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Supplementary Materials Figure S1. Chemical structures of phloracetophenone intermediates (2a, 2c 2g). 2a 2c 2d 2e 2f 2g Figure S2. Chemical structures of geranylacetophenone analogues (3a, 3c, 3e g). 3a 3c 3e 3f 3g 2-Methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one (2a). Light yellow solid, yield 6.75%. 1 H-NMR (5 MHz, -d 4 ) d 5.81 (s, 2H), 3.97 (td, J = 6.82, 11 Hz, 1H), 1.13 (d, J = 6.6 Hz, 6H). 13 C-NMR (126 MHz, -d 4 ) 21.3, 164.2, 164., 13.2, 94.5, 38.5, 18.3. DIP: m/z 196.5.

13.21 21.26 164.42 48.12 47.95 47.78 47.1 47.27 47.44 47.61 38.51 94.45 18.26 3.96 3.97 3.98 5.81 1.12 1.13 Molecules 214, 19 S2 Figure S3. 1 H-NMR spectrum of 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one. i16bnew_1h 4. H 3. 2. 1..5 2. 1.18 6.58 6. 5.5 5. 4.5 4. 3. 2. 1..5 Figure S4. 13 C-NMR spectrum of 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one. i16bnew_13c 5. 4.5 4. H 3. 2. 1..5 22 2 18 16 14 12 1 8 6 4 2-2 Figure S5. Mass spectrum of 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one.

13.84 26.49 164.33 164.45 48.1 47.93 47.8 47.25 36.52 7.77 94.3 47.42 47.59 47.76 3.8 3.6 3.7 3.4 3.4 1.11 1.11 1.14 1.14 5.8 5.81 1.12 1.13 Molecules 214, 19 S3 1-(2,4,6-Trihydroxyphenyl)propan-1-one (2c). Light brown solid, yield 2.81%. 1 H-NMR (5 MHz, -d 4 ) d 5.8 (s, 2H), 3.4 3.7 (m, 2H), 1.12 (dt, J = 1.47, 7.21 Hz, 3H). 13 C-NMR (126 MHz, -d 4 ) 26.5, 164.5, 164.3, 13.8, 94.4, 36.5, 7.8. DIP: m/z 18. Figure S6. 1 H-NMR spectrum of 1-(2,4,6-trihydroxyphenyl)propan-1-one. i13bnew_1h 6. 5.5 5. H 4.5 4. 3. 2. 1..5 2. 2.42 1 7. 6.5 6. 5.5 5. 4.5 4. 3. 2. 1. Figure S7. 13 C-NMR spectrum of 1-(2,4,6-trihydroxyphenyl)propan-1-one. i13bnew_13c H 2. 1..5 22 2 18 16 14 12 1 8 6 4 2-2 Figure S8. Mass spectum of 1-(2,4,6-trihydroxyphenyl)propan-1-one.

19.54 216.36 155.55 159.2 48.11 93.87 44.6 47.8 47.25 47.94 47.42 47.6 47.77 26.11 5.83 1.21 Molecules 214, 19 S4 2,2-Dimethyl-1-(2,4,6-trihydroxyphenyl)propane-1-one (2d). Dark brown solid, yield.75%. 1 H-NMR (5 MHz, -d 4 ) d 5.83 (s, 2H), 1.21 (s, 9H). 13 C-NMR (126 MHz, -d 4 ) 216.4, 159., 155.6, 19.5, 93.9, 44.6, 26.1. DIP: m/z 2. Figure S9. 1 H-NMR spectrum of 2,2-dimethyl-1-(2,4,6-trihydroxyphenyl)-propane-1-one. i11dnew_1h 3. H 2. 1..5 2. 1.75 6. 5.5 5. 4.5 4. 3. 2. 1..5 Figure S1. 13 C-NMR spectrum of 2,2-dimethyl-1-(2,4,6-trihydroxyphenyl)-propane-1-one. i11dnew_13c H 2. 1..5 22 2 18 16 14 12 1 8 6 4 2-2 Figure S11. Mass spectrum of 2,2-dimethyl-1-(2,4,6-trihydroxyphenyl)-propane-1-one.

.92.95.94 Molecules 214, 19 164.37 13.98 48.11 26.17 164.53 47.94 22.27 27. 12.87 94.35 47.6 47.77 3.31 3.31 3.4 3.1 1.39 1.62 1.63 1.65 3.3 5.8 5.81 S5 1-(2,4,6-Trihydroxyphenyl)pentan-1-one (2e). Light yellow solid, yield 1%. 1 H-NMR (5 MHz, -d 4 ) d 5.8 (s, 2H), 3.3 (t, J = 7.46 Hz, 2H), 1.63 (quin, J = 7.46 Hz, 2H), 1.38 (sxt, J = 7.39 Hz, 2H),.94 (t, 3H). 13 C-NMR (126 MHz, -d 4 ) 26.2, 164.5, 164.4, 14., 94.4, 43.1, 27., 22.3, 12.9. DIP: m/z 21.1. Figure S12. 1 H-NMR spectrum of 1-(2,4,6-trihydroxyphenyl)pentan-1-one. i14dnew_1h 6. 5.5 5. H 4.5 4. 3. 2. 1.36 1.38 1..5 2. 2.13 2.47 9 3.42 6.5 6. 5.5 5. 4.5 4. 3. 2. 1..5 Figure S13. 13 C-NMR spectrum of 1-(2,4,6-trihydroxyphenyl)pentan-1-one. 5. 4.5 4. i14dnew_13c H 43.11 47.43 3. 2. 1..5 22 2 18 16 14 12 1 8 6 4 2-2 Figure S14. Mass spectrum of 1-(2,4,6-trihydroxyphenyl)pentan-1-one.

13.44 47.31 29.4 164.3 47.48 47.65 49.19 94.54 29.31 25.9 3.71 3.71 3.69 3.69 3.67 3.68 1.68 1.7 1.77 1.78 1.79 1.8 1.87 1.89 1.41 1.39 1.3 1.33 1.35 1.37 1.25 1.24 1.21 5.81 Molecules 214, 19 S6 Cyclohexyl(2,4,6-trihydroxyphenyl)methanone (2f). range brown solid, yield 14.15%. 1 H-NMR (5 MHz, -d 4 ) d 5.81 (s, 2H), 3.67 3.71 (m, 1H), 1.89 (br. s., 2H), 1.78 (dd, J = 2.69, 9.5 Hz, 2H), 1.69 (d, J = 12.47 Hz, 1H), 1.3 1.41 (m, 5H), 1.21 1.25 (m, 1H). 13 C-NMR (126 MHz, -d 4 ) 29.4, 165.4, 164.3, 13.44, 94.54, 49.19, 29.31, 25.94, 25.9. DIP: m/z 236.1. Figure S15. 1 H-NMR spectrum of cyclohexyl(2,4,6-trihydroxyphenyl)methanone. I12CNEW_1H 3. H 2. 1..5 2.1 1.6 2 2.37 1.26 5.25 1.27 6.5 6. 5.5 5. 4.5 4. 3. 2. 1..5 Figure S16. 13 C-NMR spectrum of cyclohexyl(2,4,6-trihydroxyphenyl)methanone. i12cnew_13c H 2. 1..5 22 2 18 16 14 12 1 8 6 4 2-2 Figure S17. Mass spectrum of cyclohexyl(2,4,6-trihydroxyphenyl)methanone.

198 164.7 165.16 135.65 14.53 141.42 129.64 94.61 128.54 48.1 47.93 47.8 47.25 47.42 47.59 47.76 7.42 7.37 8.19 8.23 7.73 7.62 7.61 7.4 7.39 5.86 Molecules 214, 19 S7 (E)-3-Phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one (2g). range solid, yield 9.1%. 1 H-NMR (5 MHz, -d 4 ) d 8.23 (d, J = 15.65 Hz, 1H), 7.73 (d, J = 15.65 Hz, 1H), 7.62 (d, J = 6.6 Hz, 2H), 7.37 7.42 (m, 4H), 5.86 (s, 2H). 13 C-NMR (126 MHz, -d 44 ) 192.6, 165.2, 164.7, 141.4, 135.7, 129.6, 128.5, 128., 127.9, 127.5, 14.5, 94.6. DIP: m/z 256.5. Figure S18. 1 H-NMR spectrum of (E)-3-phenyl-1-(2,4,6-trihydroxyphenyl)- prop-2-en-1-one. i172dnew_1h 6. 5.5 5. 4.5 4. H 3. 2. 1..5 1.29 1.25 2.353.88 2. 8.5 8. 7.5 7. 6.5 6. 5.5 5. 4.5 4. 3. Figure S19. 13 C-NMR spectrum of (E)-3-phenyl-1-(2,4,6-trihydroxyphenyl)- prop-2-en-1-one. i172dnew_13c H 2. 1. 127.52 127.87.5 22 2 18 16 14 12 1 8 6 4 2-2 Figure S2. Mass spectrum of (E)-3-phenyl-1-(2,4,6-trihydroxyphenyl)- prop-2-en-1-one.

211.75 16 163.45 165.35 131.97 134.67 14.55 18.22 124.72 125.55 95. 16.23 39.93 4.95 25.87 27.75 19.84 48.52 48.69 48.86 49.3 49.2 49.37 49.54 5.4 5.16 3.98 1.28 5.88 5.88 1.93 2.3 3.17 4 4 9 1.72 1.73 1.13 1.11 1.11 1.12 Molecules 214, 19 S8 3-Geranyl-1-(2 -methylpropanoyl)phloroglucinol (3a). range brown solid, yield 19.5%. 1 H-NMR (5 MHz, -d 4 ) d 5.88 (s, 1H), 5.13 5.19 (m, 1H), 5. 5.8 (m, 1H), 3.94 4.3 (m, 1H), 3.17 (br. s., 2H), 2.3 (br. s., 2H), 1.93 (br. s., 2H), 1.73 (s, 3H), 9 (br. s., 3H), 4 (s, 3H), 1.12 (dd, J = 3.64, 6.55 Hz, 6H). 13 C-NMR (126 MHz, -d 4 ) 211.8, 165.4, 16, 161.1, 134.7, 132., 125.6, 124.7, 18.2, 14.6, 95., 41., 39.9, 27.8, 25.9, 22.2, 19.8, 17.7, 16.2. DIP: m/z 332.1. Figure S21. 1 H-NMR spectrum of 3-geranyl-1-(2'-methylpropanoyl)phloroglucinol. c5redo_1h_2nd.9.8.7.6 H.5.4.3.2.1.96 1.31 1. 1.32 3.8 7 2.87 3.86 3.76 1 9.47 7. 6.5 6. 5.5 5. 4.5 4. 3. 2. 1..5 Figure S22. 13 C-NMR spectrum of 3-geranyl-1-(2 -methylpropanoyl)phloroglucinol. c5redo_13c.65.6.55.5.45 H.4.35.3.25.2.15.1.5 22 2 18 16 14 12 1 8 6 4 2 Figure S23. Mass spectrum of 3-geranyl-1-(2 -methylpropanoyl)phloroglucinol.

26.51 5.89 159.98 162.6 163.42 163.43 5.5 5.17 12 133.25 123.24 124.9 13.68 16.59 93.38 3.7 3.17 3.19 3.4 47.6 47.23 47.4 47.57 47.74 47.91 48.8 48.2 1.92 1.93 1.95 2.3 47.4 39.5 36.59 26.31 24.4 1.73 2.65 16.26 5 1.6 14.76 7.97 1.29 1.14 1.11 1.13 Molecules 214, 19 S9 (E)-1-(3-(3,7-Dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)propan-1-one (3c). Yellowish brown solid, yield 6.9%. 1 H-NMR (5 MHz, -d 4 ) d 5.89 (s, 1H), 5.16 5.23 (m, 1H), 5.6 5.1 (m, 1H), 3.17 (d, J = 7.9 Hz, 2H), 3.4-3.7 (m, 2H), 1.95 (m, 2H), 1.92 (d, J = 7.83 Hz, 2H), 1.73 (s, 3H), 1.6 (s, 3H), 5 (s, 3H), 1.13 (t, J = 7.21 Hz, 3H). 13 C-NMR (126 MHz, -d 4 ) 26.5, 163.4, 162.1, 16., 133.3, 1, 124.1, 123.2, 16.6, 13.7, 93.4, 39.5, 36.6, 26.3, 24.4, 2.7, 16.3, 14.8, 8.. DIP: m/z 318.2. Figure S24. 1 H-NMR spectrum of (E)-1-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-propan-1-one. c6_1h_2nd.55.5.45.4 H.35.3.25.2.15.1.5.38 1..87 2.14 2.36 2. 2.27 3.24 3.21 2.74 3.34 6.5 6. 5.5 5. 4.5 4. 3. 2. 1. Figure S25. 13 C-NMR spectrum of (E)-1-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-propan-1-one. c6_13c.15 H.1.5 22 2 18 16 14 12 1 8 6 4 2-2 Figure S26. Mass spectrum of (E)-1-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-propan-1-one.

161 156.76 26.31 48.23 133.34 123.19 13.61 2.65 124.6 43.22 27.23 16.3 39.47 26.27 14.79 24.43 47.1 47.27 47.44 47.61 47.78 47.95 48.12 22.32 12.91 5.9 5.16 5.4 3.1 2.4 2.3 1.94 1.91 1.41 1.36 1.39 1.38 3.18 3.17 3.3 1.93.95.92.94 1.73 1.6 4 Molecules 214, 19 S1 (E)-1-(3-(3,7-Dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)pentan-1-one (3e). Yellowish brown solid, yield 1.3%. 1 H-NMR (5 MHz, -d 4 ) d 5.9 (s, 1H), 5.13 5.19 (m, 1H), 5.4 (br. s., 1H), 3.17 (d, J = 6.85 Hz, 2H), 3.3 (t, J = 1. Hz, 2H), 2.3 2.4 (m, 2H), 1.91 1.94 (m, 2H), 1.73 (s, 3H), 1.61 1.67 (m, 2H), 1.6 (s, 3H), 4 (s, 3H), 1.38 1.41 (m, 2H),.94 (t, J = 7.34 Hz, 3H). 13 C-NMR (126 MHz, -d 4 ) 26.3, 16, 156.8, 133.3, 13.6, 124.1, 123.2, 43.2, 39.5, 27.2, 26.3, 24.4, 22.3, 2.7, 16.3, 14.8, 12.9. DIP: m/z 346.2. Figure S27. 1 H-NMR spectrum of (E)-1-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)pentan-1-one. c3reisolate_1h_2nd.6.5 H.4.3.2.1.43 1..74 2.34 2.35 2.11 2.35 3.37 2.31 2.95 2.22 7 6.5 6. 5.5 5. 4.5 4. 3. 2. 1..5 Figure S28. 13 C-NMR spectrum of (E)-1-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)pentan-1-one. c3reisolate_13c.3.25 H.2.15.1.5 22 2 18 16 14 12 1 8 6 4 2-2 Figure S29. Mass spectrum of (E)-1-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)pentan-1-one.

29.35 159.62 161.92 163.92 13.24 16.77 12 133.22 96 2.7 123.26 124.9 14.76 16.27 49.19 39.49 48.8 47.91 47.74 47.57 47.4 47.23 47.6 29.41 5.5 5.17 3.72 1.27 1.29 5.88 3.17 3.18 1.38 1.41 5 1.6 1.73 1.79 1.88 1.93 1.95 2.3 Molecules 214, 19 S11 (E)-Cyclohexyl (3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-methanone (3f). Brown solid, yield 5.7%. 1 H-NMR (5 MHz, -d 4 ) d 5.89 (s, 1H), 5.14 5.2 (m, 1H), 5.2 5.8 (m, 1H), 3.68 3.76 (m, 1H), 3.17 (d, J = 7.9 Hz, 2H), 2.4 (d, J = 7.34 Hz, 2H), 1.86 1.97 (m, 4H), 1.8 (d, J = 11. Hz, 2H), 1.73 (s, 3H), 1.6 (s, 3H), 5 (s, 3H), 1.31 1.44 (m, 4H), 1.23 1.3 (m, 2H). 13 C-NMR (126 MHz, -d 4 ) 29.4, 163.9, 161.9, 159.6, 133.2, 1, 124.1, 123.3, 16.8, 13.2, 93.6, 49.2, 39.5, 29.4, 26.3, 26., 25.9, 24.4, 2.7, 16.3, 14.8. DIP: m/z 37. Figure S3. 1 H-NMR spectrum of (E)-cyclohexyl (3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)- methanone. c2reisolate_1h_2nd.55.5.45 H.4.35.3.25.2.15 1.34 1.36.1.5.55 1..85 1.7 2.41 1.94 4.48 2.41 3.82 2.84 2 5.69 1.44 6.5 6. 5.5 5. 4.5 4. 3. 2. 1..5 Figure S31. 13 C-NMR spectrum of (E)-cyclohexyl (3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)- methanone. c2reisolate_13c 24.41 25.94.2 H.15.1.5 22 2 18 16 14 12 1 8 6 4 2-2 Figure S32. Mass spectrum of (E)-cyclohexyl (3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)- methanone.

128.43 195.75 16.91 16 165.23 18.54 11.68 139.2 48.2 42.9 133.78 78.95 94.26 2.39 128 124.5 14.78 16.28 24.42 39.49 26.31 125.88 128.25 47.7 47.24 47.41 47.58 47.75 47.92 48.9 5.43 5.42 5.41 5.2 5.6 4.59 3.6 2.75 2.74 7.39 7.37 7.36 2.6 1.96 1.29 5.97 3.23 3.21 1.95 1.62 6 1.75 3.31 3.31. Molecules 214, 19 S12 (E)-1-(3-((E)-3,7-Dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-3-phenylprop-2-en-1-one (3g). Light yellow solid, yield 11.7%. 1 H-NMR (5 MHz, -d 4 ) d 7.48-7.5 (m, 2H), 7.39-7.43 (m, 2H), 7.34 7.38 (m, 1H), 5.97 (s, 1H), 5.17 5.22 (m, 1H), 5.4 5.8 (m, 1H), 3.23 (d, J = 1. Hz, 2H), 3.3 3.11 (m, 1H), 2.73 2.79 (m, 1H), 2.2 2.8 (m, 2H), 1.92 1.98 (m, 2H), 1.75 (s, 3H), 1.62 (s, 3H), 6 (s, 3H). 13 C-NMR (126 MHz, -d 4 ) 195.8, 165.2, 161.1, 16.9, 139.2, 133.8, 13.6, 128.4, 128.2, 128.1, 125.9, 124.1, 122.6, 18.5, 11.7, 94.3, 78.9, 42.9, 39.5, 26.3, 24.4, 2.4, 16.3, 14.8. DIP: m/z 392.2. Figure S33. 1 H-NMR spectrum of (E)-1-(3-((E)-3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-3-phenylprop2-en-1-one. c4reisolate_1h_2nd.6.5 H.4.3.2 7.5 7.48 7.41.1 2.2 2.7.94.69 1.11.86 2.11.821.2 2.19 2.4 3.17 2.88 8 7 6 5 4 3 2 1 Figure S34. 13 C-NMR spectrum of (E)-1-(3-((E)-3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-3-phenylprop2-en-1-one. c4reisolate_13c.25.2 H.15.1.5 2 18 16 14 12 1 8 6 4 2 Figure S35. Mass spectrum of (E)-1-(3-((E)-3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)-3-phenylprop2-en-1-one.

Molecules 214, 19 S13 Figure S36. Three-dimensional (3-D) docking model of binding interaction of the compound 3g with amino acid residues; the atom colouring for the compounds is the following: carbons in grey, oxygen in red, hydrogen in white and amino acid in green color. The green line indicates the hydrogen-bonding interactions. Figure S37. Three-dimensional (3-D) docking model of the superimposed structures of the active compound 3g with the most active compound 3e and also the (9Z,11E)-13(R)-hydroperoxy-9,11-octadecadienoic acid (13-HPD) as LX substrate. The blue color represents compound 3g, red color represents compound 3e, while yellow sticks represents 13-HPD. Figure S38. Three-dimensional (3-D) docking model of binding interaction of the NDGA with amino acid residues; the atom colouring for the compounds is the following: carbons in grey, oxygen in red, hydrogen in white and amino acid in green color. The orange line indicates the π-interaction.

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