New vasorelaxant indole alkaloids, taberniacins A and B, from Tabernaemontana divaricata

Hirasawa, Yusuke; Dai, X.; Deguchi, Jun; Hatano, Shota; Sasaki, Tadahiro; Ohtsuka, Ruri; Nugroho, Alfarius Eko; Kaneda, Toshio; Morita, Hiroshi

doi:10.1007/s11418-019-01293-9

Cited by 22 publications

(11 citation statements)

References 26 publications

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“…Both alkaloids exhibited moderate levels of vasorelaxant activity in an isolated rat aorta. The IC50 values of taberniacins A and B were 2.86 µM and 580 nM, respectively, and vasorelaxation activity increased in a concentration-dependent manner [38].…”

Section: Hypotensive Activitymentioning

confidence: 96%

Plant-Based Indole Alkaloids: A Comprehensive Overview from a Pharmacological Perspective

et al. 2021

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Plant-based indole alkaloids are very rich in pharmacological activities, and the indole nucleus is considered to contribute greatly to these activities. This review’s fundamental objective is to summarize the pharmacological potential of indole alkaloids that have been derived from plants and provide a detailed evaluation of their established pharmacological activities, which may contribute to identifying new lead compounds. The study was performed by searching various scientific databases, including Springer, Elsevier, ACS Publications, Taylor and Francis, Thieme, Wiley Online Library, ProQuest, MDPI, and online scientific books. A total of 100 indole compounds were identified and reviewed. The most active compounds possessed a variety of pharmacological activities, including anticancer, antibacterial, antiviral, antimalarial, antifungal, anti-inflammatory, antidepressant, analgesic, hypotensive, anticholinesterase, antiplatelet, antidiarrheal, spasmolytic, antileishmanial, lipid-lowering, antimycobacterial, and antidiabetic activities. Although some compounds have potent activity, some only have mild-to-moderate activity. The pharmacokinetic profiles of some of the identified compounds, such as brucine, mitragynine, 7-hydroxymitragynine, vindoline, and harmane, were also reviewed. Most of these compounds showed promising pharmacological activity. An in-depth pharmacological evaluation of these compounds should be performed to determine whether any of these indoles may serve as new leads.

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Section: Hypotensive Activitymentioning

confidence: 96%

Plant-Based Indole Alkaloids: A Comprehensive Overview from a Pharmacological Perspective

et al. 2021

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“…This study is a continuation of our research on other Sumatran plants Hirasawa et al, 2019;Amelia et al, 2019;Susanty et al, 2014). In this work, we reported the structural characterization of vobtusine lactone and the cytotoxic activity of two isolated alkaloids from V. foetida against the A549 cell line.…”

Section: Introductionmentioning

confidence: 72%

Cytotoxic Activity, and Molecular Docking of Indole Alkaloid Voacangine and Bisindole Alkaloid Vobtusine, Vobtusine Lactone from the Indonesian Plant: Voacanga foetida (Blume) Rolfe

Susanty

2021

Indonesian J Pharm

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ABSTRACT The purpose of this study was to isolate and test its cytotoxic activity starting from extract fraction and its isolate compound, then carried out molecular docking to confirm the potential biological activity of ligands (vocangine, vobtusine, and vobtusine lactone) against inhibition proteins (Bcl-2, Bcl-xL, and Mcl-1), activation protein Bax and activation of apoptotic execution protein Caspase-3. This research is an experimental quantitative study using column chromatography and HPLC methods in the isolation process, MTT assay in determining the cytotoxic activity, and molecular docking in determining the prediction of apoptotic mechanism. The cytotoxic activity of VFB-DA, VFB-DB, VFB-BuOH, VFB-DB4 fractions, voacangine compounds, vobtusine are very strong. while vobtusine lactone is moderate cytotoxic activity. The docking score for voacangine, vobtusine, and vobtusine lactone compounds against Bcl-2 is -9.93; -10.07; -9.03 kcal/mol, against Bcl-xl is -9.77; -11.69; -9.76 kcal/mol, against Mcl-1 is -10.70; -10.77; -9.53 kcal/mol, and for Bax is -8.99; -6.87; -6.99 kcal/mol, as well as against caspase3 is -12.05; -12.21; -12.02 kcal/mol. The cytotoxic activity of voacangine, vobtusine, and vobtusine lactone compounds is thought to cause cell death by suppressing Bcl-2 activity; Bcl-xl; and Mcl-1, increased Bax activity and increased caspase3 activity. Key words: Voacanga foetida, in vitro, in silico

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“…The plant contained high concentrations of alkaloids [4]. In continuation of our study on Sumatran plants [5][6][7][8][9][10][11][12]. Our further study was carried out on the barks of V. foetida since it has cytotoxicity activity [13].…”

Section: Introductionmentioning

confidence: 89%

Vobtusine from Voacanga foetida (Blume) Rolfe Induces Apoptosis via Activation of Caspase Pathway in Human HL-60 Leukemia Cell Line

Susanty¹,

Hamidi²,

Yanwirasti³

et al. 2020

Int. J. Adv. Sci. Eng. Inf. Technol.

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Vobtusine is an aspidosperma-aspidosperma alkaloid isolated from alkaloid DCM base fraction of the bark of Voacanga foetida (Blume) Rolfe (Apocynaceae). In this study, the effect of vobtusine on the cell cycle, apoptosis induction, and Bcl-2 family protein expression were investigated by flow cytometr, DNA fragmentation analysis, and western blotting, respectively. The results of cell cycle analysis indicated the ratio of the number of cells in each phase did not have significant differences depend on vobtusine concentration although cell number in G1 phase had tendency to decrease according to the increasing of vobtusine concentration. Besides, the sub-G1 phase population of HL-60 cells treated with vobtusine was increased compared with that of cells without treatments (5.9%-23.8%). DNA fragmentation was observed from 20 µM, and the degree of fragmentation was dependent on vobtusine concentration. Caspase-3 activity increased 4.6 times compared to control. After being treated with caspase-9 inhibitor, vobtusine-induced elevation of caspase-3 activity decreased. This shows that caspase-3 activity depends on caspase-9. Vobtusine was also induced apoptotic cell death involved a mitochondrial by Bid activation and Bcl-xL downregulation. Therefore, vobtsusine-induced apoptosis process was initiated by caspase-9 via change of Bcl-2 family protein expression and executed by caspase-3, followed by cell death due to their proteolytic activity. These results indicated the mechanism action of vobtusine as anti-cancer compound via intrinsic pathway.

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New vasorelaxant indole alkaloids, taberniacins A and B, from Tabernaemontana divaricata

Cited by 22 publications

References 26 publications

Plant-Based Indole Alkaloids: A Comprehensive Overview from a Pharmacological Perspective

Plant-Based Indole Alkaloids: A Comprehensive Overview from a Pharmacological Perspective

Cytotoxic Activity, and Molecular Docking of Indole Alkaloid Voacangine and Bisindole Alkaloid Vobtusine, Vobtusine Lactone from the Indonesian Plant: Voacanga foetida (Blume) Rolfe

Vobtusine from Voacanga foetida (Blume) Rolfe Induces Apoptosis via Activation of Caspase Pathway in Human HL-60 Leukemia Cell Line

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