ABSTRACT
Five undescribed monoterpene-chalcone conjugates (1-5), one undescribed hypothetical precursor of diarylheptanoid (6), two undescribed diarylheptanoids (7-8), and fourteen known compounds (9-22) were isolated from the seeds of Alpinia katsumadai. Their structures were elucidated through the interpretation of HRESIMS, NMR, ECD, and X-ray diffraction data. MTT assays on human cancer cell lines (HepG2, A549, SGC7901, and SW480) revealed that compounds 3-8, 11, and 13 exhibited broad-spectrum antiproliferative activities with IC50 values ranging from 3.59 to 21.78 µM. B cell lymphoma 2 was predicted as the target of sumadain C (11) by network pharmacology and verified by homogeneous time-resolved fluorescence assay and molecular docking.
Subject(s)
Alpinia , Antineoplastic Agents, Phytogenic , Cell Proliferation , Diarylheptanoids , Drug Screening Assays, Antitumor , Monoterpenes , Seeds , Alpinia/chemistry , Humans , Diarylheptanoids/chemistry , Diarylheptanoids/pharmacology , Diarylheptanoids/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Seeds/chemistry , Molecular Structure , Cell Proliferation/drug effects , Monoterpenes/chemistry , Monoterpenes/isolation & purification , Monoterpenes/pharmacology , Structure-Activity Relationship , Chalcones/chemistry , Chalcones/pharmacology , Chalcones/isolation & purification , Chalcone/chemistry , Chalcone/pharmacology , Chalcone/isolation & purification , Cell Line, Tumor , Dose-Response Relationship, Drug , Molecular Docking SimulationABSTRACT
A new kavalactone, 4'-hydroxyl dihydro-5, 6-dehydrokavain (1) was isolated from the petroleum ether partition of leaves of Alpinia zerumbet (Pers.) Burtt. et Smith, together with four known kavalactone dimers, rel-1,trans-3-bis-(4-methoxy-2-oxopyran-6-yl)-cis-2,trans-4-diphenyl cyclobutene (2), aniba dimer A (3), aniba dimer C (4), 6,6'-(3,4-diphenylcyclobutane-1,2-diyl)bis(4-methoxy-2H-pyran-2-one (5). The structure of compound 1 was characterized by its MS, 1D-NMR, and 2D-NMR data, and the structures of the known compounds were determined by comparison of their spectroscopic data with those reported by the literatures. The obtained compounds were evaluated for their protective activities on human umbilical vein endothelial cells (HUVECs) damaged by high glucose (35 mM, cell viability at 70.10%). Compounds 3 and 5 could increase the cell viability at the concentration of 12.5 µΜ (83.12%) and 25 µΜ (75.02%), whereas at the concentration of 12.5 µΜ, compounds 1, 2, and 4 didn't reverse cell damage (cell viability at 38.58%, 54.80% and 58.16%).
