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Fig. 3 in Polyoxygenated germacranes from Daucus carota and their antimalarial transmission blocking activity

Fig. 3. In vitro P. berghei ookinete development assays with metabolites from D. carota assessed at concentrations of 0.001, 0.01, 0.1, 1 and 50 mM. Values were calculated with respect to negative control (DMSO). * = significant inhibition (p value <0.05 paired t-test). Error bars indicate SEM within biological triplicates.

Fig. 4 in Tirucallane triterpenoids from the mastic (Pistacia lentiscus) and their anti-inflammatory and cytotoxic activities

Fig. 4. (a) Key 1H–1H COSY (▬) and selected HMBC correlations (H→C) of 12; (b) Key NOESY correlations of 12.

Fig. 2 in Tirucallane triterpenoids from the mastic (Pistacia lentiscus) and their anti-inflammatory and cytotoxic activities

Fig. 2. (a) Key 1H–1H COSY (▬) and selected HMBC correlations (H→C) of 1; (b) Key NOESY correlations of 1.

Fig. 2 in (þ/¡)-Dievodialetins A¡G: Seven pairs of enantiomeric coumarin dimers with anti-acetylcholinesterase activity from the roots of Evodia lepta Merr.

Fig. 2. (A) Key 1H–1H COSY (red bold lines) and HMBC (blue arrows) correlations of 1. (B) X-ray ORTEP schematic of 1. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 5. Compounds 1–9 in (þ/¡)-Dievodialetins A¡G: Seven pairs of enantiomeric coumarin dimers with anti-acetylcholinesterase activity from the roots of Evodia lepta Merr.

Fig. 5. Compounds 1–9 ameliorate oxidative stress and neuroinflammation in scopolamine-treated SH-SY5Y cells.

Fig. 5 in Tirucallane triterpenoids from the mastic (Pistacia lentiscus) and their anti-inflammatory and cytotoxic activities

Fig. 5. Cytotoxic effects of compounds 1–16 on RAW 264.7 cell viability at concentration of 60 μM, Dexamethasone was used as a positive control. Cell viability was measured by the CKK-8 assay. Data are expressed as mean ± SD, n = 3, *p <0.05, **p <0.01, ***p <0.001 vs control group.

Fig. 7 in Lichen-associated bacteria transform antibacterial usnic acid to products of lower antibiotic activity

Fig. 7. Molecular networking results from GNPS visualized with Cytoscape. Inset: cluster of UA and derivatives with close fragmentation pathway (m/z 357.12: compound K, m/z 389.104: compound L) and self-loop of compound H (at m/z 386.139).

Fig. 4 in Lichen-associated bacteria transform antibacterial usnic acid to products of lower antibiotic activity

Fig. 4. HPLC chromatograms of S. cyaneofuscatus cultures with or without UA: A) At the beginning of the stationary phase of bacterial growth; B) After 7 days of stationary phase. Circled in blue: compounds inhibited in the presence of UA, circled in orange: compounds more concentrated in the presence of UA, circled in red: UA. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 1 in Lichen-associated bacteria transform antibacterial usnic acid to products of lower antibiotic activity

Fig. 1. Monitoring of the bacterial growth over 15 days (D0 to D15) by measuring optical density (log OD (optical density), gray curve) and cell viability (%) using MTT assay (blue curve) compared to untreated culture (orange curve). A) Nocardia sp., B) S. cyaneofuscatus, C) M. ruber. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 3 in Lichen-associated bacteria transform antibacterial usnic acid to products of lower antibiotic activity

Fig. 3. HPLC chromatograms of Nocardia sp. culture with or without UA. A) At the beginning of the stationary phase of the bacterial growth; B) After 7 days of stationary phase. Compounds circled in red appear only in the culture with UA. (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 Lichen-associated bacteria transform antibacterial usnic acid to products of lower antibiotic activity

Fig. 2. HPLC chromatograms of M. ruber cultures with or without UA. A) At the beginning of the stationary phase of bacterial growth; B) After 7 days of stationary phase. Compounds circled in red appear only in the culture with UA. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 5 in Lichen-associated bacteria transform antibacterial usnic acid to products of lower antibiotic activity

Fig. 5. Comparison of HPLC chromatograms of B. weihenstephanensis extracts with UA at 0.01 mg/mL after 1 day of culture (blue), 9 days of culture (black) and without UA after 9 days of culture (red). (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 8 in Lichen-associated bacteria transform antibacterial usnic acid to products of lower antibiotic activity

Fig. 8. Fragmentation patterns in negative mode of A) compound H and B) UA; common fragments are highlighted in orange. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 6. S491A in Probing of the plasticity of the active site in pinene synthase elucidates its potential evolutionary mechanism

Fig. 6. S491A mutation increases the rigidity of the active pocket when it binds the pinyl cation. RMSD values of the active site residues between WT and S491A in complex with the pinyl cation (a), terpinyl cation (b) and thujyl cation (c) are compared.

Fig. 5 in Probing of the plasticity of the active site in pinene synthase elucidates its potential evolutionary mechanism

Fig. 5. The effect of the S491A mutation. Chromatograms in a, b and c show the GC-MS analysis of terpene production for S491A, F482A/S491A, and F482I/S491A, respectively. The x-axis is the retention time and the y-axis is the relative abundance of each species. The numbers in each peak correspond to α-pinene (1), sabinene (2) and limonene (3). d shows the overall activity and the percentage of sabinene within total products produced by F482A, F482A/S491A, F482I and F482I/S491A. The asterisk indicates P <0.05.

Fig. 4 in Probing of the plasticity of the active site in pinene synthase elucidates its potential evolutionary mechanism

Fig. 4. Conformational differences in the pinyl cation in WT and F482Y as demonstrated by molecular dynamics simulation. The structures of WT and F482Y are superimposed. Results after 0, 1 and 2 ns of simulation are shown in a, d and c, respectively. Carbon in WT is colored in yellow and carbon in F482Y is colored in green. Oxygen is colored in red. Nitrogen is colored in blue. (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)

Fig. 2 in Probing of the plasticity of the active site in pinene synthase elucidates its potential evolutionary mechanism

Fig. 2. Converting pinene synthase to sabinene synthase by mutations on 482 position. Chromatograms in a, b, c, d and e show the GC-MS analysis of terpene products for WT, F482A, F482I, F482V and F482T, respectively. The x-axis is the retention time and the y-axis is the relative abundance of each species. The numbers in each peak correspond to α-pinene (1), sabinene (2) and limonene (3).

Fig. 3 in Probing of the plasticity of the active site in pinene synthase elucidates its potential evolutionary mechanism

Fig. 3. Hybrid quadrupole-orbitrap GC-MS/MS. a shows the chromatogram of terpene products of F482L. The elution peak corresponding to sabinene is labeled. The mass spectrum of the product eluted at 9.29 min from a is shown in b. The mass spectrum of the standard sabinene is shown in c.

Fig. 1. a in Probing of the plasticity of the active site in pinene synthase elucidates its potential evolutionary mechanism

Fig. 1. a, The proposed reaction mechanism for the synthesis of limonene, pinene and sabinene. b, The structural model of pinene synthase docked with the terpinyl (left), pinyl (middle) and thujyl (right) cations. Carbocations are colored in magenta (terpinyl), wheat (pinyl) and cyan (thujyl). Other atoms are colored according to their types (red: oxygen; yellow: carbon; blue: nitrogen; orange: phosphorus; green: magnesium). (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)

Fig. 7 in Probing of the plasticity of the active site in pinene synthase elucidates its potential evolutionary mechanism

Fig. 7. The RMSD profiles of the region with high (RMSD H) and low (RMSD L) mobility from the simulation of WT (a), S491A (b) and F482/S491A (c) in complex with the pinyl cation.