Cytotoxic activities of sesquiterpenoids from the aerial parts of Petasites japonicus against cancer stem cells.
Cancer stem cell
ECD
Petasites japonicus
Petasitesterpene
Journal
Journal of natural medicines
ISSN: 1861-0293
Titre abrégé: J Nat Med
Pays: Japan
ID NLM: 101518405
Informations de publication
Date de publication:
Sep 2020
Sep 2020
Historique:
received:
21
04
2020
accepted:
02
06
2020
pubmed:
15
6
2020
medline:
7
10
2020
entrez:
15
6
2020
Statut:
ppublish
Résumé
From the methanolic extract of the aerial parts of Petasites japonicus, six new eremophilane-type sesquiterpenoids, petasitesterpenes I-VI were isolated together with eight known compounds including S-japonin and eremophilenolide. The chemical structures of the isolated new compounds were elucidated based on chemical/physicochemical evidence. For petasitesterpenes I and II, the absolute configurations were established by comparison of experimental and predicted electronic circular dichroism (ECD) data. Among the isolated compounds, petasitesterpenes I, II, VI, and S-japonin showed cytotoxic activity against both human astrocytoma U-251MG cancer cells (non-CSCs) and their cancer stem cells (CSCs) isolated by sphere formation. In addition, cytotoxic activities of these compounds against breast cancer MDA-MB-231 were evaluated, supporting that petasitesterpene II has more effective than other isolated compounds.
Identifiants
pubmed: 32535872
doi: 10.1007/s11418-020-01420-x
pii: 10.1007/s11418-020-01420-x
doi:
Substances chimiques
Sesquiterpenes
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
689-701Subventions
Organisme : Japan Society for the Promotion of Science
ID : JP17K15473
Organisme : Japan Society for the Promotion of Science
ID : JP20H03397
Références
Naya K, Kawai M, Naito M, Kasai T (2019) The structure of eremofukinone, 9-acetoxyfukinanolide and S-japonin from Petasites japonicus MAXIM. Chem Lett 1:241–244
doi: 10.1246/cl.1972.241
Kitajima M, Okabe K, Yoshida M, Nakabayashi R, Saito K, Kogure N, Takayama H (2019) New otonecine-type pyrrolizidine alkaloid from Petasites japonicus. J Nat Med 73:602–607
doi: 10.1007/s11418-019-01285-9
Yoshikawa M, Morikawa T, Tanaka J, Shimoda H (2006) Medicinal Foodstuffs. XXXII. Novel Sesquiterpene Glycoside Sulfate, Fukinoside A, with Antiallergic Activity from Japanese Butterbur (Petasites japonicus). Heterocycles 68:2335–2342
doi: 10.3987/COM-06-10858
Bodensieck A, Gaunitz F, Gebhardt R, Danesch U, Bauer R (2007) New eremophilane sesquiterpenes from a rhizome extract of Petasites hybridus. Helv Chim Acta 90:183–195
doi: 10.1002/hlca.200790014
Goto Y, Kojima Y, Nakayama T, Terazawa M (2001) Allelopathic sesquiterpenoids from rhizomes of Petasites japonicus ssp. giganteus Kitam. Phytochemistry 57:109–113
doi: 10.1016/S0031-9422(00)00506-9
Fei DQ, Li SG, Liu CM, Wu G, Gao K (2007) Eremophilane-type sesquiterpene derivatives from the roots of Ligularia lapathifolia. J Nat Prod 70:241–245
doi: 10.1021/np060304k
Adachi Y, Kanbayashi Y, Harata I, Ubagai R, Takimoto T, Suzuki K, Miwa T, Noguchi Y (2014) Petasin activates AMP-activated protein kinase and modulates glucose metabolism. J Nat Prod 77:1262–1269
doi: 10.1021/np400867m
Mitsui T, Hayashi K, Kawai M, Kido M, Tani H, Takaoka D, Matsuura N, Nozaki H (2013) Culcitiolides E-J, six new eremophilane-type sesquiterpene derivatives from senecio culcitioides. Chem Pharm Bull 61:816–822
doi: 10.1248/cpb.c13-00243
Chang JC, Hsiao G, Lin RK, Kuo YH, Ju YM, Lee TH (2017) Bioactive constituents from the termite nest-derived medicinal fungus Xylaria nigripes. J Nat Prod 80:38–44
doi: 10.1021/acs.jnatprod.6b00249
Liu J, Zhang D, Zhang M, Zhao J, Chen R, Wang N, Zhang D, Dai J (2016) Eremophilane sesquiterpenes from an endophytic fungus Periconia Species. J Nat Prod 79:2229–2235
doi: 10.1021/acs.jnatprod.6b00299
Wang S, Jin DQ, Xie C, Wang H, Wang M, Xu J, Guo Y (2013) Isolation, characterization, and neuroprotective activities of sesquiterpenes from Petasites japonicus. Food Chem 141:2075–2082
doi: 10.1016/j.foodchem.2013.04.116
Matsumoto T, Imahori D, Achiwa K, Saito Y, Ohta T, Yoshida T, Kojima N, Yamashita M, Nakayama Y, Watanabe T (2020) Chemical structures and cytotoxic activities of the constituents isolated from Hibiscus tiliaceus. Fitoterapia 142:104524
doi: 10.1016/j.fitote.2020.104524
Matsumoto T, Kitagawa T, Teo S, Anai Y, Ikeda R, Imahori D, Ahmad HS, Watanabe T (2018) Structures and antimutagenic effects of onoceranoid-type triterpenoids from the leaves of Lansium domesticum. J Nat Prod 81:2187–2194
doi: 10.1021/acs.jnatprod.8b00341
Matsumoto T, Kitagawa T, Ohta T, Yoshida T, Imahori D, Teo S, Ahmad HS, Watanabe T (2019) Structures of triterpenoids from the leaves of Lansium domesticum. J Nat Med 73:727–734
doi: 10.1007/s11418-019-01319-2
Matsumoto T, Nakamura S, Kojima N, Hasei T, Yamashita M, Watanabe T, Matsuda H (2017) Antimutagenic activity of ent-kaurane diterpenoids from the aerial parts of Isodon japonicus. Tetrahedron Lett 58:3574–3578
doi: 10.1016/j.tetlet.2017.07.106
Matsumoto T, Takahashi K, Kanayama S, Nakano Y, Imai H, Kibi M, Imahori D, Hasei T, Watanabe T (2017) Structures of antimutagenic constituents in the peels of Citrus limon. J Nat Med 71:735–744
doi: 10.1007/s11418-017-1108-3
Matsumoto T, Koike M, Arai C, Kitagawa T, Inoue E, Imahori D, Watanabe T (2018) Chemical structures and antimutagenic effects of unusual oximes from the peels of Citrus limon. Phytochem Lett 25:118–121
doi: 10.1016/j.phytol.2018.04.016
Singh SK, Clarke ID, Terasaki M, Bonn VE, Hawkins C, Squire J, Dirks PB (2003) Identification of a cancer stem cell in human brain tumors. Cancer Res 15:5821–5828
Hemmati HD, Nakano I, Lazareff JA, Masterman-Smith M, Geschwind DH, Bronner-Fraser M, Kornblum HI (2003) Cancerous stem cells can arise from pediatric brain tumors. Proc Natl Acad Aci U S A 100:15178–15183
doi: 10.1073/pnas.2036535100
Pasikanti S, Reddy DS, Iqbal J, Dubey PK, Das P (2009) Total synthesis of (±)-petasitolone and (±)-fukinone. Synthesis 22:3833–3837
Green R, Howell M, Khalil R, Nair R, Yan J, Foran E, Katiri S, Banerjee J, Singh M, Bharadwaj S, Mohapatra SS, Mohapatra S (2019) Actinomycin D and telmisartan combination targets lung cancer stem cells through the Wnt/beta catenin pathway. Sci Rep 9:18177–18189
doi: 10.1038/s41598-019-54266-z
Wang WS, Gao K, Yang L, Jia ZJ (2000) Eremophilenolides from Ligularia fischeri. Planta Med 66:191–198
doi: 10.1055/s-0029-1243132
Naya K, Shimizu M, Nishio H, Takeda M, Oka S, Hirota K (1991) The photosensitized oxygenation of furanoeremophilanes. III. The transformations to the skeletally isomeric lactones from furanofukinol. Bull Chem Soc Jpn 64:1071–1080
doi: 10.1246/bcsj.64.1071
Naya K, Yoshimura F, Takagi I (1971) The structure of petasitolone, a new constituent of Petasites japonicus Maxim. Bull Chem Soc Jpn 44:3165–3167
doi: 10.1246/bcsj.44.3165
Nakamura S, Fujimoto K, Matsumoto T, Nakashima S, Ohta T, Ogawa K, Matsuda H, Yoshikawa M (2013) Acylated sucroses and acylated quinic acids analogs from the flower buds of Prunus mume and their inhibitory effect on melanogenesis. Phytochemistry 92:128–136
doi: 10.1016/j.phytochem.2013.04.012
Bodensieck A, Fabian WM, Kunert O, Belaj F, Jahangir S, Schühly W, Bauer R (2010) Absolute configuration of eremophilane sesquiterpenes from Petasites hybridus: comparison of experimental and calculated circular dichroism spectra. Chirality 22:308–319
pubmed: 19496156
Takada T, Takata K, Ashihara E (2016) Inhibition of monocarboxylate transporter 1 suppresses the proliferation of glioblastoma stem cells. J Physiol Sci 66:387–396
doi: 10.1007/s12576-016-0435-6
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski, JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford, CT
Bruhn T, Schaumlöffel A, Hemberger Y, Pecitelli G (2013) SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25:243–249
doi: 10.1002/chir.22138