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Fig. 5. Total ubiquinone-9 in 3-O-glycosylation of kaempferol restricts the supply of the benzenoid precursor of ubiquinone (Coenzyme Q) in Arabidopsis thaliana

Fig. 5. Total ubiquinone-9 content in the rosette leaves of wild-type, ugt78d2, f3′h, and f3′h/ugt78d2 plants. Plants were grown on soil in 16-h days (110 μE m 2 s 1) at 22 ◦C for 3 weeks. Data represent the means of 7–8 biological replicates ±SE. P values from an analysis of variance between each mutant and the wild-type reference are indicated above the bars. The asterisk indicates significant differences from the wild type as determined by variance analysis (P <α = 0.1).

Fig. 4. 4 in 3-O-glycosylation of kaempferol restricts the supply of the benzenoid precursor of ubiquinone (Coenzyme Q) in Arabidopsis thaliana

Fig. 4. 4-hydroxybenzoate content in A. thaliana roots and rosette leaves. Roots were harvested from 17-day-old axenic cultures, while rosette leaves were harvested from 3-week-old plants grown on soil. Samples were processed with and without acidic hydrolysis, and 4-hydroxybenzoate was quantified by HPLCspectrophotometry. Data represent the means of 3–4 biological replicates ± SE. P values from an analysis of variance between the ugt78d1/ugt78d2 knockout and the wild-type reference are indicated above the bars. Threshold for statistically significant differences between ugt78d1/ugt78d2 and wild-type data as determined by variance analysis was P <α = 0.1. n.d.: not detected.

Fig. 1 in 3-O-glycosylation of kaempferol restricts the supply of the benzenoid precursor of ubiquinone (Coenzyme Q) in Arabidopsis thaliana

Fig. 1. Metabolic origins of 4-hydroxybenzoate for ubiquinone biosynthesis in plant cells. Note that chemical modeling of the peroxidative cleavage of kaempferol predicts that peroxidases do not act on kaempferol itself, but on its α-diketone tautomer. The formation of the latter is contingent on the presence of a double bond between C-2 and C-3 and a free C-3- OH on the C-ring. Dashed arrows indicate unknown and/or multiple steps. Ara, arabinosyl; Glu, glucosyl; Rha, Rhamnosyl; UGT78D1, flavonol 3-O-rhamnosyltransferase; UGT78D2, flavonol 3-O-glucosyltransferase; UGT78D3, flavonol 3-O- arabinosyltransferase.

Fig. 3 in 3-O-glycosylation of kaempferol restricts the supply of the benzenoid precursor of ubiquinone (Coenzyme Q) in Arabidopsis thaliana

Fig. 3. Total ubiquinone content and rate of de novo ubiquinone biosynthesis in A. thaliana. A) Total ubiquinone-9 content in the rosette leaves of 3-week-old wild-type, ugt78d1, ugt78d2, ugt78d3 and ugt78d1/ugt78d2 plants grown on soil. B) Relative ubiquinone-9- [Ring-13C] labeling in the leaves of axenically 6 grown wild-type, ugt78d1, ugt78d2, ugt78d3 and ugt78d1/ugt78d2 plants fed for 3h with 250 μM of phenylalanine-[Ring- 13C]. Data represent the means of 4–6 6 biological replicates ± SE. P values from an analysis of variance between each mutant and the wild-type reference are indicated above the bars. Asterisks indicate significant differences from the wild type as determined by variance analysis (P <α = 0.1).

Figure 4 from: Yoncheva K, Hristova-Avakumova N, Hadjimitova V, Traykov T, Petrov P (2020) Evaluation of physicochemical and antioxidant properties of nanosized copolymeric micelles loaded with kaempferol. Pharmacia 67(2): 49-54. https://doi.org/10.3897/pharmacia.67.e38648

Figure 4 DPPH and anion superoxide scavenge capacity of free kaempferol (KF) and micellar kaempferol; (a) KF-PDMAEMA13-b-PPO69-b-PDMAEMA13 micelles, (b) KF-PDMAEMA9-b-PCL70-b-PDMAEMA9 micelles. Mean ± SD (n=3).

Figure 1 from: Yoncheva K, Hristova-Avakumova N, Hadjimitova V, Traykov T, Petrov P (2020) Evaluation of physicochemical and antioxidant properties of nanosized copolymeric micelles loaded with kaempferol. Pharmacia 67(2): 49-54. https://doi.org/10.3897/pharmacia.67.e38648

Figure 1 Size distribution of kaempferol loaded polymeric micelles prepared from PDMAEMA9-b-PCL70-b-PDMAEMA9 and PDMAEMA13-b-PPO69-b-PDMAEMA13 triblock copolymers.

Figure 3 from: Yoncheva K, Hristova-Avakumova N, Hadjimitova V, Traykov T, Petrov P (2020) Evaluation of physicochemical and antioxidant properties of nanosized copolymeric micelles loaded with kaempferol. Pharmacia 67(2): 49-54. https://doi.org/10.3897/pharmacia.67.e38648

Figure 3 In vitro release of kaempferol from PDMAEMA9-b-PCL70-b-PDMAEMA9 and PDMAEMA13-b-PPO69-b-PDMAEMA13 micelles in distilled water.

Figure 2 from: Yoncheva K, Hristova-Avakumova N, Hadjimitova V, Traykov T, Petrov P (2020) Evaluation of physicochemical and antioxidant properties of nanosized copolymeric micelles loaded with kaempferol. Pharmacia 67(2): 49-54. https://doi.org/10.3897/pharmacia.67.e38648

Figure 2 AFM images of kaempferol loaded PDMAEMA9-b-PCL70-b-PDMAEMA9 (left) and PDMAEMA13-b-PPO69-b-PDMAEMA13 (right) micelles.

Figure 3 from: Aluani D, Kondeva-Burdina M, Tosheva A, Yoncheva K, Tzankova V (2022) Improvement of in vitro antioxidant activity of kaempferol by encapsulation in copolymer micelles. Pharmacia 69(1): 25-29. https://doi.org/10.3897/pharmacia.69.e77678

Figure 3 Effect of empty PDMAEMA-PPO-PDMAEMA (PPO) and kaempferol (KF) loaded PDMAEMA-PPO-PDMAEMA (PPO-KF) micelles (25, 50, 75 μg/ml) on the level of malondialdehyde (MDA) in non-treated rat microsomes.

Figure 5 from: Aluani D, Kondeva-Burdina M, Tosheva A, Yoncheva K, Tzankova V (2022) Improvement of in vitro antioxidant activity of kaempferol by encapsulation in copolymer micelles. Pharmacia 69(1): 25-29. https://doi.org/10.3897/pharmacia.69.e77678

Figure 5 Protective effects of free kaempferol (KF) (25, 50, 75 μg/ml) and kaempferol loaded PDMAEMA-PPO-PDMAEMA (PPO-KF) micelles on the level of malondialdehyde (MDA) in iron/ascorbic acid (Fe2+/AA) treated microsomes. Mean values ± SN (n = 6). *** p < 0.001 compared to untreated control group; +++ < 0.001 vs Fe2+/AA is considered to be statistically significant.

Figure 2 from: Aluani D, Kondeva-Burdina M, Tosheva A, Yoncheva K, Tzankova V (2022) Improvement of in vitro antioxidant activity of kaempferol by encapsulation in copolymer micelles. Pharmacia 69(1): 25-29. https://doi.org/10.3897/pharmacia.69.e77678

Figure 2 Effect of empty PDMAEMA-PCL-PDMAEMA (PCL) and kaempferol (KF) loaded PDMAEMA-PCL-PDMAEMA (KF-PCL) micelles (25, 50, 75 μg/ml) on the level of malondialdehyde (MDA) in non-treated rat microsomes.

Figure 1 from: Aluani D, Kondeva-Burdina M, Tosheva A, Yoncheva K, Tzankova V (2022) Improvement of in vitro antioxidant activity of kaempferol by encapsulation in copolymer micelles. Pharmacia 69(1): 25-29. https://doi.org/10.3897/pharmacia.69.e77678

Figure 1 Mean diameter of both types of kaempferol loaded micelles – PDMAEMA-PCL-PDMAEMA (KF-PCL) and PDMAEMA-PPO-PDMAEMA (KF-PPO).

Figure 4 from: Aluani D, Kondeva-Burdina M, Tosheva A, Yoncheva K, Tzankova V (2022) Improvement of in vitro antioxidant activity of kaempferol by encapsulation in copolymer micelles. Pharmacia 69(1): 25-29. https://doi.org/10.3897/pharmacia.69.e77678

Figure 4 Protective effects of free kaempferol (KF) (25, 50, 75 μg/ml) and kaempferol loaded PDMAEMA-PCL-PDMAEMA (KF-PCL) micelles on the level of malondialdehyde (MDA) in iron/ascorbic acid (Fe2+/AA) treated microsomes.