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Fig. 3 in Diterpenoids from Gutierrezia sarothrae and G. microcephala: Chemical diversity, chemophenetics and implications to toxicity in grazing livestock

Fig. 3. Chemical structures of isolated diterpenoids. Previously unreported compounds are marked with an asterisk. Key NOESY correlations depicted with double arrow.

Fig. 2 in Diterpenoids from Gutierrezia sarothrae and G. microcephala: Chemical diversity, chemophenetics and implications to toxicity in grazing livestock

Fig. 2. Representative GC-MS chromatograms of the 8 different chemotypes with GC retention times (min) and corresponding chemical structure number (bold number). *This is not the TMSi derivative but the free alcohol of 15. ** Compound 5 and 17 are susceptible to injection port conditions and were only observed by injection of pure compound.

Fig. 1 in Diterpenoids from Gutierrezia sarothrae and G. microcephala: Chemical diversity, chemophenetics and implications to toxicity in grazing livestock

Fig. 1. Graphical map of snakeweed collection sites marked as to species identified (A) and assigned chemotypes (B) from the states of Utah, Wyoming, Colorado, Oklahoma, Texas and New Mexico. Chemotype 0 ¼ unidentified.

Fig. 3 in Cytotoxic diterpenoids from the leaves and stem bark of Croton haumanianus (Euphorbiaceae)

Fig. 3. Calculated (ent- and normal series) and experimental ECD spectra for compounds 18, 20, 22 and 25.

Fig. 2 in Cytotoxic diterpenoids from the leaves and stem bark of Croton haumanianus (Euphorbiaceae)

Fig. 2. Key NOESY correlations of compounds 4, 9, 11, 14 (R ¼ (CH2)14CH3, in green), 18 and 19. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 2. 1H–1H in Diterpenoids caryopterisoids D - Q and iridoid glucoside derivatives caryopterisides F - H from Caryopteris glutinosa

Fig. 2. 1H–1H COSY and key HMBC correlations (A), selected NOESY correlations and nOe differences (B), and ECD spectra (C) of compounds 1 and 2. D, ORTEP drawing of 1 from X-ray crystallographic data.

Fig. 1 in Diterpenoids caryopterisoids D - Q and iridoid glucoside derivatives caryopterisides F - H from Caryopteris glutinosa

Fig. 1. Chemical structures of caryopterisoids D - Q (1 – 14) and caryopterisides F H (15 - 17) from Caryopteris glutinosa.

Fig. 4 in Diterpenoids caryopterisoids D - Q and iridoid glucoside derivatives caryopterisides F - H from Caryopteris glutinosa

Fig. 4. Cell-based estrogen biosynthesis assays for the isolated compounds (A), WB of caryopterisoid K (8) (B) and its quantitative results (C), qRT-PCR (D), and molecular docking (E). DMSO, control; FSK, 10 μM forskolin, positive control for the increase of estrogen E2; LET, 10 nM letrozole, positive control for the decrease of estrogen E2; CREB, cAMP-response element binding protein, a key protein in the upstream of the signaling pathway of estrogen biosynthesis; pCREB, phosphorylated CREB; Form, 50 μM formestane, positive control for the expression of aromatase; GAPDH, glyceraldehyde-3-phosphate dehydrogenase, reference gene; KI, inhibition constant. *, p <0.05; **, p <0.01; ***, p <0.001; compared with the control (n = 3).

Fig. 1 in Natural variation of diterpenoid phytoalexins in cultivated and wild rice species

Fig. 1. Accumulation of momilactones A and B in cultivars from the WRC and wild rice species after UV irradiation. (A) Momilactone A amounts in WRC cultivars. (B) Momilactone B amounts in WRC cultivars. (C) Correlation between the amounts of momilactones A and B. R2: decision coefficient. (D) Amounts of momilactones A and B in wild rice species. Or-I, Or-II, and Or-III indicate clades of O. rufipogon. O. gla: O. glaberrima; O. bar: O. barthii; O. glu: O. glumaepatula; O. mer: O. meridionalis; O. pun: O. punctata; O. bra: O. brachyantha. Values are means ± SD of three biological replicates. n.d.: not detected.

Fig. 2 in Natural variation of diterpenoid phytoalexins in cultivated and wild rice species

Fig. 2. Accumulation of phytocassanes A and D in cultivars from the WRC and wild rice species after UV irradiation. (A) Phytocassane A amounts in WRC cultivars. (B) Phytocassane D amounts in WRC cultivars. (C) Correlation between amounts of phytocassanes A and D. R 2: decision coefficient. (D) Amounts of phytocassanes A and D in wild rice species. Or-I, Or-II, and Or-III indicate clades of O. rufipogon. O. gla: O. glaberrima; O. bar: O. barthii; O. glu: O. glumaepatula; O. mer: O. meridionalis; O. pun: O. punctata; O. bra: O. brachyantha. Values are means ± SD of three biological replicates. n.d.: not detected.

Fig. 5 in Natural variation of diterpenoid phytoalexins in cultivated and wild rice species

Fig. 5. Analysis of the chemical structure of 2. (A) COSY (bold lines) and HMBC (black arrows from protons to carbon atoms) correlations of 2. (B) Chemical structure of phytocassane A. (C) NOESY correlations on the three-dimensional chemical structure of 2. (D) Chemical structure of 2.

Fig. 7 in Natural variation of diterpenoid phytoalexins in cultivated and wild rice species

Fig. 7. Accumulation of oryzalactone and phytocassane G in the WRC cultivars and wild rice species after UV irradiation. (A) Oryzalactone amounts in WRC cultivars. (B) Phytocassane G amounts in WRC cultivars. (C) Oryzalactone and phytocassane G amounts in wild rice species.Or-I, Or-II, and Or-III indicate clades of O. rufipogon. O. gla: O. glaberrima; O. bar: O. barthii; O. glu: O. glumaepatula; O. mer: O. meridionalis; O. pun: O. punctata; O. bra: O. brachyantha. Values are means ± SD of three biological replicates. n.d.: not detected.

Fig. 6 in Natural variation of diterpenoid phytoalexins in cultivated and wild rice species

Fig. 6. Accumulation of oryzalactone and phytocassane G in response to rice blast infection and the antifungal activities of these compounds against rice blast. (A) Accumulation of oryzalactone in 'Jaguary' leaves in response to rice blast infection. (B) Accumulation of phytocassane G in 'Basilanon' leaves in response to rice blast infection.Amounts of 1 and 2 were determined 72 h after the start of treatment. n.d.: not detected. Values are means ± SD of three biological replicates. Asterisks indicate significant differences (*p <0.05, **p <0.01; Dunnett's test). (C) Effect of compounds on the germination of P. oryzae 12 h after incubation. (D) Effect of compounds on conidial germ tube elongation, which was measured 12 h after treatment.Values and error bars are means ± SD (n = 3). Different letters indicate significant differences (p <0.05; Tukey–Kramer method).

Fig. 3 in Natural variation of diterpenoid phytoalexins in cultivated and wild rice species

Fig. 3. Multiple reaction monitoring (MRM) chromatogram in momilactone A analysis. (A) Analysis of authentic momilactone A; retention time of 7.2 min. (B) Compound 1 was detected in the extract from 'Jaguary' with a retention time of 7.7 min. (C) Compound 2 was detected in the extract from 'Basilanon' with a retention time of 7.4 min.

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Fig. 5 in Abietane diterpenoids from Dracocephalum moldavica L. and their anti-inflammatory activities in vitro

Fig. 5. Inhibition rates of compounds 1–11 on TNF-α, IL-1β and NO production in LPS–stimulated RAW 264.7 cells at the concentration of 10 μM * The concentration of the compound was 30 μM.

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Fig. 6 in Eupholides A H, abietane diterpenoids from the roots of Euphorbia fischeriana, and their bioactivities

Fig. 6. The inhibitory effects of diterpenoids 1–15 on HCE 2 (a). The inhibitory effects of diterpenoids 7 (b), 10 (c), and 12 (d) on HCE 2.

Fig. 10 in Diterpenoids from Euphorbia royleana reverse P-glycoprotein-mediated multidrug resistance in cancer cells

Fig. 10. Binding pose of 15 with human Pgp. The P-gp model was generated based on the PDB structure of human P-gp (Code: 6QEX) and was portrayed as a cartoon (light green). Residues involved in the interaction were colored yellow, while the surfaces of the hydrophobic pocket packing with 15 were colored light brown red. The hydrogen bonds and hydrophobic forces were shown as red dashed lines and yellow dashed lines, respectively. The structural figures were drawn in Accelrys Discovery Studio 2016. (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)

Fig. 9 in Diterpenoids from Euphorbia royleana reverse P-glycoprotein-mediated multidrug resistance in cancer cells

Fig. 9. (A) Inhibitory effects of 15 on the accumulation of rhodamin-123 (Rho-123) in HepG2/DOX. (B) Inhibitory effects of 15 on the efflux of Rho-123 in HepG2/ DOX. Scale bar = 200 μm.

Fig. 7 in Diterpenoids from Euphorbia royleana reverse P-glycoprotein-mediated multidrug resistance in cancer cells

Fig. 7. Mediated multidrug resistance (MDR)-reversing effects of the compounds on doxorubicin (DOX)-resistant human hepatocellular carcinoma cell line (HepG2/ DOX).

Fig. 6 in Diterpenoids from Euphorbia royleana reverse P-glycoprotein-mediated multidrug resistance in cancer cells

Fig. 6. Experimental ECD spectrum of 3 (red line) and calculated ECD spectra (200–400 nm) of (3S,4S,5R,8S,10S,11R,13R,14R,15R)-3a (black line) and (3R,4R,5S,8R,10R,11S,13S,14S,15S)-3b (blue line). (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)