Cytotoxicity of Aporphine, Protoberberine, and Protopine Alkaloids from <i>Dicranostigma leptopodum</i> (Maxim.) Fedde

Sun, Ruiqi; Jiang, Haiyan; Zhang, Wenjuan; Yang, Kai; Wang, Chengfang; Fan, Li Qun; He, Qing; Feng, Jiang-Bin; Du, Shu-Shan; Deng, Zhiwei; Geng, Zhu‐Feng

doi:10.1155/2014/580483

Cited by 16 publications

(9 citation statements)

References 33 publications

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“…The aporphine scaffold is endowed with a range of biological activities including antiplatelet, , cytotoxicity, − antiplasmoidal, antimicrobial, , and antiviral activities. , As far as activity at central nervous system (CNS) receptors is concerned, aporphines have been most studied as ligands for dopamine (D 1 , D 2 , and D 3 ), − serotonin (5-HT 1A , 5-HT 2A , and 5-HT 7 ), − and alpha-adrenergic receptors (α 1A , α 1B , and α 1D ). ,− These receptors are known to play important roles in a myriad of neuropsychiatric disorders and drug abuse. The rich pharmacology of aporphines presents attractive yet challenging opportunities to optimize this naturally occurring scaffold for activity at CNS receptors.…”

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confidence: 99%

Semisynthetic Studies on and Biological Evaluation of N-Methyllaurotetanine Analogues as Ligands for 5-HT Receptors

Madapa

Harding

2015

J. Nat. Prod.

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N-Methyllaurotetanine (1) has been reported to display good affinity for the 5-HT1A receptor, but no structure-affinity studies have been performed to date. The commercially available alkaloid boldine (2) was used as the starting material for synthesis of various C-9 alkoxy analogues of N-methyllaurotetanine in order to gauge the effect of C-9 alkylation on affinity and selectivity at 5-HT1A, 5-HT2A, and 5-HT7 receptors. Mitsunobu reactions were implemented in the alkylation steps leading to the analogues. Modest improvement in 5-HT1A affinity was observed upon alkylation for most analogues. Thus, the C-9 hydroxy group of 1 is not critical for affinity to the 5-HT1A receptor. Some analogues displayed high affinity for the 5-HT7 receptor, comparable to N-methyllaurotetanine, with moderate selectivity vs 5-HT1A and 5-HT2A receptors.

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confidence: 99%

Semisynthetic Studies on and Biological Evaluation of N-Methyllaurotetanine Analogues as Ligands for 5-HT Receptors

Madapa

Harding

2015

J. Nat. Prod.

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“…In fact, some of these alkaloids have been previously reported as cytotoxic agents. 27,[29][30][31] Moreover, the cytotoxicity of the mixture 6, 9 and 10 may due to the presence of the compound 9, which has reported with a potent cytotoxic activity. 31 Among the alkaloids evaluated, (+)-nornuciferine (1), and the mixture of 6, 9 and 10 displayed promising cytotoxicity activities with IC 50 values below to 17.0 µmol L -1 against HepG2, HL and K562.…”

Section: Resultsmentioning

confidence: 99%

ALKALOIDS FROM LEAVES OF Guatteria pogonopus (ANNONACEAE) AND THEIR CYTOTOXICITIES

et al. 2018

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The phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatteria pogonopus Mart. (Annonaceae) allowed the isolation and identification for the first time in this species of: (+)-nornuciferine (1), a mixture of 1 and (+)-anonaine (2), (+)-isocorydine (3), (+)-nuciferine (4), (+)-roemerine (5), (−)-tetrahydropseudocolumbamine (6), a mixture of 6, liriodenine (9) and lysicamine (10), a mixture of 1,2,9-trimethoxy-10-hydroxyaporphine (7) and bulbocapnine (8), 9, 10, and (+)-N-methyllindicarpine (11). Compounds 6, 7, 8, and 11 have not been previously reported in the family Annonaceae. Furthermore, the formerly synthetic 1,2,9-trimethoxyaporfin-10-ol (7) is described for the first time as a natural aporphine alkaloid herein. The chemical structures were established by 1D and 2D NMR as well as in comparison with data previously reported in the literature. The cytotoxic activity of the alkaloids was evaluated against tumor (B16-F10, HepG2, HL-60, and K562) and non-tumor (PBMC) cell lines. Alkaloid 1 presented significant activity against HepG2 cell lines with IC 50 of 9.60 µmol L-1 while the mixture of 6, 9 and 10 displayed strong cytotoxic activity against HL-60 and K562 cell lines with IC 50 values of 3.41 an 8.50 µmol L-1 , respectively.

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“…The flavonoids of C. axillaris were found to protect against myocardial ischemia and myocardial infarction in rats with myocardial ischemia-reperfusion injury ( Li and Cui, 2014 ; Li et al, 2014 ). Besides, these flavonoids also alleviate cardiac dysfunction and myocardial interstitial fibrosis ( Li and Cui, 2014 ; Li et al, 2014 ; Sun et al, 2014 ). The flavonoids of C. axillaris possess potent antioxidant properties ( Bao et al, 2001 ).…”

Section: Discussionmentioning

confidence: 99%

Tsantan Sumtang Restored Right Ventricular Function in Chronic Hypoxia-Induced Pulmonary Hypertension Rats

Yang

Sun

Su³

et al. 2021

Front. Pharmacol.

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Background: Tsantan Sumtang originated from Four Tantras, which consisted of Choerospondias axillaris (Roxb.) B. L. Burtt and A. W. Hill, Santalum album L., and Myristica fragrans Houtt. The three herbs are in ratio 1:1:1. This medication is widely used for cardiovascular diseases.Aims: The purpose of this study was to explore the effect of Tsantan Sumtang on right ventricular (RV) function in hypoxia-induced pulmonary hypertension (HPH) rats and investigate the underlying mechanism.Methods: Sixty male Sprague-Dawley (SD) rats were divided into control, hypoxia, and hypoxia + Tsantan Sumtang (1.0, 1.25, and 1.5 g•kg−1•d−1) groups. Chronic hypoxia was induced by putting the rats inside a hypobaric chamber for four weeks and adjusting the inner pressure and oxygen content to match an altitude of 4500 m. Echocardiography was used to assess RV function and right ventricular-pulmonary arterial (RV-PA) coupling. The physiological parameters of the animals were also evaluated. Morphological characteristics of RV were assessed by hematoxylin and eosin (H&E) staining and TEM. Masson’s trichrome staining, immunohistochemical staining, western blotting, and TUNEL assay were used to assess fibrosis and apoptosis levels. The antioxidant and anti-apoptosis properties of Tsantan Sumtang were also evaluated. The effect of Tsantan Sumtang on ROCK signaling pathway was evaluated using real-time quantitative PCR and western blotting.Results: We established an HPH rat model as indicated by the significant increases in the physiological parameters of the rats. Tsantan Sumtang showed a significant cardiac-protective function and an improved effect on RV-PA coupling. Moreover, Tsantan Sumtang treatment inhibited fibrosis and alleviated apoptosis and oxidative stress in RV. In terms of mechanism, Tsantan Sumtang reduced the expression of ROCK (ROCK1, ROCK2) in RV, inhibited cardiac remodeling-related transcription factors (NFATc3, P-STAT3), and regulated apoptosis-related proteins.Conclusion: Tsantan Sumtang was able to restore RV function, improve RV-PA coupling, recover hemodynamic and hematological indexes, and protect RV against structural maladaptive remodeling in the HPH rats. These findings demonstrated that Tsantan Sumtang protects the function of RV in HPH rats. The antioxidant and anti-apoptosis properties of Tsantan Sumtang may be responsible for inhibiting the ROCK signaling pathway.

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Cytotoxicity of Aporphine, Protoberberine, and Protopine Alkaloids from Dicranostigma leptopodum (Maxim.) Fedde

Cited by 16 publications

References 33 publications

Semisynthetic Studies on and Biological Evaluation of N-Methyllaurotetanine Analogues as Ligands for 5-HT Receptors

Semisynthetic Studies on and Biological Evaluation of N-Methyllaurotetanine Analogues as Ligands for 5-HT Receptors

ALKALOIDS FROM LEAVES OF Guatteria pogonopus (ANNONACEAE) AND THEIR CYTOTOXICITIES

Tsantan Sumtang Restored Right Ventricular Function in Chronic Hypoxia-Induced Pulmonary Hypertension Rats

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