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Published October 31, 2022 | Version v1
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Artemidubolides A T, cytotoxic unreported guaiane-type sesquiterpenoid dimers against three hepatoma cell lines from Artemisia dubia

Authors/Creators

  • 1. * & State Key Laboratory of Phytochemistry and Plant Resources in West China, Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, & * & University of Chinese Academy of Sciences, Beijing, 100049, People's Republic of China

Description

Gao, Zhen, Ma, Wen-Jing, Li, Tian-Ze, Ma, Yun-Bao, Hu, Jing, Huang, Xiao-Yan, Geng, Chang-An, He, Xiao-Feng, Zhang, Xue-Mei, Chen, Ji-Jun (2022): Artemidubolides A T, cytotoxic unreported guaiane-type sesquiterpenoid dimers against three hepatoma cell lines from Artemisia dubia. Phytochemistry (113299) 202: 1-17, DOI: 10.1016/j.phytochem.2022.113299, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113299

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urn:lsid:plazi.org:pub:F75EFFF12B1FFFE1FFE1FF83FFB5FFB3

Has part
Figure: 10.5281/zenodo.8237059 (DOI)
Figure: 10.5281/zenodo.8237061 (DOI)
Figure: 10.5281/zenodo.8237063 (DOI)
Figure: 10.5281/zenodo.8237065 (DOI)
Figure: 10.5281/zenodo.8237067 (DOI)
Figure: 10.5281/zenodo.8237069 (DOI)
Figure: 10.5281/zenodo.8237071 (DOI)
Figure: 10.5281/zenodo.8237073 (DOI)
Figure: 10.5281/zenodo.8237075 (DOI)

References

  • Artemidubolide A (1): monoclinic crystals (H2O-MeOH-CHCl3, 0.1:10:90); mp 198-199 °C; [α]+44.2 (c 0.104, MeOH); ECD (MeOH) λ max (Δ ε) 200 ( 9.80), 218 (+10.91) nm; IR v max 3498, 1762, 1723, 1666, 1376, 1254, 1222, 1074 cm 1; 1H and 13C NMR data see Tables 1 and 4; (+)-HRESIMS m/z 515.2396 ([M + Na]+, calcd for C30H36O6Na, 515.2404).
  • Artemidubolide B (2): orthorhombic crystals (H2O-MeOH-CHCl3, 0.1:10:90); mp 200-201 °C; [α] +52.1 (c 0.11, MeOH); ECD (MeOH) λ max (Δ ε) 201 ( 19.76), 217 (+16.55) nm; IR v max 3446, 1769, 1752, 1665, 1378, 1254, 1211, 1078 cm 1; 1H and 13C NMR data see Tables 1 and 4; (+)-HRESIMS m/z 515.2404 ([M + Na]+, calcd for C30H36O6Na, 515.2404).
  • Artemidubolide C (3): white amorphous powder; [α] +38.5 (c 0.10, MeOH); ECD (MeOH) λ max (Δ ε) 212 (+11.83) nm; IR v max 3450, 1765, 1632, 1448, 1382, 1229, 1150, 1059 cm 1; 1H and 13C NMR data see Tables 1 and 4; (+)-HRESIMS m/z 493.2591 ([M + H]+, calcd for C30H37O6, 493.2585).
  • Artemidubolide D (4): orthorhombic crystals (H2O-MeOH-CHCl3, 0.1:10:90); mp 201-202 °C; [α] +67.8 (c 0.11, MeOH); ECD (MeOH) λ max (Δ ε) 197 ( 28.87), 215 (+20.23) nm; IR v max 3437, 1757, 1743, 1649, 1461, 1384, 1306, 1201, 1065 cm 1; 1H and 13C NMR data see Tables 1 and 4; (+)-HRESIMS m/z 493.2566 ([M + H]+, calcd for C30H37O6, 493.2585).
  • Artemidubolide E (5): white amorphous powder; (MeOH-CHCl3, 95:5); [α] +83.3 (c 0.10, MeOH); ECD (MeOH) λ max (Δ ε) 217 (18.27) nm; IR v max 3448, 1770, 1732, 1660, 1448, 1380, 1256, 1115, 1007 cm 1; 1H and 13C NMR data see Tables 1 and 4; (+)-HRESIMS m/z 493.2581 ([M + H]+, calcd for C30H37O6, 493.2585).
  • Artemidubolide F (6): orthorhombic crystals (H2O-MeOH-CHCl3, 0.1:10:90); mp 202-203 °C; [α] +104.2 (c 0.12, MeOH); ECD (MeOH) λ max (Δ ε) 217 (+11.85) nm; IR v max 3469, 1780, 1732, 1635, 1448, 1305, 1292, 1200, 1078 cm 1; 1H and 13C NMR data see Tables 1 and 4; (+)-HRESIMS m/z 495.2751 ([M +H]+, calcd for C30H39O6, 495.2741).
  • Artemidubolide G (7): white amorphous powder; [α] 11.5 (c 0.08, MeOH); ECD (MeOH) λ max (Δ ε) 201 ( 7.92), 216 (+12.25) nm; IR v max 3486, 1755, 1638, 1451, 1384, 1223, 1078 cm 1; 1H and 13C NMR data see Tables 1 and 4; (+)-HRESIMS m/z 493.2568 ([M + H]+, calcd for C30H37O6, 493.2585).
  • Artemidubolide H (8): white amorphous powder; [α] +103.3 (c 0.09, MeOH); ECD (MeOH) λ max (Δ ε) 204 (+12.46), 222 (+16.49) nm; IR v max 3542, 1762, 1665, 1389, 1313, 1141, 1109 cm 1 ; 1 H and 13C NMR data see Tables 2 and 4; ( )-HRESIMS m/z 555.2599 ([M + HCOO]-, calcd for C31H39O9, 555.2600).
  • Artemidubolide I (9): white amorphous powder; [α] +44.3 (c 0.10, MeOH); ECD (MeOH) λ max (Δ ε) 216 (+14.37) nm; IR v max 3433, 1757, 1635, 1444, 1384, 1256, 1152 cm 1; 1H and 13C NMR data see Tables 2 and 4; ( )-HRESIMS m/z 555.2548 ([M +HCOO]-, calcd for C31H39O9, 555.2600).
  • Artemidubolide J (10): white amorphous powder; [α] +29.8 (c 0.11, MeOH); ECD (MeOH) λ max (Δ ε) 197 (+7.78), 263 ( 18.27) nm; IR v max 1770, 1687, 1618, 1444, 1259, 1146, 1013 cm 1; 1H NMR and 13C NMR data see Tables 2 and 4; (+)-HRESIMS m/z 505.2573 ([M + H]+, calcd for C31H37O6, 505.2585).
  • Artemidubolide K (11): orthorhombic crystals (H2O-MeOH-CHCl3, 0.1:10:90); mp 204-205 °C; [α] 31.3 (c 0.10, MeOH); ECD (MeOH) λ max (Δ ε) 198 (+9.89) nm; IR v max 3459, 1766, 1744, 1626, 1458, 1257, 1132, 1019 cm 1; 1H and 13C NMR data see Tables 2 and 5; (+)-HRESIMS m/z 493.2571 ([M + H]+, calcd for C30H37O6, 493.2585).
  • Artemidubolide L (12): white amorphous powder; [α] 53.1 (c 0.10, MeOH); ECD (MeOH) λ max (Δ ε) 226 ( 3.78) nm; IR v max 3501, 1766, 1638, 1321, 1264, 1232, 1152 cm 1; 1H and 13C NMR data see Tables 2 and 5; ( )-HRESIMS m/z 537.2475 ([M +HCOO]-, calcd for C31H37O8, 537.2494.
  • Artemidubolide M (13): white amorphous powder; [α] 23.1 (c 0.09, MeOH); ECD (MeOH) λ max (Δ ε) 212 ( 13.09) nm; IR v max 3459, 1759, 1665, 1320, 1266, 1246, 1196 cm 1; 1H and 13C NMR data see Tables 2 and 5; (+)-HRESIMS m/z 493.2591 ([M + H]+, calcd for C30H37O6, 493.2585).
  • Artemidubolide N (14): white amorphous powder; [α] 35.1 (c 0.10, MeOH); ECD (MeOH) λ max (Δ ε) 210 ( 16.78) nm; IR v max 3437, 1753, 1631, 1317, 1268, 1243, 1196 cm 1; 1H and 13C NMR data see Tables 2 and 5; ( )-HRESIMS m/z 555.2605 [M +HCOO]-, calcd for C31H39O9, 555.2600).
  • Artemidubolide O (15): orthorhombic crystals (H2O-MeOH-CHCl3, 0.1:10:90); mp 195-196 °C; [α] 66.7 (c 0.11, MeOH); ECD (MeOH) λ max (Δ ε) 217 ( 5.92), 243 (+2.43), 272 ( 2.06) nm; IR v max 3487, 1774, 1683, 1320, 1264, 1238, 1200 cm 1 ; 1 H and 13C NMR data see Tables 3 and 5; (+)-HRESIMS m/z 491.2436 ([M + H]+, calcd for C30H35O6, 491.2428).
  • Artemidubolide P (16): white amorphous powder; [α] +36.0 (c 0.12, MeOH); ECD (MeOH) λ max (Δ ε) 212 ( 15.89) nm; IR v max 3477, 1762, 1634, 1405, 1232, 1068 cm 1; 1H and 13C NMR data see Tables 3 and 5; (+)-HRESIMS m/z 491.2410 ([M +H]+, calcd for C30H35O6, 491.2428).
  • Artemidubolide Q (17): white amorphous powder; [α] +138.6 (c 0.10, MeOH); ECD (MeOH) λ max (Δ ε) 207 (+23.10), 226 ( 1.69), 246 (+3.91) nm; IR v max 3467, 1764, 1640, 1402, 1348, 1227, 1033 cm 1; 1H and 13C NMR data see Tables 3 and 5; ( )-HRESIMS m/z 535.2332, ([M + HCOO]-, calcd for C31H35O8, 535.2337).
  • Artemidubolide R (18): monoclinic crystals (H2O-MeOH-CHCl3, 0.1:10:90); mp 210-211 °C; [α] 1.30 (c 0.11, MeOH); ECD (MeOH) λ max (Δ ε) 210 ( 32.78) nm; IR v max 3461, 1760, 1702, 1631, 1223, 1153 cm 1; 1H and 13C NMR data see Tables 3 and 5; (+)-HRESIMS m/z ( )-HRESIMS ion peak at m/z 577.3024 ([M + HCOO]-, calcd for C31H45O10, 577.3018).
  • Artemidubolide S (19): white amorphous powder; [α] +56.0 (c 0.12, MeOH); ECD (MeOH) λ max (Δ ε) 205 ( 5.51) nm; IR v max 3427, 1757, 1711, 1669, 1625, 1382, 1258, 1156 cm 1 ; 1 H and 13C NMR data see Tables 3 and 5; (+)-HRESIMS m/z 551.2624 ([M + Na] + , calcd for C30H40O8Na, 551.2615).
  • Artemidubolide T (20): white amorphous powder; [α] 94.4 (c 0.11, MeOH); ECD (MeOH) λ max (Δ ε) 209 ( 12.12) nm; IR v max 3429, 1760, 1710, 1639, 1378, 1262, 1041 cm 1; 1H and 13C NMR data see Tables 3 and 5; (+)-HRESIMS m/z 551.2616 ([M +Na]+, calcd for C30H40O8Na, 551.2615).