*3.4. Extraction and Isolation*

The entire culture was macerated and extracted with MeOH (1 L × 3 for each flask). The solvent was evaporated in vacuo to afford a brown organic extract (5.8 g). The extract was separated by C18 reversed-phase vacuum flash chromatography using sequential mixtures of H2O and MeOH (seven fractions of H2O-MeOH, gradient from 60:40 to 0:100), acetone, and finally, EtOAc as the eluents. Based on the results of 1H NMR analysis, the fractions eluted with H2O-MeOH 50:50 (550 mg), 40:60 (300 mg), and 20:80 (670 mg) were chosen for further separation. The fraction that eluted with H2O-MeOH (50:50) was separated by semi-preparative reversed-phase HPLC (YMC-ODS-A column, 250 × 10 mm, 5 μm; gradient from H2O-MeCN (90:10) to (50:50), 1.8 mL/min), to yield compound **9** (*t*<sup>R</sup> = 52.6 min). The H2O-MeOH (40:60) fraction from vacuum flash chromatography was separated by semi-preparative reversed-phase HPLC (H2O-MeCN, (80:20) to (30:70), 2.0 mL/min) to afford, in the order of elution, compounds **1** (*t*<sup>R</sup> = 44.8 min), **2** (*t*<sup>R</sup> = 45.4 min), **4** (*t*<sup>R</sup> = 50.8 min), **6** (*t*<sup>R</sup> = 51.4 min), **7** (*t*<sup>R</sup> = 59.4 min), and **8** (*t*<sup>R</sup> = 61.3 min). The H2O-MeOH (20:80) fraction from vacuum flash chromatography was separated by semi-preparative reversed-phase HPLC (H2O-MeCN, (65:35) to (25:75), 2.0 mL/min), affording compounds **3** (*t*<sup>R</sup> = 51.2 min) and **5** (*t*<sup>R</sup> = 40.6 min). The overall isolated amounts of 1–9 were 7.0, 3.0, 0.7, 3.0, 3.2, 3.2, 6.5, 8.2, and 2.8 mg, respectively.

Alterporriol Z1 (**1**): orange amorphous solid, [α] D <sup>25</sup> +1.8 (*c* 0.10, MeOH); UV (MeOH) λmax (log ε) 223 (3.97), 275 (3.86), 430 (3.36) nm; ECD (*c* 1.62 <sup>×</sup> 10−<sup>4</sup> M, MeOH) <sup>λ</sup>max (Δε), 220 (−4.02), 229 (−5.06), 269 (35.79), 285 (−36.06), 317 (−7.91) nm; IR (ZnSe) <sup>ν</sup>max 3544, 2970, 1622, 1593, 1372 cm<sup>−</sup>1; 1H and 13C NMR data, see Table 1; HRFABMS *m*/*z* 619.1449 [M + H]<sup>+</sup> (calcd for C32H27O13, 619.1446).

Alterporriol Z2 (**2**): orange amorphous solid, [α] D <sup>25</sup> −2.5 (*c* 0.10, MeOH); UV (MeOH) λmax (log ε) 227 (3.79), 274 (3.68), 432 (3.09) nm; ECD (*c* 1.62 <sup>×</sup> 10−<sup>4</sup> M, MeOH) <sup>λ</sup>max (Δε), 228 (6.18), 267 (−18.63), 284 (12.77), 317 (3.02) nm; IR (ZnSe) νmax 3412, 2973, 2938, 1638, 1580, 1397, 1293 cm−1; 1H and 13C NMR data, see Table 1; HRFABMS *m*/*z* 619.1454 [M + H]<sup>+</sup> (calcd for C32H27O13, 619.1446).

Alterporriol Z3 (**3**): dark red amorphous solid, [α] D <sup>25</sup> +13.5 (*c* 0.20, MeOH); UV (MeOH) λmax (log ε) 212 (3.83), 278 (3.70), 420 (3.27) nm; ECD (*c* 1.58 <sup>×</sup> 10−<sup>4</sup> M, MeOH) <sup>λ</sup>max (Δε), 218 (−18.94), 235 (8.44), 263 (15.31), 287 (−13.9) nm; IR (ZnSe) <sup>ν</sup>max 3416, 3120, 2973, 2931, 1638, 1605, 1322 cm−1; 1H and 13C NMR data, see Table 1; HRFABMS *m*/*z* 655.1430 [M + Na]<sup>+</sup> (calcd for C33H28O13Na, 655.1422).

Tricycloalterfurene E (**7**): brown amorphous solid, [α] D <sup>25</sup> +88.2 (*c* 0.20, MeOH); UV (MeOH) λmax (log ε) 220 (3.53), 262 (3.48) nm; ECD (*<sup>c</sup>* 2.65 <sup>×</sup> <sup>10</sup>−<sup>4</sup> M, MeOH) <sup>λ</sup>max (Δε), 258 (9.73), 313 (1.06) nm; IR (ZnSe) νmax 3546, 3347, 2930, 2854, 1748, 1610, 1538, 1371 cm<sup>−</sup>1; 1H and 13C NMR data, see Table 2; HRFABMS *m*/*z* 379.2118 [M + H]<sup>+</sup> (calcd for C21H31O6, 379.2115).

Tricycloalterfurene F (**8**): brown amorphous solid, [α] D <sup>25</sup> +74.0 (*c* 0.20, MeOH); UV (MeOH) λmax (log ε) 225 (3.42), 258 (3.35) nm; ECD (*<sup>c</sup>* 2.65 <sup>×</sup> <sup>10</sup>−<sup>4</sup> M, MeOH) <sup>λ</sup>max (Δε), 259 (8.39), 315 (0.17) nm; IR (ZnSe) νmax 3593, 3350, 2928, 2860, 1757, 1674, 1617, 1514, 1221 cm−1; 1H and 13C NMR data, see Table 2; HRFABMS *m*/*z* 379.2120 [M + H]<sup>+</sup> (calcd for C21H31O6, 379.2115).

Tricycloalterfurene G (**9**): brown amorphous solid, [α] D <sup>25</sup> +58.4 (*c* 0.20, MeOH); UV (MeOH) λmax (log ε) 211 (3.49) nm; ECD (*<sup>c</sup>* 2.55 <sup>×</sup> <sup>10</sup>−<sup>4</sup> M, MeOH) <sup>λ</sup>max (Δε), 258 (8.67), 315 (1.07) nm; IR (ZnSe) <sup>ν</sup>max 3603, 3356, 2933, 2860, 1742, 1602, 1536, 1371 cm−1; 1H and 13C NMR data, see Table 2; HRFABMS *m*/*z* 415.2104 [M + Na]<sup>+</sup> (calcd for C22H32O6Na, 415.2091).
