Published January 31, 2023
| Version v1
Journal article
Restricted
Undescribed isoquinolines from Zanthoxylum nitidum and their antiproliferative effects against human cancer cell lines
Authors/Creators
- 1. * & State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources
Description
Qin, Feng, Wang, Cai Yi, Wang, Chun-Gu, Chen, Yao, Li, Jin-Jun, Li, Mei-Shan, Zhu, Yan-Kui, Lee, Sang Kook, Wang, Heng-Shan (2023): Undescribed isoquinolines from Zanthoxylum nitidum and their antiproliferative effects against human cancer cell lines. Phytochemistry (113476) 205: 1-12, DOI: 10.1016/j.phytochem.2022.113476, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113476
Files
Restricted
The record is publicly accessible, but files are restricted to users with access.
Linked records
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:FFDAFFED2D1FA644FFB3FFB2FFD9FFCD
References
- Avtanski, D.B., Nagalingam, A., Tomaszewski, J.E., Risbood, P., Difillippantonio, M.J., Saxena, N.K., Malhotra, S.V., Sharma, D., 2016. Indolo-pyrido-isoquinolin based alkaloid inhibits growth, invasion and migration of breast cancer cells via activation of p53-miR34a axis. Mol. Oncol. 10, 1118-1132. https://doi: 10.1016/j.molonc.20 16.04.003.
- Bilic, J., Huang, Y.L., Davidson, G., Zimmermann, T., Cruciat, C.M., Bienz, M., Niehrs, C., 2007. Wnt induces LRP6 signalosomes and promotes dishevelled dependent LRP6 phosphorylation. Science 316, 1619-1622. https://doi: 10.1126/science.1137065.
- Byun, W.S., Jin, M., Yu, J., Kim, W.K., Song, J., Chung, H.J., Jeong, L.S., Lee, S.K., 2018. A novel selenonucleoside suppresses tumor growth by targeting Skp2 degradation in paclitaxel-resistant prostate cancer. Biochem. Pharmacol. 158, 84-94. https://doi: 10.1016/j.bcp.2018.10.002.
- Chen, I.S., Wu, S.J., Leu, Y.L., Tsai, I.W., Wu, T.S., 1996. Alkaloids from root bark of Zanthoxylum simulans. Phytochemistry 42, 217-219. https://doi:10.1016/0031-9422(95)00856-x.
- Chen, J.J., Lin, Y.H., Day, S.H., Hwang, T.L., Chen, I.S., 2011. New benzenoids and anti-inflammatory constituents from Zanthoxylum nitidum. Food Chem. 125, 282-287. https://doi: 10.1016/j.foodchem.2010.09.069.
- Das, B.P., Chowdhury, D.N., Chowdhury, B., 1982. Isolation and structure of glycosolone, a new 2-quinolone alkaloid from Glycosmis pentaphylla (Retz) DC. Indian J. Chem. B. 21B, 176-178.
- Deng, A.J., Zhang, H.J., Li, Q., Li, Z.H., Zhang, Z.H., Wu, L.Q., Li, L., Qin, H.L., 2017. Six scalemic mixtures of 6-monosubstituted dihydrobenzophenanthridine alkaloids from Chelidonium majus and optically active structures of enantiomers. Phytochemistry 144, 159-170. https://doi: 10.1016/j.phytochem.2017.09.009.
- Fish, F., Meshal, I., Waterman, P., 1978. Alkaloids of Oricia suaveolens. Planta Med. 33, 228-231. https://doi:10.1055/s-0028-1097380.
- Gao, P., Wang, L., Zhao, L., Zhang, Q.Y., Zeng, K.W., Zhao, M.B., Jiang, Y., Tu, P.F., Guo, X.Y., 2020. Anti-inflammatory quinoline alkaloids from the root bark of Dictamnus dasycarpus. Phytochemistry 172, 112260. https://doi:10.1016/j.phytoch em.2020.112260.
- Gregorieff, A., Clevers, H., 2005. Wnt signaling in the intestinal epithelium: from endoderm to cancer. Genes Dev. 19, 877-890. https://doi: 10.1101/gad.1295405.
- Guo, F.J., Li, Y.C., 2011. Phenolic and amide constituents from Lycianthes marlipoensis. China J. Chin. Mater. Med. 36, 2507-2510. https://doi:10.4268/cjcmm20111812.
- Hengartner, M.O., 2000. The biochemistry of apoptosis. Nature 407, 770-776. https://doi: 10.1038/35037710.
- Hu, J., Zhang, W.D., Liu, R.H., Zhang, C., Shen, Y.H., Li, H.L., Liang, M.J., Xu, X.K., 2006. Benzophenanthridine alkaloids from Zanthoxylum nitidum (Roxb.) DC, and their analgesic and anti-inflammatory activities. Chem. Biodivers. 3, 990-995. https://doi: 10.1002/cbdv.200690108.
- Hu, J., Zhang, W.D., Shen, Y.H., Zhang, C., Xu, L., Liu, R.H., Wang, B., Xu, X.K., 2007. Alkaloids from Zanthoxylum nitidum (Roxb.) DC. Biochem. Systemat. Ecol. 35, 114-117. https://doi: 10.1016/j.bse.2006.10.001.
- Ishii, H., Ishikawa, T., Lu, S.T., Chen, I.S., 1976. Arnottianamide and isoarnottianamide: the structural establishment due to chemical conversion from the known benzo[c] phenanthridine alkaloids by the novel Baeyer-Villiger like oxidation of an immonium group. Tetrahedron Lett. 17, 1203-1206. https://doi: 10.1016/s0040-4039(00)78018-x.
- Ishikawa, T., Ishii, H., 1976. Chemical constituents of rutaceous plants. XXXII. Iwamide: a new phenolic amide derived from a quaternary benzo[c]phenanthridine alkaloid. Heterocycles 5, 275-279.
- Kim, D.H., Wang, C.Y., Hu, R.C., Lee, J.Y., Luu, T.T.T., Park, H.J., Lee, S.K., 2019. Antitumor activity of Vanicoside B isolated from Persicaria dissitiflora by targeting CDK8 in triple-negative breast cancer cells. J. Nat. Prod. 82, 3140-3149. https://doi :10.1021/acs.jnatprod.9b00720.
- Kingsbury, C.A., Thornton, W.B., 1966. The conformational preferences in diastereomers. I. J. Org. Chem. 31, 1000-1004. https://doi:10.1021/jo01277a002.
- Koyano, T., Namba, M., Kobayashi, T., Nakakuni, K., Nakano, D., Fukushima, M., Nishiyama, A., Matsuyama, M., 2019. The p21 dependent G2 arrest of the cell cycle in epithelial tubular cells links to the early stage of renal fibrosis. Sci. Rep. 9, 12059. https://doi: 10.1038/s41598-019-48557-8.
- Kupchan, S.M., Moniot, J.L., Kanojia, R.M., O' Brien, J.B., 1971. Photochemical synthesis of aporphines. J. Org. Chem. 36, 2413-2418. https://doi: 10.1021/jo00816a007.
- Engeland, K., Sacchi, A., Soddu, S., Piaggio, G., 2001. NF-Y mediates the transcriptional inhibition of the cyclin B1, cyclin B2, and cdc25C promoters upon induced G2 arrest. J. Biol. Chem. 276, 5570-5576. https://doi:10.1074/jbc. m006052200.
- Martin, M.T., Rasoanaivo, L.H., Raharisololalao, A., 2005. Phenanthridine alkaloids from Zanthoxylum madagascariense. Fitoterapia 76, 590-593. https://doi:10.1016/j.fi tote.2005.04.003.
- Nguyen, D.T., Iqbal, J., Han, J., Pierens, G.K., Wood, S.A., Mellick, G.D., Feng, Y., 2020. Chemical constituents from Macleaya cordata (Willd) R. Br. and their phenotypic functions against a Parkinson' s disease patient-derived cell line. Bioorg. Med. Chem. 28, 115732. https://doi: 10.1016/j.bmc.2020.115732.
- Plazas, E., Hagenow, S., Murillo, M.A., Stark, H., Cuca, L.E., 2020. Isoquinoline alkaloids from the roots of Zanthoxylum rigidum as multi-target inhibitors of cholinesterase, monoamine oxidase A and Aβ1-42 aggregation. Bioorg. Chem. 98, 103722. https://doi: 10.1016/j.bioorg.2020.103722.
- Puricelli, L., Innocenti, G., Monache, G.D., Caniato, R., Filippini, R., Cappelletti, E.M., 2002. In vivo and in vitro production of alkaloids by haplophyllum patavinum. Nat. Prod. Lett. 16, 95-100. https://doi: 10.1080/10575630290019985.
- Qin, F., Wang, C.Y., Kim, D., Wang, H.S., Zhu, Y.K., Lee, S.K., Yao, G.Y., Liang, D., 2020a. Nitidumpeptins A and B, cyclohexapeptides isolated from Zanthoxylum nitidum var. tomentosum: structural elucidation, total synthesis, and antiproliferative activity in cancer cells. J. Org. Chem. 86, 1462-1470. https://doi: 10.1021/acs.joc.0c02057.
- Qin, F., Wang, C.Y., Hu, R., Wang, C.G., Wang, F.F., Zhou, M.M., Liang, D., Liao, H.B., Lee, S.K., Wang, H.S., 2020b. Anti-inflammatory activity of isobutylamides from Zanthoxylum nitidum var. tomentosum. Fitoterapia 142, 104486. https://doi: 10.10 16/j.fitote.2020.104486.
- Qin, F., Wang, F.F., Wang, C.G., Chen, Y., Li, M.S., Zhu, Y.K., Huang, X.C., Fan, C.W., Wang, H.S., 2021. The neurotrophic and antineuroinflammatory effects of phenylpropanoids from Zanthoxylum nitidum var. tomentosum (Rutaceae). Fitoterapia 153, 104990. https://doi: 10.1016/j.fitote.2021.104990.
- Qin, F., Li, M.S., Li, J.J., Wang, Y., Liang, D., Wang, H.S., 2022. Four new sesquiterpenoids from Zanthoxylum nitidum. Chem. Biodivers. 2022, e202200449. https://doi: 10.1002/cbdv.202200449.
- Qing, Z.X., Yang, P., Yu, K., Yang, X.Y., Liu, J.H., Xiang, F., Cao, H.L., Cheng, P., Zeng, J. G., 2017. Mass spectrometry-guided isolation of two new dihydrobenzophenanthridine alkaloids from Macleaya cordata. Nat. Prod. Res. 31, 1-7. https://doi:10.1080/14786419.2017.1285300.
- Rapp, J., Jaromi, L., Kvell, K., Miskei, G., Pongracz, J.E., 2017. Wnt signaling-lung cancer is no exception. Respir. Res. 18, 1-16. https://doi: 10.1186/s12931-017-0650-6.
- Sichaem, J., Rojpitikul, T., Sawasdee, P., Lugsannangarm, K., Santi, T., 2015. Furoquinoline alkaloids from the leaves of evodia lepta as potential cholinesterase inhibitors and their molecular docking. Nat. Prod. Commun. 10, 1359-1362. https://doi: 10.1177/1934578x1501000811.
- Stewart, D.J., 2014. WNT signaling pathway in non-small cell lung cancer. J. Natl. Cancer Inst. 106, djt188. https://doi: 10.1093/jnci/djt356.
- Sukieum, S., Aroon, W.S., Yenjai, C., 2018. Coumarins and alkaloids from the roots of Toddalia asiatica. Nat. Prod. Res. 32, 944-952. https://doi:10.1080/14786419.201 7.1374264.
- Takahashi, Y.F., Kahn, M., 2010. Targeting Wnt signaling: can we safely eradicate cancer stem cells. Clin. Cancer Res. 16, 3153-3162. https://doi: 10.1158/1078-0432.ccr-0 9-2943.
- Thai, A.A., Solomon, B.J., Sequist, L.V., Gainor, J.F., Heist, R.S., 2021. Lung cancer. Lancet 398, 535-554. https://doi.org/10.1016/S0140-6736(21)00312-3.
- Wang, M.H., 1981. Isolation of antitumor alkaloids from Zanthoxylum nitidum and structure study of its alkaloid. Yaoxue Tongbao 16, 48.
- Wang, C.Y., Han, L., Kang, K., Shao, C.L., Wei, Y.X., Zheng, C.J., Guan, H.S., 2010. Secondary metabolites from green algae Ulva pertusa. Chem. Nat. Compd. 46, 828-830. https://doi: 10.1007/s10600-010-9760-9.
- Wangensteen, H., Ho, G.T.T., Tadesse, M., Miles, C.O., Moussavi, N., Mikolo, B., Malterud, K.E., 2016. A new benzophenanthridine alkaloid and other bioactive constituents from the stem bark of Zanthoxylum heitzii. Fitoterapia 109, 196-200. https://doi: 10.1016/j.fitote.2016.01.012.
- World Health Organization, 2020. International Agency for Research on Cancer Global Cancer Observatory: Cancer Today.
- Xu, X.H., Sun, P.L., Li, J.Z., Jheon, S.H., Lee, C.T., Chung, J.H., 2011. Aberrant Wnt1/ beta-catenin expression is an independent poor prognostic marker of non-small cell lung cancer after surgery. J. Thorac. Oncol. 6, 716-724. https://doi: 10.1097/j to.0b013e31820c5189.
- Yang, G., Chen, D., 2008. Alkaloids from the roots of Zanthoxylum nitidum and their antiviral and antifungal effects. Chem. Biodivers. 5, 1718-1722. https://doi:10. 1002/cbdv.200890160.