Figures & data
Figure 2. 1H-1H COSY (bold lines), HMBC (blue arrows), and NOESY (dash line arrows) correlations of compound 1.
![Figure 2. 1H-1H COSY (bold lines), HMBC (blue arrows), and NOESY (dash line arrows) correlations of compound 1.](/cms/asset/9d0be355-8151-4165-b8fd-6b1d580f04c7/ienz_a_2296355_f0002_c.jpg)
Table 1. 1H and 13C NMR spectral data (500 MHz for 1H and 125 MHz for 13C in methanol-d4) of compound 1 (δ in ppm, J in Hz).
Figure 3. Experimental ECD curve of compound 1 (solid red line), and M062X/TZVP//B3LYP/6-31G(d) calculated ECD spectra of 1 R,2S,3S,5S,7R,10S,13R-1 (solid black line) and 1S,2R,3R,5R,7S,10R,13S-1 (dash black line).
![Figure 3. Experimental ECD curve of compound 1 (solid red line), and M062X/TZVP//B3LYP/6-31G(d) calculated ECD spectra of 1 R,2S,3S,5S,7R,10S,13R-1 (solid black line) and 1S,2R,3R,5R,7S,10R,13S-1 (dash black line).](/cms/asset/18088c92-db61-4996-b9ec-7c877dc00bfd/ienz_a_2296355_f0003_c.jpg)
Scheme 1. Structures and reactions in modifications of orthosiphol K (4).a
a Reagents and conditions: (a) Cs2CO3, DMF, 3-OMePhCH2Br, 80 °C, reflux; (b) Cs2CO3, DMF, CH3CH2Br, 80 °C, reflux; (c) Propanoic acid, DMAP, EDCI, CH2Cl2, 0-25 °C,6h; (d) Cs2CO3, DMF, MeI, r.t., 24h; (e) Jones reagent, acetone, 0-25 °C, 1.5-2h; (f) NH4OH/MeOH, 110 °C, reflux, 0.5-1h.
![Scheme 1. Structures and reactions in modifications of orthosiphol K (4).aa Reagents and conditions: (a) Cs2CO3, DMF, 3-OMePhCH2Br, 80 °C, reflux; (b) Cs2CO3, DMF, CH3CH2Br, 80 °C, reflux; (c) Propanoic acid, DMAP, EDCI, CH2Cl2, 0-25 °C,6h; (d) Cs2CO3, DMF, MeI, r.t., 24h; (e) Jones reagent, acetone, 0-25 °C, 1.5-2h; (f) NH4OH/MeOH, 110 °C, reflux, 0.5-1h.](/cms/asset/2c69c51a-c775-43a3-8cf7-a46ed9865e7c/ienz_a_2296355_sch0001_c.jpg)
Figure 4. Cytokine release levels in TNF-α-induced MH7A cell model. (A) IL-1β release levels. (B) IL-6 release levels (####p < 0.0001, vs. control group; *p < 0.05, **p < 0.01, ***p < 0.001, ****p < 0.0001, vs. model group).
![Figure 4. Cytokine release levels in TNF-α-induced MH7A cell model. (A) IL-1β release levels. (B) IL-6 release levels (####p < 0.0001, vs. control group; *p < 0.05, **p < 0.01, ***p < 0.001, ****p < 0.0001, vs. model group).](/cms/asset/678fe1e7-4141-4bfd-a112-e6f669031c70/ienz_a_2296355_f0004_b.jpg)
Figure 5. Effect of compound 10 on TNF-α-induced IκBα, NF-κB p65, COX-2, and NLRP3 protein expression in MH7A cells. (A) Western blot analysis and (B) Quantified protein expression levels. (#p < 0.05, ##p < 0.01, ####p < 0.0001, vs control group; *p < 0.05, ***p < 0.001, ****p < 0.0001, vs. model group).
![Figure 5. Effect of compound 10 on TNF-α-induced IκBα, NF-κB p65, COX-2, and NLRP3 protein expression in MH7A cells. (A) Western blot analysis and (B) Quantified protein expression levels. (#p < 0.05, ##p < 0.01, ####p < 0.0001, vs control group; *p < 0.05, ***p < 0.001, ****p < 0.0001, vs. model group).](/cms/asset/75b08f9e-669a-468a-9b1c-2e892708a23d/ienz_a_2296355_f0005_c.jpg)