Targeted Isolation of Monoterpene Indole Alkaloids from <i>Palicourea sessilis</i>

Klein‐Júnior, Luiz Carlos; Cretton, Sylvian; Allard, Pierre‐Marie; Genta‐Jouve, Grégory; Passos, Carolina S.; Salton, Juliana; Bertelli, Pablo Ricardo; Pupier, Marion; Jeannerat, Damien; Heyden, Yvan Vander; Gasper, André Luís de; Wolfender, Jean‐Luc; Christen, Philippe; Henriques, Amélia T.

doi:10.1021/acs.jnatprod.7b00681

Cited by 36 publications

(30 citation statements)

References 38 publications

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“…Similarly to 2 , the competitive losses of 18 Da ( m / z 413 → m / z 395), 32 Da ( m / z 413 → m / z 381) and 70 Da ( m / z 413 → m / z 343) were observed from the secologanin part after the loss of the glucose residue. This fragmentation pattern is in agreement with the MIA 5‐carboxystrictosidine ( 5 ) (Figure S11, supporting information) . In the desoxycordifoline cluster, the ions at m / z 527 and 529 also displayed the competitive losses of 18, 32 and 70 Da after the loss of the glucose residue.…”

Section: Resultssupporting

confidence: 83%

“…Unfortunately, this process is compromised due the scarcity of studies focused on the fragmentation patterns under collision‐induced dissociation for MIAs . More recently, the ability to process MS data on open‐access platforms, such as Global Natural Products Social Molecular Networking (GNPS), using modern tools such as molecular networking (MN) and Library Search (LS), among others, has greatly assisted in the steps of data interpretation and screening of unknown MIAs …”

Section: Introductionmentioning

confidence: 99%

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Molecular networking‐based dereplication of strictosidine‐derived monoterpene indole alkaloids from the curare ingredient Strychnos peckii

Santos

Angolini

Neves

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale Monoterpene indole alkaloids (MIAs) are a large group of biologically active compounds produced by hundreds of plant species in numerous plant families, such as Apocynaceae, Loganiaceae and Rubiaceae. Although this diversity is biosynthetically intermediated by strictosidine, there are no works focused on the fragmentation patterns under collision‐induced dissociation of strictosidine‐derived alkaloids. Methods Initially, the alkaloid fingerprint of Strychnos peckii was established using leaf spray with tandem mass spectrometry (LS‐MS/MS). Then, high‐performance liquid chromatography coupled to tandem mass spectrometry (HPLC/MS/MS) analyses were carried out to focus on the patterns of neutral losses in product ion scan experiments with the leaf aqueous extract. Finally, the product ion spectra from a set of presumable strictosidine‐type derivatives were analyzed and organized via molecular networking (MN), and dereplicated by manual interpretation of MS/MS spectra. Results LS‐MS/MS allowed the tentative identification of strictosidine‐derived alkaloids in the leaves of S. peckii, showing useful neutral losses for the dereplication of strictosidine analogues by HPLC/MS/MS experiments. The use of MN combined with manual interpretation of the fragmentation patterns highlighted characteristic fragmentation pathways, and allowed the tentative identification of strictosidine, desoxycordifoline, strictosidinic acid, 10‐hydroxystrictosidine, 5‐carboxystrictosidine, lyaloside, 3,4‐dehydrostrictosidine and strictosidine lactam. Conclusions The use of MN combined with the analysis of the fragmentation patterns proved to be a useful strategy for the dereplication of strictosidine‐derived MIAs from S. peckii, highlighting known and unprecedented structures, as well as useful diagnostic product ions. Therefore, this workflow is an effective approach for the characterization of strictosidine‐type alkaloids in future dereplication works.

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Section: Resultssupporting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Molecular networking‐based dereplication of strictosidine‐derived monoterpene indole alkaloids from the curare ingredient Strychnos peckii

Santos

Angolini

Neves

et al. 2020

Rapid Comm Mass Spectrometry

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“…As such, valuable natural products are identified from plant extracts or fractions thereof while at the same time massive metadata sets are constructed for these samples, which can be mined under various criteria. For example, such a metabolomics approach was used to focus isolation efforts on previously undescribed compounds from the leaves of Palicourea sessilis [45●●]. An alkaloid fraction of the leaves was analyzed, and MS/MS data were organized as molecular networks [46].…”

Section: Drug Discovery From Plant Natural Productsmentioning

confidence: 99%

Opportunities for plant natural products in infection control

Salam

Quave

2018

Current Opinion in Microbiology

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The continued spread of antimicrobial resistance represents one of the most serious infectious disease threats to global health. There is consensus that a key component of addressing this threat is to replenish the waning pipeline of antimicrobials, with attention being paid to novel mechanisms of action. This includes the development of new classes of classic bacteriostatic and bactericidal antibiotics as well as antivirulence drugs, and it is especially in these areas where plant natural products demonstrate great potential. To this end, we discuss the unique characteristics of plant natural products, the advantages of plants as a resource for anti-infective drug discovery, and recent technologies that have further enabled this path of inquiry. As a result of emerging realization of their advantages, plant natural products have recently enjoyed increased scrutiny in antimicrobial lead discovery, and they will continue to serve as a source of leads. We conclude that plant natural products represent a promising and largely untapped source of new chemical entities from which novel anti-infectives can be discovered.

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“…Many plant extracts demonstrate acetylcholinesterase activity, for example, extract from Crinum jagus containing Amaryllidaceae and isoquinolinone alkaloids [6], Cryptocarya species containing isoquinoline alkaloids [10], Narcissus pseudonarcissus L. containing Amarylidaceae alkaloids [7], Catharanthus roseus containing indole alkaloids [9], secophenanthroindolizidine and proaporphine alkaloids from Cryptocarya densiflora Blume [10], Ocotea percoriacea containing benzylisoquinoline, bisbenzylisoquinoline, aporphine, proaporphine, phenanthrene, and morphinane alkaloids [9], Rauvolfia vomitoria containing monoterpene indole alkaloids [11], Crinum jagus containing Amarylidaceae and isoquinoline alkaloids [6], Lycoris longituba containing Amaryllidaceae alkaloid [12], Psychotria leiocarpa containing alkaloid vincosamide [13], Huperzia serrata containing macrocyclic Lycopodium alkaloids [14], Psychotria nemorosa containing azepine-indole alkaloids [15], Uncaria rhynchophylla containing indole alkaloids [16], Berberis vulgaris containing isoquinoline alkaloids [17], Lycopodium platyrhizoma containing Lycopodium alkaloids [18], Huperzia cunninghamioides containing Lycopodium alkaloids [19], Corydalis mucronifera containing isoquinoline alkaloids [20], Palicourea sessilis containing indole alkaloids [21], and Zephyranthes candida containing galanthamine, plicamine, and secoplicamine [22]. There have also been published articles summarizing the application of plant materials containing alkaloids for inhibition of acetylcholinesterase activity [23,24].…”

Section: Introductionmentioning

confidence: 99%

“…In their method the kinetics of acetylthiocholine iodide hydrolysis by acetylcholinesterase were measured spectrophotometrically. Currently, measurements are most often carried out with the application of 96-well microplates [7,9,12,15,21].…”

Section: Introductionmentioning

confidence: 99%

Application of HPLC-DAD for In Vitro Investigation of Acetylcholinesterase Inhibition Activity of Selected Isoquinoline Alkaloids from Sanguinaria canadensis Extracts

Tuzimski

Petruczynik

2021

Molecules

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Isoquinoline alkaloids may have a wide range of pharmacological activities. Some of them have acetylcholinesterase activity inhibition. Nowadays, neurodegenerative disorders such as Alzheimer’s disease have become a serious public health problem. Searching for new effective compounds with inhibited acetylcholinesterase activity is one of the most significant challenges of modern scientific research. The aim of this study was the in vitro investigation of acetylcholinesterase activity inhibition of extracts obtained from Sanguinaria canadensis collected before, during and after flowering. The acetylcholinesterase activity inhibition of these extracts has not been previously tested. The aim was also to quantify selected alkaloids in the investigated extracts by high performance liquid chromatography (HPLC). The analyses of alkaloid content were performed using HPLC in reversed phase (RP) mode using Polar RP column and mobile phase containing acetonitrile, water and ionic liquid (IL). The acetylcholinesterase activity inhibition of the tested plant extracts and respective alkaloid standards were examined using high performance liquid chromatography with diode-array detector (HPLC-DAD) for the quantification of 5-thio-2-nitro-benzoic acid, which is the product of the reaction between the thiocholine (product of the hydrolysis of acetylthiocholine reaction) with Ellman reagent. The application of the HPLC method allowed for elimination of absorption of interfering components, for example, alkaloids such as sanguinarine and berberine. It is revealed that the HPLC method can be successfully used for the evaluation of the acetylcholinesterase inhibitory activity in samples such as plant extracts, especially those containing colored components adsorbing at wavelength in the range 405–412 nm. The acetylcholinesterase inhibition activity synergy of pairs of alkaloid standards and mixture of all investigated alkaloids was also determined. Most investigated alkaloids and all Sanguinaria canadensis extracts exhibited very high acetylcholinesterase activity inhibition. IC50 values obtained for alkaloid standards were from 0.36 for berberine to 23.13 µg/mL for protopine and from 61.24 to 89.14 µg/mL for Sanguinaria canadensis extracts. Our investigations demonstrated that these plant extracts can be recommended for further in vivo experiments to confirm their acetylcholinesterase activity inhibition.

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Targeted Isolation of Monoterpene Indole Alkaloids from Palicourea sessilis

Cited by 36 publications

References 38 publications

Molecular networking‐based dereplication of strictosidine‐derived monoterpene indole alkaloids from the curare ingredient Strychnos peckii

Molecular networking‐based dereplication of strictosidine‐derived monoterpene indole alkaloids from the curare ingredient Strychnos peckii

Opportunities for plant natural products in infection control

Application of HPLC-DAD for In Vitro Investigation of Acetylcholinesterase Inhibition Activity of Selected Isoquinoline Alkaloids from Sanguinaria canadensis Extracts

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