*3.3. Extraction and Isolation*

The fungus *Penicillium* sp. BJR-P2 was fermented on solid autoclaved rice medium using one hundred 1 L Erlenmeyer flasks, each was containing 40 g rice and 40 mL 0.3% saline water, culturing in room temperature under static condition for 25 days. The solid rice and mycelia medium were extracted with methanol for three times. The organic solvents were evaporated under reduced pressure and extracted with ethyl acetate. We obtained 50 g of organic extract. Then, the extract was subjected to a silica gel column eluting with a gradient of petroleum ether/EtOAc from 1/0 to 0/1 to afford six fractions (Fractions 1–6). Fraction 2 (300 mg) was subjected to an open silica gel glass column eluted with DCM:MeOH (100:1) followed by Sephadex LH-20 open glass (30 mg) CC eluting with MeOH-H2O (*v/v*, 7:3), and further purified by using HPLC on a semipreparative column (RP-18, 9.4 × 250 mm, 7 <sup>μ</sup>m, 1.5 mL min<sup>−</sup>1) eluted with MeOH:H2O (6:4) to obtain compounds **1** (9.0 mg) and **4** (5.0 mg). Further separation of fraction 3 by preparative HPLC over silica gel (250 mm × 10 mm) with PE-EtOAc (4:2–1:1) and DCM:MO (200:1-80:1) as the eluent afforded **2** (10.0 mg) and **3** (5.0 mg). Fraction 4 (500 mg) was chromatographed on Sephadex LH-20 CC and silica gel CC to obtain compounds **5–8**.

Compound **1**: white powder; [α] 25 <sup>D</sup> − 88.9◦ (c 0.1, MeOH); IR (KBr): νmax 3696, 1646, 1585 cm<sup>−</sup>1; UV (MeOH) λmax (logε): 216 (0.91) nm; 268 (0.53) nm; 303 (0.22); ECD (MeOH) *λ*max (Δε), 228 (+1.56), 237 (−1.01), 247 (+2.02), 270 (−2.15), 305 (+1.20) nm; HRESIMS at *m/z* 293.1024 [M − H]<sup>−</sup> (calcd for 293.1031). 1H and 13C NMR see Table 1.

Compound **2**: white powder; [α] 25 <sup>D</sup> − 62.0◦ (c 0.1, MeOH); IR (KBr): νmax 3680, 1736, 1671, 1580 cm−1; UV (MeOH) λmax (log ε): 216 (0.89) nm; 268 (0.52) nm; 303 (0.21); ECD (MeOH) λmax (Δε), 222 (+1.25), 236 (−1.23), 250 (−0.31), 269 (−2.43), 295 (+1.48) nm; HRESIMS at *m/z* 291.08727 [M − H]<sup>−</sup> (calcd for 291.08741). 1H and 13C NMR see Table 1.

Compound **3**: yellow oil; [α] 25 <sup>D</sup> − 10◦ (c 0.1, MeOH); IR (KBr): νmax 3685, 1725, 1693, 1612 cm<sup>−</sup>1; UV (MeOH) λmax (logε): 274 (0.65) nm; 367 (0.5) nm; HRESIMS at *m/z* 415.17607 [M − H3O]<sup>−</sup> (calcd for 415.17623). 1H and 13C NMR see Table 2.

Compound **4**: yellow oil; [α] 25 <sup>D</sup> − 10◦ (c 0.1, MeOH); IR (KBr): νmax 3696, 1694, 1623 cm<sup>−</sup>1; UV (MeOH) λmax (logε): 274 (0.96) nm; 368 (0.78) nm; HRESIMS at *m/z* 417.19163 [M − H3O]<sup>−</sup> (calcd for 417.19188). 1H and 13C NMR see Table 2.

X-ray Crystal Data for **1**. Colorless crystal of **1** was obtained in methanol and EtOAc. Crystal data (CCDC 2131096) were collected with Cu Kα radiation. Monoclinic, space group P21, a = 7.18058(6) Å, b = 7.48777 (11) Å, c = 13.48676 (10) Å, α = 90◦, β = 92.3992 (7) ◦, γ = 90, V = 724.501(14) Å3, Z = 2, T = 149.99(10) K, μ (Cu Kα) = 0.963 mm<sup>−</sup>1, ρcalc = 1.432 g/cm3, F (000) = 332.0, R1 = 0.0296, wR2 =0.0745. Crystal dimensions 0.28 × 0.16 × 0.12 mm3. Flack parameter = 0.03(4). The total number of independent reflections measured was 12,512, of which 2626 were observed, collected in the range of 6.56◦ ≤ 2θ ≤ 145.682◦. The structure was determined and refined using full-matrix least-squares on F2 values for 1.109 I>=2σ (I).
