Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds

Eaton, Alexander L.; Dalal, Seema; Cassera, María B.; Zhao, Sheng‐Yin; Kingston, David G. I.

doi:10.1021/acs.jnatprod.6b00347

Cited by 15 publications

(15 citation statements)

References 19 publications

(34 reference statements)

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“…Also, 372 , with two prenyl chains, was more active than the monoprenylated 371 , suggesting that prenylation is essential for the antiplasmodial activity of these compounds [232]. The synthesis of mallotojaponin C ( 372 ) was demonstrated in a three-step procedure [233]. Seven new polycyclic polyprenylated acylphloroglucinols (PPAPs), symphonones A ( 373 ), C–E ( 374 – 376 ), G ( 377 ), H ( 378 ), and 14-deoxy-7-epi-isogarcinol ( 379 ) have been isolated from Symphonia globulifera (Clusiaceae) root bark extract.…”

Section: Polyphenolsmentioning

confidence: 99%

Antiplasmodial natural products: an update

Tajuddeen

Heerden

2019

Malar J

113

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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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Section: Polyphenolsmentioning

confidence: 99%

Antiplasmodial natural products: an update

Tajuddeen

Heerden

2019

Malar J

113

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“…Recently, 131 and related compounds have been synthesized and evaluation of the antiplasmodial activity of the synthetic compounds confirmed the observed antimalarial activity properties of phloroglucinols. 61,62)…”

Section: Resultsmentioning

confidence: 99%

Novel Bioactive Natural Products Isolated from Madagascar Plants and Marine Organisms (2009–2017)

Dai

Liu

Rakotondraibe

2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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Madagascar's rain forests and tropical dry forests are home to numerous endemic plant species and the island is considered a biodiversity hotspot. About 80% of the Madagascan (Malagasy) population relies on traditional medicines that have been proven to contain a variety of biologically active compounds. In the search for bioactive compounds from Madagascan biodiversity, we accessed and collected most of the literature dealing with the isolation, structure elucidation, and biological activities of organic small molecules originating from Madagascan plants and marine organisms. Since we published the first review of this work in 2009 (Curr. Med. Chem., 17, 2010, Hou and Harinantenaina), the present paper covers the isolation, structures, and bioactivity of 182 new secondary metabolites isolated from Malagasy higher plants and marine organisms in the last seven years (2009-2017).

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“…has also demonstrated the in vitro leishmanicidal activity of prenylated acylphloroglucinols, named lindbergins, against promastigotes of L. braziliensis and L. amazonensis . Antiplasmodial and antitrypanosomal activities were already described for phloroglucinol derivatives . Although these protist organisms are not evolutionarily related to T. vaginalis , the variety of biological activities of these compounds against parasites demonstrates the potential of these metabolites on antiprotozoal therapy.…”

Section: Discussionmentioning

confidence: 99%

“…Antiplasmodial and antitrypanosomal activities were already described for phloroglucinol derivatives. [47,48] Although these protist organisms are not evolutionarily related to T. vaginalis, the variety of biological activities of these compounds against parasites demonstrates the potential of these metabolites on antiprotozoal therapy.…”

Section: Discussionmentioning

confidence: 99%

The anti‐Trichomonas vaginalis phloroglucinol derivative isoaustrobrasilol B modulates extracellular nucleotide hydrolysis

et al. 2017

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Trichomonas vaginalis causes trichomoniasis, a neglected sexually transmitted disease. Due to severe health consequences and treatment failure, new therapeutic alternatives are crucial. Phloroglucinols from southern Brazilian Hypericum species demonstrated anti-T. vaginalis and anti-Leishmania amazonensis activities. The modulation of biochemical pathways involved in the control of inflammatory response by ectonucleotidases, NTPDase, and ecto-5'-nucleotidase represents new targets for combating protozoa. This study investigated the activity of phloroglucinol derivatives of Hypericum species from southern Brazil against T. vaginalis as well as its ability on modulating parasite ectonucleotidases and, consequently, immune parameters through ATP and adenosine effects. Phloroglucinol derivatives screening revealed activity for isoaustrobrasilol B (IC 38 μm) with no hemolytic activity. Although the most active compound induced cytotoxicity against a mammalian cell lineage, the in vivo model evidenced absence of toxicity. Isoaustrobrasilol B significantly inhibited NTPDase and ecto-5'-nucleotidase activities, and the immune modulation attributed to extracellular nucleotide accumulation was evaluated. The production of ROS and IL-6 by T. vaginalis-stimulated neutrophils was not affected by the treatment. Conversely, IL-8 levels were significantly enhanced. The associative mechanism of trophozoites death and ectonucleotidases modulation by isoaustrobrasilol B may increase the susceptibility of T. vaginalis to host innate immune cell like neutrophils consequently, contributing to parasite clearance.

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Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds

Cited by 15 publications

References 19 publications

Antiplasmodial natural products: an update

Antiplasmodial natural products: an update

Novel Bioactive Natural Products Isolated from Madagascar Plants and Marine Organisms (2009–2017)

The anti‐Trichomonas vaginalis phloroglucinol derivative isoaustrobrasilol B modulates extracellular nucleotide hydrolysis

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