Depsidomycins B and C: New Cyclic Peptides from a Ginseng Farm Soil-derived Actinomycete.

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Supporting Information Depsidomycins B and C: ew Cyclic Peptides from a Ginseng Farm Soil-derived Actinomycete. Yun Kwon 1, Woong Sub Byun 1, Byung-Yong Kim 2, Myoung Chong Song 3, Munhyung Bae 1, Yeo Joon Yoon 3, Jongheon Shin 1, Sang Kook Lee 1 and Dong-Chan h 1, * 1 atural Product Research Institute, College of Pharmacy, Seoul ational University, Seoul 8826, Republic of Korea 2 ChunLab, Inc., JW TWER, Seocho-gu, Seoul 6725, Republic of Korea 3 Department of Chemistry and anoscience, Ewha Womans University, Seoul 376, Republic of Korea * Correspondence: dongchanoh@snu.ac.kr; Tel.: +82-288-24-91

Table of Contents Figure S1. 1 MR spectrum (85 Mz) of depsidomycin B (1) in pyridine d5. Figure S2. 13 C MR spectrum (212.5 Mz) of 1 in pyridine d5. Figure S3. CSY spectrum (85 Mz) of 1 in pyridine d5. Figure S4. SQC spectrum (85 Mz) of 1 in pyridine d5. Figure S5. MBC spectrum (85 Mz) of 1 in pyridine d5. Figure S6. RESY spectrum (85 Mz) of 1 in pyridine d5. Figure S7. TCSY spectrum (85 Mz) of 1 in pyridine d5 Figure S8. 1 MR spectrum (85 Mz) of 1 in acetone d6. Figure S9. 13 C MR spectrum (212.5 Mz) of 1 in acetone d6. Figure S1. CSY spectrum (85 Mz) of 1 in acetone d6. Figure S11. SQC spectrum (85 Mz) of 1 in acetone d6. Figure S12. MBC spectrum (85 Mz) of 1 in acetone d6. Figure S13. RESY spectrum (85 Mz) of 1 in acetone d6. Figure S14. TCSY spectrum (85 Mz) of 1 in acetone d6. Figure S15. 1 MR spectrum (85 Mz) of depsidomycin C (2) in acetone d6. Figure S16. 13 C MR spectrum (212.5 Mz) of 2 in acetone d6. Figure S17. CSY spectrum (85 Mz) of 2 in acetone d6. Figure S18. SQC spectrum (85 Mz) of 2 in acetone d6. Figure S19. MBC spectrum (85 Mz) of 2 in acetone d6. Figure S2. RESY spectrum (85 Mz) of 2 in acetone d6. Figure S21. TCSY spectrum (85 Mz) of 2 in acetone d6. Figure S22. 1 MR spectrum (6 Mz) of methanolysis product (3) of 1 in acetone d6. Figure S23. 13 C MR spectrum (15 Mz) of 3 in acetone d6. Figure S24. CSY spectrum (6 Mz) of 3 in acetone d6. Figure S25. SQC spectrum (6 Mz) of 3 in acetone d6. Figure S26. MBC spectrum (6 Mz) of 3 in acetone d6.

Figure S27. TCSY spectrum (6 Mz) of 3 in acetone d6. Figure S29. LC/MS chromatogram of (a) L- and (b) D-FDAA derivatives of 1. Figure S3. LC/MS chromatogram of (a) L- and (b) D-FDAA derivatives of 2. Figure S31. LC/MS chromatogram of GITC derivatives of (a) 1, (b) authentic D-Ile, (c) D-allo- Ile, (d) coinjection of GITC derivatives of 1 with authentic (d) D-Ile and (e) D-allo-Ile. Figure S32. LC/MS chromatogram of GITC derivatives of (a) 1, (b) authentic D-Thr, (c) L-Thr, (d) D-allo- and L-allo-Thr, and coinjection of GITC derivatives of authentic D-Thr with those of (e) 1 and (f) 2. Figure S33. Positive control data of wound healing assay using sunitinib. Figure S34. Time-course LC/MS analysis of the culture of the strain BYK1371. Depsidomycins B and C (1-2) were detected at 15.4 and 14.6, respectively. Figure S35. Phylogenetic relationships of single strain BYK 1371 and related Streptomyces taxa. Table S1. 1 and 13 C MR data for 1 in pyridine-d5. Table S2. 1 and 13 C MR data for 3 in acetone-d6. Table S3. 1 and 13 C MR data for depsidomycin and B (1) in acetone-d6. Table S4. LC/MS analysis of the FDAA derivatives of 1 and 2. References

Figure S1. 1 MR spectrum (85 Mz) of 1 in pyridine d5.

Figure S2. 13 C MR spectrum (212.5 Mz) of 1 in pyridine d5.

Figure S3. CSY spectrum (85 Mz) of 1 in pyridine d5.

Figure S4. SQC spectrum (85 Mz) of 1 in pyridine d5.

Figure S5. MBC spectrum (85 Mz) of 1 in pyridine d5.

Figure S6. RESY spectrum (85 Mz) of 1 in pyridine d5.

Figure S7. TCSY spectrum (85 Mz) of 1 in pyridine d5.

Figure S8. 1 MR spectrum (85 Mz) of 1 in acetone d6.

Figure S9. 13 C MR spectrum (212.5 Mz) of 1 in acetone d6.

Figure S1. CSY spectrum (85 Mz) of 1 in acetone d6.

Figure S11. SQC spectrum (85 Mz) of 1 in acetone d6.

Figure S12. MBC spectrum (85 Mz) of 1 in acetone d6.

Figure S13. RESY spectrum (85 Mz) of 1 in acetone d6.

Figure S14. TCSY spectrum (85 Mz) of 1 in acetone d6.

Figure S15. 1 MR spectrum (85 Mz) of 2 in acetone d6.

Figure S16. 13 C MR spectrum (212.5 Mz) of 2 in acetone d6.

Figure S17. CSY spectrum (85 Mz) of 2 in acetone d6.

Figure S18. SQC spectrum (85 Mz) of 2 in acetone d6.

Figure S19. MBC spectrum (85 Mz) of 2 in acetone d6.

Figure S2. RESY spectrum (85 Mz) of 2 in acetone d6.

Figure S21. TCSY spectrum (85 Mz) of 2 in acetone d6.

Figure S22. 1 MR spectrum (6 Mz) of 3 in acetone d6.

Figure S23. 13 C MR spectrum (15 Mz) of 3 in acetone d6.

Figure S24. CSY spectrum (6 Mz) of 3 in acetone d6.

Figure S25. SQC spectrum (6 Mz) of 3 in acetone d6.

Figure S26. MBC spectrum (6 Mz) of 3 in acetone d6.

Figure S27. TCSY spectrum (6 Mz) of 3 in acetone d6.

Figure S28. MS/MS data of 3.

Figure S29. LC/MS chromatogram of (a) L- and (b) D-FDAA derivatives of 1. (a) 6 MSD1 383, EIC=382.7:383.7 (:\LCMS\BYK1371\BYK1371_L_MARFEY_791.D) 13.558 13.622 ES-API, Pos, Scan, Frag: 135, "pos scan" Leucine, Isoleucine 4 2 4 3 15.231 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD1 371, EIC=37.7:371.7 (:\LCMS\BYK1371\BYK1371_L_MARFEY_791.D) ES-API, Pos, Scan, Frag: 135, "pos scan" 22.659 Threonine 2 1 15 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD2 481, EIC=48.7:481.7 (:\LCMS\BYK1371\BYK1371_L_MARFEY_791.D) ES-API, eg, Scan, Frag: 135, "neg scan" Piperazic acid 29.86 1 (b) 1.371 11.174 13.965 15.483 5 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD2 368, EIC=367.7:368.7 (:\LCMS\BYK1371\BYK1371_L_MARFEY_791.D) ES-API, eg, Scan, Frag: 135, "neg scan" 8 Valine 6 4 2 1 12.5 15 17.5 2 22.5 25 27.5 3 14.64 16.872 18.71 MSD1 383, EIC=382.7:383.7 (:\LCMS\BYK1371\BYK1371_D_MARFEY_791.D) ES-API, Pos, Scan, Frag: 135, "pos scan" 3 25 2 15 1 5 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD1 371, EIC=37.7:371.7 (:\LCMS\BYK1371\BYK1371_D_MARFEY_791.D) ES-API, Pos, Scan, Frag: 135, "pos scan" 15 125 Threonine 1 75 5 25 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD2 481, EIC=48.7:481.7 (:\LCMS\BYK1371\BYK1371_D_MARFEY_791.D) ES-API, eg, Scan, Frag: 135, "neg scan" 6 4 11.473 17.555 18.624 2.246 2.357 2.771 22.673 23.393 23.488 23.615 24.114 24.422 25.239 25.631 26.616 26.87 27.357 29.154 3.178 3.45 3.664 Leucine, Isoleucine Piperazic acid 31 3 11.378 16.56 18.72 2 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD2 368, EIC=367.7:368.7 (:\LCMS\BYK1371\BYK1371_D_MARFEY_791.D) ES-API, eg, Scan, Frag: 135, "neg scan" 4 3 2 1 1 12.5 15 17.5 2 22.5 25 27.5 3 13.511 18.62 21.484 22.659 22.868 22.654 26.637 27.116 27.251 Valine

Figure S3. LC/MS chromatogram of (a) L- and (b) D-FDAA derivatives of 2. (a) 6 MSD1 383, EIC=382.7:383.7 (:\LCMS\BYK1371\BYK1371_777_L_MARFEY.D) 13.389 ES-API, Pos, Scan, Frag: 135, "pos scan" Leucine, Isoleucine 4 15.197 15.564 15.689 17.61 17.266 2 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD1 371, EIC=37.7:371.7 (:\LCMS\BYK1371\BYK1371_777_L_MARFEY.D) ES-API, Pos, Scan, Frag: 135, "pos scan" 3 2 1 3 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD2 481, EIC=48.7:481.7 (:\LCMS\BYK1371\BYK1371_777_L_MARFEY.D) ES-API, eg, Scan, Frag: 135, "neg scan" 22.495 24.45 Threonine Piperazic acid 29.765 2 1 (b) 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD2 368, EIC=367.7:368.7 (:\LCMS\BYK1371\BYK1371_777_L_MARFEY.D) ES-API, eg, Scan, Frag: 135, "neg scan" 3 2 1 18.476 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD1 383, EIC=382.7:383.7 (:\LCMS\BYK1371\BYK1371_777_D_MARFEY.D) ES-API, Pos, Scan, Frag: 135, "pos scan" 11.41 22.477 25.47 Valine 4 3 2 1 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD1 371, EIC=37.7:371.7 (:\LCMS\BYK1371\BYK1371_777_D_MARFEY.D) ES-API, Pos, Scan, Frag: 135, "pos scan" 13.347 14.464 15.2 15.263 16.676 17.366 18.484 15 1 5 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD2 481, EIC=48.7:481.7 (:\LCMS\BYK1371\BYK1371_777_D_MARFEY.D) ES-API, eg, Scan, Frag: 135, "neg scan" 4 Piperazic acid 3 2 1 1 12.5 15 17.5 2 22.5 25 27.5 3 MSD2 368, EIC=367.7:368.7 (:\LCMS\BYK1371\BYK1371_777_D_MARFEY.D) ES-API, eg, Scan, Frag: 135, "neg scan" 25 2 15 1 5 11.195 18.443 18.518 19.336 1 12.5 15 17.5 2 22.5 25 27.5 3 2.373 2.728 21.296 22.446 22.523 23.3 24.49 26.51 28.626 Leucine, Isoleucine Threonine Valine

Figure S31. LC/MS chromatogram of GITC derivatives of (a) 1, (b) authentic D-Ile, (c) D-allo-Ile, (d) coinjection of GITC derivatives of 1 with authentic (d) D-Ile and (e) D-allo-Ile. MSD1 521, EIC=52.7:521.7 (:\LCMS\BYK1371\GITC\ISLEUCIE\BYK1371_791_GITC.D) ES-API, Pos, Scan, Frag: 135, "pos s 4 3 2 1 (a) Depsidomycin (1) 36.63 36.148 39.54 2 25 3 35 4 45 5 55 6 65 MSD2 MSD1 519 521, EIC=52.7:521.7 518 7 519 7 (:\LCMS\BYK1371\GITC\ISLEUCIE\D_ISLEUCIE_GITC_35T5.D) \LCMS\BYK1371\GITC\ISLEUCIE\BYK1371 791 D) ES API ES-API, S Pos, F Scan, 135 " Frag: 135 43.22 49.215 49.357 5.452 5.595 5.654 52.846 54.24 53.923 3 2 (b) D-Ile 52.987 53.199 53.39 53.442 53.557 36.19 1 2 25 3 35 4 45 5 55 6 65 MSD1 MSD2 521, 519 EIC=52.7:521.7 518 7 519 7 (:\LCMS\BYK1371\GITC\ISLEUCIE\D_ALL_ISLEUCIE_GITC_35T5.D) ISLEUCIE 35T5 D) ES API ES-API, S Pos, F Scan, 135 Frag 49.321 5.651 5.843 54.69 55.641 57.94 3 2 (c) D-allo-Ile 52.275 52.39 52.732 1 2 25 3 35 4 45 5 55 6 65 MSD2 MSD1 519 521, EIC=52.7:521.7 518 7 519 7 (:\LCMS\BYK1371\GITC\ISLEUCIE\GITC \LCMS\BYK1371\GITC\ISLEUCIE\D ALL WIT ISLEUCIE 791\791_WIT_D_ISLEUCIE_GITC_35T5_2.D) 35T5 D) ES API S F ES-A 49.91 54.337 54.536 54.723 54.917 55.98 55.293 55.841 56.86 57.2 58.311 2 15 (d) Coinjection of 1 with D-Ile 1 5 2 25 3 35 4 45 5 55 6 65 MSD2 519, EIC=518.7:519.7 (:\LCMS\BYK1371\GITC\ISLEUCIE\GITC WIT 791\791_WIT_D_ALL_ISLEUCIE_GITC_35T5.D) 36.548 36.755 39.541 39.418 49.48 49.328 49.395 5.528 5.792 5.665 53.255 53.417 53.477 53.586 53.81 55.325 56.264 65.9 66.72 68.813 69.26 4 3 2 1 2 25 3 35 4 45 5 55 6 65 2.24 (e) Coinjection of 1 with D-allo-Ile 33.53 36.113 36.44 36.325 36.557 36.753 39.331 39.417 39.57 39.698 49.578 49.763 51.113 5.995 52.84 52.945 53.54 53.162 53.328 53.489 53.57 53.666 53.787 54.262 54.25 54.449 56.232 56.137 57.85 6.145 66.41 69.361

Figure S32. LC/MS chromatogram of GITC derivatives of (a) 1, (b) authentic D-Thr, (c) L-Thr, (d) D-allo- and L-allo-Thr, and coinjection of GITC derivatives of authentic D-Thr with those of (e) 1 and (f) 2. 3 2 1 4 MSD1 59, EIC=58.7:59.7 (:\LCMS\BYK1371\BYK1371 ALL\BYK1371_791_GITC_REACTI_DC_DEFAULT.D) (a) Depsidomycin (1) 7.824 9.626 9.9 ES-API, Pos, Scan, 11.61 5 1 15 2 25 MSD2 MSD1 59, 57 EIC=58.7:59.7 56 7 57 7 (:\LCMS\BYK1371\GITC\TREIE\GITC_D_TREIE_1_T_1_R.D) \LCMS\BYK1371\BYK1371 ALL\BYK1371 791 REACTI DC DEFAULT ES-API, D) Pos, ES API Scan, Frag: S 1 (b) D-Thr 9.67 14.489 9.117 2 5 1 15 2 25 MSD2 MSD1 57 59, EIC=58.7:59.7 56 7 57 7 (:\LCMS\BYK1371\GITC\TREIE\GITC_L_TREIE.D) D TREIE 1ES-API, T 1 RPos, D) Scan, ES API Frag: 135, S "pos F sc 1 1 8 6 4 2 2 (c) L-Thr 8.847 9.328 1.8 1.635 1.961 11.39 11.732 12.48 15.168 5 1 15 2 25 MSD2 57, EIC=56.7:57.7 (:\LCMS\BYK1371\GITC\TREIE\GITC_DL_TREIE_8_T_1.D) ES-API, eg, Scan, Frag: 135, (d) D-allo- and L-allo-Thr 8.546 1.611 11.937 2 1 5 1 15 2 25 MSD1 59, EIC=58.7:59.7 (:\LCMS\BYK1371\GITC\TREIE\GITC WIT 791\GITC_D_TREIE_AD_791GITC_2.D) ES-API, P (e) D-Thr + depsidomycin B (1) 9.588 9.886 11.374 11.649 5 1 15 2 25 MSD2 57 EIC 56 7 57 7 ( \LCMS\BYK1371\GITC\TREIE\GITC WIT 791\GITC D TREIE AD 791GITC 2 D) ES API (f) D-Thr + depsidomycin C (2)

Figure S33. Positive control data of wound healing assay using sunitinib. Remaining cell free area (%)

Figure S34. Time-course LC/MS analysis of the culture of the strain BYK1371. Depsidomycins B and C (1-2) were detected at 15.4 and 14.6, respectively. 2 15 1 5 MSD1 TIC, MS File (:\LCMS\BYK1371\BYK1371 ALL\13MAY_D2_YEMEF_BYK1371.D).123.843 1.333 1.496 1.684 2.279 2.44 3.24 4.952 5.245 5.712 5.97 6.11 6.35 6.632 7.15 7.61 7.827 8.56 ES-API, Pos, Scan, Frag: 135, "pos scan" 8.378 8.78 8.97 9.276 9.488 9.913 1.58 1.865 11.178 11.762 12.374 12.89 13.276 13.764 2 1 14.277 14.61 15.52 15.397 15.739 5 1 15 2 25 16.345 17.7 17.417 17.711 18.262 18.931 19.86 2.489 21.59 21.352 21.569 22.59 22.786 Day-2 28.49 29.135 2 15 1 5 MSD1 TIC, MS File (:\LCMS\BYK1371\BYK1371 ALL\13MAY_D2_YEMEF_BYK1371.D).123.843 1.333 1.496 1.684 2.279 2.44 3.24 4.952 5.245 5.712 5.97 6.11 6.35 6.632 7.15 7.61 7.827 8.56 ES-API, Pos, Scan, Frag: 135, "pos scan" 8.378 8.78 8.97 9.276 9.488 9.913 1.58 1.865 11.178 11.762 12.374 5 1 15 2 25 MSD2 TIC MS Fil ( \LCMS\BYK1371\BYK1371 ALL\13MAY D2 YEMEF BYK1371 D) ES API S F 135 " " 12.89 13.276 13.764 14.277 14.61 15.52 15.397 15.739 16.345 17.7 17.417 17.711 18.262 18.931 19.86 2.489 21.59 21.352 21.569 22.59 22.786 Day-4 28.49 29.135 2 15 1 5 MSD1 TIC, MS File (:\LCMS\BYK1371\BYK1371 ALL\17_MAY_YEMEF_D6_BYK1371.D).125.364 1.5 1.195 1.331 1.673 1.828 2.429 2.87 3.192 3.556 3.879 4.25 4.411 4.91 5.276 5.752 6.6 6.289 6.626 6.992 7.69 7.779 8.76 8.386 ES-API, Pos, Scan, Frag: 135, "pos scan" 8.743 9.15 9.28 9.56 9.82 9.942 1.737 1.997 11.427 11.619 11.992 12.39 12.854 13.185 13.356 13.816 13.966 14.326 14.624 15.52 15.429 15.748 16.58 16.355 16.88 5 1 15 2 25 17.187 17.41 17.724 18.21 18.511 18.872 19.229 19.828 2.413 2.952 21.51 21.882 22.197 22.847 Day-5 28.56 29.34 29.158 29.41 29.694 MSD1 TIC, MS File (:\LCMS\BYK1371\BYK1371 ALL\16MAY_YEMEF_D5_BYK1371.D) ES-API, Pos, Scan, Frag: 135, "pos scan" 2 15 1 5 5 1 15 2 25.126 1.326 1.678 2.433 2.793 3.189 3.689 3.949 4.422 4.731 4.875 5.253 5.76 5.97 6.27 6.595 6.978 7.581 7.726 8.27 8.381 8.724 8.992 9.175 9.457 9.698 1.448 1.718 12.284 12.794 13.142 13.753 13.962 14.57 15.391 16.328 16.913 17.174 17.389 17.71 18.213 18.638 18.897 19.238 19.849 2.137 2.457 2.963 Day-6 28.487 28.88 29.257 29.176 29.743

Figure S35. Phylogenetic relationships of single strain BYK 1371 and related Streptomyces taxa. The evolutionary history was inferred using the eighbor-joining method [1]. The tree based on partial 16S rra gene sequences (about 1,4 nucleotides) showing the relationships between isolate BYK1371 and the closely related type strains of the genus Streptomyces. umbers at the nodes indicate levels of bootstrap support (%) above 5% based on a neighbour-joining analysis of 1, resampled datasets [2]. Genbank accession numbers are indicated in parentheses. The scale bar indicates the number of substitutions per nucleotide position. The evolutionary distances were computed using the Kimura 2-parameter method [3] and are in the units of the number of base substitutions per site. The analysis involved 33 nucleotide sequences. All positions containing gaps and missing data were eliated. Evolutionary analyses were conducted in MEGA X [4]. S 38

Table S1. 1 and 13 C MR data for 1 in pyridine-d5. positon Depsidomycin B (1) δc, type a δ, mult (J in z) a 1 169.5, C 2 51.5, C 5.43, br d (3.5) 3a 21.6, C2 1.3, m 3b 1.88, m 4a 21.3, C2 1.6, m 4b 2.11, m 5a 48.2, C2 2.66, m 5b 3.6, m 5-5.69, br d (12.) 6 175.5, C 7 49.9, C 6.2, dd (1.5, 1.) 7-8.39, br d (1.) 8a 41.7, C2 2.1, m 8b 2.54, br dd (1., 1.) 9 27., C 2.15, m 1 24.1, C3 1.12, d (6.5) 11 21.5, C3 1.24, d (6.5) 12 168.6, C 13 53.1, C 5.77, br d (5.) 14a 25.4, C2 1.65, m 14b 2.91, br d (11.) 15a 23.3, C2 1.48, d (9.) 15b 1.63, m 16a 48.1, C2 3.12, m 16b 2.78, m 16-4.44, br d (13.) 17 176.3, C 18 56.8, C 5.58, m 18-9.33, br d (5.) 19 29.2, C 2.33, m 2 2.2, C3 1.5, m 21 2.5, C3 1.7, m 22 175.3, C 23 51.5, C 5.38, m 23-7.61, br d (1.) 24a 41., C2 2.4, m 24b 2.61, m 25 26.1, C 1.89, m 26 24.3, C3.75, m 27 2.8, C3.79, m 28 168.2, C 29 56.2, C 5.33, m 29-9.19, d (8.) 3 72.3, C 5.21, br s 31 14.5, C3 1.34, d (6.) 32 172.1, C 33 56., C 5.35, m 33-9.44, br s 34 38.8, C 2.23, m 35 27.3, C2 1.24, d (6.5) 1.59, m 36 12.3, C3.77, m 37 15.4, C3 1., d (7.) 38 162.2, C 8.77, s a 1 and 13 C MR were recorded at 8 and 212.5 Mz, respectively. 4 38 3 35 5 36 2 34 1 32 33 8 6 3 37 29 9 7 31 28 12 13 14 17 18 23 24 22 15 19 25 16 S 39

Table S2. 1 and 13 C MR data for 3 in Acetone-d6. positon 3 δc, type a δ, mult (J in z) a 1 172.1, C 2 52., C 5.2, d (6.) 3a 26.1, C2 1.87, m 3b 2.21, m 4 21.3, C2 1.57, br s 5a 47.7, C2 3.6, m 5b 2.89, m 5-4.52, br d (12.5) 6 175.1, C 7 49.1, C 5.41, m 7-7.35, brd (8.) 8 41., C2 1.55, m 9 25.6, C 1.75, m 1 2., C3.86, m 11 23.8, C3.92, d (6.5) 12 171.1, C 13 51.5, C 5.11, br d (5.) 14a 26.6, C2 1.74, m 14b 2.33, br d (13.5) 15a 21.4, C2 1.55, m 15b 1.59, br 16a 48.4, C2 3.1, m 16b 2.71, m 16-4.72, br d (13.5) 17 175.2, C 18 52.2, C 5.27, m 18-7.4, br s 19 31.2, C 2.8, m 2 18.3, C3.87, d (6.5) 21 22., C3.92, d (6.5) 22 173.4, C 23 53.6, C 4.38, m 23-7.64, br s 24 41.2, C2 1.64, m 25 26.3, C 1.73, m 26 21.6, C3.85, m 27 2., C3.9, m 28 171.5, C 29 57.2, C 4.45, m 29-7.4, d (6.) 3 67.9, C 4.28, m 31 2.3, C3 1.14, d (6.5) 32 172.2, C 33 57.2, C 4.45, m 33-8.1, br s 34 37.3, C 2.5, m 35 27.3, C2 1.28, d (6.5) 1.49, d (6.5) 36 12.1, C3.93, m 37 15., C3.95, d (7.) 38 163.3, C 8.29, s 39 52.7, -C3 3.74, s a 1 and 13 C MR were recorded at 6 and 15 Mz, respectively. 26 1 2 3 12 27 38 7 24 6 25 4 8 14 13 22 35 18 29 32 34 5 9 17 23 28 33 19 3 11 15 37 16 2 21 31 36 S 4

Table S3. 1 and 13 C MR data for depsidomycin and B (1) in Acetone-d6. Positon Depsidomycin Depsidomycin B (1) δc, type δ, mult (J in z) a δc, type δ, mult (J in z) b 1 169.3, C 169.3, C 2 51.6, C 5.16, dd (5., 2.) 51.4, C 5.18, br s 3a 23.4, C2 1.86, m 23.4, C2 1.85, m 3b 2.19, m 2.19, m 4a 21.4, C2 1.55, m 21.3, C2 1.55, m 4b 1.86, m 1.86, m 5a 47.8, C2 3.14, m 47.9, C2 3.12, m 5b 2.85, m 2.85, m 5-4.88, dd (12., 2.5) 4.88, m 6 175.4, C 175.4, C 7 49.6, C 5.4, m 49.7, C 5.4, dd (1.5, 1.5) 7-7.65, d (1.) 7.62, d (1.5) 8a 41.4, C2 1.69, m 41.4, C2 1.68, m 8b 1.95, m 1.95, m 9 26.8, C 1.78, m 26.6, C 1.78, m 1 21.3, C3 1.2, d (6.5) 21., C3 1.2, d (6.5) 11 23.8, C3.93, d (6.5) 23.7, C3.93, d (6.5) 12 167.9, C 167.7, C 13 53.1, C 5.11, dd (5.5, 1.5) 52.8, C 5.12, d (4.5) 14a 25.1, C2 1.55, m 24.9, C2 1.58, m 14b 2.57, m 2.57, br d (13.5) 15a 23., C2 1.4, m 23., C2 1.39, m 15b 1.55, m 1.55, br d (1.5) 16a 48., C2 2.77, m 47.8, C2 2.75, m 16b 3.12, m 3.12, m 16-3.94, dd (13., 2.) 3.95, br d (12.5) 17 175.3, C 175.9, C 18 56.3, C 5.2, dd (1.5, 6.) 56.2, C 5.2, dd (1., 6.) 18-7.56, d (6.) 7.59, d (6.) 19 29.4, C 1.98, m 29,5, C 1.99, m 2 2.1, C3 1.5, d (6.5) 21., C3 1.2, d (6.5) 21 19.9, C3.97, d (6.5) 19.7, C3.97, d (6.5) 22 174.8, C 174.7, C 23 51.2, C 4.97, m 51., C 4.88, m 23-7.1, d (1.) 7.7, br s 24a 24b 41.1, C2 1.68, m 2.17, m 4.8, C 1,68, m 2.17, m 25 25.9, C 1.7, m 25.8, C 1.71, m 26 2.8, C3.89, d (7.) 2.6, C3.89, m 27 24.1, C3.91, d (7.) 24., C3.91, m 28 167.4, C 167.4, C 29 55.9, C 4.5, dd (6.5, 3.5) 55.8, C 4.48, br s 29-7.69, d (6.5) 7.52, br s 3 71.4, C 4.9, dq (6.5, 3.5) 71.4, C 4.91, m 31 13.9, C 1.17, d (6.5) 13.6, C3 1.17, d (6.5) 32 171.1, C 171.7, C 33 55.5, C 4.76, dd (9.5, 4.5) 55.4, C 4.66, m 33-7.52, d (9.5) 7.49, br s 34 38.5, C 1.92, m 38.1, C 1.98, m 35a 27., C2 1.19, m 26.9, C2 1.21, m 35b 1.42, m 1.43, m 36 12.1, C3.89, t (7.5) 11.8, C3.9, m 37 14.7, C3.87, d (7.) 14.6, C3.87, d (7.) 38 161.8, C 8.27, br s 161.8, C 8.27, s a 1 and 13 C MR were cited from the origin paper. b 1 and 13 C MR were recorded at 85 and 212.5 Mz, respectively S 41

Table S4. LC/MS analysis of the FDAA derivatives of 1 and 2. Depsidomycin B (1) Depsidomycin C (2) Ao acid Elution trl () trd () Ao acid Elution trl () trd () order order Val (D) D L 22.6 18.6 Val (D) D L 22.4 18.4 Leu (D) D L 13.6 11.4 Leu (D) D L 13.3 11.4 Ile (D) D L 13.6 11.4 Ile (D) D L 13.3 11.4 Thr (D) D L 22.6 18.6 Thr (D) D L 22.4 18.4 Pip (S) D L 29.8 26.6 Pip (S) D L 29.7 26.5 S 42

References. 1. Saitou.; ei M. The neighbor-joining method: A new method for reconstructing phylogenetic trees. Mol. Biol. Evol. 1987, 4, 46-425. 2. Felsenstein J. Confidence limits on phylogenies: An approach using the bootstrap. Evolution 1985, 39, 783-791. 3. Kimura M. A simple method for estimating evolutionary rate of base substitutions through comparative studies of nucleotide sequences. J. Mol. Evol. 198, 16, 111-12. 4. Kumar S.; Stecher G.; Li M., Knyaz C.; Tamura K. MEGA X: Molecular evolutionary genetics analysis across computing platforms. Mol. Biol. Evol. 218 (https://doi.org/1.193/molbev/msy96). S 43

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