Fig 1.
Synthesis of 4, 5, 8, 10, 14, and gigantol.
Reagents and conditions: a. NaBH4, MeOH; b. PBr3, pyridine, 0°C; c. P(OEt)3, 120°C; d. different aldehydes, CH3ONa, 0°C to room temperature (RT), 12 h; e. Pd/C, H2, RT, 12 h; f. BBr3, CH2Cl2, -20°C, 2 h; RT, 4 h; g. NaH, ethanethiol, DMF, N2, reflux; h. MOMCl, i-Pr2NEt, CH2Cl2, 0°C, 1 h; RT, 12 h; i. diethyl naphthalen-1-ylmethylphosphonate, CH3ONa, 0°C, 1 h; rt, 12 h; j. 2 M HCl, methanol, 50°C, 1 h; k. BnBr, 18-crown-6, K2CO3, reflux, 9 h.
Fig 2.
Synthesis of 17, 21, 23, and 25.
Reagents and conditions: a. TsOH, ethanol; 0°C, NaBH4; b. K2CO3, ethanol; c. Pd/C, H2, RT, 12 h; d. BBr3, CH2Cl2, -20°C, 2 h; RT, 4 h. e. Et3N, CH2Cl2; f. 180°C, neat, N2.
Table 1.
Inhibitory effect of gigantol and its analogs on AR activity1.
Table 2.
Inhibitory effect of gigantol and its analogs on iNOS activity1.
Fig 3.
Gigantol analogs at 0.1, 0.5, and 1.0 μg·mL-1 on viability of HLECs treated with 250 mmol·L-1 D-galactose for 72 h.
Cell viability was determined by the MTT assay in the absence (Con) and presence (all other groups) of D-galactose. Ext-G refers to gigantol extracted from dendrobii. Viability (mean ± SD, n = 3) is expressed as the percentage of viable cells in the treatment to those of the Con. #P < 0.01 vs. Con, *P < 0.05 vs. D-galactose.