Extraction Techniques and Analytical Methods for Isolation and Characterization of Lignans
Abstract
:1. Introduction
2. Sample Preparation
3. Extraction
4. Solvents
5. Methods
6. Artifacts
7. Isolation and Purification
8. Qualitative and Quantitative Analysis
8.1. Thin Layer Chromatography (TLC)
8.2. High-Performance Liquid Chromatography (HPLC)
8.3. Liquid Chromatography Mass Spectrometry
8.4. Gas Chromatography Mass Spectrometry
9. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
- Rodriguez-Garcia, C.; Sanchez-Quesada, C.; Toledo, E.; Delgado-Rodriguez, M.; Gaforio, J.J. Naturally Lignan-Rich Foods: A Dietary Tool for Health Promotion? Molecules 2019, 24, 917. [Google Scholar] [CrossRef] [PubMed]
- Willfor, S.M.; Smeds, A.I.; Holmbom, B.R. Chromatographic analysis of lignans. J. Chromatogr. A 2006, 1112, 64–77. [Google Scholar] [CrossRef] [PubMed]
- Ward, R.S. Recent Advances in the Chemistry of Lignans. In Studies in Natural Products Chemistry; Attaur, R., Ed.; Elsevier: Amsterdam, The Netherlands, 2000; Volume 24, pp. 739–798. [Google Scholar]
- Ferrer, J.L.; Austin, M.B.; Stewart, C., Jr.; Noel, J.P. Structure and function of enzymes involved in the biosynthesis of phenylpropanoids. Plant Physiol. Biochem. 2008, 46, 356–370. [Google Scholar] [CrossRef] [PubMed]
- Kato, M.J.; Chu, A.; Davin, L.B.; Lewis, N.G. Biosynthesis of antioxidant lignans in Sesamum indicum seeds. Phytochemistry 1998, 47, 583–591. [Google Scholar] [CrossRef]
- Lewis, N.G.; Davin, L.B.; Sarkanen, S. Lignin and Lignan Biosynthesis: Distinctions and Reconciliations. In Lignin and Lignan Biosynthesis; ACS Symposium Series; American Chemical Society: Washington, DC, USA, 1998; Volume 697, pp. 1–27. [Google Scholar]
- Nakatsubo, T.; Mizutani, M.; Suzuki, S.; Hattori, T.; Umezawa, T. Characterization of Arabidopsis thaliana pinoresinol reductase, a new type of enzyme involved in lignan biosynthesis. J. Biol. Chem. 2008, 283, 15550–15557. [Google Scholar] [CrossRef]
- Noguchi, A.; Fukui, Y.; Iuchi-Okada, A.; Kakutani, S.; Satake, H.; Iwashita, T.; Nakao, M.; Umezawa, T.; Ono, E. Sequential glucosylation of a furofuran lignan, (+)-sesaminol, by Sesamum indicum UGT71A9 and UGT94D1 glucosyltransferases. Plant J. 2008, 54, 415–427. [Google Scholar] [CrossRef]
- Ono, E.; Nakai, M.; Fukui, Y.; Tomimori, N.; Fukuchi-Mizutani, M.; Saito, M.; Satake, H.; Tanaka, T.; Katsuta, M.; Umezawa, T.; et al. Formation of two methylenedioxy bridges by a Sesamum CYP81Q protein yielding a furofuran lignan, (+)-sesamin. Proc. Natl. Acad. Sci. USA 2006, 103, 10116–10121. [Google Scholar] [CrossRef]
- Umezawa, T. Diversity in lignan biosynthesis. Phytochem. Rev. 2003, 2, 371–390. [Google Scholar] [CrossRef]
- Dewick, P.M. Medicinal Natural Products: A Biosynthetic Approach; Wiley: Chichester, UK, 2012. [Google Scholar]
- Zalesak, F.; Bon, D.J.D.; Pospisil, J. Lignans and Neolignans: Plant secondary metabolites as a reservoir of biologically active substances. Pharm. Res 2019, 146, 104284. [Google Scholar] [CrossRef]
- Adlercreutz, H. Lignans and Human Health. Crit. Rev. Clin. Lab. Sci. 2007, 44, 483–525. [Google Scholar] [CrossRef]
- Flower, G.; Fritz, H.; Balneaves, L.G.; Verma, S.; Skidmore, B.; Fernandes, R.; Kennedy, D.; Cooley, K.; Wong, R.; Sagar, S.; et al. Flax and Breast Cancer:A Systematic Review. Integr. Cancer Ther. 2014, 13, 181–192. [Google Scholar] [CrossRef] [PubMed]
- DeLuca, J.A.A.; Garcia-Villatoro, E.L.; Allred, C.D. Flaxseed Bioactive Compounds and Colorectal Cancer Prevention. Curr. Oncol. Rep. 2018, 20, 59. [Google Scholar] [CrossRef] [PubMed]
- Shabgah, A.G.; Suksatan, W.; Achmad, M.H.; Bokov, D.O.; Abdelbasset, W.K.; Ezzatifar, F.; Hemmati, S.; Mohammadi, H.; Soleimani, D.; Jadidi-Niaragh, F.; et al. Arctigenin, an anti-tumor agent; a cutting-edge topic and up-to-the-minute approach in cancer treatment. Eur. J. Pharmacol. 2021, 909, 174419. [Google Scholar] [CrossRef] [PubMed]
- Paul, S.; Patra, D.; Kundu, R. Lignan enriched fraction (LRF) of Phyllanthus amarus promotes apoptotic cell death in human cervical cancer cells in vitro. Sci. Rep. 2019, 9, 14950. [Google Scholar] [CrossRef] [PubMed]
- Hwang, D.; Shin, S.Y.; Lee, Y.; Hyun, J.; Yong, Y.; Park, J.C.; Lee, Y.H.; Lim, Y. A compound isolated from Schisandra chinensis induces apoptosis. Bioorg. Med. Chem. Lett. 2011, 21, 6054–6057. [Google Scholar] [CrossRef]
- Shen, L.; Zhang, F.; Huang, R.; Yan, J.; Shen, B. Honokiol inhibits bladder cancer cell invasion through repressing SRC-3 expression and epithelial-mesenchymal transition. Oncol. Lett. 2017, 14, 4294–4300. [Google Scholar] [CrossRef]
- Zidorn, C. Guidelines for consistent characterisation and documentation of plant source materials for studies in phytochemistry and phytopharmacology. Phytochemistry 2017, 139, 56–59. [Google Scholar] [CrossRef]
- Holmbom, B.; Willfoer, S.; Hemming, J.; Pietarinen, S.; Nisula, L.; Eklund, P.; Sjoeholm, R. Knots in Trees: A Rich Source of Bioactive Polyphenols. In Materials, Chemicals, and Energy from Forest Biomass; ACS Symposium Series; American Chemical Society: Washington, DC, USA, 2007; pp. 350–362. [Google Scholar]
- Mansikkala, T.; Patanen, M.; Kärkönen, A.; Korpinen, R.; Pranovich, A.; Ohigashi, T.; Swaraj, S.; Seitsonen, J.; Ruokolainen, J.; Huttula, M.; et al. Lignans in Knotwood of Norway Spruce: Localisation with Soft X-ray Microscopy and Scanning Transmission Electron Microscopy with Energy Dispersive X-ray Spectroscopy. Molecules 2020, 25, 2997. [Google Scholar] [CrossRef]
- Hosseinian, F.S.; Beta, T. Patented techniques for the extraction and isolation of secoisolari-ciresinol diglucoside from flaxseed. Recent Pat. Food Nutr. Agric. 2009, 1, 25–31. [Google Scholar] [CrossRef]
- Khoddami, A.; Wilkes, M.A.; Roberts, T.H. Techniques for analysis of plant phenolic compounds. Molecules 2013, 18, 2328–2375. [Google Scholar] [CrossRef]
- Liu, J.; Cai, Y.Z.; Wong, R.N.; Lee, C.K.; Tang, S.C.; Sze, S.C.; Tong, Y.; Zhang, Y. Comparative analysis of caffeoylquinic acids and lignans in roots and seeds among various burdock (Arctium lappa) genotypes with high antioxidant activity. J. Agric. Food Chem. 2012, 60, 4067–4075. [Google Scholar] [CrossRef] [PubMed]
- Mahendra Kumar, C.; Singh, S.A. Bioactive lignans from sesame (Sesamum indicum L.): Evaluation of their antioxidant and antibacterial effects for food applications. J. Food Sci. Technol. 2015, 52, 2934–2941. [Google Scholar] [CrossRef] [PubMed]
- Gerstenmeyer, E.; Reimer, S.; Berghofer, E.; Schwartz, H.; Sontag, G. Effect of thermal heating on some lignans in flax seeds, sesame seeds and rye. Food Chem. 2013, 138, 1847–1855. [Google Scholar] [CrossRef] [PubMed]
- Hu, J.; Shi, Y.; Yang, B.; Dong, Z.; Si, X.; Qin, K. Changes in chemical components and antitumor activity during the heating process of Fructus Arctii. Pharm. Biol. 2019, 57, 363–368. [Google Scholar] [CrossRef]
- Qin, K.; Liu, Q.; Cai, H.; Cao, G.; Lu, T.; Shen, B.; Shu, Y.; Cai, B. Chemical analysis of raw and processed Fructus arctii by high-performance liquid chromatography/diode array detection-electrospray ionization-mass spectrometry. Pharm. Mag. 2014, 10, 541–546. [Google Scholar] [CrossRef]
- Chen, Y.; Lin, H.; Lin, M.; Zheng, Y.; Chen, J. Effect of roasting and in vitro digestion on phenolic profiles and antioxidant activity of water-soluble extracts from sesame. Food Chem. Toxicol. 2020, 139, 111239. [Google Scholar] [CrossRef]
- Kawamura, F.; Miyachi, M.; Kawai, S.; Ohashi, H. Photodiscoloration of western hemlock (Tsuga heterophylla) sapwood III Early stage of photodiscoloration reaction with lignans. J. Wood Sci. 1998, 44, 47–55. [Google Scholar] [CrossRef]
- Yuan, J.-P.; Li, X.; Xu, S.-P.; Wang, J.-H.; Liu, X. Hydrolysis Kinetics of Secoisolariciresinol Diglucoside Oligomers from Flaxseed. J. Agric. Food Chem. 2008, 56, 10041–10047. [Google Scholar] [CrossRef]
- Renouard, S.; Hano, C.; Corbin, C.; Fliniaux, O.; Lopez, T.; Montguillon, J.; Barakzoy, E.; Mesnard, F.; Lamblin, F.; Lainé, E. Cellulase-assisted release of secoisolariciresinol from extracts of flax (Linum usitatissimum) hulls and whole seeds. Food Chem. 2010, 122, 679–687. [Google Scholar] [CrossRef]
- Sicilia, T.; Niemeyer, H.B.; Honig, D.M.; Metzler, M. Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds. J. Agric. Food Chem. 2003, 51, 1181–1188. [Google Scholar] [CrossRef]
- Pilkington, L.I. Lignans: A Chemometric Analysis. Molecules 2018, 23, 1666. [Google Scholar] [CrossRef] [PubMed]
- Grougnet, R.; Magiatis, P.; Laborie, H.; Lazarou, D.; Papadopoulos, A.; Skaltsounis, A.L. Sesamolinol glucoside, disaminyl ether, and other lignans from sesame seeds. J. Agric. Food Chem. 2012, 60, 108–111. [Google Scholar] [CrossRef]
- Yang, F.; Yang, L.; Wang, W.; Liu, Y.; Zhao, C.; Zu, Y. Enrichment and purification of syringin, eleutheroside E and isofraxidin from Acanthopanax senticosus by macroporous resin. Int. J. Mol. Sci. 2012, 13, 8970–8986. [Google Scholar] [CrossRef]
- Wang, Z.; Zhang, L.; Sun, Y. Semipreparative separation and determination of eleutheroside E in Acanthopanax giraldii Harms by high-performance liquid chromatography. J. Chromatogr. Sci. 2005, 43, 249–252. [Google Scholar] [CrossRef]
- Benković, E.T.; Grohar, T.; Žigon, D.; Švajger, U.; Janeš, D.; Kreft, S.; Štrukelj, B. Chemical composition of the silver fir (Abies alba) bark extract Abigenol® and its antioxidant activity. Ind. Crops Prod. 2014, 52, 23–28. [Google Scholar] [CrossRef]
- Jahagirdar, A.; Usharani, D.; Srinivasan, M.; Rajasekharan, R. Sesaminol diglucoside, a water-soluble lignan from sesame seeds induces brown fat thermogenesis in mice. Biochem. Biophys. Res. Commun. 2018, 507, 155–160. [Google Scholar] [CrossRef] [PubMed]
- Fang, W.; Hemming, J.; Reunanen, M.; Eklund, P.; Pineiro, E.C.; Poljanšek, I.; Oven, P.; Willför, S. Evaluation of selective extraction methods for recovery of polyphenols from pine. Holzforschung 2013, 67, 843–851. [Google Scholar] [CrossRef]
- Liu, H.; Zhang, Y.; Sun, Y.; Wang, X.; Zhai, Y.; Sun, Y.; Sun, S.; Yu, A.; Zhang, H.; Wang, Y. Determination of the major constituents in fruit of Arctium lappa L. by matrix solid-phase dispersion extraction coupled with HPLC separation and fluorescence detection. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2010, 878, 2707–2711. [Google Scholar] [CrossRef]
- Su, S.; Wink, M. Natural lignans from Arctium lappa as antiaging agents in Caenorhabditis elegans. Phytochemistry 2015, 117, 340–350. [Google Scholar] [CrossRef]
- Tokar, M.; Klimek, B. The content of lignan glycosides in Forsythia flowers and leaves. Acta Pol. Pharm. 2004, 61, 273–278. [Google Scholar]
- Kuo, P.C.; Chen, G.F.; Yang, M.L.; Lin, Y.H.; Peng, C.C. Chemical constituents from the fruits of Forsythia suspensa and their antimicrobial activity. Biomed. Res. Int. 2014, 2014, 304830. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Li, Y.-L.; Yang, X.-W.; Zhang, W.-D. Stilbenes, lignans, and phenols from Abies chensiensis. Biochem. Syst. Ecol. 2008, 36, 932–934. [Google Scholar] [CrossRef]
- Li, Y.L.; Gao, Y.X.; Jin, H.Z.; Shan, L.; Liang, X.S.; Xu, X.K.; Yang, X.W.; Wang, N.; Steinmetz, A.; Chen, Z.; et al. Chemical constituents of Abies nukiangensis. Phytochemistry 2014, 106, 116–123. [Google Scholar] [CrossRef]
- Zhang, H.; Gao, Y.; Zhang, J.; Wang, K.; Jin, T.; Wang, H.; Ruan, K.; Wu, F.; Xu, Z. The effect of total lignans from Fructus Arctii on Streptozotocin-induced diabetic retinopathy in Wistar rats. J. Ethnopharmacol. 2020, 255, 112773. [Google Scholar] [CrossRef]
- Lu, H.; Sun, Z.; Shan, H.; Song, J. Microwave-Assisted Extraction and Purification of Arctiin and Arctigenin from Fructus Arctii by High-Speed Countercurrent Chromatography. J. Chromatogr. Sci. 2016, 54, 472–478. [Google Scholar] [CrossRef] [PubMed]
- He, J.; Huang, X.Y.; Yang, Y.N.; Feng, Z.M.; Jiang, J.S.; Zhang, P.C. Two new compounds from the fruits of Arctium lappa. J. Asian Nat. Prod. Res. 2016, 18, 423–428. [Google Scholar] [CrossRef] [PubMed]
- Yang, Y.N.; Huang, X.Y.; Feng, Z.M.; Jiang, J.S.; Zhang, P.C. New Butyrolactone Type Lignans from Arctii Fructus and Their Anti-inflammatory Activities. J. Agric. Food Chem. 2015, 63, 7958–7966. [Google Scholar] [CrossRef]
- Park, S.Y.; Hong, S.S.; Han, X.H.; Hwang, J.S.; Lee, D.; Ro, J.S.; Hwang, B.Y. Lignans from Arctium lappa and their inhibition of LPS-induced nitric oxide production. Chem. Pharm. Bull. 2007, 55, 150–152. [Google Scholar] [CrossRef]
- Kuehnl, S.; Schroecksnadel, S.; Temml, V.; Gostner, J.M.; Schennach, H.; Schuster, D.; Schwaiger, S.; Rollinger, J.M.; Fuchs, D.; Stuppner, H. Lignans from Carthamus tinctorius suppress tryptophan breakdown via indoleamine 2,3-dioxygenase. Phytomedicine 2013, 20, 1190–1195. [Google Scholar] [CrossRef]
- Lee, S.; Ban, H.S.; Kim, Y.P.; Kim, B.K.; Cho, S.H.; Ohuchi, K.; Shin, K.H. Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin E2 production. Phytother. Res. 2005, 19, 103–106. [Google Scholar] [CrossRef]
- Jin, L.; Schmiech, M.; El Gaafary, M.; Zhang, X.; Syrovets, T.; Simmet, T. A comparative study on root and bark extracts of Eleutherococcus senticosus and their effects on human macrophages. Phytomedicine 2020, 68, 153181. [Google Scholar] [CrossRef] [PubMed]
- Li, T.; Ferns, K.; Yan, Z.Q.; Yin, S.Y.; Kou, J.J.; Li, D.; Zeng, Z.; Yin, L.; Wang, X.; Bao, H.X.; et al. Acanthopanax senticosus: Photochemistry and Anticancer Potential. Am. J. Chin. Med. 2016, 44, 1543–1558. [Google Scholar] [CrossRef] [PubMed]
- Lee, D.Y.; Seo, K.H.; Jeong, R.H.; Lee, S.M.; Kim, G.S.; Noh, H.J.; Kim, S.Y.; Kim, G.W.; Kim, J.Y.; Baek, N.I. Anti-inflammatory lignans from the fruits of Acanthopanax sessiliflorus. Molecules 2012, 18, 41–49. [Google Scholar] [CrossRef] [PubMed]
- Michalak, B.; Filipek, A.; Chomicki, P.; Pyza, M.; Wozniak, M.; Zyzynska-Granica, B.; Piwowarski, J.P.; Kicel, A.; Olszewska, M.A.; Kiss, A.K. Lignans From Forsythia x Intermedia Leaves and Flowers Attenuate the Pro-inflammatory Function of Leukocytes and Their Interaction with Endothelial Cells. Front. Pharm. 2018, 9, 401. [Google Scholar] [CrossRef]
- Lee, Y.G.; Jang, S.A.; Seo, K.H.; Gwag, J.E.; Kim, H.G.; Ko, J.H.; Ji, S.A.; Kang, S.C.; Lee, D.Y.; Baek, N.I. New Lignans from the Flower of Forsythia koreana and Their Suppression Effect on VCAM-1 Expression in MOVAS Cells. Chem. Biodivers. 2018, 15, e1800026. [Google Scholar] [CrossRef]
- Lim, H.; Lee, J.G.; Lee, S.H.; Kim, Y.S.; Kim, H.P. Anti-inflammatory activity of phylligenin, a lignan from the fruits of Forsythia koreana, and its cellular mechanism of action. J. Ethnopharmacol. 2008, 118, 113–117. [Google Scholar] [CrossRef]
- Kang, H.S.; Lee, J.Y.; Kim, C.J. Anti-inflammatory activity of arctigenin from Forsythiae Fructus. J. Ethnopharmacol. 2008, 116, 305–312. [Google Scholar] [CrossRef]
- Kim, C.Y.; Ahn, M.J.; Kim, J. A preparative isolation and purification of arctigenin and matairesinol from Forsythia koreana by centrifugal partition chromatography. J. Sep. Sci. 2006, 29, 656–659. [Google Scholar] [CrossRef]
- Chang, M.J.; Hung, T.M.; Min, B.S.; Kim, J.C.; Woo, M.H.; Choi, J.S.; Lee, H.K.; Bae, K. Lignans from the Fruits of Forsythia suspensa (Thunb.) Vahl Protect High-Density Lipoprotein during Oxidative Stress. Biosci. Biotechnol. Biochem. 2008, 72, 2750–2755. [Google Scholar] [CrossRef]
- Guo, H.; Liu, A.H.; Ye, M.; Yang, M.; Guo, D.A. Characterization of phenolic compounds in the fruits of Forsythia suspensa by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2007, 21, 715–729. [Google Scholar] [CrossRef]
- Li, C.; Dai, Y.; Duan, Y.-H.; Liu, M.-L.; Yao, X.-S. A new lignan glycoside from Forsythia suspensa. Chin. J. Nat. Med. 2014, 12, 697–699. [Google Scholar] [CrossRef]
- Kuo, P.C.; Hung, H.Y.; Nian, C.W.; Hwang, T.L.; Cheng, J.C.; Kuo, D.H.; Lee, E.J.; Tai, S.H.; Wu, T.S. Chemical Constituents and Anti-inflammatory Principles from the Fruits of Forsythia suspensa. J. Nat. Prod. 2017, 80, 1055–1064. [Google Scholar] [CrossRef] [PubMed]
- Liang, J.; Gong, F.Q.; Sun, H.M. Simultaneous Separation of Eight Lignans in Forsythia suspensa by beta-Cyclodextrin-Modified Capillary Zone Electrophoresis. Molecules 2018, 23, 514. [Google Scholar] [CrossRef] [PubMed]
- Huh, J.; Song, J.H.; Kim, S.R.; Cho, H.M.; Ko, H.J.; Yang, H.; Sung, S.H. Lignan Dimers from Forsythia viridissima Roots and Their Antiviral Effects. J. Nat. Prod. 2019, 82, 232–238. [Google Scholar] [CrossRef]
- Shang, N.; Guerrero-Analco, J.A.; Musallam, L.; Saleem, A.; Muhammad, A.; Walshe-Roussel, B.; Cuerrier, A.; Arnason, J.T.; Haddad, P.S. Adipogenic constituents from the bark of Larix laricina du Roi (K. Koch; Pinaceae), an important medicinal plant used traditionally by the Cree of Eeyou Istchee (Quebec, Canada) for the treatment of type 2 diabetes symptoms. J. Ethnopharmacol. 2012, 141, 1051–1057. [Google Scholar] [CrossRef] [PubMed]
- Waszkowiak, K.; Gliszczynska-Swiglo, A.; Barthet, V.; Skrety, J. Effect of Extraction Method on the Phenolic and Cyanogenic Glucoside Profile of Flaxseed Extracts and their Antioxidant Capacity. J. Am. Oil Chem. Soc. 2015, 92, 1609–1619. [Google Scholar] [CrossRef]
- Beejmohun, V.; Fliniaux, O.; Grand, E.; Lamblin, F.; Bensaddek, L.; Christen, P.; Kovensky, J.; Fliniaux, M.A.; Mesnard, F. Microwave-assisted extraction of the main phenolic compounds in flaxseed. Phytochem. Anal. 2007, 18, 275–282. [Google Scholar] [CrossRef]
- Fritsche, J.; Angoelal, R.; Dachtler, M. On-line liquid-chromatography-nuclear magnetic resonance spectroscopy-mass spectrometry coupling for the separation and characterization of secoisolariciresinol diglucoside isomers in flaxseed. J. Chromatogr. A 2002, 972, 195–203. [Google Scholar] [CrossRef]
- Degenhardt, A.; Habben, S.; Winterhalter, P. Isolation of the lignan secoisolariciresinol diglucoside from flaxseed (Linum usitatissimum L.) by high-speed counter-current chromatography. J. Chromatogr. A 2002, 943, 299–302. [Google Scholar] [CrossRef]
- Li, X.; Yuan, J.P.; Xu, S.P.; Wang, J.H.; Liu, X. Separation and determination of secoisolariciresinol diglucoside oligomers and their hydrolysates in the flaxseed extract by high-performance liquid chromatography. J. Chromatogr. A 2008, 1185, 223–232. [Google Scholar] [CrossRef]
- Corbin, C.; Fidel, T.; Leclerc, E.A.; Barakzoy, E.; Sagot, N.; Falguieres, A.; Renouard, S.; Blondeau, J.P.; Ferroud, C.; Doussot, J.; et al. Development and validation of an efficient ultrasound assisted extraction of phenolic compounds from flax (Linum usitatissimum L.) seeds. Ultrason. Sonochem. 2015, 26, 176–185. [Google Scholar] [CrossRef] [PubMed]
- Hassan Mekky, R.; Abdel-Sattar, E.; Segura-Carretero, A.; Contreras, M.d.M. A comparative study on the metabolites profiling of linseed cakes from Egyptian cultivars and antioxidant activity applying mass spectrometry-based analysis and chemometrics. Food Chem. 2022, 395, 133524. [Google Scholar] [CrossRef] [PubMed]
- Lee, D.H.; Kwon, S.Y.; Woo, M.H.; Lee, J.-H.; Son, K.H. Phytochemical Studies on Magnoliae Flos (I) Isolation of Lignans from the Flower Buds of Magnolia biondii. Nat. Prod. Sci. 2013, 19, 160–165. [Google Scholar]
- Nguyen, T.T.M.; Lee, H.S.; Nguyen, T.T.; Ngo, T.Q.M.; Jun, C.D.; Min, B.S.; Kim, J.A. Four New Lignans and IL-2 Inhibitors from Magnoliae Flos. Chem. Pharm. Bull. 2017, 65, 840–847. [Google Scholar] [CrossRef] [PubMed]
- Aspé, E.; Fernández, K. The effect of different extraction techniques on extraction yield, total phenolic, and anti-radical capacity of extracts from Pinus radiata Bark. Ind. Crops Prod. 2011, 34, 838–844. [Google Scholar] [CrossRef]
- Willför, S.; Hemming, J.; Reunanen, M.; Holmbom, B. Phenolic and Lipophilic Extractives in Scots Pine Knots and Stemwood. Wood Res. Technol. 2003, 57, 359–372. [Google Scholar] [CrossRef]
- Ekman, R.; Willför, S.; Sjöholm, R.; Reunanen, M.; Mäki, J.; Lehtilä, R.; Eckerman, C. Identification of the Lignan Nortrachelogenin in Knot and Branch Heartwood of Scots Pine (Pinus sylvestris L.). Wood Res. Technol. 2002, 56, 253–256. [Google Scholar] [CrossRef]
- Mishra, S.; Aeri, V. Optimization of microwave-assisted extraction conditions for preparing lignan-rich extract from Saraca asoca bark using Box-Behnken design. Pharm. Biol. 2016, 54, 1255–1262. [Google Scholar] [CrossRef]
- Kwon, D.Y.; Kim, D.S.; Yang, H.J.; Park, S. The lignan-rich fractions of Fructus Schisandrae improve insulin sensitivity via the PPAR-gamma pathways in in vitro and in vivo studies. J. Ethnopharmacol. 2011, 135, 455–462. [Google Scholar] [CrossRef]
- Dai, Z.; Xin, H.; Fu, Q.; Hao, H.; Li, Q.; Liu, Q.; Jin, Y. Exploration and optimization of conditions for quantitative analysis of lignans in Schisandra chinensis by an online supercritical fluid extraction with supercritical fluid chromatography system. J. Sep. Sci. 2019, 42, 2444–2454. [Google Scholar] [CrossRef]
- Razgonova, M.; Zakharenko, A.; Pikula, K.; Kim, E.; Chernyshev, V.; Ercisli, S.; Cravotto, G.; Golokhvast, K. Rapid Mass Spectrometric Study of a Supercritical CO(2)-extract from Woody Liana Schisandra chinensis by HPLC-SPD-ESI-MS/MS. Molecules 2020, 25, 2689. [Google Scholar] [CrossRef]
- Zhu, X.; Zhang, X.; Sun, Y.; Su, D.; Sun, Y.; Hu, B.; Zeng, X. Purification and fermentation in vitro of sesaminol triglucoside from sesame cake by human intestinal microbiota. J. Agric. Food Chem. 2013, 61, 1868–1877. [Google Scholar] [CrossRef] [PubMed]
- Kuo, P.C.; Lin, M.C.; Chen, G.F.; Yiu, T.J.; Tzen, J.T. Identification of methanol-soluble compounds in sesame and evaluation of antioxidant potential of its lignans. J. Agric. Food Chem. 2011, 59, 3214–3219. [Google Scholar] [CrossRef] [PubMed]
- Mekky, R.H.; Abdel-Sattar, E.; Segura-Carretero, A.; Contreras, M.D.M. Phenolic Compounds from Sesame Cake and Antioxidant Activity: A New Insight for Agri-Food Residues’ Significance for Sustainable Development. Foods 2019, 8, 432. [Google Scholar] [CrossRef] [PubMed]
- Feng, X.; Su, G.; Ye, Y.; Zhang, R.; Yang, X.; Du, B.; Peng, B.; Tu, P.; Chai, X. Alashinols F and G, two lignans from stem bark of Syringa pinnatifolia. Nat. Prod. Res. 2017, 31, 1555–1560. [Google Scholar] [CrossRef]
- Shao, L.W.; Wang, C.H.; Li, G.Q.; Huang, X.J.; Li, Z.; Wang, G.C. A new lignan from the roots of Syringa pinnatifolia. Nat. Prod. Res. 2014, 28, 1894–1899. [Google Scholar] [CrossRef]
- Wozniak, M.; Michalak, B.; Wyszomierska, J.; Dudek, M.K.; Kiss, A.K. Effects of Phytochemically Characterized Extracts From Syringa vulgaris and Isolated Secoiridoids on Mediators of Inflammation in a Human Neutrophil Model. Front. Pharm. 2018, 9, 349. [Google Scholar] [CrossRef]
- Tiwari, P.; Kaur, M.; Kaur, H. Phytochemical screening and Extraction: A Review. Int. Pharm. Sci. 2011, 1, 98–106. [Google Scholar]
- Lee, S.U.; Ryu, H.W.; Lee, S.; Shin, I.S.; Choi, J.H.; Lee, J.W.; Lee, J.; Kim, M.O.; Lee, H.J.; Ahn, K.S.; et al. Lignans Isolated from Flower Buds of Magnolia fargesii Attenuate Airway Inflammation Induced by Cigarette Smoke in vitro and in vivo. Front. Pharm. 2018, 9, 970. [Google Scholar] [CrossRef]
- Shi, X.; Yang, Y.; Ren, H.; Sun, S.; Mu, L.t.; Chen, X.; Wang, Y.; Zhang, Y.; Wang, L.h.; Sun, C. Identification of multiple components in deep eutectic solvent extract of Acanthopanax senticosus root by ultra-high-performance liquid chromatography with quadrupole orbitrap mass spectrometry. Phytochem. Lett. 2020, 35, 175–185. [Google Scholar] [CrossRef]
- Vinatoru, M. Ultrasonically assisted extraction (UAE) of natural products some guidelines for good practice and reporting. Ultrason. Sonochem. 2015, 25, 94–95. [Google Scholar] [CrossRef] [PubMed]
- Zhang, Q.W.; Lin, L.G.; Ye, W.C. Techniques for extraction and isolation of natural products: A comprehensive review. Chin. Med. 2018, 13, 20. [Google Scholar] [CrossRef]
- Willför, S.; Hemming, J.; Reunanen, M.; Eckerman, C.; Holmbom, B. Lignans and Lipophilic Extractives in Norway Spruce Knots and Stemwood. Wood Res. Technol. 2003, 57, 27–36. [Google Scholar] [CrossRef]
- Willför, S.; Nisula, L.; Hemming, J.; Reunanen, M.; Holmbom, B. Bioactive phenolic substances in industrially important tree species. Part 1: Knots and stemwood of different spruce species. Wood Res. Technol. 2004, 58, 335–344. [Google Scholar] [CrossRef]
- Willför, S.; Nisula, L.; Hemming, J.; Reunanen, M.; Holmbom, B. Bioactive phenolic substances in industrially important tree species. Part 2: Knots and stemwood of fir species. Holzforschung 2004, 58, 650–659. [Google Scholar] [CrossRef]
- Pietarinen, S.P.; Willför, S.M.; Ahotupa, M.O.; Hemming, J.E.; Holmbom, B.R. Knotwood and bark extracts: Strong antioxidants from waste materials. J. Wood Sci. 2006, 52, 436–444. [Google Scholar] [CrossRef]
- Kalyniukova, A.; Holuša, J.; Musiolek, D.; Sedlakova-Kadukova, J.; Płotka-Wasylka, J.; Andruch, V. Application of deep eutectic solvents for separation and determination of bioactive compounds in medicinal plants. Ind. Crops Prod. 2021, 172, 114047. [Google Scholar] [CrossRef]
- Garg, C.; Verma, S.; Satija, S.; Mehta, M.; Dureja, H.; Garg, M. Microwave assisted extraction of bioactive compound phyllanthin from Phyllanthus amarus and optimization using central composite design. Int. J. Pharm. Sci. Res. 2016, 1, 30–35. [Google Scholar]
- Slanina, J.; Glatz, Z. Separation procedures applicable to lignan analysis. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2004, 812, 215–229. [Google Scholar] [CrossRef]
- Eklund, P.C.; Sundell, F.J.; Smeds, A.I.; Sjoholm, R.E. Reactions of the natural lignan hydroxymatairesinol in basic and acidic nucleophilic media: Formation and reactivity of a quinone methide intermediate. Org. Biomol. Chem. 2004, 2, 2229–2235. [Google Scholar] [CrossRef]
- Eklund, P.; Sillanpää, R.; Sjöholm, R. Synthetic transformation of hydroxymatairesinol from Norway spruce (Picea abies) to 7-hydroxysecoisolariciresinol, (+)-lariciresinol and (+)-cyclolariciresinol. J. Chem. Soc. Perkin Trans. 2002, 1, 1906–1910. [Google Scholar] [CrossRef]
- Smeds, A.I.; Eklund, P.C.; Sjöholm, R.E.; Willför, S.M.; Nishibe, S.; Deyama, T.; Holmbom, B.R. Quantification of a broad spectrum of lignans in cereals, oilseeds, and nuts. J. Agric. Food Chem. 2007, 55, 1337–1346. [Google Scholar] [CrossRef]
- Macías-Villamizar, V.; Cuca-Suárez, L. Structural modification of lignan compounds isolated from nectandra species (lauraceaE). J. Chil. Chem. Soc. 2017, 62, 3427–3431. [Google Scholar] [CrossRef]
- Eklund, P.C.; Willför, S.M.; Smeds, A.I.; Sundell, F.J.; Sjöholm, R.E.; Holmbom, B.R. A new lariciresinol-type butyrolactone lignan derived from hydroxymatairesinol and its identification in spruce wood. J. Nat. Prod. 2004, 67, 927–931. [Google Scholar] [CrossRef] [PubMed]
- Wang, P.; Liu, Y.; Chen, T.; Xu, W.; You, J.; Liu, Y.; Li, Y. One-step Separation and Purification of Three Lignans and One Flavonol from Sinopodophyllum emodi by Medium-pressure Liquid Chromatography and High-speed Counter-current Chromatography. Phytochem. Anal. 2013, 24, 603–607. [Google Scholar] [CrossRef]
- Sok, D.E.; Cui, H.S.; Kim, M.R. Isolation and bioactivities of furfuran type lignan compounds from edible plants. Recent Pat. Food Nutr. Agric. 2009, 1, 87–95. [Google Scholar] [CrossRef] [PubMed]
- Schmidt-Traub, H.; Schulte, M.; Seidel-Morgenstern, A. Preparative Chromatography; Wiley: Hoboken, NJ, USA, 2020. [Google Scholar]
- Huang, Q.; Tan, J.B.; Zeng, X.C.; Wang, Y.Q.; Zou, Z.X.; Ouyang, D.S. Lignans and phenolic constituents from Eucommia ulmoides Oliver. Nat. Prod. Res. 2021, 35, 3376–3383. [Google Scholar] [CrossRef]
- Zhang, L.; Wang, X.L.; Wang, B.; Zhang, L.T.; Gao, H.M.; Shen, T.; Lou, H.X.; Ren, D.M.; Wang, X.N. Lignans from Euphorbia hirta L. Nat. Prod. Res. 2022, 36, 26–36. [Google Scholar] [CrossRef]
- Nhung, L.T.H.; Anh, N.T.H.; Tai, B.H.; Kiem, P.V. Isolation of lignans and neolignans from Pouzolzia sanguinea with their cytotoxic activity. Vietnam J. Chem. 2021, 59, 146–152. [Google Scholar]
- Silva, V.C.d.; Bolzani, V.d.S.; Lopes, M.N.; Silva, G.H. Isolation of lignans glycosides from Alibertia sessilis (Vell) K Schum (Rubiaceae) by preparative high-performance liquid chromatography. Eclet. Quim. 2006, 31, 55–58. [Google Scholar] [CrossRef]
- Lee, J.; Yang, H.S.; Jeong, H.; Kim, J.-H.; Yang, H. Targeted Isolation of Lignans from Trachelospermum asiaticum Using Molecular Networking and Hierarchical Clustering Analysis. Biomolecules 2020, 10, 378. [Google Scholar] [CrossRef] [PubMed]
- Benzina, S.; Harquail, J.; Jean, S.; Beauregard, A.P.; Colquhoun, C.D.; Carroll, M.; Bos, A.; Gray, C.A.; Robichaud, G.A. Deoxypodophyllotoxin isolated from Juniperus communis induces apoptosis in breast cancer cells. Anticancer Agents Med. Chem. 2015, 15, 79–88. [Google Scholar] [CrossRef]
- Takahashi, M.; Nishizaki, Y.; Sugimoto, N.; Takeuchi, H.; Nakagawa, K.; Akiyama, H.; Sato, K.; Inoue, K. Determination and purification of sesamin and sesamolin in sesame seed oil unsaponified matter using reversed-phase liquid chromatography coupled with photodiode array and tandem mass spectrometry and high-speed countercurrent chromatography. J. Sep. Sci. 2016, 39, 3898–3905. [Google Scholar] [CrossRef]
- Wang, X.; Lin, Y.; Geng, Y.; Li, F.; Wang, D. Preparative separation and purification of sesamin and sesamolin from sesame seeds by high-speed counter-current chromatography. Cereal Chem. 2009, 86, 23. [Google Scholar] [CrossRef]
- Wagner, H.; Bladt, S. Plant Drug Analysis: A Thin Layer Chromatography Atlas; Springer: Berlin/Heidelberg, Germany, 2009. [Google Scholar]
- Zare, K.; Movafeghi, A.; Mohammadi, S.A.; Asnaashari, S.; Nazemiyeh, H. New Phenolics from Linum mucronatum subsp. orientale. Bioimpacts 2014, 4, 117–122. [Google Scholar] [CrossRef]
- Goels, T.; Eichenauer, E.; Langeder, J.; Hoeller, F.; Sykora, C.; Tahir, A.; Urban, E.; Heiss, E.H.; Saukel, J.; Glasl, S. Norway Spruce Balm: Phytochemical Composition and Ability to Enhance Re-epithelialization In Vitro. Planta Med. 2020, 86, 1080–1088. [Google Scholar] [CrossRef] [PubMed]
- Sobstyl, E.; Szopa, A.; Ekiert, H.; Gnat, S.; Typek, R.; Choma, I.M. Effect directed analysis and TLC screening of Schisandra chinensis fruits. J. Chromatogr. A 2020, 1618, 460942. [Google Scholar] [CrossRef] [PubMed]
- Pi, J.J.; Wu, X.; Rui, W.; Feng, Y.F.; Guo, J. Identification and Fragmentation Mechanisms of Two Kinds of Chemical Compositions in Eucommia ulmoides By UPLC-ESI-Q-TOF-MS/MS. Chem. Nat. Compd. 2016, 52, 144–148. [Google Scholar] [CrossRef]
- Kraushofer, T.; Sontag, G. Determination of matairesinol in flax seed by HPLC with coulometric electrode array detection. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2002, 777, 61–66. [Google Scholar] [CrossRef]
- Li, J.; Wen, J.; Tang, G.; Li, R.; Guo, H.; Weng, W.; Wang, D.; Ji, S. Development of a comprehensive quality control method for the quantitative analysis of volatiles and lignans in Magnolia biondii Pamp. by near infrared spectroscopy. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2020, 230, 118080. [Google Scholar] [CrossRef]
- Zhang, Q.; Zhu, W.; Guan, H.; Liu, H.; Yang, W.; Wang, H.; Cai, D. Development of a matrix solid-phase dispersion extraction combined with high-performance liquid chromatography for determination of five lignans from the Schisandra chinensis. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2016, 1011, 151–157. [Google Scholar] [CrossRef] [PubMed]
- Sobstyl, E.; Szopa, A.; Dziurka, M.; Ekiert, H.; Nikolaichuk, H.; Choma, I.M. Schisandra rubriflora Fruit and Leaves as Promising New Materials of High Biological Potential: Lignan Profiling and Effect-Directed Analysis. Molecules 2022, 27, 2116. [Google Scholar] [CrossRef]
- Liu, H.; Zhang, J.; Li, X.; Qi, Y.; Peng, Y.; Zhang, B.; Xiao, P. Chemical analysis of twelve lignans in the fruit of Schisandra sphenanthera by HPLC–PAD-MS. Phytomedicine 2012, 19, 1234–1241. [Google Scholar] [CrossRef] [PubMed]
- Shi, L.; Zheng, L.; Xiang, Y.; Liu, R.; Chang, M.; Jin, Q.; Wang, X. A Rapid Method for Simultaneous Analysis of Lignan and γ-Tocopherol in Sesame Oil by Using Normal-Phase Liquid Chromatography. J. Am. Oil Chem. Soc. 2018, 95, 13–19. [Google Scholar] [CrossRef]
- Zhao, L.; Tian, X.; Fan, P.C.; Zhan, Y.J.; Shen, D.W.; Jin, Y. Separation, determination and identification of the diastereoisomers of podophyllotoxin and its esters by high-performance liquid chromatography/tandem mass spectrometry. J. Chromatogr. A 2008, 1210, 168–177. [Google Scholar] [CrossRef]
- Avula, B.; Wang, Y.-H.; Moraes, R.M.; Khan, I.A. Rapid analysis of lignans from leaves of Podophyllum peltatum L. samples using UPLC-UV-MS. Biomed. Chromatogr. 2011, 25, 1230–1236. [Google Scholar] [CrossRef]
- Lu, L.W.; Le, Z.; Hou, Z.L.; Jie, W.; Yao, G.D.; Lin, B.; Huang, X.X.; Song, S.J. Chiral-phase resolution of sesquilignans from raspberries (Rubus idaeus L.) and their neuroprotective effects. Fitoterapia 2020, 146, 104655. [Google Scholar] [CrossRef]
- Dar, A.A.; Arumugam, N. Lignans of sesame: Purification methods, biological activities and biosynthesis—A review. Bioorg. Chem. 2013, 50, 1–10. [Google Scholar] [CrossRef]
- Olmo-García, L.; Kessler, N.; Neuweger, H.; Wendt, K.; Olmo-Peinado, J.M.; Fernández-Gutiérrez, A.; Baessmann, C.; Carrasco-Pancorbo, A. Unravelling the Distribution of Secondary Metabolites in Olea europaea L.: Exhaustive Characterization of Eight Olive-Tree Derived Matrices by Complementary Platforms (LC-ESI/APCI-MS and GC-APCI-MS). Molecules 2018, 23, 2419. [Google Scholar] [CrossRef]
- Struijs, K.; Vincken, J.P.; Gruppen, H. Comparison of atmospheric pressure chemical ionization and electrospray ionization mass spectrometry for the detection of lignans from sesame seeds. Rapid Commun. Mass Spectrom. 2008, 22, 3615–3623. [Google Scholar] [CrossRef]
- Hata, N.; Hayashi, Y.; Okazawa, A.; Ono, E.; Satake, H.; Kobayashi, A. Comparison of sesamin contents and CYP81Q1 gene expressions in aboveground vegetative organs between two Japanese sesame (Sesamum indicum L.) varieties differing in seed sesamin contents. Plant Sci. 2010, 178, 510–516. [Google Scholar] [CrossRef]
- Valentín-Blasini, L.; Blount, B.C.; Rogers, H.S.; Needham, L.L. HPLC-MS/MS method for the measurement of seven phytoestrogens in human serum and urine. J. Expo. Anal. Environ. Epidemiol. 2000, 10, 799–807. [Google Scholar] [CrossRef] [PubMed]
- Zhang, F.; Zhai, J.; Weng, N.; Gao, J.; Yin, J.; Chen, W. A Comprehensive Review of the Main Lignan Components of Schisandra chinensis (North Wu Wei Zi) and Schisandra sphenanthera (South Wu Wei Zi) and the Lignan-Induced Drug-Drug Interactions Based on the Inhibition of Cytochrome P450 and P-Glycoprotein Activities. Front. Pharm. 2022, 13, 816036. [Google Scholar] [CrossRef]
- Wang, C.Y.; Lee, S.S. Analysis and identification of lignans in Phyllanthus urinaria by HPLC-SPE-NMR. Phytochem. Anal. 2005, 16, 120–126. [Google Scholar] [CrossRef]
- Eklund, P.C.; Backman, M.J.; Kronberg, L.A.; Smeds, A.I.; Sjoholm, R.E. Identification of lignans by liquid chromatography-electrospray ionization ion-trap mass spectrometry. J. Mass Spectrom. 2008, 43, 97–107. [Google Scholar] [CrossRef]
- Wolfender, J.L.; Terreaux, C.; Hostettmann, K. The Importance Of LC-MS And LC-NMR In The Discovery Of New Lead Compounds from Plants. Pharm. Biol. 2000, 38 (Suppl. 1), 41–54. [Google Scholar] [CrossRef] [PubMed]
- Martini, S.; Cattivelli, A.; Conte, A.; Tagliazucchi, D. Black, green, and pink pepper affect differently lipid oxidation during cooking and in vitro digestion of meat. Food Chem. 2021, 350, 129246. [Google Scholar] [CrossRef]
- Cui, Y.; Wang, Q.; Shi, X.; Zhang, X.; Sheng, X.; Zhang, L. Simultaneous quantification of 14 bioactive constituents in Forsythia suspensa by liquid chromatography-electrospray ionisation-mass spectrometry. Phytochem. Anal. 2010, 21, 253–260. [Google Scholar] [CrossRef]
- Kiss, A.K.; Michalak, B.; Patyra, A.; Majdan, M. UHPLC-DAD-ESI-MS/MS and HPTLC profiling of ash leaf samples from different commercial and natural sources and their in vitro effects on mediators of inflammation. Phytochem. Anal. 2020, 31, 57–67. [Google Scholar] [CrossRef]
- Jiao, Q.S.; Xu, L.L.; Zhang, J.Y.; Wang, Z.J.; Jiang, Y.Y.; Liu, B. Rapid Characterization and Identification of Non-Diterpenoid Constituents in Tinospora sinensis by HPLC-LTQ-Orbitrap MS(n). Molecules 2018, 23, 274. [Google Scholar] [CrossRef]
- Huang, Q.; Zhang, F.; Liu, S.; Jiang, Y.; Ouyang, D. Systematic investigation of the pharmacological mechanism for renal protection by the leaves of Eucommia ulmoides Oliver using UPLC-Q-TOF/MS combined with network pharmacology analysis. Biomed. Pharmacother. 2021, 140, 111735. [Google Scholar] [CrossRef] [PubMed]
- Ling, X.-x.; Chen, H.; Fu, B.-b.; Ruan, C.-s.; Pana, M.; Zhou, K.; Fang, Z.-r.; Shao, J.-t.; Zhu, F.-q.; Gao, S. Xin-Ji-Er-Kang protects myocardial and renal injury in hypertensive heart failure in mice. Phytomedicine 2021, 91, 153675. [Google Scholar] [CrossRef] [PubMed]
- Stasevich, O.V.; Mikhalenok, S.G.; Kurchenko, V.P. Isolation of secoisolariciresinol diglucoside from lignan-containing extract of Linum usitatissimum seeds. Chem. Nat. Compd. 2009, 45, 21–23. [Google Scholar] [CrossRef]
- Yan, G.; Li, Q.; Tan, H.; Ge, T. Electrospray ionization ion-trap time-of-flight tandem mass spectrometry of two furofurans: Sesamin and gmelinol. Rapid Commun. Mass Spectrom. 2007, 21, 3613–3620. [Google Scholar] [CrossRef] [PubMed]
- Peng, Z.; Xu, Y.; Meng, Q.; Raza, H.; Zhao, X.; Liu, B.; Dong, C. Preparation of Sesaminol from Sesaminol Triglucoside by β-Glucosidase and Cellulase Hydrolysis. J. Am. Oil Chem. Soc. 2016, 93, 765–772. [Google Scholar] [CrossRef]
- Liu, X.T.; Wang, X.G.; Yang, Y.; Xu, R.; Meng, F.H.; Yu, N.J.; Zhao, Y.M. Qualitative and Quantitative Analysis of Lignan Constituents in Caulis Trachelospermi by HPLC-QTOF-MS and HPLC-UV. Molecules 2015, 20, 8107–8124. [Google Scholar] [CrossRef]
- Lehraiki, A.; Attoumbré, J.; Bienaimé, C.; Matifat, F.; Bensaddek, L.; Nava-Saucedo, E.; Fliniaux, M.A.; Ouadid-Ahidouch, H.; Baltora-Rosset, S. Extraction of lignans from flaxseed and evaluation of their biological effects on breast cancer MCF-7 and MDA-MB-231 cell lines. J. Med. Food 2010, 13, 834–841. [Google Scholar] [CrossRef]
- Hendrawati, O.; Woerdenbag, H.J.; Michiels, P.J.A.; Aantjes, H.G.; van Dam, A.; Kayser, O. Identification of lignans and related compounds in Anthriscus sylvestris by LC–ESI-MS/MS and LC-SPE–NMR. Phytochemistry 2011, 72, 2172–2179. [Google Scholar] [CrossRef]
- Lee, S.; Khoo, C.; Halstead, C.W.; Huynh, T.; Bensoussan, A. Liquid chromatographic determination of honokiol and magnolol in hou po (Magnolia officinalis) as the raw herb and dried aqueous extract. J. AOAC Int. 2007, 90, 1210–1218. [Google Scholar] [CrossRef]
- Knust, U.; Hull, W.E.; Spiegelhalder, B.; Bartsch, H.; Strowitzki, T.; Owen, R.W. Analysis of enterolignan glucuronides in serum and urine by HPLC-ESI-MS. Food Chem. Toxicol. 2006, 44, 1038–1049. [Google Scholar] [CrossRef]
- Guo, Z.; Zhao, A.; Chen, T.; Xie, G.; Zhou, M.; Qiu, M.; Jia, W. Differentiation of Schisandra chinensis and Schisandra sphenanthera using metabolite profiles based on UPLC-MS and GC-MS. Nat. Prod. Res. 2012, 26, 255–263. [Google Scholar] [CrossRef]
- Huang, S.; Liu, Y.; Li, Y.; Fan, H.; Huang, W.; Deng, C.; Song, X.; Zhang, D.; Wang, W. Dibenzocyclooctadiene lignans from the root bark of Schisandra sphenanthera. Phytochem. Lett. 2021, 45, 137–141. [Google Scholar] [CrossRef]
- Wei, X.-l.; Chen, Y.; Chen, X.-y.; Liang, J.-y.; Qu, W. A New Lignan from the Roots of Ginkgo biloba. Chem. Nat. Compd. 2015, 51, 819–821. [Google Scholar] [CrossRef]
- Figueroa, J.G.; Borrás-Linares, I.; Lozano-Sánchez, J.; Segura-Carretero, A. Comprehensive characterization of phenolic and other polar compounds in the seed and seed coat of avocado by HPLC-DAD-ESI-QTOF-MS. Food Res. Int. 2018, 105, 752–763. [Google Scholar] [CrossRef] [PubMed]
- Sólyomváry, A.; Tóth, G.; Kraszni, M.; Noszál, B.; Molnár-Perl, I.; Boldizsár, I. Identification and quantification of lignans and sesquilignans in the fruits of Cnicus benedictus L.: Quantitative chromatographic and spectroscopic approaches. Microchem. J. 2014, 114, 238–246. [Google Scholar] [CrossRef]
- Dias, M.M.; Zuza, O.; Riani, L.R.; de Faria Pinto, P.; Pinto, P.L.S.; Silva, M.P.; de Moraes, J.; Ataíde, A.C.Z.; de Oliveira Silva, F.; Cecílio, A.B.; et al. In vitro schistosomicidal and antiviral activities of Arctium lappa L. (Asteraceae) against Schistosoma mansoni and Herpes simplex virus-1. Biomed Pharm. 2017, 94, 489–498. [Google Scholar] [CrossRef]
- Sólyomváry, A.; Alberti, Á.; Darcsi, A.; Könye, R.; Tóth, G.; Noszál, B.; Molnár-Perl, I.; Lorántfy, L.; Dobos, J.; Őrfi, L.; et al. Optimized conversion of antiproliferative lignans pinoresinol and epipinoresinol: Their simultaneous isolation and identification by centrifugal partition chromatography and high performance liquid chromatography. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2017, 1052, 142–149. [Google Scholar] [CrossRef]
- Carrasco-Pancorbo, A.; Nevedomskaya, E.; Arthen-Engeland, T.; Zey, T.; Zurek, G.; Baessmann, C.; Deelder, A.M.; Mayboroda, O.A. Gas Chromatography/Atmospheric Pressure Chemical Ionization-Time of Flight Mass Spectrometry: Analytical Validation and Applicability to Metabolic Profiling. Anal. Chem. 2009, 81, 10071–10079. [Google Scholar] [CrossRef]
- Thompson, L.U.; Boucher, B.A.; Liu, Z.; Cotterchio, M.; Kreiger, N. Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan. Nutr. Cancer 2006, 54, 184–201. [Google Scholar] [CrossRef]
- Sarajlija, H.; Čukelj Mustač, N.; Novotni, D.; Mršić, G.; Brncic, M.; Curic, D. Preparation of Flaxseed for Lignan Determination by Gas Chromatography-Mass Spectrometry Method. Czech J. Food Sci. 2012, 30, 45. [Google Scholar] [CrossRef]
- Popova, I.E.; Hall, C.; Kubatova, A. Determination of lignans in flaxseed using liquid chromatography with time-of-flight mass spectrometry. J. Chromatogr. A 2009, 1216, 217–229. [Google Scholar] [CrossRef] [PubMed]
- Bonzanini, F.; Bruni, R.; Palla, G.; Serlataite, N.; Caligiani, A. Identification and distribution of lignans in Punica granatum L. fruit endocarp, pulp, seeds, wood knots and commercial juices by GC–MS. Food Chem. 2009, 117, 745–749. [Google Scholar] [CrossRef]
- Załuski, D.; Mendyk, E.; Smolarz, H.D. Identification of MMP-1 and MMP-9 inhibitors from the roots of Eleutherococcus divaricatus, and the PAMPA test. Nat. Prod. Res. 2016, 30, 595–599. [Google Scholar] [CrossRef]
- Liu, Z.; Saarinen, N.M.; Thompson, L.U. Sesamin is one of the major precursors of mammalian lignans in sesame seed (Sesamum indicum) as observed in vitro and in rats. J. Nutr. 2006, 136, 906–912. [Google Scholar] [CrossRef] [PubMed]
- Čukelj, N.; Jakasa, I.; Sarajlija, H.; Novotni, D.; Ćurić, D. Identification and quantification of lignans in wheat bran by gas chromatography-electron capture detection. Talanta 2011, 84, 127–132. [Google Scholar] [CrossRef]
- Xia, Y.-G.; Yang, B.-Y.; Liang, J.; Yang, Q.; Wang, D.; Kuang, H.-X. Quantitative Analysis and Fingerprint Profiles for Quality Control of Fructus Schisandrae by Gas Chromatography: Mass Spectrometry. Sci. World J. 2014, 2014, 806759. [Google Scholar] [CrossRef]
- Koulman, A.; Bos, R.; Medarde, M.; Pras, N.; Quax, W.J. A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related Plant species. Planta Med. 2001, 67, 858–862. [Google Scholar] [CrossRef]
- Saarinen, N.M.; Smeds, A.I.; Peñalvo, J.L.; Nurmi, T.; Adlercreutz, H.; Mäkelä, S. Flaxseed ingestion alters ratio of enterolactone enantiomers in human serum. J. Nutr. Metab. 2010, 2010, 403076. [Google Scholar] [CrossRef]
- Bommareddy, A.; Arasada, B.L.; Mathees, D.P.; Dwivedi, C. Determination of mammalian lignans in biological samples by modified gas chromatography/mass spectrometry. J. AOAC Int. 2007, 90, 641–646. [Google Scholar] [CrossRef]
- Edel, A.L.; Aliani, M.; Pierce, G.N. Supported liquid extraction in the quantitation of plasma enterolignans using isotope dilution GC/MS with application to flaxseed consumption in healthy adults. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2013, 912, 24–32. [Google Scholar] [CrossRef]
- Willför, S.M.; Ahotupa, M.O.; Hemming, J.E.; Reunanen, M.H.T.; Eklund, P.C.; Sjöholm, R.E.; Eckerman, C.S.E.; Pohjamo, S.P.; Holmbom, B.R. Antioxidant Activity of Knotwood Extractives and Phenolic Compounds of Selected Tree Species. J. Agric. Food Chem. 2003, 51, 7600–7606. [Google Scholar] [CrossRef] [PubMed]
- Yu, M.; Aoki, D.; Akita, T.; Fujiyasu, S.; Takada, S.; Matsushita, Y.; Yoshida, M.; Fukushima, K. Distribution of lignans and lignan mono/diglucosides within Ginkgo biloba L. stem. Phytochemistry 2022, 196, 113102. [Google Scholar] [CrossRef] [PubMed]
Species | Plant Part | Method | Solvent | Extraction Times | Extraction Time (min) | Temperature (°C) | Solvent to Sample Ratio | Reference |
---|---|---|---|---|---|---|---|---|
Abies alba Mill. | bark | Digestion | H2O | 1× | 120 | 70 | 1:5 | [39] |
Abies chensiensis Tiegh. | aerial parts | Maceration | 80% EtOH/H2O (v/v) | 3× | 180 | RT | - | [46] |
Abies delavayi var. nukiangensis (W.C.Cheng & L.K.Fu) Farjon & Silba | aerial parts | Maceration | 95% MeOH/H2O (v/v) | 3× | 180 | RT | - | [47] |
Arctium lappa L. | fructus | Digestion | 95% EtOH/H2O (v/v) | 2× | 180 | 80 | 1:10 | [48] |
Arctium lappa L. | fructus | MAE | 40% MeOH/H2O (v/v) | 3× | 200 s | - | 1:15 | [49] |
Arctium lappa L. | fructus | Soxhlet/heated reflux | 70% EtOH/H2O (v/v) | 3× | 60 | BP | 1:8 | [50] |
Arctium lappa L. | fructus | Soxhlet/heated reflux | 80% EtOH/H2O (v/v) | 3× | - | BP | 1:6 | [51] |
Arctium lappa L. | fructus | UAE | MeOH | 1× | 20 | - | 1:90 | [42] |
Arctium lappa L. | fructus | UAE | MeOH + H2O | 1× | 30 (with MeOH) and 30 (with water) | - | 1:15 | [29] |
Arctium lappa L. | roots | Maceration | 80% MeOH/H2O (v/v) | 1× | 8 h | RT | 1:50 | [25] |
Arctium lappa L. | seed | Maceration | MeOH | 3× | - | RT | 1:2 | [43] |
Arctium lappa L. | seed | Maceration | MeOH | 3× | - | RT | 3:5 | [52] |
Arctium lappa L. | seeds | Maceration | 80% MeOH/H2O (v/v) | 1× | 8 h | RT | 1:50 | [25] |
Carthamus tinctorius L. | seed | Maceration | MeOH | 5× | 15 h | RT | 1:2 | [53] |
Eleutherococcus divaricatus (Siebold & Zucc.) S.Y.Hu | root | Soxhlet/heated reflux | MeOH | 3× | - | BP | 1:2 | [54] |
Eleutherococcus senticosus (Rupr. & Maxim.) Maxim. | bark | Soxhlet/heated reflux | 70% MeOH/H2O (v/v) | 2× | 180 | BP | 1:6 | [55] |
Eleutherococcus senticosus (Rupr. & Maxim.) Maxim. | root | Soxhlet/heated reflux | H2O | 3× | 30 | BP | 1:6 | [37] |
Eleutherococcus senticosus (Rupr. & Maxim.) Maxim. | stem | Maceration | MeOH | 1× | 2 weeks | RT | - | [56] |
Eleutherococcus sessiliflorus (Rupr. & Maxim.) S.Y.Hu | fruit | Maceration | 70% EtOH/H2O (v/v) | 3× | 24 h | RT | 5:18 | [57] |
Forsythia × intermedia Zabel | flower | Digestion | 75% MeOH/H2O (v/v) | 6× | 120 | 70 | 1:20 | [58] |
Forsythia × intermedia Zabel | flower | Soxhlet/heated reflux | MeOH | 4× | - | BP | 1:200 | [44] |
Forsythia × intermedia Zabel | leaf | Digestion | 75% MeOH/H2O (v/v) | 6× | 120 | 70 | 1:20 | [58] |
Forsythia × intermedia Zabel | leaf | Soxhlet/heated reflux | MeOH | 4× | - | BP | 1:200 | [44] |
Forsythia koreana (Rehder) Nakai | flower | Maceration | 80% MeOH/H2O (v/v) | 2× | 24 h | RT | 3:100 | [59] |
Forsythia koreana (Rehder) Nakai | fruit | Maceration | MeOH | 3× | 7 days | RT | - | [60] |
Forsythia koreana (Rehder) Nakai | fruit | Maceration | MeOH | 3× | - | RT | 1:1 | [61] |
Forsythia koreana (Rehder) Nakai | stem | UAE | MeOH | 1× | 60 | - | 1:2 | [62] |
Forsythia suspensa | flower | Soxhlet/heated reflux | MeOH | 4× | - | BP | 1:200 | [44] |
Forsythia suspensa | fruit | Maceration | 70% EtOH/H2O (v/v) | 4× | - | RT | 2:1 | [63] |
Forsythia suspensa | fruit | Soxhlet/heated reflux | 50% MeOH/H2O (v/v) | 1× | 60 | BP | 1:25 | [64] |
Forsythia suspensa (Thunb.) Vahl | fruit | Soxhlet/heated reflux | 60% EtOH/H2O (v/v) | 2× | 120 | BP | - | [65] |
Forsythia suspensa (Thunb.) Vahl | fruit | Soxhlet/heated reflux | 95% EtOH/H2O (v/v) | 3× | 120 | BP | 1:60 | [66] |
Forsythia suspensa (Thunb.) Vahl | fruit | Soxhlet/heated reflux | MeOH | 7× | - | BP | 3:10 | [45] |
Forsythia suspensa (Thunb.) Vahl | fruit | UAE | 20% MeOH/H2O (v/v) | 1× | 30 | - | 1:5 | [67] |
Forsythia suspensa (Thunb.) Vahl | leaf | Soxhlet/heated reflux | MeOH | 4× | - | BP | 1:200 | [44] |
Forsythia viridissima Lindl. | flower | Soxhlet/heated reflux | MeOH | 4× | - | BP | 1:200 | [44] |
Forsythia viridissima Lindl. | leaf | Soxhlet/heated reflux | MeOH | 4× | - | BP | 1:200 | [44] |
Forsythia viridissima Lindl. | root | UAE | 80% MeOH/H2O (v/v) | 3× | 90 | RT | 7:10 | [68] |
Larix laricina (Du Roi) K.Koch | bark | Maceration | 80% EtOH/H2O (v/v) | 1× | 24 h | RT | 1:10 | [69] |
Linum usitatissimum L. | seed | Maceration | 60% EtOH/H2O (v/v) | 2× | 60 | RT | 10:75 | [70] |
Linum usitatissimum L. | seed | MAE | 70% MeOH/H2O (v/v) | 1× | 180 | 60 | 25:1 | [71] |
Linum usitatissimum L. | seed | Digestion | 75% MeOH/H2O (v/v) | 1× | 24 h | 65 | - | [72] |
Linum usitatissimum L. | seed | Digestion | 80% EtOH/H2O (v/v) | 1× | 240 | 55 | 1:14 | [34] |
Linum usitatissimum L. | seed | Maceration | 70% MeOH/H2O (v/v) | 1× | 120 | RT | 1:3 | [73] |
Linum usitatissimum L. | seed | Maceration | H2O | 1× | 60 | RT | 1:15 | [70] |
Linum usitatissimum L. | seed | UAE | 70% MeOH/H2O (v/v) | 3× | 4h | - | 1:6 | [74] |
Linum usitatissimum L. | seed | UAE | H2O + 0.2 N NaOH | 1× | 60 | 25 | - | [75] |
Linum usitatissimum L. | seed | UAE | 50% MeOH/H2O (v/v) | 1× | 10 + 60 | RT | 1:25 | [76] |
70% acetone/H2O (v/v) | 1× | - | RT | 1:25 | ||||
Magnolia biondii Pamp. | flower buds | Soxhlet/heated reflux | MeOH | 1× | 5 h | BP | - | [77] |
Magnolia officinalis Rehder & E.H. Wilson | flower buds | Soxhlet/heated reflux | MeOH | 3× | 180 | BP | 9:4 | [78] |
Pinus radiata D.Don | bark | Soxhlet/heated reflux | 70% acetone/H2O (v/v) | 4× | 180 | BP | 1:10 | [79] |
Pinus sylvestris L. | wood | ASE | 95% acetone/H2O (v/v) | 2× | 5 | 100 | - | [80] |
Pinus sylvestris L. | wood | Soxhlet/heated reflux | 90% acetone/H2O (v/v) | 1× | 180 | BP | 3:250 | [81] |
Saraca asoca (Roxb.) Willd. | bark | MAE | 70% MeOH/H2O (v/v) | 1× | 10 | - | 1:30 | [82] |
Schisandra chinensis (Turcz.) Baill. | fruit | Digestion | 70% MeOH/H2O (v/v) | 2× | 5 h | 50 | - | [83] |
Schisandra chinensis (Turcz.) Baill. | fruit | SFE | CO2 + MeOH | 2× | 20 | - | 1:10 | [84] |
Schisandra chinensis (Turcz.) Baill. | wood | SFE | CO2 + EtOH | 1× | 6 h | - | - | [85] |
Sesamum indicum L. | seed | Maceration | 80% EtOH/H2O (v/v) | 2× | 8 h | RT | 1:10 | [86] |
Sesamum indicum L. | seed | Maceration | cyclohexane + DCM + MeOH (1:1:1) | 3× | - | RT | 1:1 | [36] |
Sesamum indicum L. | seed | Maceration | H2O | 1× | 24 h | RT | - | [40] |
Sesamum indicum L. | seed | Soxhlet/heated reflux | n-hexane | 1× | 10 h | BP | - | [26] |
Sesamum indicum L. | seed | Soxhlet/heated reflux | MeOH | 5× | 8 h | BP | 1:10 | [87] |
Sesamum indicum L. | seed | UAE | 50% MeOH/H2O (v/v) | 1× | 10 + 60 | RT | 1:25 | [88] |
70% acetone/ H2O (v/v) | 1× | - | RT | 1:25 | ||||
Sesamum indicum L. | seed | UAE | 80% acetone/H2O (v/v) | 2× | 5 | - | 1:10 | [30] |
Syringa pinnatifolia Hemsl. | bark | Soxhlet/heated reflux | 95% EtOH + 80% EtOH | 2× | 90 | BP | 1:2 | [89] |
Syringa pinnatifolia Hemsl. | root | Maceration | 95% EtOH/H2O (v/v) | 3× | - | RT | 1:5 | [90] |
Syringa vulgaris L. | bark | Digestion | 60% EtOH/H2O (v/v) | 1× | 60 | 70 | 1:20 | [91] |
Species | Plant Part | Mobile Phase | Column | Elution Type | Detection System | Reference |
---|---|---|---|---|---|---|
Abies alba Mill. | bark | H2O and MeCN | RP-C18 column (10 cm × 4.6 mm, 2.7 µm) | gradient | DAD | [39] |
Arctium lappa L. | fruit | H2O + 0.01% HCOOH and MeCN | RP-C18 (250 mm × 4.6 mm, 5 µm) | gradient | DAD | [28] |
Arctium lappa L. | fruit | H2O and MeCN | RP-C18 (150 mm × 4.6 mm, 5 μm) | gradient | FLD | [42] |
Arctium lappa L. | fruit | MeCN and H2O + 0.1% HCOOH | RP-C18 (250 mm × 4.6 mm, 5 μm) | gradient | UV detection at 254 nm | [29] |
Arctium lappa L. | fruit, root | H2O + 0.1% HCOOH and MeOH + 0.1% HCOOH | RP-C18 (250 mm × 2.0 mm, 5 µm) | gradient | DAD | [25] |
Carthamus tinctorius L. | fruit | H2O + MeOH | RP-C12 (150 mm × 4.6 mm, 3.5 µm) | gradient | UV detection at 221/ESI-MS | [53] |
Eleutherococcus senticosus (Rupr. & Maxim.) Maxim. | bark | H2O + 0.2% CH3COOH and MeOH + 0.2% CH3COOH | RP-C18 (125 mm × 3 mm, 3 µm) | gradient | UV detection at 210 nm, 254 nm and 280 nm | [55] |
Eleutherococcus senticosus (Rupr. & Maxim.) Maxim. | root | H2O + 15% MeCN + 0.1% HCOOH | RP-C18 (250 mm × 4.6 mm, 5 µm) | isocratic | UV detection at 205 nm | [37] |
Eucommia ulmoides Oliv. | bark | H2O + 0.1% HCOOH and MeOH | RP-C18 (50 mm × 2.1 mm, 1.7 μm) | gradient | ESI-MS | [124] |
Forsythia × intermedia Zabel | flower, leaf | H2O + 0.1% HCOOH and MeCN + 0.1% HCOOH | RP-C18 (150 mm × 2.1 mm, 1.9 μm) | gradient | DAD, ESI-MS | [58] |
Forsythia koreana (Rehder) Nakai | stem | H2O + 32% MeCN | RP-C18 (150 mm × 4.6 mm, 5 μm) | isocratic | UV detection at 254 nm | [62] |
Forsythia suspensa (Thunb.) Vahl | fruit | 25% MeCN + 0.1% HCOOH | RP-C18 (250 mm × 4.6 mm, 5 μm) | isocratic | UV detection at 250 nm | [65] |
Forsythia suspensa (Thunb.) Vahl | fruit | H2O + 0.1% HCOOH and MeOH | RP-C18 (150 mm × 4.6 mm, 5 μm) coupled with RP-C18 (12.5 mm × 4.6 mm, 5 μm) | gradient | DAD | [64] |
Linum usitatissimum L. | seed | H2O + 0.2% CH3COOH and MeCN | RP-C18 (250 mm × 4.6 mm, 5 µm) | gradient | UV detection at 280 nm | [73] |
Linum usitatissimum L. | seed | H2O + 0.2% CH3COOH and MeCN | RP-C18 (250 mm × 4.6 mm, 5 µm) | gradient | UV detection at 280 nm | [71] |
Linum usitatissimum L. | seed | H2O + 0.2% CH3COOH and MeOH | RP-C18 (250 mm × 4.0 mm, 5 µm) | gradient | DAD | [75] |
Linum usitatissimum L. | seed | H2O + 16% MeOH + HCOOH and 100% MeOH | RP-C18 (250 mm × 4.6 mm, 5 µm) | gradient | UV detection at 283 nm | [34] |
Linum usitatissimum L. | seed | H2O and MeCN + HCOOH | RP-C8 (250 mm × 4 mm, 5 µm) | isocratic | CEAD | [125] |
Magnolia biondii Pamp. | flower | H2O + 0.2% HCOOH and MeCN | RP-C18 (250 mm x 4.6 mm, 5 μm) | gradient | UV detection at 278 nm/ESI-MS | [126] |
Schisandra chinensis (Turcz.) Baill. | fruit | H2O + 0.1% H3PO4 and MeCN | RP-C18 (150 mm × 2.0 mm, 5 µm) | gradient | UV detection at 280 nm | [83] |
Schisandra chinensis (Turcz.) Baill. | fruit | H2O and MeCN | RP-C18 (250 mm × 4.6 mm, 5 µm) | gradient | UV detection at 215 nm | [127] |
Schisandra rubriflora Rehder & E.H.Wilson | fruit, leaf | H2O and MeOH + 0.1% HCOOH | RP-C18 (150 mm × 4.6 mm, 2.7 µm) | gradient | ESI-MS | [128] |
Schisandra sphenanthera Rehder & E.H.Wilson | fruit | H2O and MeCN | RP-C18 (250 mm × 4.6 mm, 5 µm) | gradient | PAD-MS, ESI-MS | [129] |
Sesamum indicum L. | seed | H2O + 0.5% CH3COOH and MeCN | RP-C18 (150 mm × 4.6 mm, 2.7 µm) | gradient | DAD | [88] |
Sesamum indicum L. | seed | H2O and MeOH | RP-C18 (250 mm × 4 mm, 10 µm) | gradient | UV detection at 280 nm | [40] |
Sesamum indicum L. | seed | H2O + 0.5% CH3COOH and MeCN | RP-C18 (150 mm × 2.1 mm, 1.9 µm) | gradient | APCI-MS, ESI-MS | [130] |
Syringa vulgaris L. | bark | H2O + 0.1% HCOOH and MeCN + 0.1% HCOOH | RP-C18 (150 mm × 2.1 mm, 1.9 µm) | gradient | DAD, ESI-MS | [91] |
Compound | ESI a | Extracted Ion [m/z] | Fragment Ions [m/z] | Reference |
---|---|---|---|---|
Arctigenin | [M−H]− | 371 | 356, 295, 209 | [58] |
Arctigenin glucoside | [M+HCOO]− | 579 | 371 | [58] |
[M−H]− | 533 | 371 | ||
Aschantin | [M+H]+ | 401 | 365, 353, 261, 231, 219, 181, 151 | [126] |
[M+H−H2O]+ | 383 | |||
Conidendrin | [M−H]− | 355 | 340, 286, 147 | [143] |
Cyclolariciresinol | [M−H]− | 359 | 344, 329, 313, 159 | [141] |
Epipinoresinol | [M−H]− | 357 | 151 | [144] |
Epipinoresinol glucoside | [M+HCOO]− | 565 | 357 | [145] |
[M−H]− | 519 | 357 | ||
[M−H−Glc]− | 357 | - | ||
Fargesin | [M+H]+ | 371 | 335, 323, 283, 231, 219, 151 | [126] |
[M+H−H2O]+ | 353 | |||
Hinokinin | [M+H]+ | 355 | 337, 319, 261, 135 | [141] |
7-Hydroxylariciresinol | [M+Na+]+ | 399 | 384, 381, 369, 351, 219, 202 | [146] |
7-Hydroxymatairesinol | [M−H]− | 373 | 355, 340, 311, 296, 231, 160 | [141] |
Lariciresinol | [M−H]− | 359 | 344, 329, 208, 161 | [143] |
Magnolin | [M+H]+ | 417 | 381, 369, 329, 279, 249, 231, 219, 189 | [126] |
[M+H−H2O]+ | 399 | |||
Matairesinol | [M−H]− | 357 | 342, 313, 298, 281, 209 | [58] |
Matairesinol glucoside | [M−H]− | 519 | 357 | [58] |
[M−H−Glc]− | 357 | 342, 313, 298, 281, 209 | ||
Medioresinol | [M−H]− | 387 | 372, 181, 166, 151, 123 | [141] |
Medioresinol diglucoside | [M−H]− | 711 | 548, 387 | [124] |
Nortrachelogenin | [M−H]− | 373 | 355, 327, 235, 223 | [141] |
Olivil | [M−H]− | 375 | 357, 345, 327, 195, 179, 164 | [147] |
Olivil glucoside | [M−H]− | 537 | 375, 345, 327, 195, 179 | [124] |
[M−H−Glc]− | 375 | - | ||
Olivil diglucoside | [M+HCOO]− | 745 | - | [124] |
[M−H]− | 699 | 375, 345, 195, 179 | ||
[M−H−Glc]− | 537 | 327 | ||
7-Oxomatairesinol | [M−H]− | 371 | 356, 327, 205 | [141] |
Phillygenin | [M−H]− | 371 | 356 | [58] |
Phillygenin glucoside | [M+HCOO]− | 579 | 371 | [58] |
[M−H]− | 533 | 371 | ||
Pinoresinol | [M−H]− | 357 | 342, 311, 151, 136 | [141] |
Pinoresinol glucoside | [M−H]− | 519 | 357 | [145] |
[M−H−Glc]− | 357 | 342, 311, 151, 136 | ||
Pinoresinol diglucoside | [M+HCOO]− | 727 | - | [124] |
[M−H]− | 681 | 357, 151 | ||
[M−H−Glc]− | 519 | - | ||
Schizandrin | [M+H]+ | 433 | 415, 384, 369 | [148] |
Secoisolariciresinol | [M−H]− | 361 | 346, 331, 313, 179, 165 | [141] |
Secoisolariciresinol diglucoside | [M+2Na+−H]− | 732 | 722, 686 | [149] |
Sesamin | [M+H]+ | 355 | 353, 337 | [150] |
[M+H−H2O]+ | 337 | 319, 289, 261, 231, 203 | ||
[M+H−H2]+ | 353 | 323, 135, 77 | ||
Sesaminol | [M−H]− | 369 | - | [151] |
Sesaminol glucoside | [M−H]− | 531 | - | [151] |
Sesaminol diglucoside | [M−H]− | 693 | - | [151] |
Sesaminol triglucoside | [M−H]− | 855 | - | [151] |
Syringaresinol | [M−H]− | 417 | 402, 181, 166, 151 | [141] |
Syringaresinol glucoside | [M−H]− | 579 | 417, 181 | [124] |
[M−H−Glc]− | 417 | - | ||
Syringaresinol diglucoside | [M−H]− | 741 | 579, 417, 181 | [124] |
[M+HCOO]− | 787 | 579 | ||
[M−H−Glc]− | 579 | - | ||
Trachelogenin | [M−H]− | 387 | 357, 339, 329, 249, 193 | [141] |
Trachelogenin glucoside | [M+Na+]+ | 573 | 389, 371, 343, 325, 247, 203, 151, 137 | [152] |
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. |
© 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Patyra, A.; Kołtun-Jasion, M.; Jakubiak, O.; Kiss, A.K. Extraction Techniques and Analytical Methods for Isolation and Characterization of Lignans. Plants 2022, 11, 2323. https://doi.org/10.3390/plants11172323
Patyra A, Kołtun-Jasion M, Jakubiak O, Kiss AK. Extraction Techniques and Analytical Methods for Isolation and Characterization of Lignans. Plants. 2022; 11(17):2323. https://doi.org/10.3390/plants11172323
Chicago/Turabian StylePatyra, Andrzej, Małgorzata Kołtun-Jasion, Oktawia Jakubiak, and Anna Karolina Kiss. 2022. "Extraction Techniques and Analytical Methods for Isolation and Characterization of Lignans" Plants 11, no. 17: 2323. https://doi.org/10.3390/plants11172323