Abstract
A new oplopane-type sesquiterpenoid tussilagofarin (1) and a new chromone tussilagofarol (2), along with 18 known compounds 3–20, were isolated from the flower buds of Tussilago farfara. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR and HRESIMS data. Of the isolated compounds, oplopane- and bisabolane-type sesquterpenoids 1, 8–12, 15, and 16 were found to inhibit nitric oxide production in LPS-induced RAW 264.7 cells with IC50 values of 3.5–28.5 μM.
Similar content being viewed by others
References
Bohlmann, F., C. Zdero, and R.K. Gupta. 1981a. Notonipetrone-like sesquiterpenes from Senecio kleinia. Phytochemistry 20: 2024–2026.
Bohlmann, F., C. Zdero, J. Pickard, H. Robinson, and R.M. King. 1981b. New types of sesquiterpene lactones and other constituents from Trichogonia species. Phytochemistry 20: 1323–1333.
Gao, H., Y.N. Huang, B. Gao, P.Y. Xu, C. Inagaki, and J. Kawabata. 2008. α-Glucosidase inhibitory effect by the flower buds of Tussilago farfara. Food Chemistry 106: 1195–1201.
Hwangbo, C., H.S. Lee, J. Park, J. Choe, and J.H. Lee. 2009. The anti-inflammatory effect of tussilagone, from Tussilago farfara, is mediated by the induction of heme oxygenase-1 in murine macrophages. International Immunopharmacology 9: 1578–1584.
Jeon, S.H., W. Chun, Y.J. Choi, and Y.S. Kwon. 2008. Cytotoxic constituents from the bark of Salix hulteni. Archives of Pharmacal Research 31: 978–982.
Jiang, Z., F. Liu, J.J. Goh, L. Yu, S.F. Li, E.S. Ong, and C.N. Ong. 2009. Determination of senkirkine and senecionine in Tussilago farfara using microwave-assisted extraction and pressurized hot water extraction with liquid chromatography tandem mass spectrometry. Talanta 79: 539–546.
Kikuch, M., and N. Suzuki. 1992. Studies on the constituents of Tussilago farfara. II. Structures of new sesquiterpenoids isolated from the flower buds. Chemical & Pharmaceutical Bulletin 40: 2753–2755.
Kim, M.R., J.Y. Lee, H.H. Lee, D.K. Aryal, Y.G. Kim, S.K. Kim, E.R. Woo, and K.W. Kang. 2006. Antioxidative effects of quercetin-glycosides isolated from the flower buds of Tussilago farfara. Food and Chemical Toxicology 44: 1299–1307.
Kimura, J., and N. Maki. 2002. New loliolide derivatives from the brown alga Undaria pinnatifida. Journal of Natural Products 65: 57–58.
Kinjo, J., H. Higuchi, K. Fukui, and T. Nohara. 1991. Lignoids from Albizziae Cortex. II. A biodegradation pathway of syringaresinol. Chemical & Pharmaceutical Bulletin 39: 2952–2955.
Li, W., X. Huang, and X.W. Yang. 2012. New sesquiterpenoids from the dried flower buds of Tussilago farfara and their inhibition on NO production in LPS-induced RAW264.7 cells. Fitoterapia 83: 318–322.
Lim, H.J., H.S. Lee, and J.H. Ryu. 2008. Suppression of inducible nitric oxide synthase and cyclooxygenase-2 expression by tussilagone from Farfarae Flos in BV-2 microglial cells. Archives of Pharmacal Research 31: 645–652.
Liu, L.L., J.L. Yang, and Y.P. Shi. 2011. Sesquiterpenoids and other constituents from the flower buds of Tussilago farfara. Journal of Asian Natural Products Research 13: 920–929.
Lourenço, T.O., G. Akisue, and N.F. Roque. 1981. Reduced acetophenone derivatives from Calea cuneifolia. Phytochemistry 20: 773–776.
Mroczek, T., K. Glowniak, and A. Wlaszczyk. 2002. Simultaneous determination of N-oxides and free bases of pyrrolizidine alkaloids by cation-exchange solid-phase extraction and ion-pair high-performance liquid chromatography. Journal of Chromatography A 949: 249–262.
Naya, K., T. Okayama, M. Fujiwara, M. Nakata, T. Ohtsuka, and S. Kurio. 1990. Sesquiterpenes from the rhizomes of Ligularia dentata. Bulletin of the Chemical Society of Japan 63: 2239–2245.
Orden, A.A., F.R. Bisogno, O.S. Giordano, and M.K. Sanz. 2008. Comparative study in the asymmetric bioreduction of ketones by plant organs and undifferentiated cells. Journal of Molecular Catalysis B: Enzymatic 51: 49–55.
Park, H.R., M.Y. Yoo, J.H. Seo, I.S. Kim, N.Y. Kim, J.Y. Kang, L. Cui, C.S. Lee, C.H. Lee, and H.S. Lee. 2008. Sesquiterpenoids isolated from the flower buds of Tussilago farfara inhibit diacylglycerol acyltransferase. Journal of Agriculture and Food Chemistry 56: 10493–10497.
Park, Y., H.S. Ryu, H.K. Lee, J.S. Kim, J. Yun, J.S. Kang, B.Y. Hwang, J.T. Hong, Y. Kim, and S.B. Han. 2014. Tussilagone inhibits dendritic cell functions via induction of heme oxygenase-1. International Immunopharmacology 22: 400–408.
Qin, Z.B., J. Zhang, X.D. Wu, J. He, L.F. Ding, L.Y. Peng, X.Y. Li, Y. Li, L. Deng, Y.D. Guo, and Q.S. Zhao. 2014. Sesquiterpenoids from Tussilago farfara and their inhibitory effects on nitric oxide production. Planta Medica 80: 703–709.
Rocha, D.D., I.N. Dantas, M.R. Albuquerque, R.C. Montenegro, C. Pessoa, M.O. de Moraes, O.D. Pessoa, E.R. Silveira, and L.V. Costa-Lotufo. 2007. Studies on the cytotoxicity of miscellaneous compounds from Eupatorium betonicaeforme (Asteraceae). Chemistry & Biodiversity 4: 2835–2844.
Ryu, J.H., Y.S. Jeong, and D.H. Sohn. 1999. A new bisabolene epoxide from Tussilago farfara, and inhibition of nitric oxide synthesis in LPS-activated macrophages. Journal of Natural Products 62: 1437–1438.
Son, Y.K., M.H. Lee, and Y.N. Han. 2005. A new antipsychotic effective neolignan from Firmiana simplex. Archives of Pharmacal Research 28: 34–38.
Tang, W., and G. Eisenbrand. 2011. Handbook of Chinese medicinal plants: Chemistry, pharmacology, toxicology, vol. 1, 1206–1209. Weinheim: Wiley.
Wang, Q., T.H. Chen, K.F. Bastow, S.L. Morris-Natschke, K.H. Lee, and D.F. Chen. 2013. Songaricalarins A–E, cytotoxic oplopane sesquiterpenes from Ligularia songarica. Journal of Natural Products 76: 305–310.
Wu, D., M. Zhang, C. Zhang, and Z. Wang. 2008. Chromones from the flower buds of Tussilago farfara. Biochemical Systematics and Ecology 36: 219–222.
Yaoita, Y., H. Kamazawa, and M. Kikuchi. 1999. Structures of new oplopane-type sesquiterpenoids from the flower buds of Tussilago farfara. Chemical & Pharmaceutical Bulletin 47: 705–707.
Yaoita, Y., and M. Kikuchi. 1998. Triterpenoids from flower buds of Tussilago farfara. Journal of Natural Medicines 52: 273–275.
Yaoita, Y., N. Suzuki, and M. Kikuchi. 2001. Structures of new sesquiterpenoids from Farfarae Flos. Chemical & Pharmaceutical Bulletin 49: 645–648.
Acknowledgments
This research was supported financially by the Medical Research Center Program (MRC, 2008-0062275) through the National Research Foundation of Korea.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors have declared no conflict of interest.
Rights and permissions
About this article
Cite this article
Jang, H., Lee, J.W., Lee, C. et al. Sesquiterpenoids from Tussilago farfara inhibit LPS-induced nitric oxide production in macrophage RAW 264.7 cells. Arch. Pharm. Res. 39, 127–132 (2016). https://doi.org/10.1007/s12272-015-0667-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-015-0667-7