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Fig. 5 in Hyperelodiones A-C, monoterpenoid polyprenylated acylphoroglucinols from Hypericum elodeoides, induce cancer cells apoptosis by targeting RXRα

Fig. 5. The interaction between RXRα-LBD and compounds. After treated with compounds 1–3, the binding affinity of compound toward RXRα-LBD was measured via fluorescence quenching technology at 298 K.

Fig. 7 in Hyperelodiones A-C, monoterpenoid polyprenylated acylphoroglucinols from Hypericum elodeoides, induce cancer cells apoptosis by targeting RXRα

Fig. 7. Cytotoxic effects of compounds 1–3. HeLa and MCF-7 cells were exposed to various concentrations of compounds 1–3 (0, 3.125, 6.25, 12.5, 25, 50 μΜ). After 48 h, cytotoxic activities of compounds against cancer cells were measured by MTT assay. The values are the mean ± SD for four independent replicates.

Fig. 9 in Hyperelodiones A-C, monoterpenoid polyprenylated acylphoroglucinols from Hypericum elodeoides, induce cancer cells apoptosis by targeting RXRα

Fig. 9. Molecular docking of compounds 1–3 toward RXRα-LBD. (A) Docking of 1 to RXRα-LBD. (B) Docking of 2 to RXRα-LBD. (C) Docking of 3 to RXRα-LBD. (D) Binding site of 1 to the RXRα-LBD. (E) Binding site of 2 to the RXRα-LBD. (F) Binding site of 3 to the RXRα-LBD.

Fig. 6 in Hyperelodiones A-C, monoterpenoid polyprenylated acylphoroglucinols from Hypericum elodeoides, induce cancer cells apoptosis by targeting RXRα

Fig. 6. The RXRα transactivation effects of compounds. 293T cells were treated with different concentrations of new compounds (0, 12.5, 25 μΜ), the transactivation activities of reporter gene for RXRα were measured by dual-luciferase reporter gene assay. The values are the mean ± SD for four independent replicates (*p <0.05, **p <0.01, compared with cells treated with 9-cis-RA alone).

Fig. 8 in Hyperelodiones A-C, monoterpenoid polyprenylated acylphoroglucinols from Hypericum elodeoides, induce cancer cells apoptosis by targeting RXRα

Fig. 8. PARP cleavage induction by compound 3. HeLa cells and MCF-7 cells were treated with different concentrations of compound 3 (0, 10, 20, 30 μΜ) for 48 h. The level of cleaved PARP was analyzed by Western blot.

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Fig. 4. Calculated and experimental ECD spectra for compounds 1 in Sesquiterpenoids and monoterpenoids from the water decoction of Valeriana officinalis L

Fig. 4. Calculated and experimental ECD spectra for compounds 1 (A), 3 (B), 4 (C), 5 (D, in water), 6 (E, in water), 7 (F), and 8 (G) in MeOH.

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Fig. 5 in Sesquiterpenoids and monoterpenoids from the water decoction of Valeriana officinalis L

Fig. 5. Anti-neuroinflammatory activities of compounds 1–26 in the LPS-induced BV-2 cells. A: Cell viability of BV-2 microglial cells treated with compounds and LPS. B: The effect of compounds on the production of NO in LPS-induced BV-2 cells. [Cell viability (%) = (ODtreament - ODblank) * 100/(ODcontrol - ODblank). The relative concentration of NO (%) = (Ctreatment - Ccontrol) * 100/(CLPS - Ccontrol). L is the LPS-induced BV-2 cells inflammatory model group, C is the control group, M is the minocycline as positive controls. *p <0.05, ***p <0.001 vs control group; ###p <0.001 vs LPS-induced group.].

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Fig. 4 in Monoterpenoid acylphloroglucinols from Hypericum hengshanense W. T. Wang with antiproliferative activities

Fig. 4. Antiproliferative activity of MAPs isolated from Hypericum hengshanense against five cancer cell lines (n = 3, ***p <0.001 and **p <0.01 compared with the control group, cisplatin (DDP) and taxol served as positive control).

Fig. 7. Linear correlation between experimental and calculated 13C in Discovery of Undescribed Monoterpenoid Polyprenylated Acylphloroglucinols with Immunosuppressive Activities from Hypericum longistylum

Fig. 7. Linear correlation between experimental and calculated 13C NMR chemical shifts of 5 at the B972/pcSseg-2 (A) and mPW1PW91/def2-TZVP (B) levels.

Fig. 8 in Discovery of Undescribed Monoterpenoid Polyprenylated Acylphloroglucinols with Immunosuppressive Activities from Hypericum longistylum

Fig. 8. Calculated and experimental ECD spectra of 5 (A) and experimental ECD curves of compounds 5, 6 and 7 (B) (in MeOH).

Fig. 5. Linear correlation between experimental and calculated 13C in Discovery of Undescribed Monoterpenoid Polyprenylated Acylphloroglucinols with Immunosuppressive Activities from Hypericum longistylum

Fig. 5. Linear correlation between experimental and calculated 13C NMR chemical shifts of 3 at the B972/pcSseg-2 (A) and mPW1PW91/def2-TZVP (B) levels.

Fig. 6 in Discovery of Undescribed Monoterpenoid Polyprenylated Acylphloroglucinols with Immunosuppressive Activities from Hypericum longistylum

Fig. 6. Experimental and calculated ECD spectra of 3 (A) and experimental ECD curves of compounds 3 and 4 (B) (in MeOH).

Fig. 4 in Discovery of Undescribed Monoterpenoid Polyprenylated Acylphloroglucinols with Immunosuppressive Activities from Hypericum longistylum

Fig. 4. Experimental and calculated ECD spectra of 1 (A) and experimental ECD curves of compounds 1 and 2 (B) (in MeOH).

Fig. 3. Linear correlation between experimental and calculated 13C in Discovery of Undescribed Monoterpenoid Polyprenylated Acylphloroglucinols with Immunosuppressive Activities from Hypericum longistylum

Fig. 3. Linear correlation between experimental and calculated 13C NMR chemical shifts of 1 at the B972/pcSseg-2 (A) and mPW1PW91/def2-TZVP (B) levels.

Fig. 2. Key HMBC, 1H– 1H in Hyperelodiones A-C, monoterpenoid polyprenylated acylphoroglucinols from Hypericum elodeoides, induce cancer cells apoptosis by targeting RXRα

Fig. 2. Key HMBC, 1H– 1H COSY and NOESY correlations of compounds 1–3.

Fig. 4 in Hyperelodiones A-C, monoterpenoid polyprenylated acylphoroglucinols from Hypericum elodeoides, induce cancer cells apoptosis by targeting RXRα

Fig. 4. Experimental ECD spectra of 1–3.

Fig. 1 in Hyperelodiones A-C, monoterpenoid polyprenylated acylphoroglucinols from Hypericum elodeoides, induce cancer cells apoptosis by targeting RXRα

Fig. 1. Structure of compounds 1–3.

Fig. 3 in Hyperelodiones A-C, monoterpenoid polyprenylated acylphoroglucinols from Hypericum elodeoides, induce cancer cells apoptosis by targeting RXRα

Fig. 3. Calculated and experimental ECD spectra of 1 and two tautomers.