*3.2. Fungal Strain*

The strain of *A. flocculosus* was isolated from a sediment sample (Nha Trang Bay, South China Sea, Vietnam) and identified as described earlier [12]. The strain is stored at the collection of microorganisms of Nha Trang Institute of Technology and Research Application VAST (Nha Trang, Vietnam) under the code 01NT.1.12.3.

### *3.3. Cultivation of the Fungus*

The fungus was cultured at 28 ◦C for three weeks in 50 × 500 mL Erlenmeyer flasks, each containing rice (20.0 g), yeas<sup>t</sup> extract (20.0 mg), KH2PO4 (10 mg), and natural sea water from Nha Trang Bay (40 mL).

### *3.4. Extraction and Isolation*

The fungal mycelia of *A. flocculosus* with the medium were extracted for 24 h with 15 L of EtOAc. Evaporation of the solvent, under reduced pressure, gave a dark brown oil (5.0 g), to which 250 mL H2O–EtOH (4:1) was added, and the mixture was thoroughly stirred to yield a suspension. It was extracted, successively, with hexane (150 mL × 2), EtOAc (150 mL × 2), and n-BuOH (150 mL × 2). After evaporation of the EtOAc layer, the residual materials (3.36 g) were passed over a silica gel column (35.0 cm × 2.5 cm), which was eluted with a hexane–EtOAc gradient (1:0–0:1). The n-hexane–EtOAc (80:20, 1.3 g) fraction was purified by a Sephadex LH-20 column (80 cm × 2 cm, 50 g) with CHCl3 to yield compound **8** (245 mg). The n-hexane–EtOAc (75:25) fraction AF-1-64 (393 mg) was purified by HPLC on a YMC-SIL column eluting with CHCl3–MeOH–NH4OAc (97:3:1) to yield compounds **3** (220 mg) and **4** (11 mg). The n-hexane–EtOAc (75:25) fraction AF-1-67 (483 mg) was purified by HPLC on a YMC-SIL column eluting with CHCl3–MeOH–NH4OAc (97:3:1) to yield compounds **5** (5.9 mg), **7** (9.0 mg), and **10** (3.1 mg). The n-hexane–EtOAc (75:25) fraction AF-1-88 (68.3 mg) was purified by HPLC on a YMC-SIL column eluting with CHCl3–MeOH–NH4OAc (97:3:1) to yield compounds **1** (2.9 mg) and **2** (3.8 mg). The n-hexane–EtOAc (70:30) fraction AF-1-93 (784 mg) was purified by HPLC first on a YMC-SIL column eluting with CHCl3–MeOH–NH4OAc (97:3:1) and then on a YMC ODS-AM column, eluting with MeOH–H2O (55:45) to yield compound **9** (5.5 mg). The n-hexane–EtOAc (60:40, 282 mg) fraction was purified by Sephadex LH-20 column (80 cm × 2 cm, 50 g) with CHCl3-EtOH (3:1) to yield compound **6** (68 mg).

Aspilactonol F (**1**): white powder; [α]20D +98 (*c* 0.20, MeOH); UV (MeOH) λmax (log ε) 214 (4.03) nm; ECD (0.9 mM, MeOH) λmax (Δε) 217 (+11.35) nm; 1H and 13C NMR data see Table 1, Figures S1–S7; HR ESIMS *m*/*z* 209.0785 [M + Na]+ (calcd. for C9H14O4Na, 209.0784, Δ −0.1 ppm).

Aspilactonol G (**2**): white powder; [α]20D –49 (*c* 0.49, MeOH); UV (MeOH) λmax (log ε) 214 (4.05) nm; ECD (1.1 mM, MeOH) λmax (Δε) 216 (–11.51) nm; 1H and 13C NMR data see Table 1, Figures S9–S16; HRESIMS *m*/*z* 209.0782 [M + Na]+ (calcd. for C9H14O4Na, 209.0784, Δ +1.1 ppm).

12-*Epi*-aspertetranone D (**4**): white powder; [α]20D +78 (*c* 0.07, MeOH); UV (MeOH) λmax (log ε) 290 (3.93), 208 (4.53) nm; ECD (0.5 mM, MeOH) λmax (Δε) 209 (+25.54), 284 (+1.86) nm; 1H and 13C NMR data see Table 2, Figures S20–S26; HRESIMS *m*/*z* 459.1628 [M + Na]+ (calcd. for C22H28O9Na, 459.1626, Δ −0.2 ppm).

6β,9<sup>α</sup>,14-trihydroxycinnamolide (**7**): white crystals; [α]20D –7.3 (*c* 0.15, MeOH); UV (MeOH) λmax (log ε) 206 (3.61) nm; ECD (2.8 mM, MeOH) λmax (Δε) 224 (–2.33) nm; 1H and 13C NMR data see Table 3, Figures S30–S36; HRESIMS *m*/*z* 305.1361 [M + Na]+ (calcd. for C15H22O5Na, 305.1359, Δ −0.5 ppm).

6β,7β,14-trihydroxyconfertifolin (**9**)*:* white crystals; [α]20D +93.5 (*c* 0.36, MeOH); UV (MeOH) λmax (log ε) 214 (4.00) nm; ECD (1.1 mM, MeOH) λmax (Δε) 217 (+3.68), 243 (+1.51) nm; 1H and 13C NMR data see Table 3, Figures S39–S47; HRESIMS *m*/*z* 305.1361 [M + Na]+ (calcd. for C15H22O5Na, 305.1359, Δ −0.5 ppm).

### *3.5. Preparation of (S)-MTPA and (R)-MTPA Esters of Aspilactonol F (1)*

The compounds 4-dimethylaminopyridine (a few crystals) and (*R*)-MTPA-Cl (4 μL) were added to a solution of **1** (1.0 mg) in pyridine at room temperature and stirred for 5 h. After evaporation of the solvent, the residue was purified by HPLC on a YMC SIL column (EtOAc–hexane, 20:80) to afford the (*S*)-MTPA ester (0.5 mg). The (*R*)-MTPA ester (0.5 mg) was prepared in a similar manner using (*S*)-MTPA-Cl.

(*S*)-MTPA ester of **1**: 1H NMR (CDCl3, 500.13 MHz) δ: 6.88 (1H, brs, H-4), 5.28-5.34 (2H, m, H-6, H-9), 4.84 (1H, dd, *J* = 3.9; 1.7 Hz, H-5), 3.48 (3H, s, OMe), 3.43 (3H, s, OMe), 2.56-2.60 (2H, m, H2-8), 1.26 (3H, d, *J* = 6.5 Hz, Me-7), 1.24 (3H, d, *J* = 6.3 Hz, Me-10), 7.39–7.48 (10H, m, 2Ph). HRESIMS *m*/*z* 641.1576 [M + Na]+ (calcd for C29H28F6Na, 641.1581, Δ = 0.8 ppm).

(*R*)-MTPA ester of **1**: 1H NMR (CDCl3, 500.13 MHz) δ: 6.52 (1H, brs, H-4), 5.25 (1H, m, H-9), 5.20 (1H, dd, *J* = 6.6, 4.3 Hz, H-6), 4.56 (1H, dd, *J* = 4.3, 1.6 Hz, Hz, H-5), 3.56 (3H, s, OMe), 3.50 (3H, s, OMe), 2.48-2.51 (2H, m, H2-8), 1.35 (3H, d, *J* = 6.2 Hz, Me-10), 1.29 (3H, d, *J* = 6.6 Hz, Me-7), 7.38–7.52 (10H, m, 2Ph). HRESIMS *m*/*z* 641.1577 [M + Na]+ (calcd for C29H28F6Na, 641.1581, Δ = 0.6 ppm).

### *3.6. Preparation of (S)-MTPA and (R)-MTPA Esters of Aspilactonol G (2)*

(*R*)-MTPA-Cl (9 μL) was added to a solution of **2** (1.9 mg) in pyridine at room temperature and stirred for 2 h. After evaporation of the solvent, the residue was purified by HPLC on a YMC SIL column (acetone–hexane, 25:75) to afford the (*S*)-MTPA ester (1.4 mg). The (*R*)-MTPA ester (1.5 mg) was prepared in a similar manner using (*S*)-MTPA-Cl.

(*S*)-MTPA ester of **2**: 1H NMR (CDCl3, 700 MHz) δ: 6.86 (1H, brs, H-4), 5.32 (1H, m, H-9), 5.23 (1H, m, H-6), 4.81 (1H, brd, *J* = 5.0 Hz, H-5), 3.52 (3H, s, OMe), 3.47 (3H, s, OMe), 2.65 (1H, dd, *J* = 15.8; 6.9, H-8), 2.48 (1H, ddt, *J* = 15.9; 5.0; 1.5, H-8), 1.39 (3H, d, *J* = 6.5 Hz, Me-7), 1.29 (3H, d, *J* = 6.2 Hz, Me-10), 7.38–7.50 (10H, m, 2Ph). HRESIMS *m*/*z* 641.1576 [M + Na]+ (calcd for C29H28F6Na, 641.1581, Δ = 0.8 ppm).

(*R*)-MTPA ester of **2**: 1H NMR (CDCl3, 700 MHz) δ: 6.68 (1H, brs, H-4), 5.30 (1H, m, H-9), 5.26 (1H, m, H-6), 4.82 (1H, m, Hz, H-5), 3.53 (3H, s, OMe), 3.48 (3H, s, OMe), 2.61 (1H, dd, *J* = 15.9; 7.2, H-8), 2.46 (1H, dd, *J* = 15.9; 4.7, H-8), 1.33 (3H, d, *J* = 6.3 Hz, Me-10), 1.25 (3H, d, *J* = 6.7 Hz, Me-7), 7.37–7.52 (10H, m, 2Ph). HRESIMS *m*/*z* 641.1576 [M + Na]+ (calcd for C29H28F6Na, 641.1581, Δ = 0.8 ppm).
