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Discriminative Metabolomics Analysis and Cytotoxic Evaluation of Flowers, Leaves, and Roots Extracts of Matthiola longipetala subsp. livida

Phytochemistry and Plant Systematics Department, Division of Pharmaceutical Industries, National Research Centre, Cairo P.O. Box 12622, Egypt
Author to whom correspondence should be addressed.
Metabolites 2023, 13(8), 909;
Submission received: 28 June 2023 / Revised: 27 July 2023 / Accepted: 31 July 2023 / Published: 3 August 2023
(This article belongs to the Special Issue Progress in Metabolomic Analysis in Medicinal Plants)


Matthiola longipetala subsp. livida is an annual herb in Brassicaceae that has received little attention despite the family’s high reputation for health benefits, particularly cancer prevention. In this study, UPLC-HRMS-MS analysis was used for mapping the chemical constituents of different plant parts (i.e., flowers, leaves, and roots). Also, spectral similarity networks via the Global Natural Products Social Molecular Networking (GNPS) were employed to visualize their chemical differences and similarities. Additionally, the cytotoxic activity on HCT-116, HeLa, and HepG2 cell lines was evaluated. Throughout the current analysis, 154 compounds were annotated, with the prevalence of phenolic acids, glucosinolates, flavonol glucosides, lipids, peptides, and others. Predictably, secondary metabolites (phenolic acids, flavonoids, and glucosinolates) were predominant in flowers and leaves, while the roots were characterized by primary metabolites (peptides and fatty acids). Four diacetyl derivatives tentatively assigned as O-acetyl O-malonyl glucoside of quercetin (103), kaempferol (108 and 112), and isorhamnetin (114) were detected for the first time in nature. The flowers and leaves extracts showed significant inhibition of HeLa cell line propagation with LC50 values of 18.1 ± 0.42 and 29.6 ± 0.35 µg/mL, respectively, whereas the flowers extract inhibited HCT-116 with LC50 24.8 ± 0.45 µg/mL, compared to those of Doxorubicin (26.1 ± 0.27 and 37.6 ± 0.21 µg/mL), respectively. In conclusion, the flowers of M. longipetala are responsible for the abundance of bioactive compounds with cytotoxic properties.

Graphical Abstract

1. Introduction

Brassicaceae (=Cruciferae) is one of the economically important angiosperm families, commonly known as the crucifers, cabbage, or mustard family, containing over 372 genera and approximately 4636 species [1]. Plants of the family Brassicaceae have been an interesting research subject for years due to their economic and agricultural importance. Many species have been valued as food crops; some are vegetables, others are sources of industrial and cooking oils, forage, and condiments and others are grown as ornamental species for their showy flowers and significant numbers as medicinal herbs [2]. Additionally, certain wild cruciferous plants are rich in secondary metabolites, especially glucosinolates, phenolic acids, and flavonoids, which have many biological activities and, therefore, numerous nutritional and medicinal benefits [3,4]. Matthiola longipetala subsp. livida (Delile) Maire is one of the common wild medicinal cruciferous herbs growing mainly in the Egyptian Mediterranean region, and it is locally known as “Manthor” [5]. Although some previous phytochemical studies have been conducted on M. longipetala subsp. livida [6,7,8,9], the reported compounds represent only a small portion of the species’ chemical composition. Similarly, certain biological activities such as antibacterial, antifungal, and anticancer effects have been reported for the investigated species [8,9,10].
Lately, metabolomics platforms have been widely used to map the metabolome of plants, among which ultra-performance liquid chromatography coupled with high-resolution tandem mass spectrometry (UPLC-HRMS/MS) as the most extensively adopted for mapping the secondary metabolome space. UPLC-HRMS/MS offers the advantages of high efficiency, reproducibility, and shorter analysis [11]. Additionally, advances in the data analysis tools, such as molecular networks through the Global Natural Products Social Molecular Networking (GNPS) [12], allow for the visual display of the constitutive metabolome among samples and the propagation of metabolites annotation [13].
Over the last few decades, most new therapeutic interventions involving plant secondary metabolites and their derivatives have been aimed at combating cancer. In this regard, cruciferous plants have been previously reported to lower the risk of developing various cancers [14]. Our previous research reported the moderate cytotoxic potential of the alcoholic extract of the aerial part of M. longipetala subsp. livida against cervix (HeLa) and colon (HCT116) cell lines [8]. Moreover, another report assessed the extract’s activity against HepG2 cells in vitro using MTT, DNA fragmentation, and cell proliferation cycle measurements, and it demonstrated significant activity [15].
In continuation of our previous study, the present work aimed to map the under-explored chemistries of different organs (i.e., flowers, leaves, and roots) of M. longipetala using UPLC–HRMS-MS analysis that recruited for a holistic overview of the plant’s constitutive chemistries, coupled with spectral similarity networks through the GNPS [12]; this was in addition to evaluating the cytotoxic activities of the three organs on HCT-116, HeLa, and HepG2 cell lines to suggest the one responsible for this potential.

2. Materials and Methods

2.1. Chemicals and Reagents

All chemicals for chemical analysis were obtained from Sigma-Aldrich (Merck, Kenilworth, NJ, USA).

2.2. Plant Material and Preparation of the Extracts

M. longipetala subsp. livida (650 g fresh weight) was collected from Alexandria-Marsa Matruh Road, 31°04′15.3″ N 27°58′10.4″ E, Egypt, in February 2018. The identity of the plant was authenticated by Prof. Dr. Mona M. Marzouk. A voucher specimen (ML_28_2_18) was placed in the herbarium of the National Research Centre (CAIRC), Cairo, Egypt. The flowers, leaves, and roots (117, 175, and 152 g fresh weight, respectively) were washed thoroughly with bi-distilled H2O, dried in shade, and ground finely. Fifteen grams of each dried powdered organ was separately extracted using 70% methanol (500 mL) by sonication (2 h, 60 °C) and filtered over charcoal to yield three aqueous methanolic extracts [16,17]. The flowers, leaves, and roots extracts were concentrated under reduced pressure at 50 °C to produce three dried extracts (2.761, 1.140, and 1.832 g, respectively).

2.3. Sample Preparation for UPLC-HRMS-MS Measurement

The dried extracts were prepared for UPLC-HRMS/MS analyses following a previously described protocol [16]. The extracts (50 mg each) were dissolved in 70% MeOH (HPLC-grade) with sonication (10 min), then centrifuged. Aliquots were then evaporated under reduced pressure, followed by freeze-drying for 48 h. For MS analysis, 1 mg in 250 µL MeOH (MS-grade) were prepared consuming 5 µL as an injection volume in the UPLC-MS analysis.

2.4. UPLC-HRMS-MS Analysis

The HRMS/MS analysis was conducted on a MaXis 4G instrument (Bruker Daltonics®, Bremen, Germany) coupled with an Ultimate 3000 UPLC (Thermo Fisher Scientific®, Waltham, MA, USA). A UPLC method was applied as described by [17] as follows: (with 0.1% formic acid in H2O as solvent A and 100% ACN as solvent B), an isocratic gradient of 10% B for 10 min, 10% to 100% B in 30 min, 100% B for an additional 10 min, using a flow rate of 0.3 mL/min; 5 µL injection volume and UV detector (UV/VIS) wavelength monitoring at 210, 254, 280, and 360 nm. The separation was conducted on a Nucleoshell RP 18 column, 2.7 µm, 150 × 2 mm (Macherey-Nagel®, Düren, Germany), and the range for MS acquisition was 50–1800 Daltons (Da). A capillary voltage of 4500 V, nebulizer gas pressure (nitrogen) of 2 (1.6) bar, ion source temperature of 200 °C, dry gas flow of 9 L/min, and spectral rates of 3 Hz for MS1 and 10 Hz for MS2, were utilized. For acquiring MS/MS fragmentation, the 10 most intense ions per MS1 were selected for subsequent CID, with stepped CID energy applied. The employed parameters for tandem MS were applied as previously detailed [18].

2.5. Data Analysis and Preprocessing

Raw data inspection was performed using Compass Data Analysis 4.4 (Bruker Daltonics®). A Metaboscape 3.0 (Bruker Daltonics®) was utilized for feature detection, grouping, and alignment, employing the T-ReX 3D (Time aligned Region Complete eXtraction) algorithm [19]. Bucketing was performed with an intensity threshold of 1 × 105 and a retention time range from 0 to 40 min with a restricted mass range m/z from 130 to 1800.

2.6. Feature-Based Molecular Networking (FBMN) and Metabolites Dereplication

The produced MGF file and the feature quantification table (CSV file) were used in the feature-based molecular networking (FBMN) following the online workflow in GNPS platform (, accessed on 28 December 2019 [20]. The parameters applied for the construction of the FBMN via the GNPS platform as follows: a parent mass tolerance (0.05 Da), a fragment ion tolerance (0.05 Da), a cosine score (0.7), and minimum shared fragments (6). To avoid misinterpretation of artifacts, the blank run was uploaded as a distinct sample on GNPS workflow and excluded from the networks. Cytoscape version 3.9.1 (, accessed on 28 February 2022, was used for the network visualization.
The metabolites’ dereplication was based on the chromatographic performance, chemical formula, and fragmentation pattern compared to those of MS2 data from literature and spectra from MS reference database (MoNA, NIST14, and Respect) (Table 1). Sirius plus CSI:FingerID 5.5.4 were used for the manual putative structures identification [21], assisted by the molecular formula prediction (C, H, N, O, S, and P) and candidate search with m/z tolerance set to 20 ppm connected to online Pubchem. The proposed in silico fragmentation trees are the impetus for further support for identification.

2.7. Cytotoxic Activity

2.7.1. Cell Lines

Human tumor cell lines: the colon carcinoma (HCT116), cervix carcinoma (HeLa), and hepatocellular carcinoma (HepG2) cell lines were supplied by Vacsera (Giza, Egypt) and maintained at the Bioassay-Cell Culture Laboratory, National Research Centre, El-Bohouth St., Dokki, Cairo 12622, Egypt.

2.7.2. Cell Viability by MTT Assay

The samples were prepared by dissolving stock solution in DMSO to give operating concentrations of each sample range from 100 to 0.78 µg/mL, and the cells were incubated with these concentrations in triplicate (37 °C, 72 h) in a CO2 environment. Control wells were treated with the same amount of complete growth media only. For all treatments and untreated control groups, complete growth media without cells were added as a blank to reduce the background absorbance values. Separately, each experiment were conducted three times. MTT assay was performed by removing the medium quietly and adding MTT solution (10 μL) with a last concentration (5 mg/mL) per well then incubating (37 °C, 4 h) until the purple crystals were shaped. Then, the MTT solution was discarded from every well and DMSO (100 μL) was subjected to dissolve the crystals. The 96-well plate was shaken (15 min) using a microplate shaker until totally dissolved of the crystals. For each well, the absorbance value was assayed (595 nm wavelength) using a microplate multi-well reader [63]. The cell viability (CV) percentage after treatment with M. longipetala subsp. livida extracts were considered as follows: CV (%) = (absorbance of the treated cells − absorbance of blanks)/(absorbance of control cell − absorbance of blanks) × 100. The lethal concentration of the samples caused the death of 50% of cells (LC50) which was also calculated at 48 h. Doxorubicin, the anticancer drug, was used as a positive control.

3. Results and Discussion

3.1. UPLC-HRMS/MS Metabolites Profiling of the Extracts

The current study aimed to comparably chart the metabolic composition of different organs (i.e., flowers, leaves, and roots) of M. longipetala via UPLC-PDA-ESI-HRMS/MS analysis in both positive and negative ionization modes. The overlaid BPC (base peak chromatograms) of the three extracts exhibited some differences, especially at the Rt range of (10–25 min) in the positive ionization mode and (6–15 min) in the negative ionization mode (Supplementary Figure S1), suggesting that the three extracts could be of different biological relevance.

3.2. UPLC-HRMS/MS Metabolite Annotation Aided with Molecular Networking

The UPLC-HRMS/MS data were mined employing the GNPS platform, in which feature-based molecular networks (FBMNs) were generated to visually display the existing chemical space and the metabolites distribution in the different plant parts of M. longipetala.
Two FBMNs were laid out from the acquired MS/MS data for both ionization modes. The negative FBMN constituted 188 nodes grouped into 19 clusters (with a minimum of two connected nodes) and 130 singletons. The significant dereplicated sets of the negative FBMN were the secondary metabolites clusters: A (flavonoid glycosides), B (glucosinolates), C (hydroxycinnamic acid derivatives), D (hydroxybenzoic acid derivatives), and E (biflavones) (Figure 1). These metabolites are distributed in the flowers and leaves organs with their abundance in flowers, which could be responsible for the current cytotoxic assessment and guidance for further biological activities. Similarly, the positive FBMN constituted 257 nodes in 41 clusters and 104 discrete nodes, in which the classes of interest are cluster A (flavonoid glycosides and hydroxylated flavonoid aglycones) and B (methoxylated flavonoid aglycones); besides, cluster C (peptides) is presented as a primary metabolites class which characterized the roots organ and ionized in the positive ionization mode only (Figure 2). In general, nodes were portrayed as a pie chart to reflect the relative abundance of each ion in the three plant parts.
In total, 154 compounds were annotated belonging to different chemical classes (i.e., glucosinolates, phenolic acids, flavonoids, etc.). Almost all the annotated features are reported for the first time to exist in M. longipetala subsp. livida (Table 1). The classes and/or subclasses of compounds were preformed manually guided by the literature [2,28,33,80,81] and automatically through the ClassyFire webserver at (accessed on 27 June 2023) [82]. Following is a detailed discussion of the detected metabolites according to their chemical class.

3.2.1. Glucosinolates

Glucosinolates are one of the main bioactive metabolites of the Brassicaceae species and are thought to play a significant role in the health benefits of such species [2,28,80]. Their fragmentation behavior involves the cleavage of the sugar–sulfur bond, giving the fragment ion m/z 259 and the sulfur-aglycone showing fragment ions at m/z 195 and m/z 275. The intramolecular rearrangements of the attachment of aglycone and sulfate to the glucose moiety give the fragment ion m/z 241 after water cleavage from m/z 259 [28,80].
Eight of the nine identified glucosinolates are grouped in cluster B of the negative FBMN, occurring in the three plant parts (Figure 1). This includes isomers of glucoraphanin (7 and 14, m/z 434.0253 [M − H]), together with isomers of methylthio-butenyl-glucosinolate (11, 18, 23 and 35, m/z 418.0299 [M − H]), butyl glucosinolate (20, m/z 374.0582 [M − H]), and glucobrassicanapin (29, m/z 386.0582 [M − H]). Lastly, one glucosinolate was observed in the positive FBMN as a self-looped node and was identified as raphenin (10, m/z 176.0201 [M − H]+) (Table 1).

3.2.2. Phenolics

Besides the glucosinolates, members of the Brassicaceae are well recognized for their high content of phenolic metabolites, with qualitative and quantitative differences among species and varieties, within the same species, and plant parts [33]. In the present study, phenolic metabolites showed the highest accumulation in the flowers extract and the least in the roots. The major phenolic classes identified were phenolic acids and flavonoids.

Phenolic Acids and Derivatives

Detected phenolic acids included hydroxybenzoic acid and hydroxycinnamic acid (coumaric, ferulic, and sinapic acids) derivatives, which are widely distributed in numerous members of the Brassicaceae family, commonly as glycosylated descendants [2,33].
The negative FBMN delineated the abundance of glycosylated hydroxycinnamic acids in the flowers and grouped in cluster C (Figure 1), including isomers of coumaric acid-O-dihexoside (12 and 39, m/z 487.145 [M − H]), isomers of ferulic acid-O-dihexoside (26 and 43, m/z 517.155 [M − H]), sinapic acid-O-dihexoside (46, m/z 547.167 [M − H]), and later sinapic acid-O-hexoside (57, m/z 385.1141 [M − H]). Caffeic acid (93, m/z 179.0354 [M − H]) was also observed in the negative FBMN, but as a self-looped node and also accumulated in the flowers organ.
Similarly, glycosylated hydroxybenzoic acids were distributed in the three organs, and were observed in the negative FBMN (Figure 1). Hydroxybenzoic acid-O-hexoside (19; m/z 299.0770 [M − H]), and vanillic acid-O-hexoside (32; m/z 329.0853 [M − H]) were viewed as a cluster of two connected nodes (D). Other glycosides were observed as self-looped nodes and identified as dihydroxybenzoic acid-O-hexoside (25; m/z 315.0716 [M − H]) and dihydroxybenzoic acid-O-pentoside (37; m/z 285.0614). Lastly was dihydroxybenzoic acid (75; m/z 153.0192 [M − H]) which existed only in the roots extract. Additionally, one sulfo-hydroxybenzoic acid (36; m/z 246.9917 [M − H]) was noted as a self-looped node in negative FBMN, showing the characteristic loss of a sulfate group (−80 Da) and was assigned as vanillic acid-sulfate.
Other phenolic derivatives were also observed as self-looped nodes either in the positive or negative FBMN. They also distributed in the three extracts with richness in the flowers and tentatively identified as mono-hydroxy benzaldehyde isomers (54 and 61; m/z 137.0601 [M + H]+), trimethoxy benzaldehyde (69; m/z 197.0813 [M + H]+), trimethoxy benzaldehyde-O-hexoside (67; m/z 357.1559 [M − H]), sinapaldehyde (84; m/z 207.0665 [M − H]), coniferin (99; m/z 341.1242 [M − H]), and syringin (101; m/z 371.1350 [M − H]).


Flavonoids protect plants from various biotic and abiotic stresses by acting as natural antioxidants, unique UV filters, signal molecules, allelopathic compounds, and antimicrobial defensive compounds [81]. Additionally, their impressive biological effects have made them excellent candidates as nutraceutical supplements for human intake, disease prevention, and health promotion [2,81].
Throughout the current analysis, around 40% of the detected constituents are flavonoids (64 metabolites) (Table 1) delivered as cluster A and some as self-looped nodes in FBMN of the negative ionization mode (Figure 1) and clusters A and B in the positive one (Figure 2), being more abundant in the flowers.
The flavonoid-O-glycosides (56 compounds) were represented in cluster A in both FBMNs (Figure 1 and Figure 2), mainly as flavonol-O-glycosides, which have been previously reported in various species of Brassicaceae [2,3,4,28,31,39,45,46,48,65,83]. They were mostly distributed among the three investigated plant organs, with more abundance in the flowers. Only one flavone-O-glycoside was detected exclusively in the roots and was assigned as apigenin 7-O-glucoside (92, m/z 431.0981 [M − H]) based on the main fragment ion at m/z 269 which corresponds to apigenin aglycone and the loss of a glucose moiety [M − H–162].
The predominant annotated flavonol glycosides were mainly glycosides of kaempferol, isorhamnetin, and quercetin with little presence of rhamnocitrin, based on our former studies through acid hydrolysis and NMR data [8,46]. The quercetin glycosides in both FBMN were directly linked to their kaempferol correspondences by a difference of 16 Da (–O–), and with the isorhamnetin correspondences by a difference of 14 Da (–CH2). The direct attachment of the isorhamnetin glycosides to those of the kaempferol correspondents with a mass difference of 30 Da suggests possible OCH3 expansion.
The flavonol-O-glycosides showed the typical fragmentation patterns corresponding to the respective sugar moiety, such as deoxyhexose (−146 Da), hexose (−162 Da), and pentose (−132 Da). Mostly, the sugar moieties were tentatively assigned as rhamnose, glucose, and arabinose based on previous studies with acid hydrolysis and NMR data of the investigated species [8,46] and several members of the family Brassicaceae [3,28,46,65,83]. Some glycosides were acylated by acetic acid (−42 Da) and/or malonic acid (−86 Da).
Twelve flavonol mono-glycosides were observed and reported previously in some crucifers [46,83]. The 3-O-glucoside of quercetin (81, m/z 463.0878 [M − H]), kaempferol (88, m/z 447.0931 [M − H]), isorhamnetin (90, m/z 477.1035 [M − H]), and rhamnocitrin (111, m/z 461.1085 [M − H]), the 3-O-rhamnoside of kaempferol (102, m/z 431.0980 [M − H]), as well as the 3-O-arabinoside of quercetin (89, m/z 433.0755 [M − H]), which were tentatively identified according to Ablajan et al. [49], and Qin et al. [47]. In this case (3-O-glycosides), the intensity of the anion radical fragment [Agl–H–H] is higher than the anion one [Agl–H] and vis versus for 65 (kaempferol 7-O-rhamnoside) and 74 (isorhamnetin 7-O-rhamnoside).
Additionally, 12 flavonol di-O-glycoside structures were annotated and were grouped within the same cluster (Figure 1, cluster A). Compounds (40, 60, and 73) were assigned as kaempferol di-O-glycosides, showing the same molecular ion peak at m/z 609 [M − H] and common MS fragments at m/z 447 and 285. The MS fragmentation pattern of compound 40 is typical for kaempferol 3-O-sophroside. This compound revealed the deprotonated base peak at m/z 285 [M − H–324], a fragment ion at 429 [M − H–180], and a fragment ion at 447 [M − H–162], suggesting a sophoroside at the 3-O position [39]. Conversely, the absence of the fragment ion [M – H–180] in compound 73, indicates a kaempferol 3-O-gentobioside structure [39,49]. In contrast, the appearance of the fragment ion m/z 447 as the base peak confirmed the identification of compound 60 as kaempferol-3,7-di-O-glucoside [49]. Additionally, two O-rutinoside isomers of kaempferol (48, m/z 593.1511 [M − H], 82, m/z 593.1580 [M − H], 595.1665 [M + H]+) were confirmed. Sophoroside and rutinoside substitution have been observed in several cruciferous species as predominant disaccharide moieties [39].
Flavonol di-O-glycosides with sugar units at different hydroxyl positions of the aglycone nucleus provide two flavonol monoglycoside fragment ions with different intensities, where the higher fragment represents the 3-O-substitution while the lower one indicates the occupation of position 7 [39,47,49]. Consequently, compounds 62, 72, and 76 could be identified as 3-O-rhamnoside 7-O-arabinoside of quercetin (m/z 579.1349 [M − H]), kaempferol (m/z 563.1398 [M − H]), and isorhamnetin (m/z 593.1509 [M − H]), respectively. Likewise, the MS fragmentation of compounds 59 and 71 is typical for the 3-O-rhamnoside 7-O-glucoside of quercetin (m/z 609.1464 [M − H]) and isorhamnetin (m/z 623.1633 [M − H]), respectively.
Furthermore, different triglycosides of kaempferol (27, 42, 49, 50, 55, 64, 66, and 68), quercetin (51 and 58), and isorhamnetin (53) were also grouped in cluster A of both FBMNs (Figure 1 and Figure 2). The MS fragmentation of compound 27 (m/z 773.2147 [M + H]+) was characteristic of kaempferol-3-O-sophroside-7-O-glucoside [39]. Four kaempferol triglycosides isomers (50, 55, 64, and 66) showed a common molecular formula (C32H38O18), molecular ion peaks (m/z 709 [M − H]−- and 711 [M + H]+), and MS fragments at m/z (431 [M − H–296] and 433 [M + H–296]+), after the neural loss of a disaccharide residue (rhamnosyl arabinoside) and (285 [Agl − H], 287 [Agl + H]+). These compounds were directly connected with compound 72 (m/z 563.1398) in the negative MN with a mass difference 146 Da (rhamnosyl) (Figure 1), therefore, they could be annotated as kaempferol O-rhamnosyl arabinoside-O-rhamnoside isomers, one of them is recommended to be kaempferol 3-O-(2″-α-rhamnopyranosyl)-β-arabinopyranoside-7-O-α-rhamnopyranoside which was isolated before from the investigated plant by Marzouk et al. [8]. Likewise, compound (58, m/z 725.1937 [M − H] and 727.2094 [M + H]+) was linked with compound 62 (m/z 579. 1349 [M − H] and 581.1510 [M + H]+) in both FBMNs and could be identified as quercetin O-rhamnosyl arabinoside-O-rhamnoside. Also, the O-rhamnosyl arabinoside-O-glucoside derivatives of kaempferol (49, m/z 727.2088 [M + H]+), quercetin (51, m/z 741.1881 [M − H] and 743.2038 [M + H]+), and isorhamnetin (53, m/z 757.2199 [M + H]+) were identified. Based on previous studies, three kaempferol triglycosides 42 (m/z 757.2199 [M + H]+), 52 and 68 (m/z 739.2087 [M − H], 741.2243 [M + H]+) were confirmed as kaempferol-O-glucoside-O-rutinoside, kaempferol-O-rhamnoside-O-rutinoside, and kaempferol-O-rhamnosyl rutinoside, respectively [46,51].
Lastly, the highest glycosylation pattern was found in two tetra glycosides of kaempferol (33 and 47) which are concentrated in the flowers extract. Compound (33) appeared at m/z 917.2648 [M + FA − H], while 47 appeared at m/z 871.2510 [M − H], they have the same molecular formula (C38H48O23) and MS fragments (m/z 709 [M − H − 162 (glucose)]−, 563 [Agl − H + 278 (arabinosyl rhamnoside)], 447 [Agl − H + 162 (glucoside)], 431 [Agl − H + 146 (rhamnoside)], 285 [Agl − H]). Thus, they tentatively identified as kaempferol-O-arabinosyl-rhamnoside-O-rhamnoside-O-glucoside isomers, one of them could be identified as kaempferol 3-O-(2″-rhamnopyranosyl)-arabinopyranoside-7-O-rhamnopyranoside-4′-O-glucopyranoside which was isolated before from the current species [8].
Acylated flavonol-O-glycosides
A total of 16 acylated flavonol mono-glycosides were also observed in group A of the positive and negative FBMNs and connected with their O-glucoside analogs with MS differences of either 42 Da (acetyl) and/or 86 Da (malonyl). Whereas the acetylated and malonylated counterparts were correlated with each other with a 44 Da (CO2) difference (Figure 1 and Figure 2). The 3-O-malonyl glucoside of quercetin (85, m/z 549.0881 [M − H]), kaempferol (95, m/z 533.0936 [M − H]), isorhamnetin (96, m/z 565.1198 [M + H]+), and rhamnocitrin (113, m/z 549.1246 [M + H]+) were characterized by the neutral loss −86 Da (malonyl), then −162 Da (glucoside). Other mono-acylated flavonol glycosides were annotated as kaempferol 3-O-acetyl glucoside (105, m/z 489.1035 [M − H], m/z 491.1192 [M + H]+), two isomers of quercetin 3-O-acetyl glucoside (86 and 94, m/z 505.0979 [M − H], m/z 507.1142 [M + H]+), and three isomers of isorhamnetin 3-O-acetyl glucoside (97, 104, and 107, m/z 519.1143 [M − H], m/z 521.129 [M + H]+) (Supplementary Figure S2). Acylated monoglycoside derivatives of quercetin, kaempferol, and isorhamnetin have already been found in some cruciferous species [3,39], while reported for the first time from the genus Matthiola.
Similarly, the diacylated flavonol glycosides were represented as 3-O-diacetyl glucoside of kaempferol (109, m/z 531.1138 [M − H]), and isorhamnetin (110 and 115, m/z 561.12 [M − H]) (Supplementary Figure S2), connected with their 3-O-glucoside analogs with MS difference of 84 Da (2 acetyl residues) in negative FBMN (Figure 1). Four additional diacylated flavonol glycosides were 3-O-acetyl malonyl glucoside of quercetin (103, m/z 591.0995 [M − H], m/z 593.1148 [M + H]+), kaempferol (108 and 112, m/z 575.1044 [M − H], m/z 577.1201 [M + H]+), and isorhamnetin (114, m/z 607.1295 [M + H]+). They were linked with their 3-O-acetyl glucoside or 3-O-malonyl glucoside derivatives with a difference of 86 Da (malonyl) or 42 Da (acetyl), respectively, in either the negative or positive FBMNs (Figure 1 and Figure 2). For instance, compound 103 showed a deprotonated molecular ion peak at m/z 591.0995 [M − H] and produced fragment ions at m/z 547 [M − H − 44] after the neutral loss of CO2 then m/z 505 [M − H − 86], for malonyl elimination then m/z 301 [M − H − 86 − 42] and m/z 300 [M − H − H − 86 − 42], after the loss of the acetyl group (Supplementary Figure S3). Therefore, compound 103 could be identified as quercetin 3-O-X1 acetyl X2 malonyl glucoside. Similarly, compounds (108 and 112) were identified as kaempferol 3-O-X1 acetyl X2 malonyl glucoside and 114 as isorhamnetin 3-O-X1 acetyl X2 malonyl glucoside (Supplementary Figures S4 and S5). These four structural proposals were not found before in nature.
Flavonoid aglycones
Five polymethoxylated flavone-type aglycones were mainly observed in the positive ionization mode and represented as a cluster (B) of the FBMN (Figure 2). On the bases of GNPS libraries, they could be annotated as tangeretin (118), sinensetin (119), and 3,5,7,3′,4′pentatamethylflavone (124), all at m/z 373 [M + H]+, irigenin trimethyl ether (122) at m/z 403.1393 [M + H]+, and 3,5,6,7,3′,4′,5′heptamethylflavone (123). The polymethoxylated flavone aglycones were reported before from some species of the family Brassicaceae [27,33]. Likewise, one flavonol-type aglycone was linked in cluster (A) of the positive FBMN (Figure 2) and annotated as kaempferol (87, m/z 287.0505 [M + H]+) that was a predominant structure for all family members [39,46,47,83].
Additionally, two biflavone-structure were detected as a cluster (E) in a negative FBMN and elucidated as two isomers of methylamentoflavone (120 and 121, at m/z 551.09 [M − H]), confirmed by their fragmentation pattern and GNPS library (Figure 1). Rare biflavone derivatives were reported before for some species of Brassicaceae [48].

3.2.3. Iridoids and Diterpenes

Only one iridoid compound was found for the first time in the investigated species and concentrated in the flower parts. The iridoid is identified as loganic acid (30) and has a molecular ion peak m/z 375.1297 [M − H] and fragment ions at m/z 213 [M − H − 162]. Similarly, one diterpene structure was identified as miltirone (127, m/z 283.1698 [M − H]+) and produced fragment ions at m/z 265 ([M + H − H2O]+) and m/z 223 ([M + H − H2O − C3H6]+). Both compounds showed a wide range of activities including anti-cancer, anti-inflammatory, and antioxidant effects [36,71].

3.2.4. Coumarin

Coumarins are another vital class of secondary metabolites and were mainly observed in the positive ionization mode (Table 1). Hydroxy coumarin (38, m/z 163.0605 [M + H]+) revealed ions at m/z 147 [M + H–O]+, and 119 [M + H–CO2]+. Two isomers of dimethoxycoumarin (45, 56, m/z 207.065 [M + H]+) exhibited two characteristic fragments at m/z 193 [M + H−CH2]+, and 179 [M + H−2CH2]+, after loss of 14 Da. Additionally, compound 79 (m/z 455.1164 [M + H]+) was directly connected to 45 and 56, with a mass difference (248 Da). It produced fragment ions at 411, 369, and 207 after the loss of 42, 44, and then 162 Da, respectively, suggesting the presence of -O-malonyl glucoside dimethoxy coumarin.

3.2.5. Amino Acids, Organic Acids, and Derivatives

The annotation of the amino acids was derived from the abundant fragments of the protonated ions and their corresponding derivatives arising from either losing H2O (−18 Da) yielding their residue mass or the loss of (H2O + CO) (−46 Da) producing their immonium ions [84] leading to the detection of five amino acids including arginine (1), proline (2), leucine/isoleucine (17), phenylalanine (22), tryptophan (34), and three amino acids derivatives; methyl proline (5), dimethyl proline (6) and tryptophan N-glucoside (31), mainly distributed among the three plant organs. Similarly, five organic acids were detected as self-looped nodes either in the negative or positive FBMNs and identified as hydroxyl glutaric acid (8), malic acid (13), citraconic acid (methyl maleic acid) (15), dimethyl malate (38), and cinnamic acid (21) (Table 1).

3.2.6. Fatty Acids and Derivatives

Eight fatty acids and one fatty acid ester were detected, in the case of compound (116), the fragmentation patterns were matched with 9,12,13- trihydroxy-octadecadienoic acid, the molecular ion at m/z 327.2178 [M − H] and the fragments at m/z 229 and m/z 171 pointed to the positions of hydroxyl groups of fatty acids (that is, at 12 and/or 13, 9 and/or 10th carbon) but it was not easy to assign the functional groups and double bonds depending on our data. Therefore, this compound was identified as trihydroxy-octadecadienoic acid. Similarly, trihydroxy-octadecanoic acid (117) has a molecular ion at m/z 329.2328 [M − H] and the base peak at m/z 211.1342, other fragments were detected at m/z 311, 229,171 which confirmed the skeleton of trihydroxy-octadecanoic acid. Other fatty acids were detected in the negative ionization mode as lichesterylic acid (methyl-oxo-heptadecanoic acid) (134) at m/z 297.243 [M − H], 10-hydroxyoctadeca-12,15-dienoic acid (138) at m/z 295.2282 [M − H], and hydroxyl docosanoate (153) at m/z 355.3217 [M − H]. While, MS/MS fragmentation of compound (150) gave molecular ion at m/z 326.3796 [M − H]+ and characteristic fragment ions m/z 62.05 ([ethanolamine + H]+); m/z 308.2 ([M-H2O + H]+) and identified as N-oleoylethanolamine. In addition, two isomers of (17s)-hydroxy-docosa-pentaenoic acid were tentatively identified in all the examined M. longipetala plant parts (149; m/z 347.261 and 151; m/z 347.256 [M + H]+). Moreover, one fatty acid ester was assigned (152 at m/z 325.274 [M + H]+) as octadecenoic acid methyl ethyl ester.

3.2.7. Lipids

Five phospholipids were detected in M. longipetala extracts; three glycerophosphoinositol lipids were identified mainly in the leaves (negative ion mode) and identified as octadecatrienoyl-glycerophosphoinositol (125, m/z 593.2724 [M − H]), linoleoyl-glycerophosphoinositol (126, m/z 595.2885 [M − H]), and palmitoyl-glycerophosphoinositol (129, m/z 571.2884 [M − H]). In addition, two glycerophosphoglycerol lipids were identified in the root extract as hexadecenoyl-glycerophosphoglycerol at m/z 481.2568 [M − H] (139) and hexadecanoyl-glycerophosphoglycerol at m/z 483.2718 [M − H] (146).
Linoleoyl ethanolamide isomers (133 and 145; 322.2751 [M − H], 324.2901 [M + H]+) and palmitoyl ethanolamide (148; 300.2902 [M + H]+) are fatty amides that belong to the class of organic compounds known as N-acylethanolamines, in addition to dimethyl octadecenamide (154; 300.2902 [M + H]+). Lastly, one sulfoglycolipids was identified as hexadecanoyl glycerol-O-sulfo-rhamnoside at m/z 555.2844 [M − H] (136).

3.2.8. Peptides

Eleven polypeptides were detected in the positive ionization mode (cluster D), thoroughly characterized for the root organ (Table 1, Figure 2). They were tentatively identified according to MS differences and fragmentation patterns, then further sequenced corresponding to [72].

3.3. Cytotoxicity

As expected, flower extract that showed the highest abundance of secondary metabolites revealed a significant cell viability inhibition of HCT-116 and HeLa cell lines growth, with LC50 values (24.8 ± 0.45 and 18.1 ± 0.42 µg/mL), compared to those of Doxorubicin (37.6 ± 0.21 and 26.1 ± 0.27 µg/mL), respectively. Similarly, the leaf extract inhibited the propagation of the HeLa cell line with an LC50 value of 29.6 ± 0.35 µg/mL. The three methanolic extracts did not show any cytotoxic effect on the HepG2 cell line (Supplementary Table S1). These findings summarize the relationships between the cytotoxic assessment of the three examined organs and the concentration of secondary metabolites, particularly flavonoids. Consequently, the present data indicates that the flower organ is responsible for activities reported before for aerial parts on the same species [8].

4. Conclusions

The current study provided a holistic overview of the constitutive metabolome of M. longipetala, an under-explored member of Brassicaceae. UPLC-HRMS/MS coupled to FBMN, and in silico fragmentation trees allowed for the annotation of 154 metabolites, belonging to phenolic acids, glucosinolates, flavonoids, lipids, peptides, and others. Furthermore, four previously unknown compounds were tentatively assigned as O-acetyl O-malonyl glucosides of quercetin (103), kaempferol (108 and 112), and isorhamnetin (114) based on their fragmentation pattern and their connectivity to their known analogs. Yet their full structure elucidation requires other spectroscopic techniques (i.e., NMR) after their isolation. Lastly, cytotoxicity assessment of the plant parts revealed that the flowers are effective against HeLa and HCT-116 cell lines suggesting that they are a potential resource of bioactive cytotoxic compounds. Future in vivo research should focus on the chemical modification and targeted delivery of these promising bioactive molecules to maximize their anticancer potential.

Supplementary Materials

The following supporting information can be downloaded at:, Figure S1: The base peak chromatograms of Matthiola longipetala subsp. livida extracts: flowers (purple), leaves (green), and roots (yellow) in the negative ionization mode (A) and the positive ionization mode (B); Figure S2: Proposed fragmentation scheme and MS2 spectra (negative ionization mode) of A (isorhamnetin 3-O-glucoside, 90), B (isorhamnetin 3-O-acetyl glucoside 96 and 104), and C (isorhamnetin 3-O-diacetyl glucoside, 110 and 115); Figure S3: Proposed fragmentation scheme and MS2 spectrum (negative ionization mode) of quercetin 3-O-X1 acetyl -X2 malonyl glucoside, 103; Figure S4: Proposed fragmentation scheme and MS2 spectrum (negative ionization mode) of kaempferol 3-O-X1 acetyl -X2 malonyl glucoside, 108; Figure S5: Proposed fragmentation scheme and MS2 spectrum (positive ionization mode) of isorhamnetin 3-O-X1 acetyl -X2 malonyl glucoside, 114. Table S1: LC50 values (µg/mL) of the cell viability inhibition of Matthiola longipetala subsp. livida extracts on different cell lines.

Author Contributions

M.M.M.; conceptualization, supervision, resources, validation, formal analysis, compounds identification, data curation, writing—original draft, writing—review editing. M.M.F. and M.O.A.E.S.; conceptualization, investigation, data curation, writing—original draft, writing—review and editing. N.M.H.; conceptualization, methodology, formal analysis, software, writing—review editing. S.A.K., S.R.H. and N.A.M.S.; conceptualization, validation, review and editing, supervision, project administration. All authors have read and agreed to the published version of the manuscript.


The chemical extraction and the cytotoxic approach were funded by the National Research Centre, Cairo, Egypt (grant number: M120201).

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

The designed MNs and parameters can be retrieved via the following links: accessed on 28 December 2019 for the positive network and accessed on 28 December 2019 for the negative network.


The authors thank Hamada Saad, of the Department of Pharmaceutical Biology, the Pharmaceutical Institute, the Eberhard Karls University of Tübingen, Germany, for the UPLC-LC-HRMS/MS measurements.

Conflicts of Interest

The authors declare no conflict of interest.


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Figure 1. FBMN created using MS/MS data of Matthiola longipetala subsp. livida extracts (negative ionization mode): flowers (purple), leaves (green), and roots (yellow) extracts. Cluster A (flavonoid glucosides), Cluster B (glucosinolates), Cluster C (hydroxycinnamic acids), Cluster D (hydroxybenzoic acids), and Cluster E (biflavones). *; the substitution position may vary.
Figure 1. FBMN created using MS/MS data of Matthiola longipetala subsp. livida extracts (negative ionization mode): flowers (purple), leaves (green), and roots (yellow) extracts. Cluster A (flavonoid glucosides), Cluster B (glucosinolates), Cluster C (hydroxycinnamic acids), Cluster D (hydroxybenzoic acids), and Cluster E (biflavones). *; the substitution position may vary.
Metabolites 13 00909 g001
Figure 2. FBMN created using MS/MS data of Matthiola longipetala subsp. livida extracts (positive ionization mode): flowers (purple), leaves (green), and roots (yellow) extracts. Cluster A (flavonoid glycosides and hydroxylated flavonoid aglycones), Cluster B (methoxylated flavonoid aglycones), and Cluster C (peptides). *; the substitution position may vary. The red circles explained the enlarged clusters.
Figure 2. FBMN created using MS/MS data of Matthiola longipetala subsp. livida extracts (positive ionization mode): flowers (purple), leaves (green), and roots (yellow) extracts. Cluster A (flavonoid glycosides and hydroxylated flavonoid aglycones), Cluster B (methoxylated flavonoid aglycones), and Cluster C (peptides). *; the substitution position may vary. The red circles explained the enlarged clusters.
Metabolites 13 00909 g002
Table 1. Metabolites identified in the aqueous methanol extracts of flowers, leaves, and roots from Matthiola longipetala subsp. livida via UPLC-HRMS-MS in negative and positive ionization modes.
Table 1. Metabolites identified in the aqueous methanol extracts of flowers, leaves, and roots from Matthiola longipetala subsp. livida via UPLC-HRMS-MS in negative and positive ionization modes.
No.Chemical Class
RT(M − H)(M + H)+MS2RootLeafFlowerTentatively
(Error in ppm)
2.21-175.1193-158.0928, 128.0200,
116.0708, 86.9928
++++ArginineC6H14N4O2 (1.9)[22]
2.41-116.0713-70.0660++++ProlineC5H9NO2 (5.3)[22]
3Saccharides2.45341.1090-179.0565, 161.0469,
149.0471, 119.0348,
-++ DihexosideC12H22O11 (0.4)[23]
4Alkaloids and
derivatives (alkaloids)
2.54-138.0505-122.0648, 110.0594,
-+-Trigonelline *C7H7NO2 (−2.7)[24]
5Amino acids
and derivatives
++++Methyl proline *C6H11NO2 (1.0)[22]
6Amino acids
and derivatives
2.59-144.1019-130.0502, 104.0294,
++++Dimethyl prolineC7H13NO2 (0.3)[22]
2.60434.0253-419.0020, 274.9899,
259.0128, 240.9670,
195.0335, 168.9510,
129.0253, 96.9602,
-++++GlucorapheninC12H21NO10S3 (0.4)[25]
8Organic acids
(hydroxy acids)
2.70147.0298-129.0193, 101.0244,
-t++++Hydroxyglutaric acidC5H8O5 (0.6)[23]
2.72-873.2667-595.1675, 449.1086,
rhamnosyl glucoside
C38H48O23 (0.2)[8]
2.83-176.0201-149.0595, 117.0335,
-++++Raphenin *C6H9NOS2 (−1.6)[26]
2.93418.0299-259.0127, 224.9726,
176.0208, 96.9601,
-++++-Methylthiobutenyl- glucosinolateC12H21NO9S3 (0.8)[27]
12Phenolic acids
and derivatives
acid glycosides)
3.02487.1458-163.0422, 145.0295---+Coumaric acid-O-
C21H28O13 (0.4)[28]
13Organic acids
(hydroxy acids)
3.60133.0143-115.0039, 72.9935-t++++Malic acidC4H6O5 (0.4)[29]
3.67434.0254-419.0020, 274.9899, 259.0129, 240.9671,
195.0333, 168.9509,
129.0251, 96.9602,
C12H21NO10S3 (0.2)[30]
15Organic acids
(dicarboxylic acids)
3.75-131.0342-116.9329, 108.9868,
+++Citraconic acid
(methyl maleic acid)
C5H6O4 (−2.3)[31]
16Organic acids
(carboxylic acids)
C6H11NO2 (1.9)[31]
17Amino acids3.79-132.1019-86.0965,
+++Leucine/isoleucineC6H13NO2 (0.1)[22]
3.92418.0299-274.9898, 259.0127, 195.0335, 96.9602,
-+--Methylthiobutenyl-glucosinolate isomerC12H21NO9S3 (0.2)[27]
19Phenolic acids
and derivatives
acid glucoside)
4.21299.0770-137.0244, 93.0345-++++Hydroxy benzoic
C13H16O8 (0.8)[31]
195.0338, 96.9601,
C11H21NO9S2 (0.9)[27]
21Organic acids
(cinnamic acids)
4.36-149.0600 105.0444, 104.0543,
C9H8O2 (−1.8)[29]
147.0457, 103.0558,
120.080, 103.0543,
+++Phenylalanine *C9H11NO2 (0.3)[22]
4.53418.0299-274.9805, 259.0129,
224.9700, 195.0330,
176.0207, 96.9602,
---+Methylthio-butenyl-glucosinolate isomerC12H21NO9S3 (0.1)[27]
24Organic acids
(carboxylic acids)
4.54218.1036220.1184146.0823, 88.0406,
184.0974, 172.1327, 158.0603,
142.0860, 124.0760,
++++Pantothenic acid
(vitamin B5)
C9H17NO5 (0.7)[32]
25Phenolic acids
and derivatives
acid glycosides)
4.70315.0716-153.0186, 152.0113, 109.0297, 108.0225-+++Dihydroxybenzoic acid-O-hexosideC13H16O9 (0.8)[17]
26Phenolic acids and
(hydroxycinnamic acid glycosides)
4.81517.1558-397.1158, 193.0508,
175.0401, 119.0345
-t-+Ferulic acid-O-dihexoside *C22H30O14 (0.0)[33]
5.01-773.2147-611.1624, 449.1084,
t++++Km 3-O-sophroside-
C33H40O21 (1.5)[34]
5.02-151.0757-136.0605, 119.0496, 91.0543,
C9H10O2 (−2.1)[35]
5.11386.0582-274.9892, 259.0134, 195.0335, 96.9602,
--++++GlucobrassicanapinC12H21NO9S2 (0.5)[28]
5.13375.1297-167.0709, 152.077-t++++Loganic acidC16H24O10 (0.1)[36]
31Amino acids
and derivatives
5.20-367.1504-349.1397, 332.1128, 303.1349, 276.1241, 258.1131, 229.0976, 202.064, 188.0713,
C17H22N2O7 (0.8)[37]
32Phenolic acids
and derivatives
acid glycosides)
-209.0445, 167.0350, 119.0342, 89.0245-t++++Vanillic acid-
C14H18O9 (0.2)[17]
5.50917.2648 a-871.2510, 709.1991, 563.1405, 431.0940, 285.0369---+Km -O-arabinosyl rhamnoside-O-
glucoside b
C38H48O23 (0.5)[8]
5.54203.0824205.0975142.0664, 116.0503, 74.0248188.0711, 170.0606,
159.0916, 146.0602, 132.0810, 118.0653
+++Tryptophan *C11H12N2O2 (−0.2)[22]
5.65418.0299420.0457274.9805, 259.0129,
224.9700, 195.0330,
176.0207, 96.9602,
178.0360, 130.0324, 85.0282++++Methylthio-butenyl-glucosinolate isomerC12H21NO9S3 (0.6)[27]
36Phenolic acids
and derivatives
acid derivative)
5.81246.9919-167.0350, 152.0116, 153.0452, 108.0219-+++Vanillic
C8H8O7S (0.5)
37Phenolic acids
and derivatives
acid glycosides)
5.81285.0614-153.019, 152.0112, 109.0292, 108.0220-+++Dihydroxybenzoic acid-O-pentosideC12H14O8 (0.5)[38]
and derivatives
5.91-163.0605-147.0446, 131.0497, 119.0494, 103.0544,
t++++HydroxycoumarinC9H6O3 (−2.0)[31]
39Phenolic acids
and derivatives
acid glycosides)
5.94487.1452-367.1031, 163.0397,
-t++++Coumaric acid-
C21H28O13 (0.5)[28]
6.10609.1459-447.0927, 429.0825, 285.0404-t++++Km 3-O-
sophoroside *
C27H30O16 (0.3)[39]
41Phenolic acids
and derivatives
6.11395.0649-241.0023, 152.9863, 96.9602-++++tDihydroxyphenylethanol-O-sulfoglucosideC14H20O11S (0.9)[40]
6.14-757.2199-449.1087, 287.0557t++++Km-O-rutinoside-
C33H40O20 (1.1)[41]
43Phenolic acids
and derivatives
acid glycosides)
-t++++Ferulic acid-O-
dihexoside isomer *
C22H30O14 (0.4)[33]
6.25-163.0601-131.0496, 119.0494, 103.0544, 91.0544,
t++++Hydroxylhexanedioic acid * (Hydroxyadipic acid)C6H10O5 (−2.7)[42]
and derivatives
6.31-207.065-193.0544, 179.0701, 147.0436, 119.0494, 91.0546t++++DimethoxycoumarinC11H10O4 (2.1)[43]
46Phenolic acids
and derivatives
acid glycosides)
6.31547.167-427.1245, 223.0618, 205.051, 190.0268, 179.0564-t++++Sinapic acid-O-
dihexoside *
C23H32O15 (4.5)[44]
6.39871.2510873.2667709.1976, 563.1404, 447.0923, 431.0975,
711.1985, 595.1675, 449.1086, 433.1137, 287.0556-++++Km 3-O-(2″-rhamnosyl)-arab-inoside-7-O-rhamnoside-4′-O-β-glucoside bC38H48O23 (0.7)[8]
6.39593.1511595.1665285.0397, 284.0323449.1088, 287.0559, 229.0868, 207.0658t++++Km 3-O-
C27H30O15 (0.4)[31]
6.40-727.2088-449.1093, 287.0559-++++Km O-arabinosyl rhamnoside-O-
C32H38O19 (1.1)[31]
6.44-711.2146-433.1137, 287.0557t++++Km-O-arabinosyl rhamnoside-O-
C32H38O18 (1.3)[8]
743.2038609.1461, 579.1348, 463.0872, 447.0924, 301.0351611.1608, 465.1035, 303.0504t++++Qn-O-arabinosyl rhamnoside-O-
C32H38O20 (1.9)[45]
6.74739.2087741.2247593.1511, 447.0923, 431.0952, 285.0397, 284.0323465.1035, 433.1137,
t++++Km 3-O-rhamnoside 7-O-rutinoside *C33H40O19 (0.5)[46]
6.83-757.2199-479.1195, 463.1243, 317.0661-++++Is O-arabinosyl
C33H40O20 (1.8)[31]
54Phenolic derivatives (benzoyl derivatives)6.88-137.0600-123.0394, 122.0365, 107.0500, 95.0415,
t++++MethoxybenzaldehydeC8H8O2 (2.5)[47]
6.94709.1973-563.1407, 431.0960,
285.0397, 284.0324
---+Km-O-rhamnosyl arabinoside-O-
C32H38O18 (0.3)[8]
and derivatives
6.98-207.0657-193.0544, 179.0710, 147.0447, 119.0494, 91.0543,
C11H10O4 (2.0)[43]
57Phenolic acids
and derivatives
acid glycosides)
6.98385.1141-223.0617, 205.0505,
190.0271, 179.0715,
-t++++Sinapic acid-O-
hexoside *
C17H22O10 (0.1)[17]
7.22725.1937727.2094579.1357, 447.0898, 446.0850, 301.035449.1086, 303.0507tt+Qn-O-rhamnosyl- arabinoside-O-
C32H38O19 (0.7)[46]
7.29609.1464611.1615463.0878, 447.0852,
301.0352, 285.0399
303.0505t++++Qn 3-O-rhamnoside 7-O-glucosideC27H30O16 (0.5)[47,48]
7.41609.1462-447.0927, 285.0404-t++++Km 3,7 di-O-glucoside *C27H30O16 (0.3)[39,49]
7.55-137.0601-123.0394, 122.0365,
107.0510, 95.0508,
t++++Methoxybenzaldehyde isomerC8H8O2 (−1.9)[50]
7.65579.1349581.1510447.0906, 446.0854, 433.0779, 301.0347303.0506tt+++Qn 3-O-rhamnoside 7-O-arabinosideC26H28O15 (1.3)[51]
7.72-565.1552-287.0555t++++Km 3-O-arabinoside-7-O rhamnosideC26H28O14 (1.4)[48]
7.73709.1991-563.1407, 431.0960,
---+Km O-rhamnosyl
433.1133285.0397, 284.0324287.0557-++++Km 7-O-
rhamnoside *
C21H20O10 (0.8)[31]
431.0986, 285.0400
433.1138, 287.0556t++++Km O-arabinosyl rhamnoside-O-
rhamnoside b
C32H38O18 (1.3)[8]
7.86357.1559-195.1032, 180.0784,
C17H26O8 (0.9)[50]
7.91739.2094741.2243285.0402287.0557t++++Km 3-O-(di-O-
glucoside *
C33H40O19 (0.5)[51]
7.93-197.0813-137.0597, 105.0338, 79.0541++++Trimethoxy
C10H12O4 (−2.6)[50]
70Fatty acid
(fatty acyl
8.00 -387.2039, 225.1504,
161.0458, 113.0258,
-t++++Hydroxyjasmonic acid-O-hexoside
(tuberonic acid-
C18H28 O9 (2.0)[52]
8.04623.1633625.1774477.1031, 461.1071, 315.0510317.0662--+Is 3-O-rhamnoside 7-O-glucosideC28H32O16 (1.5)[46]
--t+Km 3-O-rhamnoside 7-O-arabinosideC26H28O14 (0.5)[48]
8.19609.1446-447.0918, 285.0396, 284.0318--++++Km 3-O-
C27H30O16 (0.8)[39]
8.39461.1069463.1240315.0509, 314.0429317.0661++++Is 7-O-
C22H22O11 (1.8)[47]
8.41153.0192-109.0296, 81.0350-t++++Dihydroxybenzoic acidC7H6O4 (0.9)[53]
8.43593.1509595.1663461.1069, 447.0928, 315.0509317.0661t++++Is 3-O-rhamnoside 7-O-arabinosideC27H30O15 (0.5)[28]
8.45609.1468611.1614301.0346303.0511, 287.0552,
229.0500, 129.0554,
t++++Qn 3-O-rutinoside
(rutin) *
C27H30O16 (0.3)[46]
78Benzoic acids
and derivatives
8.61223.0246-179.0354, 135.0461,
C10H8O6 (0.9)[23]
and derivatives
8.63-455.1164-411.1268, 369.1162,
207.0938, 179.0701,
147.0494, 79.0283,
-++++Dimethoxycoumarin-O-malonyl glucosideC20H22O12 (4.4)[43]
8.92355.1401-221.0442, 161.0453,
139.0222, 119.0345,
101.0245, 89.0247,
---+Hydroxy phenyl
pentanoic acid-O-
C17H24O8 (0.6)[54]
9.02463.0878-301.0277, 300.0276-t++++Qn 3-O-
glucoside *
C21H20O12 (0.2)[34]
9.08593.1580595.1665285.0396, 284.0325287.0552t++++++Km-O-
rutinoside *
C27H30O15 (0.6)[55]
9.26623.1622625.1770315.0510317.0661t+++++Is 3-O-
rutinoside *
C28H32O16 (0.7)[51]
9.4207.0665-192.0429, 179.0536-t++++SinapaldehydeC11H12O4 (0.7)[17]
9.45549.0881551.1040505.0988, 463.0882, 301.0331, 300.0275, 271.0242303.0507t++++Qn 3-O-
malonylglucoside *
C24H22O15 (1.8)[56]
9.54505.0979-463.0886, 301.0332,
300.0272, 271.0247,
-t++++Qn 3-O-acetyl-
glucoside *
C23H22O13 (1.7)[57]
9.59-287.0505-257.0450, 229.0114,
149.0140, 97.0287
t++++Km *,bC15H10O6 (0.2)[57]
9.60447.0931449.1083327.0528, 285.0387,
284.0325, 255.0299,
287.0555t++++Km 3-O-glucoside
(astragalin) *
C21H20O11 (0.8)[47]
9.71433.0755-301.0332, 300.0276-t++++Qn 3-O-
C20H18O11 (0.4)[58]
9.83477.1035479.1195315.0481, 314.0430,
299.0199, 285.0397,
271.0249, 243.0299
317.0664t-+Is 3-O-
glucoside *
C22H22O12 (0.8)[49,58]
and derivatives
9.92223.0251-179.0351, 153.0194,
benzoic acid
C10H8O6 (0.6)[23]
10.07431.0981433.1128269.0447271.060+++ttApigenin 7-O-
glucoside *
C21H20O10 (0.3)[52]
93Phenolic acids
and derivatives
10.11179.0354-135.0461, 109.0297-t++++Caffeic
acid *
C9H8O4 (0.4)[52]
10.15505.0979507.1142463.0886, 301.0332, 300.0275303.0507t++++Qn 3-O-acetyl
C23H22O13 (1.7)[56]
10.25533.0936535.1091285.0385, 284.0323287.0557t++++Km 3-O-
C24H22O14 (1.6)[59,60]
10.46-565.1198-317.0662t+-Is 3-O-
C25H24O15 (1.8)[61]
10.47519.1143-477.0989, 315.0502, 314.0429-t++Is 3-O-acetyl
C24H24O13 (2.1)[62]
10.51505.0979507.1142463.0886, 301.0338, 300.0275303.0505t++++Qn 3-O-acetyl
C23H22O13 (1.7)[56]
derivatives (phenylpropanoid
10.58341.1242-161.0428, 133.0660,
C16H22O8 (0.2)[63]
10.65447.0925-315.0477, 314.0430, 299.0209-t++++Is 3-O-
C21H20O11 (2.2)[46]
10.91371.1350-209.0441, 163.0767, 148.0531-t++++Sinapoyl alcohol-O-glucoside
C17H24O9 (−0.6)[64]
10.99431.0980-285.0400, 284.0323, 155.0303, 227.0347--++++Km 3-O-
(afzelin) *
C21H19O10 (0.9)[65]
11.01591.0995593.1148547.1082, 505.0982, 301.0333, 300.0277303.0506t++++Qn 3-O-X1
C26H24O16 (0.3)
11.11519.1121521.1297477.1016, 315.0428, 314.0430, 299.0192317.0664, 287.0547t++++Is 3-O-acetyl
C24H24O13 (1.5)[62]
11.23489.1035491.1192285.0385, 284.0327287.0555t++++Km 3-O-acetyl
C23H22O12 (0.7)[56]
106Saccharides11.33405.09-241.0022, 152.9869, 96.9604-+++Thioglucose-penta
C16H22O10S (1.4)
11.44 521.1296 317.0661, 127.0391t+++++Is 3-O-acetyl
glucoside isomer
C24H25O13 (0.8)[62]
12.01575.1044577.1191531.1144, 489.1029, 285.0385, 284.0321287.0555, 255.0441, 127.0391t+++++Km 3-O-X1 acetyl-X2 malonyl glucosideC26H24O15 (0.5)
12.02531.1138-489.1031, 285.0385, 284.325, 255.0295-t++++Km 3-O-diacetyl
C25H24O13 (0.7)[62]
12.23561.1236-519.1152, 477.1016
315.0428, 314.0427, 299.0198
-t++++Is 3-O-diacetyl
C26H26O14 (0.7)[62]
12.31461.1085-299.0554, 298.0485, 283.0250-++++Rh 3-O-
glucoside b
C22H22O11 (1.9)[8]
12.68-577.1201-449.0908, 287.0555t++++Km 3-O-X1 acetyl-X2 -malonyl glucoside
C26H24O15 (−2.2)
12.86547.1095549.1246505.0963, 299.0239, 298.0280, 271.0250, 163.0770301.0713, 231.0520, 159.0292,
+++++Rh 3-O-malonoyl
C25H24O14 (−1.5)[61]
12.88-607.1295-317.0662, 302.0427,
287.0546, 255.0512,
231.0500, 127.0392,
t++++Is 3-O-X1 acetyl X2
C27H26O16 (0.3)
12.90561.1223-519.1147, 477.0989, 315.0502, 314.0430, 299.0205---+Is 3-O-diacetyl
glucoside (isomer II)
C26H26O14 (0.5)[62]
13.70327.2178-291.1951, 229.1452, 211.1384, 171.1026, 85.0297-++++Trihydroxy-
acid *
C18H32O5 (0.8)[66]
14.64329.2328-311.2220, 229.1442, 211.1342, 171.1025-+++++Trihydroxy-
C18H36O5 (0.4)[67]
15.87-373.1285358.1051, 343.0819, 329.1048, 315.0864, 229.0576-t++++Pentamethoxyflavone
(tangeretin) *
C20H20O7 (0.9)[68]
359.1180, 343.0821,
329.1024, 312.1006,
297.0771, 283.0981,
-t++++Pentamethoxyflavone isomer
(sinensetin) *
C20H20O7 (1.2)[68]
17.08551.098-519.0691, 457.0573,
431.0760, 389.0667
methyl ether
C31H20O10 (0.0)[69]
18.05551.099-519.0727, 457.0560, 431.0769, 389.0660-t++++Amentoflavone
methyl ether isomer
C31H20O10 (0.1)[69]
18.47-403.1393373.0923, 359.1129,
343.0824, 329.1024,
-t++++Hexamethoxyflavone (Irigenin trimethyl ether) *C21H22O8 (1.3)[68]
19.29-433.1492419.1299, 418.1265, 403.1029, 385.0914-t++++Heptamethoxyflavone
(Nobiletin) *
C22H24O9 (0.8)[68]
19.88-373.1286358.1057, 343.0822,
325.0715, 312.0995,
271.0609, 211.0249,
-t++++Pentamethoxyflavone *C20H20O7 (1.1)[68]
19.92593.2724595.2888413.2085, 315.0483,
277.2171, 241.0119,
335.2586, 261.2222, 243.2124, 184.0707,
155.0107, 81.0697
+++++Octadecatrienoyl-glycero-phosphoinositolC27H47O12P (0.4)[70]
21.71595.2885-415.2244, 315.0475,
279.2329, 241.0116,
C27H49O12P (0.2)[70]
127Diterpenes21.82-283.1698-265.1586, 223.1485,
197.1330, 183.1205
++++Miltirone *C19H22O2 (−1.0)[71]
22.41-298.346-281.0533, 245.1075, 227.0968, 74.0965t++++N-hydroxyoleylamide *C18H35NO2 (1.6)
22.88571.2884-391.2254, 315.0487,
255.2329, 241.0119,
glycero-phosphoinositol *
C25H49O12P (−1.7)[70]
130Peptides23.12-643.2734-586.2621, 583.2526, 529.2143, 523.2311,
381.2094, 311.1647,
293.1540, 265.1591,
247.1489, 205.1966,
182.1016, 147.0811,
133.1029, 89.0603
C30H38N6O10 (−1.8)[72]
23.94-657.2866-597.2677, 537.2455,
507.2379, 343.132, 311.1642, 247.1480, 205.1966, 181.1016
166.0754, 147.0811
C31H40N6O10 (−1.4)[72]
-631.2520, 571.2318, 541.2204, 495.1999, 453.1890, 393.1681, 353.1750, 311.1641, 293.1539, 265.1591, 247.1485, 223.1123, 133.0858, 91.0540+--Serinyl-
C34H38N6O10 (−1.5)[72]
133Fatty amides24.43-322.2751-304.2645, 135.0326, 107.0862, 95.0860+++t+α-Linolenoyl ethanolamide *C20H35NO2 (0.5)[73]
24.52297.243 279.2334, 183.0120
-+++t+Methyl-oxo-heptadecanoic acid (lichesterylic acid) *C18H34O3 (0.6)
135Peptides24.61-685.29-625.2624, 565.2402,
353.1726, 293.1542,
247.1489, 181.1005,
182.0998, 147.0851,
119.0874, 106.0743
+--Tryptophyl-glutamyl-tyrosyl-serinyl-threonineC32H40N6O11 (−1.8)[72]
24.79555.2844-299.0446, 255.2331, 206.9963, 80.9655-++++++Hexadecanoyl
C25H48O11S (0.2)[74]
-369.1955, 351.1849,
333.1749, 313.2087,
277.1588, 182.1230,
166.1178, 106.4462,
+--Tyrosyl-glycyl-glycyl phenylalanyl-
C30H38N6O9 (−1.6)[72]
138Fatty acids25.05295.2282-279.2331-+++ttHydroxyoctadecadienoic acid *C18H32O3 (1.0)
25.16481.2568-253.2174, 245.0430, 227.0324, 152.9959-t++++Hexadecenoyl
sn-glycerol *
C22H43O9P (0.6)[70]
140Peptides25.36-699.2995-639.2786, 579.2571,
519.2348, 495.1999,
453.1890, 393.1681,
353.1750, 311.1641
293.1539, 265.1591, 247.1485, 223.1123,
133.0858, 91.0540
C34H46N6O8S (−1.6)[72]
141Peptides25.72-675.2624-618.2624, 455.2040, 421.1996, 295.1699,
277.1592, 267.1749,
249.1642, 205.1903, 107.0875, 91.0543
+--Glycyl-Serinyl-tyrosyl-tryptophyl-tyrosineC34H38N6O9 (−1.3)[72]
142Peptides25.75-593.2754-397.2016, 355.1903,
295.1695, 277.1592,
267.1747, 249.1640,
+--Acetyl-tryptophyl-methyl-alanyl-aspartyl-phenylalaninamideC30H36N6O7 (−1.8)[72]
143Peptides25.82-641.2942-581.2734, 521.2517,
461.2302, 313.1501,
295.1700, 277.1592,
249.1640, 173.0965,
106.0743, 91.0543
C31H40N6O9 (−1.6)[72]
144Peptides26.03-633.2679-576.2636, 523.2266,
437.1942, 377.1728,
267.1752, 253.1588,
239.1456, 107.0864,
alanyl- alanyl
C32H36N6O8 (−1.8)[72]
26.26-324.29306.2793, 263.2363
245.2256, 147.1161,
109.1010, 95.0857,
ethanolamide *
C20H37NO2 (0.2)[73]
26.60483.2718 227.0324,
C22H45O9P (0.2)[70]
147Peptides27.16-617.2724-557.2543, 497.298, 421.1988, 361.1785, 321.2406, 297.1849, 279.1747, 251.1804,
209.1325, 91.0538
+--Tryptophyl-glutamyl-prolyl-tryptophanC18H37NO2 (0.5)[72]
27.70-300.2902283.2642, 242.2482, 109.1012, 95.0857
ethanolamide *
C18H37NO2 (0.5)[75]
28.07-347.2610-275.1620, 235.1318, 195.1004, 179.9946, 95.0865tt+++Hydroxy-
docosa-pentaenoic acid *
C22H34O3 (0.5)[76]
28.34-326.3796-308.2959, 107.0847, 95.0857,
+++t+N-Oleoylethanolamine *C20H39NO2 (0.2)[77]
docosa-pentaenoic acid isomer *
C22H34O3 (0.6)[76]
30.21-325.274-265.2527, 247.2421,
135.1169, 121.1013,
109.1013, 95.0856,
acid methyl
ethyl ester
C20H36O3 (1.2)[78]
32.10355.3217-337.3118, 309.3161, 297.1527-+++ttHydroxyl
C22H44O3 (0.2)[79]
33.72-310.3111293.2853, 275.2741, 97.1015,
-+++Dimethyl-octadecenamideC20H39NO (−2.1)[77]
a; [M + FA − H], b; compound reported before from M. longipetala subsp. livida, *; tentatively identified compounds reported by GNPS libraries, +++; very strong, ++; strong, +, present, t; trace, -; absent, Km; kaempferol, Qn; quercetin, Is; isorhamnetin, Rh; rhamnocitrin.
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MDPI and ACS Style

Marzouk, M.M.; Hegazi, N.M.; El Shabrawy, M.O.A.; Farid, M.M.; Kawashty, S.A.; Hussein, S.R.; Saleh, N.A.M. Discriminative Metabolomics Analysis and Cytotoxic Evaluation of Flowers, Leaves, and Roots Extracts of Matthiola longipetala subsp. livida. Metabolites 2023, 13, 909.

AMA Style

Marzouk MM, Hegazi NM, El Shabrawy MOA, Farid MM, Kawashty SA, Hussein SR, Saleh NAM. Discriminative Metabolomics Analysis and Cytotoxic Evaluation of Flowers, Leaves, and Roots Extracts of Matthiola longipetala subsp. livida. Metabolites. 2023; 13(8):909.

Chicago/Turabian Style

Marzouk, Mona M., Nesrine M. Hegazi, Mona O. A. El Shabrawy, Mai M. Farid, Salwa A. Kawashty, Sameh R. Hussein, and Nabiel A. M. Saleh. 2023. "Discriminative Metabolomics Analysis and Cytotoxic Evaluation of Flowers, Leaves, and Roots Extracts of Matthiola longipetala subsp. livida" Metabolites 13, no. 8: 909.

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