Hawaiienols A D, Highly Oxygenated p-terphenyls from an. Insect-Associated Fungus Paraconiothyrium hawaiiense
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1 Hawaiienols A D, Highly Oxygenated p-terphenyls from an Insect-Associated Fungus Paraconiothyrium hawaiiense Fengxia Ren,, Shenxi Chen,, Yang Zhang, Shuaiming Zhu, Junhai Xiao, Xingzhong Liu, Ruibin Su,*, and Yongsheng Che*, State Key Laboratory of Toxicology & Medical Countermeasures, Beijing Institute of Pharmacology & Toxicology, Beijing , People s Republic of China State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing , People s Republic of China State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin , People s Republic of China Contents 1) Figure S1. 2) Figure S2. 1 H NMR spectrum of hawaiienol A (1; 600 MHz, acetone-d 6 ) 3 13 C NMR spectrum of hawaiienol A (1; 150 MHz, acetone-d 6 ) 4 Page 3) Figure S3. HSQC spectrum of hawaiienol A (1; 600 MHz, acetone-d 6 ) 5 4) Figure S4. 1 H 1 H COSY spectrum of hawaiienol A (1; 600 MHz, acetone-d 6 ) 6 5) Figure S5. HMBC spectrum of hawaiienol A (1; 600 MHz, acetone-d 6 ) 7 6) Figure S6. NOESY spectrum of hawaiienol A (1; 600 MHz, acetone-d 6 ) 8 7) Figure S7. 8) Figure S8. 1 H NMR spectrum of hawaiienol B (2; 600 MHz, acetone-d 6 ) 9 13 C NMR spectrum of hawaiienol B (2; 150 MHz, acetone-d 6 ) 10 9) Figure S9. HSQC spectrum of hawaiienol B (2; 600 MHz, acetone-d 6 ) 11 10) Figure S10. 1 H 1 H COSY spectrum of hawaiienol B (2; 600 MHz, acetone-d 6 ) 12 11) Figure S11. HMBC spectrum of hawaiienol B (2; 600 MHz, acetone-d 6 ) 13 12) Figure S12. NOESY spectrum of hawaiienol B (2; 600 MHz, acetone-d 6 ) 14 13) Figure S13. 14) Figure S14. 1 H NMR spectrum of hawaiienol C (3; 600 MHz, acetone-d 6 ) C NMR spectrum of hawaiienol C (3; 150 MHz, acetone-d 6 ) 16 15) Figure S15. HSQC spectrum of hawaiienol C (3; 600 MHz, acetone-d 6 ) 17 16) Figure S16. 1 H 1 H COSY spectrum of hawaiienol C (3; 600 MHz, acetone-d 6 ) 18 17) Figure S17. HMBC spectrum of hawaiienol C (3; 600 MHz, acetone-d 6 ) 19 1
2 18) Figure S18. NOESY spectrum of hawaiienol C (3; 600 MHz, acetone-d 6 ) 20 19) Figure S19. 20) Figure S20. 1 H NMR spectrum of hawaiienol D (4; 600 MHz, acetone-d 6 ) C NMR spectrum of hawaiienol D (4; 150 MHz, acetone-d 6 ) 22 21) Figure S21. HSQC spectrum of hawaiienol D (4; 600 MHz, acetone-d 6 ) 23 22) Figure S22. 1 H 1 H COSY spectrum of hawaiienol D (4; 600 MHz, acetone-d 6 ) 24 23) Figure S23. HMBC spectrum of hawaiienol D (4; 600 MHz, acetone-d 6 ) 25 24) Figure S24. NOESY spectrum of hawaiienol D (4; 600 MHz, acetone-d 6 ) 26 25) Figure S25. Experimental CD spectrum of 1 in MeOH 27 26) Figure S26. Relative configurations of 2 (the enantiomers were not shown) 28 27) Figure S27. Relative configurations of 4 (the enantiomers were not shown) 29 28) Figure S28. The optimized conformers for ) Figure S29. The optimized conformers for ) Figure S30. The optimized conformers for ) Figure S31. The optimized conformers for 3a 37 32) Figure S32. Experimental CD spectrum of 2 in MeOH and the calculated ECD spectra of 2a 2h and 2a 2h 38 33) Figure S33. Experimental CD spectrum of 4 in MeOH and the calculated ECD spectra of 4a 4p and 4a 4p 39 34) Figure S34. Linear regression fitted 13 C NMR chemical shifts of 4 with four sets of experimental values (4i, 4l, 4n, and 4o) 40 35) Table S1. The experimental and computed 13 C NMR data of ) Table S2. Statistics of Ordinary Least Squares (OLS) Linear Regression of the experimental and computed 13 C NMR chemical shifts of ) Table S3. The experimental and computed 13 C NMR data of ) Table S4. Statistics of Ordinary Least Squares (OLS) Linear Regression of the experimental and computed 13 C NMR chemical shifts of ) Scheme S1. Plausible biosynthetic pathways for Contributed equally to this work. * Corresponding authors. 2
3 Figure S1. 1 H NMR Spectrum of Hawaiienol A (1; 600 MHz, Acetone-d 6 ) 3
4 Figure S2. 13 C NMR Spectrum of Hawaiienol A (1; 150 MHz, Acetone-d 6 ) 4
5 Figure S3. HSQC Spectrum of Hawaiienol A (1; 600 MHz, Acetone-d 6 ) 4-OCH 3 3 -OCH 3 H-2,6 H-2,6 H-3,5 H-3,5 H-6 H-5 H-2 3 -OCH 3 4-OCH 3 C-2 C-6 C-5 C-3,5 C-3,5 C-2,6 C-2,6 5
6 Figure S4. 1 H 1 H COSY Spectrum of Hawaiienol A (1; 600 MHz, Acetone-d 6 ) H-2,6 H-2,6 H-3,5 H-3,5 H-6 H-5 H-2 OH-2 OH-2 H-2 H-5 H-6 H-3,5 H-3,5 H-2,6 H-2,6 6
7 Figure S5. HMBC Spectrum of Hawaiienol A (1; 600 MHz, Acetone-d 6 ) 4-OCH 3 3 -OCH 3 OH-4 H-2,6 H-2,6 H-3,5 H-3,5 H-6 H-5 OH-4 H-2 OH-2 3 -OCH 3 4-OCH 3 C-2 C-4,6 C-5 C-1 C-3,5 C-3,5 C-1,2,6 C-2,6,1 C-3 C-4 C-4 7
8 Figure S6. NOESY Spectrum of Hawaiienol A (1; 600 MHz, Acetone-d 6 ) 4-OCH 3 3 -OCH 3 OH-4 H-2,6 H-2,6 H-3,5 H-6 OH-4 H-3,5 H-5 H-2 OH-2 OH-2 3 -OCH 3 4-OCH 3 OH-4 H-2 H-5 H-6 H-3,5 H-3,5 H-2,6 H-2,6 OH-4 8
9 Figure S7. 1 H NMR Spectrum of Hawaiienol B (2; 600 MHz, Acetone-d 6 ) 9
10 Figure S8. 13 C NMR Spectrum of Hawaiienol B (2; 150 MHz, Acetone-d 6 ) 10
11 Figure S9. HSQC Spectrum of Hawaiienol B (2; 600 MHz, Acetone-d 6 ) 4-OCH 3,4 -OCH 3 3 -OCH 3 H-2,6 H-3,5,3,5 H-2,6 H-6 H-5 3 -OCH 3 4-OCH 3,4 -OCH 3 C-6 C-5 C-3,5 C-3,5 C-2,6 C-2,6 11
12 Figure S10. 1 H 1 H COSY Spectrum of Hawaiienol B (2; 600 MHz, Acetone-d 6 ) 4-OCH 3,4 -OCH 3 3 -OCH 3 H-2,6 H-2,6 H-3,5,3,5 H-6 H-5 OH-5 3 -OCH 3 4-OCH 3,4 -OCH 3 OH-5 H-5 H-6 H-3,5,3,5 H-2,6 H-2,6 12
13 Figure S11. HMBC Spectrum of Hawaiienol B (2; 600 MHz, Acetone-d 6 ) 4-OCH 3,4 -OCH 3 3 -OCH 3 H-2,6 H-2,6 H-3,5,3,5 OH-1 or4 H-6 H-5 OH-1 or4 OH-5 3 -OCH 3 4-OCH 3,4 -OCH 3 C-4 C-6,1 C-5 C-3,5,3,5,3 C-2,6,1,1,2,6 C-4,4 C-2 13
14 Figure S12. NOESY Spectrum of Hawaiienol B (2; 600 MHz, Acetone-d 6 ) H-2,6 H-3,5,3,5 H-2,6 4-OCH 3,4 -OCH 3 3 -OCH 3 H-6 H-5 OH-1 or4 OH-1 or4 OH-5 3 -OCH 3 4-OCH 3,4 -OCH 3 OH-5 OH-1 or4 H-5 H-6 OH-1 or4 H-3,5,3,5 H-2,6 H-2,6 14
15 Figure S13. 1 H NMR Spectrum of Hawaiienol C (3; 600 MHz, Acetone-d 6 ) 15
16 Figure S C NMR Spectrum of Hawaiienol C (3; 150 MHz, Acetone-d 6 ) 16
17 Figure S15. HSQC Spectrum of Hawaiienol C (3; 600 MHz, Acetone-d 6 ) 4-OCH 3,4 -OCH 3 H-2,6,2,6 H-3,5,3,5 H-2,5 H-3,6 4-OCH 3,4 -OCH 3 C-2,5 C-3,6 C-3,5,3,5 C-2,6,2,6 17
18 Figure S16. 1 H 1 H COSY Spectrum of Hawaiienol C (3; 600 MHz, Acetone-d 6 ) 4-OCH 3,4 -OCH 3 H-2,6,2,6 H-3,5,3,5 H-2,5 OH-3,6 H-3,6 OH-2,5 4-OCH 3,4 -OCH 3 OH-2,5 H-3,6 H-2,5 OH-3,6 H-3,5,3,5 H-2,6,2,6 18
19 Figure S17. HMBC Spectrum of Hawaiienol C (3; 600 MHz, Acetone-d 6 ) 4-OCH 3,4 -OCH 3 H-2,6,2,6 H-3,5,3,5 H-2,5 OH-3,6 H-3,6 OH-2,5 4-OCH 3,4 -OCH 3 C-2,5 C-3,6 C-1,4 C-3,5,3,5 C-2,6,2,6 C-1,1 C-4,4 19
20 Figure S18. NOESY Spectrum of Hawaiienol C (3; 600 MHz, Acetone-d 6 ) 4-OCH 3,4 -OCH 3 H-2,6,2,6 H-3,5,3,5 H-2,5 OH-3,6 H-3,6 OH-2,5 OH-2,5 4-OCH 3,4 -OCH 3 H-3,6 H-2,5 OH-3,6 H-3,5,3,5 H-2,6,2,6 20
21 Figure S19. 1 H NMR Spectrum of Hawaiienol D (4; 600 MHz, Acetone-d 6 ) 21
22 Figure S C NMR Spectrum of Hawaiienol D (4; 150 MHz, Acetone-d 6 ) 22
23 Figure S21. HSQC Spectrum of Hawaiienol D (4; 600 MHz, Acetone-d 6 ) 4 -OCH 3,4-OCH 3 H-2,6,2,6 H-3,5,3,5 H-3 H-6 H-5 4 -OCH 3,4-OCH 3 C-3 C-5 C-6 C-3,5,3,5 C-2,6,2,6 23
24 Figure S22. 1 H 1 H COSY Spectrum of Hawaiienol D (4; 600 MHz, Acetone-d 6 ) 4 -OCH 3,4-OCH 3 H-2,6,2,6 H-3,5,3,5 OH-1 H-3 OH-5 OH-4 OH-6 OH-3 H-6 H-5 4 -OCH 3,4-OCH 3 H-6,OH-3 H-5 OH-6 OH-4 OH-5 H-3 OH-1 H-3,5,3,5 H-2,6,2,6 24
25 Figure S23. HMBC Spectrum of Hawaiienol D (4; 600 MHz, Acetone-d 6 ) 4 -OCH 3,4-OCH 3 H-2,6,2,6 H-3,5,3,5 OH-1 H-3 OH-5 OH-4 OH-6 OH-3 H-6 H-5 4 -OCH 3,4-OCH 3 C-5,3 C-1, 6 C-4 C-3,5,3,5 C-1,2,6,2,6 C-1 C-4,4 C-2 25
26 Figure S24. NOESY Spectrum of Hawaiienol D (4; 600 MHz, Acetone-d 6 ) 4 -OCH 3,4-OCH 3 H-2,6,2,6 H-3,5,3,5 OH-5 OH-3 OH-1 H-3 OH-4 OH-6 H-5 H-6 4 -OCH 3,4-OCH 3 OH-3 H-6 H-5 OH-6 OH-4 OH-5 H-3 OH-1 H-3,5,3,5 H-2,6,2,6 26
27 Figure S25. Experimental CD Spectrum of 1 in MeOH 27
28 Figure S26. Relative Configurations of 2 (the Enantiomers Were Not Shown) 28
29 Figure S27. Relative Configurations of 4 (the Enantiomers Were Not Shown) 29
30 Figure S28. The Optimized Conformers for 2 2a 2a 2b 2b 2c 2c 2d 2d 30
31 2e 2e 2f 2f 2g 2g 2h 2h 31
32 Figure S29. The Optimized Conformers for 3 3a 3b 32
33 Figure S30. The Optimized Conformers for 4 4a 4a 4b 4b 4c 4c 4d 4d 33
34 4e 4e 4f 4f 4g 4g 4h 4h 34
35 4i 4i 4j 4j 4k 4k 4l 4l 35
36 4m 4m 4n 4n 4o 4o 4p 4p 36
37 Figure S31. The Optimized Conformer for 3a 37
38 Figure S32. Experimental CD Spectrum of 2 in MeOH and the Calculated ECD Spectra of 2a 2h and 2a 2h 38
39 Figure S33. Experimental CD Spectrum of 4 in MeOH and the Calculated ECD Spectra of 4a 4p and 4a 4p 39
40 Figure S34. Linear Regression Fitted 13 C NMR Chemical Shifts of 4 with Four Sets of Experimental Values (4i, 4l, 4n, and 4o) 40
41 Table S1. The Experimental and Computed 13 C NMR Data of 3 Position Experimental Calculated 3a-1 3a-2 Scaled Fitted OCH OCH
42 Table S2. Statistics of Ordinary Least Squares (OLS) Linear Regression of the Experimental and Computed 13 C NMR Chemical Shifts of 3 Assignment CMAD a CLAD b R 2 R 2 adj RMSE F p value 3a < a < 0.01 a CMAD = corrected mean absolute deviation, computed as (1/ n) δ calc δ exp. b CLAD = corrected largest absolute deviation, computed as max( δcalc δexp ). n i 42
43 Table S3. The Experimental and Computed 13 C NMR Data of 4 Position Experimental Calculated 4i 4l 4n 4o OCH OCH
44 Table S4. Statistics of Ordinary Least Squares (OLS) Linear Regression of the Experimental and Computed 13 C NMR Chemical Shifts of 4 Configuration CMAD a CLAD b R 2 R 2 adj RMSE F p value 4i < l < n < o < 0.01 a CMAD = corrected mean absolute deviation, computed as (1/ n) δ calc δ exp. b CLAD = corrected largest absolute deviation, computed as max( δcalc δexp ). n i 44
45 Scheme S1. Plausible Biosynthetic Pathways for 1 4 Methylation 45
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