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Fig. 1 in Protochlorophylls in Cucurbitaceae - Distribution, biosynthesis and phylogeny

Fig. 1. (a) Two-dimensional HPLC chromatogram of protochlorophylls extracted from the seed coat of pumpkin (Cucurbita pepo) seeds and (b) the corresponding one-dimensional chromatogram using absorption detection at 435 nm. Analysis was performed using C30 YMC column, methanol/ethyl acetate (34/16) as eluent and 1.5 ml/min flow.

Fig. 8 in Rosmarinic acid and hesperidin regulate gas exchange, chlorophyll fluorescence, antioxidant system and the fatty acid biosynthesis-related gene expression in Arabidopsis thaliana under heat stress

Fig. 8. The changes of the relative expression of WRI1 (A), BCCP2 (B), FAD2 (C), FAD3 (D) genes encoding after rosmarinic acid (RA, 100 μM) and/or hesperidin (HP, 100 μM) with/without heat stress (38 ◦C) in A. thaliana leaves. Multivariate data analyses of gene expression analysis under investigation.

Fig. 5 in Rosmarinic acid and hesperidin regulate gas exchange, chlorophyll fluorescence, antioxidant system and the fatty acid biosynthesis-related gene expression in Arabidopsis thaliana under heat stress

Fig. 5. The changes of the relative band intensity of different types of glutathione S-transferase activity isoenzymes (GST, A) and GST activity (B), and glutathione peroxidase activity (GPX, C) after rosmarinic acid (RA, 100 μM) and/or hesperidin (HP, 100 μM) with/without heat stress (38 ◦C) in A. thaliana leaves.

Fig. 1 in Rosmarinic acid and hesperidin regulate gas exchange, chlorophyll fluorescence, antioxidant system and the fatty acid biosynthesis-related gene expression in Arabidopsis thaliana under heat stress

Fig. 1. The average absorption per active reaction center (ABS/RC), the electron transport flux per active reaction center (ETo/RC), the flux of trapped exciton per active reaction center (TRo/RC), and the energy flow on the acceptor side of PSI ((Ro), The number of QA-reducing reaction centers per PSII antenna chlorophyll ((ΦPo/(1-ΦPo)), the efficiency with which a trapped exciton transfers an electron to the photosynthetic electron transfer chain ((ΨEo/(1-ΨEo)), the number of QA- reducing reaction centers per PSII antenna chlorophyll (γRC/(1-γRC)), the ratio of total dissipation to the number of active reaction centers (DIo/RC). The relative variable fluorescence intensity at J (VJ) and I step (VI), the performance index based on light absorption (PIABS), and the performance index (potential) for energy conservation from exciton to PSI and acceptor reduction (PItotal) were determined in A. thaliana leaves following treatment with rosmarinic acid (RA, 100 μM) and/or hesperidin (HP, 100 μM) with/without heat stress (38 ◦ C).

Fig. 7 in Rosmarinic acid and hesperidin regulate gas exchange, chlorophyll fluorescence, antioxidant system and the fatty acid biosynthesis-related gene expression in Arabidopsis thaliana under heat stress

Fig. 7. The changes of monodehydroascorbate reductase activity (MDHAR, A), dehydroascorbate reductase activity (DHAR, B), ascorbate content (AsA, C), dehydroascorbate content (DHA, D), glutathione content (GSH, E), oxidized glutathione content (GSSG, F), AsA/DHA (G), GSH/GSSG (H) and GSH redox state (I) after rosmarinic acid (RA, 100 μM) and/or hesperidin (HP, 100 μM) with/without heat stress (38 ◦C) in A. thaliana leaves.

Fig. 4 in Rosmarinic acid and hesperidin regulate gas exchange, chlorophyll fluorescence, antioxidant system and the fatty acid biosynthesis-related gene expression in Arabidopsis thaliana under heat stress

Fig. 4. The changes of the relative band intensity of different types of peroxidase isoenzymes (POX, A) and POX activity (B), relative band intensity of different types of NADPH oxidase isoenzymes (NOX, C) and NOX activity (D) after rosmarinic acid (RA, 100 μM) and/or hesperidin (HP, 100 μM) with/without heat stress (38 ◦C) in A. thaliana leaves.

Fig. 3 in Rosmarinic acid and hesperidin regulate gas exchange, chlorophyll fluorescence, antioxidant system and the fatty acid biosynthesis-related gene expression in Arabidopsis thaliana under heat stress

Fig. 3. The changes of the relative band intensity of different types of superoxide dismutase isoenzymes (SOD, A) and SOD activity (B), the relative band intensity of different types of catalase isoenzymes (CAT, C) and CAT activity (D) after rosmarinic acid (RA, 100 μM) and/or hesperidin (HP, 100 μM) with/without heat stress (38 ◦C) in A. thaliana leaves.

Fig. 2 in Rosmarinic acid and hesperidin regulate gas exchange, chlorophyll fluorescence, antioxidant system and the fatty acid biosynthesis-related gene expression in Arabidopsis thaliana under heat stress

Fig. 2. The changes of hydrogen peroxide content (H O, A), lipid peroxidation (TBARS content, B), histochemical staining for O • accumulation (C), histochemical 2 2 2 staining for H2O2 determination (D), histochemical staining for plasma membrane integrity (E) and histochemical staining for lipid peroxidation (F) after rosmarinic acid (RA, 100 μM) and/or hesperidin (HP, 100 μM) with/without heat stress (38 ◦C) in A. thaliana leaves.

Fig. 6 in Rosmarinic acid and hesperidin regulate gas exchange, chlorophyll fluorescence, antioxidant system and the fatty acid biosynthesis-related gene expression in Arabidopsis thaliana under heat stress

Fig. 6. The changes of the relative band intensity of different types of ascorbate glutathione isoenzymes (APX, A) and APX activity (B), and glutathione reductase activity (GR, C) after rosmarinic acid (RA, 100 μM) and/or hesperidin (HP, 100 μM) with/without heat stress (38 ◦C) in A. thaliana leaves.

Fig. 16 in Stilbenes: Source plants, chemistry, biosynthesis, pharmacology, application and problems related to their clinical Application-A comprehensive review

Fig. 16. Biological activities of stilbenes and their action mechanisms: The major biological activities of stilbenes are anticancer (through inhibiting β-hexosaminidase, DNA topoisomerase, expression of cylin B1 & D1, and NOR 1 activity); anti-inflammatory (through inhibition of expression of proinflammatory cytokines such as Tumor necrosis factor-alpha (TNF-α) and Interleukin-1 (IL-1)); regulation of Nrf2/HO-1 and NF-kB/ TGF-β pathway as well as inhibiting direct binding between siCAM-1 and LFA-1); antimicrobial (by damaging microbial cell wall and cell membrane damage, condensation of cytoplasm, perturbation of membrane potential, interacting with the conserved ubiquitin-specific protease residues of PLpro), and down-regulation of ergosterol biosynthesis and Camp/Ras pathway; antidiabetic (through inhibiting TNF-α, α-glucosidase, intestinal sucrose transfer, elevation of blood glucose as well as inducing/ increasing PPAR gamma 2 and GLUT4); antioxidant (through inhibiting lipid peroxidation, NO production, NOS activity, and increasing SOD activity); and neuroprotective (by inhibiting NOS activity, NO production, and HO-1 expression) activities.

Fig. 12 in Stilbenes: Source plants, chemistry, biosynthesis, pharmacology, application and problems related to their clinical Application-A comprehensive review

Fig. 12. Biosynthesis of stilbenes in microbes: For high production of stilbenes in microbes such as E. coli, the metabolic pathway of malonyl-CoA, the major and common extender substrate during conversion of coumaroyl, cinnamyl, and caffeoyl-CoAs to their respective monomeric stilbenes, is mainly manipulated. Enzymes of side pathways leading to the synthesis of fatty acids and acetate from acetyl-CoA, the direct precursor of malonyl-CoA, are inhibited, or their encoding enzymes are down-regulated or knocked out. For more efficient and high production of the stilbenes, there is also host, pathway, and enzyme engineering in the pathway of converting coumaroyl, cinnamyl, and caffeoyl- CoAs to monomeric stilbenes using STS.

Fig. 15 in Stilbenes: Source plants, chemistry, biosynthesis, pharmacology, application and problems related to their clinical Application-A comprehensive review

Fig. 15. Chemical synthesis of resveratrol derivatives: The derivatives 3,4′,5-trimethoxy-cis-stilbene (b), 3,4′,5-trimethoxy-trans-stilbene (c), 3,4,4′,5-tetramethoxytrans-stilbene (DMU-212, d), 2,3′,4,4′,5′-pentamethoxy-trans-stilbene (PMS, e), and 2′,3,4′,5-tetramethoxy (TMS; f) are synthesized by methoxylation of the central resveratrol (a), while the synthetic analogs 3′,4′,3,5-tetrahydroxy-trans-stilbene (piceatannol); (g) and 3,3′,4,4′,5,5′-hexahydroxy-trans-stilbene (h) are produced by hydroxylation of (a). The result of fluorination and esterification is 3,4-difluoro-4′-acetoxy-trans-stilbene (i), while bromination and methoxylation give 3,4,5-trimethoxy-4′-bromostilbene (j). The analogous 2,3-thiazolidin-4-one RSV derivatives (l and k) are synthesized through replacement of the olefinic group of (a) by heterocyclic compounds.

Fig. 1 in Stilbenes: Source plants, chemistry, biosynthesis, pharmacology, application and problems related to their clinical Application-A comprehensive review

Fig. 1. Phylogenetic tree of known stilbene-producing plants: Each family was marked with a different color in the figure. The circle-marked species are capable of producing stilbenes. Kappaphycus striatum (JN897024.1) and Silvetia siliquosa (JF718409.1) are included as out-groups. The phylogenetic tree was constructed using the ITS2 (ribosomal internal transcribed spacer 2) genus sequence. ITS2 sequences were obtained from NCBI (National Center for Biotechnology Information) (https://www.ncbi.nlm.nih.gov/). Some unannotated sequences were identified and delimited based on Hidden Markov models (HMMs), which was performed through the online website-ITS2 Database (http://its2.bioapps.biozentrum.uni-wuerzburg.de/). The MUSCLE program in MEGA6.0 software was used to perform multiple sequence alignments, and the neighbor-joining (NJ) method was used to construct phylogenetic trees with 1000 bootstrap replicates. The kimura-2- parameter substitution model was also employed, and the confidence interval was 95%. The evolutionary tree is visualized and beautified by the online software iTOL (https://itol.embl.de/). (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)

Fig. 11 in Stilbenes: Source plants, chemistry, biosynthesis, pharmacology, application and problems related to their clinical Application-A comprehensive review

Fig. 11. Biosynthesis of stilbenes in plant suspension cell culture: plants with a high stilbene content will be cut to a specific size. These will be incubated in agarized medium (Murashige and Skoog (MS) medium or CHU (N6) medium or Gamborg's B5 medium (B5)) with supplements such as 6-benzyl amino purine (6-BA), kinetin (KT), Naphthalene acetic acid (NAA), and 2,4-Dichlorophenoxyacetic acid (2,4-D). After some specific days, friable cells will be produced in the medium, and these cells are then transferred into a new fresh medium with the specific supplements. Finally, elicitors such as 12-oxo-phytodienoic acid (OPDA), cornatine (COR), jasmonic acid (JA), methyl jasmonate (MeJA), salicylic acid (SA), ethylene (ET), abscisic acid (ABA), and reactive oxygen species (ROS) will be added for high production of stilbenes.

Fig. 14 in Stilbenes: Source plants, chemistry, biosynthesis, pharmacology, application and problems related to their clinical Application-A comprehensive review

Fig. 14. Synthetic derivatives of CA-4 (1): These are produced by replacement, substitution, and modification at both the cis-olefinic bond and the aromatic rings of 1. N-acyl hydrazone CA-4 (4), azo CA-4 (3), 1, 3, 4, oxadiazole CA-4 (9), benzoxazole CA-4 (8) which are produced by replacement and modifications at the olefinic group. Through modifications to the cis-olefinic bond and aromatic rings of CA-4, analogs such as 2 and 7 (benzothiazole derivatives of CA-4 with fluorine), 5 and 6 (imidazole and indole derivatives of CA-4) are also synthesized.

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Fig. 4 in Structures of ganorbifates C-I, seven previously undescribed lanostanoids from the mushroom Ganoderma orbiforme, and insights of computed biosynthesis with DFT

Fig. 4. NOE correlations and comparison between experimental and calculated ECD spectra for compound 1.

Fig. 7 in Genome-wide identification and characterization of genes involved in melatonin biosynthesis in Morus notabilis (wild mulberry)

Fig. 7. Biosynthetic pathway of melatonin. The black arrows identify the pathway in herbaceous and woody plants while the red arrows identify the pathway in woody plants. The enzymes of the respective steps are as follows: TDC; T5H; SNAT; ASMT; and COMT. (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)

Fig. 5 in Genome-wide identification and characterization of genes involved in melatonin biosynthesis in Morus notabilis (wild mulberry)

Fig. 5. Purification and enzymatic analyses of recombinant His-tagged MnASMT12. A: Purification of recombinant His-tagged MnASMT12 (lane1: Protein Marker; lane2: pCold TF (+IPTG); lane3: recombinant protein (-IPTG); lane4: recombinant protein (+IPTG); lane5: purified protein). B: Mass spectrum of compounds detected using UPLC-MS/MS. a: melatonin standard; b: Chromatogram of N-acetylserotonin catalyzed by MnASMT12. C: Determination of Km and Vmax of MnASMT12 for Nacetylserotonin. MnASMT12 (1.0 μg) was co-incubated with different concentrations of N-acetylserotonin for 20 min at 37 ◦C. D: Mass spectrum of compounds detected using UPLC-MS/MS. a: 5-methoxytryptamine standard; b: Chromatogram of serotonin catalyzed by MnASMT12. E: Determination of Km and Vmax of MnASMT12 for serotonin. MnASMT12 (1.0 μg) was co-incubated with different concentrations of serotonin for 20 min at 37 ◦C. " IPTG" stand without addition of 1 mM IPTG to the E. coli BL21 (DE3) culture, "+IPTG" stand addition of 1 mM IPTG to the E. coli BL21 (DE3) culture. "TF" is Trigger Factor, a prokaryotic ribosomerelated molecular chaperone that facilitates the translation and folding of peptides. "*" indicates Trigger factor.

Fig. 3 in Genome-wide identification and characterization of genes involved in melatonin biosynthesis in Morus notabilis (wild mulberry)

Fig. 3. Purification and enzymatic analyses of recombinant His-tagged MnTDC and recombinant His-tagged MnT5H2. A: Purification of recombinant His-tagged MnTDC (lane1: Protein Marker; lane2: pCold TF (+IPTG); lane3: recombinant protein (-IPTG); lane4: recombinant protein (+IPTG); lane5: purified protein). B: Mass spectrum of compounds detected using UPLC-MS/MS. a: tryptamine standard; b: Chromatogram of tryptophan catalyzed by MnTDC. C: Determination of Km and V of MnTDC for tryptophan. The MnTDC (1.0 μg) was co-incubated with different concentrations of tryptophan for 20 min at 37 ◦C. Trp: tryptophan; Try: max tryptamine. D: Purification of recombinant His-tagged MnT5H2 (lane1: Protein Marker; lane2: pCold TF (+IPTG); lane3: recombinant protein (-IPTG) lane4: recombinant protein (+IPTG); lane5: purified protein). E: Mass spectrum of compounds detected using UPLC-MS/MS. a: serotonin standard; b: Chromatogram of tryptamine catalyzed by MnT5H2. F: Determination of Km and Vmax of MnT5H2 for tryptamine. The MnT5H2 (1.0 μg) was co-incubated with different concentrations of tryptamine for 20 min at 28 ◦C. Ser: serotonin. " IPTG" stand without addition of 1 mM IPTG to the E. coli BL21 (DE3) culture, "+IPTG" stand addition of 1 mM IPTG to the E. coli BL21 (DE3) culture. "TF" is Trigger Factor, a prokaryotic ribosome-related molecular chaperone that facilitates the translation and folding of peptides. "*" indicates Trigger factor.

Fig. 4 in Genome-wide identification and characterization of genes involved in melatonin biosynthesis in Morus notabilis (wild mulberry)

Fig. 4. Purification and enzymatic analyses of recombinant His-tagged MnSNAT5. A: Purification of recombinant His-tagged MnSNAT5 (lane1: Protein Marker; lane2: pCold TF (+IPTG); lane3: recombinant (-IPTG); lane4: recombinant (+IPTG); lane5: purified protein). B: Mass spectrum of compounds detected using UPLCMS/MS. a: N-acetylserotonin standard; b: Chromatogram of serotonin catalyzed by MnSNAT5. C: Determination of Km and Vmax of MnSNAT5 for serotonin. MnSNAT5 (1.0 μg) was co-incubated with different concentrations of serotonin for 20 min at 37 ◦C. D: Mass spectrum of compounds detected using UPLC-MS/MS. a: standard, b: Chromatogram of 5-methoxytryptamine catalyzed by MnSNAT5. E: Determination of Km and Vmax of MnSNAT5 for 5-methoxytryptamine. MnSNAT5 (1.0 μg) was coincubated with different concentrations of 5-methoxytryptamine for 20 min at 37 ◦C. " IPTG" stand without addition of 1 mM IPTG to the E. coli BL21 (DE3) culture, "+IPTG" stand addition of 1 mM IPTG to the E. coli BL21 (DE3) culture. "TF" is Trigger Factor, a prokaryotic ribosome-related molecular chaperone that facilitates the translation and folding of peptides. "*" indicates Trigger factor. NAS: N-acetylserotonin; 5-MT: 5-methoxytryptamine; Mel: melatonin.