Mass spectrometry for characterization of homologous piperidine alkaloids and their activity as acetylcholinesterase inhibitors

Freitas, Thamires Rodrigues; Danuello, Amanda; Júnior, Cláudio Viegas; Bolzani, Vanderlan S.; Pivatto, Marcos

doi:10.1002/rcm.8172

Cited by 16 publications

(15 citation statements)

References 25 publications

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“…Alternatively, tandem mass spectrometry (MS/MS)‐based techniques have been successfully used for determination of natural product isomers, such as phenolics, diterpenes and alkaloids 29–31 . Electrospray ionization tandem mass spectrometry (ESI‐MS/MS) using collision‐induced dissociation (CID) is a very valuable tool for the analyses of labile compounds with low vapor pressures and/or highly polar chemical functionalities 32 …”

Section: Introductionmentioning

confidence: 99%

Fragmentation study of clerodane diterpenes from Casearia species by tandem mass spectrometry (quadrupole time‐of‐flight and ion trap)

Danuello

Castro

Pilon

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale Clerodane‐type diterpenes from Casearia species show important pharmacological activites such as antitumor, antimicrobial and anti‐inflamatory. There are several mass spectrometry (MS)‐based methods for identification of diterpenes; however, there is still a lack of MS procedures capable of providing characteristic fragmentation pathways for a rapid and unambiguous elucidation of casearin‐like compounds. Methods Casearin‐like compounds were investigated by electrospray ionization tandem mass spectrometry (ESI‐MS/MS). The fragmentation studies were carried out by tandem mass spectrometry in space (quadrupole time‐of‐flight (QTOF)) using different collision energies and also by tandem mass spectrometry in time (QIT) by selective isolation of product ions. Results Casearin‐like compounds presented a predominance of sodium‐ and potassium‐cationized precursor ions. Both QIT and QTOF techniques provided sequential neutral losses of esters related to the R1 to R5 substituents linked to the nucleus of the clerodane diterpenes. The fragmentation pathway is initiated with a cleavage of the ester moieties R2 followed by the elimination of the ester groups R3, both losing neutral carboxylic acids. Using QIT, it was also possible to observe the cleavage of the ester groups R1 or R5 by MS4 experiments. Conclusions Through a rational analysis of the fragmentation mechanisms of Casearia diterpenes it was possible to suggest an annotation strategy based on the sequential cleavages of the ester groups related to the R2, R3 and R5 substituents. These results will assist studies of the dereplication and metabolomics involving casearin‐like compounds present in complex extracts of Casearia species.

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Section: Introductionmentioning

confidence: 99%

Fragmentation study of clerodane diterpenes from Casearia species by tandem mass spectrometry (quadrupole time‐of‐flight and ion trap)

Danuello

Castro

Pilon

et al. 2020

Rapid Comm Mass Spectrometry

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“…Both fractions exhibited 2 major peaks at RT 2.57 (1) and 6.14 (2) mins, however, the ethyl acetate fraction also gave several minor peaks at RT approximately 6.9 -17.9 mins which was not seen in the n-butanol fraction. Based on the MS/MS data (Table 2) and comparison to the literature, the two major peaks were identified as cassine (1) and spectaline (2) ( Figure 5) [20,21]. In the ethyl acetate fraction, a peak at RT 6.95 mins was observed, which was identified as 3-O-acetylspectaline (3).…”

Section: Identification Of Metabolites By Lc-ms/msmentioning

confidence: 89%

“…Viegas et al (2005) and Castro et al (2008) have developed semisynthetic derivatives from (-) spectaline isolated from the flower of C. spectabilis, the compounds exhibited inhibition against rat brain cholinesterase [27,28]. Freitas et al (2018) have reported that the chloridrate form of cassine, spectaline, and 3-O-acetylspectaline demonstrated acetylcholinesterase inhibitory activity [21]. Based on the findings, it is possible that the cholinesterase inhibitory activity in the ethyl acetate and the n-butanol fractions of C. spectabilis corresponded to the presence of cassine, spectaline, and 3-O-acetylspectaline.…”

Section: Identification Of Metabolites By Lc-ms/msmentioning

confidence: 99%

Evaluation of cholinesterase inhibitory activity of six Indonesian Cassia species

Suciati¹,

Laili²,

Poerwantoro³

et al. 2020

jrp

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Alzheimer's disease (AD) is a neurodegenerative disorder, which is the most common cause of dementia. The aging population means that the number of people suffering from AD is expected to increase each year if there is no effective treatment found. One of the strategies for the treatment of AD is the use of cholinesterase inhibitors. Plants have been the source of many bioactive metabolites, including cholinesterase inhibitors. The objective of this study is to investigate the potency of several plant extracts from the genus Cassia as cholinesterase inhibitors. The cholinesterase inhibitory screening was carried out against two enzymes, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), according to the modified Ellman's method. The chemistry of the active fractions was studied by LC-MS/MS method. The results suggested that amongst six plant extracts from the genus Cassia investigated, the ethanolic extract of Cassia spectabilis showed the strongest inhibition against both AChE and BChE enzymes, with IC50 values of 39.5 and 36.9 µg/mL, respectively. Investigation on the n-hexane, ethyl acetate, and nbutanol fractions obtained from the C. spectabilis extract showed that the ethyl acetate and the n-butanol fractions gave better inhibitory activity compared to the n-hexane fraction. Based on the LC-MS/MS data, the two active fractions gave similar profile. Both fractions contained alkaloid cassine and spectaline, which may responsible for the cholinesterase inhibitory activity.

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“…The utilization of Prosopis juliflora as primary or sole wellspring of nourishment causes an ailment in creatures referred to locally as "caratorta" ailment in Brazil because of neurotoxic piperidine compound in P. juliflora leaves and cases [75]. Piperidine alkaloids from Senna spectabilis establish an uncommon class of natural products with a few organic exercises [76]. In society prescription, this plant is shown for the treatment of obstruction, sleep deprivation, uneasiness, epilepsy, jungle fever, looseness of the bowels and cerebral pain [77].…”

Section: Pyrrole: Stachydrinementioning

confidence: 99%

Chemistry of Secondary Metabolites

Mohiuddin¹

2019

ACT

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Medicinal plants, are known to deliver a wide scope of Plant Secondary Metabolites (PSMs) connected as bug sprays, medications, colors and poisons in farming, prescription, industry and biofighting in addition to bio-fear mongering, separately. Be that as it may, creation of PSMs is for the most part in little amounts, so we have to discover novel approaches to increment both amount and nature of them. Luckily, biotechnology proposes a few choices through which secondary metabolism in plants can be built in imaginative approaches to: 1) over-produce the valuable metabolites, 2) down-produce the poisonous metabolites, 3) produce the new metabolites. Secondary metabolites are extensively characterized as natural products integrated by a life form that is not basic to help development and life. The plant kingdom fabricates more than 200,000 unmistakable chemical compounds, a large portion of which emerge from particular metabolism. While these compounds assume critical jobs in interspecies challenge and safeguard, many plant natural products have been abused for use as prescriptions, scents, flavors, supplements, repellants, and colorants. In spite of this immense chemical decent variety, numerous secondary metabolites are available at low focuses in plant a, taking out yield based assembling as methods for achieving these imperative products. The basic and stereo chemical unpredictability of particular metabolites frustrates most endeavors to get to these compounds utilizing chemical blend. Albeit local plants can be built in amass target pathway metabolites. This Update gives a concise outline of designing plant secondary metabolism in microbial frameworks. We quickly diagram biosynthetic pathways intervening arrangement of the real classes of natural products with an accentuation on high-esteem terpenoids, alkaloids, phenylpropanoids, and polyketides. We additionally feature basic topics, techniques, and provoke hidden endeavors to reproduce and build these pathways in microbial hosts. We center mostly around again biosynthetic methodologies in which plant specific metabolites are combined straightforwardly from sugar feed stocks instead of enhanced forerunners or intermediates.

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Mass spectrometry for characterization of homologous piperidine alkaloids and their activity as acetylcholinesterase inhibitors

Abstract: The ESI-MS/MS and EI-MS studies allowed us to propose fragmentation mechanisms for piperidine alkaloids and derivatives. Therefore, mass spectrometry is an important tool for characterizing the structure of these compounds and for supporting further metabolomics studies.

Cited by 16 publications

References 25 publications

Fragmentation study of clerodane diterpenes from Casearia species by tandem mass spectrometry (quadrupole time‐of‐flight and ion trap)

Fragmentation study of clerodane diterpenes from Casearia species by tandem mass spectrometry (quadrupole time‐of‐flight and ion trap)

Evaluation of cholinesterase inhibitory activity of six Indonesian Cassia species

Chemistry of Secondary Metabolites

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