Capparis spinosa L., C. sicula Veill. in Duham. and C. orientalis Veill. in Duham.) produced in different Mediterranean countries (Spain, Italy, Greece, Turkey and Morocco) has been analysed. The content of quercetin 3-rutinoside, kaempferol 3-rutinoside; and kaempferol 3-rhamnosyl-rutinoside as well as the aglycones (quercetin and kaempferol) were evaluated by HPLC coupled with a diode-array detector. The free aglycones were not detected in the original flower buds, indicating that they were produced during the brining process. In addition, brining extracted most of the kaempferol 3-rhamnosyl rutinoside present in the original buds, this being a minor constituent in pickled capers. The average content of flavonoid glycosides in commercial capers was 5.18 mg/g fresh weight. When this value is converted to the corresponding aglycones (quercetin and kaempferol), capers provide an average of 3.86 mg/g fresh weight. A serving of capers (10 g) will provide 65 mg of flavonoid glycosides or the equivalent 40 mg of quercetin as aglycone.

Composition and Content of Flavonol Glycosides in Green Beans and Their Fate during Processing

Four varieties of green bean (Phaseolus vulgaris) were analyzed for flavonol composition and content. Two flavonol conjugates, not previously reported in green bean, were found in three of the varieties. These are quercetin 3-O-(2G-β-d-xylopyranosylrutinoside) (1), (1.0−2.0 μg/g of fresh weight) and the corresponding kaempferol analogue (2) (0.3−0.7 μg/g). The major flavonol component in all of the varieties was quercetin 3-O-glucuronopyranoside (3) (3.5−15.1 μg/g) with lesser amounts of quercetin 3-O-rutinoside (4) (0.2−4.3 μg/g) and kaempferol 3-O-glucuronopyranoside (5) (0.5−1.3 μg/g). Kaempferol rutinoside (6) was detected in only one variety (0.8 μg/g). Commercial processing, such as canning, did not result in chemical breakdown of the conjugates, although between 8.8 and 24.4%, depending on the conjugate, was leached into the cooking water. Keywords: Phaseolus; green bean; HPLC; flavonol; glycoside

Estrogenic Flavonoids from Artemisia vulgaris L.

The comprehensive quantitative analysis of the flavonoid chemistry of Artemisia vulgaris L., a plant used as an emmenagogue in traditional medicine, is presented in conjunction with an evaluation of its estrogenic activity. Twenty known flavonoids were isolated and identified as tricine, jaceosidine, eupafolin, chrysoeriol, diosmetin, homoeriodictyol, isorhamnetin, apigenin, eriodictyol, luteolin, luteolin 7-glucoside, kaempferol 3-glucoside, kaempferol 7-glucoside, kaempferol 3-rhamnoside, kaempferol 3-rutinoside, quercetin 3-glucoside, quercetin 3-galactoside, quercetrin, rutin, and vitexin. The most abundant compounds were eriodictyol and luteolin. The estrogenic activity of all flavonoids was assayed by employing a reconstituted estrogen transcription unit in Saccharomyces cerevisiae transformed with both a human estrogen receptor expression plasmid and a reporter plasmid. Two flavonoids, eriodictyol and apigenin, were able to induce the transcription of the reporter gene in transgenic yeast. The transcriptional activity increased proportionally with increased amounts of purified eriodictyol or apigenin added to the yeast cells.

Flavonoids of four Cleome and three Capparis species

The aerial parts of four Cleome and three Capparis species were investigated for their flavonoid constituents. Thirteen flavonoid glycosides were isolated and identified as kaempferol 7-rhamnoside, kaempferol 3-rutinoside, kaempferol 3,7-dirhamnoside, kaempferol 3-glucoside-7-rhamnoside, kaempferol 3-rhamnoside-7-glucoside, quercetin 7-rhamnoside, quercetin 3-rutinoside, quercetin 7-rutinoside, quercetin 3,7-dirhamnoside, quercetin 3-glucoside-7-rhamnoside, isorhamnetin 3-rutinoside, isorhamnetin 3,7-dirhamnoside, and apigenin 6,8-di-C-glucoside.

Protection by Naringin and Some Other Flavonoids of Hepatocytic Autophagy and Endocytosis against Inhibition by Okadaic Acid

In isolated rat hepatocytes, the protein phosphatase inhibitor okadaic acid exerts a strong inhibitory effect on autophagy, which can be partially overcome by certain protein kinase inhibitors like the isoflavone genistein. To see if other, more specific okadaic acid antagonists could be found among the flavonoids, 55 different flavonoids were tested for their effect on okadaic acid-inhibited autophagy, measured as the sequestration of electroinjected [3H]raffinose. Naringin (naringenin 7-hesperidoside) and several other flavanone and flavone glycosides (prunin, neoeriocitrin, neohesperidin, apiin, rhoifolin, kaempferol 3-rutinoside) offered virtually complete protection against the autophagy-inhibitory effect of okadaic acid. Unlike genistein, these compounds had little or no autophagy-inhibitory effect of their own. Their innocuousness appeared to be related to glycosylation, because the corresponding aglycones (naringenin, eriodictyol, hesperetin, apigenin, kaempferol) were all inhibitory, in particular apigenin (80% inhibition at 100 microM). Naringin, the most potent okadaic acid-antagonistic flavonoid, gave half-maximal protection at 5 microM and maximal effect at 100 microM. Naringin also prevented the okadaic acid-induced inhibition of endogenous, autophagic lysosomal protein degradation and of receptor-mediated asialoglycoprotein uptake and degradation. Naringin and other okadaic acid-antagonistic flavonoids may be useful tools in the study of intracellular protein phosphorylation and could have potential therapeutic value as protectants against pathological hyperphosphorylations, environmental toxins, or side effects of chemotherapeutic drugs.

Flavonoid O-Glycosides from the leaves of Morinda morindoides

Eight known flavonoids: quercetin, quercetin 7,4′-dimethylether, luteolin 7-glucoside, apigenin 7-glucoside, quercetin 3-rhamnoside, kaempferol 3-rhamnoside, quercetin 3-rutinoside, kaempferol 3-rutinoside, and a new glycoside, chrysoeriol 7-neohesperidoside, were isolated from the leaves of Morinda morindoides. Their structures were established by the combined use of chemical and spectroscopic methods.

Einflu� von Sorte, Reifezustand und Behandlung auf die phenolischen Verbindungen von Aprikosens�ften und Konfit�ren

High-performance liquid chromatography with diode-array detection was used to characterize the phenolic profile of apricot fruits, juices and jams. Chlorogenic acid was the major phenolic compound present in all samples. Quercetin 3-rutinoside was the main flavonoid and kaemp-ferol 3-rutinoside was present in smaller amounts with traces of other quercetin and kaempferol glycosides. Quantitative differences in phenolics were observed in eleven apricot fruit varieties at three stages of maturity and also in some processed apricot products. A common phenolic profile was observed in all cases. The major portion of the flavonoids occurred in the skin of the fruit and the total phenolic content of apricot fruits had no influence over the softening behaviour observed in some varieties.

Flavonoids released by carrot (Daucus carota) seedlings stimulate hyphal development of vesicular-arbuscular mycorrhizal fungi in the presence of optimal CO2 enrichment

Carbon dioxide has been previously identified as a critical volatile factor that stimulates hyphal growth ofGigaspora margarita, a vesiculararbuscular mycorrhizal fungus, and we determined the optimal concentration at 2.0%. The beneficial effect of CO2 on fungal development is also visible in the presence of stimulatory (quercetin, myricetin) or inhibitory (naringenin) flavonoids. Sterile root exudates from carrot seedlings stimulate the hyphal development ofG. margarita in the presence of optimal CO2 enrichment. Three flavonols (quercetin, kaempferol, rutin or quercetin 3-rutinoside) and two flavones (apigenin, luteolin) were identified in carrot root exudates by means of HPLC retention time. Flavonols like quercetin and kaempferol are known to have stimulatory effects on hyphal growth ofG. margarita.

A chemotaxonomic study of flavonoids in the leaves of six Trichosanthes species

The 7-, 3′- and 4′-glucosides of luteolin, the 7-glucoside and 6,8-di- C-glucoside of apigenin were isolated from Trichosanthes kirilowii var. japonica. Kaempferol 3,7-di-rhamnoside and 3-glucoside-7-rhamnoside were identified from T. cucumeroides, kaempferol 3-galactoside and 3-sophoroside were also identified from T. anguina. Quercetin-3-rutinoside was detected from T. multiloba and T. rostrata. T. bracteata afforded luteolin 3′-glucoside and kaempferol 3-rutinoside, and T. kirilowii afforded luteolin 7-, 3′- and 4′-glucosides and apigenin 7-glucoside.

だったんそば（?EＦａｇｏｐｙｒｕｍ ｔａｔａｒｉｃｕｍ?F Ｇａｅｒｔｎｅｒ）種子のフラボノイド

Five flavonoids were isolated from seeds of tatari buckwheat (Fagopyrum tataricum Gartner). By the spectral analysis and the direct comparisons of the isolates and their hydrolyzed products with the authentic flavonoids, they were assigned as quercetin, kaempferol, kaempferol 3-rutinoside, rutin and quercetin 3-rutinoside-7-galactoside respectively.

Anthocyanin, flavonol copigments, and pH responsible for larkspur flower color

The anthocyanin and flavonol glycosides in Larkspur flowers (cv. Dark Blue Supreme) are delphinidin 3-di(p-hydroxybenzoyl)glucosylglucoside, kaempferol 3-robinobioside-7-rhamnoside (robinin), kaempferol 3-rutinoside, kaempferol 7-rhamnoside, and kaempferol 3-(caffeylgalactosylxyloside)-7-rhamnoside. As young flowers age the pH of epidermal tissue increases from 5·5 to 6·6 and the color of many of the cells changes from moderate reddish-purple to light purplish-blue. Many of the older cells also contain blue crystals. Visible absorption spectra of moderate reddish-purple and light purplish-blue cells were simulated with a solution of the anthocyanin (10−2 M) plus robinin (5 × 10−3 M) at pH 5·6 and 7·1, respectively. Changes in the absorption spectra of living tissue with heating or cooling and of concentrated solutions of the anthocyanin with dilution or moderate heat, indicate that in the natural state the pigment is present in an associated form.

Flavonoids of the North American species of Leucophysalis (Solanaceae)

The known flavonoids, quercetin 3-rutinoside-7-glucoside, kaempferol 3-rutinoside-7-glucoside, quercetin 3,7-diglucoside, rutin, kaempferol 3-rutinoside, quercetin 3-glucoside, kaempferol 3-glucoside, quercetin 7-glucoside, and kaempferol 7-glucoside were found in leaf extracts of Leucophysalis nana and L. grandiflora; the latter species also contained kaempferol 3,7-diglucoside.