Antimicrobial and phytotoxic activities of secondary metabolites from Haplophyllum tuberculatum and Chrysanthemum coronarium

Abdelgaleil, Samir A. M.; Saad, Mona M. G.; Ariefta, Nanang Rudianto; Shiono, Yoshihito

doi:10.1016/j.sajb.2019.10.005

Cited by 22 publications

(14 citation statements)

References 30 publications

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“…Seed germination test (phytotoxicity assay). The phytotoxicity of tryptoquialanine A on seed germination was evaluated as previously described with a few modifications (42)(43)(44)(45). Briefly, C. sinensis seeds were manually collected from oranges purchased at a local grocery store (Campinas, São Paulo, Brazil).…”

Section: Methodsmentioning

confidence: 99%

Phytotoxic Tryptoquialanines Produced In Vivo by Penicillium digitatum Are Exported in Extracellular Vesicles

Costa

Bazioli

Barbosa

et al. 2021

mBio

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Penicillium digitatum is the most aggressive pathogen of citrus fruits. Tryptoquialanines are major indole alkaloids produced by P. digitatum. It is unknown if tryptoquialanines are involved in the damage of citrus fruits caused by P. digitatum. To investigate the pathogenic roles of tryptoquialanines, we initially asked if tryptoquialanines could affect the germination of Citrus sinensis seeds. Exposure of the citrus seeds to tryptoquialanine A resulted in a complete inhibition of germination and an altered metabolic response. Since this phytotoxic effect requires the extracellular export of tryptoquialanine A, we investigated the mechanisms of extracellular delivery of this alkaloid in P. digitatum. We detected extracellular vesicles (EVs) released by P. digitatum both in culture and during infection of citrus fruits. Compositional analysis of EVs produced during infection revealed the presence of a complex cargo, which included tryptoquialanines and the mycotoxin fungisporin. The EVs also presented phytotoxicity activity in vitro and caused damage to the tissues of citrus seeds. Through molecular networking, it was observed that the metabolites present in the P. digitatum EVs are produced in all of its possible hosts. Our results reveal a novel phytopathogenic role of P. digitatum EVs and tryptoquialanine A, implying that this alkaloid is exported in EVs during plant infection. IMPORTANCE During the postharvest period, citrus fruits can be affected by phytopathogens such as Penicillium digitatum, which causes green mold disease and is responsible for up to 90% of total citrus losses. Chemical fungicides are widely used to prevent green mold disease, leading to concerns about environmental and health risks. To develop safer alternatives to control phytopathogens, it is necessary to understand the molecular basis of infection during the host-pathogen interaction. In the P. digitatum model, the virulence strategies are poorly known. Here, we describe the production of phytotoxic extracellular vesicles (EVs) by P. digitatum during the infection of citrus fruits. We also characterized the secondary metabolites in the cargo of EVs and found in this set of molecules an inhibitor of seed germination. Since EVs and secondary metabolites have been related to virulence mechanisms in other host-pathogen interactions, our data are important for the comprehension of how P. digitatum causes damage to its primary hosts.

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Section: Methodsmentioning

confidence: 99%

Phytotoxic Tryptoquialanines Produced In Vivo by Penicillium digitatum Are Exported in Extracellular Vesicles

Costa

Bazioli

Barbosa

et al. 2021

mBio

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“…The search for a single highly bioactive compound does not adequately consider the interaction of the intricate and concatenated network of secondary metabolites present in medicinal plants [ 22 ]. Antimicrobial activity is a good example in this context, since plants are composed of complex phytochemical pools of compound combinations designed to fight infections, and often molecules isolated from plant sources have exhibited lower antimicrobial activities compared to the whole extracts [ 23 , 24 ]. However, the study of plant extracts remains inherently complex and is often exacerbated by rampant variation due to genetic traits and/or environmental factors that influence the production of secondary metabolites by plants.…”

Section: Introductionmentioning

confidence: 99%

Unravelling the Antibacterial Activity of Terminalia sericea Root Bark through a Metabolomic Approach

et al. 2020

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Terminalia sericea Burch. ex. DC. (Combretaceae) is a popular remedy for the treatment of infectious diseases. It is widely prescribed by traditional healers and sold at informal markets and may be a good candidate for commercialisation. For this to be realised, a thorough phytochemical and bioactivity profile is required to identify constituents that may be associated with the antibacterial activity and hence the quality of raw materials and consumer products. The aim of this study was to explore the phytochemistry and identify the antibacterial constituents of T. sericea root bark, using a metabolomic approach. The chemical profiles and antibacterial activities of 42 root bark samples collected from three districts in the Limpopo Province, South Africa, were evaluated. Dichloromethane:methanol (1:1) extracts were analysed using ultraperformance liquid chromatography (UPLC)-mass spectrometry (MS), and chemometric models were constructed from the aligned data. The extracts were tested against Bacillus cereus (ATCC 11778), Staphylococcus epidermidis (ATCC 12223), Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 8739), Klebsiella pneumoniae (ATCC 13883), Pseudomonas aeruginosa (ATCC 27853), Shigella sonnei (ATCC 9292) and Salmonella typhimurium (ATCC 14028), using the minimum inhibition microdilution assay. Nine compounds; sericic acid, sericoside, resveratrol-3-O-β-rutinoside, ellagic acid, flavogallonic acid dilactone, methyl-flavogallonate, quercetin-3-(2′′-galloylrhamnoside), resveratrol-3-(6′′-galloyl)-O-β-d-glucopyranoside and arjunetin, were isolated from the root bark. All the compounds, with the exception of sericic acid, sericoside and resveratrol-3-O-β-rutinoside, were isolated for the first time from the root bark of T. sericea. Chemometric analysis revealed clustering that was not population specific, and the presence of three groupings within the samples, characterised by sericic acid, sericoside and an unidentified compound (m/z 682/4.66 min), respectively. The crude extracts from different populations displayed varied antibacterial activities against S. typhimurium (minimum inhibitory concentrations (MICs) 0.25–1.0 mg/mL), but similar activity towards Bacillus cereus (1.0 mg/mL). Several compounds present in the root bark were highly active towards all or most of the pathogens tested, but this activity was not reflected by the chemical profiles of extracts prepared from the individual samples. Among the pure compounds tested, only flavogallonic acid dilactone and methyl-flavogallonate exhibited broad-spectrum activity. A biochemometric analysis indicated that there was no consistent association between the levels of phytochemicals and the activity of the active or non-active extracts. Although it was deduced that the major constituents of T. sericea root bark contributed to the chemotypic variation, further investigation of the interactions of compounds present in the root bark may provide antibacterial efficacies not evident when examining compounds singularly. The data reported herein will provide information that is fundamentally important for the development of quality control protocols.

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“…tuberculatum showed antimicrobial evaluation against a variety of strains, revealed moderate effect against B. subtilis, S. choleraesuis and E. coli, gentamycin sulphate; it has 75% potency as antibacterial agent on S.aureus and E.coli. It is the most potent inhibitor against plant pathogenic bacteria and fungi (Al-Burtamani et al, 2005;Sabry et al, 2016;Abdelgaleil et al, 2020). Available literature shows that no earlier study has been performed on the antibacterial characters of A.nilotica gum until 2013.Study of methanolic extract of A. nilotica revealed moderate antibacterial effect (14-18 mm) against E. coli (ATCC 25922);aqueous extracts of A. nilotica had no effects of antibacterial characters against all tested bacteria (Mahjoub, 2013).…”

Section: Introductionmentioning

confidence: 99%

Antibacterial properties of traditional Sudanese medicinal materials against selected enteric bacterial strains

Mahjoub¹

2020

Afr. J. Microbiol. Res.

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Antimicrobial and phytotoxic activities of secondary metabolites from Haplophyllum tuberculatum and Chrysanthemum coronarium

Cited by 22 publications

References 30 publications

Phytotoxic Tryptoquialanines Produced In Vivo by Penicillium digitatum Are Exported in Extracellular Vesicles

Phytotoxic Tryptoquialanines Produced In Vivo by Penicillium digitatum Are Exported in Extracellular Vesicles

Unravelling the Antibacterial Activity of Terminalia sericea Root Bark through a Metabolomic Approach

Antibacterial properties of traditional Sudanese medicinal materials against selected enteric bacterial strains

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