Two new sesquiterpenes from a kind of TCM Pieces, Curcumae Radix
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1 Supporting Information Rec. Nat. Prod. 8:4 (2014) Two new sesquiterpenes from a kind of TCM Pieces, Curcumae Radix onghua Wu *1,2, onghong Zheng 1,2, Yantong Xu 1,2, Peng Zhang 1,2, Gang Chen 3 and Yan Zhu 1,2 1 Tianjin State Key Laboratory of Modern Chinese Medicine; Tianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin University of Traditional Chinese Medicine, Tianjin , P.R.China 2 Research and Development Center of TCM, Tianjin International Joint Academy of Biotechnology & Medicine, 220 Dongting Road, TEDA, Tjianjin , P.R.China 3 School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang , P.R.China Table of Contents Page S1: RESI-MS Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 4 S2: 1 -NMR (600Mz, DMS-d 6 ) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 5 S3: Expansion of the 1 -NMR Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 6 S4: Expansion of the 1 -NMR Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 7 S5: 13 C-NMR (150Mz, DMS-d 6 ) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 8 * Corresponding author: wuhonghua2003@163.com; The author contributed equally 1
2 S6: Expansion of the 13 C-NMR Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 9 S7: SQC (600 Mz) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 10 S8: Expansion of the SQC Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 11 S9: MBC (600Mz) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 12 S10: Expansion of the MBC Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 13 S11: NESY (600Mz) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 14 S12: Expansion of the NESY Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 15 S13: RESI-MS Spectrum of Compound 2 Zedoalactone 16 S14: 1 -NMR (600Mz, DMS-d 6 ) Spectrum of Compound 2 Zedoalactone 17 S15: 1 -NMR Spectrum of Compound 2 Zedoalactone 18 S16: Expansion of the 1 -NMR Spectrum of Compound 2 Zedoalactone 19 S17: 13 C-NMR (150Mz, DMS-d 6 ) Spectrum of Compound 2 Zedoalactone 20 S18: Expansion of the 13 C-NMR Spectrum of Compound 2 Zedoalactone 21 S19: Expansion of the 13 C-NMR Spectrum of Compound 2 Zedoalactone 22 S20: SQC (600 Mz) Spectrum of Compound 2 Zedoalactone 23 S21: MBC (600 Mz) Spectrum of Compound 2 Zedoalactone 24 S22: Expansion of the MBC Spectrum of Compound 2 Zedoalactone 25 S23: NESY (600Mz) Spectrum of Compound 2 Zedoalactone 26 S24: 1 -NMR (600Mz, DMS-d 6 ) Spectrum of Compound 3 Zedoalactone E 27 S25: 13 C-NMR (150Mz, DMS-d 6 ) Spectrum of Compound 3 Zedoalactone E 28 S26: SQC (600 Mz) Spectrum of Compound 3 Zedoalactone E 29 S27: MBC (600 Mz) Spectrum of Compound 3 Zedoalactone E 30 2
3 S28: NESY (600Mz) Spectrum of Compound 3 Zedoalactone E 31 S29: 1 -NMR (600Mz, DMS-d 6 ) Spectrum of Compound 4 Zedoarolide B 32 S30: 13 C-NMR (150Mz, DMS-d 6 ) Spectrum of Compound 4 Zedoarolide B 33 S31: SQC (600 Mz) Spectrum of Compound 4 Zedoarolide B 34 S32: MBC (600 Mz) Spectrum of Compound 4 Zedoarolide B 35 S33: 1 -NMR (400Mz, DMS-d 6 ) Spectrum of Compound 5 Gweicurculactone 36 S34: 13 C-NMR (100Mz, DMS-d 6 ) Spectrum of Compound 5 Gweicurculactone 37 S35: 1 -NMR (400Mz, DMS-d 6 ) Spectrum of Compound 6 Curdionolide A 38 S36: 13 C-NMR (100Mz, DMS-d 6 ) Spectrum of Compound 6 Curdionolide A 39 S37: 1 -NMR (400Mz, DMS-d 6 ) Spectrum of Compound 7 Curcumenone 40 S38: 13 C-NMR (100Mz, DMS-d 6 ) Spectrum of Compound 7 Curcumenone 41 S39: 1 -NMR (400Mz, CDCl 3 ) Spectrum of Compound 8 Curcuminol D 42 S40: 13 C-NMR (100Mz, CDCl 3 ) Spectrum of Compound 8 Curcuminol D 43 3
4 [M+Na] + S1: RESI-MS Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 4
5 S2: 1 -NMR(600Mz,DMS-d 6 ) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) (1R,4R,5S,7S)-curwenyujinone (1): colorless oil. 1 NMR (DMS-d 6,600 Mz), δ: 0.97 (3, d, 6.6, -14), 1.19 (3, s, -13), 1.31 (3, s, -12), 1.35 (1, m, -3b), 1.38 (1, m, -2b), 1.68 (3, br s, -15), 1.79 (1, d, 10.8, -6a), 1.86 (1, m, -2a), 2.05 (1, m, -3a), 2.11 (1, m, -4), 2.47 (1, dd, 10.8, 1.2, -6b), 2.52 (1, dd, 8.4, 9.6, -1), 4.45 (1, s, ), 5.70 (1, br s, -8). 13 C NMR (DMS-d 6, 150 Mz ): 50.7 (C-1), 23.5 (C-2), 30.1 (C-3), 37.8 (C-4), 90.5 (C-5), 35.9 (C-6), 57.0(C- 7), (C-8), (C-9), 176.3(C-10), 69.7(C-11), 25.4(C-12), 27.0 (C-13), 12.9(C-14), 20.7 (C- 15). 5
6 C a -1-6b -4/3a -2a S3: 1 -NMR Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) (From 1.65 to 2.60 ppm) 6
7 C 3-13 C C b/-3b S4: 1 -NMR Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) (From 0.95 to 1.42 ppm) 7
8 C8 C5 C10 C9 S5: 13 C-NMR (150Mz, DMS-d 6 ) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 8
9 C11 C7 C1 C4 C6 C3 C13 C12 C2 C15 C14 S6: 13 C-NMR Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) (From 10 to 70 ppm) 9
10 S7: SQC (600 Mz) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 10
11 14 /C14 15 /C15 12 /C12 2'-2''/C2 3'-3''/C3 13 /C13 6'-6''/C6 4 /C4 1 /C1 S8: SQC (600 Mz) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) (From 0.8 to 3.2 ppm) 11
12 S9: MBC (600Mz) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 12
13 S10: MBC Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) (From 10 to 75 ppm) 13
14 S11: NESY (600Mz) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) 14
15 S12: NESY (600Mz) Spectrum of Compound 1 ((1R,4R,5S,7S)-curwenyujinone) (From 0.9 to 2.8 ppm) 15
16 [M+] + [M+Na] + S13: RESI-MS Spectrum of Compound 2 Zedoalactone 16
17 S14: 1 -NMR (600Mz, DMS-d 6 ) Spectrum of Compound 2 Zedoalactone Zedoalactone (2): colourless oil, 1 -NMR (600 Mz, DMS-d 6 ), δ: 4.97 (1, m, -8), 4.40 (1, br s, ), 4.13 (1, br s, ), 2.60 (1, dd, 3.6, 12.0, -6), 2.50 (1, dd, 7.8, 10.4, -1), 2.28 (1, dd, 7.2, 15.0, -9), 1.95 (1, t, 12.6, -6), 1.86 (1, ddd, 3.6, 7.8, 13.8, -5), 1.73 (1, dd, 3.6, 15.6, -9), 1.69 (3, d, 1.8, -13), 1.65 (1, m, -2), 1.65 (1, m, -3), 1.58 (1, m, -3), 1.47 (1, m, -2), 1.20 (3, s, -14), 1.10 (3, s, -15). 13 C NMR (DMS-d 6, 150 Mz ): 52.0 (C-1), 24.9 (C-2), 38.1 (C-3), 80.3(C-4), 50.3 (C-5), 24.6 (C-6), 163.4(C-7), 80.8 (C-8), 38.8 (C-9), 72.0(C-10), 120.8(C- 11), 175.0(C-12), 8.2 (C-13), 25.2(C-14), 30.5 (C-15). 17
18 S15: 1 -NMR Spectrum of Compound 2 Zedoalactone (From 2.20 to 5.00 ppm) 18
19 C 3-14 C C '&-3'/3'' -1-6' -9' -6'' -5-9'' -2'' S16: 1 -NMR Spectrum of Compound 2 Zedoalactone (From 1.10 to 2.60 ppm) 19
20 C C12 C11 S17: 13 C-NMR (150Mz, DMS-d 6 ) Spectrum of Compound 2 Zedoalactone 20
21 C-8 C-4 C C-1 C-5 S18: 13 C-NMR (150Mz, DMS-d 6 ) Spectrum of Compound 2 Zedoalactone (From 47 to 82 ppm) 21
22 C-9 C-3 C-15 C-14 C-2 C C-13 S19: 13 C-NMR (150Mz, DMS-d 6 ) Spectrum of Compound 2 Zedoalactone (From 8 to 43 ppm) 22
23 S20: SQC (600 Mz) Spectrum of Compound 2 Zedoalactone 23
24 S21: MBC (600 Mz) Spectrum of Compound 2 Zedoalactone 24
25 S22: MBC (600 Mz) Spectrum of Compound 2 Zedoalactone (From 5 to 60 ppm) 25
26 S23: NESY (600Mz) Spectrum of Compound 2 Zedoalactone 26
27 S24: 1 -NMR (600Mz, DMS-d 6 ) Spectrum of Compound 3 Zedoalactone E Zedoalactone E (3): colourless oil, 1 -NMR (600 Mz, DMS-d 6 ), δ: 5.19 (1, d, 10.8, -8), 4.73 (1, br s, ), 4.37 (1, br s, ), 2.77 (1, m, -1), 2.63 (1, dd, 18.0, 4.8, -6), 2.30 (1, dd, 10.2, 18.0, -6), 2.07 (1, dd, 4.8, 10.2, -5), 2.04 (1, ddd, 1.8, 3.6, 10.2, -9), 1.70 (3, s, -13), 1.62 (1, dd, 11.4, 13.2, -9), 1.59 (1, m, -2), 1.54 (2, t, 7.8, 6.7, -3), 1.27 (1, m, -2), 1.23 (3, s, -14), 1.16 (3, s, -15). 13 C NMR (DMS-d 6, 150 Mz ): 52.0 (C-1), 24.5 (C-2), 37.3(C-3), 80.4 (C-4), 47.4 (C-5), 24.5 (C-6), 166.0(C-7), 79.5 (C-8), 40.7 (C-9), 71.0(C-10), 120.4(C-11), 174.5(C-12), 8.8(C-13), 25.7(C-14), 32.2(C-15). [15] 27
28 S25: 13 C-NMR (150Mz, DMS-d 6 ) Spectrum of Compound 3 Zedoalactone E 28
29 S26: SQC (600 Mz) Spectrum of Compound 3 Zedoalactone E 29
30 S27: MBC (600 Mz) Spectrum of Compound 3 Zedoalactone E 30
31 S28: NESY (600 Mz) Spectrum of Compound 3 Zedoalactone E 31
32 S29: 1 -NMR (600Mz, DMS-d 6 ) Spectrum of Compound 4 Zedoarolide B Zedoarolide B (4): colourless oil. 1 -NMR (DMS-d 6, 600 Mz): 4.34 (1, s, -4); 2.52 (1, m, -1); 2.42 (1, dd, 3.0, 12.0, -6a); 1.75 (1, m, -6b); 1.88 (1, m, -5); 1.68 (3, s, Me-13); 1.56~1.65 (2, m, -3); 1.40 (1, m, -2); 1.21 (3, s, Me-14); 1.07 (3, s, Me-15). 13 C-NMR (DMS-d 6, 150Mz): 52.2 (C-1), 24.9 (C-2), 37.7 (C-3), 80.4 (C-4), 51.3 (C-5), 24.2 (C-6), 71.6 (C- 10), (C-12), 8.8 (C-13), 25.3 (C-14), 31.8 (C-15). [16] 32
33 S30: 13 C-NMR (150Mz, DMS-d 6 ) Spectrum of Compound 4 Zedoarolide B 33
34 S31: SQC (600 Mz) Spectrum of Compound 4 Zedoarolide B 34
35 S32: MBC (600 Mz) Spectrum of Compound 4 Zedoarolide B 35
36 S33: 1 -NMR (400Mz, DMS-d 6 ) Spectrum of Compound 5 Gweicurculactone Gweicurculactone (5): range red needle crystal. 1 -NMR (DMS-d 6, 400Mz): 7.09 (1, s, -6); 6.95 (1, s, -9); 3.14 (1, m, -4); 2.77 (2, m, -2); 2.08 (1, m, -3a); 2.25 (3, s, Me-14); 1.92 (3, s, Me-13); 1.49 (1, m, -3b); 1.27 (3, d, 6.9, Me-15). 13 C-NMR (DMS-d 6, 100 Mz): (C-1), 33.6 (C-2), 31.8 (C-3), 43.8 (C-4), (C-5), (C-6), (C-7), (C-8), (C-9), (C-10),102.5 (C-11), (C-12), 7.8 (C-13), 24.6 (C-14), 20.5 (C-15). [17] 36
37
38 S35: 1 -NMR (400 Mz, DMS-d 6 ) Spectrum of Compound 6 Curdionolide A Curdionolide A (6): colorless oil. 1 -NMR(DMS-d 6, 400 Mz): 7.49 (1, br s, -8); 4.74 (1, d, 10.8, -1); 3.57 (1, d, 15.6, -6b); 3.44 (1, d, 15.6, -6a); 2.78 (1, d, 13.2, -9b); 2.49 (1, m, -4); 2.22 (1, m, -2b); 2.12 (1, d, 13.2, -9a); 1.90 (1, m, -2a); 1.87 (1, m, -3b); 1.86 (3, s, Me-15); 1.77 (3, s,me-13); 1.64 (1, m, -3a); 0.98 (3, d, J=6.6, Me-14). 13 C-NMR (DMS-d 6, 100 Mz): (C-1), 27.1 (C-2), 36.1 (C-3), 47.1 (C-4), (C-5), 40.6 (C-6), (C-7), (C-8), 50.1 (C-9), (C-10), (C-11), (C-12), 9.6 (C-13), 18.6 (C-14), 16.9 (C-15). [18] 38
39 S36: 13 C-NMR (100Mz, DMS-d 6 ) Spectrum of Compound 6 Curdionolide A 39
40 S37: 1 -NMR (400 Mz, DMS-d 6 ) Spectrum of Compound 7 Curcumenone Curcumenone (7). colourless oil. 1 -NMR (DMS-d 6, 400 Mz): 0.34 (1, m, -1); 0.67 (1, m, - 5); 1.07 (3, s, Me-15); 1.48 (2, m, -2); 1.76 (3, s, Me-13); 2.00 (3, s, Me-12); 2.06 (3, s, Me- 14); 2.35 (1, d, 15.4, -9a); 2.48 (2, t, 7.4, -3); 2.54(1, d, 15.4, -9b); 2.74(2, m, -6). 13 C- NMR (DMS-d 6, 100 Mz): 24.4 (C-1), 23.3 (C-2), 43.5 (C-3), (C-4), 23.8 (C-5), 28.0 (C-6), (C-7), (C-8), 49.0 (C-9), 20.0 (C-10), (C-11), 23.5 (C-12), 23.5 (C-13), 30.2 (C-14), 19.2 (C-15). [19] 40
41 S38: 13 C-NMR (100 Mz, DMS-d 6 ) Spectrum of Compound 7 Curcumenone 41
42 C S39: 1 -NMR (400 Mz, CDCl 3 ) Spectrum of Compound 8 Curcuminol D Curcuminol D (8): 1 -NMR (CDCl 3, 400 Mz): 0.79 (3, s, -20); 0.89 (3, s, Me-19); 0.91 (3, s, Me-18); 0.99 (1, td, 3.9, 12.8, -1a); 1.18 (1, td, 3.3, 12.8, -3a); 1.33 (1, dd, 5.0, 12.3, -5); 1.47 (1, m, -3b); 1.51 (1, m, -2a); 1.57 (1, dt, -2b); 1.87 (1, m, -1b); 1.96 (1, m, -6a); 2.12 (1, dd, 3.4, 14.3, -16a); 2.16 (1, m, -6b); 2.25 (1, t, 12.3, -14a); 2.32 (1, m, -11a); 2.40 (1, d, 14.2, -16b); 2.55 (1, d, 11.7, -9); 2.80 (1, dd, 5.8, 20.0, -11b); 3.11 (1, dd, 5.5, 13.2, -14b); 3.72 (1, m, -15); 5.66 (1, s, Me-7); 6.80 (1, s, -12); 9.34 (1, s, -17). 13 C- NMR (CDCl 3, 400 Mz): 39.6 (C-1), 19.0 (C-2), 42.0 (C-3), 33.0 (C-4), 50.1 (C-5), 24.3 (C-6), (C-7), (C-8), 51.4 (C-9), 36.5 (C-10), 30.8 (C-11), (C-12), (C-13), 29.8 (C-14), 69.7 (C-15), 41.2 (C-16), (C-17). [20] 42
43 C S40: 13 C-NMR (100 Mz, CDCl 3 ) Spectrum of Compound 8 Curcuminol D 43
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