Swerilactones C and D, anti-HBV New Lactones from a Traditional Chinese Herb: Swertia mileensis

Author:

Geng Chang-An1,Zhang Xue-Mei1,Shen Yong1,Zuo Ai-Xue1,Liu Ji-Feng1,Ma Yun-Bao1,Luo Jie1,Zhou Jun1,Jiang Zhi-yong1,Chen Ji-Jun1

Affiliation:

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PRC, and Graduate School of Chinese Academy of Sciences, Beijing 100039, PRC

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Reference13 articles.

1. Swerilactones A and B, Anti-HBV New Lactones from a Tradtional Chinese Herb: Swertia mileensis as a Treatment for Viral Hepatitis

2. Compound1: mp 255−256 °C; [α]28.2D+14.66 (c0.20, CHCl3/MeOH v/v = 3:1); UV (MeOH) λmax(log ε) 377 (3.14), 256 (4.32) nm; IR (KBr) λ́max: 3455, 1717, 1644, 1434, 1394, 1355, 1176, 1089, 1062, 1031, 983, 808 cm−1;1H and13C NMR data, see Table1; EIMSm/z388 ([M]+, 1), 370 (41), 253 (23), 195 (100), 177 (72), 165 (47), 149 (59); ESIMS (−)m/z423 ([M + Cl]−); HRESIMS (−)m/z423.0843 [M + Cl]−(C20H20O8Cl calcd 423.0846).

3. Crystallographic data of compound1: C20H20O8, MW = 388.36; monoclinic, space groupp21;a= 6.547(2) Å,b= 10.892(3) Å,c= 12.418(4) Å, α = 90.00, β = 103.542(4), γ = 90.00,V= 860.9(5) Å3,Z= 2,d= 1.498 g/cm3, crystal dimensions 0.16 × 0.12 × 0.08 nm3were used for measurement on a SHELXL-97 with a graphite monochromater, Mo Kα radiation. The total number of reflections measured was 3852, of which 1635 were observed,I> 2σ(I). Final indices:R1= 0.0681, wR2= 0.1487. The crystal structure of compound1was solved by direct method SHLXS-97 (Sheldrick, 1990) and expanded using the difference Fourier technique, refined by the program SHLXL-97 (Sheldrick, 1997), and the full-matrix least-squares calculations. Crystallographic data for the structure of compound1have been deposited with the Cambridge Crystallographic Data Centre (deposition no. CCDC 732831). Copies of these data can be obtained free of charge viawww.ccdc.cam.ac.uk/conts/retrieving.htm. (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, U.K.; fax (+44) 1223-336-033; or desposit@ccdc.cam.ac.uk).

4. Compound2: mp 240−241 °C; [α]28.9D−12.90 (c0.22, CHCl3/MeOH v/v = 1:1); UV (MeOH) λmax(log ε) 262 (4.23) nm; IR (KBr) λ́max3334, 1727, 1701, 1660, 1637, 1449, 1407, 1316, 1177, 1090, 1067, 1030, 982, 809 cm−1;1H and13C NMR data, see Table1; ESIMS (−)m/z387 ([M − H]−); (−) HRESIMSm/z387.1079 [M − H]−(C20H19O8calcd 387.1079).

5. Crystallographic data of compound2: C20H20O8(H2O), MW = 406.38; triclinic, space groupp1;a= 8.6844(14) Å,b= 14.094(2) Å,c= 17.000(3) Å, α = 73.293(2), β = 87.688(2), γ = 72.958(2),V= 1903.2(5) Å3,Z= 4,d= 1.418 g/cm3, crystal dimensions 0.20 × 0.14 × 0.08 nm3were used for measurement on a SHELXL-97 with a graphite monochromater, Mo Kα radiation. The total number of reflections measured was 8035, of which 3235 were observed,I> 2σ(I). Final indices:R1= 0.0409, wR2= 0.1000. The crystal structure of compound2was solved by direct method SHLXS-97 (Sheldrick, 1990) and expanded using the difference Fourier technique, refined by the program SHLXL-97 (Sheldrick, 1997), and the full-matrix least-squares calculations. Crystallographic data for the structure of compound2have been deposited with the Cambridge Crystallographic Data Centre (deposition no. CCDC 737797). Copies of these data can be obtained free of charge viawww.ccdc.cam.ac.uk/conts/retrieving.htm(or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, U.K.; fax (+44) 1223-336-033; or desposit@ccdc.cam.ac.uk).

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