Ancistrotanzanine A, the First 5,3‘-Coupled Naphthylisoquinoline Alkaloid, and Two Further, 5,8‘-Linked Related Compounds from the Newly Described Species<i>Ancistrocladus tanzaniensis</i><sup>,1</sup>

Bringmann, Gerhard; Dreyer, Michael; Faber, Johan H.; Dalsgaard, Petur Weihe; Stærk, Dan; Jaroszewski, Jerzy W.; Ndangalasi, Henry J.; Mbago, Frank M.; Brun, Reto; Reichert, Matthias; Maksimenka, Katja; Christensen, Søren Brøgger

doi:10.1021/np030077b

Cited by 65 publications

(69 citation statements)

References 28 publications

(68 reference statements)

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“…Nonetheless, there are a few examples, such as those of knipholone anthrone (5) or xylogranatin F (6), for which TDDFT calculations are not sufficient to reproduce the ex- Figure 9. Further selected examples of structurally diverse compounds with different types of stereogenic elements, the absolute configurations of which were established by quantum chemical CD calculations (saludimerin A, [83] ancistrotanzanin A, [84] bi [10]paracyclophanes, [56] joziknipholone A, [85] γ-rubromycin, [86] a Tröger's base derivative, [87] resistoflavin, [88] shearinine D, [89] nigerone; [90] for other examples see ref. [91] ).…”

Section: Conclusion: Semiempirical Methods Dft or Mrci?mentioning

confidence: 99%

The Assignment of Absolute Stereostructures through Quantum Chemical Circular Dichroism Calculations

et al. 2009

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The determination of the absolute configuration of a chiral compound of synthetic or natural origin is a problem that every organic chemist willl certainly have to face some day. An efficient and reliable method for the assignment of absolute stereostructures, independent of empirical CD rules, is the combination of experimental circular dichroism (CD) investigations with quantum chemical CD calculations. The availability of a broad variety of quantum chemical methods and the continuing appearance of new approaches permits -but also requires -the most appropriate method to be selected in each particular case, with respect to accuracy, time con-

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Section: Conclusion: Semiempirical Methods Dft or Mrci?mentioning

confidence: 99%

The Assignment of Absolute Stereostructures through Quantum Chemical Circular Dichroism Calculations

et al. 2009

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“…This class of naturally occurring biaryls was initially described as exhibiting strong growth-inhibiting activities in vitro against Plasmodium falciparum and Plasmodium berghei (20,21,23) and in vivo against P. berghei (22). Efficacy against Trypanosoma brucei (11) and Leishmania donovani has also been reported (8)(9)(10). These findings suggest that naphthylisoquinoline alkaloids constitute an interesting class of antiparasitic compounds that should be pharmacologically explored.…”

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confidence: 87%

Activities of Naphthylisoquinoline Alkaloids and Synthetic Analogs againstLeishmania major

Ponte-Sucre

Faber²,

Gulder³

et al. 2007

Antimicrob Agents Chemother

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The current treatments for leishmaniasis are unsatisfactory due to their toxic side effects, high costs, and increasing problems with drug resistance. Thus, there is an urgent need for alternative drugs against leishmaniasis. Different approaches have been used to identify novel pharmacophores against Leishmania sp. parasites, and one strategy has been the analysis of naturally occurring plant-derived compounds, including naphthylisoquinoline alkaloids. In the present study, we examined the abilities of these alkaloids to inhibit the growth of Leishmania major promastigotes and evaluated their effects on macrophages, dendritic cells, and fibroblasts. Furthermore, we determined the efficacy of selected compounds in decreasing the infection rate of macrophages and regulating their production of cytokines and nitric oxide. Our results demonstrate that the naphthylisoquinoline alkaloids ancistrocladiniums A and B (compounds 10 and 11) and the synthetic isoquinolinium salt (compound 14) were effective against intracellular amastigotes in the low submicromolar range, while toxicity against mammalian cells was observed at concentrations that were significantly higher than those needed to impair parasite replication. The activities of compounds 11 and 14 were mainly directed against the amastigote stage of L. major. This effect was not associated with the stimulation of host macrophages to produce nitric oxide or secrete cytokines relevant for the leishmanicidal function. In conclusion, our data suggest that ancistrocladiniums A and B (compounds 10 and 11) and the synthetically prepared isoquinolinium salt (compound 14) are promising candidates to be considered as lead compounds for leishmanicidal drugs.

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“…(Ancistrocladaceae) are known to be rich sources of naphthylisoquinoline alkaloids (Figure 2). [85][86][87][88][89][90][91] Ancistrocladidine …”

Section: Naphthylisoquinolinesmentioning

confidence: 99%

Compounds from African Medicinal Plants with Activities against Protozoal Diseases: Schistosomiasis, Trypanosomiasis and Leishmaniasis

Cv¹,

Ntie‐Kang²,

Sh.³

et al. 2018

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An absolute configuration of 5R seems to decrease activity of the compound IntroductionProtozoa may be considered as microscopic, essentially single-celled, eukaryotic organisms that are free-living or parasitic (obtaining their food by eating other organisms or their products) in nature. Parasitic protozoal diseases continue to be a cause of considerable morbidity and mortality globally. 1,2Parasitic protozoal diseases include malaria, 3,4 trypanosomiasis (African sleeping sickness and Chagas disease), 5-7 leishmaniasis 8 and schistosomiasis. 9,10 They threaten almost one-third of the world's population, the most numerous incidents being recorded in over 100 Tropical and developing countries and territories, Figure 1. 11,12 Malaria, for example, was reported by the WHO, to be responsible for approximately 214 million sickness cases and 438,000 deaths globally in 2017. 13 The African region recorded the most death-related cases, especially amongst infants below the age of 5 and pregnant women. Schistosomiasis, caused by parasites of the Schistosoma genus are responsible for about 200 million sickness cases and about 280,000 death-related incidents annually worldwide.9,10,14 Only one drug (praziquantel) has been proven to be effective in the treatment of human schistosomiasis, with no vaccine available or in development so far.15-21 Serious concerns about drug selectivity and resistance were raised in 2013 when over 30 million people were treated in Sub-Saharan Africa. 20 Moreover, observed resistance and reduced efficiency of praziquantel in laboratory strains have prompted the search for alternative therapeutic strategies. Trypanosomiasis, which represents several diseases caused by parasites of the genus Trypanosoma, is also of interest. 5,27,29 This disease, which is much arguably the most important disease of man and domesticated animals, accounts for over 8 million reported annual cases globally, especially in the tropical regions of Latin America and Africa. 30,31 Although the present number of cases seems negligible on a worldwide scale, great socioeconomic effects on the endemic areas by this disease are forecast if inadequate attention (both at the communal, national, and international levels) is not given. 7,29,[32][33][34] Leishmaniasis is caused by parasites of the Leishmania type, which is also transmitted by certain types of sandflies. 35,36 The diseases are reported by the WHO to be responsible for about 1 million new cases leading to approximately 30,000 deaths annually on a global scale. The major cause is linked to environmental changes A R T I C L E I N F O A B S T R A C TArticle history:English abstract: Parasitic diseases continue represent a threat on a global scale, particularly among the poorest countries in the world. This is particularly because of the absence of vaccines, and in some cases, resistance against available drugs, currently being used for their treatment. In this review emphasis is laid on natural products and scaffolds from African medicinal plants (AMPs) for lead drug di...

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Ancistrotanzanine A, the First 5,3‘-Coupled Naphthylisoquinoline Alkaloid, and Two Further, 5,8‘-Linked Related Compounds from the Newly Described SpeciesAncistrocladus tanzaniensis^,1

Cited by 65 publications

References 28 publications

The Assignment of Absolute Stereostructures through Quantum Chemical Circular Dichroism Calculations

The Assignment of Absolute Stereostructures through Quantum Chemical Circular Dichroism Calculations

Activities of Naphthylisoquinoline Alkaloids and Synthetic Analogs againstLeishmania major

Compounds from African Medicinal Plants with Activities against Protozoal Diseases: Schistosomiasis, Trypanosomiasis and Leishmaniasis

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Ancistrotanzanine A, the First 5,3‘-Coupled Naphthylisoquinoline Alkaloid, and Two Further, 5,8‘-Linked Related Compounds from the Newly Described SpeciesAncistrocladus tanzaniensis,1

Cited by 65 publications

References 28 publications

The Assignment of Absolute Stereostructures through Quantum Chemical Circular Dichroism Calculations

The Assignment of Absolute Stereostructures through Quantum Chemical Circular Dichroism Calculations

Activities of Naphthylisoquinoline Alkaloids and Synthetic Analogs againstLeishmania major

Compounds from African Medicinal Plants with Activities against Protozoal Diseases: Schistosomiasis, Trypanosomiasis and Leishmaniasis

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Product

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Ancistrotanzanine A, the First 5,3‘-Coupled Naphthylisoquinoline Alkaloid, and Two Further, 5,8‘-Linked Related Compounds from the Newly Described SpeciesAncistrocladus tanzaniensis^,1