*4.4. Extraction and Isolation*

The sorted-out lichen *Ramalina conduplicans* (300 g) was shade-dried, powdered, and extracted with acetone (6L) at room temperature for 48h. The result was that acetone extract was evaporated to dryness under reduced pressure, thereby affording a syrupy residue (20 g). This crude extract was subjected to gradient column chromatography (SiO2, 60–120 mesh) and eluted with a hexane/EtOAc mixture of increasing polarity with 10% intervals that yielded 8 fractions. These eight fractions were reconstituted in acetonitrile and subjected to UPLC Q-ToF MSE. Based on the TIC profile, we selected fractions 3–6 for purification (mass profile shown in supporting information, discussion in results section). All these fractions were subjected to semi-preparative HPLC (X Select HSST3 OBD Prep Column,5 μm, 10 mm × 250 mm), 0.1 % formic acid with water (solvent A) and acetonitrile (solvent B) as mobile phase at flow rate 4 mL/min, detected at 254 nm. Semi-preparative HPLC were conducted by gradient elution programs to obtain compounds as follows: Fraction 3 (quantity 70 mg, loop volume 250 μL was eluted by 0 min, 5% B; 5 min, 5% B; 10.00 min, 35% B; 16.00 min, 60% B; 25 min, 95% B; 30 min, 95% B; 5% B; 30.50 min, 5% B; 35.00 min. to yield **3** (homosekikaic acid, 7 mg), **7** (divaricatic acid, 4 mg), **11** (divaricatinic acid, 3 mg), **12** (olivetolic acid, 5 mg), and **14** (atranol, 2 mg). Fraction 4 (quantity 50 mg, loop volume 250 μL was eluted by 0 min, 30% B; 5 min, 30% B; 10.00 min, 50% B; 23.00 min, 95% B; 27.00 min, 95% B; 27.50 min, 30% B; 30% B; 30.00 min at flow rate 4 mL/min, detected at 254 nm to yield **10** (methyldivaricatinate, 3 mg), **8** (decarboxydivaricatic acid, 5 mg), **9** (decarboxystenosporic acid, 2 mg), and **4** (hyperhomosekikaic acid, 1mg). Fraction 5 (quantity 25 mg, loop volume 250 μL was eluted by 0 min, 5% B; 8.50 min, 30% B; 15.00 min, 50% B; 22.00 min, 95% B; 28.00 min, 95% B; 29.0 min, 5% B; 5% B; 35.00 min at flow rate 4 mL/min, detected at 254 nm) to yield **13** (divarinolmonomethylether, 3 mg) and compound **5** (2 mg). Fraction 6 (quantity 40 mg, loop volume 250 μL was eluted by 0 min, 10% B; 8.50 min, 40% B; 18.00 min, 55% B; 25.00 min, 75% B; 32.00 min, 95% B; 36.0 min, 95% B; 10% B; 37.00 min, 10% B; 42.00 min at flow rate 4 mL/min, detected at 254 nm) to yield **1** (sekikaic acid, 5 mg), **2** (4-*O*-methylnorhomosekikaic acid, 7 mg) and 2,4-di-*O*-methyldivaric acid **6** (2 mg). Physicochemical data are shown in the Supporting Materials.

#### *4.5. In Vitro Antihyperglycemic and Antioxidant Assay*
