Structure of securinine

Saito, Seiichi; Kotera, K.; Shigematsu, Nobuharu; Ide, Akio; Sugimoto, Norihiko; Horii, Zen-ichi; Hanaoka, Miyoji; Yamawaki, Yasuhiko; Tamura, Yasumitsu

doi:10.1016/0040-4020(63)85024-3

Cited by 48 publications

(40 citation statements)

References 22 publications

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“…The molecular formula of 7 was determined as C 12 (8), 6,7) indicating that 7 was a dihydronorsecurinine type alkaloid with a hydroxyl group. The position of hydroxyl group was assigned by the HMBC correlations between H-14 (d H 4.24) and C-6 (d C 66.0), C-7 (d C 29.5) and C-12 (d C 172.9) (Fig.…”

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confidence: 99%

“…1) Previous phytochemical investigations had led to the isolation of a number of Securinega alkaloids, [1][2][3][4][5][6][7][8] which exhibited antimalarial, antibacterial and antitumor activities. [8][9][10][11] Among the Securinega alkaloids, securinine was a major alkaloid obtained from the plant Securinega suffruticosa, 12) and clinically applied to treat sequela of poliomyelitis and aplastic anemia. 13) Pharmacology investigations indicated that securinine was a stereospecific GABA A receptor antagonist with a significant central nervous system (CNS) activity.…”

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Securinega Alkaloids from Flueggea leucopyra

Wang

Zhang

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Six new Securinega alkaloids (1, 3, 5, 7, 9, 10) together with four known ones were isolated from the twigs and leaves of Flueggea leucopyra. The structures of new compounds were established on the basis of the spectroscopic methods including UV, IR, HR-electrospray ionization (ESI)-MS, 1D and 2D NMR, and the absolute configurations of these new alkaloids were assigned by the modified Mosher's method and the circular dichroism (CD) spectra.

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confidence: 99%

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confidence: 99%

Securinega Alkaloids from Flueggea leucopyra

Wang

Zhang

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…However, the a,b-double bond of 14,15-dihydrosecurinine remained intact in this condition. In contrast, securinine was reduced to tetrahydrosecurinine by using sodium borohydride (NaBH 4 ) (Saito et al 1963). Therefore, selective hydrogenation of c,d-double bond of securinine can be achieved by using Aspergillus sp.…”

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confidence: 98%

Newly Detected Specific Hydrogenation of the Conjugated Double Bond of Unsaturated Alkaloid Lactones by Aspergillus sp.

et al. 2005

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“…Securinine was initially isolated from Securinega suffruticosa by Russian scientists in 1956 (4). Its structure was determined by chemical and spectroscopic studies in 1963 (5) and was verified by X-ray crystallography in 1965 (6). There are two optical isomers, L-securinine and D-securinine, with the pharmacological activity of D-securinine being weaker (by ~10%) than that of L-securinine (7).…”

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confidence: 99%

L-securinine induces apoptosis in the human promyelocytic leukemia cell line HL-60 and influences the expression of genes involved in the PI3K/AKT/mTOR signaling pathway

Han

Zhang

et al. 2014

Oncology Reports

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Abstract.The Securinega alkaloids are a class of natural products isolated from plants of the Euphorbiaceae family. L-securinine induces apoptosis in the human promyelocytic leukemia cell line HL-60 indicating its potential as an efficient natural antitumor drug with low toxicity. The aim of the present study was to investigate the apoptotic effects of L-securinine on HL-60 cells and to explore its potential underlying molecular mechanism(s) as an antitumor agent. HL-60 cells were cultured with L-securinine. The proliferation and changes in cell morphology were evaluated by Cell Counting Kit-8 (CCK-8) assay and electron microscopy, respectively. Induction of apoptosis and cell cycle progression were investigated by flow cytometry. The PI3K/AKT/mTOR pathway gene expression was measured by quantitative PCR (qPCR). L-securinine decreased the viability of HL-60 cells in a dose-and time-dependent manner, with IC 50 values at 24, 48 and 72 h post-treatment of 47.88, 23.85 and 18.87 µmol/l, respectively. Numerous apoptotic bodies were observed in the HL-60 cells treated with 25 µmol/l L-securinine for 48 h. L-securinine at 12.5, 25 and 50 µmol/l increased the rate of apoptosis in HL-60 cells, and G1/S phase progression was retarded. Furthermore, L-securinine induced downregulation of PI3K, AKT and mTOR gene expression and upregulation of PTEN gene expression in a dose-dependent manner. In conclusion, L-securinine induces apoptosis and inhibition of cell cycle progression in HL-60 cells by modulation of the PI3K/ AKT/mTOR pathway gene expression. These observations indicate the potential of L-securinine as an antitumor agent.

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Structure of securinine

Cited by 48 publications

References 22 publications

Securinega Alkaloids from Flueggea leucopyra

Securinega Alkaloids from Flueggea leucopyra

Newly Detected Specific Hydrogenation of the Conjugated Double Bond of Unsaturated Alkaloid Lactones by Aspergillus sp.

L-securinine induces apoptosis in the human promyelocytic leukemia cell line HL-60 and influences the expression of genes involved in the PI3K/AKT/mTOR signaling pathway

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