Cytotoxic Indole Alkaloids from <i>Tabernaemontana divaricata</i>

Bao, Ming; Yan, Juming; Cheng, Guiguang; Li, Xing-Yao; Liu, Yaping; Li, Yan; Cai, Xiang‐Hai; Luo, Xiao‐Dong

doi:10.1021/np400130y

Cited by 72 publications

(32 citation statements)

References 23 publications

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“…In 2013, Zhang et al reported to study of conophylline (83), is a bis-indole alkaloid (Scheme Athipornchai 6) consisting of two pentacyclic aspidosperma skeletons, isolated from T. divaricata, which has been found to induce b-cell differentiation in rat pancreatic acinar carcinoma cells and in cultured rat pancreatic tissue [35]. In the same year, Bao et al reported the isolation of five new cytotoxic vobasinyl-ibogan-type bisindole alkaloids (Scheme 6), tabernaricatines A-E (84-88), two new monomers, tabernaricatines F and G (89 and 90), and 24 known indole alkaloids were isolated from the aerial parts of T. divaricata [36]. In 2012, two research groups including Jain et al and Mukhram et al reported to evaluate the antifertility effect of leaves and flowers extracts of T. divaricata in male rats and female albino mice.…”

Section: Tabernaemontana Dichotomamentioning

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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Section: Tabernaemontana Dichotomamentioning

confidence: 99%

A Review on Tabernaemontana spp.: Multipotential Medicinal Plant

Athipornchai

2018

Asian J Pharm Clin Res

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“…Tabernaemontana divaricate, belonging to the Apocynaceae family, was investigated for its cytotoxic potential against NIH3T3 and HeLa cell lines and the respective IC 50 values were >100 µg/mL and 35.3 µg/mL, respectively. Several alkaloidal cytotoxic compounds i.e., ervachinine, cononitarine, conofoline, conophylline and cisplatin were also reported, among which conophylline ( Figure 2) was found to be most potent against HL-60 (human Caucasian promyelocytic leukemia), SMMC-7721, A-549, MCF-7, and SW480 cell lines (IC 50 values of 0.17, 0.35, 0.21, 1.02, and 1.49 µM, respectively) [29,30].…”

Section: Apocynaceaementioning

confidence: 99%

A Review of Cytotoxic Plants of the Indian Subcontinent and a Broad-Spectrum Analysis of Their Bioactive Compounds

Mazumder

Biswas²,

Raja³

et al. 2020

Molecules

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Cancer or uncontrolled cell proliferation is a major health issue worldwide and is the second leading cause of deaths globally. The high mortality rate and toxicity associated with cancer chemotherapy or radiation therapy have encouraged the investigation of complementary and alternative treatment methods, such as plant-based drugs. Moreover, over 60% of the anti-cancer drugs are molecules derived from plants or their synthetic derivatives. Therefore, in the present review, an attempt has been made to summarize the cytotoxic plants available in the Indian subcontinent along with a description of their bio-active components. The review covers 99 plants of 57 families as well as over 110 isolated bioactive cytotoxic compounds, amongst which at least 20 are new compounds. Among the reported phytoconstituents, artemisinin, lupeol, curcumin, and quercetin are under clinical trials, while brazilin, catechin, ursolic acid, β-sitosterol, and myricetin are under pharmacokinetic development. However, for the remaining compounds, there is little or no information available. Therefore, further investigations are warranted on these subcontinent medicinal plants as an important source of novel cytotoxic agents.

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“…Searching for optimized or simplified indole alkaloids has been the spotlight of antitumor drug discovery for several years. In our continual search for natural antitumor products from medicinal plants, indole alkaloids were found to be the most potent candidates in a cytotoxicity bioassay against five human cancer cell lines [10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29]. Among these cytotoxic indoles, 3 α -acetonyltabersonine, an aspidosperma-type monoterpenoid indole alkaloid, structurally similar to vindoline, showed the best bioactivity, with IC 50 values of 0.2–0.6 μM against human myeloid leukemia HL-60 cells, hepatocellular carcinoma SMMC-7721 cells, lung cancer A549 cells, breast cancer MCF-7 cells, and colon cancer SW480 cells.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Indole Alkaloid 3α-Acetonyltabersonine Induces Glioblastoma Apoptosis via Inhibition of DNA Damage Repair

Zhao

Xiao-fang

et al. 2017

Toxins

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Cytotoxic indole alkaloids from Melodinus suaveolens, which belongs to the toxic plant family Apocynaceae, demonstrated impressive antitumor activities in many tumor types, but less application in glioblastoma, which is the lethal brain tumor. In the present study, we reported the anti-glioblastoma activity of an indole alkaloid, 3α-acetonyltabersonine, which was isolated from Melodinus suaveolens. 3α-acetonyltabersonine was cytotoxic to glioblastoma cell lines (U87 and T98G) and stem cells at low concentrations. We verified 3α-acetonyltabersonine could suppress tumor cell proliferation and cause apoptosis in glioblastoma stem cells (GSCs). Moreover, detailed investigation of transcriptome study and Western blotting analysis indicated the mitogen activated protein kinase (MAPK) pathway was activated by phosphorylation upon 3α-acetonyltabersonine treatment. Additionally, we found 3α-acetonyltabersonine inhibited DNA damage repair procedures, the accumulated DNA damage stimulated activation of MAPK pathway and, finally, induced apoptosis. Further evidence was consistently obtained from vivo experiments on glioblastoma mouse model: treatment of 3α-acetonyltabersonine could exert pro-apoptotic function and prolong the life span of tumor-bearing mice. These results in vitro and in vivo suggested that 3α-acetonyltabersonine could be a potential candidate antitumor agent.

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Cytotoxic Indole Alkaloids from Tabernaemontana divaricata

Cited by 72 publications

References 23 publications

A Review on Tabernaemontana spp.: Multipotential Medicinal Plant

A Review on Tabernaemontana spp.: Multipotential Medicinal Plant

A Review of Cytotoxic Plants of the Indian Subcontinent and a Broad-Spectrum Analysis of Their Bioactive Compounds

Cytotoxic Indole Alkaloid 3α-Acetonyltabersonine Induces Glioblastoma Apoptosis via Inhibition of DNA Damage Repair

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