Flavonoid Glycosides of <i>Barbarea vulgaris</i> L. (Brassicaceae)

Senatore, Felice; D'Agostino, Mario; Dini, Irene

doi:10.1021/jf990625k

Cited by 46 publications

(31 citation statements)

References 9 publications

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“…38,39 Except Barbarea intermedia, the dicots generally had a higher polyphenolic content than the monocot graminaceous Festuca nigrescens, a general trend in Most of these findings are in agreement with those reported for the genus Festuca, 40,41 for Achillea millefolium (Asteraceae), 42 Barbarea (Cruciferae = Brassicaceae), 43 Galium verum (Rubiaceae), 44 Knautia arvernensis, 45 Ranunculus acris (Ranunculaceae) 46 and Rumex acetosella (Polygonaceae). 47 Large amounts of chlorogenic acid were also found in the genus Tragopogon, 48 as in other species of the Compositae family, 49 and verbascoside (= acteoside) was the main polyphenol in leaves of Plantago lanceolata (Plantaginaceae).…”

Section: Phenolic Composition Of the Pasture And Of Collected Plantssupporting

confidence: 64%

Polyphenolic composition of a permanent pasture: variations related to the period of harvesting

Fraisse¹,

Carnat²,

Viala

et al. 2007

J Sci Food Agric

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Phenolics contribute to the micronutrient composition of forages, which in turn may affect animal product composition. To assess the importance of these compounds, the polyphenolic and botanical composition of a permanent mountain pasture in the Massif Central (France) were studied at three stages of growth. Phenolic fractions (acids, flavonoids and total) were analysed using HPLC and specific colorimetric methods over the whole pasture and in nine main species. On a botanical level, 43 species including 31 dicotyledons composed a mountain variant of Cynosurion grouping. Over time, the species growing on the field changed, the main plants being Festuca nigrescens and eight dicotyledons. In whole pasture, about 170 different compounds were separated by HPLC, of which only 30 were common to all stages. The total polyphenolic content was estimated as 31, 32 and 19 g kg −1 DM for the three stages. They were mainly composed of dihydroxycinnamic derivatives (3,5-di-O-caffeoylquinic, chlorogenic, 1,5-di-O-caffeoylquinic acids), and of flavonoids in lesser proportions. Some polyphenols were peculiar to a few species and others were ubiquitous. The two major dicaffeoylquinic acids were identified for the first time in Achillea millefolium and Knautia arvernensis. Colorimetric measurements of phenolic fractions were in good agreement with HPLC analysis (P < 0.01) for all species studied. Thus, on the mountain pasture studied, a cow would be expected to ingest up to 500 g of polyphenols daily, which could affect the quality of animal products.

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Section: Phenolic Composition Of the Pasture And Of Collected Plantssupporting

confidence: 64%

Polyphenolic composition of a permanent pasture: variations related to the period of harvesting

Fraisse¹,

Carnat²,

Viala

et al. 2007

J Sci Food Agric

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“…C-NMR) with reported values [22][23][24][25][26][27][28][29][30] or commercial samples. 31) Sinocrassoside A 1 (1) Table 8.…”

Section: Methodsmentioning

confidence: 99%

Bioactive Constituents from Chinese Natural Medicines. XXIV. Hypoglycemic Effects of Sinocrassula indica in Sugar-Loaded Rats and Genetically Diabetic KK-Ay Mice and Structures of New Acylated Flavonol Glycosides, Sinocrassosides A1, A2, B1, and B2

et al. 2007

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Sinocrassula indica (Crassulaceae) is a biennial plant distributed on the mountain areas in China (e.g., Yunnan, Guangxi, Sichuan, Guizhou, and Hunan provinces). The whole plant of S. indica has been used for the treatment of hepatitis and otitis media in Chinese traditional medicine. 2)This plant also has been used as a vegetable and a herbal tea in Chinese local areas such as Guangxi province. However, chemical constituents from this herbal medicine were left uncharacterized. During the course of our studies on bioactive constituents from Chinese natural medicines, 1,[3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] we found that the methanolic extract of the whole plant of S. indica inhibited the increase in serum glucose levels in both sucroseand glucose-loaded rats. From the methanolic extract, four new acylated flavonol glycosides, sinocrassosides A 1 (1), A 2 (2), B 1 (3), and B 2 (4), were isolated together with 11 flavonoids (5-15) and 2 megastigmanes (16,17). This paper deals with antidiabetic activities of the methanolic extract from S. indica as well as the isolation of the constituents from this extract including the structure elucidation of 1-4.Hypoglycemic Effects of the Methanolic Extract from S. indica The dried whole plant of S. indica was extracted with methanol to give a methanolic extract (7.7% from the dried plant). As shown in Tables 1 and 2, the methanolic extract significantly inhibited the increase in serum glucose levels after oral administration of sucrose and glucose in rats at doses of 250 and 500 mg/kg (p.o.). However, the extract did not show significant effect on increase of these levels after intraperitoneal administration of glucose. These findings suggested that the absorption of glucose in the intestinal tract was suppressed by the extract.The delay of sugar absorption after ingesting a meal has recently been found to be effective for type 2-diabetic patients, and the speed of gastric emptying is important in the regulation of glucose homeostasis.19) The effect of the above extract on gastric emptying (GE) after administration of 10% glucose in rats was examined. As shown in Table 3, the inhibitory effect of the extract was observed, but it was weaker than the effects of lowering of blood glucose levels. These findings indicated that the extract inhibited not only gastric emptying but also glucose absorption via Na ϩ /glucose cotransporter, 20) although more detailed examination is needed. The effect of the extract on serum glucose levels in KK-A y mice, a genetically type II diabetic mice, was also examined. The extract (250 and 500 mg/kg/d, p.o.) significantly inhibited these levels and tended to reduce TG levels, but not serum T-Cho or FFA levels, after administration for 2 weeks under non-fasted conditions (Table 4).On the other hand, serum glucose levels were lowered to normal (from ca. 530 to ca. 150 mg/dl) after the fasting, which was also reported previously, 21) and the extract did not affect blood glucose levels, body weight, weights of visceral fats (epidid...

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“…Glycosylated flavonols derived from quercetin and kaempferol are present in B. vulgaris (Senatore et al, 2000;Dalby-Brown et al, 2011). Consequently, the flavonols quercetin and kaempferol, the phytosterols obtusifoliol, campesterol, sitosterol, and stigmasterol, and the brassinosteroid 24-epi-brassinolide were tested as substrates.…”

Section: Heterologous Expression and In Vitro Activities Of The Ugt73csmentioning

confidence: 99%

UDP-Glycosyltransferases from the UGT73C Subfamily in Barbarea vulgaris Catalyze Sapogenin 3-O-Glucosylation in Saponin-Mediated Insect Resistance

et al. 2012

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Triterpenoid saponins are bioactive metabolites that have evolved recurrently in plants, presumably for defense. Their biosynthesis is poorly understood, as is the relationship between bioactivity and structure. Barbarea vulgaris is the only crucifer known to produce saponins. Hederagenin and oleanolic acid cellobioside make some B. vulgaris plants resistant to important insect pests, while other, susceptible plants produce different saponins. Resistance could be caused by glucosylation of the sapogenins. We identified four family 1 glycosyltransferases (UGTs) that catalyze 3-O-glucosylation of the sapogenins oleanolic acid and hederagenin. Among these, UGT73C10 and UGT73C11 show highest activity, substrate specificity and regiospecificity, and are under positive selection, while UGT73C12 and UGT73C13 show lower substrate specificity and regiospecificity and are under purifying selection. The expression of UGT73C10 and UGT73C11 in different B. vulgaris organs correlates with saponin abundance. Monoglucosylated hederagenin and oleanolic acid were produced in vitro and tested for effects on P. nemorum. 3-Ob-D-Glc hederagenin strongly deterred feeding, while 3-O-b-D-Glc oleanolic acid only had a minor effect, showing that hydroxylation of C23 is important for resistance to this herbivore. The closest homolog in Arabidopsis thaliana, UGT73C5, only showed weak activity toward sapogenins. This indicates that UGT73C10 and UGT73C11 have neofunctionalized to specifically glucosylate sapogenins at the C3 position and demonstrates that C3 monoglucosylation activates resistance. As the UGTs from both the resistant and susceptible types of B. vulgaris glucosylate sapogenins and are not located in the known quantitative trait loci for resistance, the difference between the susceptible and resistant plant types is determined at an earlier stage in saponin biosynthesis.

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Flavonoid Glycosides of Barbarea vulgaris L. (Brassicaceae)

Cited by 46 publications

References 9 publications

Polyphenolic composition of a permanent pasture: variations related to the period of harvesting

Polyphenolic composition of a permanent pasture: variations related to the period of harvesting

Bioactive Constituents from Chinese Natural Medicines. XXIV. Hypoglycemic Effects of Sinocrassula indica in Sugar-Loaded Rats and Genetically Diabetic KK-Ay Mice and Structures of New Acylated Flavonol Glycosides, Sinocrassosides A1, A2, B1, and B2

UDP-Glycosyltransferases from the UGT73C Subfamily in Barbarea vulgaris Catalyze Sapogenin 3-O-Glucosylation in Saponin-Mediated Insect Resistance

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