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Fig. 5. A in Bisabolane-type sesquiterpenes from Vernonia amygdalina: Absolute configuration and anti-inflammatory activity

Fig. 5. A: Analysis of modified Mosher's method for 1. Δδ values (in ppm) = δS MTPA esters (1a) and (R)-MTPA esters (1b) at H-12.

opennotspecifiedApr 2022View details →

Fig. 2 in Cadinane sesquiterpenoids from the fungus Antrodiella albocinnamomea and their inhibitory activity against nitric oxide production

Fig. 2. Key HMBC (red arrows) and COSY (bold blue lines) correlations for compounds 1–7. (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 Bisabolane-type sesquiterpenes from Vernonia amygdalina: Absolute configuration and anti-inflammatory activity

Fig. 9. Effects of Compounds 1–8 on the NO production and the expression of iNOS and COX-2 proteins. RAW 264.7 cells were pretreated with Compounds 1–8 for 2 h and then stimulated with 1 μg/mL LPS for additional 24 h. A: The effect of Compounds 1–8 on the viability of RAW 264.7 cells. B: The inhibitory effect of Compounds 1–8 on LPS-induced NO production in RAW 264.7 cells. C: Western blot of the expression levels of iNOS and COX-2 proteins. D–E: Quantitative densitometry analysis of iNOS/β-actin and COX-2/β-actin (mean ± SD. ###p <0.001, compared with the group untreated with LPS; *p <0.05, **p <0.01 and ***p <0.001 compared with the group treated with LPS.).

Fig. 8. A in Bisabolane-type sesquiterpenes from Vernonia amygdalina: Absolute configuration and anti-inflammatory activity

Fig. 8. A: Regression analysis of experimental vs. calculated 13C NMR chemical shifts of (6R, 7S, 11R)-8; B: DP4 probability analysis for (6R*, R*, 11R*)-8 (6R*, + 7, 7R*, 11S*)-8, (6R*, 7S*, 11R*)-8 and (6R*, 7S*, 11S*)-8 at the PCM-mPW1PW91/6-31G (d, p) level.

Fig. 7. A in Bisabolane-type sesquiterpenes from Vernonia amygdalina: Absolute configuration and anti-inflammatory activity

Fig. 7. A: Experimental circular dichroism spectrum of the in situ formed Mo2(OAc)4-complex of Compound 7; B: Conformational analysis of the Mo complex of 7. The active Cotton effect of the complex at 301 nm suggests that the favoured conformation is the S-configuration at C-2′.

opennotspecifiedApr 2022View details →

Fig. 6 in Cassane-type diterpenes from roots of Pterolobium macropterum and their anti-inflammatory activity

Fig. 6. Effect of 3 and 10 on the expression of iNOS and COX-2 protein. The purity of 3 and 10 is 99% and 98%, respectively, determined with NMR spectra.

opennotspecifiedApr 2022View details →

Fig. 5 in Cassane-type diterpenes from roots of Pterolobium macropterum and their anti-inflammatory activity

Fig. 5. ORTEP diagram of 8. Letters A and B indicate the doubly disordered carbonyl oxygen sites A and B with respective occupancy factors 0.77 and 0.23.

opennotspecifiedOct 2022View details →

Fig. 5 in Chemical constituents from the fruits of Illicium simonsii and their antiviral activity and neuroprotective effect

Fig. 5. The experimental ECD spectra of 3 and 4 and calculated ECD spectra of a pair of enantiomers of the corresponding simplified structures of 12a and 12b, and Δδ (δδ) 1H NMR values (blue and red data) for the MTPA esters of compounds 3a, 3b, 4a, and 4b. (For interpretation of the references to colour in this figure S R legend, the reader is referred to the Web version of this article.)

Fig. 1 in Chemical constituents of Entandrophragma angolense and their anti-inflammatory activity

Fig. 1. Structures of undescribed compounds (1, 3, 4, 10, 13, and 24) and biologically active compounds (11 and 22).

Fig. 5 in Chemical constituents of Entandrophragma angolense and their anti-inflammatory activity

Fig. 5. (a) 1H NMR comparison of 24 and 25 (400 MHz, methanol-d). The chemical shifts of H-4a and H-4b (in the yellow box) showed significant difference 4 between 24 and 25. (b) 1H–1H COSY and HMBC key correlations of 24. (c) Experimental and calculated ECD spectra of 24. (d) Molecular network of the E. angolense butanol fractions (B1–B5). The network showed a cluster containing catechin derivatives. Nodes are labelled with parent ion mass (negative mode) and connected by edges which represent the structural similarity based on MS/MS fragmentation pattern. GNPS library hits are labelled in red. Even though the m/z 451 node did not have reliable GNPS library hits, the connected edges suggested that this ion could be a structurally related catechin derivative. Later, an undescribed catechin glucoside (24) was isolated from the fraction B2 and supported that GNPS helps to find undescribed structures in the species. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 7 in Chemical constituents of Entandrophragma angolense and their anti-inflammatory activity

Fig. 7. Effects of 1–25 on nitric oxide production, cytotoxicity, and iNOS expression in LPS-treated murine macrophage RAW 264.7 cells. (a) NO inhibition (%) at 1 μM and cytotoxicity (%) at 100 μM of the compounds. Compounds showing 60–80% NO inhibition and <20% cytotoxicity (blue circle) were selected. (b) Western blotting of iNOS protein. For compounds 11, 14, and 22–25, total cellular proteins were separated by SDS-PAGE and transferred to nitrocellulose membranes to detect murine iNOS and β-actin (internal control) for the normalization of iNOS protein expression. The increase/decrease of iNOS/β-actin ratio (%) was expressed relative to the control group (containing LPS only, lane 2). Compounds 11 and 22 reduced LPS-induced iNOS protein levels. The western blot analysis was performed in duplicate experiments. (c)–(e) EC50 fitting curves and cell viability (%) of 11, 22, and EGCG at concentrations of 200.0, 100.0, 50.0, 25.0, 12.5, 6.3, and 3.1 μM EC50 values of 11, 22, and EGCG were estimated to be 81.3, 137.4, and 44.6 μM, respectively. Cell viability (%) was 86.4, 73.8, and 56.7% at the highest concentration, respectively. (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. 3 in Chemical constituents of Antidesma bunius aerial parts and the anti-AGEs activity of selected compounds

Fig. 3. Experimental CD spectra of 1 and 2; (B–F) Calculated and experimental ECD spectra of 2, 3, 4, 5, and 8.

opennotspecifiedJan 2022View details →

Fig. 6 in Comprehensive characterization of polyacetylenes and diterpenes from the underground parts of Solidago altissima L. and their contribution to the overall allelopathic activity

Fig. 6. Effects of the n-hexane extract (A), cis-dehydromatricaria ester (cis-DME, 1) (B), 13E-7α-acetoxy kolavenic acid (7) (C), (2Z, 8Z)-10-tigloyloxy matricaria ester (8) (D), (2Z, 8Z)-10-angeloyloxy matricaria ester (9) (E), and 13E-kolavenic acid (10) (F) on the root and shoot lengths of Italian ryegrass seedlings. The bioassays of isolated compounds B–F were performed at their concentrations in the n-hexane extracts shown in (A). The values are expressed as means ± standard deviation. Different letters represent significant differences between treatments (p <0.05, one-way ANOVA via Tukey's multiple comparison test).

opennotspecifiedJan 2022View details →

Fig. 1 in Comprehensive characterization of polyacetylenes and diterpenes from the underground parts of Solidago altissima L. and their contribution to the overall allelopathic activity

Fig. 1. High-performance liquid chromatography/diode array detection, total ion current (TIC), and extracted ion current chromatograms of the extract of the underground parts of S. altissima. (A) Monitored at 254 nm; (B) monitored at 230 nm; (C) monitored at 330 nm; (D) operated in positive ion mode. a) TIC, b) m/z 273.111 ([M H]+ of compounds 8 and 9), c) m/z 261.113 ([M H]+ of compound 6), d) m/z 259.095 ([M H]+ of compounds 2–4), e) m/z 173.061 ([M + + + + H–C H O]+ of compound 4), f) m/z 159.045 ([M + H–C H O]+ of compounds 2 and 3); (E) TIC in negative ion mode. The scale factors of the chromatograms are 4 6 2 5 8 2 indicated in parentheses. The numbers in the figure correspond to the compounds listed in Table 1.

Fig. 1 in Comprehensive evaluation of Bletilla striata and its substitutes by combining phenotypic characteristic, chemical composition, and anti-melanogenic activity

Fig. 1. Plant morphological characteristics of B. striata (A1 aerial part, A2 pseudobulb), B. ochracea (B1 aerial part, B2 pseudobulb) and B. formosana (C1 aerial part, C2 pseudobulb).

opennotspecifiedFeb 2022View details →

Fig. 4 in Dammarane-type saponins with proprotein convertase subtilisin/kexin type 9 inhibitory activity from Gynostemma pentaphyllum

Fig. 4. Effects of compounds 1–11 on cell viabilities and PCSK9 inhibitory activities in HepG2 cells. (A–B) The cell viability assay of compounds 1–11 with different concentrations (5, 10, 20, 40, and 80 μM) in HepG2 cells. (C) Effect of compounds 1–11 (20 μM) and BBR (berberine, 10 μM) on the expression of PCSK9 in HepG2 cells. (D) Effect of compounds 1–11 (10 μM) and BBR (berberine, 10 μM) on the expression of PCSK9 in HepG2 cells. (E) Effect of compounds 2, 5 (5 μM) and BBR (berberine, 10 μM) on the expression of PCSK9 in HepG2 cells. The expression of PCSK9 was assayed by ELISA in HepG2 cells treated with compounds 1–11 and BBR (berberine) for 24 h. The results were calculated as the means ± SD of three independent experiments. ###p <0.001 vs control group; *p <0.05, **p <0.01, ***p <0.001 vs model group.

Fig. 3 in Comprehensive evaluation of Bletilla striata and its substitutes by combining phenotypic characteristic, chemical composition, and anti-melanogenic activity

Fig. 3. UPLC chromatographic fingerprints of 27 Bletillae Rhizoma samples (S1–S27) and the reference fingerprint (R). The peaks marked with 1–19 represent the 19 common peaks.

opennotspecifiedJan 2022View details →

Fig. 5 in Comprehensive characterization of polyacetylenes and diterpenes from the underground parts of Solidago altissima L. and their contribution to the overall allelopathic activity

Fig. 5. Effects of the n-hexane extract (A), cis-dehydromatricaria ester (cis-DME, 1) (B), 13E-7α-acetoxy kolavenic acid (7) (C), (2Z, 8Z)-10-tigloyloxy matricaria ester (8) (D), (2Z, 8Z)-10-angeloyloxy matricaria ester (9) (E), and 13E-kolavenic acid (10) (F) on the root and shoot lengths of lettuce seedlings. The bioassays of isolated compounds B–F were performed at their concentrations in the n-hexane extracts shown in (A). The values are expressed as means ± standard deviation. Different letters represent significant differences between treatments (p <0.05, one-way ANOVA via Tukey's multiple comparison test).

Fig. 2 in Comprehensive evaluation of Bletilla striata and its substitutes by combining phenotypic characteristic, chemical composition, and anti-melanogenic activity

Fig. 2. Microscopic characteristics of B. striata (A), B. ochracea (B), and B. formosana (C). (1.Epidermal cell 2. Raphid of calcium oxalate 3. Mucilage cell 4. Vessel 5. Fiber 6. Starch granule).

Fig. 9 in Comprehensive evaluation of Bletilla striata and its substitutes by combining phenotypic characteristic, chemical composition, and anti-melanogenic activity

Fig. 9. The docking complex of two compounds with tyrosinase and adenylate cyclase. (A) Coelonin in active pocket site of tyrosinase. (B) Batatasin III in an active pocket site of adenylate cyclase. (C) Coelonin formed 2 hydrogen bonds with the amino acid residues of tyrosinase. (D) Batatasin III formed 2 hydrogen bonds with the amino acid residues of adenylate cyclase.