Structure elucidation of indole–indoline type alkaloids: A retrospective account from the point of view of current NMR and MS technology

Béni, Zoltán; Háda, Viktor; Dubrovay, Zsófia; Szántay, Csaba

doi:10.1016/j.jpba.2012.02.015

Cited by 23 publications

(3 citation statements)

References 95 publications

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“…NMR spectroscopy has a long-standing tradition to be applied to the characterization of pure compounds as it has been the case for the structural elucidation of TIAs. The continuous development of more and more sophisticated one-dimensional (1D) and 2D pulse sequences in NMR, various structure elucidation strategies have been developed and in the early 2000s, the unambiguous NMR-based structure elucidation of bisindoles is now inconceivable without using a 'holistic' NMR approach, that is, a full 1 H and 13 C NMR assignment in conjunction with the establishment of all spin-spin connectivities by a broad range of 2D-NMR methods, that is, homonuclear correlated spectroscopy (COSY), total correlated spectroscopy (TOCSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC), heteronuclear multiple quantum coherence (HMQC), nuclear Overhauser effect spectroscopy (NOESY) or ROESY experiments (Beni, Hada, Dubrovay, & Szantay, 2012). There are excellent reviews covering the structural elucidation of the alkaloids in Catharanthus (Beni et al, 2012;Blaskó & Cordell, 1990;Dubrovay, Háda, Béni, & Szántay, 2012;Háda et al, 2012), Aspidosperma (Guimaraes, Braz-Filho, & Vieira, 2012), Tabernaemontana (Danieli & Palmisano, 1987;Nielsen, Hazell, Hazell, Ghia, & Torssell, 1994;Talapatra, Patra, & Talapatra, 1975), and Strychnos (Penelle et al, 2001(Penelle et al, , 2000Rasoanaivo, Martin, Guittet, & Frappier, 2002) already published.…”

Section: Nmr and Lc-ms-based Metabolic Fingerprinting On Tiasmentioning

confidence: 99%

New Methods of Analysis and Investigation of Terpenoid Indole Alkaloids

Goldhaber-Pasillas

Choi

Verpoorte

2013

New Light on Alkaloid Biosynthesis and Future Prospects

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Introduction 235 2. Extraction and Purification Methods 236 2.1 Solvent extraction 237 2.2 Ionic liquids 239 2.3 Molecular imprinted polymers 239 2.4 Supercritical CO 2 240 3. Analytical Methods 242 3.1 HPLC and hyphenated techniques 242 3.2 Ultra high-pressure LC-MS 243 3.3 Gas chromatography coupled to mass spectroscopy 248 3.4 High-speed counter-current chromatography 251 3.5 Capillary electrophoresis 253 3.6 Quantitative nuclear magnetic resonance 259 4. Applications in Fingerprint Analysis 260 4.1 NMR and LC-MS-based metabolic fingerprinting on TIAs 260 5. Conclusions 262 References 263

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Section: Nmr and Lc-ms-based Metabolic Fingerprinting On Tiasmentioning

confidence: 99%

New Methods of Analysis and Investigation of Terpenoid Indole Alkaloids

Goldhaber-Pasillas

Choi

Verpoorte

2013

New Light on Alkaloid Biosynthesis and Future Prospects

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“…Previous intensive studies of antitumor indole alkaloids have resulted in considerable groundbreaking discoveries in the past decades [ 4 , 5 ]. Especially due to star natural antitumor indoles entering the clinical forefront, such as vinblastine, vincristine, and vindesine, MIAs with remarkable biological activities and fascinating structures have attracted more and more attention from the pharmaceutical industry [ 6 , 7 ]. However, it is difficult to obtain clear NMR signals or fine single crystals from a large number of compounds, which limits the rapid determination of the stereoconfiguration of MIAs with multiple chiral centers.…”

Section: Introductionmentioning

confidence: 99%

Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from Gelsemium elegans

Song

Liang

et al. 2023

Molecules

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Two new monoterpenoid indole alkaloids, gelselegandines F (1) and G (2), were isolated from the aerial parts of Gelsemium elegans. Their structures were elucidated by means of spectroscopic techniques and quantum chemical calculations. The ECD calculations were conducted at the B3LYP/6-311G(d,p) level and NMR calculations were carried out using the Gauge-Including Atomic Orbitals (GIAO) method. Structurally, the two new compounds possessed rare, cage-like, monoterpenoid indole skeletons. All isolated compounds and the total alkaloids extract were tested for cytotoxicity against four different tumor cell lines. The total alkaloids extract of G. elegans exhibited significant antitumor activity with IC50 values ranging from 32.63 to 82.24 ug/mL. In order to discover anticancer leads from the active extraction, both new indole compounds (1–2) were then screened for cytotoxicity. Interestingly, compound 2 showed moderate cytotoxicity against K562 leukemia cells with an IC50 value of 57.02uM.

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“…Vinca alkaloids, which structurally belong to the bisindole group, are well known for their antitumor bioactivities. Natural products from this group, such as vinblastine [6], vincristine [7], vindesine [8] and their structurally modified compounds, are currently commercial drugs and are used in the clinic to treat cancers in many countries [9]. Searching for optimized or simplified indole alkaloids has been the spotlight of antitumor drug discovery for several years.…”

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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Structure elucidation of indole–indoline type alkaloids: A retrospective account from the point of view of current NMR and MS technology

Cited by 23 publications

References 95 publications

New Methods of Analysis and Investigation of Terpenoid Indole Alkaloids

New Methods of Analysis and Investigation of Terpenoid Indole Alkaloids

Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from Gelsemium elegans

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

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