Published October 31, 2022
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Germacranolide- and guaianolide-type sesquiterpenoids from Achillea alpina L. reduce insulin resistance in palmitic acid-treated HepG2 cells via inhibition of the NLRP3 inflammasome pathway
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- 1. * & College of Pharmacy, Henan University of Chinese Medicine, Zhengzhou, 450046, China
Description
Xue, Gui-Min, Zhao, Chen-Guang, Xue, Jin-Feng, Du, Kun, Duan, Jiang-Jing, Pan, Hao, Li, Meng, Chen, Hui, Sun, Yan-Jun, Feng, Wei-Sheng, Ma, Ting, Zhang, Wen-Da (2022): Germacranolide- and guaianolide-type sesquiterpenoids from Achillea alpina L. reduce insulin resistance in palmitic acid-treated HepG2 cells via inhibition of the NLRP3 inflammasome pathway. Phytochemistry (113297) 202: 1-9, DOI: 10.1016/j.phytochem.2022.113297, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113297
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- urn:lsid:plazi.org:pub:210F037EFFEEFF97FFCC343B3717FFFE
References
- Bai, M., Chen, J.J., Xu, W., Dong, S.H., Liu, Q.B., Lin, B., Huang, X.X., Yao, G.D., Song, S. J., 2020. Elephantopinolide A-P, germacrane-type sesquiterpene lactones from Elephantopus scaber induce apoptosis, autophagy and G2/M phase arrest in hepatocellular carcinoma cells. Eur. J. Med. Chem. 198, 112362 https://doi.org/ 10.1016/j.ejmech.2020.112362.
- Bastard, J.P., Maachi, M., Lagathu, C., Kim, M.J., Caron, M., Vidal, H., Capeau, J., Feve, B., 2006. Recent advances in the relationship between obesity, inflammation, and insulin resistance. Eur. Cytokine Netw. 17, 4-12. https://doi.org/10.1104/ pp.92.4.891.
- Cao, Y., Si, Y., Li, M., Fan, D., Cao, M., Cheon, S.H., Liang, J., Lu, P., 2021. Licochalcone E improves insulin sensitivity in palmitic acid-treated HepG2 cells through inhibition of the NLRP3 signaling pathway. Int. Immunopharm. 99, 107923-107932. https:// doi.org/10.1016/j.intimp.2021.107923.
- Ch´avez-Silva, F., Cer´on-Romero, L., Arias-Dur´an, L., Navarrete-V´azquez, G., Almanza- P´erez, J., Rom´an-Ramos, R., Ramirez-Avila ´, G., Perea-Arango, I., Villalobos- Molina, R., Estrada-Soto, S., 2018. Antidiabetic effect of Achillea millefollium through multitarget interactions: α -glucosidases inhibition, insulin sensitization and insulin secretagogue activities. J. Ethnopharmacol. 212, 1-7. https://doi.org/10.1016/j. jep.2017.10.005.
- Cui, J.J., Ji, K.L., Liu, H.C., Zhou, B., Liu, Q.F., Xu, C.H., Ding, J., Zhao, J.X., Yue, J.M., 2019. Cytotoxic tigliane diterpenoids from Croton damayeshu. J. Nat. Prod. 82, 1550-1557. https://doi.org/10.1021/acs.jnatprod.9b00042.
- Ding, S.J., Xu, S., Ma, Y., Liu, G., Jang, H.M., Fang, J., 2019. Modulatory mechanisms of the NLRP3 inflammasomes in diabetes. Biomolecules 9, 850-864. https://doi.org/ 10.3390/biom9120850.
- Fang, L., Lin, W., Qiu, G., Cai, Y., Yan, P., Cai, X., Li, W., Tu, H., Dong, J., 2015. Substolides A-G, germacrane sesquiterpenoids from Salvia substolonifera. Phytochemistry 120, 28-35. https://doi.org/10.1016/j.phytochem.2015.09.013.
- Glasl, S., Gunbilig, D., Narantuya, S., Werner, I., Jurenitsch, J., 2001a. Combination of chromatographic and spectroscopic methods for the isolation and characterization of polar guaianolides from Achillea asiatica. J. Chromatogr. A. 936, 193-200. https:// doi.org/10.1016/s0021-9673(01)00947-5.
- Glasl, S., Presser, A., Gunbilig, D., Werner, I., Narantuya, S., Haslinger, E., Jurenitsch, J., Kubelka, W., 2001b. Highly hydroxylated guaianolides of Achillea asiatica and Middle European Achillea species. Phytochemistry 58, 1189-1194. https://doi.org/ 10.1016/S0031-9422(01)00281-3.
- Glasl, S., Mucaji, P., Werner, I., Presser, A., Jurenitsch, J., 2002. Sesquiterpenes and flavonoid aglycones from a Hungarian taxon of the Achillea millefolium group. Z. Naturforsch. C Biosci. 57, 976-982. https://doi.org/10.1515/znc-2002-11-1203.
- Han, Y.C., Xu, X.X., Tang, C.Y., Gao, P., Chen, X.H., Xiong, X.F., Yang, M., Yang, S.K., Zhu, X.J., Yuan, S.G., Liu, F.Y., Xiao, L., Kanwar, Y.S., Sun, L., 2018. Reactive oxygen species promote tubular injury in diabetic nephropathy: the role of the mitochondrial ros-txnip-nlrp3 biological axis. Redox Biol. 16, 32-46. https://doi. org/10.1016/j.redox.2018.02.013.
- Jakupovic, J., Boeker, R., Grenz, M., Paredes, L., Bohlmann, F., El-Din, A.S., 1988. Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry 27, 1135-1140. https://doi.org/10.1016/0031-9422(88)80289-9.
- Jia, X., Qiu, T.M., Yao, X.F., Jiang, L.P., Wang, N.N., Wei, S., Tao, Y., Pei, P., Wang, Z.D., Zhang, J.Y., Zhu, Y.H., Yang, G., Liu, X.F., Liu, S., Sun, X.C., 2020. Arsenic induces hepatic insulin resistance via mtROS-NLRP3 inflammasome pathway. J. Hazard Mater. 399, 123034 https://doi.org/10.1016/j.jhazmat.2020.123034.
- Lee, H.J., Sim, M.O., Woo, K.W., Jeong, D.E., Jung, H.K., An, B., Cho, H.W., 2019. Antioxidant and antimelanogenic activities of compounds isolated from the aerial parts of Achillea alpina. L. Chem. Biodivers. 16, e1900033 https://doi.org/10.1002/ cbdv.201900033.
- Liu, Z.G., Li, Z.L., Bai, J., Meng, D.L., Li, N., Pei, Y.H., Zhao, F., Hua, H.M., 2014. Anti-inflammatory diterpenoids from the roots of Euphorbia ebracteolata. J. Nat. Prod. 77, 792-799. https://doi.org/10.1021/np400873v.
- Minakawa, T., Toume, K., Arai, M.A., Sadhu, S.K., Ahmed, F., Ishibashi, M., 2012. Eudesmane-type sesquiterpenoid and guaianolides from Kandelia candel in a screening program for compounds to overcome TRAIL resistance. J. Nat. Prod. 75, 1431-1435. https://doi.org/10.1021/np300179c.
- Mohammadhosseini, M., Sarker, S.D., Akbarzadeh, A., 2017. Chemical composition of the essential oils and extracts of Achillea species and their biological activities: a review. J. Ethnopharmacol. 199, 257-315. https://doi.org/10.1016/j. jep.2017.02.010.
- Mustafa, K.G., Ganai, B.A., Akbar, S., Dar, M.Y., Masood, A., 2012. β- Cell protective efficacy, hypoglycemic and hypolipidemiceffects of extracts of Achillea millifolium in diabetic rats. Chin. J. Nat. Med. 10, 185-189. https://doi.org/10.3724/SP. J.1009.2012.00185.
- Papakosta, K., Grafakou, M.E., Barda, C., Kostopoulos, I.V., Tsitsilonis, O., Skaltsa, H., 2020. Cytotoxicity and anti-cancer activity of the genus Achillea L. Curr. Med. Chem. 27, 6910-6925. https://doi.org/10.2174/0929867327666200505092514.
- Segal, R., Feuerstein, I., Duddeck, H., Kaiser, M., Danin, A., 1983. The sesquiterpene lactones from two populations of Artemisia herba alba. Phytochemistry 22, 129-131. https://doi.org/10.1016/S0031-9422(00)80072-2.
- Stefani, R., Eberlin, M.N., Tomazela, D.M., Costa, F.B.D., 2003. Eudesmanolides from Dimerostemma vestitum. J. Nat. Prod. 66, 401-403. https://doi.org/10.1021/ np020304u.
- Tachikawa, E., 2017. Glibenclamide inhibits nlrp3 inflammasome-mediated Il-1beta secretion in human trophoblasts. J. Pharmacol. Sci. 135, 89-95. https://doi.org/ 10.1016/j.jphs.2017.09.032.
- Todorova, M.N., Mikhova, B., Trendafilova, A., Vitkova, A., Duddeck, H., Anchev, M., 2006. Sesquiterpene lactones from Achillea asplenifolia. Biochem. Systemat. Ecol. 34, 136-143. https://doi.org/10.1016/j.bse.2005.08.006.
- Todorova, M., Trendafilova, A., Mikhova, B., Vitkova, A., Duddeck, H., 2007. Chemotypes in Achillea collina based on sesquiterpene lactone profile. Phytochemistry 68, 1722-1730. https://doi.org/10.1016/j. phytochem.2007.04.013.
- Trendafilova, A., Todorova, M., Mikhova, B., Vitkova, A., Duddeck, H., 2006. Sesquiterpene lactones from Achillea collina. J. Becker ex Reichenb. Phytochemistry. 67 https://doi.org/10.1016/j.phytochem.2006.01.033, 764-370.
- Xue, G.M., Li, X.Q., Chen, C., Chen, K., Wang, X.B., Gu, Y.C., Luo, J.G., Kong, L.Y., 2018. Highly oxidized guaianolide sesquiterpenoids with potential anti-inflammatory activity from Chrysanthemum indicum. J. Nat. Prod. 81, 378-386. https://doi.org/ 10.1021/acs.jnatprod.7b00867.
- Xue, G.M., Zhu, D.R., Han, C., Wang, X.B., Luo, J.G., Kong, L.Y., 2019. Artemisianins A- D, new stereoisomers of seco-guaianolide involved heterodimeric. [4+2] adducts from Artemisia argyi induce apoptosis via enhancement of endoplasmic reticulum stress. Bioorg. Chem 84, 295-301. https://doi.org/10.1016/j.bioorg.2018.11.013.
- Yang, M., Li, J.X., Li, X., Jia, Z.J., 2005. Sesquiterpenes and other constituents from Achillea wilsoniana. Pharmazie 60, 554-558. https://doi.org/10.1080/ 14786410500034949.
- Yazdanparast, R., Ardestani, A., Jamshidi, S., 2007. Experimental diabetes treated with Achillea santolina: effect on pancreatic oxidative parameters. J. Ethnopharmacol. 112, 13-18. https://doi.org/10.1016/j.jep.2007.01.030.
- Ye, Y., Dawa, D., Liu, G.H., Zhao, M., Tseden, D., Gu, Y.C., Ding, L.S., Cao, Z.X., Zhou, Y., 2018. Antiproliferative sesquiterpenoids from Ligularia rumicifolia with diverse skeletons. J. Nat. Prod. 81, 1992-2003. https://doi.org/10.1021/acs. jnatprod.8b00197.
- Zhang, W.J., Li, X.H., Shi, Y.P., 2010. A pair of epimeric spirosesquiterpenes from the roots of Ligularia fischeri. J. Nat. Prod. 73, 143-146. https://doi.org/10.1021/ np900492b.
- Zhou, F., Li, S., Yang, J., Ding, J.W., He, C., Teng, L., 2019. In-vitro cardiovascular protective activity of a new achillinoside from Achillea alpina. Rev. Bras. Farmacogn. 29, 445-448. https://doi.org/10.1016/j.bjp.2019.02.008.