Identification of Acidic Triterpenoid Saponins from Silene vulgaris Using a Methylation-Based Isolation and LC-MS Analysis Strategy
The Silene genus plants in the Caryophyllaceae family are a large genus with over 850 species. It has been known that Silene genus plants contain triterpenoid saponins. These saponins have glucuronic acid in the sugar chain and are difficult to separate in chromatography. In this study, a strategy w...
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| Published in | Chemical & pharmaceutical bulletin Vol. 73; no. 3; pp. 179 - 188 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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TOKYO
The Pharmaceutical Society of Japan
07.03.2025
Pharmaceutical Soc Japan Japan Science and Technology Agency |
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| Abstract | The Silene genus plants in the Caryophyllaceae family are a large genus with over 850 species. It has been known that Silene genus plants contain triterpenoid saponins. These saponins have glucuronic acid in the sugar chain and are difficult to separate in chromatography. In this study, a strategy was developed to clarify the distribution of triterpenoid saponins in whole plants of Silene vulgaris by isolation of neutralized saponins using methylation reactions, which were used as standard substances for LC-MS analysis, and elucidating their characteristic MS and MS/MS fragment patterns. The n-butanol fraction of the methanol extract from the whole plant of S. vulgaris was separated to obtain fractions including saponins by octadecyl silica column chromatography. Then, each fraction was treated with trimethylsilyl diazomethane for methylation of the carboxyl groups of glucuronic acid in the molecules, and five triterpenoid methylated saponins (7a, 13a, 14a, 16a, and 17a) were isolated using HPLC. The chemical structures of the isolated compounds were determined by spectroscopic analyses including NMR and MS, and their characteristic fragmentations were also clarified in LC-MS and MS/MS. It was performed on the n-butanol fraction from the whole plant of S. vulgaris, and the chemical structures of 22 triterpenoid saponins were estimated based on the MS and MS/MS fragmentation patterns of the isolated triterpenoid saponins. |
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| AbstractList | The Silene genus plants in the Caryophyllaceae family are a large genus with over 850 species. It has been known that Silene genus plants contain triterpenoid saponins. These saponins have glucuronic acid in the sugar chain and are difficult to separate in chromatography. In this study, a strategy was developed to clarify the distribution of triterpenoid saponins in whole plants of Silene vulgaris by isolation of neutralized saponins using methylation reactions, which were used as standard substances for LC-MS analysis, and elucidating their characteristic MS and MS/MS fragment patterns. The n-butanol fraction of the methanol extract from the whole plant of S. vulgaris was separated to obtain fractions including saponins by octadecyl silica column chromatography. Then, each fraction was treated with trimethylsilyl diazomethane for methylation of the carboxyl groups of glucuronic acid in the molecules, and five triterpenoid methylated saponins (7a, 13a, 14a, 16a, and 17a) were isolated using HPLC. The chemical structures of the isolated compounds were determined by spectroscopic analyses including NMR and MS, and their characteristic fragmentations were also clarified in LC-MS and MS/MS. It was performed on the n-butanol fraction from the whole plant of S. vulgaris, and the chemical structures of 22 triterpenoid saponins were estimated based on the MS and MS/MS fragmentation patterns of the isolated triterpenoid saponins. The Silene genus plants in the Caryophyllaceae family are a large genus with over 850 species. It has been known that Silene genus plants contain triterpenoid saponins. These saponins have glucuronic acid in the sugar chain and are difficult to separate in chromatography. In this study, a strategy was developed to clarify the distribution of triterpenoid saponins in whole plants of Silene vulgaris by isolation of neutralized saponins using methylation reactions, which were used as standard substances for LC-MS analysis, and elucidating their characteristic MS and MS/MS fragment patterns. The n-butanol fraction of the methanol extract from the whole plant of S. vulgaris was separated to obtain fractions including saponins by octadecyl silica column chromatography. Then, each fraction was treated with trimethylsilyl diazomethane for methylation of the carboxyl groups of glucuronic acid in the molecules, and five triterpenoid methylated saponins (7a, 13a, 14a, 16a, and 17a) were isolated using HPLC. The chemical structures of the isolated compounds were determined by spectroscopic analyses including NMR and MS, and their characteristic fragmentations were also clarified in LC-MS and MS/MS. It was performed on the n-butanol fraction from the whole plant of S. vulgaris, and the chemical structures of 22 triterpenoid saponins were estimated based on the MS and MS/MS fragmentation patterns of the isolated triterpenoid saponins.The Silene genus plants in the Caryophyllaceae family are a large genus with over 850 species. It has been known that Silene genus plants contain triterpenoid saponins. These saponins have glucuronic acid in the sugar chain and are difficult to separate in chromatography. In this study, a strategy was developed to clarify the distribution of triterpenoid saponins in whole plants of Silene vulgaris by isolation of neutralized saponins using methylation reactions, which were used as standard substances for LC-MS analysis, and elucidating their characteristic MS and MS/MS fragment patterns. The n-butanol fraction of the methanol extract from the whole plant of S. vulgaris was separated to obtain fractions including saponins by octadecyl silica column chromatography. Then, each fraction was treated with trimethylsilyl diazomethane for methylation of the carboxyl groups of glucuronic acid in the molecules, and five triterpenoid methylated saponins (7a, 13a, 14a, 16a, and 17a) were isolated using HPLC. The chemical structures of the isolated compounds were determined by spectroscopic analyses including NMR and MS, and their characteristic fragmentations were also clarified in LC-MS and MS/MS. It was performed on the n-butanol fraction from the whole plant of S. vulgaris, and the chemical structures of 22 triterpenoid saponins were estimated based on the MS and MS/MS fragmentation patterns of the isolated triterpenoid saponins. |
| ArticleNumber | c24-00809 |
| Author | Li, Wei Koike, Kazuo Otsuki, Kouharu Liu, Danyang Kikuchi, Takashi |
| Author_xml | – sequence: 1 fullname: Kikuchi, Takashi organization: Faculty of Pharmaceutical Sciences, Toho University, 2–2–1 Miyama, Funabashi, Chiba 274–8510, Japan – sequence: 2 fullname: Liu, Danyang organization: Faculty of Pharmaceutical Sciences, Toho University, 2–2–1 Miyama, Funabashi, Chiba 274–8510, Japan – sequence: 3 fullname: Otsuki, Kouharu organization: Faculty of Pharmaceutical Sciences, Toho University, 2–2–1 Miyama, Funabashi, Chiba 274–8510, Japan – sequence: 4 fullname: Koike, Kazuo organization: Faculty of Pharmaceutical Sciences, Toho University, 2–2–1 Miyama, Funabashi, Chiba 274–8510, Japan – sequence: 5 fullname: Li, Wei organization: Faculty of Pharmaceutical Sciences, Toho University, 2–2–1 Miyama, Funabashi, Chiba 274–8510, Japan |
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| Cites_doi | 10.1002/rcm.8480 10.1016/j.phytol.2023.01.008 10.1248/cpb.c21-00180 10.1016/j.chroma.2019.460501 10.1002/mrc.4252 10.1111/j.1365-2621.2006.01187.x 10.1016/j.phytochem.2020.112274 10.1021/np049586j 10.1021/np020105a 10.1080/14786419.2011.637216 10.1002/tax.12230 10.1016/S0367-326X(03)00031-5 10.1002/mrc.1069 10.1016/j.phytochem.2016.07.011 10.1016/0031-9422(95)00222-S 10.1002/hlca.201000016 10.1016/S0031-9422(97)00087-3 10.1248/cpb.c19-00255 10.1021/np980172y 10.1016/0378-8741(91)90064-K 10.1021/np980505r 10.1248/cpb.c19-00423 10.5246/jcps.2014.04.034 10.1002/hlca.200690098 10.1248/cpb.37.895 10.1177/1934578X1501001129 |
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| Keywords | Oleanane NMR LC-MS WILD Silene vulgaris triterpenoid saponin ROOTS TRIPLE QUADRUPOLE-TIME |
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| References | 9) Lacaille-DuBois M.-A., Hanquet B., Cui Z.-H., Lou Z.-C., Wagner H., Phytochemistry, 45, 985–990 (1997). 26) Kim Y. B., Reed D. W., Covello P. S., Nat. Prod. Commun., 10, 1919–1922 (2015). 6) Gaidi G., Miyamoto T., Laurens V., Lacaille-Dubois M.-A., J. Nat. Prod., 65, 1568–1572 (2002). 18) Xu W., Fang J., Zhu Z., Wu J., Li Y., Nat. Prod. Res., 26, 2002–2007 (2012). 11) Tan N.-H., Zhao S.-X., Zhou J., Chen C.-X., Huaxue Xuebao, 53, 1024–1033 (1995). 13) Fu H., Koike K., Li W., Nikaido T., Lin W., Guo D., J. Nat. Prod., 68, 754–758 (2005). 8) Lacaille-Dubois M.-A., Hanquet B., Cui Z.-H., Lou Z.-C., Wagner H., Phytochemistry, 40, 509–514 (1995). 12) Tan N.-H., Zhou J., Zhao S.-X., Chen C.-X., Huaxue Xuebao, 54, 722–728 (1996). 22) Tsujimoto T., Arai R., Yoshitomi T., Yamamoto Y., Ozeki Y., Hakamatsuka T., Uchiyama N., Chem. Pharm. Bull., 69, 741–746 (2021). 19) Stavrianidi A., J. Chromatogr. A, 1609, 460501 (2020). 2) Jafari F., Zarre S., Gholipour A., Eggens F., Rabeler R. K., Oxelman B., Taxon, 69, 337–368 (2020). 31) Luo J.-G., Kong L.-Y., Helv. Chim. Acta, 89, 947–953 (2006). 21) Chen J., Tan M., Zou L., Liu X., Chen S., Shi J., Chen C., Wang C., Mei Y., Chem. Pharm. Bull., 67, 839–848 (2019). 4) Bechkri S., Alabdul Magid A., Voutquenne-Nazabadioko L., Kabouche A., Sayagh C., Harakat D., Kabouche Z., Phytochem. Lett., 54, 50–56 (2023). 20) Wang C., Cai Z., Shi J., Chen S., Tan M., Chen J., Chen L., Zou L., Chen C., Liu Z., Liu X., Chem. Pharm. Bull., 67, 1104–1115 (2019). 28) Glensk M., Wray V., Nimtz M., Schöpke T., J. Nat. Prod., 62, 717–721 (1999). 1) Bellakhdar J., Claisse R., Fleurentin J., Younos C., J. Ethnopharmacol., 35, 123–143 (1991). 16) Zou C., Jiang J. X., Chen C. X., Zhou J., Zhao Q., Chin. Chem. Lett., 10, 33–36 (1999). 23) Ma B., Yang S., Li J., Ouyang H., He M., Feng Y., Tan T., Rapid Commun. Mass Spectrom., 33, 1464–1474 (2019). 27) Bouguet-Bonnet S., Rochd M., Mutzenhardt P., Henry M., Magn. Reson. Chem., 40, 618–621 (2002). 30) Okabe H., Nagao T., Hachiyama S., Yamauchi T., Chem. Pharm. Bull., 37, 895–900 (1989). 15) Wu Q., Tu G.-Z., Fu H.-Z., Magn. Reson. Chem., 53, 544–550 (2015). 5) Lacaille-Dubois M.-A., Hanquet B., Cui Z.-H., Lou Z.-C., Wagner H., J. Nat. Prod., 62, 133–136 (1999). 29) Larhsini M., Marston A., Hostettmann K., Fitoterapia, 74, 237–241 (2003). 14) Wu Q., Tu G., Fu H., J. Chin. Pharm. Sci., 23, 246–250 (2014). 25) Alarcon R., Ortiz L. T., Garcia P., Int. J. Food Sci. Technol., 41, 1239–1242 (2006). 3) Takahashi N., Li W., Koike K., Phytochemistry, 129, 77–85 (2016). 7) Bechkri S., Alabdul Magid A., Sayagh C., Berrehal D., Harakat D., Voutquenne-Nazabadioko L., Kabouche Z., Kabouche A., Phytochemistry, 172, 112274 (2020). 17) Xu W., Wu J.-M., Zhu Z., Sha Y., Fang J., Li Y.-S., Helv. Chim. Acta, 93, 2007–2014 (2010). 24) Murata J., Yonekura K., “APG Makino’s Illustrated Flora in Colour II,” The Hokuryukan Co., Ltd., Tokyo, 2013, p. 2304. 10) Tan N.-H., Zhou S.-X., Zhou J., Cheng C.-X., Wang D.-Z., He Y.-N. Gaodeng Xuexiao, Huaxue Xuebao, 15, 859–860 (1994). Alarcón, R (WOS:000241767800014) 2006; 41 TAN, NH (WOS:A1995TF11600017) 1995; 53 Xu, W (WOS:000309287500008) 2012; 26 Xu, W (WOS:000283908200016) 2010; 93 BELLAKHDAR, J (WOS:A1991GR58200004) 1991; 35 Takahashi, N (WOS:000381832900008) 2016; 129 Stavrianidi, A (WOS:000509632500040) 2020; 1609 Wu, Q (WOS:000359801800010) 2015; 53 Gaidi, G (WOS:000179394400010) 2002; 65 Bechkri, S (WOS:000927867800001) 2023; 54 Jafari, F (WOS:000541946300001) 2020; 69 Bouguet-Bonnet, S (WOS:000177489100012) 2002; 40 LacailleDubois, MA (WOS:A1997XG65800021) 1997; 45 Tsujimoto, T (WOS:000681043000006) 2021; 69 Murata, J. (001440113700007.24) 2013 Zou, C (WOS:000081029400015) 1999; 10 Larhsini, M (WOS:000182946900004) 2003; 74 Bechkri, S (WOS:000518871000015) 2020; 172 Chen, JL (WOS:000478859100011) 2019; 67 Kim, YB (WOS:000365932500031) 2015; 10 Tan, N.-H. (001440113700007.10) 1994; 15 Luo, JG (WOS:000238040800014) 2006; 89 Tan, NH (WOS:A1996VH00500016) 1996; 54 Ma, BL (WOS:000480285100006) 2019; 33 Lacaille-Dubois, MA (WOS:000078186300027) 1999; 62 LACAILLEDUBOIS, MA (WOS:A1995RV97300027) 1995; 40 Wan, CC (WOS:000488888000012) 2019; 67 Fu, HZ (WOS:000229596900022) 2005; 68 OKABE H (BIOSIS:BCI198988030931) 1989; 37 Glensk, M (WOS:000080625100014) 1999; 62 22 23 24 25 26 27 28 29 30 31 10 11 12 13 14 15 16 17 18 19 1 2 3 4 5 6 7 8 9 20 21 |
| References_xml | – reference: 14) Wu Q., Tu G., Fu H., J. Chin. Pharm. Sci., 23, 246–250 (2014). – reference: 8) Lacaille-Dubois M.-A., Hanquet B., Cui Z.-H., Lou Z.-C., Wagner H., Phytochemistry, 40, 509–514 (1995). – reference: 22) Tsujimoto T., Arai R., Yoshitomi T., Yamamoto Y., Ozeki Y., Hakamatsuka T., Uchiyama N., Chem. Pharm. Bull., 69, 741–746 (2021). – reference: 31) Luo J.-G., Kong L.-Y., Helv. Chim. Acta, 89, 947–953 (2006). – reference: 11) Tan N.-H., Zhao S.-X., Zhou J., Chen C.-X., Huaxue Xuebao, 53, 1024–1033 (1995). – reference: 20) Wang C., Cai Z., Shi J., Chen S., Tan M., Chen J., Chen L., Zou L., Chen C., Liu Z., Liu X., Chem. Pharm. Bull., 67, 1104–1115 (2019). – reference: 17) Xu W., Wu J.-M., Zhu Z., Sha Y., Fang J., Li Y.-S., Helv. Chim. Acta, 93, 2007–2014 (2010). – reference: 26) Kim Y. B., Reed D. W., Covello P. S., Nat. Prod. Commun., 10, 1919–1922 (2015). – reference: 4) Bechkri S., Alabdul Magid A., Voutquenne-Nazabadioko L., Kabouche A., Sayagh C., Harakat D., Kabouche Z., Phytochem. Lett., 54, 50–56 (2023). – reference: 27) Bouguet-Bonnet S., Rochd M., Mutzenhardt P., Henry M., Magn. Reson. Chem., 40, 618–621 (2002). – reference: 1) Bellakhdar J., Claisse R., Fleurentin J., Younos C., J. Ethnopharmacol., 35, 123–143 (1991). – reference: 25) Alarcon R., Ortiz L. T., Garcia P., Int. J. Food Sci. Technol., 41, 1239–1242 (2006). – reference: 21) Chen J., Tan M., Zou L., Liu X., Chen S., Shi J., Chen C., Wang C., Mei Y., Chem. Pharm. Bull., 67, 839–848 (2019). – reference: 23) Ma B., Yang S., Li J., Ouyang H., He M., Feng Y., Tan T., Rapid Commun. Mass Spectrom., 33, 1464–1474 (2019). – reference: 6) Gaidi G., Miyamoto T., Laurens V., Lacaille-Dubois M.-A., J. Nat. 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| Snippet | The Silene genus plants in the Caryophyllaceae family are a large genus with over 850 species. It has been known that Silene genus plants contain triterpenoid... |
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| SubjectTerms | Butanol Chemistry Chemistry, Medicinal Chemistry, Multidisciplinary Chromatography Chromatography, High Pressure Liquid Column chromatography Diazomethane LC-MS Life Sciences & Biomedicine Liquid Chromatography-Mass Spectrometry Methylation Molecular Structure NMR Nuclear magnetic resonance Oleanane Pharmacology & Pharmacy Physical Sciences Plant extracts Saponins Saponins - chemistry Saponins - isolation & purification Science & Technology Silene Silene - chemistry Silene vulgaris Tandem Mass Spectrometry Triterpenes - analysis Triterpenes - chemistry Triterpenes - isolation & purification triterpenoid saponin |
| Title | Identification of Acidic Triterpenoid Saponins from Silene vulgaris Using a Methylation-Based Isolation and LC-MS Analysis Strategy |
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