Isoquinoline Alkaloids and Chemotaxonomy

Santos, Anderson R. dos; Vaz, Nelissa P.

doi:10.1007/978-3-030-30746-2_8

Cited by 4 publications

(7 citation statements)

References 66 publications

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“…33,34 Reticuline is an important branch-point intermediate in the biosynthesis of more complex isoquinoline alkaloids such as protoberberine, benzophenanthridines, and aporphines. 35 DESI-MS n data of all aporphine alkaloids detected are described in Table 1. All compounds were submitted to fragmentation up to MS 6 or MS 7 .…”

Section: Desorption Electrospray Ionization Mass Spectrometrymentioning

confidence: 99%

Identification of Sassafras albidum alkaloids by high‐performance thin‐layer chromatography tandem mass spectrometry and mapping by desorption electrospray ionization mass spectrometry imaging

et al. 2020

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Sassafras albidum is an important tree species that occurs across North America. The presence of benzylisoquinoline and aporphine alkaloids has been previously described; however, the spatial distribution of these compounds within S. albidum and other plants of Lauraceae family is still unclear. Mass spectrometry imaging has become an important tool in analysis of plants metabolites, uncovering important contributions about the functional role, biosynthetic pathway, and accumulation of these compounds in the plant. This work aimed to identify further alkaloids present in S. albidum roots, twigs, and leaves by high‐performance thin‐layer chromatography coupled to desorption electrospray ionization multistage mass spectrometry (HPTLC DESI‐MSn) and to map the spatial distribution of these compounds by DESI‐MS imaging. A total of 12 alkaloids were indentified in the roots and twigs, and six of them were detected for the first time in S. albidum. A high number of alkaloids was found in S. albidum roots; however, alkaloids were not detected in the leaves. Cross sections of roots and twigs were blotted onto TLC plates assisted by heating and solvent extraction, and these imprints were analyzed by DESI‐MS imaging. The profile of alkaloid spatial distribution in DESI‐MS images showed different accumulation patterns across and within different plant parts. Most alkaloids displayed higher intensities in the outer‐most layer of the roots and twigs. The detailed spatial localization pattern of these alkaloids analyzed by DESI‐MS imaging in different plant parts could contribute to a better understanding of the profile of distribution, accumulation, and biosynthesis of benzylisoquinoline and aporphine alkaloids.

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Section: Desorption Electrospray Ionization Mass Spectrometrymentioning

confidence: 99%

Identification of Sassafras albidum alkaloids by high‐performance thin‐layer chromatography tandem mass spectrometry and mapping by desorption electrospray ionization mass spectrometry imaging

et al. 2020

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“…Isoquinolines are alkaloids vastly found in nature and they are mostly predominant in Papaveraceae , Berberidaceae , and Ranunculaceae plant families. Isoquinolines present a protective role against herbivores, disease‐causing agents, such as bacteria, fungi, and viruses, and ultraviolet radiation (dos Santos & Vaz, 2019). Bacteria and fungi induce plant tissues destruction, whereas viruses promote plant disease, such as plant stunting, tissue necrosis, and leaf yellowing, which may lead to plant death (Waller, 1993).…”

Section: Introductionmentioning

confidence: 99%

“…Isoquinolines biosynthetically derived from tyrosine and phenylalanine are formed by the reaction of l ‐dopamine and 4‐hydroxyphenylacetaldeyde with further decarboxylation (Khan & Suresh Kumar, 2015; dos Santos & Vaz, 2019). Briefly, in general, isoquinoline biosynthesis begins with two L‐tyrosine molecules: one molecule is decarboxylated by l ‐tyrosine decarboxylase, and the second is transaminated by l ‐tyrosine transaminase (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

“…The products formed from decarboxylation and transamination reactions react together forming S‐norcoclaurine, which undergoes several reactions to form S‐reticuline, the precursor of protoberberines, aporphines and benzophenanthridines, and other alkaloids subclasses. S‐reticuline can undergo two more reactions to form R‐reticuline, the precursor of morphinan alkaloids (Hudlicky et al, 1995; dos Santos & Vaz, 2019).…”

Section: Introductionmentioning

confidence: 99%

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Isoquinolines alkaloids and cancer metabolism: Pathways and targets to novel chemotherapy

Mello

Zancan

2022

Chem Biol Drug Des

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Cancer is one of the main causes of death in the world. This is a complex disease where the development of resistance to chemotherapy is frequent driving the search for new anticancer compounds. In this sense, isoquinolines have gained attention in the past few years. This review aims to highlight the new advances related to the use of isoquinolines compounds against cancer cells, and we point out targets for their anti-tumor action. Isoquinolines are compounds found in plants that are important for their protection. In cancer, many representatives of this class of compounds have demonstrated their efficacy against cancer by acting on cancer metabolism, such as triggering cell death, reducing pro-survival protein expression, inducing ROS production, inhibiting pro-survival cell signaling pathways, among other effects. The mechanisms triggered by isoquinolines in cancer cells represent robust anticancer strategies, which support that this class of compounds are strong candidates for cancer treatment.

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“…In terms of structural diversity, isoquinoline alkaloids (IQAs) are considered to be the second-largest class of alkaloids in medicinal plants . IQAs possess a wide spectrum of biological activities, including antirheumatoid arthritis, antialzheimer, anticonvulsant, and antihyperglycemic, which have aroused great interest in chemists and pharmacists .…”

Section: Introductionmentioning

confidence: 99%

Eco-friendly Deep Eutectic Solvents Contribute to Improving the Separation of Isoquinoline Alkaloids in Supercritical Fluid Chromatography

Jiang

Liu

et al. 2020

ACS Sustainable Chem. Eng.

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In this work, for the first time, 10 isoquinoline alkaloids (IQAs) were separated and determined by supercritical fluid chromatography (SFC) utilizing eco-friendly deep eutectic solvents (DESs) as novel mobile phase additives. The effects of DES types, DES concentrations, and other chromatographic parameters on the separation of IQAs were systematically optimized. Improved resolution of alkaloids and decreased peak tailing were distinctly observed when DESs were added to the mobile phase. The supercritical CO 2 and MeOH-2% H 2 O-0.5% FA-0.25% ChCl-Gly were used as the optimized mobile phase, and the 10 IQAs were well separated in SFC. The separation mechanism might be attributed to the fact that DESs were used as silanol blockers to compete for the adsorption sites with IQAs on the silica surface. The present study suggests that the separation of IQAs from complex samples in SFC can be effectively improved using DESs as mobile phase additives. Moreover, the proposed "green" method for analyzing IQAs focuses on reducing the use of organic solvents and improving the applicability for alkaloid analysis.

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Isoquinoline Alkaloids and Chemotaxonomy

Cited by 4 publications

References 66 publications

Identification of Sassafras albidum alkaloids by high‐performance thin‐layer chromatography tandem mass spectrometry and mapping by desorption electrospray ionization mass spectrometry imaging

Identification of Sassafras albidum alkaloids by high‐performance thin‐layer chromatography tandem mass spectrometry and mapping by desorption electrospray ionization mass spectrometry imaging

Isoquinolines alkaloids and cancer metabolism: Pathways and targets to novel chemotherapy

Eco-friendly Deep Eutectic Solvents Contribute to Improving the Separation of Isoquinoline Alkaloids in Supercritical Fluid Chromatography

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