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Article

Chemical Profiling and Differential Constituents Analysis of Honghema and Its Easily Confusable Species Driven by High-Resolution Mass Spectrometry and Pattern Recognition

by
Congying Huang
1,2,†,
Yute Zhong
1,†,
Han Li
1,2,
Dan Wu
1,
Taiping Li
3,
Weijie Li
1,
Siying Chen
4,5,
Zipeng Gong
4,5,*,
Haiyu Xu
3,* and
Ping Wang
1,2,*
1
State Key Laboratory for Quality Ensurance and Sustainable Use of Dao-di Herbs, Institute of Chinese Materia Medica China Academy of Chinese Medical Sciences, Beijing 100700, China
2
Graduate School of China Academy of Chinese Meical Sciences, Suzhou 215105, China
3
Liaoning University of Traditional Chinese Medicine, Shenyang 117004, China
4
State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), School of Pharmacy, Guizhou Medical University, Guian New Area 561113, China
5
Guizhou Key Laboratory of Modern Traditional Chinese Medicine Creation, Guiyang 550004, China
*
Authors to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Molecules 2026, 31(15), 2614; https://doi.org/10.3390/molecules31152614
Submission received: 13 June 2026 / Revised: 20 July 2026 / Accepted: 24 July 2026 / Published: 27 July 2026
(This article belongs to the Section Analytical Chemistry)
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Versions Notes

Abstract

Background: Honghema is a traditional Chinese medicinal material and is also widely used by ethnic minority communities in Guizhou Province, where it is commonly known as “Reib ndad gunb” and “Uab Detdend”. The botanical origins were the whole plants of Laportea bulbifera (Siebold & Zucc.) Wedd. (L. bulbifera) and Girardinia diversifolia (Link) Friis (G. diversifolia). Due to morphological similarities, Urtica mairei H. Lév. (U. mairei) was often mixed as easily confusable species in actual market circulation. However, systematic research regarding the differences in chemical composition between the two botanical origins, as well as between them and their easily confusable species remain limited. This study aimed to comprehensively characterise the chemical constituents of L. bulbifera, G. diversifolia, and U. mairei, and to identify significantly differential chemical constituents for their discrimination. Methods: Data acquisition was performed using ultra-performance liquid chromatography–mass spectrometry (UPLC-MS). Multivariate statistical analyses combined with reference standard comparison were performed to investigate the differences in chemical profiles among L. bulbifera, G. diversifolia and U. mairei, identify the key differential constituents leading to the differences, and clarify their relative abundance information. Results: A total of 133, 77, and 59 chemical constituents were identified from L. bulbifera, G. diversifolia, and U. mairei, respectively. These compounds comprised flavonoids, organic acids, carbohydrates, organonitrogen compounds, terpenoids, coumarins, lipids, steroids, and other types of compounds. Flavonoids constituted the highest proportion of the compounds in L. bulbifera, whereas organic acids were the most abundant in G. diversifolia and U. mairei. Through multivariate statistical analysis, 32 inter-group differential components between L. bulbifera and G. diversifolia, 27 between L. bulbifera and U. mairei, and 13 between G. diversifolia and U. mairei were screened and identified. The core components contributing to these differences included Baimaside, Roxburic acid, 1-Galloyl-glucose, Protocatechuic acid 3-glucoside, and Schaftoside. Venn diagram analysis revealed 20 characteristic differential constituents of L. bulbifera, mainly represented by flavonoids; 6 characteristic differential constituents of G. diversifolia, primarily comprising terpenoids and organic acids; and 4 characteristic differential constituents of U. mairei, mainly represented by carbohydrates. Conclusion: Significant differences were observed among the chemical profiles of the three plant species. The method established in this study can effectively identify the chemical compositions of Honghema and its easily confusable species, revealing the key components responsible for the variations in their chemical profiles. This study provides a basis for elucidating the material foundation of Honghema and offers an effective analytical approach and valuable reference data for distinguishing Honghema from its easily confusable species.

1. Introduction

Honghema is a commonly used plant medicine in China, and a traditional medicine utilised by ethnic minorities in Guizhou Province. In 2022, it was included in the Catalogue of Miao and other ethnic minority medicinal materials in Guizhou Province [1]. The Quality Standards for Chinese Medicinal Materials and Ethnic Medicinal Materials of Guizhou Province (2019 edition) [2] stipulated that the botanical origins of Honghema were the whole plants of L. bulbifera and G. diversifolia. Honghema is often used alone or in combination with other herbal medicines for the treatment of rheumatoid arthritis (RA) and other diseases, demonstrating considerable medicinal value. Several compound preparations containing Honghema as the principal medicinal ingredient have been included in the Chinese national drug standards, including Runzao Zhiyang Capsules, Compound Shangfuning Ointment, Liuwei Shangfuning Tincture, and Tongluo Guzhining Ointment. Pharmacological studies have demonstrated that Honghema could effectively alleviate pain and inhibit excessive lymphocyte proliferation [3,4,5], reduce joint swelling and bone destruction [6,7], and induce apoptosis of pathological synovial cells by activating the mitochondrial apoptotic pathway [8], exhibiting significant anti-inflammatory and analgesic properties [9,10,11]. Previous chemical investigations of Honghema have mainly focused on L. bulbifera, which contains abundant flavonoids, phenolic acids, steroids, terpenoids, and others. Multiple constituents have been identified from different parts of this plant by researchers. Feng et al. studied the stems, leaves and roots of L. bulbifera and found phenolic and fatty acid components [12]. Lu et al. isolated 17 chemical constituents from the stems and leaves of L. bulbifera [13]. Tang et al. analyzed the extract of L. bulbifera and identified 6 flavonoids and 8 other components [14]. Furthermore, Shrestha et al. conducted a phytochemical analysis on the extract of G. diversifolia [15], identifying steroids, fatty acids, and phenolics. Zhang et al. investigated the aerial parts of G. diversifolia and isolated five chemical constituents [16]. Liu et al. extracted and isolated 20 chemical components from G. diversifolia [17], while Liu et al. isolated and identified three compounds [18]. Although these studies have made significant contributions to elucidating the chemical profile of Honghema, systematic analyses of its constituents remain insufficient, and the types, contents, and distribution characteristics of its specific marker compounds have yet to be fully clarified. The accurate identification of botanical origins and the consistency of medicinal material quality directly affect clinical efficacy and medication safety. Therefore, further chemical investigations of Honghema are required to expand the discovery of novel chemical constituents, identify differential chemical markers, which will subsequently facilitate a comprehensive understanding of the material basis underlying its medicinal effects.
On the other hand, during practical circulation and application, Honghema is commonly subjected to preliminary processing, such as coarse cutting before medicinal use. This processing results in the near-complete loss of its macroscopic morphological characteristics, thereby exacerbating the difficulty of species identification and leading to the occurrence of substitution or admixture with easily confusable species. For instance, U. mairei, a species belonging to the same family, is frequently used as an easily confusable species of Honghema due to its similar morphological appearance and has become one of the typical confused species encountered during commercial circulation. Regarding the current status of phytochemical research, existing reports predominantly focus on L. bulbifera, whereas only a limited number of studies have involved G. diversifolia. Furthermore, no studies have concurrently examined Honghema alongside easily confusable species. Although L. bulbifera and G. diversifolia are both recognised as botanical origins of Honghema, whether their chemical compositions are similar and whether their core pharmacologically active constituents are consistent remain unclear. Meanwhile, it is yet to be determined whether significant chemical variations exist between Honghema and its easily confusable species, and whether they can be effectively differentiated via chemical methodologies. The current absence of systematic, parallel comparative studies significantly increases the difficulty of quality control (QC) for Honghema. Therefore, analysing the differences between Honghema and its easily confusable species from a phytochemical perspective, as well as establishing a rapid and reliable method for the discovery of chemical markers and the systematic identification and discrimination of these species, constitutes a crucial approach to resolving this issue.
Honghema possesses significant medicinal value, but reliable identification methods are required for its QC. In this study, a systematic chemical analysis was conducted on the two botanical origins of Honghema (L. bulbifera and G. diversifolia) and its easily confusable species (U. mairei), using ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC-Q-TOF-MS/MS) coupled with pattern recognition methods. First, the chemical compositions of the three plant species were comprehensively characterised to elucidate the chemical profiles. Subsequently, comparative analyses were performed to investigate the differences in chemical compositions between L. bulbifera and G. diversifolia, L. bulbifera and U. mairei, as well as G. diversifolia and U. mairei. The relative abundance variations of key constituents were evaluated, and potential chemical marker compounds were screened for species discrimination. The findings of this study provide a scientific basis for elucidating the material basis of Honghema and distinguishing it from commonly confused species. Furthermore, the results offer valuable data references for improving the quality standards and QC strategies of Honghema.

2. Results

2.1. Identification of Chemical Constituents in L. bulbifera, G. diversifolia, and U. mairei

The reliability of the established UPLC-Q-TOF-MS/MS method was first evaluated using QC samples. The QC samples were prepared by mixing equal volumes of all sample extracts and were repeatedly injected at regular intervals throughout the analytical sequence. The reproducibility of the method was assessed by monitoring the stability of instrumental responses. The representative base peak intensity (BPI) chromatograms of the three plant species were shown in Figure 1A,B. Distinct differences were observed in the retention time distribution ranges and response intensities of the major chromatographic peaks among the three species, indicating that L. bulbifera, G. diversifolia, and U. mairei exhibited distinguishable overall chemical profiles. Based on accurate relative molecular masses, MS/MS fragmentation patterns of compounds, previously reported chemical constituents of three species, and an in-house database, the chemical constituents of the three species were systematically identified. The MS/MS spectra of reference standards were presented in Supplementary Figure S1.
A total of 133 chemical constituents were characterised from Laportea bulbifera. According to their structural classifications, these constituents included 40 flavonoids, 28 organic acids, 24 carbohydrates, 13 organonitrogen compounds, 10 terpenoids, 5 coumarins, 4 lipids, 1 steroid, and 8 other constituents (Table 1; Figure 1C,F and Figure 2A,B). Flavonoids represented the predominant constituent class in L. bulbifera and exhibited high chromatographic responses. Organic acids and carbohydrates also showed relatively strong chromatographic responses and constituted important components of its chemical profile. A total of 77 chemical constituents were characterised from G. diversifolia, comprising 19 organic acids, 9 terpenoids, 9 organonitrogen compounds, 8 carbohydrates, 8 lipids, 8 flavonoids, 3 steroids, 1 coumarin, and 12 other constituents (Table 2; Figure 1D,G and Figure 2C,D). Organic acids, terpenoids and organonitrogen compounds exhibited high chromatographic responses in the chromatograms. Compared with L. bulbifera, flavonoids in G. diversifolia accounted for a smaller proportion of the total constituents. Lipids, carbohydrates and steroids constituted important classes within its chemical composition. A total of 59 chemical constituents were characterised from U. mairei, encompassing 14 organic acids, 11 carbohydrates, 7 flavonoids, 7 lipids, 7 organonitrogen compounds, 3 coumarins, 2 steroids, 1 terpenoid, and 7 other constituents (Table 3; Figure 1E,H and Figure 2E,F). Organic acids and carbohydrates represented the major constituent classes of U. mairei, and both the chromatographic response and the number of detected flavonoids were lower than those observed in L. bulbifera and G. diversifolia.
The identification of the chemical constituents in L. bulbifera, G. diversifolia, and U. mairei demonstrated that significant differences exist in the chemical composition characteristics and principal component categories among the three species.

2.1.1. Characterization and Identification of Flavonoids and Their Derivatives

Identification of flavonoids and their derivatives was mainly based on characteristic fragmentation patterns of glycosidic bonds and the Retro-Diels-Alder (RDA) cleavage of aglycones. Taking the representative compound Baimaside as an example, in the ESI− mode, the deprotonated molecular ion [M−H]− was observed at m/z 625.14 (C27H29O17−, mass error 0.57 ppm). MS/MS analysis of this ion revealed that it first lost a hexosyl moiety, producing the fragment ion at m/z 463.09 [M−H−C6H10O5]−, which subsequently lost one molecule of water to yield m/z 445.08 [M−H−C6H10O5−H2O]−. In addition, characteristic ions related to the aglycone structure and its secondary fragmentation (m/z 193.01, 151.00, 107.01) were also observed in the spectrum. Therefore, this compound was identified as Baimaside (Figure 3A).
Hyperoside was detected in positive ion mode with its quasi-molecular ion [M+H]+ at m/z 465.10. In its MS/MS spectrum, this ion lost a galactosyl moiety to produce the aglycone ion at m/z 303.05 [M+H−C6H10O5]+. The aglycone ion further underwent RDA cleavage, generating a characteristic fragment ion at m/z 153.02, which is consistent with the fragmentation behavior of Hyperoside. Thus, the compound was identified as Hyperoside.
In addition, for flavanols such as Catechin, the deprotonated molecular ion [M−H]− was detected at m/z 289.07 in negative ion mode. MS/MS analysis revealed that this ion primarily underwent retro-aldol cleavage of the C-ring, leading to carbon skeleton fragmentation and the loss of large neutral fragments, directly generating a series of characteristic fragment ions representing the A-, B-, and C-ring structures, including m/z 165.02, m/z 151.04, m/z 137.02, and m/z 125.02, as well as a secondary fragment ion at m/z 109.03 (Figure 3B).
For flavonoid aglycones such as Quercetin, the protonated molecular ion [M+H]+ was observed at m/z 303.05. MS/MS analysis showed that this ion underwent retro-Diels-Alder (RDA) cleavage to produce a characteristic fragment ion at m/z 153.02, which is consistent with the mass spectral features of Quercetin.
Based on the above comprehensive analysis, a variety of flavonoids and their derivatives were successfully identified, including flavonols and their glycosides, flavones, flavanols, and dimers.

2.1.2. Characterization and Identification of Organic Acids and Their Derivatives

This class of constituents mainly includes caffeoylquinic acids and their isomers, as well as simple hydroxycinnamic acids. Their mass spectrometric fragmentation behavior exhibits notable regularity: in negative ion mode, the [M−H]− ions commonly undergo decarboxylation, dehydration, and cleavage of glycosidic bonds.
Caffeoylquinic acid compounds were the main organic acids identified in this study. Taking Chlorogenic acid as an example, its deprotonated molecular ion [M−H]− was observed at m/z 353.09 (C16H17O9−, mass error −1.87 ppm). In the MS/MS spectrum, two characteristic fragmentation pathways were observed. In the quinic acid skeleton pathway, the ester bond underwent cleavage with the loss of a caffeoyl moiety, generating the characteristic quinic acid fragment ion at m/z 191.06 [M−H−C9H6O3]−, which further dehydrated to produce the secondary fragment ion at m/z 173.05. In the caffeic acid skeleton pathway, cleavage of the ester bond in another direction afforded the caffeic acid fragment ion at m/z 179.04 [M−H−C7H10O5]−, which subsequently decarboxylated to yield the secondary fragment ion at m/z 135.05. These specific fragment ions and their corresponding loss patterns further confirmed the structural assignment of Chlorogenic acid (Figure 3C).
Additionally, the identification of simple hydroxycinnamic acids was mainly based on their decarboxylation and side-chain cleavage. Taking caffeic acid as an example, its [M−H]− ion was observed at m/z 179.03 (C9H7O4−, mass error −0.06 ppm). In its MS/MS spectrum, this ion readily underwent decarboxylation to produce the fragment ion at m/z 135.05 [M−H−CO2]−. In addition, the ion at m/z 109.03 was observed, which is presumed to arise from further cleavage of the side chain (Figure 3D).
Ferulic acid is a methoxy derivative of caffeic acid. Its [M−H]− ion was observed at m/z 193.05 (C10H9O4−, mass error −1.74 ppm). MS/MS analysis revealed that its fragmentation pathway exhibited characteristic features of the methoxy group. On the one hand, the precursor ion lost a methyl radical to generate m/z 178.03 [M−H−CH3]−; on the other hand, it underwent decarboxylation to produce m/z 149.06 [M−H−CO2]−, which further lost a methyl radical to yield m/z 134.04. In addition, a low-mass ion at m/z 71.01, arising from side-chain cleavage, was observed in the spectrum, corresponding to a stable oxygen-containing fragment formed after the breakdown of the side-chain carbon skeleton. The complete fragmentation sequence—from demethylation and decarboxylation of the precursor ion to the full cleavage of the side chain—constitutes key mass spectrometric evidence for the identification of Ferulic acid (Figure 3E).
In addition, other organic acid constituents such as Benzoic acid, Citric acid, Vanillic acid and Sinapic Acid were also identified.

2.1.3. Characterization and Identification of Carbohydrates and Their Derivatives

In this analysis, multiple carbohydrate components were identified, including monosaccharides, oligosaccharides, phenylethanoid glycosides, and other types. The mass spectrometric fragmentation of these components exhibits distinctive characteristics. In negative ion mode, cleavage of glycosidic bonds frequently occurs, with the loss of one or more glycosyl moieties to generate the corresponding aglycone or secondary glycoside ions, which may be accompanied by processes such as dehydration and ring-opening rearrangement.
The fragmentation of glycosidic ester components reflects the loss of both glycosyl and acyl moieties. Taking 1-O-caffeoylglucose as an example, its deprotonated molecular ion [M−H]− was observed at m/z 341.09 (C15H17O9−, mass error −0.60 ppm). The MS/MS spectrum exhibited multiple fragmentation pathways. On one hand, cleavage of the acyl-oxygen bond occurred, with the loss of a dehydrated glucose moiety, generating the caffeate anion at m/z 179.04 [M−H−C6H10O5]−, which serves as key evidence for ester bond cleavage. The caffeate anion further lost one molecule of water to yield m/z 161.02 [M−H−C6H10O5−H2O]−, or underwent characteristic decarboxylation to produce m/z 135.05 [M−H−C6H10O5−CO2]−. On the other hand, the precursor ion lost two molecules of water to generate m/z 305.07 [M−H−2H2O]−. These fragment ions constitute important evidence for the identification of 1-O-caffeoylglucose (Figure 3F).
Among the glycoside components, the fragmentation behavior of 2-O-alpha-D-glucopyranosyl-L-ascorbic acid simultaneously reflects glycosidic bond cleavage and characteristic fragmentation of the ascorbic acid aglycone. In negative ion mode, its deprotonated molecular ion [M−H]− was detected at m/z 337.08 (C12H18O11−, mass error 1.71 ppm). MS/MS analysis revealed multiple fragmentation pathways. On one hand, the precursor ion underwent glycosidic bond cleavage with the loss of one glucose residue, generating the ascorbic acid aglycone anion at m/z 175.02, which is a characteristic fragmentation of glycosides. This aglycone fragment further lost one molecule of water to produce m/z 157.01, or underwent side-chain cleavage to yield m/z 99.01. On the other hand, the precursor ion could undergo direct bond cleavage to generate the fragment at m/z 277.06. These fragmentation ions collectively constitute important evidence for the identification of 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (Figure 3G).
During mass spectrometric fragmentation of carbohydrate components, glycosidic bond cleavage is the most common feature. Many types of glycosides preferentially lose glycosyl moieties to generate aglycone or secondary glycoside ions, and the mass of the lost glycosyl group can serve as a basis for inferring the type of sugar residue.

2.1.4. Characterization and Identification of Terpenoids and Their Derivatives

Terpenoids and their derivatives are structurally diverse, and their mass spectrometric fragmentation patterns mainly include: triterpenoids readily lose carboxyl groups and water molecules, generating characteristic skeletal fragment ions; iridoids and their glycosides commonly undergo glycosidic bond cleavage, ring opening, and consecutive losses of small neutral fragments. The following is an analysis of the identification and fragmentation pathway of 7,8-dehydropenstemoside identified based on the accurate mass and MS/MS information provided by high-resolution mass spectrometry.
7,8-Dehydropenstemoside is an iridoid glycoside. Its deprotonated molecular ion [M−H]− (C17H24O11−, mass error −1.22 ppm) was detected in negative ion mode. This ion underwent glycosidic bond cleavage with the loss of a dehydrated hexosyl moiety to generate the aglycone ion at m/z 241.07. Subsequently, the aglycone ion further dehydrated to produce the fragment at m/z 223.06. Alternatively, the precursor ion could also undergo side-chain cleavage or ring-opening rearrangement to yield m/z 165.06. This mass spectrometric behavior—stepwise loss of the sugar moiety followed by fragmentation of the aglycone skeleton—provides important evidence for the identification of iridoid glycosides (Figure 3H).

2.1.5. Characterization and Identification of Coumarins and Their Derivatives

The mass spectrometric fragmentation of this class of constituents exhibits distinctive characteristics, commonly involving the opening of the lactone ring, the loss of small neutral molecules such as CO, and the cleavage of substituents such as methoxy and glycosyl groups. Taking 7-methoxy-2H-chromen-2-one as an example, its protonated molecular ion [M+H]+ was detected in positive ion mode at m/z 177.05 (C10H9O3+, mass error 0.80 ppm), along with five major characteristic fragments: m/z 163.04, 159.04, 145.03, 133.03, and 121.03. Among these, m/z 163.04 may arise from the loss of a methylene group from the precursor ion; m/z 159.04 may be formed by dehydration of the precursor ion; m/z 145.03 may originate from a rearrangement elimination involving the loss of CH4O, suggesting the presence of a methoxy substituent; m/z 133.03 and m/z 121.03 can be inferred as small fragment ions formed by the sequential loss of small neutral fragments after the opening of the lactone ring of the parent nucleus (Figure 3I).

2.1.6. Characterization and Identification of Organonitrogen Compounds and Their Derivatives

In this analysis, nitrogen-containing compounds were identified, including nucleosides, amides, vitamins, amino acids, and sphingosine derivatives. The mass spectrometric fragmentation behaviors of this class of constituents are diverse: in positive ion mode ([M+H]+), nitrogen-containing compounds often undergo characteristic cleavages involving the nitrogen atom, such as the loss of ammonia (NH3, 17 Da) or substituents on the nitrogen-containing heterocyclic ring; nucleosides readily undergo glycosidic bond cleavage to generate characteristic base ions, while amides frequently produce characteristic fragment clusters in the low-mass region.
9-ribofuranosyladenine is a representative purine nucleoside compound. In positive ion mode, its protonated molecular ion [M+H]+ was detected at m/z 268.10 (C10H14N5O4+, mass error 0.90 ppm). Its MS/MS spectrum revealed two major fragmentation pathways: first, cleavage of the glycosidic bond with the loss of a ribose residue, generating the purine base ion at m/z 136.06, which is a key ion for the identification of adenosine and its derivatives. This adenine ion could further lose one molecule of ammonia to produce the fragment at m/z 119.04. This sequential fragmentation process of “loss of sugar—loss of ammonia” (Figure 3J) is consistent with the common fragmentation behavior of purine nucleoside compounds in positive ion mode, providing evidence for the structural confirmation of 9-ribofuranosyladenine.
The mass spectral fragmentation of phenylalanine conforms to the typical cleavage patterns of amino acids. In positive ion mode, its protonated molecular ion [M+H]+ was detected at m/z 166.09 (C9H12NO2+, mass error −0.92 ppm). Analysis of its MS/MS spectrum revealed that the precursor ion first lost one molecule of ammonia to generate the imine ion at m/z 149.06 [M+H−NH3]+. This is a characteristic fragmentation reaction of α-amino acids. This fragment ion could undergo further complex cleavages: m/z 149.06 could subsequently lose one molecule of water to yield m/z 131.05 [M+H−NH3−H2O]+. Alternatively, via a rearrangement reaction, the precursor ion directly lost formic acid to give m/z 120.08 [M+H−HCOOH]+, which could be assigned to the benzylmethylamine cation. These fragments further dissociated, ultimately leading to the highly characteristic benzyl ion at m/z 91.05 and even smaller fragment ions at m/z 77.04. These fragments serve as strong evidence for the identification of amino acids containing a benzene ring (Figure 3K).

2.1.7. Characterization and Identification of Lipids and Their Derivatives

The lipid components identified in this study mainly include free fatty acids, oxygenated fatty acids, and simple glycerides. Fatty acids readily undergo α-cleavage, dehydration, and chain cleavage induced at carbon–carbon double bonds, generating characteristic fragment ions. These fragments are crucial for inferring the carbon chain length, positions of double bonds, and oxygen-containing functional groups.
Taking 1-Monolinolein as an example, its protonated molecular ion [M+H]+ was detected in positive ion mode at m/z 355.28 (C21H39O4+, mass error 0.04 ppm). MS/MS analysis revealed multiple fragmentation pathways. First, the precursor ion lost one molecule of water to generate the fragment ion at m/z 337.27 [M+H−H2O]+, which is a typical dehydration feature of glycerolipids. Subsequently, cleavage of the ester bond led to the loss of the glycerol skeleton as a neutral molecule, producing the fragment at m/z 263.24. This fragment corresponds to protonated linoleic acid and is a key ion for confirming the composition of the acyl chain. In addition, the characteristic fragment ion at m/z 81.07, arising from double-bond-induced cleavage of the linoleic acid long chain, was observed in the spectrum, further supporting the structural features of the polyunsaturated fatty acid chain (Figure 3L).

2.1.8. Characterization and Identification of Steroids and Their Derivatives

The mass spectrometric fragmentation behavior of steroidal compounds exhibits distinctive characteristics, mainly involving cleavage of the steroid nucleus and loss of the side chain. 7-Keto-β-sitosterol is a major oxidized sterol identified in this study. In positive ion mode, its protonated molecular ion [M+H]+ was detected at m/z 429.37 (C29H49O2+, mass error 1.68 ppm). MS/MS analysis of this precursor ion showed that it could lose one molecule of water molecule to generate the fragment ion at m/z 411.36 [M+H−H2O]+, which is a common primary cleavage of oxygenated sterols. An important characteristic fragment ion was observed at m/z 313.22 [M+H−C8H20]+, arising from cleavage of the sterol side chain; this fragmentation provides key information regarding the side chain length and linkage mode. The ion at m/z 109.06 originates from cleavage of the steroidal nucleus. These fragments confirm the basic skeleton of this compound, which consists of a steroid nucleus with an attached side chain (Figure 3M).

2.1.9. Characterization and Identification of Other Constituents

In this compositional analysis, components that could not be classified into the above major categories were also identified, mainly including aldehydes, ketones, cyclitols, and a few compounds with special structures. The mass spectrometric fragmentation behaviors of these components vary, but they still follow the characteristic fragmentation rules of organic compound functional groups, such as dehydration of alcohols, α-cleavage of ketones, and benzylic cleavage.

2.2. Multivariate Statistical Analysis of L. bulbifera, G. diversifolia, and U. mairei

To elucidate the overall differences in chemical composition among L. bulbifera, G. diversifolia and U. mairei, and to identify potential discriminatory markers, multivariate statistical analysis was performed based on the peak area datasets of chemical constituents in each sample obtained from UPLC-Q-TOF-MS/MS (Figure 1A,B).

2.2.1. Principal Component Analysis

To observe the overall clustering trends of the samples and avoid potential bias caused by artificial grouping, an unsupervised PCA was initially performed on the raw data of all samples, including the QC samples. The results demonstrated that all QC samples clustered tightly on the score plot, verifying the instrument stability and data reliability throughout the entire analytical sequence. All test samples separated into three relatively independent clusters according to their species, without any overlap (Figure 4A,B). These findings clearly indicate that differences exist in the overall chemical profiles of the three species, which provided a basis for the subsequent pairwise comparisons among the three groups and the screening of specific discriminating components.

2.2.2. Analysis of Compositional Differences Between L. bulbifera and G. diversifolia

L. bulbifera and G. diversifolia are the two botanical origins of Honghema stipulated in the Quality Standards for Chinese Medicinal Materials and Ethnic Medicinal Materials of Guizhou Province (2019 edition) [2]. To identify the differential components responsible for the separation of L. bulbifera and G. diversifolia, an OPLS-DA model was established. The OPLS-DA score plots demonstrated that samples from the L. bulbifera and G. diversifolia groups separated into two distinct clusters (Figure 4C–F), whereas no overlap was observed between the two groups, indicating that L. bulbifera and G. diversifolia possessed stable and significant differences in their chemical compositions.
To screen the differential constituents contributing significantly to the discrimination between the two groups, differential ions were initially selected according to the criteria of VIP values > 1.0 and p < 0.05. The MS/MS fragment ions of the selected differential features were subsequently matched and verified using UNIFI 1.9.4 software. The structures of the compounds were further confirmed by comparison with reference standards and previously reported fragmentation patterns. In total, 32 significantly differential components were identified (Table 4; Figure 2G,H and Figure 5(A1–A32)). Regarding the distribution of component types, 22 differential components exhibited higher relative abundances in L. bulbifera, with flavonoids being the most prevalent, which is consistent with the characteristics of L. bulbifera as a flavonoid-rich species. Conversely, 10 differential components exhibited higher relative abundances in G. diversifolia, consisting primarily of organic acids and terpenoids, which is consistent with the high-abundance dominant component profile of G. diversifolia. These differential constituents provided a chemical basis for the discrimination between L. bulbifera and G. diversifolia.

2.2.3. Analysis of Compositional Differences Between L. bulbifera and U. mairei

U. mairei is an easily confusable species of Honghema during commercial circulation. To establish a chemical basis for the discrimination between L. bulbifera and U. mairei, the OPLS-DA model was applied to explore the differential chemical features between L. bulbifera and U. mairei. The OPLS-DA score plots demonstrated that L. bulbifera and U. mairei could be effectively distinguished (Figure 4G–J), indicating that significant differences exist in their chemical compositions.
To identify the differential variables that contributed significantly to the separation of the L. bulbifera and U. mairei, the VIP values generated from the OPLS-DA model were integrated with the statistical analysis of peak responses between groups using the same screening criteria of VIP > 1.0 and p < 0.05. A preliminary set of differential ions was thereby obtained. Following the matching of MS/MS fragments and structural confirmation, a total of 27 differential components were identified (Table 5; Figure 2I,J and Figure 6(A1–A27)). Overall, 24 differential constituents exhibited higher relative abundances in L. bulbifera, mainly consisting of flavonoids and carbohydrates. These constituents showed extremely low responses or were not detected in U. mairei. In contrast, the three constituents with higher relative abundances in U. mairei were mainly carbohydrates, displaying distinct differences from the predominant constituent groups of L. bulbifera. These differential constituents provided a chemical basis for the discrimination between L. bulbifera and U. mairei.

2.2.4. Analysis of Compositional Differences Between G. diversifolia and U. mairei

The previous PCA results revealed an evident separation trend between G. diversifolia and U. mairei. To further clarify the differences in their chemical compositions, an OPLS-DA model was established. The OPLS-DA score plots showed that the samples from the G. diversifolia and U. mairei were completely separated without overlapping observations (Figure 4K–N), indicating that there were stable and identifiable differences in the chemical compositions between G. diversifolia, a botanical origin of Honghema, and its easily confusable species, U. mairei.
Following the consistent screening criteria for differential ions (VIP > 1.0, p < 0.05), and incorporating MS/MS fragment analysis and structural identification, 13 differential components were identified between G. diversifolia and U. mairei (Table 6; Figure 2K,L and Figure 7(A1–A13)). Regarding the distribution patterns of these constituents, 8 differential constituents exhibited higher relative abundances in G. diversifolia, mainly comprising terpenoids and organic acids. In contrast, 5 differential constituents showed higher relative abundances in U. mairei, predominantly belonging to carbohydrates. These differential constituents covered the characteristic predominant constituent groups of the two plant species and provided evidence for the chemical discrimination of G. diversifolia from its commonly confused species U. mairei.

2.2.5. Screening of Characteristic Constituents in the Three Species Based on Venn Diagram Analysis

To further screen highly specific and stable characteristic differential constituents that could simultaneously discriminate each species from the other two related plants, the differential constituents obtained from the three pairwise comparisons, including 32 constituents from L. bulbifera vs. G. diversifolia, 27 constituents from L. bulbifera vs. U. mairei, and 13 constituents from G. diversifolia vs. U. mairei, were subjected to Venn diagram analysis to screen characteristic constituents of the three plant species.
Twenty components, including Baimaside, were identified as common differential constituents in L. bulbifera compared with G. diversifolia and U. mairei (Figure 7(A14)). These components exhibited relatively high responses in L. bulbifera and were primarily flavonoids, suggesting them as potential characteristic markers for L. bulbifera. Six constituents, including Esculentoside B and Roxburic acid, were identified as common differential constituents of G. diversifolia compared with both L. bulbifera and U. mairei (Figure 7(A15)). These constituents showed relatively higher responses in G. diversifolia and were mainly represented by terpenoids, indicating their potential as candidate characteristic differential constituents of G. diversifolia. Furthermore, four constituents, including Isoeucommin A and 3-Hexenyl-beta-glucopyranoside, were identified as common differential constituents of U. mairei compared with both L. bulbifera and G. diversifolia (Figure 7(A16)). These constituents exhibited relatively higher responses in U. mairei and were mainly classified as carbohydrates, suggesting their potential as candidate characteristic differential constituents of U. mairei.
Through Venn diagram analysis, characteristic constituents of the three plant species were further screened from the pairwise differential constituents. These markers exhibit higher species specificity compared with those derived from single pairwise comparisons and provide a valuable reference for the chemical discrimination of these three plant species.

3. Discussion

In this study, ultra-high-performance liquid chromatography coupled with high-resolution mass spectrometry combined with multivariate statistical analysis was employed to systematically characterise the chemical compositions of the two botanical origins of Honghema and its easily confusable species U. mairei. The results demonstrated that the three plant species differed not only in the number of detected chemical constituents but also in their overall chemical profiles. The differential constituents screened in this study could serve as potential chemical markers for the discrimination of Honghema and its easily confusable species, providing valuable reference data for improving the quality standards of Honghema.
Regarding chemical identification, the three species exhibited markedly different compositional characteristics and significantly different predominant constituent classes. Flavonoids were the most prevalent constituents in L. bulbifera, accounting for 30.08%, with flavonoid glycosides such as Baimaside and Quercetin-3-O-beta-D-glucose-7-O-beta-D-gentiobioside serving as characteristic compounds. These, alongside organic acids and carbohydrates, accounted for nearly 70% of the total constituents, representing the major chemical composition of L. bulbifera. G. diversifolia showed a distinct profile where organic acids were the predominant group (24.68%), followed by a notable abundance of terpenoids and organonitrogen compounds, while the proportion of flavonoids was significantly lower than in L. bulbifera. U. mairei exhibited a unique composition dominated by organic acids (23.73%) and carbohydrates (18.64%), with relatively low abundances of terpenoids and flavonoids.
Unsupervised PCA revealed that samples from the three species clustered into completely independent groups, indicating significant differences in their secondary metabolite compositions. This approach overcomes the limitations of traditional morphology-based identification, which relies on intact plants and is highly susceptible to environmental variations and subjective experience. Instead, it allows for objective and reproducible discrimination through chemical fingerprinting combined with pattern recognition. Furthermore, the OPLS-DA model was used to quantify the contribution of each component to inter-group separation. This led to the identification of 32 differential components between L. bulbifera and G. diversifolia, 27 between L. bulbifera and U. mairei, and 13 between G. diversifolia and U. mairei. These differential constituents provided important chemical references for the discrimination of Honghema and its easily confusable species under different application scenarios. Furthermore, Venn diagram analysis identified highly specific species-exclusive markers. Twenty characteristic differential constituents, represented by flavonoids such as Baimaside and procyanidin B1, were screened as potential markers of L. bulbifera compared with G. diversifolia and U. mairei. Six characteristic differential constituents, including organic acids and terpenoids such as Roxburic acid and Esculentoside B, were identified as key markers distinguishing G. diversifolia from the other two species. Four characteristic differential constituents, mainly carbohydrates such as Isoeucommin A and 3-Hexenyl-beta-glucopyranoside, were screened as key markers for distinguishing U. mairei from L. bulbifera and G. diversifolia. These species-specific constituents provide a chemical basis for controlling medicinal homogeneity, distinguishing between the two botanical origins of Honghema, and identifying the easily confusable species U. mairei in commercial circulation.
It is noteworthy that several of the major components observed in this study have been reported in pharmacological literature to be associated with the anti-inflammatory, analgesic, and anti-RA activities of Honghema. For example, the flavonoid procyanidin B1 in L. bulbifera has been shown to inhibit NLRP3 inflammasome activation via the TLR4/MD-2, NF-κB and MAPK pathways [19]. Catechin has been reported to exert anti-inflammatory activity through the inhibition of NF-κB and MAPK signalling pathways, resulting in reduced expression of inflammatory mediators such as TNF-α and IL-6 [20,21]. Among the terpenoids identified in G. diversifolia, Roxburic acid has been reported to interact with TNF and its receptor TNF-R1, inhibit TNF-induced NF-κB activation, and consequently alleviate inflammatory responses [22]. Esculentoside B could inhibit NF-κB nuclear translocation and reduce the expression of inflammatory factors, thereby contributing to its anti-inflammatory activity [23]. These findings provide potential directions for subsequent selection of differential markers. As these species exhibit substantial chemical and pharmacological differences, establishing objective quality control standards that account for different botanical origins is a critical issue in the clinical application of multi-origin medicinal materials.
Regarding the application of identification methods, the botanical origin identification of Honghema currently relies primarily on traditional plant taxonomy, in which species discrimination is based on morphological characteristics of intact plants, such as leaf shape, stinging hair density, and inflorescence type [24]. However, these methods are susceptible to influence by environmental conditions and subjective experience. Furthermore, as Honghema often undergoes coarse processing, such as cutting, prior to its use as a medicinal material, the critical diagnostic morphological features are largely lost. This significantly increases the difficulty of species identification and hinders the development of objective standards capable of meeting the testing requirements within the medicinal material supply chain. The research strategy established in this study—integrating high-resolution mass spectrometry with the UNIFI database and multivariate statistical analysis—allows for direct detection of medicinal powders and decoction pieces, facilitating high-throughput, high-sensitivity characterisation and rapid structural elucidation. The key characteristic differential components identified can provide quantifiable reference data for the quality control of Honghema medicinal materials and their decoction pieces.
Despite the findings, this study has certain limitations, and future research may be expanded in three key directions. First, the accuracy of characteristic constituent identification should be further improved. Based on the 21 constituents currently confirmed using reference standards, the chemical constituent database of Honghema could be further refined through additional reference standard verification, isolation of individual compounds, and structural elucidation by nuclear magnetic resonance spectroscopy. Second, a quality evaluation system correlated with pharmacological activity should be constructed. Future work could establish quantitative methods for the identified core characteristic components to elucidate their distribution patterns across different botanical origins, geographical locations, and harvest seasons. By integrating this with in vivo and in vitro anti-inflammatory and analgesic assays, the activity of these components can be validated, thereby providing pharmacodynamic support for the selection of marker compounds in Honghema quality standards. Third, identification methods suitable for the supply chain should be refined. On one hand, mass spectrometry imaging could be employed to clarify the spatial distribution of characteristic components within plant tissues, providing more intuitive evidence for botanical origin identification. On the other hand, simplified and easily implemented detection methods, such as thin-layer chromatography and High Performance Liquid Chromatography (HPLC) characteristic fingerprints, could be developed. This would reduce reliance on high-end instrumentation, facilitate routine inspection and rapid on-site screening, and promote the translation of research findings into practical applications.
In conclusion, the screening strategy established in this study provided a reliable technical approach for the identification of Honghema and its easily confusable species. The characteristic differential components identified not only enrich our understanding of the material basis of Honghema but also offer scientific support for the quality control and refinement of quality standards for Honghema, thereby ensuring the safety and efficacy of its clinical application.

4. Materials and Methods

4.1. Sample Preparation

Honghema and its easily confusable samples (L. bulbifera, G. diversifolia and U. mairei) were collected from Guizhou Province, China. After recording the sample information, the impurities and soil were removed. The plants were then spread evenly in a well-ventilated, shaded, and light-protected area for air drying (shade-drying method) until use. The voucher specimens were deposited at the Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences. The specific information is shown in Supplement Table S1.

4.2. Instruments

A high-speed grinder (DFT-50A, LinDa Machinery Co., Ltd., Wenling, China); a Waters SYNAPT XS ion mobility time-of-flight high-resolution mass spectrometer (Waters Corporation, Milford, MA, USA); an ultrasonic cleaner (JP-040S, Shenzhen JieMeng Cleaning Equipment Co., Ltd., Shenzhen, China); a high-speed refrigerated benchtop centrifuge (H1850R, Hunan Xiangyi Laboratory Instrument Development Co., Ltd., Changsha, China); and an electronic balance (ME204/02, Mettler Toledo International Co., Ltd., Greifensee, Switzerland).

4.3. Reagents

Methanol (34860, Merck KGaA, Darmstadt, Germany); distilled water (HR-01, A.S. Watson Group, Hong Kong, China); formic acid (2244621, Thermo Fisher Scientific Inc., Waltham, MA, USA); acetonitrile (34851, Merck KGaA, Darmstadt, Germany). The purity and specifications of the reference standards were presented in Supplementary Table S2.

4.4. Preparation of the Test Solution

The dried whole plant samples of L. bulbifera, G. diversifolia, and U. mairei were cut into 2.5 cm segments and pulverized to obtain sample powder. An accurately weighed 1.0 g portion of the sample powder was mixed with 20 mL of 70% methanol, and then ultrasonicated for 30 min. After centrifugation at 12,000 r·min−1 for 10 min, the supernatant was filtered through a 0.22 μm microporous membrane, and the subsequent filtrate was collected as the test solution.

4.5. Preparation of QC Solutions

Aliquots (100 μL) of all test sample solutions were mixed in equal volumes, and the resulting mixture was divided into aliquots to prepare QC samples. The QC samples were regularly injected throughout the analytical sequence to monitor instrument stability and method reproducibility.

4.6. Preparation of Reference Standard Solutions

Each reference standard was accurately weighed and dissolved to prepare individual standard stock solutions, which were stored at 4 °C protected from light. Appropriate aliquots of each individual standard stock solution were taken and diluted to obtain the mixed standard solution.

4.7. Chromatographic Conditions

Chromatographic analyses of the test solution were performed using a Waters ACQUITY UPLC HSS T3 column (2.1 mm × 100 mm, 1.8 μm). The mobile phase consisted of 0.1% formic acid in water (A) and 0.1% formic acid in acetonitrile (B). Gradient elution was carried out as follows: 0–10 min, 5–100% B; 10–11 min, 100–5% B; 11–13 min, 5% B. The flow rate was 0.5 mL·min−1, the column temperature was maintained at 30 °C, and the injection volume was 2 μL.

4.8. Mass Spectrometer Conditions

Electrospray Ionization (ESI) was employed in mass spectrometry with Elevated Energy (MSE) mode with a scan time of 0.2 s. The capillary voltages were set at 2.00 kV in negative ion mode (ESI−) and 0.5 kV in positive ion mode (ESI+). The cone voltage was 40 V. The ion source temperature was 100 °C, and the desolvation temperature was 450 °C. Nitrogen was used as the desolvation gas at a flow rate of 900 L·h−1, and the cone gas (N2) flow rate was 50 L·h−1. The mass scanning range was set from m/z 50 to 1500. The low collision energy was set at 6 eV, and the high collision energy was ramped from 20 to 70 eV. During the analysis, leucine enkephalin (m/z 556.2766 [M+H]+, m/z 554.2620 [M–H]−) was used for mass axis calibration. The LC-MS data system was controlled and data were acquired and analyzed using MassLynx 4.1 software.

4.9. Identification of Chemical Constituents

By sorting out the research literature [3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58] of L. bulbifera, G. diversifolia, and U. mairei, the chemical composition database was constructed. The above information was imported into the UNIFI software and the analysis parameters were set. The mobile phase reagent was used as a reference to screen the ions that only existed in plant samples. The target compounds were matched by m/z and secondary fragment information, and the compounds corresponding to each molecular ion peak were determined in combination with literature reports.

4.10. Analysis of Differential Components

The raw LC-MS data were imported into Progenesis QI V2.1 software (Waters Corporation, USA) for noise reduction, peak alignment, and normalization. Adduct ions were set as [M+H]+, [M+Na]+, and [2M+H]+ in positive ion mode, and as [M−H]−, [M+Cl]−, [M+HCOO]−, and [2M−H]− in negative ion mode. The processed data were subsequently exported to EZinfo 3.0 software for multivariate statistical analysis, including principal component analysis (PCA) and orthogonal projections to latent structures-discriminant analysis (OPLS-DA). Potential key differential constituents were screened based on the variable importance in projection (VIP) values and intergroup response differences, with the criteria of VIP > 1 and p < 0.05.

5. Conclusions

In this study, UPLC-Q-TOF-MS/MS, combined with multivariate statistical analysis, was employed to systematically compare the chemical compositions of the two botanical origins of Honghema, namely L. bulbifera and G. diversifolia, as well as its easily confusable species U. mairei. Significant differences were observed among the three plant species in terms of both constituent types and relative abundances. Flavonoids represented the predominant constituent class in L. bulbifera, whereas organic acids were the major constituent class in both G. diversifolia and U. mairei. Through OPLS-DA and Venn diagram analyses, characteristic differential constituents of L. bulbifera, G. diversifolia, and U. mairei were screened. These findings provide a basis for the botanical origin authentication and quality evaluation of Honghema and establish a foundation for ensuring the consistency, controllability, and reliability of its clinical application.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/molecules31152614/s1. Figure S1: The MS/MS spectra of reference standards. Table S1: Experimental sample information; Table S2: The Standard compounds for experiments.

Author Contributions

C.H.: writing—review and editing, writing—original draft, conceptualization, validation, and visualization. Y.Z.: writing—review and editing, methodology, validation, investigation, and resources. H.L.: formal analysis, data curation, visualization, validation, and software. D.W.: conceptualization, formal analysis, and visualization. T.L.: validation, visualization, software, formal analysis, and data curation. W.L.: software, formal analysis, and data curation. S.C.: investigation and validation. Z.G.: writing—original draft, validation, data curation, supervision, methodology, resources, and project administration. H.X.: writing—review and editing, writing—original draft, conceptualization, supervision, methodology, resources, and project administration. P.W.: writing—review and editing, writing—original draft, conceptualization, supervision, methodology, resources, and project administration. All authors have read and agreed to the published version of the manuscript.

Funding

This project was supported by the National Natural Science Foundation of China (Grant No. U25A20167), the Fundamental Research Funds for the Central public welfare research institutes (Grant No. ZXKT25041), the National Natural Science Foundation of China (Grant No. 82574682, 82360815), the Natural Science Foundation of Guizhou Province (Qian Ke He Ji Chu-ZK[2024] Zhong Dian 049, Qian Ke He Ji Chu QNA[2025]002), the Excellent Young Talents Plan of Guizhou Province (QKHPTRC-YQK[2023]029) and the Natural Science Research Foundation of Guizhou Provincial Department of Education (Qian Jiao Ji[2023]066).

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

The original contributions presented in this study are included in the article/Supplementary Material. Further inquiries can be directed to the corresponding authors.

Conflicts of Interest

The authors declare no conflicts of interest.

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Molecules 31 02614 g001
Figure 1. The based peak intensity (BPI) chromatograms of UPLC-Q-TOF/MS of L. bulbifera, G. diversifolia, and U. mairei in positive ion mode (A) and negative ion mode (B). The BPI chromatograms of L. bulbifera (C), G. diversifolia (D), and U. mairei (E) in positive ion mode. The BPI chromatograms of L. bulbifera (F), G. diversifolia (G), and U. mairei (H) in negative ion mode.
Figure 1. The based peak intensity (BPI) chromatograms of UPLC-Q-TOF/MS of L. bulbifera, G. diversifolia, and U. mairei in positive ion mode (A) and negative ion mode (B). The BPI chromatograms of L. bulbifera (C), G. diversifolia (D), and U. mairei (E) in positive ion mode. The BPI chromatograms of L. bulbifera (F), G. diversifolia (G), and U. mairei (H) in negative ion mode.
Molecules 31 02614 g001
Molecules 31 02614 g002
Figure 2. Statistics of the compounds of L. bulbifera (A,B), G. diversifolia (C,D), and U. mairei (E,F). Statistics of significantly differential components between L. bulbifera and G. diversifolia (G,H). Statistics of significantly differential components between L. bulbifera and U. mairei (I,J). Statistics of significantly differential components between G. diversifolia and U. mairei (K,L).
Figure 2. Statistics of the compounds of L. bulbifera (A,B), G. diversifolia (C,D), and U. mairei (E,F). Statistics of significantly differential components between L. bulbifera and G. diversifolia (G,H). Statistics of significantly differential components between L. bulbifera and U. mairei (I,J). Statistics of significantly differential components between G. diversifolia and U. mairei (K,L).
Molecules 31 02614 g002
Molecules 31 02614 g003
Figure 3. Identification process and fragmentation pathway of Baimaside (A), Catechin (B), Chlorogenic acid (C), Caffeic acid (D), Ferulic acid (E), 1-O-caffeoylglucose (F), 2-O-alpha-D-Glucopyranosyl-L-ascorbic acid (G), 7,8-Dehydropenstemoside (H), 7-Methoxy-2H-chromen-2-one (I), 9-Ribofuranosyladenine (J), Phenylalanine (K), 1-Monolinolein (L) and 7-Keto-β-Sitosterol (M). Red indicates oxygen-containing functional groups, and blue indicates nitrogen-containing functional groups.
Figure 3. Identification process and fragmentation pathway of Baimaside (A), Catechin (B), Chlorogenic acid (C), Caffeic acid (D), Ferulic acid (E), 1-O-caffeoylglucose (F), 2-O-alpha-D-Glucopyranosyl-L-ascorbic acid (G), 7,8-Dehydropenstemoside (H), 7-Methoxy-2H-chromen-2-one (I), 9-Ribofuranosyladenine (J), Phenylalanine (K), 1-Monolinolein (L) and 7-Keto-β-Sitosterol (M). Red indicates oxygen-containing functional groups, and blue indicates nitrogen-containing functional groups.
Molecules 31 02614 g003
Molecules 31 02614 g004
Figure 4. Multivariate statistical analysis based on chemical compounds from L. bulbifera, G. diversifolia, and U. mairei. PCA score plots of L. bulbifera, G. diversifolia, and U. mairei in positive ion mode (A) and negative ion mode (B). OPLS-DA score plots of L. bulbifera and G. diversifolia in positive ion mode (C) and negative ion mode (D). S-plots of L. bulbifera and G. diversifolia in positive ion mode (E) and negative ion mode (F). OPLS-DA score plots of L. bulbifera and U. mairei in positive ion mode (G) and negative ion mode (H). S-plots of L. bulbifera and U. mairei in positive ion mode (I) and negative ion mode (J). OPLS-DA score plots of G. diversifolia and U. mairei in positive ion mode (K) and negative ion mode (L). S-plots of G. diversifolia and U. mairei in positive ion mode (M) and negative ion mode (N). Points located at the upper-right and lower-left extremes of the “S” shape represent potential key differentiating variables with high contribution and strong reliability.
Figure 4. Multivariate statistical analysis based on chemical compounds from L. bulbifera, G. diversifolia, and U. mairei. PCA score plots of L. bulbifera, G. diversifolia, and U. mairei in positive ion mode (A) and negative ion mode (B). OPLS-DA score plots of L. bulbifera and G. diversifolia in positive ion mode (C) and negative ion mode (D). S-plots of L. bulbifera and G. diversifolia in positive ion mode (E) and negative ion mode (F). OPLS-DA score plots of L. bulbifera and U. mairei in positive ion mode (G) and negative ion mode (H). S-plots of L. bulbifera and U. mairei in positive ion mode (I) and negative ion mode (J). OPLS-DA score plots of G. diversifolia and U. mairei in positive ion mode (K) and negative ion mode (L). S-plots of G. diversifolia and U. mairei in positive ion mode (M) and negative ion mode (N). Points located at the upper-right and lower-left extremes of the “S” shape represent potential key differentiating variables with high contribution and strong reliability.
Molecules 31 02614 g004
Molecules 31 02614 g005
Figure 5. The normalised abundance of the thirty-two significantly differential components between L. bulbifera and G. diversifolia (* p < 0.05, ** p < 0.01, *** p < 0.001).
Figure 5. The normalised abundance of the thirty-two significantly differential components between L. bulbifera and G. diversifolia (* p < 0.05, ** p < 0.01, *** p < 0.001).
Molecules 31 02614 g005
Molecules 31 02614 g006
Figure 6. (A1–A27) The normalised abundance of the twenty-seven significantly differential components between L. bulbifera and U. mairei (* p < 0.05, ** p < 0.01, *** p < 0.001). Black dots represent individual sample data points (n = 6 per group).
Figure 6. (A1–A27) The normalised abundance of the twenty-seven significantly differential components between L. bulbifera and U. mairei (* p < 0.05, ** p < 0.01, *** p < 0.001). Black dots represent individual sample data points (n = 6 per group).
Molecules 31 02614 g006
Molecules 31 02614 g007
Figure 7. (A1–A13) The normalised abundance of the thirteen significantly differential components between G. diversifolia and U. mairei (* p < 0.05, ** p < 0.01, *** p < 0.001). (A14) The Venn diagram of significantly differential components between L. bulbifera vs. G. diversifolia and L. bulbifera vs. U. mairei. (A15) The Venn diagram of significantly differential components between L. bulbifera vs. G. diversifolia and G. diversifolia vs. U. mairei. (A16) The Venn diagram of significantly differential components between L. bulbifera vs. U. mairei and G. diversifolia vs. U. mairei.
Figure 7. (A1–A13) The normalised abundance of the thirteen significantly differential components between G. diversifolia and U. mairei (* p < 0.05, ** p < 0.01, *** p < 0.001). (A14) The Venn diagram of significantly differential components between L. bulbifera vs. G. diversifolia and L. bulbifera vs. U. mairei. (A15) The Venn diagram of significantly differential components between L. bulbifera vs. G. diversifolia and G. diversifolia vs. U. mairei. (A16) The Venn diagram of significantly differential components between L. bulbifera vs. U. mairei and G. diversifolia vs. U. mairei.
Molecules 31 02614 g007
Table 1. Laportea bulbifera chemical compounds identification.
Table 1. Laportea bulbifera chemical compounds identification.
NO.CompoundFormulaObserved RT (min)Molecular MassIonization ModelObserved m/z Mass Error (ppm)Fragment IonsCASClass
1HistidineC6H9N3O20.51155.07[M−H]−154.060.1174.02 [M−H−C4H4N2]−71-00-1Organonitrogen compounds and their derivatives
2L-AsparagineC4H8N2O30.53132.05[M−H]−131.05−3.89114.02 [M−H−NH3]−
113.04 [M−H−H2O]−
72.01 [M−H−C2H5NO]−		70-47-3Organonitrogen compounds and their derivatives
3D-RaffinoseC18H32O160.55504.17[M+Cl]−539.14−0.67341.11 [M−H−C6H10O5]−
323.10 [M−H−C6H12O6]−
179.06 [M−H−C12H20O10]−
175.02 [M−H−C12H24O10]−
161.05 [M−H−C12H22O11]−
143.04 [M−H−C12H24O12]−		512-69-6Carbohydrates and their derivatives
4L-glutamic acidC5H9NO40.56147.05[M+H]+148.060.84130.05 [M+H−H2O]+
104.07 [M+H−CO2]+
74.02 [M+H−C3H6O2]+ 		56-86-0Organonitrogen compounds and their derivatives
5MaltoseC12H22O110.56342.12[M+Cl]−377.09−1.50323.10 [M−H−H2O]−
179.06 [M−H−C6H10O5]−
161.05 [M−H−C6H12O6]−		69-79-4Carbohydrates and their derivatives
6D-Galactono-1,4-lactoneC6H10O60.57178.05[M+COOH]−223.05−2.05159.03 [M−H−H2O]−
147.03 [M−H−CH2O]−
117.02 [M−H−C2H4O2]−
87.01 [M−H−C3H6O3]−		2782-07-2Carbohydrates and their derivatives
72-O-alpha-D-Glucopyranosyl-L-ascorbic acid *C12H18O110.61338.08[M−H]−337.08−1.71277.06 [M−H−C2H4O2]−
175.02 [M−H−C6H10O5]−
157.01 [M−H−C6H12O6]−
99.01 [M−H−C8H14O8]−		129499-78-1Carbohydrates and their derivatives
8L-ValineC5H11NO20.61117.08[M+H]+118.091.0272.08 [M+H−CH2O2]+ 72-18-4Organonitrogen compounds and their derivatives
9Malic acidC4H6O50.62134.02[M−H]−133.01−3.11115.00 [M−H−H2O]−
72.99 [M−H−C2H4O2]−		6915-15-7Organic acids and their derivatives
10Citric acid *C6H8O70.66192.03[M−H]−191.02−2.01173.01 [M−H−H2O]−
129.02 [M−H−CH2O3]−
87.01 [M−H−C3H4O4]−		77-92-9Organic acids and their derivatives
119-Ribofuranosyladenine *C10H13N5O41.04267.10[M+H]+268.100.90136.06 [M+H−C5H8O4]+
119.04 [M+H−C5H11NO4]+		58-61-7Organonitrogen compounds and their derivatives
12L-TyrosineC9H11NO31.06181.07[M+H]+182.08−0.57165.05 [M+H−NH3]+
147.04 [M+H−H5NO]+ 		60-18-4Organonitrogen compounds and their derivatives
13GuanosineC10H13N5O51.15283.09[M−H]−282.08−0.68150.04 [M−H−C5H8O4]−
133.02 [M−H−C5H11NO4]−		118-00-3Organonitrogen compounds and their derivatives
14HomoarbutinC13H18O71.28286.11[M+COOH]−331.100.69123.05 [M−H−C6H10O5]−25712-94-1Carbohydrates and their derivatives
15p-Hydroxybenzoic acidC7H6O31.44138.03[M−H]−137.020.6793.03 [M−H−CO2]−99-96-7Organic acids and their derivatives
161-Galloyl-glucoseC13H16O101.46332.07[M−H]−331.070.81168.01 [M−H−C6H11O5]−
153.02 [M−H−C6H10O6]−		554-37-0Carbohydrates and their derivatives
17CardiosperminC11H17NO71.47275.10[M−H]−274.09−1.14256.08 [M−H−H2O]−
89.02 [M−H−C8H11NO4]−		54525-10-9Carbohydrates and their derivatives
18Phenylalanine *C9H11NO21.52165.08[M+H]+166.09−0.92149.06 [M+H−NH3]+
131.05 [M+H−H5NO]+
120.08 [M+H−CH2O2]+
103.05 [M+H−CH5NO2]+
91.05 [M+H−C2H5NO2]+
77.04 [M+H−C3H7NO2]+		63-91-2Organonitrogen compounds and their derivatives
19Tryptophan *C11H12N2O21.55204.09[M+H]+205.10−1.18188.07 [M+H−NH3]+
118.07 [M+H−C3H5NO2]+		73-22-3Organonitrogen compounds and their derivatives
20Pantothenic acidC9H17NO51.61219.11[M+H]+220.120.23202.11 [M+H−H2O]+
148.06 [M+H−C4H8O]+ 		79-83-4Organonitrogen compounds and their derivatives
213,3′,5-Trihydroxy-4′,7-dimethoxyflavanoneC17H16O71.65332.09[M+H]+333.102.84165.05 [M+H−C8H8O4]+
137.02 [M+H−C10H12O4]+		79995-67-8Flavonoids and their derivatives
22Protocatechuic acid 3-glucoside *C13H16O91.66316.08[M−H]−315.07−0.44152.01 [M−H−C6H11O5]−
109.03 [M−H−C7H10O7]−
108.02 [M−H−C7H11O7]−		20300-54-3Carbohydrates and their derivatives
23(-)-EpigallocatechinC15H14O71.76306.07[M−H]−305.07−0.51179.04 [M−H−C6H6O3]−
125.02 [M−H−C9H8O4]− 		970-74-1Flavonoids and their derivatives
243,6-DihydroxycoumarinC9H6O41.82178.03[M+H]+179.031.61123.04 [M+H−2CO]+3450-80-4Coumarins and their derivatives
25Gallocatechin-(4alpha->8)-epicatechinC30H26O131.83594.14[M−H]−593.130.72441.08 [M−H−C8H8O3]−
423.07 [M−H−C8H10O4]−
407.08 [M−H−C8H10O5]−
182.02 [M−H−C22H19O8]−
125.02 [M−H−C24H20O10]−
109.03 [M−H−C24H20O11]−		79199-56-7Flavonoids and their derivatives
26(−)-Epicatechin-3-O-gallateC22H18O101.84442.09[M−H]−441.080.69423.07 [M−H−H2O]−
305.07 [M−H−C7H4O3]−
289.07 [M−H−C7H4O4]−
125.02 [M−H−C16H12O7]−		1257-08-5Flavonoids and their derivatives
27Vanillic acid beta-D-glucopyranosyl esterC14H18O91.86330.10[M−H]−329.09−0.76191.06 [M−H−C7H6O3]−
167.04 [M−H−C6H10O5]−
165.02 [M−H−C6H12O5]−
109.03 [M−H−C8H12O7]−		68985-14-8Carbohydrates and their derivatives
28Hyperoside *C21H20O121.92464.10[M+H]+465.102.52303.05 [M+H−C6H10O5]+
285.04 [M+H−C6H12O6]+
247.06 [M+H−C8H10O7]+
153.02 [M+H−C14H16O8]+		482-36-0Flavonoids and their derivatives
29Quercetin-3-gentiobioside-7-glucosideC33H40O221.92788.20[M−H]−787.190.39625.14 [M−H−C6H10O5]−
462.08 [M−H−C12H21O10]−
445.08 [M−H−C12H22O11]−
299.02 [M−H−C18H32O15]−		-Flavonoids and their derivatives
30Cryptochlorogenic acid *C16H18O91.94354.10[M−H]−353.09−1.10191.06 [M−H−C9H6O3]−
179.04 [M−H−C7H10O5]−
135.05 [M−H−C8H10O7]−		905-99-7Organic acids and their derivatives
311H-indole-2-carbaldehydeC9H7NO2.06145.05[M+H]+146.06−0.86118.07 [M+H−CO]+19005-93-7Organonitrogen compounds and their derivatives
32EsculinC15H16O92.09340.08[M−H]−339.07−1.46303.05 [M−H−2H2O]−
177.02 [M−H−C6H10O5]−
161.02 [M−H−C6H10O6]−		531-75-9Coumarins and their derivatives
33ProcyanidinC30H26O132.16594.14[M+H]+595.151.33307.08 [M+H−C15H12O6]+
291.09 [M+H−C15H12O7]+
181.05 [M+H−C21H18O9]+		4852-22-6Flavonoids and their derivatives
34Vanillic acidC8H8O42.17168.04[M+H]+169.051.09151.04 [M+H−H2O]+
139.04 [M+H−CH2O]+
121.03 [M+H−CH4O2]+
107.05 [M+H−CH2O3]+ 		121-34-6Organic acids and their derivatives
35Caffeic acidC9H8O42.17180.04[M−H]−179.03−0.06135.05 [M−H−CO2]−
109.03 [M−H−C3H2O2]−		331-39-5Organic acids and their derivatives
367-Methoxy-2H-chromen-2-one *C10H8O32.18176.05[M+H]+177.050.80163.04 [M+H−CH2]+
159.04 [M+H−H2O]+
145.03 [M+H−CH4O]+
133.03 [M+H−C2H4O]+
121.03 [M+H−C3H4O]+		531-59-9Coumarins and their derivatives
37Epiafzelechin 5-O-beta-D-glucopyranosideC21H24O102.27436.14[M+COOH]−481.140.11301.07 [M−H−C5H10O4]−
165.06 [M−H−C12H14O7]−
151.04 [M−H−C13H16O7]−
137.06 [M−H−C13H14O8]−		-Flavonoids and their derivatives
38Ruberythric acidC25H26O132.29534.14[M−H]−533.130.50515.12 [M−H−H2O]−
383.08 [M−H−C5H10O5]−		152-84-1Organic acids and their derivatives
39Corchoionoside AC19H32O82.29388.21[M+Na]+411.200.83191.14 [M+H−C6H14O7]+189351-14-2Carbohydrates and their derivatives
40Polygalatenoside BC19H28O102.33416.17[M+Na]+439.162.71399.17 [M+H−H2O]+
237.11 [M+H−C6H12O6]+		-Carbohydrates and their derivatives
413-Caffeoylshikimic acidC16H16O82.35336.08[M+H]+337.092.23291.09 [M+H−CH2O2]+
215.06 [M+H−C7H6O2]+
165.05 [M+H−C7H8O5]+
163.04 [M+H−C7H10O5]+
145.03 [M+H−C7H12O6]+
135.04 [M+H−C8H10O6]+		180981-12-8Organic acids and their derivatives
42p-Coumaric acidC9H8O32.37164.05[M−H]−163.04−0.27119.05 [M−H−CO2]−
93.03 [M−H−C3H2O2]−
71.01 [M−H−C6H4O]− 		7400-08-0Organic acids and their derivatives
43ProtocatechualdehydeC7H6O32.37138.03[M+H]+139.042.23111.04 [M+H−CO]+
93.03 [M+H−CH2O2]+		139-85-5Organic acids and their derivatives
44LeiocarposideC27H34O162.38614.18[M+Cl]−649.162.05289.07 [M−H−C12H20O10]−
165.02 [M−H−C19H28O12]−
121.03 [M−H−C20H28O14]−		71953-77-0Carbohydrates and their derivatives
45Isochlorogenic acid CC25H24O122.39516.13[M+H]+517.142.62499.12 [M+H−H2O]+
473.11 [M+H−C2H4O]+
137.06 [M+H−C17H16O10]+
111.04 [M+H−C19H18O10]+		89886-30-6Organic acids and their derivatives
46Secoisolariciresinol diglucosideC32H46O162.42686.28[M+COOH]−731.27−3.57361.17 [M−H−C12H20O10]−
297.11 [M−H−C14H28O12]−
135.05 [M−H−C24H38O14]−		158932-33-3Others
47FraxinC16H18O102.45370.09[M−H]−369.080.02205.01 [M−H−C6H12O5]−524-30-1Coumarins and their derivatives
48GenipinC11H14O52.46226.08[M−H]−225.08−1.41123.05 [M−H−C4H6O3]−6902-77-8Terpenoids and their derivatives
49Procyanidin B1 *C30H26O122.49578.14[M−H]−577.14−0.01451.10 [M−H−C6H6O3]−
425.09 [M−H−C8H8O3]−
407.08 [M−H−C8H10O4]−
289.07 [M−H−C15H12O6]−
245.05 [M−H−C17H16O7]−		20315-25-7Flavonoids and their derivatives
50Olivil 4′-O-beta-D-glucopyranosideC26H34O122.50538.21[M−H]−537.20−0.17339.12 [M−H−C6H14O7]−
325.11 [M−H−C7H16O7]−
205.05 [M−H−C15H24O8]−
149.02 [M−H−C18H28O9]−
135.05 [M−H−C18H26O10]−
123.05 [M−H−C19H26O10]−
119.05 [M−H−C18H26O11]−		76880-93-8Carbohydrates and their derivatives
51Quercetin-3-O-beta-D-glucose-7-O-beta-D-gentiobioside *C33H40O222.53788.20[M+H]+789.211.41627.16 [M+H−C6H10O5] + 465.10 [M+H−C12H20O10]+
303.05 [M+H−C18H30O15]+
285.04 [M+H−C18H32O16]+		60778-02-1Flavonoids and their derivatives
52Ferulic acid *C10H10O42.55194.06[M−H]−193.05−1.74178.03 [M−H−CH3]−
149.06 [M−H−CO2]−
134.04 [M−H−C2H3O2]−
71.01 [M−H−C7H6O2]−		1135-24-6Organic acids and their derivatives
53Benzyl alcohol xylopyranosyl(1 → 6)glucopyranosideC18H26O102.56402.15[M−H]−401.14−1.71269.10 [M−H−C5H8O4]−
161.05 [M−H−C12H16O5]−		130622-31-0Carbohydrates and their derivatives
54NicotiflorinC27H30O152.63594.16[M+H]+595.170.26559.14 [M+H−2H2O]+
177.02 [M+H−C18H26O11]+		17650-84-9Flavonoids and their derivatives
553-(3-hydroxy-1-butenyl)-2,4,4-trimethyl-2-cyclohexen-1-ketoneC13H20O22.64208.15[M+H]+209.15−1.28191.14 [M+H−H2O]+
167.14 [M+H−C2H2O]+
151.11 [M+H−C3H6O]+		-Others
56Creoside IVC17H32O102.65396.20[M−H]−395.19−0.77235.12 [M−H−C7H12O4]−
191.06 [M−H−C10H20O4]−
173.05 [M−H−C10H22O5]−
87.01 [M−H−C14H28O7]−		-Carbohydrates and their derivatives
57Chlorogenic acid *C16H18O92.66354.10[M−H]−353.09−1.87191.06 [M−H−C9H6O3]−
179.04 [M−H−C7H10O5]−
173.05 [M−H−C9H8O4]−
135.05 [M−H−C8H10O7]−		327-97-9Organic acids and their derivatives
583′-HydroxymelanettinC16H12O62.68300.06[M+H]+301.071.74269.04 [M+H−CH4O]+
175.04 [M+H−C6H6O3]+
134.04 [M+H−C8H7O4]+		200391-95-3Flavonoids and their derivatives
59Sinapic Acid *C11H12O52.69224.07[M−H]−223.06−3.37179.07 [M−H−CO2]−
164.05 [M−H−C2H3O2]−		7362-37-0Organic acids and their derivatives
60Isorhamnetin 3-O-alpha-rhamnopyranosyl-(1-2)-beta-galactopyranosideC28H32O162.72624.17[M+H]+625.18−0.43433.11 [M+H−C7H12O6]+
123.04 [M+H−C21H26O14]+		107740-46-5Flavonoids and their derivatives
61Catechin *C15H14O62.73290.08[M−H]−289.07−2.07165.02 [M−H−C7H8O2]−
151.04 [M−H−C7H6O3]−
137.02 [M−H−C8H8O3]−
125.02 [M−H−C9H8O3]−
109.03 [M−H−C9H8O4]−		154-23-4Flavonoids and their derivatives
62Eriodictyol 7-O-glucosideC21H22O112.75450.12[M−H]−449.11−1.27431.10 [M−H−H2O]−
287.06 [M−H−C6H10O5]−
151.04 [M−H−C13H14O8]−		38965-51-4Flavonoids and their derivatives
637,8-DehydropenstemosideC17H24O112.78404.13[M−H]−403.12−1.22241.07 [M−H−C6H10O5]−
223.06 [M−H−C6H12O6]−
165.06 [M−H−C8H14O8]−		-Terpenoids and their derivatives
645-Hydroxy-7,4′-dimethoxyflavoneC17H14O52.79298.08[M+COOH]−343.08−1.38175.04 [M−H−C7H6O2]−
167.04 [M−H−C9H6O]−		5128-44-9Flavonoids and their derivatives
65Dichotomoside AC26H32O132.85552.18[M−H]−551.18−1.08389.12 [M−H−C6H10O5]−
193.05 [M−H−C16H22O9]−
135.05 [M−H−C18H24O11]−		845673-17-8Carbohydrates and their derivatives
661-O-caffeoylglucose *C15H18O92.86342.10[M−H]−341.09−0.60305.07 [M−H−2H2O]−
179.04 [M−H−C6H10O5]−
161.02 [M−H−C6H12O6]−
135.05 [M−H−C7H10O7]−		14364-08-0Carbohydrates and their derivatives
67RobinetinC15H10O72.90302.04[M+H]+303.050.30285.04 [M+H−H2O]+
247.06 [M+H−2CO]+
137.02 [M+H−C8H6O4]+		490-31-3Flavonoids and their derivatives
68Myricetin-3-O-α-L-rhamnopyranosideC21H20O122.91464.10[M+H]+465.102.18447.09 [M+H−H2O]+
303.05 [M+H−C6H10O5]+
285.04 [M+H−C6H12O6]+
153.02 [M+H−C14H16O8]+
127.04 [M+H−C15H14O9]+		17912-87-7Flavonoids and their derivatives
69Baimaside *C27H30O172.91626.15[M−H]−625.140.57463.09 [M−H−C6H10O5]−
445.08 [M−H−C6H12O6]−
193.01 [M−H−C18H24O12]−
151.00 [M−H−C20H26O13]−
107.01 [M−H−C21H26O15]−		18609-17-1Flavonoids and their derivatives
70SchaftosideC26H28O142.92564.15[M+H]+565.161.30547.14 [M+H−H2O]+
529.13 [M+H−2H2O]+ 		51938-32-0Flavonoids and their derivatives
71AgnusideC22H26O112.94466.15[M−H]−465.14−0.80303.09 [M−H−C6H10O5]−
285.08 [M−H−C6H12O6]−		11027-63-7Terpenoids and their derivatives
72NarirutinC27H32O142.95580.18[M−H]−579.17−3.43473.11 [M−H−C4H10O3]−
373.09 [M−H−C8H14O6]−
311.06 [M−H−C10H20O8]−
165.06 [M−H−C18H22O11]−		14259-46-2Flavonoids and their derivatives
73Pratensein-7-O-β-D-glucopyranosideC22H22O113.00462.12[M−H]−461.11−0.46299.06 [M−H−C6H10O5]−
283.02 [M−H−C7H14O5]−
267.03 [M−H−C7H14O6]−
161.02 [M−H−C13H16O8]−
123.05 [M−H−C15H14O9]−		36191-03-4Flavonoids and their derivatives
746-Hydroxyluteolin 7-glucosideC21H20O123.01464.10[M−H]−463.090.04283.02 [M−H−C6H12O6]−
133.03 [M−H−C13H14O10]−		54300-65-1Flavonoids and their derivatives
75TangeretinC20H20O73.05372.12[M−H]−371.11−3.25340.10 [M−H−CH3O]−
175.04 [M−H−C10H12O4]−		481-53-8Flavonoids and their derivatives
761-O-(4-Coumaroyl)-beta-D-glucoseC15H18O83.08326.10[M−H]−325.09−0.16147.05 [M−H−C6H10O6]−
119.06 [M−H−C7H10O7]−		7139-64-2Carbohydrates and their derivatives
77Isochlorogenic acid AC25H24O123.09516.13[M−H]−515.12−0.47191.06 [M−H−C18H12O6]−
179.04 [M−H−C16H16O8]−		89919-62-0Organic acids and their derivatives
78(+)-Lariciresinol 4′-glucosideC26H34O113.12522.21[M−H]−521.20−1.21359.15 [M−H−C6H10O5]−
223.10 [M−H−C14H18O7]−
161.05 [M−H−C20H24O6]−
135.05 [M−H−C18H26O9]−		143663-00-7Carbohydrates and their derivatives
79Kaempferol 3-gentiobiosideC27H30O163.14610.15[M+H]+611.160.63449.11 [M+H−C6H10O5]+
287.06 [M+H−C12H20O10]+
269.04 [M+H−C12H22O11]+
153.02 [M+H−C20H26O12]+		22149-35-5Flavonoids and their derivatives
804-O-Feruloylquinic acidC17H20O93.19368.11[M−H]−367.10−0.94191.06 [M−H−C10H8O3]−
134.04 [M−H−C9H13O7]−		2613-86-7Organic acids and their derivatives
81HomoplantagininC22H22O113.24462.12[M+H]+463.122.40301.07 [M+H−C6H10O5]+
286.05 [M+H−C7H13O5]+
163.04 [M+H−C13H16O8]+		17680-84-1Flavonoids and their derivatives
82IsorhamnetinC16H12O7 3.26316.06[M+H]+317.072.50153.02 [M+H−C9H8O3]+480-19-3Flavonoids and their derivatives
83PlantagosideC21H22O123.27466.11[M−H]−465.100.23303.05 [M−H−C6H10O5]−
285.04 [M−H−C6H12O6]−
161.05 [M−H−C15H12O7]−
151.00 [M−H−C14H18O8]−
125.02 [M−H−C15H16O9]−		78708-33-5Flavonoids and their derivatives
84NystoseC24H42O213.28666.22[M+COOH]−711.21−9.75339.09 [M−H−C12H22O10]−
311.10 [M−H−C13H22O11]−
161.05 [M−H−C18H32O16]−		13133-07-8Carbohydrates and their derivatives
85Rutin *C27H30O163.30610.15[M+H]+611.161.65303.05 [M+H−C12H20O9]+
287.06 [M+H−C12H20O10]+		153-18-4Flavonoids and their derivatives
86Alatoside AC21H36O83.41416.24[M+COOH]−461.24−4.91209.12 [M−H−C9H18O5]−-Terpenoids and their derivatives
87Kaempferol *C15H10O63.44286.05[M+H]+287.061.37269.04 [M+H−H2O]+
229.05 [M+H−C2H2O2]+
161.02 [M+H−C6H6O3]+
153.02 [M+H−C8H6O2]+		520-18-3Flavonoids and their derivatives
88Kaempferol-3-O-β-D-glucopyranosideC21H20O113.44448.10[M−H]−447.09−0.94285.04 [M−H−C6H10O5]−
283.02 [M−H−C6H12O5]−
267.03 [M−H−C6H12O6]−
151.00 [M−H−C14H16O7]−
107.01 [M−H−C15H16O9]−		480-10-4Flavonoids and their derivatives
89Quercetin C15H10O73.45302.04[M+H]+303.052.21153.02 [M+H−C8H6O3]+117-39-5Flavonoids and their derivatives
90(3S,7E,9S)-9-Hydroxy-4,7-megastigmadien-3-one 9-glucosideC19H30O73.48370.20[M+H]+371.212.30209.15 [M+H−C6H10O5]+
191.14 [M+H−C6H12O6]+
137.10 [M+H−C10H18O6]+		159813-37-3Others
916,6′,7,7′-Tetramethoxyl-8,8’-biscoumarinC22H18O83.51410.10[M+COOH]−455.09−8.69369.10 [M−H−C2O]−
175.04 [M−H−C12H10O5]−		-Coumarins and their derivatives
92Heptyl 6-O-α-L -arabinopyranosyl-β-D-glucopyranosideC18H34O103.55410.22[M+COOH]−455.21−1.60395.19 [M−H−CH2]−
263.15 [M−H−C6H10O4]−		-Carbohydrates and their derivatives
93(+)-Isolariciresinol 9’-O-glucosideC26H34O113.64522.21[M+COOH]−567.210.43329.14 [M−H−C7H12O6]−
191.06 [M−H−C19H22O5]−
161.05 [M−H−C20H24O6]−		63358-12-3Carbohydrates and their derivatives
944-(3-hydroxy-1-butenyl) -3,5,5-trimethyl-2-cyclohexanoneC13H22O23.65210.16[M+H]+211.17−1.22193.16 [M+H−H2O]+
151.11 [M+H−C3H8O]+
137.10 [M+H−C4H10O]+		-Others
95Cuneataside EC24H40O113.65504.26[M+COOH]−549.26−0.36429.18 [M−H−C4H10O]−
371.21 [M−H−C5H8O4]−
209.15 [M−H−C11H18O9]−
161.05 [M−H−C18H30O6]−
143.04 [M−H−C18H32O7]−		-Terpenoids and their derivatives
96MatairesinosideC26H32O113.69520.19[M+COOH]−565.19−0.26339.12 [M−H−C6H12O6]−
179.06 [M−H−C20H20O5]−
121.03 [M−H−C19H26O9]−		23202-85-9Carbohydrates and their derivatives
97Benzoic acidC7H6O23.71122.04[M−H]−121.03−0.0477.04 [M−H−CO2]−65-85-0Organic acids and their derivatives
98kaempferideC16H12O63.75300.06[M−H]−299.06−0.72284.03 [M−H−CH3]−491-54-3Flavonoids and their derivatives
99InositolC6H12O63.79180.06[M−H]−179.06−0.52161.05 [M−H−H2O]−
89.02 [M−H−C3H6O3]−
59.01 [M−H−C4H8O4]−		87-89-8Others
100ApigeninC15H10O53.82270.05[M+H]+271.061.23153.02 [M+H−C8H6O]+
145.03 [M+H−C6H6O3]+
119.05 [M+H−C7H4O4]+		520-36-5Flavonoids and their derivatives
101Kaempferol 7-O-rhamnosideC21H20O103.82432.11[M−H]−431.10−1.38285.04 [M−H−C6H10O4]−
267.03 [M−H−C6H12O5]−
179.04 [M−H−C12H12O6]−
161.05 [M−H−C15H10O5]−
135.05 [M−H−C13H12O8]−		20196-89-8Flavonoids and their derivatives
102HomoorientinC21H20O113.83448.10[M+H]+449.114.27287.06 [M+H−C6H10O5]+
271.06 [M+H−C6H10O6]+		4261-42-1Flavonoids and their derivatives
103Diosmetin 7-O-beta-D-glucosideC22H22O113.91462.12[M−H]−461.110.24446.09 [M−H−CH3]−
297.04 [M−H−C6H12O5]−
283.02 [M−H−C7H14O5]−		20126-59-4Flavonoids and their derivatives
1044-(3-α-hydroxy-1-butenyl)-3,5,5- trimethyl-2-cyclohexen-1-ketoneC13H20O24.05208.15[M+H]+209.150.28191.14 [M+H−H2O]+
137.10 [M+H−C4H8O]+		-Others
105Ajugaside AC32H50O144.28658.32[M+COOH]−703.32−1.88495.26 [M−H−C6H10O5]−
333.21 [M−H−C12H20O10]−		213134-86-2Terpenoids and their derivatives
10610-epi-Atractyloside AC21H36O104.38448.23[M+COOH]−493.23−0.94429.21 [M−H−H2O]−-Terpenoids and their derivatives
107KaemferitrinC27H30O144.50578.16[M−H]−577.16−1.01269.05 [M−H−C12H20O9]−
253.05 [M−H−C12H20O10]−		482-38-2Flavonoids and their derivatives
108Ophiopogoside BC26H28O124.76532.16[M−H]−531.15−0.12351.09 [M−H−C6H12O6]−
161.05 [M−H−C20H18O7]−
133.03 [M−H−C18H22O10]−		-Flavonoids and their derivatives
109Luteolin *C15H10O64.77286.05[M−H]−285.04−1.48133.03 [M−H−C7H4O4]−491-70-3Flavonoids and their derivatives
110Lappaol AC30H32O95.15536.20[M+COOH]−581.20−0.91355.12 [M−H−C10H12O3]−
150.03 [M−H−C22H25O6]−		62333-08-8Organic acids and their derivatives
1119,12,13,TriHODEC18H32O55.41328.22[M−H]−327.22−2.09229.14 [M−H−C6H10O]−
211.13 [M−H−C6H12O2]−
183.14 [M−H−C7H12O3]−
171.10 [M−H−C9H16O2]−		-Organic acids and their derivatives
1129,10,13-Trihydroxy-11-octadecenoic acidC18H34O55.77330.24[M−H]−329.23−1.30311.22 [M−H−H2O]−
229.14 [M−H−C6H12O]−
211.13 [M−H−C6H14O2]−
171.10 [M−H−C9H18O2]−
127.11 [M−H−C10H18O4]−		29907-57-1Organic acids and their derivatives
113Euscaphic acidC30H48O56.52488.35[M+COOH]−533.350.82183.14 [M−H−C19H28O3]−53155-25-2Terpenoids and their derivatives
114Interiotherin AC29H28O86.65504.18[M−H]−503.17−0.27367.12 [M−H−C8H8O2]−
150.03 [M−H−C21H21O5]−		181701-06-4Others
1158-Nonenoic acidC9H16O27.05156.12[M+COOH]−201.11−0.64137.10 [M−H−H2O]−31642-67-8Organic acids and their derivatives
116DehydrophytosphingosineC18H37NO37.17315.28[M+H]+316.280.14298.27 [M+H−H2O]+
280.26 [M+H−2H2O]+ 		3687-54-5Organonitrogen compounds and their derivatives
117Oleanolic acidC30H48O37.47456.36[M+H]+457.371.90421.35 [M+H−2H2O]+ 508-02-1Terpenoids and their derivatives
1181,18-Octadec-9-enedioic acidC18H32O47.52312.23[M+Na]+335.22−0.31277.22 [M+H−2H2O]−
109.10 [M+H−C10H20O4]−		20701-67-1Organic acids and their derivatives
1199-HOTrEC18H30O37.52294.22[M−H]−293.21−2.20275.20 [M−H−H2O]−
185.12 [M−H−C8H12]−
171.10 [M−H−C9H14]−
167.11 [M−H−C8H14O]−		89886-42-0Organic acids and their derivatives
120(5R)-1-(3,4-Dimethoxyphenyl)-5-hydroxydecan-3-oneC18H28O47.54308.20[M−H]−307.19−1.33165.09 [M−H−C8H14O2]−
127.11 [M−H−C10H12O3]−		-Others
121Octadecanedioic acidC18H34O47.69314.25[M−H]−313.24−9.74277.22 [M−H−2H2O]−871-70-5Organic acids and their derivatives
1229-Hydroperoxy-10,12,15-octadecatrienoic acidC18H30O48.22310.21[M+Na]+333.20−4.04293.21 [M+H−H2O]+
121.10 [M+H−C9H18O4]+
109.10 [M+H−C10H18O4]+
107.09 [M+H−C10H20O4]+
97.03 [M+H−C13H26O2]+
81.07 [M+H−C12H22O4]+		111004-08-1Organic acids and their derivatives
1231-Monolinolein *C21H38O48.58354.28[M+H]+355.280.04337.27 [M+H−H2O]+
263.24 [M+H−C3H8O3]+
81.07 [M+H−C15H30O4]+		2277-28-3Lipids and their derivatives
124Gingerglycolipid BC33H58O148.58678.38[M+COOH]−723.380.50415.15 [M−H−C18H30O]−
397.14 [M−H−C18H32O2]−
309.21 [M−H−C15H28O10]−		88168-90-5Carbohydrates and their derivatives
1259R-Hydroxy-10E,12Z-octadecadienoic acidC18H32O38.72296.24[M−H]−295.23−0.62277.22 [M−H−H2O]−
195.14 [M−H−C6H12O]−
171.10 [M−H−C9H16]−		10075-11-3Organic acids and their derivatives
126Echinocystic acidC30H48O48.77472.36[M−H]−471.350.35453.34 [M−H−H2O]−
407.33 [M−H−CH4O3]−		510-30-5Terpenoids and their derivatives
127Dibutyl phthalateC16H22O49.00278.15[M+Na]+301.141.62149.02 [M+H−C8H18O]+84-74-2Lipids and their derivatives
1281-Palmitoyl-galactosylglycerolC25H48O99.45492.33[M+Na]+515.32−6.94313.27 [M+H−C6H12O6]+-Lipids and their derivatives
12912-Hydroxypentanoic acid methyl esterC15H30O39.74258.22[M−H]−257.21−0.92211.21 [M−H−CH2O2]−-Lipids and their derivatives
130Linolenic acidC18H30O210.14278.22[M−H]−277.22−0.92235.17 [M−H−C3H6]−
195.14 [M−H−C6H10]−		463-40-1Organic acids and their derivatives
1317-Keto-β-SitosterolC29H48O210.64428.37[M+H]+429.371.68411.36 [M+H−H2O]+
313.22 [M+H−C8H20]+
109.06 [M+H−C22H40O]+		2034-74-4Steroids and their derivatives
132Linoleic acidC18H32O210.64280.24[M−H]−279.23−1.97261.22 [M−H−H2O]−
189.13 [M−H−C5H14O]−
163.11 [M−H−C7H16O]−
137.10 [M−H−C9H18O]−		60-33-3Organic acids and their derivatives
1339(Z)-OctadecenamideC18H35NO10.77281.27[M+H]+282.283.7895.09 [M+H−C11H25NO]+
86.10 [M+H−C13H24O]+
81.07 [M+H−C12H27NO]+
67.05 [M+H−C13H29NO]+		301-02-0Organonitrogen compounds and their derivatives
The symbol ‘*’ indicates compounds were identified using standard substances, the remaining compounds were identified by fragmentation regularities.
Table 2. Girardinia diversifolia chemical compounds identification.
Table 2. Girardinia diversifolia chemical compounds identification.
NO.CompoundFormulaObserved RT (min)Molecular MassIonization ModelObserved m/z Mass Error (ppm)Fragment IonsCASClass
1Gluconic acidC6H12O70.56196.06[M−H]−195.05−1.45177.04 [M−H−H2O]−
165.04 [M−H−CH2O]−
105.02 [M−H−C3H6O3]−		526-95-4Organic acids and their derivatives
22-O-alpha-D-Glucopyranosyl-L-ascorbic acid *C12H18O110.60338.08[M−H]−337.08−0.52175.02 [M−H−C6H10O5]−
157.01 [M−H−C6H12O6]−		129499-78-1Carbohydrates and their derivatives
3Malic acidC4H6O50.61134.02[M−H]−133.01−2.19115.00 [M−H−H2O]−
72.99 [M−H−C2H4O2]−		6915-15-7Organic acids and their derivatives
49-Ribofuranosyladenine *C10H13N5O41.04267.10[M+H]+268.102.03136.06 [M+H−C5H8O4]+
119.04 [M+H−C5H11NO4]+		58-61-7Organonitrogen compounds and their derivatives
5GuanosineC10H13N5O51.15283.09[M−H]−282.08−1.09150.04 [M−H−C5H8O4]−
133.02 [M−H−C5H11NO4]−		118-00-3Organonitrogen compounds and their derivatives
6p-Hydroxybenzoic acidC7H6O31.44138.03[M−H]−137.021.0793.03 [M−H−CO2]−99-96-7Organic acids and their derivatives
7Phenylalanine *C9H11NO21.52165.08[M+H]+166.09−0.34120.08 [M+H−CH2O2]+
103.05 [M+H−CH5NO2]+		63-91-2Organonitrogen compounds and their derivatives
82,5-Dihydroxybenzoic acidC7H6O41.66154.03[M+H]+155.030.79137.02 [M+H−H2O]+
109.03 [M+H−CH2O2]+ 		490-79-9Organic acids and their derivatives
9Protocatechuic acid 3-glucoside *C13H16O91.66316.08[M−H]−315.07−0.46297.06 [M−H−H2O]−
152.01 [M−H−C6H11O5]−
108.02 [M−H−C7H11O7]−		20300-54-3Carbohydrates and their derivatives
10DanshensuC9H10O51.83198.05[M+H]+199.06−1.67181.05 [M+H−H2O]+76822-21-4Organic acids and their derivatives
11Ethyl gallateC9H10O51.83198.05[M−H]−197.05−0.53153.02 [M−H−C2H4O]−
123.01 [M−H−C3H6O2]−		831-61-8Lipids and their derivatives
12c-VeratroylglycolC10H12O51.96212.07[M−H]−211.060.62167.04 [M−H−C2H4O]−168293-10-5Others
131H-indole-2-carbaldehydeC9H7NO2.06145.05[M+H]+146.06−1.34118.07 [M+H−CO]+19005-93-7Organonitrogen compounds and their derivatives
14p-Coumaric acidC9H8O32.37164.05[M−H]−163.04−0.80119.05 [M−H−CO2]−
104.03 [M−H−C2H3O2]− 		7400-08-0Organic acids and their derivatives
15Ferulic acid *C10H10O42.55194.06[M−H]−193.05−2.28178.03 [M−H−CH3]−
149.06 [M−H−CO2]−
134.04 [M−H−C2H3O2]−		1135-24-6Organic acids and their derivatives
16Vitexin 2″−O−glucosideC27H30O152.64594.16[M−H]−593.150.65473.11 [M−H−C4H8O4]−
383.08 [M−H−C7H14O7]−
129.02 [M−H−C22H24O11]−		-Carbohydrates and their derivatives
17Vitamin B2C17H20N4O62.69376.14[M+H]+377.150.84256.15 [M+H−C4N3O2]+
120.08 [M+H−C9H11N3O6]+		83-88-5Organonitrogen compounds and their derivatives
18Dichotomoside AC26H32O132.85552.18[M−H]−551.18−1.95389.12 [M−H−C6H10O5]−
357.13 [M−H−C6H10O7]−		845673-17-8Organic acids and their derivatives
19D-Aspartatic acidC4H7NO42.88133.04[M−H]−132.030.0688.04 [M−H−CO2]−6899-03-2Organonitrogen compounds and their derivatives
20SchaftosideC26H28O142.91564.15[M+H]+565.160.93547.14 [M+H−H2O]+
162.03 [M+H−C17H23O11]+		51938-32-0Flavonoids and their derivatives
21Vitexin 2″-O-xylosideC26H28O142.92564.15[M−H]−563.14−0.30545.13 [M−H−H2O]−
383.08 [M−H−C6H12O6]−		-Carbohydrates and their derivatives
224-Hydroxy-3-methoxycinnamaldehydeC10H10O32.97178.06[M+H]+179.07−2.02161.06 [M+H−H2O]+
151.08 [M+H−CO]+
135.04 [M+H−C2H4O]+
107.05 [M+H−C3H4O2]+		458-36-6Others
233,5,6,8,3′,4′,5′-HeptamethoxyflavoneC22H24O93.06432.14[M+COOH]−477.14−0.69371.11 [M−H−C2H4O2]−
208.04 [M−H−C12H15O4]−
149.02 [M−H−C14H18O6]−		-Flavonoids and their derivatives
24Eleutheroside BC17H24O93.18372.14[M+COOH]−417.14−1.85209.08 [M−H−C6H10O5]−
193.05 [M−H−C7H14O5]−		118-34-3Carbohydrates and their derivatives
25Kaempferol-3-O-β-D-glucopyranosideC21H20O113.44448.10[M−H]−447.09−0.48285.04 [M−H−C6H10O5]−
283.02 [M−H−C6H12O5]−
227.04 [M−H−C8H12O7]−
151.00 [M−H−C14H16O7]−
107.01 [M−H−C15H16O9]−		480-10-4Flavonoids and their derivatives
26ScopoletinC10H8O43.46192.04[M+H]+193.05−0.33178.03 [M+H−CH3]+
122.04 [M+H−C3H3O2]+		92-61-5Coumarins and their derivatives
27(+)-Isolariciresinol 9′-O-glucosideC26H34O113.50522.21[M−H]−521.201.07399.17 [M−H−C7H6O2]−
329.14 [M−H−C7H12O6]−		63358-12-3Carbohydrates and their derivatives
28Denudanolide BC20H22O63.62358.14[M−H]−357.142.30339.12 [M−H−H2O]−
312.10 [M−H−C2H5O]−		-Others
29Caffeic acid cinnamyl esterC18H16O43.39296.10[M+COOH]−341.101.30205.05 [M−H−C7H6]−
163.04 [M−H−C9H8O]−		-Lipids and their derivatives
30(+)-Pinoresinol 4-O-glucosideC26H32O113.59520.19[M−H]−519.19−2.94165.06 [M−H−C17H22O8]−
151.04 [M−H−C18H24O8]−		69251-96-3Carbohydrates and their derivatives
31Benzoic acidC7H6O23.71122.04[M−H]−121.03−0.1277.04 [M−H−CO2]−65-85-0Organic acids and their derivatives
322-(4-Hydroxy-3-methoxy-phenyl)-5-(3-hydroxy-propyl)-7-methoxy-benzofuran-3-carbaldehydeC20H20O63.78356.13[M+H]+357.13−0.88293.08 [M+H−C2H8O2]+
177.05 [M+H−C10H12O3]+		135040-83-4Flavonoids and their derivatives
33ApigeninC15H10O53.82270.05[M+H]+271.060.70153.02 [M+H−C8H6O]+ 520-36-5Flavonoids and their derivatives
34VitexinC21H20O103.82432.11[M−H]−431.10−0.37267.03 [M−H−C6H12O5]−3681-93-4Flavonoids and their derivatives
355alpha-HydroxytriptonideC20H22O74.00374.14[M−H]−373.13−2.23355.12 [M−H−H2O]−
193.05 [M−H−C10H12O3]−
179.07 [M−H−C10H10O4]−
164.05 [M−H−C11H13O4]−		-Others
36MelianoninolC20H20O64.06356.13[M−H]−355.120.29337.11 [M−H−H2O]−
327.12 [M−H−CO]−
325.11 [M−H−CH2O]−
306.09 [M−H−CH5O2]−		136880-81-4Others
37(+)-CabralealactoneC27H42O34.23414.31[M+Na]+437.318.50219.17 [M+H−C12H20O2]+
205.16 [M+H−C13H22O2]+
137.10 [M+H−C18H30O2]+		19865-87-3Terpenoids and their derivatives
38Gossypetin hexamethyl etherC21H22O84.32402.13[M+COOH]−447.13−0.87208.04 [M−H−C11H13O3]−7741-47-1Flavonoids and their derivatives
39Kinobeon AC20H20O64.56356.13[M+COOH]−401.12−0.08177.06 [M−H−C10H10O3]−
162.03 [M−H−C11H13O3]−
148.05 [M−H−C11H11O4]−
134.04 [M−H−C12H13O4]−		155239-87-5Others
40DumetorineC13H21NO24.70223.16[M+H]+224.160.39140.11 [M+H−C5H8O]+
83.05 [M+H−C8H15NO]+
82.07 [M+H−C8H14O2]+ 		96552-67-9Organonitrogen compounds and their derivatives
41(E,7R)-7-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-ene-3,5-dioneC21H22O74.73386.14[M+COOH]−431.142.00207.07 [M−H−C10H10O3]−
192.04 [M−H−C11H13O3]−
177.02 [M−H−C12H16O3]−		-Others
42Luteolin *C15H10O64.77286.05[M−H]−285.040.02133.03 [M−H−C7H4O4]− 491-70-3Flavonoids and their derivatives
431,4-Bis(benzoyloxy)butaneC18H18O44.86298.12[M+Na]+321.119.70165.09 [M+H−C8H6O2]+ 19224-27-2Others
44Methyl-trans-4-hydroxycinnamateC10H10O34.87178.06[M−H]−177.06−0.59117.03 [M−H−C2H4O2]−19367-38-5Lipids and their derivatives
45Lappaol AC30H32O95.15536.20[M+COOH]−581.200.15367.12 [M−H−C9H12O3]−
150.03 [M−H−C22H25O6]−
119.05 [M−H−C22H24O8]−		62333-08-8Organic acids and their derivatives
469,12,13,TriHODEC18H32O55.41328.22[M−H]−327.22−1.63229.14 [M−H−C6H10O]−
211.13 [M−H−C6H12O2]−
171.10 [M−H−C9H16O2]−		-Organic acids and their derivatives
47Esculentoside BC36H56O115.73664.38[M−H]−663.37−0.48515.30 [M−H−C6H12O4]−
501.32 [M−H−C6H10O5]−
487.34 [M−H−C6H8O6]−
467.32 [M−H−C6H12O7]−
453.30 [M−H−C7H14O7]−		60820-94-2Terpenoids and their derivatives
489,10,13-Trihydroxy-11-octadecenoic acidC18H34O55.76330.24[M−H]−329.23−1.18311.22 [M−H−H2O]−
293.21 [M−H−2H2O]−
229.14 [M−H−C6H12O]−
211.13 [M−H−C6H14O2]−
171.10 [M−H−C9H18O2]−		29907-57-1Organic acids and their derivatives
49CyclocurcuminC21H20O66.15368.13[M+H]+369.13−1.28351.12 [M+H−H2O]+
337.11 [M+H−CH4O]+ 		153127-42-5Others
50Ganoderic acid C2C30H46O76.32518.32[M−H]−517.32−1.51499.31 [M−H−H2O]−
473.29 [M−H−C2H4O]−
455.32 [M−H−CH2O3]−
429.30 [M−H−C3H4O3]−		103773-62-2Terpenoids and their derivatives
51Roxburic acidC30H48O66.34504.35[M−H]−503.340.04485.33 [M−H−H2O]−
467.32 [M−H−2H2O]−
441.34 [M−H−CH2O3]−		108657-25-6Terpenoids and their derivatives
52Interiotherin AC29H28O86.65504.18[M−H]−503.170.06367.12 [M−H−C8H8O2]−
150.03 [M−H−C21H21O5]−		181701-06-4Others
53Antheridic acidC19H22O66.66346.14[M+Na]+369.135.17311.13 [M+H−2H2O]+ 34327-25-8Organic acids and their derivatives
54Asiatic acidC30H48O56.94488.35[M−H]−487.34−1.49441.34 [M−H−CH2O2]−
427.32 [M−H−C2H4O2]−
425.34 [M−H−CH2O3]−		464-92-6Terpenoids and their derivatives
55DehydrophytosphingosineC18H37NO37.17315.28[M+H]+316.280.78298.27 [M+H−H2O]+
280.26 [M+H−2H2O]+ 		3687-54-5Organonitrogen compounds and their derivatives
561,18-Octadec-9-enedioic acidC18H32O47.53312.23[M+Na]+335.22−0.23109.10 [M+H−C10H20O4]+
95.09 [M+H−C11H22O4]+		 20701-67-1Organic acids and their derivatives
57tormentic acidC30H48O57.54488.35[M−H]−487.34−0.64469.33 [M−H−H2O]−
441.34 [M−H−CH2O2]−
427.32 [M−H−C2H4O2]−
171.10 [M−H−C21H32O2]−		13850-16-3Terpenoids and their derivatives
58Octadecanedioic acidC18H34O47.68314.25[M−H]−313.24−4.02277.22 [M−H−2H2O]−871-70-5Organic acids and their derivatives
596-MethylgingediolC18H30O48.14310.21[M+Na]+333.20−0.32293.21 [M+H−H2O]+
165.09 [M+H−C8H18O2]+		-Others
609-Hydroperoxy-10,12,15-octadecatrienoic acidC18H30O48.22310.21[M+Na]+333.20−1.46293.21 [M+H−H2O]+
125.10 [M+H−C10H18O3]+
107.09 [M+H−C10H20O4]+
95.09 [M+H−C11H20O4]+ 		111004-08-1Organic acids and their derivatives
611-Monolinolein *C21H38O48.58354.28[M+H]+355.280.45337.27 [M+H−H2O]+
311.26 [M+H−C2H4O]+
263.24 [M+H−C3H8O3]+		2277-28-3Lipids and their derivatives
62Gingerglycolipid BC33H58O148.58678.38[M+COOH]−723.381.48415.15 [M−H−C18H30O]−
397.14 [M−H−C18H32O2]−		88168-90-5Carbohydrates and their derivatives
639R-Hydroxy-10E,12Z-octadecadienoic acidC18H32O38.72296.24[M−H]−295.23−1.03277.22 [M−H−H2O]−
249.22 [M−H−CH2O2]−
195.14 [M−H−C6H12O]−
171.10 [M−H−C9H16]−		10075-11-3Organic acids and their derivatives
64Sumaresinolic acidC30H48O48.77472.36[M−H]−471.35−0.92453.34 [M−H−H2O]−559-64-8Terpenoids and their derivatives
65Nigranoic acidC30H46O48.13470.34[M−H]−469.33−1.21455.32 [M−H−CH2]−
411.33 [M−H−C2H2O2]−
395.30 [M−H−C3H6O2]−		39111-07-4Organic acids and their derivatives
669-oxooctadeca-10,12-dienoic acidC18H30O38.99294.22[M−H]−293.21−2.60275.20 [M−H−H2O]−
171.10 [M−H−C9H14]−		54232-58-5Organic acids and their derivatives
67Dibutyl phthalateC16H22O49.01278.15[M+Na]+301.140.91177.05 [M+H−C6H14O]+
149.02 [M+H−C8H18O]+ 		84-74-2Lipids and their derivatives
68CAULOPHYLLOGENINC30H48O59.08488.35[M+COOH]−533.35−0.27469.33 [M−H−H2O]−
439.32 [M−H−CH4O2]−
253.22 [M−H−C14H18O3]−		52936-64-8Terpenoids and their derivatives
69Mudanpinoic acid AC30H46O39.26454.34[M+H]+455.35−1.88409.35 [M+H−CH2O2]+ 203511-36-8Steroids and their derivatives
7012-Hydroxypentanoic acid methyl esterC15H30O39.74258.22[M−H]−257.21−2.74211.21 [M−H−CH2O2]−-Lipids and their derivatives
71Bis(2-propylpentyl) phthalateC24H38O410.01390.28[M+Na]+413.271.36149.02 [M+H−C16H34O]+70910-37-1Others
7216-O-AcetyldarutigenolC22H36O410.28364.26[M+Na]+387.253.39261.22 [M+H−C4H8O3]+ 1188282-01-0Terpenoids and their derivatives
73Incensole oxideC20H34O310.35322.25[M+Na]+345.240.27263.20 [M+H−C3H8O]+ 21698-66-8Lipids and their derivatives
74BrassicasterolC28H46O10.63398.35[M+H]+399.36−1.33261.22 [M+H−C10H18]+
205.20 [M+H−C13H22O]+
179.14 [M+H−C16H28]+
109.10 [M+H−C20H34O]+		474-67-9Steroids and their derivatives
75Caffeic acid docosanoyl esterC31H50O510.63502.37[M−H]−501.36−1.39391.32 [M−H−C6H6O2]−
279.23 [M−H−C13H18O3]−		-Lipids and their derivatives
767-Keto-β-SitosterolC29H48O210.64428.37[M+H]+429.371.03411.36 [M+H−H2O]+
275.20 [M+H−C11H22]+ 		2034-74-4Steroids and their derivatives
779(Z)-OctadecenamideC18H35NO10.77281.27[M+H]+282.284.0395.09 [M+H−C11H25NO]+
86.10 [M+H−C13H24O]+
81.07 [M+H−C12H27NO]+		301-02-0Organonitrogen compounds and their derivatives
The symbol ‘*’ indicates compounds were identified using standard substances, the remaining compounds were identified by fragmentation regularities.
Table 3. Urtica mairei chemical compounds identification.
Table 3. Urtica mairei chemical compounds identification.
NO.CompoundFormulaObserved RT (min)Molecular MassIonization ModelObserved m/zMass Error (ppm)Fragment IonsCASClass
1Gluconic acidC6H12O70.55196.06[M−H]−195.05−3.67177.04 [M−H−H2O]−
165.04 [M−H−CH2O]−
159.03 [M−H−2H2O]−
105.02 [M−H−C3H6O3]−		526-95-4Organic acids and their derivatives
2D-RaffinoseC18H32O160.56504.17[M+Cl]−539.142.78341.11 [M−H−C6H10O5]−
179.06 [M−H−C12H20O10]−
161.05 [M−H−C12H22O11]−
143.04 [M−H−C12H24O12]−		512-69-6Carbohydrates and their derivatives
3L-ProlineC5H9NO20.58115.06[M+H]+116.071.4585.03 [M+H−CH5N]+
70.07 [M+H−CH2O2]+		147-85-3Organonitrogen compounds and their derivatives
4Malic acidC4H6O50.61134.02[M−H]−133.01−3.44115.00 [M−H−H2O]−
72.99 [M−H−C2H4O2]−		6915-15-7Organic acids and their derivatives
5Citric acid *C6H8O70.66192.03[M−H]−191.02−3.14173.01 [M−H−H2O]−
129.02 [M−H−CH2O3]−
87.01 [M−H−C3H4O4]−		77-92-9Organic acids and their derivatives
69-Ribofuranosyladenine *C10H13N5O41.04267.10[M+H]+268.101.32136.06 [M+H−C5H8O4]+
119.04 [M+H−C5H11NO4]+ 		58-61-7Organonitrogen compounds and their derivatives
7Succinic acidC4H6O41.06118.03[M−H]−117.02−0.4073.03 [M−H−CO2]−110-15-6Organic acids and their derivatives
8GuanosineC10H13N5O51.15283.09[M−H]−282.08−0.35150.04 [M−H−C5H8O4]−
133.02 [M−H−C5H11NO4]−		118-00-3Organonitrogen compounds and their derivatives
9p-Hydroxybenzoic acidC7H6O31.43138.03[M−H]−137.022.7193.03 [M−H−CO2]−99-96-7Organic acids and their derivatives
10Phenylalanine *C9H11NO21.52165.08[M+H]+166.09−0.72120.08 [M+H−CH2O2]+
103.05 [M+H−CH5NO2]+
77.04 [M+H−C3H7NO2]+ 		63-91-2Organonitrogen compounds and their derivatives
11Protocatechuic acid 3-glucosideC13H16O91.66316.08[M−H]−315.07−1.71152.01 [M−H−C6H11O5]−
108.02 [M−H−C7H11O7]−		20300-54-3Carbohydrates and their derivatives
12VanillinC8H8O31.83152.05[M+COOH]−197.05−1.56109.03 [M−H−C2H2O]−121-33-5Others
131H-indole-2-carbaldehydeC9H7NO2.06145.05[M+H]+146.06−0.75118.07 [M+H−CO]+ 19005-93-7Organonitrogen compounds and their derivatives
14EsculinC15H16O92.09340.08[M−H]−339.070.45177.02 [M−H−C6H10O5]−531-75-9Coumarins and their derivatives
15DiosminC28H32O152.49608.17[M+H]+609.180.44301.07 [M+H−C12H20O9]+
286.05 [M+H−C13H23O9]+		520-27-4Flavonoids and their derivatives
16NicotiflorinC27H30O152.64594.16[M+H]+595.170.24559.14 [M+H−2H2O]+
253.13 [M+H−C17H10O8]+		17650-84-9Flavonoids and their derivatives
17Vitexin 2″-O-glucosideC27H30O152.64594.16[M−H]−593.150.39575.14 [M−H−H2O]−
473.11 [M−H−C4H8O4]−
383.08 [M−H−C7H14O7]−		-Carbohydrates and their derivatives
18ApiopaeonosideC20H28O122.71460.16[M−H]−459.150.87310.11 [M−H−C5H9O5]−
151.04 [M−H−C12H20O9]−
121.03 [M−H−C13H22O10]−		100291-86-9Carbohydrates and their derivatives
19SchaftosideC26H28O142.91564.15[M+H]+565.161.63529.13 [M+H−2H2O]+
93.03 [M+H−C20H24O13]+ 		51938-32-0Flavonoids and their derivatives
20Vitexin 2″-O-xylosideC26H28O142.91564.15[M−H]−563.14−0.19545.13 [M−H−H2O]−
383.08 [M−H−C6H12O6]−		-Carbohydrates and their derivatives
215-O-Feruloylquinic acidC17H20O92.95368.11[M+Na]+391.103.12204.06 [M+H−C9H9O3]+
177.05 [M+H−C7H12O6]+
145.03 [M+H−C8H16O7]+		40242-06-6Flavonoids and their derivatives
222-(2-pentenyl) -3-methyl-4-hydroxy-2-pentenyl-1-ketoneC11H16O23.03180.12[M+COOH]−225.110.08149.06 [M−H−C2H6]−
122.04 [M−H−C4H9]−		-Others
233-Hexenyl-beta-glucopyranosideC12H22O63.18262.14[M+COOH]−307.14−0.97191.06 [M−H−C5H10]−
119.04 [M−H−C8H14O2]−
101.02 [M−H−C8H16O3]−		95632-87-4Carbohydrates and their derivatives
244-O-Feruloylquinic acidC17H20O93.19368.11[M−H]−367.101.46191.06 [M−H−C10H8O3]−
177.06 [M−H−C7H10O6]−
71.01 [M−H−C14H16O7]−		2613-86-7Organic acids and their derivatives
25Citrusin BC27H36O133.21568.22[M+Na]+591.200.31207.07 [M+H−C16H26O9]+
179.07 [M+H−C17H26O10]+
163.08 [M+H−C17H26O11]+
137.06 [M+H−C19H28O11]+ 		105279-10-5Carbohydrates and their derivatives
261-beta-GlucogeniposideC17H26O103.22390.15[M+COOH]−435.156.12210.05 [M−H−C7H15O5]−
177.06 [M−H−C7H16O7]−		-Carbohydrates and their derivatives
275,6,7-TrihydroxyflavoneC15H10O53.22270.05[M+H]+271.062.83131.05 [M+H−C6H4O4]+
103.05 [M+H−C7H4O5]+		491-67-8Flavonoids and their derivatives
28Vicenin 2C27H30O153.42594.16[M+H]+595.173.29271.06 [M+H−C12H20O10]+
149.06 [M+H−C18H22O13]+
121.06 [M+H−C19H22O14]+ 		-Flavonoids and their derivatives
29ScopoletinC10H8O43.46192.04[M+H]+193.05−0.34178.03 [M+H−CH3]+
150.03 [M+H−C2H3O]+
122.04 [M+H−C3H3O2]+		92-61-5Coumarins and their derivatives
30MatairesinosideC26H32O113.69520.19[M+COOH]−565.190.20339.12 [M−H−C6H12O6]−
324.10 [M−H−C7H15O6]−
179.06 [M−H−C20H20O5]−		23202-85-9Carbohydrates and their derivatives
31ScoparoneC11H10O43.87206.06[M+H]+207.070.03189.05 [M+H−H2O]+
151.04 [M+H−C3H4O]+
137.06 [M+H−C3H2O2]+		120-08-1Coumarins and their derivatives
32Isoeucommin AC27H34O123.91550.21[M−H]−549.20−3.38369.13 [M−H−C6H12O6]−
249.11 [M−H−C13H16O8]−
153.06 [M−H−C19H24O9]−		-Carbohydrates and their derivatives
33Bruceine CC28H36O124.37564.22[M+Na]+587.210.83467.15 [M+H−C6H10O]+
151.08 [M+H−C19H26O10]+		25514-30-1Terpenoids and their derivatives
34Thujaplicatin methyl etherC21H24O74.51388.15[M−H]−387.150.45369.13 [M−H−H2O]−
357.13 [M−H−CH2O]−
342.11 [M−H−C2H5O]−		6512-67-0Lipids and their derivatives
35Ophiopogoside BC26H28O124.76532.16[M−H]−531.150.73351.09 [M−H−C6H12O6]−
321.08 [M−H−C7H14O7]−		-Flavonoids and their derivatives
36Lappaol AC30H32O95.15536.20[M+COOH]−581.200.40367.12 [M−H−C9H12O3]−
300.10 [M−H−C13H15O4]−
179.07 [M−H−C20H20O6]−
122.04 [M−H−C23H25O7]−		62333-08-8Organic acids and their derivatives
379,12,13,TriHODEC18H32O55.41328.22[M−H]−327.22−1.50291.20 [M−H−2H2O]−
229.14 [M−H−C6H10O]−
211.13 [M−H−C6H12O2]−
171.10 [M−H−C9H16O2]−		-Organic acids and their derivatives
389,10,13-Trihydroxy-11-octadecenoic acidC18H34O55.77330.24[M−H]−329.23−1.65311.22 [M−H−H2O]−
229.14 [M−H−C6H12O]−		29907-57-1Organic acids and their derivatives
39CyclocurcuminC21H20O66.16368.13[M+H]+369.13−0.12351.12 [M+H−H2O]+
337.11 [M+H−CH4O]+
203.07 [M+H−C9H10O3]+
167.07 [M+H−C12H10O3]+		153127-42-5Others
40Piperenol AC21H20O76.25384.12[M+H]+385.130.38367.12 [M+H−H2O]+
323.09 [M+H−C2H6O2]+
177.05 [M+H−C11H12O4]+		134476-89-4Lipids and their derivatives
41DehydrophytosphingosineC18H37NO37.18315.28[M+H]+316.28−0.18298.27 [M+H−H2O]+
280.26 [M+H−2H2O]+		3687-54-5Organonitrogen compounds and their derivatives
42(5R)-1-(3,4-Dimethoxyphenyl)-5-hydroxydecan-3-oneC18H28O47.54308.20[M−H]−307.19−1.17193.09 [M−H−C7H14O]−
139.11 [M−H−C9H12O3]−		-Others
431,2-Dioctanoyl-sn-glycerolC19H36O57.56344.26[M−H]−343.25−1.35201.11 [M−H−C9H18O]−
157.09 [M−H−C11H22O2]−		60514-48-9Lipids and their derivatives
44Nigranoic acidC30H46O48.12470.34[M−H]−469.332.38263.20 [M−H−C13H18O2]−39111-07-4Organic acids and their derivatives
456-MethylgingediolC18H30O48.14310.21[M+Na]+333.20−2.13293.21 [M+H−H2O]+
121.06 [M+H−C10H22O3]+		-Others
469-Hydroperoxy-10,12,15-octadecatrienoic acidC18H30O48.22310.21[M+Na]+333.20−3.82293.21 [M+H−H2O]+
109.10 [M+H−C10H18O4]+
95.09 [M+H−C11H20O4]+		111004-08-1Organic acids and their derivatives
471-Monolinolein *C21H38O48.58354.28[M+H]+355.281.31337.27 [M+H−H2O]+
311.26 [M+H−C2H4O]+
263.24 [M+H−C3H8O3]+		2277-28-3Lipids and their derivatives
48Gingerglycolipid BC33H58O148.58678.38[M+COOH]−723.381.14415.15 [M−H−C18H30O]−
397.14 [M−H−C18H32O2]−		88168-90-5Carbohydrates and their derivatives
499R-Hydroxy-10E,12Z-octadecadienoic acidC18H32O38.72296.24[M−H]−295.23−0.31277.22 [M−H−H2O]−
259.21 [M−H−2H2O]−
249.22 [M−H−CH2O2]−
195.14 [M−H−C6H12O]−
171.10 [M−H−C9H16]−		10075-11-3Organic acids and their derivatives
509-oxooctadeca-10,12-dienoic acidC18H30O38.99294.22[M−H]−293.21−2.68249.22 [M−H−CO2]−
185.12 [M−H−C8H12]−		54232-58-5Organic acids and their derivatives
51Dibutyl phthalateC16H22O49.01278.15[M+Na]+301.141.05149.02 [M+H−C8H18O]+
79.05 [M+H−C10H16O4]+		84-74-2Lipids and their derivatives
52Vitetrifolin EC22H36O49.05364.26[M+H]+365.270.45347.26 [M+H−H2O]+ -Others
53Mudanpinoic acid AC30H46O39.26454.34[M+H]+455.350.01409.35 [M+H−CH2O2]+203511-36-8Steroids and their derivatives
541-Palmitoyl-galactosylglycerolC25H48O99.45492.33[M+Na]+515.32−6.55313.27 [M+H−C6H12O6]+-Lipids and their derivatives
5512-Hydroxypentanoic acid methyl esterC15H30O39.74258.22[M−H]−257.21−1.45211.21 [M−H−CH2O2]−-Lipids and their derivatives
56Bis (2-propylpentyl) phthalateC24H38O410.00390.28[M+Na]+413.271.12149.02 [M+H−C16H34O]+70910-37-1Others
57BrassicasterolC28H46O10.64398.35[M+H]+399.36−0.38179.14 [M+H−C16H28]+
109.10 [M+H−C20H34O]+
81.07 [M+H−C22H38O]+
67.05 [M+H−C23H40O]+		474-67-9Steroids and their derivatives
58Linoleic acidC18H32O210.64280.24[M−H]−279.23−2.19205.16 [M−H−C4H10O]−
163.11 [M−H−C7H16O]−
113.06 [M−H−C12H22]−
83.05 [M−H−C13H24O]−		60-33-3Organic acids and their derivatives
599(Z)-OctadecenamideC18H35NO10.77281.27[M+H]+282.284.62123.12 [M+H−C9H21NO]+
109.10 [M+H−C10H23NO]+
81.07 [M+H−C12H27NO]+ 		301-02-0Organonitrogen compounds and their derivatives
The symbol ‘*’ indicates compounds were identified using standard substances, the remaining compounds were identified by fragmentation regularities.
Table 4. The detailed information of differential compounds between Laportea bulbifera and Girardinia diversifolia.
Table 4. The detailed information of differential compounds between Laportea bulbifera and Girardinia diversifolia.
NO.CompoundVIP ValuepClass
1Baimaside16.99329.23 × 10−4Flavonoids and their derivatives
2Gallocatechin-(4alpha->8)-epicatechin8.83612.72 × 10−6Flavonoids and their derivatives
3Protocatechuic acid 3-glucoside6.55561.61 × 10−2Carbohydrates and their derivatives
4Catechin5.47671.62 × 10−3Flavonoids and their derivatives
5Roxburic acid5.08773.33 × 10−7Terpenoids and their derivatives
6Procyanidin B14.76457.01 × 10−3Flavonoids and their derivatives
7Schaftoside4.34783.04 × 10−6Flavonoids and their derivatives
8Cuneataside E4.21829.60 × 10−3Terpenoids and their derivatives
9Quercetin-3-O-beta-D-glucose-7-O-beta-D-gentiobioside4.20611.56 × 10−2Flavonoids and their derivatives
10Phenylalanine3.68822.96 × 10−7Organonitrogen compounds and their derivatives
119,12,13,TriHODE2.14202.59 × 10−2Organic acids and their derivatives
12Luteolin2.14113.62 × 10−4Flavonoids and their derivatives
13Malic acid1.97323.52 × 10−2Organic acids and their derivatives
14Interiotherin A1.89826.14 × 10−4Others
157,8-Dehydropenstemoside1.86204.74 × 10−3Terpenoids and their derivatives
16Linoleic acid1.74442.81 × 10−3Organic acids and their derivatives
171-Galloyl-glucose1.72058.42 × 10−5Carbohydrates and their derivatives
18Heptyl 6-O-α-L -arabinopyranosyl-β-D-glucopyranoside1.61299.31 × 10−4Carbohydrates and their derivatives
19Esculentoside B1.61049.84 × 10−4Terpenoids and their derivatives
202-O-alpha-D-Glucopyranosyl-L-ascorbic acid1.60061.95 × 10−8Carbohydrates and their derivatives
21Pantothenic acid1.59221.42 × 10−2Organonitrogen compounds and their derivatives
224-O-Feruloylquinic acid1.55553.16 × 10−5Organic acids and their derivatives
23Eriodictyol 7-O-glucoside1.53678.36 × 10−5Flavonoids and their derivatives
24(+)-Lariciresinol 4′-glucoside1.45781.05 × 10−3Carbohydrates and their derivatives
25Benzoic acid1.33954.28 × 10−6Organic acids and their derivatives
266-Hydroxyluteolin 7-glucoside1.32563.17 × 10−3Flavonoids and their derivatives
27Ethyl gallate1.14492.65 × 10−5Lipids and their derivatives
285alpha-Hydroxytriptonide1.09313.29 × 10−6Others
29Epiafzelechin 5-O-beta-D-glucopyranoside1.07661.09 × 10−4Flavonoids and their derivatives
30(−)-Epicatechin-3-O-gallate1.07651.73 × 10−4Flavonoids and their derivatives
315-Hydroxy-7,4′-dimethoxyflavone1.03754.82 × 10−4Flavonoids and their derivatives
32Isochlorogenic acid A1.01613.73 × 10−4Organic acids and their derivatives
Table 5. The detailed information of differential compounds between Laportea bulbifera and Urtica mairei.
Table 5. The detailed information of differential compounds between Laportea bulbifera and Urtica mairei.
NO.CompoundVIP ValuepClass
1Baimaside16.79919.19 × 10−4Flavonoids and their derivatives
2Gallocatechin-(4alpha->8)-epicatechin8.72602.75 × 10−6Flavonoids and their derivatives
3Catechin5.43571.55 × 10−3Flavonoids and their derivatives
4Procyanidin B14.71636.92 × 10−3Flavonoids and their derivatives
5Cuneataside E4.15749.79 × 10−3Terpenoids and their derivatives
6Quercetin-3-O-beta-D-glucose-7-O-beta-D-gentiobioside4.15661.56 × 10−2Flavonoids and their derivatives
7Phenylalanine3.84821.70 × 10−6Organonitrogen compounds and their derivatives
8Kaempferol 7-O-rhamnoside3.37491.80 × 10−3Flavonoids and their derivatives
97,8-Dehydropenstemoside1.92253.26 × 10−3Terpenoids and their derivatives
101-Galloyl-glucose1.89151.30 × 10−5Carbohydrates and their derivatives
11Linoleic acid1.76891.46 × 10−3Organic acids and their derivatives
12Benzyl alcohol xylopyranosyl(1 → 6)glucopyranoside1.71114.28 × 10−3Carbohydrates and their derivatives
132-O-alpha-D-Glucopyranosyl-L-ascorbic acid1.62268.95 × 10−9Carbohydrates and their derivatives
14Heptyl 6-O-α-L-arabinopyranosyl-β-D-glucopyranoside1.59789.07 × 10−4Carbohydrates and their derivatives
15Eriodictyol 7-O-glucoside1.54136.74 × 10−5Flavonoids and their derivatives
164-O-Feruloylquinic acid1.50834.22 × 10−5Organic acids and their derivatives
17(5R)-1-(3,4-Dimethoxyphenyl)-5-hydroxydecan-3-one1.38201.01 × 10−6Others
18Isoeucommin A1.33733.12 × 10−3Carbohydrates and their derivatives
19(+)-Lariciresinol 4′-glucoside1.33242.47 × 10−3Carbohydrates and their derivatives
203-Hexenyl-beta-glucopyranoside1.12831.49 × 10−3Carbohydrates and their derivatives
21D-Galactono-1,4-lactone1.12661.78 × 10−2Carbohydrates and their derivatives
225-Hydroxy-7,4′-dimethoxyflavone1.11531.39 × 10−4Flavonoids and their derivatives
23Epiafzelechin 5-O-beta-D-glucopyranoside1.06701.05 × 10−4Flavonoids and their derivatives
24(−)-Epicatechin-3-O-gallate1.05451.94 × 10−4Flavonoids and their derivatives
25Isochlorogenic acid A1.04852.04 × 10−4Organic acids and their derivatives
263,6-Dihydroxycoumarin1.01318.58 × 10−4Coumarins and their derivatives
27Luteolin1.00452.30 × 10−3Flavonoids and their derivatives
Table 6. The detailed information of differential compounds between Girardinia diversifolia and Urtica mairei.
Table 6. The detailed information of differential compounds between Girardinia diversifolia and Urtica mairei.
NO.CompoundVIP ValuepClass
1Protocatechuic acid 3-glucoside13.30824.29 × 10−5Carbohydrates and their derivatives
2Roxburic acid5.73051.60 × 10−6Terpenoids and their derivatives
3Schaftoside4.93491.98 × 10−5Flavonoids and their derivatives
4Bruceine C4.35062.15 × 10−4Terpenoids and their derivatives
5Luteolin2.93394.07 × 10−5Flavonoids and their derivatives
6Apigenin2.352845.14 × 10−4Flavonoids and their derivatives
7Interiotherin A2.29875.12 × 10−4Others
8Esculentoside B1.92479.60 × 10−4Terpenoids and their derivatives
9Isoeucommin A1.67502.09 × 10−3Carbohydrates and their derivatives
10(5R)-1-(3,4-Dimethoxyphenyl)-5-hydroxydecan-3-one1.50315.06 × 10−6Others
11Dichotomoside A1.27291.36 × 10−2Organic acids and their derivatives
123-Hexenyl-beta-glucopyranoside1.26393.00 × 10−3Carbohydrates and their derivatives
13L-Proline1.19085.00 × 10−3Organonitrogen compounds and their derivatives
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Huang, C.; Zhong, Y.; Li, H.; Wu, D.; Li, T.; Li, W.; Chen, S.; Gong, Z.; Xu, H.; Wang, P. Chemical Profiling and Differential Constituents Analysis of Honghema and Its Easily Confusable Species Driven by High-Resolution Mass Spectrometry and Pattern Recognition. Molecules 2026, 31, 2614. https://doi.org/10.3390/molecules31152614

AMA Style

Huang C, Zhong Y, Li H, Wu D, Li T, Li W, Chen S, Gong Z, Xu H, Wang P. Chemical Profiling and Differential Constituents Analysis of Honghema and Its Easily Confusable Species Driven by High-Resolution Mass Spectrometry and Pattern Recognition. Molecules. 2026; 31(15):2614. https://doi.org/10.3390/molecules31152614

Chicago/Turabian Style

Huang, Congying, Yute Zhong, Han Li, Dan Wu, Taiping Li, Weijie Li, Siying Chen, Zipeng Gong, Haiyu Xu, and Ping Wang. 2026. "Chemical Profiling and Differential Constituents Analysis of Honghema and Its Easily Confusable Species Driven by High-Resolution Mass Spectrometry and Pattern Recognition" Molecules 31, no. 15: 2614. https://doi.org/10.3390/molecules31152614

APA Style

Huang, C., Zhong, Y., Li, H., Wu, D., Li, T., Li, W., Chen, S., Gong, Z., Xu, H., & Wang, P. (2026). Chemical Profiling and Differential Constituents Analysis of Honghema and Its Easily Confusable Species Driven by High-Resolution Mass Spectrometry and Pattern Recognition. Molecules, 31(15), 2614. https://doi.org/10.3390/molecules31152614

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