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Fig. 4 in A comprehensive review: Biological activity, modification and synthetic methodologies of prenylated flavonoids

Fig. 4. Synthesis of antiproliferative prenyl flavonoid derivatives (197–207). Reagents and conditions: (a) CH CN, ZnCl, Et O, HCl g, 0–5 ◦ C; (b) H O, reflux, 2 h; 3 2 2 2 (c) Me SO, K CO, acetone, rt, 0.5 h; (d) benzaldehyde or p-anisaldehyde, KOH, EtOH, H O, rt, 3 h; (e) CH –CHCH Br, K CO, acetone, reflux, 12 h; (f) heat, 2 4 2 3 2 2– 2 2 3 210 ◦ C, 4 h; (g) CH COONa, C H OH, reflux, 24 h; (h) I, pyridine, 90 ◦ C, 16 h; (i) KMnO, HIO, i-PrOH, H O, rt; (j) R R CHP + Ph3Br, n-BuLi, THF, rt, 24 h; (k) 1 3 2 5 2 4 4 2 2 3 equiv BBr3, ClCH2CH2Cl, rt, 2 h; (l) 8 equiv BBr3, ClCH2CH2Cl, reflux, 4 h.

Fig. 6 in A comprehensive review: Biological activity, modification and synthetic methodologies of prenylated flavonoids

Fig. 6. Synthesis of potential MDR reversal icariin derivatives (231–236). Reagents and conditions: (a) H2SO4 (2–5 equiv), 90% EtOH, reflux; 1.5 h; (b) 20% H2SO4, MeOH, reflux, 2 h; (c) 20% H SO, MeOH, 25 ◦ C, 4 h; (d) ClSO CH, Et N, 4 h, then HCl; (e) ClSO CH, pyridine, 0 ◦ C, 3 h; then HCl; (f) ClSO NH, DMA, CH Cl, 2 4 2 3 3 2 3 2 2 2 2 0 ◦ C, 3 h; (g) ClSO H, Et N, 0 ◦ C, 3 h; then HCl.

Fig. 5 in A comprehensive review: Biological activity, modification and synthetic methodologies of prenylated flavonoids

Fig. 5. Synthesis of 4′-methoxy licoflavanone derivatives (208–230). Reagents and conditions: (a) RX, K CO, dry acetone, room temperature, 1–4 h, 75–86%; (b) 2 3 Propargyl bromide, K2CO3, dry acetone, room temperature, 2 h, 89% (c) TfN3, CuSO4 (aq.), Et3N, CH2Cl2/MeOH, 2–4 h, 90–96% (d) Sodium ascorbate, R–N3, CuSO4⋅5H2O, t-BuOH/water (1:1), 85–93%.

Fig. 27 in A comprehensive review: Biological activity, modification and synthetic methodologies of prenylated flavonoids

Fig. 27. Synthesis of C-3-prenylated flavonoids. Reagents and conditions: (a) CH OCH Cl, K CO, acetone 0 ◦ C, RT; (b) 3-methylbut-2-enyl bromide (2 equiv), fresh 3 2 2 3 LDA (2.5 equiv), THF, 75 ◦ C–4 ◦ C, 20 h, 50%; (c) ArCHO (2 equiv), NaHMDS (3 equiv), THF, 75 ◦ C to reflux, 30 h, 13–46%; (d) 4 N HCl, MeOH, reflux, 8–15 h, 22–63%.

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Fig. 5 in Acylated saponins and flavonoid glycosides from the fruits of Stewartia koreana

Fig. 5. Effect of compound 15 on PCSK9 and LDLR in the HepG2 human hepatocellular carcinoma cell line. (A) Expression of PCSK9 was assayed by qRTPCR in cells treated with compound 15 (2, 10 and 50 μM), and berberine (Ber10, 10 μM) for 24 h. (B) Expression of PCSK9 and LDLR were assayed by western blot in cells treated with compound 15 (10, 40 and 50 μM), and berberine (Ber20, 20 μM) for 24 h *p <0.05.

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Fig. 4 in Acylated saponins and flavonoid glycosides from the fruits of Stewartia koreana

Fig. 4. Effect of compounds from S. koreana on PCSK9 and LDLR in the HepG2 human hepatocellular carcinoma cell line. (A) Expression of PCSK9 mRNA was assayed by qRT-PCR in cells treated with compounds (50 μM), and berberine (Ber20, 20 μM) for 24 h. (B) Expression of LDLR mRNA was assayed by qRTPCR in cells treated with compounds (50 μM), and berberine (Ber20, 20 μM) for 24 h.

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Fig. 2 in Acylated saponins and flavonoid glycosides from the fruits of Stewartia koreana

Fig. 2. (A) Key HMBC (from H to C) and 1H–1H COSY correlations for compounds 1–3. (B) ROESY correlations of aglycone of compound 1.

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Fig. 7 in Epimesatines A-I, nine undescribed prenylated flavonoids with SPHK1 inhibitory activities from Epimedium sagittatum maxim

Fig. 7. (A) Viabilities of A549 cells after treated by compounds 1–4, 8–19, and 6 at the concentration of 10 μM. (B) Viabilities of BEAS-2B cells after treated by 1, 9, 11, and 16 at the concentration of 10 μM. (C) Effects of 1, 9, 11, and 16 on the expression of SPHK1 in A549 cells. 5-Fluorouracil (5-FU) was used as positive control. *P <0.05, **P <0.01. Each bar and vertical line represents the mean ± SD of the values from four independent experiments.

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Fig. 4 in Epimesatines A-I, nine undescribed prenylated flavonoids with SPHK1 inhibitory activities from Epimedium sagittatum maxim

Fig. 4. ECD spectra of the [Rh2(OCOCF3)4] complexes of compounds 4 and 5 with the intrinsic ECD spectrum subtracted.

Fig. 5 in Hypoglycemic flavonoids from Selaginella tamariscina (P.Beauv.) Spring

Fig. 5. Effect of compounds 1–6 on glucose consumption of normal HepG2 cells. Data are presented as mean ± SD, n = 3. *P <0.05, **P <0.01 relative to control.

Fig. 7 in Hypoglycemic flavonoids from Selaginella tamariscina (P.Beauv.) Spring

Fig. 7. Protein expression of GCK and ADCYs in control, model, DMSO, metformin, and compounds 2, 3, and 5 (1 μmol/L) as detected by immunofluorescence staining and confocal microscope analysis. The protein expression was delineated (A) and quantified (B). Experiments were performed in triplicate and quantitative results are shown as the mean SD, n 3. Image magnification: 200. *P <0.05 and **P <0.01 relative to control. #P <0.05 and ##P <0.01 relative to model. a: ± = × GCK; b: ADCY2; c: ADCY3; d: ADCY8; e: ADCY9.

Fig. 6 in Hypoglycemic flavonoids from Selaginella tamariscina (P.Beauv.) Spring

Fig. 6. Effect of compounds 1–6 on glucose consumption for insulin-resistant HepG2 cells. Data are presented as mean ± SD, n = 3. *P <0.05 relative to control. # P <0.05 and ## P <0.01 relative to model.

Fig. 4 in Hypoglycemic flavonoids from Selaginella tamariscina (P.Beauv.) Spring

Fig. 4. Effects of compounds 1–6 on cell viability of HepG2 cells. Data are presented as mean ± SD, n = 3. *P <0.05 relative to control.

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Fig. 4 in Phenolic fingerprints of the Pacific seagrass Phyllospadix torreyi - Structural characterization and quantification of undescribed flavonoid sulfates

Fig. 4. Inter-annual variation in the amounts of phenolic compound in fresh (samples Phy1-F to Phy5-F) and detrital (sample Phy-3 D). Concentrations values on ordinate are given as mg g ¡1 dw of plant tissue, mean values SD (n 3). Products are given in order of elution: Caff: 1; Nep7,4': 2; OMeLu2S: 3; 6OHLu2S: 4; ± = Coum: 5; Lu2S: 6; Nep2S: 7; 5OMeLu7S: 8; 6OHLu7S: 9; RA: 10; L7S: 11; Nep7S: 12; Lu3′S: 13; Nep3′S: 14; Hispi7S: 15; Jaceo7S: 16. See Fig. 3 for formulae and Table 1 for full data.

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Fig. 3 in Phenolic fingerprints of the Pacific seagrass Phyllospadix torreyi - Structural characterization and quantification of undescribed flavonoid sulfates

Fig. 3. Structural formulae of compounds 1–18 and a-e. Underlined names indicate the previously unreported products.

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Fig. 1 in Phenolic fingerprints of the Pacific seagrass Phyllospadix torreyi - Structural characterization and quantification of undescribed flavonoid sulfates

Fig. 1. Schematic map showing the location of the sampling sites in La Jolla, San Diego County, California, USA. 1: site for fresh material. 2: site for detrital material.

Fig. 5 in BiP-overexpressing soybean plants display accelerated hypersensitivity response (HR) affecting the SA-dependent sphingolipid and flavonoid pathways

Fig. 5. Analysis of 2D Scores Plot by Partial Least Squares Discriminant Analysis (PLS-DA) of characterized flavonoids in soybean leaves from the C9 and WT genotypes, infected (I) or noninfected (NI) by P. s. pv. tomato 36 h after inoculation. Points represent replicates analyzed, whereas ellipses indicate 95% confidence region.

Fig. 9 in BiP-overexpressing soybean plants display accelerated hypersensitivity response (HR) affecting the SA-dependent sphingolipid and flavonoid pathways

Fig. 9. Expression analysis of target genes performed by qRT-PCR involved in plant bacterial interactions from BiP-overexpressing (C9) and wild-type (WT) soybean plants infected (I) or noninfected (NI) with P. syringae pv. tomato. The expression levels were obtained using the 2-ΔCT method. Bars (mean SE; ± n = 4) with the same capital letters indicate no significant difference between control and inoculated treatments and those followed by the same lowercase letters indicate no significant difference among genotypes within the same treatment (Student's test: P <0.05).

Fig. 8 in BiP-overexpressing soybean plants display accelerated hypersensitivity response (HR) affecting the SA-dependent sphingolipid and flavonoid pathways

Fig. 8. Relative abundance of the flavonoid derivatives from BiP-overexpressing (C9) and wild-type (WT) soybean plants infected (I) or noninfected (NI) with P. syringae pv. tomato. Bars (mean ± SE; n = 4) with the same capital letters indicate no significant difference between control and inoculated treatments and those followed by the same lowercase letters indicate no significant difference among genotypes within the same treatment (Student's test: P <0.05).

Fig. 4 in BiP-overexpressing soybean plants display accelerated hypersensitivity response (HR) affecting the SA-dependent sphingolipid and flavonoid pathways

Fig. 4. Absolute concentrations of phytohormones (A) and of flavonoid aglycones (B) by UHPLC/MS QqQ. The data represent the mean ± standard error. Bars (mean ± SE; n = 4) with the same capital letters indicate no significant difference between control and inoculated treatments and those followed by the same lowercase letters indicate no significant difference among genotypes within the same treatment (Student's test: P <0.05).