Abstract
To explore useful natural compounds from indigenous medicinal plants, the cytotoxic properties from a methanolic extract of Boehmeria sieboldiana leaves against human cancer cell lines were isolated in the present study. After purification of the extract, seco-dehydroantofine B (1) together with two known phenanthroindolizine alkaloids, seco-dehydroantofine A (2) and septicine (3), were isolated. The structure of seco-dehydroantofine B was elucidated by performing comprehensive one- and two-dimensional nuclear magnetic resonance spectroscopy and high-resolution electrospray ionization mass spectrometry. The cytotoxicity of these compounds against five human tumor cell lines was evaluated. Compound 3 exhibited anti-tumor activity at IC50 values of 50.0, 66.9, 50.0, and 153.7 µM against MKN1, SAS, HL-60, and THP-1 cells, respectively.
References
Adianti M, Aoki C, Komoto M, Deng L, Shoji I, Wahyuni TS, Lusida MI, Soetjipto FH, Kawahara N, Hotta H (2014) Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species. Microbiol Immunol 58:180–187
Yahara Y, Takemori H, Okada M, Kosai A, Yamashita A, Kobayashi T, Fujita K, Itoh Y, Nakamura M, Fuchino H, Kawahara N, Fukui N, Watanabe A, Kimura T, Tsumaki N (2016) Pterosin B prevents chondrocyte hypertrophy and osteoarthritis in mice by inhibiting Sik3. Nat Commun 7:10959
Arita M, Fuchino H, Kawakami H, Ezaki M, Kawahara N (2020) Characterization of a new antienterovirus D68 compound purified from avocado. ACS Infect Dis 6:2291–2300
“The Plant List” http://www.theplantlist.org/tpl1.1/record/kew-2678457, cited 20 Dec, 2021
Rosariastuti E, Barokah U, Purwanto P, Supriyadi S (2018) Phytoremediation of Pb contaminated paddy field using combination of Agrobacterium sp. I3, compost and ramie (Boehmeria nivea). J Degrade Min Land Manage 5:1381–1388
Xu QM, Liu YL, Li XR, Li XY, Yang SL (2011) Three new fatty acids from the roots of Boehmeria nivea (L.) Gaudich and their antifungal activities. Nat Prod Res 25:640–647
Lin CC, Yen MH, Lo TS, Lin CF (1997) The antiinflammatory and liver protective effects of Boehmeria nivea and B. nivea subsp. nippononiveain rats. Phytomedicine 4:301–308
Sung MJ, Davaatseren M, Kim SH, Kim MJ, Hwang JT (2013) Boehmeria nivea attenuates LPS-induced inflammatory markers by inhibiting p38 and JNK phosphorylations in RAW264.7 macrophages. Pharm Biol 51:1131–1136
DH Park, J Lee, SR Heo (2009) Boehmeria sieboldiana extracts for preventing and treating alopecia. Korean Patent KR2009052735, 26 May
SC Kim, ES Jung, DH Park (2014) Boehmeria sieboldiana extract for preventing and treating obesity. Korean Patent KR2014050436, 29 April
Kubo M, Yatsuzuka W, Matsushima S, Harada K, Inoue Y, Miyamoto H, Matsumoto M, Fukuyama Y (2016) Antimalarial phenanthroindolizine alkaloids from Ficus septica. Chem Pharm Bull (Tokyo) 64:957–960
Comins DL, Chen X, Morgan LA (1997) Enantiopure N-acyldihydropyridones as synthetic intermediates: asymmetric synthesis of (−)-septicine and (−)-tylophorine. J Org Chem 62:7435–7438
Ciufolini MA, Roschangar F (1996) A unified strategy for the synthesis of phenanthroizidine alkaloids: preparation of sterically congested pyridines. J Am Chem Soc 118:12082–12089
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Matsuo, H., Kawakami, H., Anjiki, N. et al. Phenanthroindolizine alkaloids from Boehmeria sieboldiana leaves exhibit cytotoxicity against human cancer cell lines. J Nat Med 76, 670–674 (2022). https://doi.org/10.1007/s11418-022-01610-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11418-022-01610-9