Disease relevance of Hirsutrin

• Three flavonoids which promoted Escherichia coli topoisomerase IV-dependent DNA cleavage were isolated from cottonseed flour and identified as quercetin 3-O-beta-D-glucose-[1,6]-O-alpha-L-rhamnose (rutin), quercetin 3-O-beta-D-galactose-[1,6]-O-alpha-L-rhamnose, and quercetin 3-O-beta-D-glucose (isoquercitrin) [1].
• Quercetin (30 micromol/kg body weight) was administered either as the lipophilic aglycone or as the more hydrophilic quercetin-3-O-glucoside in test meals differing in fat content (3, 17, or 32 g fat/100 g diet) to growing pigs [2].
• Eubacterium ramulus, a quercetin-3-glucoside-degrading anaerobic microorganism that occurs at numbers of approximately 10(8)/g dry feces in humans, was tested for its ability to transform other flavonoids [3].
• The flavonoids hyperoside, isoquercitrin and quercitrin (all at 0.6 mg/kg, P. O.) and rutin (1 mg/kg, P. O.) only partially blocked OF-induced hyperthermia [4].
• There were no apparent effects of isoquercitrin on development of kidney neoplasms, hyperplasias or chronic nephropathy [5].

High impact information on Hirsutrin

• To study the possible involvement of Mrp2, we compared intestinal uptake of quercetin-3-glucoside between control and Mrp2-deficient rats, using an in situ intestinal perfusion system [6].
• The protective effect of vitamin C against DNA damage at this concentration was significantly less than that of all the flavonoids except apigenin, quercetin-3-glucoside, and rutin [7].
• Tissues exposed to red wine had significantly higher amounts of both quercetin (x 3; P < 0.001) and quercetin-3-O-glucoside (x 1.5; P < 0.01) associated with them, compared with sacs incubated in the dealcoholised equivalent [8].
• Quercetin-4'-glucoside mucosal hydrolysis was 10 times greater than quercetin-3-glucoside hydrolysis in the absence of inhibitors (449 and 47 nmol g(-1) tissue, respectively), despite the similar amounts (13+/-4 and 9+/-1 nmol g(-1), respectively) being transferred to the serosal compartment during the 15 min incubation [9].
• Bioavailability of Q3G was significantly higher when the test meal was ground beef rather than the standard ration [10].

Chemical compound and disease context of Hirsutrin

• Growing cultures of Eubacterium ramulus converted 5 mM quercetin-3-glucoside to 1.7 +/- 0.6 mM 3,4-dihydroxyphenylacetic acid, 7.6 +/- 1.0 mM acetate, and 4.0 +/- 0.4 mM butyrate [11].
• Ellagic acid derived from T. chebula fruits exerted a potent inhibitory effect against C. perfringens and E. coli, but little or no inhibition was observed with treatments of behenic acid, P-caryophyllene, eugenol, isoquercitrin, oleic acid, ca-phellandrene, 3-sitosterol, stearic acid, a-terpinene, terpinen-4-ol, terpinolene, or triacontanoic acid [12].

Biological context of Hirsutrin

• These data suggest that LPH is a major determinant of intestinal absorption of quercetin-3-glucoside in rats [13].
• Degradation of quercetin-3-glucoside in gnotobiotic rats associated with human intestinal bacteria [14].
• Quercetin-4'-glucoside is more potent than quercetin-3-glucoside in protection of rat intestinal mucosa homogenates against iron ion-induced lipid peroxidation [15].
• The inhibitory character of isoquercitrin for aldose reductase was a mix of uncompetitive and noncompetitive inhibitions, and its IC50 was 1 x 10(-6) M [16].
• Red vine leaf extract (RVLE) is a herbal medicine containing several flavonoids, with quercetin-3-O-beta-glucuronide and isoquercitrin (quercetin-3-O-beta-glycoside) as the main components [17].

Anatomical context of Hirsutrin

• Quercetin-3-glucoside is transported by the glucose carrier SGLT1 across the brush border membrane of rat small intestine [18].
• Evidently, quercetin derived from quercetin-3-glucoside passes across the small intestinal epithelium more rapidly than free quercetin aglycone [19].
• During passage across the epithelium, quercetin-3-glucoside is rapidly deglycosylated and then glucuronidated [19].
• From human feces two phenotypically different types of bacteria were isolated on quercetin-3-glucoside as carbon and energy source [11].
• Caco-2 cells absorbed low levels of quercetin 3-glucoside from apple peel extracts, but quercetin aglycon absorption was not detected [20].

Associations of Hirsutrin with other chemical compounds

• An enzyme preparation from the primary leaves of mung bean (Phaseolus aureus) was shown to catalyze the transfer of L-rhamnose from UDP-beta-L-rhamnose to the flavonol D-glucoside isoquercitrin to form rutin [21].
• (Solanaceae): quercetin 3- O-rutinoside-7- O-glucoside ( 1), kaempferol3- O-rutinoside-7- O-glucoside( 2), rutin ( 3), nicotiflorin ( 4), isoquercitrin ( 5), quercetin ( 6), and kaempferol ( 7) [22].
• Hesperetin and quercetin-3-glucoside reduced changes in H&E, 8-OHdG, TUNEL and IL-1alpha [23].
• A cell suspension culture of CANNABIS SATIVA without endogenous flavonoids is able to convert quercetin to quercetin 3- O-glucoside, quercetin 3- O-diglucoside, isorhamnetin 3- O-glucoside, and isorhamnetin 3- O-diglucoside [24].
• The 74 samples of six HYPERICUM species (H. PERFOROTUM, H. HIRSUTUM, H. MACULATUM, H. TETRAPTERUM, H. MONTANUM, AND H. HUMIFUSUM) were collected around Slovenia and analysed for the content of ten substances (rutin, hyperoside, isoquercetin, quercitrin, quercetin, I3,II8-biapigenin, amentoflavone, pseudohypericin, hypericin, and hyperforin) [25].

Gene context of Hirsutrin

• Keywords: Pectinase from Aspergillus niger; rutin; quercetin-3-glucoside; laccase; rhamnosidase; asparagus juice; antioxidant activity [26].
• Caco-2 cell homogenates demonstrated both lactase and glucosidase activities when incubated with lactose and quercetin 3-glucoside, respectively [20].
• In this study, the influence of selected flavonoids (quercetin, isoquercitrin, spiraeoside, rutin, kaempferol, naringenin, naringin, and kaempferol) on the transport of the P-gp substrate [3H]talinolol across Caco-2 cell monolayers was investigated [27].
• For example, isoquercitrin (quercetin 3-O-glucoside), one of the flavonol monoglucosides, was converted efficiently to the corresponding aromatic acid ester (isoquercitrin 6''-O-cinnamate) by a lipase with vinyl cinnamate as an acyl donor [28].

Analytical, diagnostic and therapeutic context of Hirsutrin

• HPLC analysis of the leaves indicated that G. glabra plants collected in the present study could be divided into two types, RT-type and IQ-type, according to their major flavonol glycosides, rutin or isoquercitrin, respectively [29].
• Quercitrin, isoquercitrin, hyperoside and rutin were identified in all leaf samples by means of thin-layer chromatography; the fruits contained only isoquercitrin [30].

References