Anticancer efficiency of cycloartane triterpenoid derivatives isolated from Cimicifuga yunnanensis Hsiao on triple-negative breast cancer cells

Figures & data

Figure 1 Structures of compounds 1–16.

Note: The structure of all compounds was tested using NMR spectral data analysis. Abbreviation: NMR, nuclear magnetic resonance.

Table 1 IC₅₀ values of compounds 1–16 on breast cancer cells, MCF-7, MDA-MB-231, or Sk-Br3

Compounds	IC50 (μg/mL)
	MCF-7	MDA-MB-231	SK-BR3
1. Actein	–	5.4	–
2. Cimigenol-3-O-β-d-xylopyranoside (23R,24S)	–	4.1	7.42
3. 26-Deoxyacetylacteol-3-O-α-l-arabinopyranoside	8.57	–	–
4. 23-Epi-26-deoxyactein	3.1	2.5	5.5
5. Cimifugin	–	–	–
6. Cimifugin glucoside	4.78	8.46	–
7. Norcimifugin glucoside	–	–	–
8. Norkhellol	–	–	–
9. 25-O-acetyl-cimigenol	–	–	–
10. 26-Deoxyacetylacteol	1.32	3.52	4.33
11. Acetylacteol	–	–	–
12. 25-O-Methyl-cimigenol	1.56	3.79	6.75
13. Cimigenol	0.1	0.32	0.21
14. 25-O-Acetylcimigenol-3-O-β-d-xylopyranoside	–	–	–
15. 24-O-Acetylhydroshengmanol-3-O-β-d-xylopyranoside	–	–	–
16. 26-Deoxyactein	2.77	5.46	–
Adriamycin	1.7	2.4	1.90

Figure 2 Compound 4 or 13 inhibited the subcutaneous growth of MDA-MB-231 cells.

Notes: MDA-MB-231-H cells were injected into nude mice to form subcutaneous tumors. Next, mice were divided into four groups: 1) solvent control group; 2) compound 4 group; 3) compound 13 group; (4) adriamycin group. Results are shown as follows: (A) photographs, (B) tumor volumes, and (C) tumor weights. *P<0.05.

Figure 3 Compound 4 or 13 inhibited the in vitro invasion of MDA-MB-231 cells.

Notes: MDA-MB-231 cells were treated with IC₅₀ of compound 4, compound 13, or adriamycin for 24 hours. Then, the cells were harvested for transwell experiments to reveal the in vitro invasion of MDA-MB-231 cells. Results are shown as follows: (A) photographs, (B) relative invasion number, or (C) inhibition rate of compound 4, compound 13, or adriamycin on MDA-MB-231’s in vitro invasion. *P<0.05.

Figure 4 Compound 4 or 13 inhibited the in vitro migration growth of MDA-MB-231 cells.

Notes: MDA-MB-231 cells were treated with IC₅₀ of compound 4, compound 13, or adriamycin for 24 hours. Then, the cells were harvested for transwell experiments to reveal the in vitro migration of MDA-MB-231 cells. Results are shown as follows: (A) photographs, (B) relative migration number, or (C) inhibition rate of compound 4, compound 13, or adriamycin on MDA-MB-231’s in vitro migration. *P<0.05.

Figure 5 Compound 4 or 13 inhibited the ^MicroPET signaling mice with the intrahepatic growth of MDA-MB-231 cells in the liver region.

Notes: MDA-MD-231 cells were injected into nude mice’s liver via hepatic portal vein. Next, the mice were divided into four groups: 1) solvent control group; 2) compound 4 treatment group; 3) compound 13 treatment group; 4) adriamycin treatment group. The tumor nodules formed by MHCC97-H cells in mice’s liver were examined by ^MicroPET scanning. Results are shown as follows: (A) ^MicroPET results from animals, (B) pixel ratio of tumor to body, or (C) intensity of tumor to body. Arrow indicates the tumor tissues in the liver. *P<0.05.

Abbreviation: PET, positron emission tomography.

Figure 6 Compound 4 or 13 inhibited the intrahepatic growth of MDA-MB-231 cells.

Notes: MDA-MD-231 cells were injected into nude mice’s liver via hepatic portal vein. Next, mice were divided into four groups: 1) solvent control group; 2) compound 4 treatment group; 3) compound 13 treatment group; 4) adriamycin treatment group. The tumor nodules formed by MHCC97-H cells in the mice’s liver were examined by ^MicroPET scanning. After ^MicroPET scanning, the liver organs in mice were harvested. Results are shown as follows: (A) tumor organs or (B) radioactivation of tumor tissue to blood or (C) relative nodule formed by MDA-MB-231 cells in the liver organ. White arrow in Figure 6 indicated the nodules formed by MDA-MB-231 cells in nude mice’s liver organ.*P<0.05.

Abbreviation: PET, positron emission tomography.

Figure S1 HPLC results of compounds 1–16.

Note: All compounds were examined by HPLC to achieve quality control of the chemicals.

Table S1 Chemical structure of compounds 1–16

Compound 1 (actein): white powder, C37H56O11, FAB-MS m/z: 676 [M]^+; ^13C-NMR (100 MHz, C5D5N) δc: 32.0 (t, C-1), 29.9 (t, C-2), 88.2 (d, C-3), 41.3 (s, C-4), 47.1 (d, C-5), 20.5 (t, C-6), 25.8 (t, C-7), 45.8 (d, C-8), 20.2 (s, C-9), 26.8 (s, C-10), 36.8 (t, C-11), 77.2 (t, C-12), 47.9(s, C-13), 48.8 (s, C-14), 43.7 (t, C-15), 73.1 (d, C-16), 56.5 (d, C-17), 13.7 (q, C-18), 29.5 (t, C-19), 26.1 (d, C-20), 21.1 (q, C-21), 37.6 (t, C-22), 105.9 (s, C-23), 63.5 (d, C-24), 65.7 (s, C-25), 98.2 (d, C-26), 13.2 (q, C-27), 19.7 (q, C-28), 26.8 (q, C-29), 15.4 (q, C-30), 170.7 (s, COCH3), 21.8 (q, COCH3), 107.6 (d, C-1’), 75.6 (d, C-2’), 78.6 (d, C-3’), 71.3 (d, C-4’), 67.1 (t, C-5’); 1H-NMR (400 MHz, C5D5N) δH: 0.23 (1H, d, J=4.0 Hz, H-19α), 0.56 (1H, d, J=4.0 Hz, H-19β), 0.78 (3H, s, H-28), 0.84 (3H, s, H-30), 0.97 (3H, d, J=9.3 Hz, H-21), 1.28 (3H, s, H-29), 1.34 (3H, s, H-18), 1.61 (1H, s, H-27), 1.76 (1H, s, H-26), 2.14 (3H, s, COCH3), 3.70 (1H, dd, J=4.2, 8.9 Hz, H-3), 3.90 (1H, s, H-24), 4.11 (1H, t, J=6.7 Hz, H-2’), 4.33 (1H, dd, J=2.7, 7.6 Hz, H-3’), 4.78 (1H, d, J=7.1 Hz, H-1’)

Compound 2 (cimigenol-3-O-β-d-xylopyranoside(23R,24S)): white powder, C35H56O9, FAB-MS m/z: 620 [M]^+, ^13C-NMR (100 MHz, C5D5N) δc: 32.6 (t, C-1), 30.3 (t, C-2), 88.7 (d, C-3), 41.5 (s, C-4), 47.7 (d, C-5), 21.2 (t, C-6), 26.5 (t, C-7), 48.8 (d, C-8), 20.2 (s, C-9), 26.8 (s, C-10), 26.6 (t, C-11), 34.2 (t, C-12), 42.0 (s, C-13), 47.4 (s, C-14), 80.4 (d, C-15), 112.1 (s, C-16), 59.7 (d, C-17), 19.7 (q, C-18), 31.0 (t, C-19), 24.2 (d, C-20), 19.7 (q, C-21), 38.3 (t, C-22), 72.0 (s, C-23), 90.3 (d, C-24), 71.4 (s, C-25), 25.5 (q, C-26), 25.9 (q, C-27), 12.0 (q, C-28), 27.3 (q, C-29), 15.6 (q, C-30), 107.8 (d, C-1’), 75.7 (d, C-2’), 78.8 (d, C-3’), 71.1 (d, C-4’), 67.3 (t, C-5’); 1H-NMR (400 MHz, C5D5N) δH: 0.30 (1H, d, J=3.3 Hz, H-19α), 0.54 (1H, d, J=3.3 Hz, H-19β), 0.87 (3H, d, J=6.3 Hz, H-21), 1.08 (3H, s, H-30), 1.31 (3H, s, H-29), 1.46 (3H, s, H-27), 1.48 (3H, s, H-28), 1.49 (3H, s, H-26), 1.49 (3H, s, H-18), 3.76 (1H, dd, J=4.0, 12.0 Hz, H-3), 4.07 (1H, t, J=7.8 Hz, H-2’), 4.19 (1H, t, J=8.6 Hz, H-3’), 4.37 (1H, dd, J=5.0, 11.2 Hz, H-4’), 4.74 (1H, d, J=9.0 Hz, H-23), 4.89 (1H, d, J=7.4 Hz, H-1’)

Compound 3 (26-deoxyacetylacteol-3-O-α-l-arabinopyranoside): white powder, C37H56O10, FAB-MS m/z: 660 [M]^+, ^13C-NMR (100 MHz, C5D5N) δc: 31.8 (t, C-1), 28.8 (t, C-2), 89.1 (d, C-3), 40.7 (s, C-4), 46.9 (d, C-5), 20.3 (t, C-6), 25.6 (t, C-7), 45.8 (d, C-8), 19.9 (s, C-9), 27.5 (s, C-10), 36.5 (t, C-11), 74.6 (d, C-12), 47.5 (s, C-13), 48.5 (s, C-14), 43.7 (t, C-15), 72.3 (d, C-16), 55.9 (d, C-17), 14.3 (q, C-18), 30.0 (t, C-19), 22.9 (d, C-20), 21.0 (q, C-21), 37.5 (t, C-22), 105.4 (s, C-23), 61.8 (d, C-24), 62.5 (s, C-25), 68.0 (t, C-26),13.0 (q, C-27), 19.8 (q, C-28), 25.5 (q, C-29), 15.0 (q, C-30), 170.9 (s, COCH3), 21.7 (q, COCH3), 104.5 (d, C-1’), 73.2 (d, C-2’), 77.2 (d, C-3’), 69.7 (d, C-4’), 63.0 (t, C-5’); 1H-NMR (400 MHz, C5D5N) δH: 0.36 (1H, d, J=4.0 Hz, H-19α), 0.70 (1H, d, J=4.0 Hz, H-19β), 0.83 (3H, s, H-30), 0.88 (3H, s, H-28), 0.94 (3H, d, J=6.5 Hz, H-21), 0.97 (3H, s, H-29), 1.37 (1H, s, H-5), 1.51 (3H, s, H-18), 1.24 (3H, s, H-27), 2.02 (3H, s, COCH3), 3.20 (1H, dd, J=4.3, 11.3 Hz, H-3), 3.33 (1H, s, H-24), 3.52 (1H, d, J=6.8 Hz, H-26), 4.02 (1H, d, J=10.4 Hz, H-26), 4.48 (1H, d, J=5.5 Hz, H-1’), 4.86(1H, t, J=8.6 Hz, H-3’)

Compound 4 (23-epi-26-deoxyactein): white powder, C37H56O10, FAB-MS m/z: 659 [M-1]^+, ^13C-NMR (100 MHz, C5D5N) δc: 31.9 (t, C-1), 29.4 (t, C-2), 88.1 (d, C-3), 41.2 (s, C-4), 47.0 (d, C-5), 20.3 (t, C-6), 25.7 (t, C-7), 45.6 (d, C-8), 20.2 (s, C-9), 26.7 (s, C-10), 36.6 (t, C-11), 77.1 (d, C-12), 47.5 (s, C-13), 48.8 (s, C-14), 44.2 (t, C-15), 74.5 (d, C-16), 56.2 (d, C-17), 14.3 (q, C-18), 29.9 (t, C-19), 23.3 (d, C-20), 21.3 (q, C-21), 37.6 (t, C-22), 105.9 (s, C-23), 62.3 (d, C-24), 62.5 (s, C-25), 68.1 (t, C-26),13.5 (q, C-27), 19.7 (q, C-28), 25.6 (q, C-29), 15.3 (q, C-30), 170.6 (s, COCH3), 21.6 (q, COCH3), 107.5 (d, C-1’), 75.6 (d, C-2’), 78.6 (d, C-3’), 71.3 (d, C-4’), 67.1 (t, C-5’);1H-NMR (400 MHz, C5D5N) δH: 0.16 (1H, d, J=4.0 Hz, H-19α), 0.51 (1H, d, J=4.0 Hz, H-19β), 0.83 (3H, s, H-28), 0.98 (3H, s, H-30), 1.01 (3H, d, J=6.5 Hz, H-21), 1.23 (1H, s, H-5), 1.29 (3H, s, H-29), 1.41 (3H, s, H-18), 1.46 (3H, s, H-27), 2.13 (3H, s,COCH3), 3.44 (1H, dd, J=4.3, 11.6 Hz, H-3), 3.66 (1H, s, H-24), 3.74 (1H, d, J=9.0 Hz, H-26), 4.04 (1H, d, J=10.4 Hz, H-26), 4.06 (1H, t, J=10.4 Hz, H-2’), 4.17 (1H, t, J=8.6 Hz, H-3’), 4.82 (1H, d, J=7.5 Hz, H-1’)

Compound 5 (cimifugin): colorless needless, C16H18O6, FAB-MS m/z: 305 [M-1]^+; ^13C-NMR (100 MHz, CD3OD) δc: 168.5 (s, C-2), 109.2 (d, C-3), 179.5 (s, C-4), 166.9 (s, C-5), 118.1 (s, C-6), 160.9 (s, C-7), 94.4 (d, C-8), 156.9 (s, C-9), 112.1 (s, C-10), 92.5 (d, C-2′), 28.7 (t, C-3′), 72.1 (s, C-4′), 25.3 (q, C-5′), 25.4 (q, C-6′), 60.9 (t, CH2OH), 61.1 (q, OCH3); 1H-NMR (400 MHz, CD3OD) δH: 1.22, 1.28 (each 3H, s, H-5′, 6′), 3.30 (2H, m, H-3′), 3.90 (3H, s, OCH3), 4.41 (2H, s, CH2OH), 4.71 (1H, t, J=8.5, 8.7Hz, H-2′), 6.17 (1H, s, H-3), 6.48 (1H, s, H-8)

Compound 6 (cimifugin glucoside): white powder, C22H28O11, FAB-MS m/z: 467 [M-1]^+; ^13C-NMR (125 MHz, CD3OD) δc: 167.1 (s, C-2), 110.9 (d, C-3), 179.6 (s, C-4), 165.1 (s, C-5), 118.5 (s, C-6), 161.1 (s, C-7), 94.6 (d, C-8), 157.0 (s, C-9), 112.4 (s, C-10), 92.7 (d, C-2′), 28.8 (t, C-3′), 72.3 (s, C-4′), 25.5 (q, C-5′), 25.4 (q, C-6′), 62.8 (t, CH2OR), 61.1 (q, OCH3), Glc: 104.1 (d, C-1), 74.9 (d, C-2), 78.2 (d, C-3), 71.6 (d, C-4), 78.0 (d, C-5), 67.3 (t, C-6); ^1H-NMR (500 MHz, CD3OD) δH: 1.30, 1.40 (each 3H, s, H-5′,6′), 3.27 (2H, m, H-3′), 3.91 (3H, s, OCH3), 4.41 (1H, d, J=7.7 Hz, H-1′), 4.74 (1H, t, J=9.0 Hz, H-2′), 6.34 (1H, s, H-3), 6.55 (1H, s, H-8)

Compound 7 (norcimifugin glucoside): yellow powder, C21H26O10, FAB-MS m/z: 454 [M]^+; ^13C-NMR (125 MHz, C5D5N) δc: 168.2 (s, C-2), 106.6 (d, C-3), 184.2 (s, C-4), 167.8 (s, C-5), 110.7 (s, C-6), 159.7 (s, C-7), 93.1 (d, C-8), 157.4 (s, C-9), 108.4 (s, C-10), 90.1 (d, C-2′), 27.3 (t, C-3′), 72.3 (s, C-4′), 25.3 (q, C-5′), 25.2 (q, C-6′), 67.4 (t, CH2OR), Glc:104.1 (d, C-1), 75.0 (d, C-2), 78.1 (d, C-3), 71.5 (d, C-4), 77.9 (d, C-5), 62.7 (t, C-6); ^1H-NMR (500 MHz, C5D5N) δH: 1.25, 1.30 (each 3H, s, H-5′,6′), 3.27 (2H, m, H-3′), 4.44 (1H, d, J=7.7 Hz, H-1′), 4.64 (1H, t, J=9.0 Hz, H-2′), 6.34 (1H, s, H-3), 6.55 (1H, s, H-8)

Compound 8 (norkhellol): colorless needless, C12H8O5, FAB-MS m/z: 232 [M]^+;13C-NMR (100 MHz, C5D5N) δc: 172.6 (s, C-2), 105.5 (d, C-3), 184.8 (s, C-4), 159.2 (s, C-5), 113.3 (s, C-6), 155.8 (s, C-7), 91.1 (d, C-8), 154.6 (s, C-9), 106.4 (s, C-10), 145.9 (d, C-2′), 104.6 (d, C-3′), 60.8 (t, CH2OH); 1H-NMR (400 MHz, C5D5N) δH: 4.75 (2H, d, J=4.8 Hz, H-3), 6.82 (1H, s, H-8), 7.16 (1H, d, J=3.0 Hz, H-3′), 7.57 (1H, s, H-3), 7.85 (1H,d, J=2.4 Hz, H-2′)

Compound 9 (25-O-acetyl-cimigenol): white powder, C32H50O6, FAB-MS m/z: 530 [M]^+, ^13C-NMR (125 MHz, C5D5N) δc: 32.7 (t, C-1), 31.2 (t, C-2), 78.1 (d, C-3), 41.2 (s, C-4), 47.3 (d, C-5), 21.4 (t, C-6), 26.5 (t, C-7), 48.8 (d, C-8), 19.7 (s, C-9), 27.0 (s, C-10), 26.6 (t, C-11), 34.1 (t, C-12), 41.9 (s, C-13), 47.5 (s, C-14), 80.2 (d, C-15), 112.5 (s, C-16), 59.5 (d, C-17), 19.6 (q, C-18), 31.3 (t, C-19), 24.0 (d, C-20), 19.6 (q, C-21), 38.0 (t, C-22), 71.8 (s, C-23), 86.8 (d, C-24), 83.2 (s, C-25), 24.1 (q, C-26), 23.4 (q, C-27), 11.9 (q, C-28), 26.2 (q, C-29), 14.9 (q, C-30), 170.3 (s, COCH3), 21.6 (q, COCH3); 1H-NMR (500 MHz, C5D5N) δH: 0.33 (1H, d, J=3.8 Hz, H-19α), 0.59 (1H, d, J=3.8 Hz, H-19β), 0.85 (3H, d, J=6.4 Hz, H-21), 1.09 (3H, s, H-29), 1.09 (3H, s, H-18), 1.15 (3H, s, H-30), 1.16 (3H, s, H-28), 1.68 (3H, s, H-27), 1.69 (3H, s, H-26), 1.96 (3H, s, COCH3), 3.53 (1H, dd, J=4.5, 11.4 Hz, H-3), 4.59 (1H, d, J=9.0 Hz, H-23)

Compound 10 (26-deoxyacetylacteol): white powder, C32H48O, FAB-MS /z + ^Citation6 m : 528 [M], ^13C-NMR (125 MHz, CD3Cl) δc: 31.9 (t, C-1), 30.2 (t, C-2),77.1 (d, C-3), 40.4 (s, C-4), 46.6 (d, C-5), 20.5 (t, C-6), 26.8 (t, C-7), 45.9 (d, C-8), 19.8 (s, C-9), 28.9 (s, C-10), 36.5 (t, C-11), 78.5 (d, C-12), 48.5 (s, C-13), 47.5 (s, C-14), 43.7 (t, C-15), 74.6 (d, C-16), 56.0 (d, C-17), 13.9 (q, C-18), 30.1 (t, C-19), 28.9 (d, C-20), 21.0 (q, C-21), 37.5 (t, C-22), 105.4 (s, C-23), 62.5 (d, C-24), 61.8 (s, C-25), 68.1 (t, C-26), 13.1 (q, C-27), 19.8 (q, C-28), 25.4 (q, C-29), 14.3 (q, C-30), 170.8 (s, COCH3), 21.7 (q, COCH3); 1H-NMR (500 MHz, C5D5N) δH: 0.34 (1H, d, J=4.4 Hz, H-19α), 0.68 (1H, d, J=4.4 Hz, H-19β), 0.79 (3H, s, H-28), 0.87 (3H, s, H-30), 0.93 (3H, d, J=6.5 Hz, H-21), 0.96 (1H, s, H-5), 1.23 (3H, s, H-29),1.26 (3H, s, H-18), 1.50 (3H, s, H-27), 2.01 (3H, s, COCH3), 3.27 (1H, dd, J=3.4, 10.8 Hz, H-3), 3.52 (1H, d, J=10.4 Hz, H-26), 4.02 (1H, d, J=10.4 Hz, H-26)

Compound 11 (acetylacteol): white powder, C32H48O7, FAB-MS m/z: 544 [M]^+; ^13C-NMR (100 MHz, C5D5N) δc: 32.2 (t, C-1), 29.9 (t, C-2), 77.7 (d, C-3), 41.0 (s, C-4), 46.9 (d, C-5), 20.7 (t, C-6), 25.7 (t, C-7), 46.0 (d, C-8), 20.0 (s, C-9), 26.2 (s, C-10), 36.9 (t, C-11), 77.3 (t, C-12), 48.8(s, C-13), 47.8 (s, C-14), 43.6 (t, C-15), 73.1 (d, C-16), 56.5 (d, C-17), 13.6(q, C-18), 29.5 (t, C-19), 26.0 (d, C-20), 21.0 (q, C-21), 37.6 (t, C-22), 105.9 (s, C-23), 63.5 (d, C-24), 65.6 (s, C-25), 98.4 (d, C-26), 13.1 (q, C-27), 19.6 (q, C-28), 25.9 (q, C-29), 14.8 (q, C-30), 170.7 (s, COCH3), 21.7 (q, COCH3). 1H-NMR (400 MHz, C5D5N) δH: 0.28 (1H, d, J=4.0 Hz, H-19α), 0.67 (1H, d, J=4.0 Hz, H-19β), 0.84 (3H, s, H-28), 0.96 (3H, d, J=7.1 Hz, H-21), 1.00 (3H, s, H-30), 1.19 (1H, s, H-5), 1.39 (3H, s, H-18), 1.78 (3H, s, H-27), 1.81 (3H, s, H-29), 2.15(3H, s, OAc), 3.48 (1H, dd, J=4.0,11.0 Hz, H-3), 3.93(1H, s, H-24), 5.73 (1H, s, H-26)

Compound 12 (25-O-methyl-cimigenol): white powder, C31H50O6, FAB-MS m/z: 501 [M]^+, ^13C-NMR (125 MHz, C5D5N) δc: 32.7 (t, C-1), 31.3 (t, C-2), 78.1 (d, C-3), 41.1 (s, C-4), 47.6 (d, C-5), 21.4 (t, C-6), 26.6 (t, C-7), 48.7 (d, C-8), 19.6 (s, C-9), 27.1 (s, C-10), 26.6 (t, C-11), 34.2 (t, C-12), 42.0 (s, C-13), 47.4 (s, C-14), 80.1 (d, C-15), 112.0 (s, C-16), 59.5 (d, C-17), 19.6 (q, C-18), 31.1 (t, C-19), 24.1 (d, C-20), 19.5 (q, C-21), 38.3 (t, C-22), 71.7 (s, C-23), 88.3 (d, C-24), 76.2 (s, C-25), 26.5 (q, C-26), 26.5 (q, C-27), 11.8 (q, C-28), 26.2 (q, C-29), 14.8 (q, C-30), 22.2 (q, OCH3); 1H-NMR (500 MHz, C5D5N) δH: 0.37 (1H, d, J=3.9 Hz, H-19α), 0.65 (1H, d, J=3.8 Hz, H-19β), 0.89 (3H, d, J=6.4 Hz, H-21), 1.10 (3H, s, H-30), 1.20 (3H, s, H-18), 1.21 (3H, s, H-29), 1.21 (3H, s, H-28), 1.26(3H, s, OCH3), 1.27 (3H, s, H-26), 1.28 (3H, s, H-27), 3.53 (1H, dd, J=4.5, 11.3 Hz, H-3), 4.59 (1H, d, J=9.0 Hz, H-23)

Compound 13 (cimigenol): white powder, C30H48O5, FAB-MS m/z: 511 [M + Na]^+, ^13C-NMR (125 MHz, CD3OD) δc: 31.9 (t, C-1), 30.7 (t, C-2), 78.2 (d, C-3), 40.2 (s, C-4), 46.8 (d, C-5), 20.7 (t, C-6), 25.8 (t, C-7), 48.0 (d, C-8), 19.5 (s, C-9), 26.5 (s, C-10), 25.0 (t, C-11), 33.4 (t, C-12), 41.0 (s, C-13), 46.7 (s, C-14), 79.6 (d, C-15), 111.2 (s, C-16), 58.8 (d, C-17), 19.0 (q, C-18), 29.6 (t, C-19), 23.3 (d, C-20), 18.8 (q, C-21), 37.5 (t, C-22), 71.5 (s, C-23), 89.1 (d, C-24), 71.0 (s, C-25), 30.4 (q, C-26), 25.0 (q, C-27), 10.7 (q, C-28), 24.1 (q, C-29), 13.7 (q, C-30); 1H-NMR (500 MHz, CD3OD) δH: 0.34 (1H, d, J=4.1 Hz, H-19α), 0.60 (1H, d, J=4.1 Hz, H-19β), 0.84 (3H, d, J=6.5 Hz, H-21), 1.09 (3H, s, H-30), 1.19 (3H, s, H-29), 1.19 (3H, s, H-18), 1.28(3H, s, H-28), 1.56 (1H, dd, J=3.4, 12.9 Hz, H-5), 2.11 (3H, s, H-26), 2.12 (3H, s, H-27), 3.20 (1H, dd, J=4.4, 10.7 Hz, H-3), 4.25 (1H, d, J=9.1 Hz, H-23)

Compound 14 (25-O-acetylcimigenol-3-O-β- -xylopyranoside): white powder, C37H58O, FAB-MS /z + 10 m : 622 [M], ^13C-NMR (100 MHz, CD3OD) δc: 32.6 (t, C-1), 30.2 (t, C-2), 89.4 (d, C-3), 41.3 (s, C-4), 47.9 (d, C-5), 21.2 (t, C-6), 26.6 (t, C-7), 48.7 (d, C-8), 20.1 (s, C-9), 26.8 (s, C-10), 26.6 (t, C-11), 34.1 (t, C-12), 42.0 (s, C-13), 47.5 (s, C-14), 80.3 (d, C-15), 112.4 (s, C-16), 59.7 (d, C-17), 19.2 (q, C-18), 29.7 (t, C-19), 24.1 (d, C-20), 19.0 (q, C-21), 38.0 (t, C-22), 70.6 (s, C-23), 87.4 (d, C-24), 83.6 (s, C-25), 24.1 (q, C-26), 21.3 (q, C-27), 11.0 (q, C-28), 25.3 (q, C-29), 14.8 (q, C-30), 171.5 (s, COCH3), 21.6 (q, COCH3), 106.5 (d, C-1’), 74.7 (d, C-2’), 77.2 (d, C-3’), 72.2 (d, C-4’), 65.9 (t, C-5’); 1H-NMR (400 MHz, CD3OD) δH: 0.39 (1H, d, J=3.5 Hz, H-19α), 0.65 (1H, d, J=3.5 Hz, H-19β), 0.88 (3H, d, J=6.5 Hz, H-21), 0.90 (3H, s, H-30), 1.00 (3H, s, H-28), 1.03 (3H, s, H-18), 1.11 (3H, s, H-29), 1.40 (3H, s, H-26), 1.47 (3H, s, H-27), 1.95 (3H, s, COCH3), 3.21 (1H, t, J=6.5 Hz, H-2’), 3.30 (1H, t, J=6.9 Hz, H-3’), 3.82 (1H, dd, J=5.0, 9.7 Hz, H-3), 4.30 (1H, d, J=7.1 Hz, H-23), 4.39 (1H, d, J=5.9 Hz, H-1’), 4.47 (1H, dd, J=8.9, 18.0 Hz, H-4’) D

Compound 15 (24-O-acetylhydroshengmanol-3-O-β-d-xylopyranoside): white powder, C37H60O11, FAB-MS m/z: 679 [M-1]^+, ^13C-NMR (100 MHz, CD3OD) δc: 32.5 (t, C-1), 30.1 (t, C-2), 89.1 (d, C-3), 41.2 (s, C-4), 47.5 (d, C-5), 20.8 (t, C-6), 27.0 (t, C-7), 52.7 (d, C-8), 19.6 (s, C-9), 27.0 (s, C-10), 27.0 (t, C-11), 37.1 (t, C-12), 48.9 (s, C-13), 49.5 (s, C-14), 86.6 (d, C-15), 105.0 (s, C-16), 70.6 (d, C-17), 19.6 (q, C-18), 31.3 (t, C-19), 34.1 (d, C-20), 21.0 (q, C-21), 43.0 (t, C-22), 74.8 (s, C-23), 82.7 (d, C-24), 84.0 (s, C-25), 25.2 (q, C-26), 26.9 (q, C-27), 13.3 (q, C-28), 23.7 (q, C-29), 14.7 (q, C-30), 171.9 (s, COCH3), 20.2 (q, COCH3), 106.7 (d, C-1’), 77.3 (d, C-2’), 77.8 (d, C-3’), 72.4 (d, C-4’), 66.0 (t, C-5’); 1H-NMR (400 MHz, CD3OD) δH: 0.17 (1H, d, J=4.0 Hz,H-19α), 0.50 (1H, d, J=4.0 Hz, H-19β), 0.83 (3H, s, H-30), 0.98 (3H, s, H-28), 1.30 (3H, s, H-18), 1.34 (3H, s, H-29), 1.33 (3H, d, J=7.6 Hz, H-21), 1.68 (3H, s, H-26), 1.74 (3H, s, H-27), 2.06 (3H, s, COCH3), 4.20 (1H, s, H-15), 4.84 (1H, d, J=7.5 Hz, H-1’)

Compound 16 (26-deoxyactein): colorless needles, C37H56O10, FAB-MS m/z: 660 [M]^+, ^13C-NMR (100 MHz, C5D5N) δc: 31.9 (t, C-1), 29.9 (t, C-2), 88.1 (d, C-3), 41.2 (s, C-4), 46.9 (d, C-5), 20.1 (t, C-6), 25.9 (t, C-7), 45.8 (d, C-8), 20.4 (s, C-9), 26.7 (s, C-10), 36.7 (t, C-11), 77.0 (d, C-12), 48.2 (s, C-13), 47.9 (s, C-14), 43.7 (t, C-15), 73.0 (d, C-16), 56.4 (d, C-17), 13.8 (q, C-18),29.5 (t, C-19), 25.7 (d, C-20), 21.0 (q, C-21), 36.7(t, C-22), 105.9 (s, C-23), 63.3 (d, C-24), 63.3 (s, C-25), 68.7 (t, C-26),13.5 (q, C-27), 19.5 (q, C-28), 25.5 (q, C-29), 15.3 (q, C-30), 170.6 (s, COCH3), 21.7 (q, COCH3), 107.6 (d, C-1’), 76.0 (d, C-2’), 78.7 (d, C-3’), 71.3 (d, C-4’), 67.2 (t, C-5’); 1H-NMR (400 MHz, C5D5N) δH: 0.17 (1H, d, J=3.8 Hz, H-19α), 0.52 (1H, d, J=3.8 Hz, H-19β), 0.97 (3H, s, H-30), 0.83 (3H, s, H-28), 1.00 (3H, d, J=6.5 Hz, H-21), 1.28 (3H, s, H-29), 1.23 (1H, s, H-5), 1.40 (3H, s, H-18), 1.24 (3H, s, H-27), 2.02 (3H, s, COCH3), 3.44 (1H, dd, J=3.4, 10.8 Hz, H-3), 3.33 (1H, s, H-24), 3.62 (1H, d, J=9.0 Hz, H-26), 4.02 (1H, d, J=10.4 Hz, H-26), 4.82 (1H, d, J=7.5 Hz, H-1’), 4.10 (1H, t, J=8.6 Hz, H-3’)

Abbreviation: NMR, nuclear magnetic resonance.

NianYZhangYLChenJCLuLQiuMHQingCCytotoxic chemical constituents from the roots of Cimicifuga foetida. [corrected]J Nat Prod2010732939820121210

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