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opennotspecifiedJan 2022View details →

Fig. 1 in Polyketide-derived macrobrevins from marine macroalga-associated Bacillus amyloliquefaciens as promising antibacterial agents against pathogens causing nosocomial infections

Fig. 1. Structural representation of (A) trihydroxy-decahydro-37-methyl-macrobrevin (compound 1), (B) hexahydro-macrobrevin (compound 2), (C) hexahydro-41- hydroxy-macrobrevin-31-acetate (compound 3), and (D) hexahydro-28-nor-methyl-5-methoxy-macrobrevin (compound 4) isolated from marine macroalgaassociated B. amyloliquefaciens MTCC 12713. (E) The zone of inhibition (34 mm) observed with hexahydro-41-hydroxy-macrobrevin-31-acetate (compound 3) against VREfs as visualized on Mueller Hinton agar plates by disc diffusion assay was illustrated. The amounts of compound 3 and chloramphenicol were 30 μg per disc. Chloramphenicol and ethyl acetate, which were used as the positive and negative control, were denoted with (+) and (), respectively.

opennotspecifiedJan 2022View details →

Fig. 2. 1H–1H in Polyketide-derived macrobrevins from marine macroalga-associated Bacillus amyloliquefaciens as promising antibacterial agents against pathogens causing nosocomial infections

Fig. 2. 1H–1H COSY/HMBC (A-D) correlations of macrobrevin analogues (1–4). Key 1H–1H COSY correlations and HMBC pairings were characterized by bold-faced bonds and double-barbed arrows, respectively.

opennotspecifiedJun 2022View details →

Fig. 2 in Polyketides, diketopiperazines and an isochromanone from the marine-derived fungal strain Fusarium graminearum FM1010 from Hawaii

Fig. 2. Key COSY (bolds) and HMBC (red arrows) correlations of compound 1–4, and 6. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

opennotspecifiedJan 2022View details →

Fig. 8 in Structures and absolute configurations of butenolide derivatives from the isopod-associated fungus Pidoplitchkoviella terricola

Fig. 8. (A) The binding mode of 10 (yellow) in complex with mushroom tyrosinase. Hydrogen bonds interactions were indicated by dotted red lines. (B) Compound 10 was docked into the binding pocket of the mushroom tyrosinase. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

opennotspecifiedOct 2022View details →

Fig. 2 in Three unusual hybrid sorbicillinoids with anti-inflammatory activities from the deep-sea derived fungus Penicillium sp. SCSIO06868

Fig. 2. Global natural products social molecular networking analysis of HR- MS/MS of culture extracts derived from Penicillium sp. SCSIO06868 and the cluster corresponding to undescribed sorbicillinoids in this study.

opennotspecifiedOct 2022View details →

Fig. 6 in Three unusual hybrid sorbicillinoids with anti-inflammatory activities from the deep-sea derived fungus Penicillium sp. SCSIO06868

Fig. 6. Linear regression analysis of calculated 13C NMR shifts of (1′S)-1 (right) and (1′R)-1 (left) against the experimental shifts of 1 and the DP4 probability for + assignment of 1 to the candidate stereoisomers.

Fig. 2 in Feruloyl sucrose derivatives from the root of Xerophyllum tenax

Fig. 2. Selected HMBC (solid arrows) and NOESY (dashed arrows) correlations for compounds 1, 3 and 5.

Fig. 2 in Abyssomicin derivatives from the rhizosphere soil actinomycete Microbispora rhizosphaerae sp. nov. TBRC6028

Fig. 2. Chemical structures of the isolated compounds from the soil actinomycete Microbispora rhizosphaerae sp. nov. TBRC6028.

Fig. 4 in Feruloyl sucrose derivatives from the root of Xerophyllum tenax

Fig. 4. Proposed fragmentation pathway of compound 1–5. A. The MS2 spectrum of compounds 1 and 5; positive mode. B. The MS2 spectrum of compound 1 and 5; negative mode. C. Proposed fragmentation pathway of compound 1; positive mode. D. Proposed fragmentation pathway of compounds 1 and 5; negative mode.

Fig. 5 in Biotransformation of artemisinic acid to bioactive derivatives by endophytic Penicillium oxalicum B4 from Artemisia annua L.

Fig. 5. Time course for the biotransformation of artemisinic acid (AA) by Penicillium oxalicum B4. AA (3.50 mg/50 mL) was added to 2-day-old culture for the biotransformation.

Fig. 4 in Biotransformation of artemisinic acid to bioactive derivatives by endophytic Penicillium oxalicum B4 from Artemisia annua L.

Fig. 4. Time course of mycelial biomass (A) and the biotransformation of artemisinic acid (AA) by Penicillium oxalicum B4. AA (3.50 mg/50 mL) was added to 2-day-old culture for the biotransformation. Data presented are the means ± SD of results from three independent experiments.

Fig. 7 in Biotransformation of artemisinic acid to bioactive derivatives by endophytic Penicillium oxalicum B4 from Artemisia annua L.

Fig. 7. Inhibitory effects of metabolite 4 (A) and 7 (B) on cell viability and LPSinduced nitrite production in RAW 264.7 cells. Normal cells were incubated for 24 h with metabolite 4 and 7 at indicated concentrations. Cells were pretreated with the indicated concentrations of metabolite 4 and 7 for 1 h followed by treatment with LPS (1.0 μg/mL). After 24 h of incubation, the amount of nitrite in the culture supernatants and cell viability were measured. Data presented are the means ± SD of results from three independent experiments (###p <0.001 versus untreated group; *p <0.05, **p <0.01 versus LPS treated group. The small letters indicate the significant difference (p <0.05) between groups).

opennotspecifiedAug 2021View details →

Fig. 3 in Pyrazinopyrimidine alkaloids from a mangrove-derived fungus Aspergillus versicolor HDN11-84

Fig. 3. DP4+ probability analyses for candidates diastereomers of 1 and 2 (Gibbs free energies at the PCM/B3LYP/6-31+G (d,p) level were used for the analysis).

opennotspecifiedAug 2021View details →

Fig. 1 in An overview on the role of plant-derived tannins for the treatment of lung cancer

Fig. 1. Molecular targets modulated by tannins in lung cancer. Tannins Abbreviations: CASU - casuarinin; EGCG - epigallocatechin-3-gallate; FPTF - fructus phyllanthi tannin fraction; GA – gallic acid; GERA - geraniin; GRA – granatin A; GRB – granatin B; GSPs - grape seed proanthocyanidins; GSPC - grape seed procyanidins; OEB - oenothein B; PAC – proanthocyanidin rich cranberry fraction; PARE – procyanidin rich extract from sorghum bran; PBOG - prodelphinidin B-2 3′-Ogallate; PCC – procyanidins from cinnamomi cortex; PCCC – procyanidin C1 from cinnamomi cortex; PRFR – proanthocyanidin rich fraction from red rice; TA - tannic acid; TT – total tannins. Abbreviations for molecules: AP-1 - Activator protein 1; Apaf-1 - Apoptotic protease activating factor 1; BAX - BCL2 Associated X; BCL2 - Bcell lymphoma 2; BCL-XL - B-cell lymphoma-extra large; CD31 - cluster of differentiation 31; CDK - cyclin dependent kinase; CDKN1A - cyclin-dependent kinase inhibitor; c-FLIP - FLICE-like inhibitory protein; Cip1/p21 - cyclin-dependent kinase inhibitor 1; COX-2 – cyclooxygenase-2; Cyt C - cytochrome C; E-Cad – E-cadherin; EMT – epithelial-to-mesenchymal transition; Fas - apoptosis antigen 1; FasL - Fas ligand; FN - fibronectin; GR – glutathione reductase; GSH – reduced glutathione; GST - glutathione S-transferase; 15-HETE - 15-hydroxyeicosatetraenoic acid; IGFBP-3 - insulin like factor binding protein 3; IGF-2R - insulin-like growth factor 2 receptor; Kip1/p27 - cyclin-dependent kinase inhibitor 1B; MAPK - mitogen-activated protein kinase; MDM2 - mouse double minute 2 homolog; mFasL - membrane-bound FasL; miR – microRNA; NANOG - transcriptional factor; N-cad - N-cadherin; NOX - NADPH oxidase; NF-kB - nuclear factor kappa-light-chainenhancer of activated B cells; NRF2 - nuclear factor erythroid 2 (NFE2)-related factor 2; NQO1 - NAD(P)H:quinone oxidoreductase; OCT-4 - octamer-binding transcription factor 4; PARP - poly-ADP ribose polymerase; PCNA - proliferating cell nuclear antigen; PGE2 - prostaglandin E2; 6-keto-PGF1α - 6-keto-prostaglandin F1α; PTEN - phosphatase and tensin homolog; PTGIS - prostacyclin synthase; pMDM2 – phospho mouse double minute 2 homolog; pAKT – phosphorylated protein kinase B; pERK1/2 – phosphorylated extracellular signal-regulated kinase 1/2; pJNK1/2 – phosphorylated c-Jun N-terminal kinase 1/2; pNF-kB - phosphorylated nuclear factor kappa-light-chain-enhancer of activated B cells; pPI3K – phosphorylated phosphatidylinositol 3-kinase; α-SMA – alpha-smooth muscle actin; pSmad2 – phosphorylated SMAD family member 2; pSmad3 – phosphorylated SMAD family member 3; p21/WAF1 - cyclin-dependent kinase inhibitor 1; p22phox - human neutrophil cytochrome b light chain; p47phox – neutrophil cytosol factor 1; pp38 – phosphorylated p38; Rb - retinoblastoma protein; sFasL - soluble FasL; Smac/ DIABLO - Second mitochondria-derived activator of caspase/direct inhibitor of apoptosis-binding protein with low pI; SNAIL1 - Zinc finger protein SNAI1; SOX2 - SRY (sex determining region Y)-box 2; pEGFR – phosphorylated epidermal growth factor receptor; TGF-βR1 - transforming growth factor beta receptor; UGT - uridine diphosphate glucuronosyl transferase; VIM - vimentin; VEGF - vascular endothelial growth factor; XIAP - X-linked inhibitor of apoptosis protein; ZO1 - Zonula occludens1. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

opennotspecifiedAug 2021View details →

Fig. 2 in An overview on the role of plant-derived tannins for the treatment of lung cancer

Fig. 2. Schematic representation of the mechanism of action of tannins as apoptosis inducers, by targeting multiple cellular signal transduction pathways involved in cancer. Abbreviations: AA - arachidonic acid; Akt - protein kinase B; Axl - AXL receptor tyrosine kinase; BAX - BCL2 Associated X; BCL2 - B-cell lymphoma 2; BCL-XL - B-cell lymphoma-extra large; cAMP - adenosine 3′,5′-cyclic monophosphate; CASU - casuarinin; COX2 – cyclooxygenase 2; Cyt C - cytochrome c; EGCG - epigallocatechin-3-gallate; EGFR - epidermal growth factor receptor; EP receptor - E prostanoid receptor; FADD - Fas-associated protein with death domain; Fas - apoptosis antigen 1; FasL - Fas ligand; FPTF - fructus phyllanthi tannin fraction; GA – gallic acid; GERA - geraniin; GRA - granatin A; GRB - granatin B; GSP - grape seed proanthocyanidins; GSPC - grape seed procyanidins; 15-HETE - 15-Hydroxyeicosatetraenoic acid; IP receptor - prostacyclin receptor; 15-LOX-2 - 15-lipoxygenase-2; MAPK - mitogen-activated protein kinase; MMP - mitochondrial membrane potential; OEB - oenothein B; PAC – proanthocyandin-rich cranberry fraction; PARP - poly-ADP ribose polymerase; PBOG - prodelphinidin B-2 3′-O-gallate; PGE - prostaglandin E2; PGI - prostaglandin I2; PKA - protein kinase A; PI3K - 2 2 phosphatidylinositol 3-kinase; PLA2 - phospholipase A2; PTGIS - prostacyclin synthase; ROS - reactive oxygen species; TA – tannic acid; TAM receptors - receptor tyrosine kinases; Tyro3 - TYRO3 protein tyrosine kinase. (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 Acylphloroglucinol derivatives with ATP citrate lyase inhibitory activities from Syzygium oblatum Wall.

Fig. 4. (A) The predicted binding mode of 1 with ACLY and the ligand is shown as yellow sticks. (B) A two-dimensional plot showing the interactions between 1 and the surrounding amino acids. (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)

Fig. 4 in α-Glucosidic hydroquinone derivatives from Viburnum erosum

Fig. 4. Tyrosinase inhibitory activities of compounds 1–10, isolated from V. erosum. β-arbutin is used as the positive control.

Fig. 5 in Screening of in vitro and in silico α-amylase, α-glucosidase, and lipase inhibitory activity of oxyprenylated natural compounds and semisynthetic derivatives

Fig. 5. Docking of compounds 3, 9, 11 and 15 in human lipase. The structure of lipase (green surface) with the residues lining the binding pocket (sticks with white carbons) and the catalytic resides (S169, D193 and H280 in yellow). The docking results in lipase with compounds 3 (pink, A), 9 (cyan, B), 11 (magenta, C) and 15 (green, D) are shown with their main interacting residues labelled, hydrogen bonds and binding energies. (E) Zoom in on the superimposition of the docked compounds 3, 9, 11 and 15 (coloured as in A-D) with the position of the aromatic rings encircled and the residues, which interact with all compounds of them, are labelled. (F) The original structure of lipase (1LPB) contains the inhibitor methoxy-undecylphosphinic acid (MUP in purple). (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 α-Glucosidic hydroquinone derivatives from Viburnum erosum

Fig. 3. Δδ SR (δ δ) values (ppm, CDCl) of the MTPA esters of 5 and 6 (A), and comparison of the ECD spectra of 5, 6, and their molybdenum derivatives in S R 3 DMSO (B). National University, and identified by Prof. Yong Soo Kwon at the College of Pharmacy, Kangwon National University.

Fig. 1 in α-Glucosidic hydroquinone derivatives from Viburnum erosum

Fig. 1. Cytotoxic (A) and tyrosinase inhibition activities (B) of eight EtOAc subfractions; VEE1–8 (100 mg/ml).