*3.3. Fermentation*

The fungus *Penicillum* sp. N-5 was cultured in one hundred 1000 mL Erlenmeyer flasks at 25 ◦C for 30 days; these contained autoclaved rice solid-substrate medium composed of 50 g rice and 50 mL 3‰ saline water.

#### *3.4. Extraction and Purification*

After incubation, the mycelia and solid rice medium were extracted four times with EtOAc, and 75 g of residue was obtained. Next, the residue was separated by a gradient of petroleum ether/EtOAc from 9:1 to 0:10 (*v*/*v*) on silica gel CC and divided into six fractions (Fr.1–Fr.6). Fr. 2 (10 g) was separated to Sephadex LH-20 (methanol) to yield three sub-fractions (SFrs. 2.1–2.3). SFrs.2.3 (1.2 g) was applied to silica gel CC (DCM/MeOH *v*/*v*, 100:1) and further purified by reversed-phase (RP) high performance liquid chromatography (HPLC; 90–10% MeCN/H2O for 25 min) to obtain compounds **1** (5 mg) and **3** (7 mg). Fr. 3 (16 g) was also separated to Sephadex LH-20 (methanol) to yield four sub-fractions (SFrs. 3.1–3.4). SFrs.3.1 (1.6 g) was separated to silica gel CC (DCM/MeOH *v*/*v*, 80:1) and further purified by reversed-phase (RP) high performance liquid chromatography (HPLC; 75–25% MeCN/H2O for 22 min) to yield compounds **2** (11 mg) and **15** (6 mg).

Hemiacetalmeroterpenoid A (**1**): white powder, m.p. 122.8–124.1 ◦C; [*α*] 25 <sup>D</sup> -52 (*c* 0.02, MeOH), UV (MeOH) λmax (log *ε*): 206 (2.52) (Figure S33); ECD (MeOH) λmax (Δ*ε*): 240 (+5.47), 301 (−1.14), 362 (+0.61); 1H (600 MHz, CD3OD) and 13C NMR (150 MHz, CD3OD) data, see Table 1; HR-ESI-MS: *m*/*z* 459.23709 [M+H]+ (calcd. for C26H35O7, 459.23773).

Hemiacetalmeroterpenoid B (**2**): white powder, m.p. 106.9–108.4 ◦C; [*α*] 25 <sup>D</sup> −56 (*c* 0.02, MeOH), UV (MeOH) λmax (log *ε*): 205 (2.83), 238 (1.36) (Figure S34); ECD (MeOH) <sup>λ</sup>max (Δ*ε*): 206 (−11.92), 248 (+3.38), 311 (−1.19); 1H (600 MHz, CD3OD) and 13C NMR (150 MHz, CD3OD) data, see Table 1; HR-ESI-MS: *m*/*z* 445.25772 [M+H]<sup>+</sup> (calcd. for C26H37O6, 445.25847).

Hemiacetalmeroterpenoid C (**3**): white powder, m.p. 100.8–102.6 ◦C; [*α*] 25 <sup>D</sup> −66 (*c* 0.02, MeOH), UV (MeOH) λmax (log *ε*): 205 (2.51), 260 (1.78) (Figure S35); ECD (MeOH) λmax (Δ*ε*): 206 (−18.31), 240 (+12.72), 310 (−2.18); 1H (600 MHz, CD3OD) and 13C NMR (150 MHz, CD3OD) data, see Table 1; HR-ESI-MS: *m*/*z* 509.25015 [M+Na]<sup>+</sup> (calcd. for C28H38O7Na, 509.25097).

Astellolide J (**14**): yellow powder, m.p. 202.9–204.5 ◦C; [*α*] 25 <sup>D</sup> +16 (*c* 0.02, MeOH), UV (MeOH) λmax (log *ε*): 216 (3.15) (Figure S36); ECD (MeOH) λmax (Δ*ε*): 203 (−1.82), 225 (+3.27); 1H (400 MHz, CD3OD) and 13C NMR (100 MHz, CD3OD) data; HR-ESI-MS: *m*/*z* 305.13565 [M+Na]+ (calcd. for C15H22O5Na, 305.13594).

Astellolide Q (**15**): yellow powder, m.p. 160.1–162.2 ◦C; [*α*] 25 <sup>D</sup> +12 (*c* 0.02, MeOH), UV (MeOH) λmax (log *ε*): 218 (3.62) (Figure S37); ECD (MeOH) λmax (Δ*ε*): 232 (+5.19); 1H (400 MHz, CD3OD) and 13C NMR (100 MHz, CD3OD) data, see Table 2; HR-ESI-MS: *m*/*z* 347.14578 [M+Na]+ (calcd. for C17H24O6Na, 347.14578).
