*4.4. Extraction and Isolation*

Strain 172205Δ*enc* spores were inoculated into seed broth medium, cultured at 200 rpm, 28 ◦C for 3 days. Then seed broth was transferred to 200 of 1 L flasks consisted of 300 mL fermentation medium, shaken at 200 rpm for 7 days (media recipes in literature [12]). The broth was extracted by organic reagent as described [9] and evaporated to dryness (80 g). Samples and fractions were tested by HPLC fingerprint [9]. HPLC fingerprints were carried using the following gradient: H2O (A)/MeOH (B): 0 min, 10% B; 15 min, 100% B; 20 min, 100% B; 21 min, 10% B; 30 min, 10% B; flow rate of 1 mL/min.

The crude extract was subjected to column chromatography on silica gel eluted by PE:CH2Cl2 (gradient from 1:0, 1:1 and 0:1, v:v) and CH2Cl2:MeOH (gradient from 100:1, 50:1, 5:1, 2:1 to methanol, v:v) to give A–F fractions. Importantly, the mix of crude extract and silica gel on column after elution was extracted by DMSO. DMSO layers were mixed with equal volume of NaCl saturated solution, and extracted again with ethyl acetate, then evaporated to fraction G. Fraction G was dissolved in DMSO and purified by HPLC (MeOH: H2O = 75:25, flow rate 3 mL/min) to afford compound **1** (4 mg, *tR* = 23.2 min). Fraction D was subject to silica gel column chromatography using cyclohexane: acetone (20:1 to 0:1 v:v) to afford five subfractions (D1–D5). Fraction D3 was purified by HPLC (MeCN: H2O = 30:70) to afford compound **2** (15 mg, *tR* = 16.9 min). Fraction D2 was purified by HPLC (MeOH: H2O = 48:52) to afford compound **3** (5 mg, *tR* = 30.7 min) and **4** (4 mg, *tR* = 31.9 min). Fraction D5 was purified by HPLC (MeCN: H2O = 20:80) to afford compound **5** (6 mg).

15*R*-17,18-dehydroxantholipin (**1**): dark red powder; [α] 20 <sup>D</sup> −168.85 (c 0.046, MeOH/CHCl3 = 5:1); UV (MeOH) λmax (log ε): 247 (4.34), 279 (4.23), 316 (4.08), 478 (3.80) nm; CD (c 0.041, CHCl3) λmax (Δε): 231 (−7.47), 249 (+5.09), 278 (−5.78), 314 (−1.29), 352 (−6.10), 485 (+1.41) nm; IR (KBr) υmax 3428, 2925, 1633, 1028 cm−1; 1H and 13C NMR data, see Table 1; positive ion HRESIMS *m*/*z* 534.0587 [M + H]<sup>+</sup> (calcd for C27H17ClNO9, 534.0586).

(*3E*,*5E*,*7E*)-3-methyldeca-3,5,7-triene-2,9-dione (**2**): yellow powder; UV (MeOH) λmax (log ε): 225 (3.80), 324 (4.96) nm; IR (KBr) υmax 3430, 2955, 2930, 1709, 1664, 1361, 1253, 998, 604 cm<sup>−</sup>1; 1H and 13C NMR data, see Table 1; positive ion HRESIMS *m*/*z* 179.1064 [M + H]<sup>+</sup> (calcd for C11H15O2, 179.1067).

Qinlactone A (**3**): colorless oil; [α] 19 <sup>D</sup> +31.55 (c 0.727, MeOH); UV (MeOH) λmax (log ε): 223 (4.07), 311 (4.40) nm; CD (c 0.013, MeOH) λmax (Δε): 200 (−0.6), 224 (+1.3), 316 (+0.4) nm; IR (KBr) υmax 3437, 2983, 2936, 1756, 1640, 1386, 1273, 1224, 1056, 995 cm<sup>−</sup>1; 1H and 13C NMR data, see Table 2; positive ion HRESIMS *m*/*z* 279.1587 [M + H]<sup>+</sup> (calcd for C16H23O4, 279.1591).

Qinlactone B (**4**): colorless oil; [α] 19 <sup>D</sup> −93.91 (c 0.553, MeOH); UV (MeOH) λmax (log ε): 221 (4.11), 313 (4.46) nm; CD (c 0.011, MeOH) λmax (Δε): 201 (+1.2), 225 (−2.9), 310 (−3.8) nm; IR (KBr) υmax 3432, 2980, 2934, 1774, 1758, 1716, 1640, 1386, 1274, 1225,1113, 1065, 996, 954 cm−1; 1H and 13C NMR data, see Table 2; positive ion HRESIMS *m*/*z* 279.1587 [M + H]<sup>+</sup> (calcd for C16H23O4, 279.1591).

Qinlactone C (**5**): light yellow oil; [α] 20 <sup>D</sup> −0.18 (c 0.552, MeOH); UV (MeOH) λmax (log ε): 201 (3.81), 229 (3.78), 275 (4.04) nm; CD (c 0.055, MeOH) λmax (Δε): 216 (−3.4), 270 (+0.4) nm; IR (KBr) υmax 3415, 3194, 2986, 2942, 1758, 1678, 1401, 1285, 1205, 1137, 1066, 954, 837, 801, 723 cm−1; 1H and 13C NMR data, see Table 2; positive ion HRESIMS *m*/*z* 313.1650 [M + H]<sup>+</sup> (calcd for C16H25O6, 313.1646).
