Biscarpamontamines A and B, an Aspidosperma−Iboga Bisindole Alkaloid and an Aspidosperma−Aspidosperma Bisindole Alkaloid, from <i>Tabernaemontana sphaerocarpa</i>

Zaima, Kazumasa; Hirata, Toshihiko; Hosoya, Tsuyoshi; Hirasawa, Yusuke; Koyama, Koichiro; Rahman, Aulia; Kusumawati, Idha; Zaini, Noor Cholies; Shiro, Motoo; Morita, Hiroshi

doi:10.1021/np900365r

Cited by 37 publications

(11 citation statements)

References 10 publications

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“…This signal is important to determine whether the isolated compound is vobtusine or vobtusine lactone. Overall, the correlations in HSQC and HMBC spectra showed a suitable correlation with the structure of vobtusine lactone, and have high similarity with previously reported NMR spectra of vobtusine lactone isolated from Tabernaemontana sphaerocarpa Blume is a member of the Apocynaceae family (Zaima et al, 2009).…”

Section: Characteristic Of An Isolated Compoundsupporting

confidence: 83%

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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Section: Characteristic Of An Isolated Compoundsupporting

confidence: 83%

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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“…Bis-indole alkaloid 111 showed potent cytotoxicity against various human cancer cell lines, including human blood premyelocytic Leukemia (HL60), multiple myeloma (RPMI8226), non-small cell lung carcinoma (NCI-H226), human colon cancer (HCT116), and human breast adenocarcinoma (MCF-7) cells with IC 50 value in the range of 0.5-1.9 µM [48].…”

Section: Tabernaemontana Sphaerocarpa Blumementioning

confidence: 99%

A Review on Tabernaemontana spp.: Multipotential Medicinal Plant

Athipornchai

2018

Asian J Pharm Clin Res

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Plants in the genus Tabernaemontana have been using in Thai and Chinese traditional medicine for the treatment several diseases. The great majority constituents of Tabernaemontana species have already been subjected to isolation and identification of monoterpene indole alkaloids present in their several parts. Many of monoterpene indole alkaloids exhibited a wide array of several activities. The biogenesis, classification, and biological activities of these alkaloids which found in Tabernaemontana plants were discussed in this review and its brings the research up-to-date on the bioactive compounds produced by Tabernaemontana species, directly or indirectly related to human health.

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“…The cytotxic activity show that vobtusine have a moderate cytotoxic activity with IC 50 15.8 μM. The effect of vobtusine on the cell cycle was determined by the distribution of vobtusine-treated cells in the G 1 , S, and G 2 / M phases detected by flow cytometry [21], [22]. The results of cell cycle analysis indicate the ratio of the number of cells in each cell cycle did not have significant differences depend on vobtusine concentration although cell number in G 1 phase have tendency to decrease according to the increasing of vobtusine (Fig.…”

Section: Resultsmentioning

confidence: 99%

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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Biscarpamontamines A and B, an Aspidosperma−Iboga Bisindole Alkaloid and an Aspidosperma−Aspidosperma Bisindole Alkaloid, from Tabernaemontana sphaerocarpa

Cited by 37 publications

References 10 publications

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

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

A Review on Tabernaemontana spp.: Multipotential Medicinal Plant

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

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