Benzofurans nor-sesquiterpenoids from Petasites hybridus rhizomes and absolute configuration by circular dichroism

Trends in Phytochemical Research

دوره 6، شماره 2، شهریور 2022، صفحه 145-154   

نوع مقاله: Original Article

شناسه دیجیتال (DOI): 10.30495/tpr.2022.1957782.1256

نویسندگان

Hanieh Asadi¹؛ Samad Nejad Ebrahimi^{* 1}؛ Marzieh Omrani¹؛ Hassan Esmaeili²

¹Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran

²Department of Agriculture, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran

چکیده

Petasites hybridus (L.) G.Gaertn., B.Mey. & Scherb. has been used as a medicine for different illnesses. A phytochemical study on hexane extract has been carried out using normal phase silica gel column and RP-HPLC chromatography. Five sesquiterpenoids were isolated, purified, and identified from hexane extract. The structures were elucidated by applying extensive 1D and 2D NMR and HRESI-TOFMS spectroscopy. In addition, circular dichroism (CD) spectra were applied to determine absolute configurations of constituents. Two never described benzofuran nor-sesquiterpenes (2S,3S)-5'-acetyl-(Z)-3-(acetoxymethyl) but-2-enoate tremetone) (4) and (2R,3R)-5'-acetyl-(Z)-3-(acetoxymethyl) but-2-enoate-7-hydroxytremetone (5) as well as euparin (1), (2S,3R)-3,6-dihydroxytremetone (2), and (2S,3S)-3,6-dihydroxytremetone (3) were isolated from the rhizome of Petasites hybridus, a species in Flora of Iran. Also, the euparin content of the MeOH extracts of seven populations of Iran was measured by HPLC-PDA. Notably, isolated euparin was the main constituent of Iranian P. hybridus varying between 2.7 and 9.7 µg/mg among samples.

کلیدواژه‌ها

Absolute configuration؛ Benzofuran؛ Isolation؛ Petasites hybridus؛ Phytochemical profiling؛ Sesquiterpenoids

مراجع

Agosti, R., Duke, R., Chrubasik, J., Chrubasik, S., 2006. Effectiveness of Petasites hybridus preparations in the prophylaxis of migraine: a systematic review. Phytomedicine 13(9), 743-746.
Avula, B., Wang, Y.-H., Wang, M., Smillie, T.J., Khan, I.A., 2012. Simultaneous determination of sesquiterpenes and pyrrolizidine alkaloids from the rhizomes of Petasites hybridus (L.) G.M. et Sch. and dietary supplements using UPLC-UV and HPLC-TOF-MS methods. J. Pharm. Biomed. Anal. 70, 53-63.
Blosa, M., Uricher, J., Nebel, S., Zahner, C., Butterweck, V., Drewe, J., 2021. Treatment of early allergic and late Inflammatory symptoms of allergic rhinitis with Petasites hybridus leaf extract (Ze 339): Results of a noninterventional observational study in Switzerland. Pharmaceuticals 14(3), 180.
Bodensieck, A., Kunert, O., Haslinger, E., Bauer, R., 2007. New eremophilane sesquiterpenes from a rhizome extract of Petasites hybridus. Helv. Chim. Acta. 90(1), 183-195.
Bohlmann, F., Zdero, C., 1977. Polyacetylenverbindungen, 243. Über die Inhaltsstoffe von Coreopsis parvifolia Blake. Tzoneva 110(2), 468-473.
Bruhn, T., Schaumlöffel, A., Hemberger, Y., Bringmann, G., 2013. SpecDis: Quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25(4), 243-249.
Castañeda, P., Mata, R., Lotina‐Hennsen, B., 1998. Effect of encecalin, euparin and demethylencecalin on thylakoid electron transport and photophosphorylation in isolated spinach chloroplasts. J. Sci. Food Agric. 78(1), 102-108.
Debrunner, B., Neuenschwander, M., Brenneisen, R., 1995. Sesquiterpenes of Petasites hybridus (L.) GM et Sch.: distribution of sesquiterpenes over plant organs. Pharm. Acta Helv. 70(2), 167-173.
Eaton, J., 1998. Butterbur, herbal help for migraine. Nat Pharm 2, 23-24.
Elso, O.G., Clavin, M., Hernandez, N., Sgarlata, T., Bach, H., Catalan, C.A.N., Aguilera, E., Alvarez, G., Sülsen, V.P., 2021. Antiprotozoal Compounds from Urolepis hecatantha (Asteraceae). Evid. Based Complementary Altern. Med. 2021, 6622894.
Han, X.-m., Jiao, M.-l., Liu, H.-r., Zhao, Z.-h., Zhan, H.-q., Guo, S.-y., 2020. Antidepressant activity of euparin: involvement of monoaminergic neurotransmitters and SAT1/NMDAR2B/BDNF signal pathway. Biol. Pharm. Bull. B20-00093.
Ito, K., Sakakibara, Y., Haruna, M., 1982. Seven guaianolides from Eupatorium chinense. Phytochemistry 21(3), 715-720.
Kamthong, B., Robertson, A., 1939. 198. Furano-compounds. Part V. The synthesis of tetrahydroeuparin and the structure of euparin. J. Chem. Soc., 933-936.
Khaleghi, F., Din, L.B., Charati, F.R., Yaacob, W.A., Khalilzadeh, M.A., Skelton, B., Makha, M., 2011. A new bioactive compound from the roots of Petasites hybridus. Phytochem. Lett. 4(3), 254-258.
Khaleghi, F., Jantan, I., Din, L.B., Yaacob, W.A., Khalilzadeh, M.A., Bukhari, S.N.A., 2014. Immunomodulatory effects of 1-(6-hydroxy-2-isopropenyl-1-benzofuran-5-yl)-1-ethanone from Petasites hybridus and its synthesized benzoxazepine derivatives. J. Nat. Med. 68(2), 351-357.
Kim, S.M., Kang, S.W., Jeon, J.S., Jung, Y.J., Kim, C.Y., Pan, C.H., Um, B.H., 2012. Rapid identification and evaluation of antioxidant compounds from extracts of Petasites japonicus by hyphenated‐HPLC techniques. Biomed. Chromatogr. 26(2), 199-207.
Ko, W.-C., Lei, C.-B., Lin, Y.-L., Chen, C.-F., 2001. Mechanisms of relaxant action of S-petasin and S-isopetasin, sesquiterpenes of Petasites formosanus, in isolated guinea pig trachea. Planta Med. 67(03), 224-229.
Kulinowski, Ł., Luca, S.V., Minceva, M., Skalicka-Woźniak, K., 2022. A review on the ethnobotany, phytochemistry, pharmacology and toxicology of butterbur species (Petasites L.). J. Ethnopharm. 293, 115263.
Lee, J.S., Jeong, M., Park, S., Ryu, S.M., Lee, J., Song, Z., Guo, Y., Choi, J.-H., Lee, D., Jang, D.S., 2019. Chemical Constituents of the leaves of butterbur (Petasites japonicus) and their anti-inflammatory effects. Biomolecules 9(12), 806.
Lin, Y.-L., Mei, C.-H., Huang, S.-L., Kuo, Y.-H., 1998. Four new sesquiterpenes from Petasites formosanus. J. Nat. Prod. 61(7), 887-890.
Lipton, R., Göbel, H., Einhäupl, K., Wilks, K., Mauskop, A., 2004a. Petasites hybridus root (butterbur) is an effective preventive treatment for migraine. Neurology 63(12), 2240-2244.
Lipton, R.B., Göbel, H., Einhäupl, K.M., Wilks, K., Mauskop, A., 2004b. Petasites hybridus root (butterbur) is an effective preventive treatment for migrain. Neurology 63(12), 2240.
Liu, Q., Shen, L., Wang, T.-T., Chen, C.-J., Qi, W.-Y., Gao, K., 2010. Novel modified furanoeremophilane-type sesquiterpenes and benzofuran derivatives from Ligularia veitchiana. Food Chem. 122(1), 55-59.
Mauskop, A., 2000. Petasites hybridus: ancient medicinal plant is effective prophylactic treatment for migraine. Huang 104-108.
Mohammadi, M., Yousefi, M., Habibi, Z., Dastan, D., 2012. Chemical composition and antioxidant activity of the essential oil of aerial parts of Petasites albus from Iran: A good natural source of euparin. Nat. Prod. Res. 26(4), 291-297.
Neuenschwander, M., Neuenschwander, A., Steinegger, E., 1979. Struktur der Sesquiterpene von Petasites hybridus (L.) GM et SCH.: Neopetasol‐Abkömmlinge. Helv. Chim. Acta. 62(2), 627-634.
Ożarowski, M., Przystanowicz, J., Adamczak, A., 2013. Phytochemical, pharmacological and clinical studies of Petasites hybridus (L.) P. Gaertn., B. Mey. & Scherb. A review. Herba Pol. 59(4), 108-128.
Steelink, C., Marshall, G.P., 1979. Structures, syntheses, and chemotaxonomic significance of some new acetophenone derivatives from Encelia farinosa Gray. J. Org. Chem. 44(9), 1429-1433.
Uzunova, V.P., Tzoneva, R.D., Momchilova, A.B., Maslenkova, L.T., 2020. Sesquiterpene patterns of the leaves and roots in local populations of medicinal plant Petasites hybridus (L.) from Bulgaria. Ecol. Balk. 239-245
Visintini Jaime, M.F., Campos, R.H., Martino, V.S., Cavallaro, L.V., Muschietti, L.V., 2013. Antipoliovirus activity of the organic extract of Eupatorium buniifolium: isolation of euparin as an active compound. Evid. Based Complementary Altern. Med. 2013, 402364, 1-8.
Wang, G.-J., Shum, A.Y.-C., Lin, Y.-L., Liao, J.-F., Wu, X.-C., Ren, J., Chen, C.-F., 2001. Calcium channel blockade in vascular smooth muscle cells: major hypotensive mechanism of S-petasin, a hypotensive sesquiterpene from Petasites formosanus. J. Pharmacol. Exp. Ther. 297(1), 240-246.