Isoscoparin

Food Chem. 2018 Feb 15;241:154-162.

Identification and quantification of flavonoids in yellow grain mutant of rice (Oryza sativa L.).[Pubmed: 28958514]

Flavonoids are naturally occurring phenolic compounds with potential health-promoting activities. Although anthocyanins and phenolic acids in coloured rice have been investigated, few studies have focused on flavonoids.
METHODS AND RESULTS:
Herein, we analysed flavonoids in a yellow grain rice mutant using UHPLC-DAD-ESI-Q-TOF-MS, and identified 19 flavonoids by comparing retention times and accurate mass measurements. Among them, six flavonoids, isoorientin, isoorientin 2″-O-glucoside, vitexin 2″-O-glucoside, isovitexin, Isoscoparin 2″-O-glucoside and Isoscoparin, were isolated and fully identified from the yellow grain rice mutant, and the levels were significantly higher than wild-type, with isoorientin particularly abundant in mutant embryo. Significant differences in total phenolic compounds and antioxidant activity were observed in mutant rice by DPPH, FRAP and TEAC assays.
CONCLUSIONS:
The results suggest that the representative six flavonoids may play an important role in colouration and antioxidant activity of embryo and endosperm tissue. The findings provide insight into flavonoid biosynthesis and the possibility of improving functionality in rice.

Phytother Res. 2014 Jul;28(7):1064-70.

A new phenolic component from Triticum aestivum sprouts and its effects on LPS-stimulated production of nitric oxide and TNF-α in RAW 264.7 cells.[Pubmed: 25165783]

An unusual new phenolic component, triticumoside (1), and eight known compounds, isoorientin (2), Isoscoparin (3), (2R)-2-O-β-D-glucopyranosyloxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one (4), adenosine (5), β-sitosterol (6), daucosterol (7), 6′-O-linolenoyl daucosterol (8), α-tocopherol (9), were isolated fromTriticum aestivum sprouts.
METHODS AND RESULTS:
The hybrid structure of 1, which is a hybrid between a flavone and a polyoxygenated benzene, is rarely found in natural sources. In addition, the effects of these compounds on LPS-induced NO and TNF-α production in RAW 264.7 cells were evaluated. At a concentration of 2.0 μM, compounds 2-4 significantly inhibited the production of both NO and TNF-α. Compound 1 exhibited inhibitory activity on the secretion of TNF-α at concentrations as low as 2.0 μM, but it did not reduce NO levels at any of the tested concentrations.

Mol Med Rep. 2015 Aug;12(2):3139-45.

Flavonoids from Triticum aestivum inhibit adipogenesis in 3T3-L1 cells by upregulating the insig pathway.[Pubmed: 25936595 ]

The present study aimed to compare the potential anti-adipogenic effects and underlying mechanisms of the luteolin, Isoscoparin and isoorientin flavonoids, purified from Triticum aestivum sprout (TA) in 3T3-L1 cells.
METHODS AND RESULTS:
The cells were treated with different concentrations of flavonoids for 8 days and the lipid accumulation was assessed using Oil-Red-O staining. The expression levels of the transcription factors and the genes involved in adipogenesis in the cells were assessed by reverse transcription-quantitative polymerase chain reaction and western blotting. The results demonstrated that 10 μM luteolin, Isoscoparin or isoorientin inhibited lipid deposition in the cells by 74, 63 and 65%, respectively. The flavonoids also significantly inhibited the transcriptional regulators of adipogenesis, including peroxisome proliferator-activated receptor-γ, CAAT/enhancer binding protein-α and sterol regulatory element binding protein (SREBP)-1c, compared with the control cells. Similarly, there was a significant downregulation of the adipocyte specific markers associated with lipid metabolism, including activating protein-2, fatty acid synthase, hormone-sensitive lipase and lipoprotein lipase, in the flavonoid treated cells. Notably, the cells treated with the flavonoids demonstrated increased expression levels of the insulin-induced genes, insig-1 and insig-2, which may have inhibited the activation of the adipogenic transcription factor, SREBP, eventually leading to the inhibition of adipogenesis.
CONCLUSIONS:
Taken together, these results revealed that the flavonoids from TA possessed an inhibitory effect on adipogenesis through downregulation of adipogenic transcription factors and genes associated with lipid metabolism, and the upregulation of insig 1 and 2, suggesting that the flavonoids from TA may be potential therapeutic agents for the prevention and treatment of obesity.

Nat Prod Commun. 2014 Oct;9(10):1469-72.

Identification and evaluation of flavone-glucosides isolated from barley sprouts and their inhibitory activity against bacterial neuraminidase.[Pubmed: 25522538]

Flavonoids are naturally occurring phenolic compounds with potential health-promoting activities. Although anthocyanins and phenolic acids in coloured rice have been investigated, few studies have focused on flavonoids.
METHODS AND RESULTS:
Herein, we analysed flavonoids in a yellow grain rice mutant using UHPLC-DAD-ESI-Q-TOF-MS, and identified 19 flavonoids by comparing retention times and accurate mass measurements. Among them, six flavonoids, isoorientin, isoorientin 2″-O-glucoside, vitexin 2″-O-glucoside, isovitexin, Isoscoparin 2″-O-glucoside and Isoscoparin, were isolated and fully identified from the yellow grain rice mutant, and the levels were significantly higher than wild-type, with isoorientin particularly abundant in mutant embryo. Significant differences in total phenolic compounds and antioxidant activity were observed in mutant rice by DPPH, FRAP and TEAC assays.
CONCLUSIONS:
The results suggest that the representative six flavonoids may play an important role in colouration and antioxidant activity of embryo and endosperm tissue. The findings provide insight into flavonoid biosynthesis and the possibility of improving functionality in rice.