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Fig. 2 in Comparison of carbohydrate partitioning and expression patterns of some genes involved in carbohydrate biosynthesis pathways in annual and biennial species of Cichorium spp.

Fig. 2. Transcript levels of FAZY genes, 1-SST (a), 1-FFT (b), 1-FEHI (c), 1-FEHII (d) in different tissues of chicory and endive at S1 and S2 stages. Transcript levels were determined by qPCR and normalized against the expression of the reference gene (RPL19). Transcript levels in different organs were expressed relative to the levels of leaves of chicory at S1. Values represent the mean of three biological replicates ± SE. Different letters indicate statistical significance at P <0.05 (Duncan's multiple range test).

Fig. 1 in Comparison of carbohydrate partitioning and expression patterns of some genes involved in carbohydrate biosynthesis pathways in annual and biennial species of Cichorium spp.

Fig. 1. Fructose (a), glucose (b) and sucrose content (c) in different tissues of endive and chicory at two stages (S1 and S2), Values represent the mean of three biological replicates ± SE. Different letters indicate statistical significance at P <0.05 (Duncan's multiple range test). 1-kestose, nystose, inulin (D) and mDP (E) in roots of chicory at two stages (S1and S2), Values represent the mean of three biological replicates ± SE. Different letters indicate statistical significance according to the LSD at 0.01 probability level.

Fig. 8 in P450 variations bifurcate the early terpene indole alkaloid pathway in Catharanthus roseus and Camptotheca acuminata

Fig. 8. Molecular models of Camptotheca CYP72A564, CYP72A565 and CYP72A730. (A) Backbone overlays of Camptotheca CYP72A730, CYP72A564 and CYP72A565 models are shown with the RMSD variance of CYP72A564 and CYP72A565 from the CYP72A730 backbone depicted in green (0.0 Å), yellow (3.0 Å) and red (4.5 Å). (B) SRS regions in CYP72A proteins shown with predicted substrate contact residues (gray fill). (C) Identical versus (D) different side chain residues predicted within 4.5 Å of loganic acid (gray) docked in Camptotheca CYP72A564 (orange) versus loganic acid (aqua) docked in CYP72A730 (magenta). (E) Identical versus (F) different side chain residues predicted within 4.5 Å of loganic acid (gray) docked in Camptotheca CYP72A565 (rose) versus loganic acid (aqua) docked in CYP72A730 (magenta).

Fig. 4 in Comparison of carbohydrate partitioning and expression patterns of some genes involved in carbohydrate biosynthesis pathways in annual and biennial species of Cichorium spp.

Fig. 4. Relative expression analysis of SUS, VI, and CWI1-3, in different tissues of chicory and endive at S1 and S2 stages. Transcript levels were determined by qPCR and normalized against the expression of the reference gene (RPL19). Transcript levels in different organs were expressed relative to the levels of leaves of chicory at S1. Values represent the mean of three biological replicates ± SE. Different letters indicate statistical significance at P <0.05 (Duncan's multiple range test).

Fig. 4 in P450 variations bifurcate the early terpene indole alkaloid pathway in Catharanthus roseus and Camptotheca acuminata

Fig. 4. LC-MS analyses of in vitro assays with purified His6-tagged CYP72A proteins reconstituted with His6-tagged CPR proteins. Reactions containing purified His6- tagged CYP72A protein, full-length His6-tagged Caa CPR1 protein (A, B) or full-length His6-tagged Caa CPR2 protein (C, D), and 250 μM loganic acid (A,C) or loganin (B,D), were incubated at 30◦ C and analyzed by LC-MS as described in experimental procedures. Extracted ion chromatograms for loganic acid (m/z 375.1297), secologanic acid (m/z 373.1140), secoxyloganic acid (m/z 389.1089); loganin sodium salt (m/z +413.1418), secologanin sodium salt (m/z +411.1262), secoxyloganin (m/z 403.1246) are given with stacked chromatograms as marked.

Fig. 3 in P450 variations bifurcate the early terpene indole alkaloid pathway in Catharanthus roseus and Camptotheca acuminata

Fig. 3. LC-MS analyses of in vitro assays with CYP72A proteins expressed in yeast microsomes. 100 μl reactions containing 10 μl CYP72A microsomes isolated from WAT11 with 250 μM loganic acid or loganin and 500 μM NADPH in 100 mM NaPO (pH 7.4) were incubated at 30◦ C and analyzed by LC-MS as 4 described in the experimental procedures. (A) Extracted ion chromatograms for loganic acid (m/z 375.1297), secologanic acid (m/z 373.1140), secoxyloganic acid (m/z 389.1089). (B) Extracted ion chromatograms for loganin sodium salt (m/z +413.1418), secologanin sodium salt (m/z +411.1262), secoxyloganin (m/z 403.1246).

Fig. 6. Type I in P450 variations bifurcate the early terpene indole alkaloid pathway in Catharanthus roseus and Camptotheca acuminata

Fig. 6. Type I binding spectra of SLAS candidates. Substrate-induced Type I binding spectra for (A) CYP72A564, (B) CYP72A565 and from 998 nM (violet) to 1.90 mM (crimson) using loganic acid (top inset) or loganin (bottom inset). (C) Binding isotherms calculated as the difference of the valley (~419 nm) from the peak (~388 nm) are shown for loganic acid () and loganin (). (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 6 in A previously undescribed phenylethanoid glycoside from Callicarpa kwangtungensis Chun acts as an agonist of the Na/K-ATPase signal transduction pathway

Fig. 6. Effect of callicarpanoside B on ERK activation in AAC-19 cells. AAC-19 cells were treated with or without 100, 1000 nM callicarpanoside B for 10 min, and the cell lysate was collected for Weston blot analysis showed in the upper panel. The statistics were combined from 3 separate experiments and are presented as mean ± SEM, showed in the lower panel. Student t-test, *, P <0.05; **, P <0.01.

Fig. 7 in A previously undescribed phenylethanoid glycoside from Callicarpa kwangtungensis Chun acts as an agonist of the Na/K-ATPase signal transduction pathway

Fig. 7. The relative binding affinity of callicarpanoside B compared with ouabain. The 3H-ouabain binding assay was utilized to determine the relative binding affinity. After preincubation with non-radioactive ouabain or callicarpanoside B to NKA for 30 min in cultured LLC-PK1 cells, 100 nM 3H-ouabain were added and incubated another 30 min. Thus, the IC50 for binding nonradioactive ouabain or callicarpanoside B to NKA was determined by competition with 3H-ouabain. The data are combined from three experiments and are presented as mean ± SD. Non-radioactive ouabain, IC50 = 0.95 ± 0.35 μM; callicarpanoside B, IC50 = 10.55 ± 3.05 μM.

Fig. 5 in A previously undescribed phenylethanoid glycoside from Callicarpa kwangtungensis Chun acts as an agonist of the Na/K-ATPase signal transduction pathway

Fig. 5. Effect of callicarpanoside B on NKA-mediated kinase activation in LLC-PK1 cells. A, LLCPK1 cells were treated with 10, 100, and 250 nM callicarpanoside B for 10 min, and the cell lysate was collected for Weston blot analysis showed in the upper panel. The data are combined from 3 to 8 separate experiments and are presented as mean ± SEM, shown in the lower panel. B, LLCPK1 cells were treated with 100 nM callicarpanoside B for 2, 10, 30, and 120 min, and the cell lysate was collected for Weston blot analysis, showed in the upper panel. The data are combined from 3 to 8 separate experiments and are presented as mean ± SEM. C, LLCPK1 cells were treated with 10, 100, and 250 nM callicarpanoside B for 10 min, and the cell lysate was collected for Weston blot. Probed for p-Src and showed in the upper panel. The data are combined from indicated separate experiments and are presented as mean ± SEM, shown in the lower panel. D, LLCPK1 cells were treated with 10, 100 nM callicarpanoside B for 15 min, and the lysates were fractioned into Cytosolic (Cy) and particulate (Pa) fractions for Weston blot analysis and Pa/Cy ratios of PKCε, contents were compared. The upper panel represents Western blot. The data are combined and presented as mean ± SEM of 3 independent experiments, shown in the lower panel. Student t-test, *, P <0.05; **, P <0.01.

Fig. 4 in A previously undescribed phenylethanoid glycoside from Callicarpa kwangtungensis Chun acts as an agonist of the Na/K-ATPase signal transduction pathway

Fig. 4. Effect of callicarpanoside B on NKA endocytosis. A, TCN-YFP-α1 cells were treated with callicarpanoside B for 6 h. Cells were fixed with Methanol. Coverslips were mounted and imaged under a fluorescence microscope described previously (Liang et al., 2006; Tian et al., 2006). B, cell surface NKA α1 was measured by biotinylation assay as described under "Experimental". Proteins were collected after treatment with different concentrations of callicarpanoside B, ouabain as a control. Cell lysates were separated by SDS-PAGE and analyzed by Western blot for NKA α1. D, quantitative dose-response endocytosed NKA α1 was calculated from four to eight independent experiments for each dose. The values are mean ± SEM. Two-way ANOVA, **, P <0.01; ***, P <0.001.

Fig. 3 in A previously undescribed phenylethanoid glycoside from Callicarpa kwangtungensis Chun acts as an agonist of the Na/K-ATPase signal transduction pathway

Fig. 3. Concentration curve of callicarpanoside B (2) on NKA inhibition. The purified NKA was incubated with different concentrations of compounds for 15 min, then assayed for ouabain-sensitive ATPase activity as described under Materials and Methods. The data are combined from three to five separate experiments and are presented as mean ± SEM.

Fig. 8 in A previously undescribed phenylethanoid glycoside from Callicarpa kwangtungensis Chun acts as an agonist of the Na/K-ATPase signal transduction pathway

Fig. 8. Effect of callicarpanoside B on cell growth. LLCPK1 cells were subcultured in 12-well plates (50,000 cells/well) and serum-starved overnight. Before treatment, three wells of day 0 were trypsinized and counted. After callicarpanoside B treatment at the indicated dose, three wells of individual control (Con) and compound-treated cells were trypsinized and counted at 48 h.

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Fig. 5 in Diverse alkaloids from the aerial parts of Aconitum carmichaelii and antiproliferative activity of costemline via inhibiting SIRT1/ROCK1/ P-STAT3 pathways

Fig. 5. The protein levels of ROCK1/SIRT1 and STAT3/P-STAT3 in colorectal cancer (CRC). (A) Western blot was used to analyze the expression or phosphorylation level of ROCK1, SIRT1 and STAT3 after HCT116 cells in the above groups were treated with 20 μM/40 μM compound 1 for 24 h. (B) At the protein level, the relative expression of SIRT1 and ROCK1/STAT3 signal was inhibited by compound 1 in HCT-116 cells. **p <0.01, ***p <0.001, ****p <0.0001 vs. control group.

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Fig. 4. Compound 1 in Diverse alkaloids from the aerial parts of Aconitum carmichaelii and antiproliferative activity of costemline via inhibiting SIRT1/ROCK1/ P-STAT3 pathways

Fig. 4. Compound 1 inhibited invasion of HCT116 colon cancer cells in a transwell assay, which showed by representative images (A) and attached data (B). Cells were incubated with compound 1 (a) 0 μM, (b) 5 μM, (c) 10 μM for 24 h (original magnification, × 200). Quantitative data are presented as the mean ± standard deviation of 3 replicates, relative to the 0 μM control group. **p <0.01 vs. the 0 μM control group.

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Fig. 5. Compound 7 induced apoptosis through a mitochondria-dependent pathway. A in Bufadienolide glycosides and bufadienolides from the whole plants of Helleborus lividus, and their cytotoxic activity

Fig. 5. Compound 7 induced apoptosis through a mitochondria-dependent pathway. A, Mitochondrial membrane morphology of HL- 60 cells treated with 7. HL-60 cells were stained with MitoCapture™ reagent after treatment with either 0.21 μM of 7 or 33 μM of cisplatin for 6 h and observed under a fluorescence microscope. B, Release of cytochrome c from mitochondria of HL-60 cells treated with 7. HL-60 cells were treated with either 0.21 μM of 7 or 33 μM of cisplatin for 8 h, and the release of cytochrome c into the cytoplasm was evaluated by Western blot analysis.

Fig. 3 in Alkaloid and iridoid glucosides from Palicourea luxurians (Rubiaceae: Palicoureeae) indicate tryptamine- and tryptophan-iridoid alkaloid formation apart the strictosidine pathway

Fig. 3. Most relevant correlations of isoalstrostine A (1) and dehydrorudgeifoline (2) indicated by correlation peaks in COSY (green), HMBC (red) and ROESY (blue), which are used for structure elucidation. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 2 in Alkaloid and iridoid glucosides from Palicourea luxurians (Rubiaceae: Palicoureeae) indicate tryptamine- and tryptophan-iridoid alkaloid formation apart the strictosidine pathway

Fig. 2. Structures of iridoids isolated from leaves and stem bark of Palicourea luxurians are asperuloside (6), secoxyloganin (7), demethylsecologanol (8), secologanic acid (9) and sweroside (10). Furthermore, the secologanin isolation artifacts (E)-aldosecologanin (11), secologanin dimethyl acetal (12), secologanin di-n-butyl acetal (13) as well as both diastereomeres of secologanin n-butyl methyl acetal (14a/14b) are shown. Compounds 6 and 7 have been isolated from the stem bark, all other compounds have been isolated from the leaves.

Fig. 1 in Alkaloid and iridoid glucosides from Palicourea luxurians (Rubiaceae: Palicoureeae) indicate tryptamine- and tryptophan-iridoid alkaloid formation apart the strictosidine pathway

Fig. 1. Structures of the isolated tryptamine-iridoid alkaloids and the tryptophan-iridoid alkaloid from leaves of Palicourea luxurians: Isoalstrostine A (1), dehydrorudgeifoline (2), alstrostine A (3), javaniside (4) and 5α-carboxystrictosidine (5). The glucoside moieties are shown as D-glycosides for compounds 1 to 5 as well as for all other isolated glycosides 6 to 14a/14b (Fig. 2), but have not been proven in all cases due to low available amounts.

Fig. 6 in Alkaloid and iridoid glucosides from Palicourea luxurians (Rubiaceae: Palicoureeae) indicate tryptamine- and tryptophan-iridoid alkaloid formation apart the strictosidine pathway

Fig. 6. Possible pathways, leading to alstrostine-type as well as to isoalstrostine-type alkaloid structures. In the first step (a) an alline-like intermediate with two secondary amine functions is generated by oxidation and cyclization of tryptamine (Nakagawa and Hino, 1977). Subsequent in step (b), two secologanin molecules react with both secondary amine functions gaining two enamine moieties. In the following steps (c1/c2) and (d1/d2), protonation of one of the two enamine functions leads to the formation of a sixmembered ring with an iminium ion moiety. Depending on the location of the initial protonation in step (d1/d2), the six-membered ring carries its substituents either in position 3′ (–CH2–R) and 14 (-R), or in position 3 (–CH2–R) and 14′ (-R), respectively. The final deprotonation (e1/e2) leads in both cases to the formation of the enamine and thus results in the alstrostine-type or the isoalstrostine-type structure, respectively. Structure of residue "R" is shown in the box. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)