Ten previously undescribed glycosides, carissaedulosides A-J (1-10) referring to six apiosylated phenylpropanoids (1-6), one coumarin-secoiridoid hybrid (7), and three furofuran lignans (8-10) were isolated from the root barks of Carissa edulis, together with 13 known analogues (11-23). Their structures were elucidated by spectroscopic analysis, ECD computational methods, and chemical derivations for configurations of sugar moieties. The new lignan bisdesmoside, 10, exhibited significant cytotoxicity against A549 (IC = 3.87 ± 0.03 μM) and MCF-7 (IC = 9.231 ± 0.290 μM) cell lines, while the known lignan monodesmoside, 12, showed impressive cytotoxic efficacy (IC = 5.68 ± 0.180 μM) against only MCF-7 cell line. It is noted that a known cardenolide, 11, displayed strong cytotoxic potency against HL-60, A549, MCF-7 and SW480 cell lines with IC values ranging from 0.023 to 0.137 μM. Moreover, compound 11 induced dose-dependent apoptosis on SW480 cell, but not explicit dose-dependent apoptosis on HL-60 cells.
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http://dx.doi.org/10.1016/j.bioorg.2020.104097 | DOI Listing |
Bioorg Chem
September 2020
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China. Electronic address:
Ten previously undescribed glycosides, carissaedulosides A-J (1-10) referring to six apiosylated phenylpropanoids (1-6), one coumarin-secoiridoid hybrid (7), and three furofuran lignans (8-10) were isolated from the root barks of Carissa edulis, together with 13 known analogues (11-23). Their structures were elucidated by spectroscopic analysis, ECD computational methods, and chemical derivations for configurations of sugar moieties. The new lignan bisdesmoside, 10, exhibited significant cytotoxicity against A549 (IC = 3.
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