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Fig. 7 in P450 variations bifurcate the early terpene indole alkaloid pathway in Catharanthus roseus and Camptotheca acuminata

Fig. 7. Molecular models of Catharanthus CYP72A1 and Camptotheca CYP72A564 and CYP72A565. (A) Backbone overlays of Catharanthus CYP72A1 and Camptotheca CYP72A564 and CYP72A565 models are shown with the alpha-carbon RMSD amongst CYP72A1, CYP72A564 and CYP72A565 depicted from green (0.0 Å) to yellow (3.0 Å) to 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 loganin (aqua) docked in Catharanthus CYP72A1 (blue) and loganic acid (gray) docked in Camptotheca CYP72A564 (orange). (E) Identical versus (F) different side chain residues predicted within 4.5 Å of loganin (aqua) docked in Catharanthus CYP72A1 (blue) and loganic acid (gray) docked in Camptotheca CYP72A565 (rose).

Fig. 5 in P450 variations bifurcate the early terpene indole alkaloid pathway in Catharanthus roseus and Camptotheca acuminata

Fig. 5. Area of loganic acid, loganin and products from in vitro reconstitution assays conducted with full-length Camptotheca His6-tagged CPR1. Integrated areas from LC-MS analyses of purified His6-tagged CYP72A proteins reconstituted with full-length His6-tagged Caa CPR1 are shown for no NADPH (gray) and plus NADPH (gray slashed) reactions.

Fig. 2. CYP72A in P450 variations bifurcate the early terpene indole alkaloid pathway in Catharanthus roseus and Camptotheca acuminata

Fig. 2. CYP72A multiple sequence alignment. Signal anchor domain fusion of CYP72A565 into CYP72A564 is underlined; SRS regions are underlined in bold; predicted substrate contacts within 4.5 Å of loganic acid/loganin are gray-filled.

Fig. 1 in P450 variations bifurcate the early terpene indole alkaloid pathway in Catharanthus roseus and Camptotheca acuminata

Fig. 1. Proposed divergence of the TIA pathway between Camptotheca and Catharanthus. After 7-deoxyloganic acid hydroxylase (7DLH) converts 7-deoxyloganic acid to loganic acid, the pathways in these two species diverge. The Catharanthus pathway uses loganic acid methyltransferase (LAMT) to convert loganic acid into loganin and secologanin synthase (SLS) to convert loganin into secologanin. The Camptotheca pathway bypasses LAMT and uses secologanic acid synthase (SLAS) to metabolize loganic acid directly to secologanic acid.

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 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. 4 in Indole-based alkaloids from Ophiocordyceps xuefengensis

Fig. 4. Experimental CD spectrum (black lines) and calculated ECD spectra (red, green, and other lines) of 1–7. (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 Indole-based alkaloids from Ophiocordyceps xuefengensis

Fig. 6. Effects of 5 and 6 to promote apoptosis of A549 cells. ***P <0.01 compared with the control group.

Fig. 5 in Indole-based alkaloids from Ophiocordyceps xuefengensis

Fig. 5. Photomicrographs of A549 cells stained with DAPI dye. The enlarge ratio of all images is 200 ×.

Fig. 5 in Catecholic alkaloid sulfonates and aromatic nitro compounds from Portulaca oleracea and screening of their anti-inflammatory and anti-microbial activities

Fig. 5. Possible biosynthetic pathway for the nitro derivatives, catecholic alkaloids and their sulfonates from P. oleracea (DDC: dopa decarboxylase; RNS: reactive nitrogen species; TH: tyrosine hydroxylase).

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.

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.

Fig. 6 in Catecholic alkaloid sulfonates and aromatic nitro compounds from Portulaca oleracea and screening of their anti-inflammatory and anti-microbial activities

Fig. 6. Dose-dependent inhibition of nitro derivative 12 against LPS-induced NO production in RAW 264.7 macrophage cells (n = 3) (****p <0.0001, versus vehicle control, ####p <0.0001, versus LPS-treated model, 3,4-dihydroxy-benzohydroxamic acid (Didox) was used as the positive control with IC value of 70 μM).

Fig. 4 in Catecholic alkaloid sulfonates and aromatic nitro compounds from Portulaca oleracea and screening of their anti-inflammatory and anti-microbial activities

Fig. 4. Calculated and experiment ECD of compounds 4, 10–11, 15–17 and their possible stereostructures

Fig. 6. Linear correlation plots between the experimental and calculated 13C in Structurally diverse alkaloids with nine frameworks from Zephyranthes candida and their acetylcholinesterase inhibitory and anti-inflammatory activities

Fig. 6. Linear correlation plots between the experimental and calculated 13C NMR data for two isomers of 2.

Fig. 4 in Structurally diverse alkaloids with nine frameworks from Zephyranthes candida and their acetylcholinesterase inhibitory and anti-inflammatory activities

Fig. 4. Experimental and calculated ECD spectra of zephyranines A (1) and B (2) and their enantiomers.

Fig. 3. Linear correlation plots between the experimental and calculated 13C in Structurally diverse alkaloids with nine frameworks from Zephyranthes candida and their acetylcholinesterase inhibitory and anti-inflammatory activities

Fig. 3. Linear correlation plots between the experimental and calculated 13C NMR data for four isomers of 1.

Fig. 10 in Structurally diverse alkaloids with nine frameworks from Zephyranthes candida and their acetylcholinesterase inhibitory and anti-inflammatory activities

Fig. 10. The binding modes of 1 (A), 7 (B), 8 (C), and galanthamine (D) with AChE (PDB ID: 4M0E). The hydrogen bonds are indicated by red dashed lines. (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)