https://orcid.org/0000-0002-5396-6963
ABSTRACT
In this study, ultra-high performance liquid chromatography-tandem mass spectrometry was used to isolate and identify terpenoids in three types of pineapple fibers (pineapple leaf fiber, pineapple stem fiber, and pineapple root fiber). The research results showed that in the positive and negative ion modes, 9 and 26 terpenoid compounds were identified from the three types of pineapple fibers, totaling 35 species in 12 categories, among which triterpene saponins had the largest number of species. Pineapple root fiber contains the highest total terpenoid content, followed by pineapple stem fiber and leaf fiber. In the OPLS-DA model, the VIP and S-plot methods revealed the differences in terpenoid compounds in three pineapple fibers. The research results showed that there were 9, 8 and 7 significantly different terpenoid compounds in pineapple leaf fiber and pineapple stem fiber, pineapple leaf fiber and pineapple root fiber, and pineapple stem fiber and pineapple root fiber respectively. Functional terpenoids such as ivy saponin, dehydroabietic acid, myrcene and ginsenoside are distributed in different parts of pineapple with varying degrees of enrichment. This study provides a basis for differentiated utilization and value-added use of pineapple leaves, stems and roots. Utilization provides scientific basis.
摘要
本研究采用超高效液相色谱-串联质谱法对三种菠萝纤维（菠萝叶纤维、菠萝茎纤维和菠萝根纤维）中萜类化合物进行分离与鉴定。研究结果表明:在正负离子模式下，从三种菠萝纤维中分别鉴定出9种和26种萜类化合物，共12类35种，其中三萜皂苷种类数最多。菠萝根纤维中总萜类化合物含量最高，其次是菠萝茎纤维和叶纤维。在OPLS-DA模型中VIP和S-plot方法揭示了三种菠萝纤维中萜类化合物的差异性。研究结果表明:菠萝叶纤维与菠萝茎纤维、菠萝叶纤维与菠萝根纤维以及菠萝茎纤维与菠萝根纤维分别存在9种、8种和7种显著差异性萜类化合物。常春藤皂苷、脱氢枞酸、月桂烯和人参皂苷等功能性萜类化合物在菠萝的不同部位皆有分布且富集程度不同，该研究为菠萝叶、茎和根的差异化利用、增值化利用提供了科学依据。
Introduction
Terpenoids are a kind of natural products derived from pentanedioic acid, which are composed of several isoprene structural units, and the general molecular formula is (C5H8) n. Terpenoids can be divided into monoterpene (C10), sesquiterpene (C15), diterpene (C20), triterpene (C30), tetraterpene (C40) and polyterpene (C > 40) (H. G. Liu et al. Citation2022). Except that terpenoids exist in the form of hydrocarbons, terpenoids have various structures, and most of them exist in the form of oxygen-containing derivatives such as alcohols, aldehydes, carboxylic acids and glycosides (H. Y. Chen et al. Citation2022; Rantso, Koekemoer, and Van Citation2022). Terpenoids are widely distributed and have a wide variety. More than 50,000 terpenoids have been reported, which mainly exist in plants such as Compositae, Ranunculaceae and Araliaceae (P. Q. Huang et al. Citation2022; Sarabekov et al. Citation2022).
For the past few years, with the in-depth study of terpenoids, people had found that terpenoids had a variety of biological activities, such as anti-tumor, anti-inflammatory, antibacterial, insecticidal, antiviral, cardiovascular prevention, hypoglycemic and so on (Rantso, Koekemoer, and Van Citation2022; Sulsen et al. Citation2022). Terpenoids represented by paclitaxel and artemisinin had been widely used in clinic (Nawara et al. Citation2020; Syambani Citation2023; Zeng et al. Citation2023). Related research results showed that perillyl alcohol could alleviate chronic restraint stress and aggravate dextran sulfate-induced ulcerative colitis by regulating TLR4/NF-κ B and JAK2/STAT3 signaling pathways (Puppala et al. Citation2022). Menthol, linalool, nerol, etc. had antibacterial effect by inhibiting the activity of biofilm (Faisal et al. Citation2022; R. He et al. Citation2023; R. R. He et al. Citation2023; Ladeira et al. Citation2022; Thirupathi et al. Citation2022). Patchouli alcohol improved diarrhea-predominant irritable bowel syndrome by regulating excitatory nerve transmission in the myenteric plexus of rats (W. Y. Chen et al. Citation2022). Andrographolide could significantly inhibit the growth of Pseudomonas aeruginosa and Staphylococcus aureus (Mu et al. Citation2021; X. Wang Citation2022), and oleanolic acid could inhibit Staphylococcus aureus and Streptococcus mutans (J. H. Li and MonjeGalvan Citation2023; Spivak et al. Citation2020). Ginsenosides Re, Rb3 and Rg had significant therapeutic effects on cardiovascular diseases (X. Chen et al. Citation2022; Trong et al. Citation2022), and it was of great research significance to study terpenoids.
Pineapple [Ananas comosus (Linn.) Merr.] is an important tropical and subtropical fruit, which is deeply loved by people. Pineapple is mainly composed of pineapple crown, fruit, leaves, stems, roots and other parts. The crown of pineapple is used for seedling, and pineapple fruit is used for fresh food and processing, and the leaves, stems, roots of pineapple are basically in a state of waste. Relevant statistics showed that China’s pineapple planting area has exceeded 60,000 hectares, and 1 hectare of pineapple could produce 150 tons of pineapple waste such as leaves, stems and roots, which could produce 9 million tons of pineapple waste every year. At the same time, more than 95% of pineapple waste was crushed and returned to the field, and the annual effective utilization rate was less than 1%, which was basically in a state of waste (Y. J. Liu, Qian, Wang, et al. Citation2023).
According to the existing research reports, pineapple leaf fiber (PLF) contained in pineapple leaves had a porous structure and was rich in triterpenoids, amides, phenylpropanoids and other natural compounds with biological activities, which was not conducive to the growth of bacteria and had a remarkable antibacterial effect (J. L. Wang et al. Citation2009; Zhang Citation2016). Pineapple leaf fiber was also used to improve the mechanical properties of composites (Bala, Balamurugan, and Vijayaragavan Citation2022; Gaba et al. Citation2021). At the same time, many studies had proved that polyphenols were the most representative antibacterial components in PLF (Belghith et al. Citation2022; Faiqa et al. Citation2022; Y. J. Huang et al. Citation2015). However, there were few reports on the separation and identification of terpenoids from pineapple fiber, and the types of terpenoids in pineapple leaf fiber (PLF), pineapple root fiber (PRF) and pineapple stem fiber (PSF) were not clear. Therefore, the separate and identify terpenoids from pineapple leaves, stems and roots were very important and it would provide scientific basis for expanding its application fields, improving its utilization rate and increasing the added value of pineapple industry. Ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS), widely used in pharmaceutical, food safety, life science and other fields, had obvious advantages in structural identification, quality analysis and quantitative analysis due to its high resolution and good sensitivity (Cho et al. Citation2023; Y. J. Liu, Qian, Kuang, et al. Citation2023). Therefore, the terpenoids in PLF, PSF and PRF were separated and identified by the PLF, PSF and PRF. The differential terpenoids were revealed by VIP and S-plot analysis. This study provided theoretical and data support for the comprehensive utilization of pineapple leaves and other by-products.
Materials and methods
Preparation of pineapple fiber
The leaves, stems and roots of pineapple (Bari (1.5-year-old)), collected from Xuwen county pineapple plantation in Zhanjiang City, Guangdong Province in 2022, were washed with clean water and soaked them in water for 24–72 h at room temperature, and beat and cleaned repeatedly with a plastic hammer. The PLF, PSF and PRF were separated, and then dried in the sun.
Extraction of terpenoids
The extraction of terpenoids from pineapple fiber was referred to Wang et al. (Citation2022) and modified appropriately. According to weighing, the average weight of pineapple stems, leaves and roots in a pineapple was .1 kg, 1 kg and .15 kg. A .5 g of sample was cut into 1–2 mm long, and put in a 10 mL centrifuge tube, and 5 mL methanol was added. The centrifuge tube was put in an ice bath pot for ultrasonic extraction at 200 W for 10 min, and the extraction solution was centrifuged at 4°C for 12,000 r/min, and the supernatant was taken out and stored at 4°C for testing.
Determination of terpenoids
The extraction of terpenoids from pineapple fiber was referred to Liu et al. (Citation2023a) and modified appropriately. The UHPLC-MS/MS system used in this study was equipped with a high-performance capillary liquid chromatograph (Ultimate 3000, Thermo Fisher Scientific, USA) with a Sepax GP-C18 Column (1.8 µm 120Å 2.1 mm × 150 mm) and a mass spectrometer (TripleTOF5600+, AB SCIEX™, USA). Ten microliters of terpenoids solution were passed through the column at 40°C and analysis for 21 min. The elution program of mobile phase was performed as 95% A and 5% B for 10 min, 30% A and 70% B for 7 min, 100% B for 2 min, 95% A and 5% B for 13 min, and the eluent flow rate was set to .3 mL/min. Mobile phase A and B consisted of .1% formic acid and 100% acetonitrile, respectively. The detection conditions of mass spectrometer referred to Liu et al. (Citation2023b)
Database search and data analysis
Mass spectrometry database retrieval and data analysis: the suffix collected by the mass spectrometer was wiff file, which was imported into the software MS-DIAL 4.70 software for pre-processing (Tsugawa et al. Citation2015), and the peaks in the mass spectrogram were extracted, denoised, deconvolution and aligned to obtain a three-dimensional data matrix file (original data matrix) with the suffix CSV format. Peak information in three-dimensional data matrix and MassBank, Minimum peak height, Mass slice width, Retention time tolerance, MS1 tolerance, Accurate mass tolerance (MS1), Accurate mass tolerance (MS2) and Identification score cut-off were compared to determine the relevant information of the compound.
The data were statistically analyzed by Excel software. The Origin2022 (2021, OriginLab Corporation, Northampton, UK) and SIMCA 14.1 (14.1, Sartorius Lab Instruments GmbH & Co. KG, Goettingen, Germany) were used to analyze data and make charts. According to the SMILES values in , the molecular formula of the compound was drawn by SMILESDRAWER software.
Table 1. Mass spectrometry information of terpenoids.
Results and discussion
UHPLC-MS/MS mass spectrometry information and spectrum of terpenoids in pineapple fiber samples
The UHPLC-MS/MS positive and negative ion chromatograms of terpenoids in three pineapple fibers are shown in respectively. From , 35 terpenoids were detected from 3 kinds of pineapple fibers, of which 9 were detected in positive ion mode and 26 in negative ion mode. The types and quantities of 12 terpenoids were triterpenoids (6), triterpene saponins (10), terpenes lactones (2), terpenoids (3), sesquiterpenoids (4), menthane monoterpenoids (1), kaurane diterpenoids (1), diterpenoids (2), diterpene lactones (1), diterpene glycosides (3), acyclic monoterpenoids (1), acyclic diterpenoids (1). It could be seen from that the total terpene content of PLF was the highest (5.27 ± .09 mg/g), followed by PRF (4.03 ± .18 mg/g) and PSF (2.63 ± .04 mg/g), and there were significant differences in the total terpene content of three pineapple fibers.
Figure 1. UHPLC-MS/MS mass spectrum of pineapple fiber. A represented the positive ion chromatogram, B represented the negative ion chromatogram, and C represented the peak value of total terpene content.
Species analysis of terpenoids in pineapple fiber samples
Taking the total content of terpenoids in three pineapple fiber samples as the denominator and the content of terpenoids in a single pineapple raw material as the molecule, the figure of terpenoids content ratio and the structural formula of the compounds are shown in , in which the dashed border color of the compounds represented the compound with the largest proportion in the corresponding pineapple fiber.
Figure 2. Proportion and molecular formula of different terpenoids in different pineapple fibers.
It could be seen from that the contents of triterpenoids, triterpene saponins, terpene lactones, terpene glycosides and acyclic monoterpenoids account for the largest proportion in PRF, accounting for 81.0%, 81.4%, 48.9%, 84.8% and 70.5% respectively. The kaurane diterpenoids, diterpenoids, diterpenelatones and acyclic diterpenoids account for the largest proportion in PSF, accounting for 86.0%, 91.0%, 62.3% and 84.5% respectively. The sesquiterpenoids, menthane monoterpenoids and diterpene glycosides accounted for 74.1%, 56.2% and 59.1% respectively in PLF. The distribution of 12 terpenoids in three kinds of pineapple fibers was different. Compounds 1, 2, 12, 13, 16, 23, 24 and 32 were the highest in PSF, and terpenoids exist in various forms such as acids, ketones, alcohols and saponins. Ginsenoside Rg6 (compound 12) regulated platelet function and thrombosis by inhibiting phosphorylated protein (Kwon Citation2020), while ginsenoside Rg2 (compound 16) inhibited Adriamycin-induced cardiomyocyte apoptosis through PI3K/Akt pathway (Qiu et al. Citation2022), so it could be inferred that the pineapple stem had great development value in the extraction of medicinal components and the development of functional products. Compounds 5, 6 and 35 had the highest content in PLF, and terpenoids mainly exist in the form of acids and esters. The content of compound 21 in PRF was the highest, and terpenoids mainly exist in the form of terpenoids, and myrcene (compound 21) had antibacterial, antioxidant, anti-inflammatory and analgesic effects (Cabral et al. Citation2018; Gülruh et al. Citation2023). The content of myrcene in PRF was 3 times that of PSF and 10 times that of PLF, so pineapple root might obtain another important source of myrcene.
S-plot analysis of terpenoids in pineapple fiber samples
S-plot diagram could be used to analyze the difference of target components between two groups of samples. In S-plot diagram, the variables that contribute more to the model were distributed at both ends of “S,” while the variables that contribute less were gathered near the origin (X. W. Huang et al. Citation2022). The S-plot of terpenoids in three pineapple fibers was shown in . The red dot in indicated terpenoids with VIP value > 1, ”+++‘ indicated that terpenoids in the target sample in the compared sample were significantly up-regulated, and ’—” indicated that terpenoids in the target sample in the compared sample were significantly up-regulated. It could be seen from that there were 17 significant terpenoids with VIP value greater than 1 in three pineapple fibers. From , there were 8 terpenoids with significant differences between PRF and PLF. Compared with PRF, two terpenoids in PLF were significantly up-regulated, which were compounds 5 and 35 respectively. Six terpenoids were significantly down-regulated, namely compounds 8, 12, 16, 18, 19 and 26. From , there were 9 terpenoids with significant differences between PSF and PLF. Compared with PSF, two terpenoids in PLF were significantly up-regulated, which were compounds 5 and 35 respectively. Seven terpenoids were significantly down-regulated, namely compounds 9, 11, 12, 13, 16, 23 and 24. From , there were seven terpenoids with significant differences between PRF and PSF. Compared with PRF, one terpenoid in PSF was significantly up-regulated to compound 23. Six terpenoids were significantly down-regulated, namely compounds 8, 12, 16, 18, 19 and 26.
Figure 3. S-plot analysis of terpenoids in pineapple fibers. A represented VIP values of terpenoids in three pineapple fibers, and B, C and D represented S-plot diagrams of PLF-PSF, PLF-PRF and PSF-PRF, respectively.
Thermogram and correlation analysis of terpenoids in pineapple fibers
The OPLS-DA model of 35 terpenoids in three kinds of pineapple fibers was established and VIP analysis was carried out, and 17 terpenoids with VIP values greater than 1 were obtained. After the peak values of the 17 terpenoids were standardized (z value = (X - µ)/σ, where X = standardized random variable, µ = sample mean, σ = sample standard deviation), the thermal maps of three kinds of pineapple fibers were obtained, as shown in . From , the redder the red, the higher the compound content, and the bluer the blue, the lower the compound content. Compounds 5, 6, 7 and 35 were mainly distributed in PLF. Compounds 3, 9, 11, 13, 22, 23, 24, 27, 28, 29, 31, 32 and 33 were mainly distributed in PSFs.
Figure 4. Thermogram and correlation analysis of terpenoids in three kinds of pineapple fibers. A represented thermographic analysis of terpenoids. B represented the correlation analysis of terpenoids. C represented the structural formula of differential terpenoids.
In order to further reveal the correlation of 17 compounds, the correlation plot and molecular structure of terpenoids in three pineapple fibers are shown in respectively. As could be seen from , there was a significant correlation between compound 31 and compound 29, which belonged to diterpenoids and exist in the form of polyols, compound 31 belonged to triterpenoids, and compound 29 might be the precursor of compound 31. Ivy saponin (compound 31) could regulate the migration and apoptosis of esophageal squamous cell carcinoma through reactive oxygen species -p38/JNK pathway (Ren et al. Citation2023), block the expression of STAT3/MMP-2 in PAF/PTAFR axis cascade and inhibit the metastasis of hepatocellular carcinoma cells induced by platelet activating factor (J. B. Chen et al. Citation2023), and the pineapple stem could be used as the source of ivy saponin. At the same time, the content of ɑ-Hederin (compound 31) was higher in the stems and roots of pineapple, which could be preliminarily inferred to play more information transmission roles in the development of stems and roots.
Compound 3 had a significant correlation with 35 and 11 respectively, which might be involved in the metabolic activities of leaves and stems of pineapple. It had been reported that Ganoderic acid LM2 (compound 11) was mainly isolated from the Ganoderma lucidum and had potential anticancer activity (Toshinori et al. Citation2018). There was a significant correlation between compounds 23 and 27. It had been reported that dehydroabietic acid (compound 27) could affect HepG2 hepatoma cells by regulating glycerophospholipid metabolism, iron death, oxidative phosphorylation and endoplasmic reticulum metabolism pathway (Zhikai and Jun Citation2022). Dehydroabietic acid could effectively reduce the expression of survivin in REH-R cells, thus enhancing the therapeutic effect of vincristine on drug-resistant cells (S. L. Li et al. Citation2022). Dehydroabietic acid was mainly distributed in the stem of pineapple, so it was speculated that it was an important terpenoid involved in stem-related metabolism. The above research provided a new direction for the value-added utilization of pineapple stem.
Conclusion
(1) Thirty-five terpenoids, mainly including 12 categories (namely, triterpenoids, triterpene saponins, terpene lactones, terpene glycosides, sesquiterpenoids, menthane monoterpenoids, kaurane diterpenoids, diterpenoids, diterpene lactones, diterpene glycosides, acyclic monoterpenoids and acyclic diterpenoids), were isolated and identified from three pineapple fibers by UHPLC-MS/MS.
(2) There were significant differences in the types and contents of terpenoids in the three pineapple fibers, and there were differences in the expression of terpenoids in the leaves, stems and roots of pineapple.
(3) Among the three kinds of pineapple fibers, the total content of terpenoids in PRF was the highest, followed by PSF and PLF, and the root and stem of pineapple also had great utilization value. In this study, the purification, absolute quantification and functional evaluation of 35 terpenoids in three kinds of pineapple fibers were not evaluated, and further research was needed to provide scientific basis for the comprehensive utilization of pineapple leaves and other by-products.
Highlights
The thirty-five phenols were isolated and identified from PLF, PSF and PRF for first.
The differential terpenoids in three kinds of pineapple fibers were revealed for first.
Functional terpenoids were distributed in different parts of pineapple.
Disclosure statement
No potential conflict of interest was reported by the author(s).
Additional information
Funding
References
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