A Complete Survey of Glycoalkaloids Using LC-FTICR-MS and IRMPD in a Commercial Variety and a Local Landrace of Eggplant ( Solanum melongena  L.) and their Anticholinesterase and Antioxidant Activities

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Abstract

Eggplant contains glycoalkaloids (GAs), a class of nitrogen-containing secondary metabolites of great structural variety that may have both adverse and beneficial biological effects. In this study, we performed a complete survey of GAs and their malonylated form, in two genotypes of eggplants: A commercial cultivated type, Mirabella (Mir), with purple peel and bitter taste and a local landrace, named Melanzana Bianca di Senise (Sen), characterized by white peel with purple strip and a typical sweet aroma. Besides the analysis of their morphological traits, nineteen glycoalkaloids were tentatively identified in eggplant berry extracts based upon LC-ESI-FTICR-MS analysis using retention times, elution orders, high-resolution mass spectra, as well as high-resolution fragmentation by IRMPD. The relative signal intensities (i.e., ion counts) of the GAs identified in Mir and Sen pulp extracts showed as solamargine, and its isomers are the most abundant. In addition, anticholinesterase and antioxidant activities of the extracts were evaluated. Pulp tissue was found to be more active in inhibiting acetylcholinesterase enzyme than peel showing an inhibitory effect higher than 20% for Mir pulp. The identification of new malonylated GAs in eggplant is proposed.

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Bioactivities of glycoalkaloids and their aglycones from Solanum species.

Francis Collins, Simon P. Jones, Jaques S. Milner … (2011)

Potatoes, tomatoes, and aubergines are all species of the Solanum genus and contain a vast array of secondary metabolites including calystegine alkaloids, phenolic compounds, lectins, and glycoalkaloids. Glycoalkaloids have been the subject of many literature papers, occur widely in the human diet, and are known to induce toxicity. Therefore, from a food safety perspective further information is required regarding their analysis, toxicity, and bioavailability. This is especially important in crop cultivars derived from wild species to prevent glycoalkaloid-induced toxicity. A comprehensive review of the bioactivity of glycoalkaloids and their aglycones of the Solanum species, particularly focused on comparison of their bioactivities including their anticancer, anticholesterol, antimicrobial, anti-inflammatory, antinociceptive, and antipyretic effects, toxicity, and synergism of action of the principal Solanum glycoalkaloids, correlated to differences of their individual molecular structures is presented.

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A Review of Bioinsecticidal Activity of Solanaceae Alkaloids

Szymon Chowański, Zbigniew Adamski, Pawel Marciniak … (2016)

Only a small percentage of insect species are pests. However, pest species cause significant losses in agricultural and forest crops, and many are vectors of diseases. Currently, many scientists are focused on developing new tools to control insect populations, including secondary plant metabolites, e.g., alkaloids, glycoalkaloids, terpenoids, organic acids and alcohols, which show promise for use in plant protection. These compounds can affect insects at all levels of biological organization, but their action generally disturbs cellular and physiological processes, e.g., by altering redox balance, hormonal regulation, neuronal signalization or reproduction in exposed individuals. Secondary plant metabolites cause toxic effects that can be observed at both lethal and sublethal levels, but the most important effect is repellence. Plants from the Solanaceae family, which contains numerous economically and ecologically important species, produce various substances that affect insects belonging to most orders, particularly herbivorous insects and other pests. Many compounds possess insecticidal properties, but they are also classified as molluscides, acaricides, nematocides, fungicides and bactericides. In this paper, we present data on the sublethal and lethal toxicity caused by pure metabolites and crude extracts obtained from Solanaceae plants. Pure substances as well as water and/or alcohol extracts cause lethal and sublethal effects in insects, which is important from the economical point of view. We discuss the results of our study and their relevance to plant protection and management.

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Jasmonate and ppHsystemin regulate key Malonylation steps in the biosynthesis of 17-Hydroxygeranyllinalool Diterpene Glycosides, an abundant and effective direct defense against herbivores in Nicotiana attenuata.

B. Berger, Purba Mukerjee, Ian T. Baldwin … (2009)

We identified 11 17-hydroxygeranyllinalool diterpene glycosides (HGL-DTGs) that occur in concentrations equivalent to starch (mg/g fresh mass) in aboveground tissues of coyote tobacco (Nicotiana attenuata) and differ in their sugar moieties and malonyl sugar esters (0-2). Concentrations of HGL-DTGs, particularly malonylated compounds, are highest in young and reproductive tissues. Within a tissue, herbivore elicitation changes concentrations and biosynthetic kinetics of individual compounds. Using stably transformed N. attenuata plants silenced in jasmonate production and perception, or production of N. attenuata Hyp-rich glycopeptide systemin precursor by RNA interference, we identified malonylation as the key biosynthetic step regulated by herbivory and jasmonate signaling. We stably silenced N. attenuata geranylgeranyl diphosphate synthase (ggpps) to reduce precursors for the HGL-DTG skeleton, resulting in reduced total HGL-DTGs and greater vulnerability to native herbivores in the field. Larvae of the specialist tobacco hornworm (Manduca sexta) grew up to 10 times as large on ggpps silenced plants, and silenced plants suffered significantly more damage from herbivores in N. attenuata's native habitat than did wild-type plants. We propose that high concentrations of HGL-DTGs effectively defend valuable tissues against herbivores and that malonylation may play an important role in regulating the distribution and storage of HGL-DTGs in plants.

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Journal

Journal ID (nlm-ta): Toxins (Basel)

Journal ID (iso-abbrev): Toxins (Basel)

Journal ID (publisher-id): toxins

Title: Toxins

Publisher: MDPI

ISSN (Electronic): 2072-6651

Publication date (Electronic): 19 April 2019

Publication date Collection: April 2019

Volume: 11

Issue: 4

Electronic Location Identifier: 230

Affiliations

[1 ]Department of Sciences, University of Basilicata, Via dell’Ateneo Lucano, 85100 Potenza (PZ), Italy; filomena.lelario@ 123456unibas.it (F.L.); sabino.bufo@ 123456unibas.it (S.A.B.)

[2 ]School of Agricultural, Forest, Food and Environmental Sciences, University of Basilicata, Via dell’Ateneo Lucano, 85100 Potenza (PZ), Italy; demariasusanna@ 123456libero.it (S.D.M.); annarita.rivelli@ 123456unibas.it (A.R.R.)

[3 ]Spinoff Accademico BioActiPlant, Via dell’Ateneo Lucano, 85100 Potenza (PZ), Italy

[4 ]Department of Geography, Environmental Management & Energy Studies, University of Johannesburg, Auckland Park Kingsway Campus, Johannesburg 2092, South Africa

[5 ]Department of European and Mediterranean Cultures, University of Basilicata, Via San Rocco, 75100 Matera, Italy; laura.scrano@ 123456unibas.it

Author notes

[* ]Correspondence: daniela.russo@ 123456unibas.it (D.R.); luigi.milella@ 123456unibas.it (L.M.); Tel.: +39-0971-205-525 (L.M.)

Author information

Anna Rita Rivelli https://orcid.org/0000-0002-4529-0297

Luigi Milella https://orcid.org/0000-0002-5874-1237

Sabino Aurelio Bufo https://orcid.org/0000-0002-0857-2367

Laura Scrano https://orcid.org/0000-0002-3716-2666

Article

Publisher ID: toxins-11-00230

DOI: 10.3390/toxins11040230

PMC ID: 6521288

PubMed ID: 31010145

SO-VID: d95faf66-0a52-4a37-bf90-ced15c6b643f

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Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

A Complete Survey of Glycoalkaloids Using LC-FTICR-MS and IRMPD in a Commercial Variety and a Local Landrace of Eggplant ( Solanum melongena L.) and their Anticholinesterase and Antioxidant Activities

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Most cited references 45

Bioactivities of glycoalkaloids and their aglycones from Solanum species.

A Review of Bioinsecticidal Activity of Solanaceae Alkaloids

Jasmonate and ppHsystemin regulate key Malonylation steps in the biosynthesis of 17-Hydroxygeranyllinalool Diterpene Glycosides, an abundant and effective direct defense against herbivores in Nicotiana attenuata.

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