Insights on profiling of phorbol, deoxyphorbol, ingenol and jatrophane diterpene esters by high performance liquid chromatography coupled to multiple stage mass spectrometry

Nothias-Scaglia, Louis-Félix; Schmitz-Afonso, Isabelle; Renucci, Franck; Roussi, Fanny; Touboul, David; Costa, Jean; Litaudon, Marc; Paolini, Julien

doi:10.1016/j.chroma.2015.09.092

Cited by 27 publications

(46 citation statements)

References 44 publications

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“…Otherwise, diterpenes (tonantzitlolone A, B, C; ent-12α-hydroxy-3,7-dioxoisopimara-8,15-diene and 4′acetoxytonantzitlolone) from Stillingia lineata are evident to have strong anti-CHKIV activity with an EC 50 < 0.8 μg/mL (Techer et al, 2015). A number of promising anti-CHKIV diterpenes have been reported till date (Bourjot et al, 2012;Allard et al, 2012a;Allard et al, 2012b;Bourjot et al, 2014;Corlay et al, 2014;Olivon et al, 2015;Nothias-Scaglia et al, 2015a;Nothias-Scaglia et al, 2015b;Nothias-Scaglia et al, 2015c).…”

Section: Resultsmentioning

confidence: 99%

Diterpenes as lead molecules against neglected tropical diseases

et al. 2016

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Nowadays, neglected tropical diseases (NTDs) are reported to be present everywhere. Poor and developing areas in the world have received great attention to NTDs. Drug resistance, safety profile, and various challenges stimulate the search for alternative medications. Plant-based drugs are viewed with great interest, as they are believed to be devoid of side effects. Diterpenes, a family of essential oils, have showed attractive biological effects. A systematic review of the literature was carried out to summarize available evidences of diterpenes against NTDs. For this, databases were searched using specific search terms. Among the 2338 collected reports, a total of 181 articles were included in this review. Of them, 148 dealt with investigations using single organisms, and 33 used multiple organisms. No mechanisms of action were reported in the case of 164 reports. A total of 93.92% were related to nonclinical studies, and 4.42% and 1.66% dealt with preclinical and clinical studies, respectively. The review displays that many diterpenes are effective upon Chagas disease, chikungunya, echinococcosis, dengue, leishmaniasis, leprosy, lymphatic filariasis, malaria, schistosomiasis, and tuberculosis. Indeed, diterpenes are amazing drug candidates against NTDs. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Resultsmentioning

confidence: 99%

Diterpenes as lead molecules against neglected tropical diseases

et al. 2016

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“…The exact Euphorbia backbone skeleton type could not be identified unambiguously, as many Euphorbia diterpenoid skeletons are isomeric, and their respective MS 2 spectra identical or very similar. A Euphorbia backbone skeleton with masses at m/z 313, 295, 285 can either result from a jatrophane, deoxy tigliane, or ingenane ester like skeleton [37,38]. Furthermore, we were able to see that molecular family (ii) contains substructural Mass2Motifs related to a nicotinoyl side chain.…”

Section: Case Study 1: Annotation Of Euphorbia Specialized Metabolitementioning

confidence: 79%

MolNetEnhancer: enhanced molecular networks by integrating metabolome mining and annotation tools

Ernst

Kang

Caraballo‐Rodríguez

et al. 2019

Preprint

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Metabolomics has started to embrace computational approaches for chemical interpretation of large data sets. Yet, metabolite annotation remains a key challenge. Recently, molecular networking and MS2LDA emerged as molecular mining tools that find molecular families and substructures in mass spectrometry fragmentation data. Moreover, in silico annotation tools obtain and rank candidate molecules for fragmentation spectra. Ideally, all structural information obtained and inferred from these computational tools could be combined to increase the resulting chemical insight one can obtain from a data set. However, integration is currently hampered as each tool has its own output format and efficient matching of data across these tools is lacking. Here, we introduce MolNetEnhancer, a workflow that combines the outputs from molecular networking, MS2LDA, in silico annotation tools (such as Network Annotation Propagation or DEREPLICATOR) and the automated chemical classification through ClassyFire to provide a more comprehensive chemical overview of metabolomics data whilst at the same time illuminating structural details for each fragmentation spectrum. We present examples from four plant and bacterial case studies and show how MolNetEnhancer enables the chemical annotation, visualization, and discovery of the subtle substructural diversity within molecular families. We conclude that MolNetEnhancer is a useful tool that greatly assists the metabolomics researcher in deciphering the metabolome through combination of multiple independent in silico pipelines.

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“…3). Many Euphorbia diterpenoid backbone skeletons are isomeric, and their respective fragmentation spectra are highly similar ( 25 ). Nonetheless, we are able to distinguish different diterpene spectral fingerprints within a molecular family by mapping Mass2Motifs on the mass spectral molecular networks.…”

Section: Main Textmentioning

confidence: 99%

Did a plant-herbivore arms race drive chemical diversity in Euphorbia?

Ernst

Nothias

Hooft³

et al. 2018

Preprint

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The genus Euphorbia is among the most diverse and species-rich plant genera on Earth, exhibiting a near-cosmopolitan distribution and extraordinary chemical diversity, especially across highly toxic macro-and polycyclic diterpenoids. However, very little is known about drivers and evolutionary origins of chemical diversity within Euphorbia. Here, we investigate 43 Euphorbia species to understand how geographic separation over evolutionary time has impacted chemical differentiation. We show that the structurally highly diverse Euphorbia diterpenoids are significantly reduced in species native to the Americas, compared to the Eurasian and African continents, where the genus originated. The localization of these compounds to young stems and roots suggest ecological relevance in herbivory defense and immunomodulatory defense mechanisms match diterpenoid levels, indicating chemoevolutionary adaptation to reduced herbivory pressure.One Sentence SummaryGlobal chemo-evolutionary adaptation of Euphorbia affected immunomodulatory defense mechanisms.

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Insights on profiling of phorbol, deoxyphorbol, ingenol and jatrophane diterpene esters by high performance liquid chromatography coupled to multiple stage mass spectrometry

Cited by 27 publications

References 44 publications

Diterpenes as lead molecules against neglected tropical diseases

Diterpenes as lead molecules against neglected tropical diseases

MolNetEnhancer: enhanced molecular networks by integrating metabolome mining and annotation tools

Did a plant-herbivore arms race drive chemical diversity in Euphorbia?

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