Published March 31, 2021 | Version v1
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Guaiane-type sesquiterpenoids from the roots of Stellera chamaejasme L. and their neuroprotective activities

  • 1. * & Key Laboratory of Computational Chemistry Based Natural Antitumor Drug Research & Development, Liaoning Province, School of Traditional Chinese Materia Medica,

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Cheng, Zhuo-Yang, Hou, Zi-Lin, Ren, Jing-Xian, Zhang, Ding-Ding, Lin, Bin, Huang, Xiao-Xiao, Song, Shao-Jiang (2021): Guaiane-type sesquiterpenoids from the roots of Stellera chamaejasme L. and their neuroprotective activities. Phytochemistry (112628) 183: 1-10, DOI: 10.1016/j.phytochem.2020.112628, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112628

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urn:lsid:plazi.org:pub:FFA3FF9FFFD34D5B2863C5060B72D37F

References

  • Adekenov, S.M., 2016. Chemical modification of arglabin and biological activity of its new derivatives. Fitoterapia 110, 196-205. https://doi.org/10.1016/j. fitote.2015.11.018.
  • An, T., Li, L., Lin, Y., Zeng, F., Lin, P., Zi, J., 2020. Characterization of guaiene synthases from Stellera chamaejasme L. flowers and their application in de novo production of (-)-rotundone in yeast. J. Agric. Food Chem. 68, 3214-3219. https://doi.org/ 10.1021/acs.jafc.9b08303.
  • Asada, Y., Sukemori, A., Watanabe, T., Malla, K.J., Yoshikawa, T., Li, W., Koike, K., Chen, C.H., Akiyama, T., Qian, K., Nakagawa-Goto, K., Morris-Natschke, S.L., Lee, K. H., 2011. Stelleralides A-C, novel potent anti-HIV Daphnane-type diterpenoids from Stellera chamaejasme L. Org. Lett. 13, 2904-2907. NPU1210063192.
  • Blay, G., Garcia, B., Molina, E., Pedro, J.R., 2005. Synthesis of all 7αH -guaia-4,11-dien-3- one diastereomers from (+ )-dihydrocarvone. Tetrahedron 61, 11156-11162. https://doi.org/10.1016/j.tet.2005.09.026.
  • Chen, W., Luo, X.H., Wang, Z., Zhang, Y.Y., Liu, L.P., Wang, H.B., 2015. A new biflavone glucoside from the roots of Stellera chamaejasme. J. Chin. Nat. Med. 13, 550-553. https://doi.org/10.3724/SP.J.1009.2015.00550.
  • De Mieri, M., Du, K., Neuburger, M., Saxena, P., Zietsman, P.C., Hering, S., van der Westhuizen, J.H., Hamburger, M., 2015. hERG Channel inhibitory daphnane diterpenoid orthoesters and polycephalones A and B with unprecedented skeletons from Gnidia polycephala. J. Nat. Prod. 78, 1697-1707. https://doi.org/10.1021/acs. jnatprod.5b00344.
  • El-Desoky, A.H.H., Eguchi, K., Kato, H., Kishimoto, N., Misumi, S., Watanabe, T., Tsukamoto, S., 2020. Chamaejasmins, cytotoxic guaiane sesquiterpenes from the root of Stellera chamaejasme L. Fitoterapia 146, 104714-104718. https://doi.org/ 10.1016/j.fitote.2020.104714.
  • Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J., 2013. Gaussian 09, Revision D.01. Gaussian, Inc, Wallingford, CT.
  • Guo, R., Ren, Q., Tang, Y.X., Zhao, F., Lin, B., Huang, X.X., Song, S.J., 2020. Sesquiterpenoids from the roots of Daphne genkwa Siebold et Zucc. with potential anti-inflammatory activity. Phytochemistry 174, 112348-112355. https://doi.org/ 10.1016/j.phytochem.2020.112348.
  • Hashimoto, M.Y., Costa, D.P., Faria, M.T., Ferreira, H.D., Santos, S.C., Paula, J.R., Seraphin, J.C., Ferri, P.H., 2014. Chemotaxonomy of Marsypianthes Mart. ex Benth. Based on essential oil variability. J. Braz. Chem. Soc. 28, 1504-1511. https://doi. org/10.5935/0103-5053.20140133.
  • He, J., Xu, J.K., Liu, S.N., Yang, Y.F., Zhang, W.K., 2018. A new guaiane sesquiterpene from rhizome of Stellera chamaejasme. Chin. Tradit. Herb. Drugs 49, 5235-5237. https://doi.org/10.7501/j.issn.0253-2670.2018.22.002.
  • Huang, S.Z., Li, X.N., Ma, Q.Y., Dai, H.F., Li, L.C., Cai, X.H., Liu, Y.Q., Zhou, J., Zhao, Y. X., 2014. Daphnauranols A-C, new antifeedant sesquiterpenoids with a 5/6/7 ring system from Daphne aurantiaca. Tetrahedron Lett. 55, 3693-3696. https://doi.org/ 10.1016/j.tetlet.2014.05.007.
  • Jing, C.X., Guo, J.J., Yang, B.J., Fan, S.R., Wang, Y.T., Chen, D.Z., Hao, X.J., 2019. Stelleraguaianone B and C, two new sesquiterpenoids from Stellera chamaejasme L. Fitoterapia 134, 443-446. https://doi.org/10.1016/j.fitote.2019.03.024.
  • Li, J., Shen, Q., Bao, C.H., Chen, L.T., Li, X.R., 2014a. A new dicoumarinyl ether from the roots of Stellera chamaejasme L. Molecules 19, 1603-1607. https://doi.org/10.3390/ molecules19021603.
  • Li, J., Zhang, J.J., Pang, X.X., ZhengChen, X.L., Gan, L.S., 2014b. Biflavanones with antiproliferative activity against eight human solid tumor cell lines from Stellera chamaejasme. Fitoterapia 93, 163-167. https://doi.org/10.1016/j. fitote.2014.01.002.
  • Li, J., Zhao, W., Hu, J.L., Cao, X., Yang, J., Li, X.R., 2011. A new C-3/C-3'' -biflavanone from the roots of Stellera chamaejasme L. Molecules 16, 6465-6469. https://doi.org/ 10.3390/molecules16086465.
  • Liu, L.P., Han, K., Chen, W., Zhang, Y.Y., Tong, L.J., Peng, T., Xie, H., Ding, J., Wang, H. B., 2014. Topoisomerase II inhibitors from the roots of Stellera chamaejasme L. Bioorg. Med. Chem. 22, 4198-4203. https://doi.org/10.1016/j.bmc.2014.05.042.
  • Liu, L.P., Wang, X.Y., Wang, H.B., 2012. A new lignan from the roots of Stellera chamaejasme. Chem. Nat. Compd. 48, 559-561. https://doi.org/10.1007/s10600- 012-0309-y.
  • Ma, C.T., Eom, T., Cho, E., Wu, B., Kim, T.R., Oh, K.B., Han, S.B., Kwon, S.W., Park, J.H., 2017. Aquilanols A and B, macrocyclic humulene-type sesquiterpenoids from the agarwood of Aquilaria malaccensis. J. Nat. Prod. 80, 3043-3048. https://doi.org/ 10.1021/acs.jnatprod.7b00462.
  • Ma, G.H., Chen, K.X., Zhang, L.Q., Li, Y.M., 2019. Advance in biological activities of natural guaiane-type sesquiterpenes. Med. Chem. Res. 28, 1339-1358. https://doi. org/10.1007/s00044-019-02385-7.
  • Ma, J., Ren, Q.H., Dong, B.J., Shi, Z.Y., Zhang, J., Jin, D.Q., Xu, J., Ohizumi, Y., Lee, D.L., Guo, Y.Q., 2018. NO inhibitory constituents as potential anti-neuroinflammatory agents for AD from Blumea balsamifera. Bioorg. Chem. 76, 449-457. https://doi.org/ 10.1016/j.bioorg.2017.12.008.
  • Mi, C.N., Mei, W.L., Wang, H., Yang, L., Dong, W.H., Gai, C.J., Yuan, J.Z., Long, W.X., Dai, H.F., 2019. Four new guaiane sesquiterpenoids from agarwood of Aquilaria filaria. Fitoterapia 135, 79-84. https://doi.org/10.1016/j.fitote.2019.04.007.
  • Perveen, S., Alqahtani, J., Orfali, R., Al-Taweel, A.M., Yusufoglu, H.S., Abdel-Kader, M. S., Taglialatela-Scafati, O., 2019. Antimicrobial guaianolide sesquiterpenoids from leaves of the Saudi Arabian plant Anvillea garcinii. Fitoterapia 134, 129-134. https:// doi.org/10.1016/j.fitote.2019.02.017.
  • Song, D.H., Jo, Y.H., Ahn, J.H., Kim, S.B., Yun, C.-Y., Kim, Y., Hwang, B.Y., Lee, M.K., 2017. Sesquiterpenes from fruits of Torilis japonica with inhibitory activity on melanin synthesis in B16 cells. J. Nat. Med. 72, 155-160. https://doi.org/10.1007/ s11418-017-1123-4.
  • Suleimen, E.M., Dzhalmakhanbetova, R.I., Pak, R.N., Kulyyasov, A.T., Adekenov, S.M., 2014. Synthesis and biological activity of estafiatin phosphonate derivatives. Chem. Nat. Compd. 50, 846-849. https://doi.org/10.1007/s10600-014-1097-3.
  • Tsai, Y.C., Hsu, H.C., Yang, W.C., Tsai, W.J., Chen, C.C., Watanabe, T., 2007. α -Bulnesene, a PAF inhibitor isolated from the essential oil of Pogostemon cablin. Fitoterapia 78, 7-11. https://doi.org/10.1016/j.fitote.2006.09.016.
  • Wang, J., Liu, Q.B., Hou, Z.L., Shi, S.C., Ren, H., Yao, G.D., Lin, B., Huang, X.X., Song, S. J., 2020. Discovery of guaiane-type sesquiterpenoids from the roots of Daphne genkwa with neuroprotective effects. Bioorg. Chem. 95 https://doi.org/10.1016/j. bioorg.2019.103545, 103545-102553.
  • Wang, Z.X., Cheng, M.C., Zhang, X.Z., Hong, Z.L., Gao, M.Z., Kan, X.X., Li, Q., Wang, Y.J., Zhu, X.X., Xiao, H.B., 2014. Cytotoxic biflavones from Stellera chamaejasme. Fitoterapia 99, 334-340. https://doi.org/10.1016/j.fitote.2014.10.002.
  • Xiong, J., Wang, L.J., Qian, J.C., Wang, P.P., Wang, X.J., Ma, G.L., Zeng, H.Q., Li, J., Hu, J.F., 2018. Structurally diverse sesquiterpenoids from the endangered ornamental plant Michelia shiluensis. J. Nat. Prod. 81, 2195-2204. https://doi.org/ 10.1021/acs.jnatprod.8b00386.
  • Yan, M., Lu, Y., Chen, C.H., Zhao, Y., Lee, K.H., Chen, D.F., 2015. Stelleralides D-J and anti-HIV daphnane diterpenes from Stellera chamaejasme. J. Nat. Prod. 78, 2712-2718. https://doi.org/10.1021/acs.jnatprod.5b00660.
  • Yan, Z.Y., Lv, T.M., Wang, Y.X., Shi, S.C., Chen, J.J., Bin, L., Liu, Q.B., Huang, X.X., Song, S.J., 2020. Terpenylated coumarins from the root bark of Ailanthus altissima (Mill.) Swingle. Phytochemistry 175, 112361-112369. https://doi.org/10.1016/j. phytochem.2020.112361.
  • Yang, G.H., Chen, D.F., 2006. Isodaphnoretin B, a new bicoumarin from Stellera chamaejasme. Chin. J. Nat. Med. 4, 425-427.
  • Yang, J.L., Dao, T.T., Hien, T.T., Zhao, Y.M., Shi, Y.P., 2019. Further sesquiterpenoids from the rhizomes of Homalomena occulta and their anti-inflammatory activity. Bioorg. Med. Chem. Lett 29, 1162-1167. https://doi.org/10.1016/j. bmcl.2019.03.031.
  • Yang, Y.J., Yao, J., Jin, X.J., Shi, Z.N., Shen, T.F., Fang, J.G., Yao, X.J., Zhu, Y., 2016. Sesquiterpenoids and tirucallane triterpenoids from the roots of Scorzonera divaricata. Phytochemistry 124, 86-98. https://doi.org/10.1016/j. phytochem.2016.01.015.
  • Zhang, C., Zhou, S.S., Feng, L.Y., Zhang, D.Y., Lin, N.M., Zhang, L.H., Pan, J.P., Wang, J. B., Li, J., 2013. In vitro anti-cancer activity of chamaejasmenin B and neochamaejasmin C isolated from the root of Stellera chamaejasme L. Acta Pharmacol. Sin. 34, 262-270. https://doi.org/10.1038/aps.2012.158.
  • Zhou, Q.M., Chen, M.H., Li, X.H., Peng, C., Lin, D.S., Li, X.N., He, Y., Xiong, L., 2018. Absolute configurations and bioactivities of guaiane-type sesquiterpenoids isolated from Pogostemon cablin. J. Nat. Prod. 81, 1919-1927. https://doi.org/10.1021/acs. jnatprod.7b00690.
  • Zhu, S.S., Qin, D.P., Wang, S.X., Yang, C., Li, G.P., Cheng, Y.X., 2019. Commipholactam A, a cytotoxic sesquiterpenoidal lactam from Resina Commiphora. Fitoterapia 134, 382-388. https://doi.org/10.1016/j.fitote.2019.03.008.