Strychnobaillonine, an Unsymmetrical Bisindole Alkaloid with an Unprecedented Skeleton from<i>Strychnos icaja</i>Roots

Tchinda, Alembert T.; Jansen, Olivia; Nyemb, Jean Noël; Tits, Monique; Dive, Georges; Angenot, Luc; Frédérich, Michel

doi:10.1021/np400908u

Cited by 23 publications

(18 citation statements)

References 17 publications

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“…Chemical investigation of Alstonia macrophylla bark led to the isolation of two new nitrogenous derivatives, alstoniaphyllines A (13) and B (14), a new indole alkaloid, alstoniaphylline C (15), and eight known alkaloids including alstonisine (16) [29]. Also, Tchinda et al [30] reported the isolation of a new bisindole alkaloid, strychnobaillonine (19), with original C-17-N-1′ and C-23-C-17′ junctions, in…”

Section: Indole Alkaloidsmentioning

confidence: 99%

“…Fadaeinasab et al [33] isolated seven isoquinoline alkaloids from the bark of Actinodaphne macrophylla. ey display in vitro antiplasmodial activity against P. falciparum 3D7 with IC 50 values ranging from 0.05 to 3.11 μM for cycleanine (25), 10-demethylxylopinine (26), reticuline (27), laurotetanine (28), bicuculine (29), α-hydrastine (30), and anolobine (31), respectively. Compound 26 was found to be the most active.…”

Section: Phenanthroindolizine Alkaloidsmentioning

confidence: 99%

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Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies

Uzor

2020

Evidence-Based Complementary and Alternative Medicine

105

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Malaria is one of the major health problems in developing countries. The disease kills a large number of people every year and also affects financial status of many countries. Resistance of the plasmodium parasite, the causative agent, to the existing drugs, including chloroquine, mefloquine, and artemisinin based combination therapy (ACT), is a serious global issue in malaria treatment and control. This warrants an urgent quest for novel compounds, particularly from natural sources such as medicinal plants. Alkaloids have over the years been recognized as important phytoconstituents with interesting biological properties. In fact, the first successful antimalarial drug was quinine, an alkaloid, which was extracted from Cinchona tree. In the present review work, the alkaloids isolated and reported recently (2013 till 2019) to possess antimalarial activity are presented. Several classes of alkaloids, including terpenoidal, indole, bisindole, quinolone, and isoquinoline alkaloids, were identified with a promising antimalarial activity. It is hoped that the reports of the review work will spur further research into the structural modification and/or development of the interesting compounds as novel antimalarial drugs.

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Section: Indole Alkaloidsmentioning

confidence: 99%

Section: Phenanthroindolizine Alkaloidsmentioning

confidence: 99%

Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies

Uzor

2020

Evidence-Based Complementary and Alternative Medicine

105

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“…14). The alkaloids were active against the 3D7 strain of P. falciparum , and the trisindole 94 was also cytotoxic against WI-38 cells (SI < 10), whereas 93 was not cytotoxic at the highest tested concentration (10 µg/mL) [77]. Interestingly, while monomers of Strychnos alkaloids do not have antiplasmodial activity, polymerization increases the basic nature of the monomers and confers antiplasmodial potency.…”

Section: Alkaloidsmentioning

confidence: 99%

Antiplasmodial natural products: an update

Tajuddeen

Heerden

2019

Malar J

127

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BackgroundMalaria remains a significant public health challenge in regions of the world where it is endemic. An unprecedented decline in malaria incidences was recorded during the last decade due to the availability of effective control interventions, such as the deployment of artemisinin-based combination therapy and insecticide-treated nets. However, according to the World Health Organization, malaria is staging a comeback, in part due to the development of drug resistance. Therefore, there is an urgent need to discover new anti-malarial drugs. This article reviews the literature on natural products with antiplasmodial activity that was reported between 2010 and 2017.MethodsRelevant literature was sourced by searching the major scientific databases, including Web of Science, ScienceDirect, Scopus, SciFinder, Pubmed, and Google Scholar, using appropriate keyword combinations.Results and DiscussionA total of 1524 compounds from 397 relevant references, assayed against at least one strain of Plasmodium, were reported in the period under review. Out of these, 39% were described as new natural products, and 29% of the compounds had IC50 ≤ 3.0 µM against at least one strain of Plasmodium. Several of these compounds have the potential to be developed into viable anti-malarial drugs. Also, some of these compounds could play a role in malaria eradication by targeting gametocytes. However, the research into natural products with potential for blocking the transmission of malaria is still in its infancy stage and needs to be vigorously pursued.

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“…Recently Tchinda, et al [ 1 ] reported the isolation of strychnobaillonine ( 1 ), an unsymmetrical bisindole alkaloid with an unusual skeleton from Strychnos icaja roots. The structure of this intriguing natural compound was established by means of a detailed spectroscopic analysis, using 1 H and 13 C NMR techniques, including DEPT, HSQC, COSY, NOESY, HMBC, and HRESIMS.…”

Section: Introductionmentioning

confidence: 99%

Computational ¹H and ¹³C NMR of strychnobaillonine: On the way to larger molecules calculated at lower computational costs

Semenov

Krivdin

2020

Magnetic Reson in Chemistry

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The 1H and 13C NMR chemical shifts of strychnobaillonine, a very large dimeric indole alkaloid, consisting of as many as 46 nonhydrogen atoms, were calculated with using the established earlier the most effective computational protocol, PBE0/pcSseg‐2//pcseg‐2. A very good result was achieved at this level, characterized by the root mean square deviation of only 0.14 ppm for protons and 2.4 ppm for carbons, which enabled the verification of the configurations of its all 13 asymmetrical centers. Essential deviations of the calculated and experimental 1H NMR spectrum of strychnobaillonine were established in several cases, which enabled the performance of some additional NMR assignments and reassignments of the originally proposed structure.

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Strychnobaillonine, an Unsymmetrical Bisindole Alkaloid with an Unprecedented Skeleton fromStrychnos icajaRoots

Cited by 23 publications

References 17 publications

Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies

Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies

Antiplasmodial natural products: an update

Computational ¹H and ¹³C NMR of strychnobaillonine: On the way to larger molecules calculated at lower computational costs

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Strychnobaillonine, an Unsymmetrical Bisindole Alkaloid with an Unprecedented Skeleton fromStrychnos icajaRoots

Cited by 23 publications

References 17 publications

Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies

Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies

Antiplasmodial natural products: an update

Computational 1H and 13C NMR of strychnobaillonine: On the way to larger molecules calculated at lower computational costs

Contact Info

Product

Resources

About

Computational ¹H and ¹³C NMR of strychnobaillonine: On the way to larger molecules calculated at lower computational costs