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Communication

Comparison of Flavonoid Content, Antioxidant Potential, Acetylcholinesterase Inhibition Activity and Volatile Components Based on HS-SPME-GC-MS of Different Parts from Matteuccia struthiopteris (L.) Todaro

by
Xin Wang
1,
Jiatao Guo
1,
Siqi Zang
1,
Baodong Liu
1 and
Yuhuan Wu
2,*
1
College of Life Science and Technology, Harbin Normal University, Harbin 150025, China
2
College of Life and Environmental Sciences, Hangzhou Normal University, Hangzhou 310036, China
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(5), 1142; https://doi.org/10.3390/molecules29051142
Submission received: 30 January 2024 / Revised: 22 February 2024 / Accepted: 28 February 2024 / Published: 4 March 2024
(This article belongs to the Special Issue Nutritional Properties, Sensory Profile and Bioactive Components of Food, 2nd Edition)
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Abstract

:
Matteuccia struthiopteris is one of the most globally consumed edible ferns and widely used in folk medicine. Reports mainly focus on young fronds and the rhizome which are common edible medicinal parts. However, there are few detailed reports on other parts. Therefore, the volatile components of different parts based on HS-SPME-GC-MS were identified, and total flavonoid contents, antioxidant activities and acetylcholinesterase inhibitory activities were compared in order to reveal the difference of volatile components and potential medicinal value of different parts. The results showed that total flavonoid contents, antioxidant activities and volatile components of different parts were obviously different. The crozier exhibited the strongest antioxidant activities, but only underground parts exhibited a dose-dependent inhibition potential against AChE. Common volatile compounds were furfural and 2-furancarboxaldehyde, 5-methyl-. In addition, it was found that some volatile components from adventitious root, trophophyll, sporophyll and petiole were important ingredients in food, cosmetics, industrial manufacturing and pharmaceutical applications.

1. Introduction

Edible ferns have been an important part of vegetable consumption in many countries across the globe because of their high nutritional content [1]. Matteuccia struthiopteris (L.) Todaro is one of the most globally consumed edible ferns widely distributed in Asia, North America and Europe [2]. M. struthiopteris has a long history and is the homology of medicine and food, which was recorded as food in North America as early as 1939 and popular in China, Canada, Korea, United States, India, Russia, and Japan [3,4,5,6,7,8]. Young fronds, the rhizome, and sometimes the whole plant of M. struthiopteris are taken as food. Moreover, M. struthiopteris is widely used in folk medicine to treat several ailments; it is known for its antioxidant, anti-inflammatory, antibacterial, antiviral and antidiabetic activities and prevention of influenza [9]. The main compounds are starch, fatty acid [8,9], flavonoids, stilbenes, steroids and so on [10,11]. In addition, the essential oil from M. struthiopteris contains (E)-phytol, nonanal, and decanal [7], which shows considerable potential development prospect.
M. struthiopteris has been divided into six parts, including adventitious root, trophophyll, sporophyll, rhizome, crozier (young fronds) and petiole, throughout the history of its life. However, until now, there have been few detailed reports on volatile components and active utilization of the six parts which resulted in the limitation of utilization of M. struthiopteris.
Compared with the traditional GC (Gas Chromatography) method, headspace solid-phase micro-extraction gas chromatography–mass spectrometry (HS-SPME-GC-MS) is much more efficient and accurate and can isolate volatiles from plants without solvents [12,13]. Therefore, the volatile components of different parts from M. struthiopteris based on HS-SPME-GC-MS were compared, and antioxidant activities and acetylcholinesterase inhibitory activities were analyzed in detail in order to reveal the differences of volatile components and potential medicinal value of different parts of M. struthiopteris.

2. Results and Discussion

2.1. Total Flavonoid Content of Different Parts from M. struthiopteris

Flavonoids are some of the vital function compounds in plant growth and stress resistance [14,15]. They shows antioxidant activities and health function [16,17]. In our previous reports, it was found that total flavonoid content of fern was much higher than that of bryophytes and some spermatophytes [18,19]. In this paper, total flavonoid contents of different parts from M. struthiopteris including the adventitious root, trophophyll, sporophyll, rhizome, crozier and petiole were obviously different (Figure 1). Thereinto, the total flavonoid content of crozier was the highest (265.67 ± 6.25 mg/g) and similar to that of trophophyll (217.44 ± 11.01), but the total flavonoid content of adventitious root was the lowest (39.68 ± 1.38 mg/g). An unpaired two-tailed t-test showed that the differences were extremely significant (p < 0.001) among different parts of M. struthiopteris. Significant differences might be closely related to the physiological functions of plant organs. Trophophyll of fern is an important organ for capturing the sun’s energy by photosynthesis, and crozier is the part with high plant auxin content. It was proven that flavonoids can stimulate the process of photosynthesis and synthesis of plant auxin [20], which might be result in the high total flavonoid contents of crozier and trophophyll.

2.2. Antioxidant Potential of M. struthiopteris

DPPH free radical and ABTS free radical scavenging activities of the extracts from six parts of M. struthiopteris (adventitious root, trophophyll, sporophyll, rhizome, crozier and petiole) are shown in Figure 2 and Figure 3. It was found that six parts of M. struthiopteris all showed strong DPPH free radical and ABTS free radical scavenging activities, which confirmed strong antioxidant activities of the extract of fern again [18]. The extract of crozier showed the strongest antioxidant activities, but adventitious root and sporophyll exerted weak radical scavenging activity.

2.3. Acetylcholinesterase Inhibition Activity

AChE has proven to be the most viable therapeutic target for symptomatic improvement in AD (Alzheimer’s disease). So far, huperzine A has been a better potent acetylcholinesterase (AChE) inhibitor than tacfin [21]. However, the content of huperzine A in Huperzia serrata is too low, and the species of Huperzia serrata are limited [22]. The discovery of new natural active ingredients for inhibiting AChE is urgent. In this paper, acetylcholinesterase inhibition activity of different parts from M. struthiopteris are determined in Figure 4. The results showed that only the extracts of underground parts (adventitious root and rhizome) exhibited a dose-dependent inhibition potential against AChE.

2.4. Volatile Components of M. struthiopteris by HS-SPME-GC-MS

As vital and potential medicinal compounds, volatile components showed extensive economic value [23,24,25]. In 2007, Miyazawa et al. investigated the essential oil obtained from above-ground parts of M. struthiopteris with diethyl ether, which enriched the utilization of M. struthiopteris. In this paper, the volatile components of adventitious root, trophophyll, sporophyll, rhizome, crozier and petiole were all identified and comparatively analyzed for comprehensive and in-depth development.

2.4.1. Volatile Components of M. struthiopteris

A total of 306 volatile components were found in M. struthiopteris with HS-SPME GC-MS in this paper (Table S1). A total of 35 compounds (Figure 5) with area percentage greater than 3% are listed in Table 1, including hydrocarbon, aldehydes, alcohols, benzene, acids, ketenes and ethers.

2.4.2. Comparative Analysis of Volatile Components from Different Parts of M. struthiopteris

Conducting further analysis based on the results, it was found that the types and contents of volatile components of different parts from M. struthiopteris were significantly different, and strong positive correlations between young crozier and rhizome, adventitious root and trophophyll were detected (Figure 6A). The main volatile components type from young crozier and rhizome of M. struthiopteris is same, but the content is different, which might explain the strong correlations (Figure 6B).
Common compounds in adventitious root, trophophyll, sporophyll, rhizome, crozier and petiole of M. struthiopteris were furfural and 2-furancarboxaldehyde, 5-methyl- (Figure 6B and Figure 7). Among all the volatile components furfural was the volatile compound with the highest content of M. struthiopteris, mainly distributed in rhizome, trophophyll and crozier. 12-Crown-4 mainly distributed in sporophyll. The volatile compound with the highest content in petiole was phthalic acid.
The results showed that some volatile components of M. struthiopteris were important ingredients in food, cosmetics, industrial manufacturing and pharmaceutical applications. Furfural widely distributed in fruits was one of the most important aromatic compounds [26]. Meanwhile, furfural and its derivatives are widely applied in drugs, insecticides, food, even in industry [26,27]. It is worth noting that the content of furfural in crozier and trophophyll was the highest.
1-octen-3-ol was mainly distributed in rhizome of M. struthiopteris was an attractant for Anopheles and Aedes mosquitoes [28] and was able to inhibit Monilinia fructicola in vitro [29]. However, tetradecanoic acid was only distributed in sporophyll of M. struthiopteris; it showed larvicidal and repellent activity against Aedes aegypti (Linn.) and Culex quinquefasciatus (Say.) [30]. Isophytol mainly distributed in the adventitious root of M. struthiopteris is a fragrance ingredient used in the cosmetics industry as well as in non-cosmetic products such as household cleaners and detergents. Ethylene oxide found in the crozier of M. struthiopteris is commonly used in medical treatment and food processing as a sterilizing agent [31,32].
Phenanthrene (only distributed in petiole) and 1, 2-benzenedicarboxylic acid, bis (2-methyl propyl) ester (mainly distributed in the adventitious root) both showed biological toxicity [33]. Nonanal and decanal only found in the trophophyll of M. struthiopteris are antifungal constituents [34], and n-hexadecanoic acid only distributed in the rhizome of M. struthiopteris possesses antioxidant, antibacterial and anti-Inflammatory activities [35].
In addition, based on antioxidant potential and AChE inhibition of different parts of M. struthiopteris, it was speculated that furfural and ethylene oxide might be related to DPPH free radical and ABTS free radical scavenging activities, but isophytol and 1,2-benzenedicarboxylic acid, bis(2-methylpropyl) ester might be related to acetylcholinesterase inhibition activity.

3. Materials and Methods

3.1. Plant Materials

Matteuccia struthiopteris (Figure 8) was collected on 29 September 2020 from the Botanical Garden of Harbin Normal University, where a greenhouse served for scientific research and teaching with proper temperature (18–35 °C), luminous intensity (1500 Lx–3000 Lx) and relative humidity (35~80%) identified by Prof. Baodong Liu.

3.2. Chemicals and Reagents

Rutin (purity > 99.0%), 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and 5,5′-dithiobis-(2-nitrobenzoic acid) (DTNB) were purchased from Aladdin Reagent Int. (Shanghai, China). Acetylcholinesterase was purchased from Yuanye Bio-Technology Co. (Shanghai, China). Acetylthiocholine (ATCh) was purchased from Macklin Bioc-Technology Co. (Shanghai, China).

3.3. Preparation of Plant Extracts

Fresh plants were collected and separated into six parts, including adventitious root, trophophyll, sporophyll, rhizome, crozier and petiole. One sample including six new-collected parts was cleaned quickly and stored in a Ziplock bag for HS-SPME-GC-MS analysis. The other sample was first kept in the shade and then dried at 75 °C in a drying oven for 12 h. The dried and crushed samples were weighed at 1.00 g respectively, then extracted with 70% ethanol twice. The extraction process was conducted in a 50 °C water bath for 2 h; ultrasound-assisted extraction lasted for 20 min. The filtered extracts were prepared for determination of total flavonoid content and bio activities.

3.4. Determination of Total Flavonoid Contents

The method of determination of total flavonoid content was the same as described in our previous report [36]. Rutin was chosen for producing the calibration curves. Different concentrations of rutin extracted with 70% ethanol were mixed with 5% NaNO2 (0.3 mL, 6 min), 5% Al (NO3)3 (0.3 mL, 6 min) and 4% NaOH (4.4 mL, 12 min) in turn, and then the optical density (OD) values of the mixtures at 510 nm were recorded. The optical density values were linearly fitted, and the fitting equation was obtained (y = A + Bx). The determination process of total flavonoid content of the six parts was similar to above steps, and the following formula was used:
Total flavonoid content (mg/g) = [(OD1 + OD2 + OD3)/3 − A]/B × 10/2 × volume/100 × 100%

3.5. Antioxidant Potential (DPPH and ABTS Free Radicals Scavenging Assay)

Radical scavenging activity was determined by detecting the degree of free radical reduction. The methods of DPPH and ABTS free radical scavenging assay were the same as in our previous report [18]. DPPH (0.1 mM) dissolved in 70% ethanol was mixed with extracts of different concentrations in the dark for 30 min, and then optical density values were recorded at 517 nm. The mixture of ABTS (7 mM) dissolved in ultrapure water and potassium persulfate (2.45 mM) was kept in the dark for 12 h before use in order to form the stable blue–green cationic radical ABTS+, namely the ABTS solution. The extracts of different concentrations were mixed with a stable ABTS solution, and the absorbance value was recorded at 734 nm. The experiments described above were both performed in triplicate, and 70% ethanol was taken as control.

3.6. Acetylcholinesterase Inhibition Activity

AChE inhibition activity of extracts of the six parts was measured by the method adopted by Xiao et al. [37]. Acetylcholinesterase catalyzes the formation of choline from acetylcholine and choline reacts with dithio-p-nitrobenzoic acid (DTNB) to form 5-mercapto-nitrobenzoic acid (TNB) which shows a maximum absorption peak at 412 nm.
Samples of different concentrations were added to an acetylcholinesterase solution dissolved in a PBS buffer (PH = 8.0). After the mixture was mixed thoroughly, acetylcholine was added. The reaction was carried out in a 37 °C water bath for 25 min. After the reaction, DTNB was added to the solution for 5 min, and then optical density was recorded at 412 nm. The experiments described above were both performed in triplicate, and 70% ethanol was taken as control.

3.7. Volatile Component Analysis by HS-SPME-GC-MS

Instrumental parameters of volatile component analysis by HS-SPME-GC-MS were same with parameters in previous report [13].

3.8. Data Analysis

Statistical analysis was undertaken using the R software 4.3.1, Prism 8.0.1 and Origin 7.5. Data are reported as the mean of three independent samples.

4. Conclusions

Total flavonoid contents, antioxidant activities and volatile components of different parts from M. struthiopteris were obviously different, which showed that the exploitable values of different parts of M. struthiopteris were different. Specifically, the volatile components of trophophyll, sporophyll, petiole and the underground parts of M. struthiopteris were worthy of further development. Meanwhile, it was proven that the underground parts of M. struthiopteris with stronger antioxidant potential and AChE inhibition activity could probably be used for medicinal purposes. In addition, the microwave method and the enzymatic method could be used for isolating more bioactive molecules.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/molecules29051142/s1, Table S1: Matteuccia struthiopteris compounds.

Author Contributions

Conceptualization, X.W.; methodology, X.W. and J.G.; software, X.W.; validation, S.Z.; formal analysis, X.W.; investigation, J.G.; resources, B.L.; data curation, X.W.; writing—original draft preparation, X.W.; writing—review and editing, X.W.; visualization, X.W.; supervision, X.W. and Y.W.; project administration, X.W.; funding acquisition, Y.W. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by the National Natural Science Foundation of China, grant number 32270215.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Data are available on public.

Acknowledgments

This work was supported by Qin Zhou from Modern Agriculture and the Ecological Environment Academy, Heilongjiang University for HS-SPME-GC-MS.

Conflicts of Interest

The authors declare no conflicts of interest.

References

  1. Chettri, S. Nutrient and Elemental Composition of Wild Edible Ferns of the Himalaya. Am. Fern J. 2018, 108, 95–106. [Google Scholar] [CrossRef]
  2. Giri, P.; Uniyal, P.L. Edible ferns in India and their medicinal uses: A review. Proc. Natl. Acad. Sci. India Sect. B Biol. Sci. 2022, 92, 17–25. [Google Scholar] [CrossRef]
  3. Aderkas, P.V. Economic history of ostrich fern, Matteuccia struthiopteris, the edible fiddlehead. Econ. Bot. 1984, 38, 14–23. [Google Scholar] [CrossRef]
  4. Bushway, A.A.; Serreze, D.V.; McGann, D.F.; True, R.H.; Work, T.M.; Bushway, R.J. Effect of Processing Method and Storage Time on the Nutrient Composition of Fiddlehead Greens. J. Food Sci. 1985, 50, 1491–1492. [Google Scholar] [CrossRef]
  5. Delong, J.; Hodges, D.M.; Prange, R.; Forney, C.; Toivenon, P.; Bishop, M.C.; Elliot, M.; Jordan, M. The unique fatty acid and antioxidant composition of ostrich fern (Matteuccia struthiopteris) fiddleheads. Can. J. Plant Sci. 2011, 91, 919–930. [Google Scholar] [CrossRef]
  6. Liu, Y.J.; Wujisguleng, W.; Long, C.L. Food uses of ferns in China: A review. Acta. Soc. Bot. Pol. 2012, 81, 263–270. [Google Scholar] [CrossRef]
  7. Miyazawa, M.; Horiuchi, E.; Kawata, J. Components of the Essential Oil from Matteuccia struthiopteris. J. Oleo Sci. 2007, 56, 457–461. [Google Scholar] [CrossRef] [PubMed]
  8. Nekrasov, E.V.; Shelikhan, L.A.; Svetashev, V.I. Fatty acid composition of gametophytes of Matteuccia struthiopteris (L.) Tod. (Onocleaceae, Polypodiophyta). Botanica Pacifica 2019, 8, 63–66. [Google Scholar] [CrossRef]
  9. Singla, S.; Rana, R.; Kumar, S.; Thakur, R.; Goyal, S. Matteuccia struthiopteris (L.) Todaro (fiddlehead fern): An updated review. Bull. Nat. Res. Centre 2022, 46, 133. [Google Scholar] [CrossRef]
  10. Li, B.; Ni, Y.; Zhu, L.J.; Wu, F.B.; Yan, F.; Zhang, X.; Yao, X.S. Flavonoids from Matteuccia struthiopteris and their Anti-influenza virus (H1N1) activity. J. Nat. Prod. 2015, 78, 987–995. [Google Scholar] [CrossRef]
  11. Zhang, D.; Li, S.B.; Yang, L.; Li, Y.J.; Zhu, X.X.; Kmoníčková, E.; Zídek, Z.; Fu, M.H.; Fang, J. Two new C-methyl flavanones from the rhizomes and frond bases of Matteuccia struthiopteris. J. Asian Nat. Prod. Res. 2013, 15, 1163–1167. [Google Scholar] [CrossRef]
  12. Karrar, E.; Ahmed, I.A.M.; Wei, W.; Sarpong, F.; Proestos, C.; Amarowicz, R.; Oz, E.; Sheikha, A.F.E.; Allam, A.Y.; Oz, F.; et al. Characterization of volatile flavor compounds in supercritical fluid separated and identified in gurum (Citrulluslanatus var. colocynthoide) seed oil using HSME and GC–MS. Molecules 2022, 27, 3905. [Google Scholar] [CrossRef]
  13. Qi, S.; Zha, L.Y.; Peng, Y.Z.; Luo, W.; Chen, K.L.; Li, X.; Huang, D.F.; Yin, D.M. Quality and metabolomics analysis of Houttuynia cordata based on HS-SPME/GC-MS. Molecules 2022, 27, 3921. [Google Scholar] [CrossRef]
  14. Galluzzo, P.; Marino, M. Nutritional flavonoids impact on nuclear and extranuclear estrogen receptor activities. Genes Nutr. 2006, 1, 161–176. [Google Scholar] [CrossRef]
  15. Zheng, X.; Zhang, X.; Zhao, J.; Yang, R.; Bai, L.; Li, Y.; Prusk, D.; Bi, Y. Metabolomics reveals antioxidant and antifungal functions of flavonoids in the early stage wounded potato tubers. Postharvest Biol. Technol. 2023, 206, 112569. [Google Scholar] [CrossRef]
  16. Cao, H.; Ou, J.Y.; Chen, L.; Zhang, Y.B.; Szkudelski, T.; Delmas, D.; Daglia, M.; Xiao, J.B. Dietary polyphenols and type 2 diabetes: Human Study and Clinical Trial. Crit. Rev. Food Sci. 2019, 59, 3371–3379. [Google Scholar] [CrossRef]
  17. Xiao, J.B.; Chen, X.Q.; Zhang, L.; Talbot, S.G.; Li, G.C.; Xu, M. Investigation of the mechanism of enhanced effect of EGCG on huperzine Aʼs inhibition of acetylcholinesterase activity in rats by a multispectroscopic method. J. Agric. Food Chem. 2008, 56, 910–915. [Google Scholar] [CrossRef]
  18. Wang, X.; Wang, M.L.; Cao, J.G.; Wu, Y.H.; Xiao, J.B.; Wang, Q.X. Analysis of flavonoids and antioxidants in extracts of ferns from Tianmu Mountain in Zhejiang Province (China). Ind. Crop. Prod. 2017, 97, 137–145. [Google Scholar] [CrossRef]
  19. Wang, X.; Cao, J.G.; Dai, X.L.; Xiao, J.B.; Wu, Y.H.; Wang, Q.X. Total flavonoid concentrations of bryophytes from Tianmu Mountain, Zhejiang Province (China): Phylogeny and ecological factors. PLoS ONE 2017, 12, e0173003. [Google Scholar]
  20. Mehmood, A.; Hussain, A.; Irshad, M.; Hamayun, M.; Iqbal, A.; Rahman, H.; Tawab, A.; Ahmad, A.; Ayaz, S. Cinnamic acid as an inhibitor of growth, flavonoids exudation and endophytic fungus colonization in maize root. Plant Physiol. Biochem. 2019, 135, 61–68. [Google Scholar] [CrossRef] [PubMed]
  21. Zhou, H.; Tan, C.H.; Jiang, S.H.; Zhu, D.Y. Serratene-Type Triterpenoids from Huperzia serrata. J. Nat. Prod. 2003, 66, 1328–1332. [Google Scholar] [CrossRef]
  22. Zhu, Q.F.; Zhao, Q.S. Chemical constituents and biological activities of lycophytes and ferns. Chin. J. Nat. Medicines 2019, 17, 887–891. [Google Scholar] [CrossRef]
  23. Huang, H.H.; Lin, L.Y.; Chiang, H.M.; Lay, S.J.; Wu, C.S.; Chen, H.C. Analysis of volatile compounds from different parts of Citrus grandis (L.) Osbeck flowers by headspace solid-phase microextraction-gas chromatography-mass spectrometry. J. Essent. Oil Bear. Plants 2017, 20, 1057–1065. [Google Scholar] [CrossRef]
  24. Nešović, M.; Gašić, U.; Tosti, T.; Horvacki, N.; Nedić, N.; Sredojević, M.; Blagojević, S.; Ignjatović, L.; Tešić, Ž. Distribution of polyphenolic and sugar compounds in different buckwheat plant parts. RSC Adv. 2021, 11, 25816–25829. [Google Scholar] [CrossRef]
  25. Pan, J.; Zheng, W.; Pang, X.; Zhang, J.; Chen, X.; Yuan, M.; Yu, K.; Guo, B.; Ma, B.J.M. Comprehensive investigation on ginsenosides in different parts of a garden-cultivated ginseng root and rhizome. Molecules 2021, 26, 1696. [Google Scholar] [CrossRef] [PubMed]
  26. Eseyin, A.E.; Steele, P.H. An overview of the applications of furfural and its derivatives. Int. J. Adv. Chem. 2015, 3, 42–47. [Google Scholar] [CrossRef]
  27. Kabbour, M.; Luque, R. Chapter 10-Furfural as a platform chemical: From production to applications. Biomass Biofuels Biochem. 2020, 283–297. [Google Scholar]
  28. Xu, P.; Zhu, F.; Buss, G.K.; Leal, W.S. 1-Octen-3-ol—The attractant that repels. F1000Research 2015, 4, 156. [Google Scholar] [CrossRef]
  29. Wang, X.Z.; Huang, M.M.; Peng, Y.; Yang, W.T.; Shi, J.Y. Antifungal activity of 1-octen-3-ol against Monilinia fructicola and its ability in enhancing disease resistance of peach fruit. Food Control 2022, 135, 108804. [Google Scholar] [CrossRef]
  30. Sivakumar, R.; Jebanesan, A.; Govindarajan, M.; Rajasekar, P. Larvicidal and repellent activity of tetradecanoic acid against Aedes aegypti (Linn.) and Culex quinquefasciatus (Say.)(Diptera: Culicidae). Asian Pac. J. Trop. Med. 2011, 4, 706–710. [Google Scholar] [CrossRef]
  31. Lynch, H.N.; Kozal, J.S.; Russell, A.J.; Thompson, W.J.; Divis, H.R.; Freid, R.D.; Calabrese, E.J.; Mundt, K.A. Systematic review of the scientific evidence on ethylene oxide as a human carcinogen. Chem-Biol. Interact. 2022, 364, 110031. [Google Scholar] [CrossRef]
  32. Mendes, G.C.C.; Brandão, T.R.S.; Silva, C.L.M. Ethylene oxide sterilization of medical devices: A review. Am. J. Infect. Control 2007, 35, 574–581. [Google Scholar] [CrossRef]
  33. He, F.; Hu, S.; Liu, R.; Li, X.; Guo, S.; Wang, H.; Tian, G.; Qi, Y.; Wang, T. Decoding the biological toxicity of phenanthrene on intestinal cells of Eisenia fetida: Effects, toxicity pathways and corresponding mechanisms. Sci. Total Environ. 2023, 904, 166903. [Google Scholar] [CrossRef]
  34. Li, Q.; Zhu, X.; Xie, Y.; Liang, J. Antifungal properties and mechanisms of three volatile aldehydes (octanal, nonanal and decanal) on Aspergillus flavus. Grain Oil Sci. Technol. 2021, 4, 131–140. [Google Scholar] [CrossRef]
  35. Aparna, V.; Dileep, K.V.; Mandal, P.K.; Karthe, P.; Sadasivan, C.; Haridas, M. Anti-inflammatory property of n-hexadecanoic acid: Structural evidence and kinetic assessment. Chem. Biol. Drug. Des. 2012, 80, 434–439. [Google Scholar] [CrossRef] [PubMed]
  36. Wang, Y.J.; Liu, B.D.; Wang, X.; Fan, Y.W. Comparison of constituents and antioxidant activity of above-ground and underground parts of Dryopteris crassirhizoma Nakai based on HS-SPME-GC-MS and UPLC/Q-TOF-MS. Molecules 2022, 7, 4991. [Google Scholar] [CrossRef] [PubMed]
  37. Xiao, J.B. Dietary flavonoid aglycones and their glycosides: Which show better biological significance? Crit. Rev. Food Sci. 2017, 57, 1874–1905. [Google Scholar] [CrossRef] [PubMed]
Molecules 29 01142 g001
Figure 1. Total flavonoid content of different parts from M. struthiopteris. All data are presented as the mean ± SD. Error bars represent standard deviation and three replicates for each treatment. An unpaired two-tailed t-test was performed. *** p < 0.001.
Figure 1. Total flavonoid content of different parts from M. struthiopteris. All data are presented as the mean ± SD. Error bars represent standard deviation and three replicates for each treatment. An unpaired two-tailed t-test was performed. *** p < 0.001.
Molecules 29 01142 g001
Molecules 29 01142 g002
Figure 2. DPPH radical scavenging activities of the extracts from six parts of M. struthiopteris: (A) adventitious root, (B) trophophyll, (C) sporophyll, (D) rhizome, (E) crozier, (F) petiole. (red lines and black dots showsed the tendency of different concentrations of extracts to scavenge DPPH radicals).
Figure 2. DPPH radical scavenging activities of the extracts from six parts of M. struthiopteris: (A) adventitious root, (B) trophophyll, (C) sporophyll, (D) rhizome, (E) crozier, (F) petiole. (red lines and black dots showsed the tendency of different concentrations of extracts to scavenge DPPH radicals).
Molecules 29 01142 g002
Molecules 29 01142 g003
Figure 3. ABTS radical scavenging activities of the extracts from six parts of M. struthiopteris: (A) adventitious root, (B) trophophyll, (C) sporophyll, (D) rhizome, (E) crozier, (F) petiole. (red lines and black dots showsed the tendency of different concentrations of extracts to scavenge ABTS radicals).
Figure 3. ABTS radical scavenging activities of the extracts from six parts of M. struthiopteris: (A) adventitious root, (B) trophophyll, (C) sporophyll, (D) rhizome, (E) crozier, (F) petiole. (red lines and black dots showsed the tendency of different concentrations of extracts to scavenge ABTS radicals).
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Molecules 29 01142 g004
Figure 4. AChE inhibitory percentages (%) of the extracts from six parts of M. struthiopteris (adventitious root, trophophyll, sporophyll, rhizome, crozier and petiole).
Figure 4. AChE inhibitory percentages (%) of the extracts from six parts of M. struthiopteris (adventitious root, trophophyll, sporophyll, rhizome, crozier and petiole).
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Molecules 29 01142 g005
Figure 5. Volatile components with area percentage greater than 3% of six parts of M. struthiopteris (adventitious root, trophophyll, sporophyll, rhizome, crozier and petiole). The compounds (Numbers 1–35) were listed in Table 1.
Figure 5. Volatile components with area percentage greater than 3% of six parts of M. struthiopteris (adventitious root, trophophyll, sporophyll, rhizome, crozier and petiole). The compounds (Numbers 1–35) were listed in Table 1.
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Molecules 29 01142 g006
Figure 6. Comparative Analysis of volatile components of different parts of M. struthiopteris. (A): Correlation analysis of volatile components; (B): The distribution of main volatile components.
Figure 6. Comparative Analysis of volatile components of different parts of M. struthiopteris. (A): Correlation analysis of volatile components; (B): The distribution of main volatile components.
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Molecules 29 01142 g007
Figure 7. Distribution characteristics of volatile components from six parts of M. struthiopteris (adventitious root, trophophyll, sporophyll, rhizome, crozier and petiole).
Figure 7. Distribution characteristics of volatile components from six parts of M. struthiopteris (adventitious root, trophophyll, sporophyll, rhizome, crozier and petiole).
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Molecules 29 01142 g008
Figure 8. Different parts from M. struthiopteris.
Figure 8. Different parts from M. struthiopteris.
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Table 1. Compounds of M. struthiopteris with area percentage greater than 3%.
Table 1. Compounds of M. struthiopteris with area percentage greater than 3%.
No.TimeCompoundTypeCompound
Formula		SporophyllRhizomePetioleAdventitious
Root		TrophophyllCrozier
10.797Ethylene oxideEthersC2H4O2.4792.884-2.2011.0634.022
23.354HexanalAldehydesC6H12O0.123.0030.6190.322--
35.516HeptanalAldehydesC7HO0.207-----
48.5OctanalAldehydesC8H16O0.24---0.354-
510.91-pentanolAlcoholsC5H12O-3.2981.440.159--
612.216CyclohexanolAlcoholsC6H12O3.785-----
712.249NonanalAldehydesC9H18O----4.058-
812.573TolueneBenzeneC7H8----3.0813.081
914.4Acetic acidAcidsCH3COOH0.517---1.3273.121
1014.51-Octen-3-olAlcoholsC8H16O-3.9360.8620.496--
1114.8FurfuralAldehydesC5H4O25.26611.4423.8837.17513.36913.621
1216.178DecanalAldehydesC10H20O----2.591-
1318.92-Furancarboxaldehyde, 5-methyl-AldehydesC6H6O23.883.6910.9543.3053.1827.493
1422.33DocosaneHydrocarbonC22H46---4.638--
1524.597Naphthalene, 1,2-dihydro-1,1,6-trimethyl-HydrocarbonC13H163.4910.404-1.1794.884-
1629.56Heptanoic acidAcidsC7H14O2-5.8570.6441.664-2.179
1730.588Butanoic acid, anhydrideAcidsC8H14O3-3.507----
1830.602Butanoic acid, butyl esterAcidsC8H16O2--3.888---
1930.607IsophytolAlcoholsC20H40O---5.7291.969-
2032.383-Buten-2-one, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-KetenesC13H20O1.37---3.88-
2134.374Benzene, 1,4-diethyl-2,3,5,6-tetramethyl-BenzeneC14H223.002-----
2234.393Benzene, 1,4-dimethyl-2,5-bis(1-methylethyl)-BenzeneC14H22----4.986-
2336.812PentadecanalAldehydesC15H30O-----4.721
2437.92-Pentadecanone, 6,10,14-trimethyl-KetenesC18H36O2.5920.829-0.8130.5043.769
2538.945PhenanthreneHydrocarbonC14H10--3.321---
2639.8351,2-Benzenedicarboxylic acid, bis(2-methylpropyl) esterAcidsC16H22O4---4.2513.136-
2740.2Phthalic acidAcidsC8H6O43.8536.69513.151.245-2.679
2840.4121,2-Benzenedicarboxylic acid, decyl octyl esterAcidsC26H42O4--7.934---
2940.9832,2-Dichloroethyl methyl etherEthersC3H6Cl2O--3.025---
3041.126n-Hexadecanoic acidAcidsC16H32O2-4.162----
3141.4931,6-Dideoxy-l-mannitolAlcoholsC6H14O4-3.753----
3241.54512-Crown-4EthersC8H16O411.753---1.904-
3341.936Tetradecanoic acidAcidsC14H28O23.241-----
3442.331Pentaethylene glycolAlcoholsC10H22O6--5.139---
3543.0933,6,9-Trioxa-2-silaundecane, 2,2-dimethyl-HydrocarbonC9H22O3Si--3.871---
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Wang, X.; Guo, J.; Zang, S.; Liu, B.; Wu, Y. Comparison of Flavonoid Content, Antioxidant Potential, Acetylcholinesterase Inhibition Activity and Volatile Components Based on HS-SPME-GC-MS of Different Parts from Matteuccia struthiopteris (L.) Todaro. Molecules 2024, 29, 1142. https://doi.org/10.3390/molecules29051142

AMA Style

Wang X, Guo J, Zang S, Liu B, Wu Y. Comparison of Flavonoid Content, Antioxidant Potential, Acetylcholinesterase Inhibition Activity and Volatile Components Based on HS-SPME-GC-MS of Different Parts from Matteuccia struthiopteris (L.) Todaro. Molecules. 2024; 29(5):1142. https://doi.org/10.3390/molecules29051142

Chicago/Turabian Style

Wang, Xin, Jiatao Guo, Siqi Zang, Baodong Liu, and Yuhuan Wu. 2024. "Comparison of Flavonoid Content, Antioxidant Potential, Acetylcholinesterase Inhibition Activity and Volatile Components Based on HS-SPME-GC-MS of Different Parts from Matteuccia struthiopteris (L.) Todaro" Molecules 29, no. 5: 1142. https://doi.org/10.3390/molecules29051142

APA Style

Wang, X., Guo, J., Zang, S., Liu, B., & Wu, Y. (2024). Comparison of Flavonoid Content, Antioxidant Potential, Acetylcholinesterase Inhibition Activity and Volatile Components Based on HS-SPME-GC-MS of Different Parts from Matteuccia struthiopteris (L.) Todaro. Molecules, 29(5), 1142. https://doi.org/10.3390/molecules29051142

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