Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. 2018

Si-Yuan Zhou, and Ting-Lan Zhou, and Guofu Qiu, and Xiajuan Huan, and Ze-Hong Miao, and Sheng-Ping Yang, and Shugeng Cao, and Fengkai Fan, and You-Sheng Cai
Institute of TCM and Natural Products, School of Pharmaceutical Sciences, Wuhan University, Wuhan, P. R. China.

Three new bisindole alkaloids, 3'-(2-oxopropyl)-19,20-dihydrotabernamine (1: ), 3'-(2-oxopropyl)-ervahanine B (2: ), 19,20-dihydrovobparicine (3: ), and 20 known compounds were isolated from the aerial parts of Tabernaemontana bufalina. The structures of these alkaloids were elucidated using spectroscopic methods. The absolute configurations of 1: -3: were determined by the circular dichroic exciton chirality method. Compounds 1: -23: were screened for their cytotoxicity against two human cancer cell lines, A-549 and MCF-7. Ten compounds (1: -3, 10, 14, 16, 17, 19, 22: , and 23: ) exhibited inhibitory effects against the two human cancer cells with IC50 values of 1.19 ~ 6.13 µM.

UI MeSH Term Description Entries
D008961 Models, Structural A representation, generally small in scale, to show the structure, construction, or appearance of something. (From Random House Unabridged Dictionary, 2d ed) Model, Structural,Structural Model,Structural Models
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D001952 Bridged-Ring Compounds Cyclic hydrocarbons that contain multiple rings which share one or more bridgehead connections. Bridged Compounds,Bridged Ring Compounds
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D045744 Cell Line, Tumor A cell line derived from cultured tumor cells. Tumor Cell Line,Cell Lines, Tumor,Line, Tumor Cell,Lines, Tumor Cell,Tumor Cell Lines
D020128 Inhibitory Concentration 50 The concentration of a compound needed to reduce population growth of organisms, including eukaryotic cells, by 50% in vitro. Though often expressed to denote in vitro antibacterial activity, it is also used as a benchmark for cytotoxicity to eukaryotic cells in culture. IC50,Concentration 50, Inhibitory
D026121 Indole Alkaloids Group of alkaloids containing a benzylpyrrole group (derived from TRYPTOPHAN). Indole Alkaloid,Alkaloid, Indole,Alkaloids, Indole
D030014 Tabernaemontana A plant genus of the family APOCYNACEAE that contains bisindole alkaloids and IBOGAINE. Anartia Plant,Bonafousia,Ervatamia,Iboga,Muntafara,Pagiantha,Peschiera,Pterotaberna,Reichardia,Sarcopharyngia,Stemmadenia,Taberna Plant,Tabernaemontaneae,Tabernanthe iboga,Anartia Plants,Bonafousias,Ervatamias,Ibogas,Muntafaras,Pagianthas,Peschieras,Plant, Taberna,Pterotabernas,Reichardias,Sarcopharyngias,Stemmadenias,Taberna Plants,Tabernaemontanas
D035261 Plant Components, Aerial The above-ground plant without the roots. Aerial Parts, Plant,Aerial Plant Components,Aerial Part, Plant,Aerial Plant Component,Component, Aerial Plant,Components, Aerial Plant,Part, Plant Aerial,Parts, Plant Aerial,Plant Aerial Part,Plant Aerial Parts,Plant Component, Aerial
D039821 Monoterpenes Compounds with a core of 10 carbons generally formed via the mevalonate pathway from the combination of 3,3-dimethylallyl pyrophosphate and isopentenyl pyrophosphate. They are cyclized and oxidized in a variety of ways. Due to the low molecular weight many of them exist in the form of essential oils (OILS, VOLATILE). Monoterpene,Monoterpenoid,Monoterpenoids

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