Determination and Chemical Profiling of Toxic Pyrrolizidine Alkaloids in Botanical Samples with UPLC–Q-TOFMS

Jeong, Won Tae; Lim, Heung Bin

doi:10.1007/s10337-019-03785-y

Cited by 9 publications

(8 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Considering the various analytical approaches focusing on selectivity and sensitivity, it seems that methods using liquid chromatography-mass spectrometry (LC-MS) are the most preferred, as they combine the physical separation properties of liquid chromatography with the mass analysis provided by mass spectrometry [ 56 , 122 ]. In general, the analysis of PAs in various matrices is a quite challenging task, as outlined in excellent reviews and reports from the last few years tackling analytical methods for PAs in certain feed and food [ 123 , 124 , 125 , 126 ].…”

Section: Global Presence and Use Of Plants Containing Pasmentioning

confidence: 99%

Metabolic Toxification of 1,2-Unsaturated Pyrrolizidine Alkaloids Causes Human Hepatic Sinusoidal Obstruction Syndrome: The Update

Teschke

Noudeng

Quan

et al. 2021

IJMS

View full text Add to dashboard Cite

Saturated and unsaturated pyrrolizidine alkaloids (PAs) are present in more than 6000 plant species growing in countries all over the world. They have a typical heterocyclic structure in common, but differ in their potential toxicity, depending on the presence or absence of a double bond between C1 and C2. Fortunately, most plants contain saturated PAs without this double bond and are therefore not toxic for consumption by humans or animals. In a minority of plants, however, PAs with this double bond between C1 and C2 exhibit strong hepatotoxic, genotoxic, cytotoxic, neurotoxic, and tumorigenic potentials. If consumed in error and in large emouns, plants with 1,2-unsaturated PAs induce metabolic breaking-off of the double bonds of the unsaturated PAs, generating PA radicals that may trigger severe liver injury through a process involving microsomal P450 (CYP), with preference of its isoforms CYP 2A6, CYP 3A4, and CYP 3A5. This toxifying CYP-dependent conversion occurs primarily in the endoplasmic reticulum of the hepatocytes equivalent to the microsomal fraction. Toxified PAs injure the protein membranes of hepatocytes, and after passing their plasma membranes, more so the liver sinusoidal endothelial cells (LSECs), leading to life-threatening hepatic sinusoidal obstruction syndrome (HSOS). This injury is easily diagnosed by blood pyrrolizidine protein adducts, which are perfect diagnostic biomarkers, supporting causality evaluation using the updated RUCAM (Roussel Uclaf Causality Assessment Method). HSOS is clinically characterized by weight gain due to fluid accumulation (ascites, pleural effusion, and edema), and may lead to acute liver failure, liver transplantation, or death. In conclusion, plant-derived PAs with a double bond between C1 and C2 are potentially hepatotoxic after metabolic removal of the double bond, and may cause PA-HSOS with a potential lethal outcome, even if PA consumption is stopped.

show abstract

Section: Global Presence and Use Of Plants Containing Pasmentioning

confidence: 99%

Metabolic Toxification of 1,2-Unsaturated Pyrrolizidine Alkaloids Causes Human Hepatic Sinusoidal Obstruction Syndrome: The Update

Teschke

Noudeng

Quan

et al. 2021

IJMS

View full text Add to dashboard Cite

show abstract

“…The abundance of compounds classified as PAs, greater than 400 to date, and the immense structural diversity exhibited by PAs, including both isobaric constitutional and stereoisomers (Hartmann and Witte, 1995), in conjunction with a relative lack of available standards, has led to the advancement of broadly useful PA detection methods (Jeong and Lim, 2019;These et al, 2013). These techniques do not require corresponding standards as they target key structural fragments of PAs by subjecting them to mass spectrometry (MS) coupled to either liquid or gas chromatography (Jeong and Lim, 2019;Stelljes et al, 1991). In the case of retronecine/heliotridine-type PAs, previous groups have utilized the m/z 120 and 138 fragment ions to detect cyclic diesters and open-chained diesters (Figure 4).…”

Section: Scanning For Retronecine-type Pas Via Hplc-ms/msmentioning

confidence: 99%

“…However, a few other PAs have been documented to contain a base peak of m/z 120 without possession of other key fragments. (Jeong and Lim, 2019) noted the tentative identification of two open chained retronecine-type diesters, symviridine and uplandicine, in which a base peak was m/z 120 and no other common fragments (m/z 138 or 156) were obtained in PIS scans at the collision energies utilized. Another open-chain diester, 7-acetyllycopsamine, was shown to fragment to a base peak of m/z 120 (Colegate et al, 2005;Jeong and Lim, 2019).…”

Section: Asclepiadeae and Periplocoideaementioning

confidence: 99%

“…(Jeong and Lim, 2019) noted the tentative identification of two open chained retronecine-type diesters, symviridine and uplandicine, in which a base peak was m/z 120 and no other common fragments (m/z 138 or 156) were obtained in PIS scans at the collision energies utilized. Another open-chain diester, 7-acetyllycopsamine, was shown to fragment to a base peak of m/z 120 (Colegate et al, 2005;Jeong and Lim, 2019). It is yet to be determined if a common structural feature causes a tendency for particular PAs to result only in a m/z 120 fragment, but it does appear open-chained diesters preferentially result in observation of only an m/z 120 fragment at particular collision energies.…”

Section: Asclepiadeae and Periplocoideaementioning

confidence: 99%

See 1 more Smart Citation

Chemotaxonomic Investigation of Apocynaceae for Retronecine-Type Pyrrolizidine Alkaloids Using HPLC-MS/MS

Barny

Tasca

Sánchez

et al. 2020

Preprint

View full text Add to dashboard Cite

Apocynaceae are well-known for diverse specialized metabolites that are distributed in a phylogenetically informative manner. Pyrrolizidine alkaloids (PAs) have been reported sporadically in one lineage in the family, the APSA clade, but few species had been studied to date. We conduct the first systematic survey of Apocynaceae for retronecine-type PAs, sampling leaves from 231 species from 13 of 16 major lineages within the APSA clade using HPLC-MS/MS. We also follow up on preliminary evidence for infra-specific variation of PA detectability in Echites umbellatus Jacq. Four precursor ion scans (PREC) were developed for a high-throughput survey for chemicals containing a structural moiety common to many PAs, the retronecine core. We identified with high confidence PAs in 7 of 8 sampled genera of tribe Echiteae, but not in samples from the closely related Odontadenieae and Mesechiteae, confirming the utility of PAs as a taxonomic character in tribal delimitation. The presence of PAs in Malouetieae was confirmed, as we report with high confidence their presence in Galactophora schomburgkiana Woodson and Eucorymbia alba Stapf, but currently we have low confidence of their presence in Holarrena pubescens Wall. ex G. Don (the one Malouetieae species where they were previously reported), as well as in Kibatalia macrophylla (Pierre ex Hua) Woodson and in Holarrena curtisii King & Gamble. For the first time the presence of PAs in species of Wrightia R. Br. (Wrightieae) and Marsdenia R. Br. (Marsdenieae) was confirmed. Detectability of PAs was found to vary among samples of Echites umbellatus and intra-individual plasticity contributes to this variation. Of toxicological importance, novel potential sources of human exposure to pro-toxic PAs were identified in the medicinal plants, Wrightia tinctoria R.Br. and Marsdenia tinctoria R.Br., and the food plant, Echites panduratus A. DC., warranting immediate further research to elucidate the structures of the candidate PAs identified. Method development and limitations are discussed.

show abstract

“…However, a disadvantage of these methods is that a standard substance must be retained to identify and quantify individual compounds. Electrospray ionization quadrupole time-of-flight MS (ESI-Q-TOF/MS), a commercial high-resolution mass spectrometry method, is recognized as an excellent platform for profiling various metabolites such as phenolic compounds, alkaloids, and terpenoids because of its ability to identify and quantify unknown compounds without the need for a standard [15]. However, since ESI-Q-TOF/MS cannot accurately quantify some phenolic compounds, analysis is performed by LC-UVD for the simultaneous analysis of other phenolic compounds.…”

Section: Introductionmentioning

confidence: 99%

Establishment of a UPLC-PDA/ESI-Q-TOF/MS-Based Approach for the Simultaneous Analysis of Multiple Phenolic Compounds in Amaranth (A. cruentus and A. tricolor)

et al. 2020

Self Cite

View full text Add to dashboard Cite

We used ultraperformance liquid chromatography coupled with a photodiode-array detector and electrospray ionization quadrupole time-of-flight mass spectrometry (UPLC-PDA/ESI-Q-TOF/MS) to rapidly and accurately quantify 17 phenolic compounds. Then, we applied this method to the seed and leaf extracts of two Amaranthus species to identify and quantify phenolic compounds other than the 17 compounds mentioned above. Compounds were eluted within 30 min on a C18 column using a mobile phase (water and acetonitrile) containing 0.1% formic acid, and the specific wavelength and ion information of the compounds obtained by PDA and ESI-Q-TOF/MS were confirmed. The proposed method showed good linearity (r2 > 0.990). Limits of detection and quantification were less than 0.1 and 0.1 μg/mL, respectively. Intra- and interday precision were less than 2.4% and 1.8%, respectively. Analysis of amaranth seed and leaf extracts using the established method showed that the seeds contained high amounts of 2,4-dihydroxybenzoic acid and kaempferol, and leaves contained diverse phenolic compounds. In addition, six tentatively new phenolic compounds were identified. Moreover, seeds potentially contained 2,3-dihydroxybenzaldehyde, a beneficial bioactive compound. Thus, our method was an efficient approach for the qualitative and quantitative analysis of phenolic compounds, and could be used to investigate phenolic compounds in plants.

show abstract

Determination and Chemical Profiling of Toxic Pyrrolizidine Alkaloids in Botanical Samples with UPLC–Q-TOFMS

Cited by 9 publications

References 28 publications

Metabolic Toxification of 1,2-Unsaturated Pyrrolizidine Alkaloids Causes Human Hepatic Sinusoidal Obstruction Syndrome: The Update

Metabolic Toxification of 1,2-Unsaturated Pyrrolizidine Alkaloids Causes Human Hepatic Sinusoidal Obstruction Syndrome: The Update

Chemotaxonomic Investigation of Apocynaceae for Retronecine-Type Pyrrolizidine Alkaloids Using HPLC-MS/MS

Establishment of a UPLC-PDA/ESI-Q-TOF/MS-Based Approach for the Simultaneous Analysis of Multiple Phenolic Compounds in Amaranth (A. cruentus and A. tricolor)

Contact Info

Product

Resources

About