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Published in: Journal of Natural Medicines 1/2016

01-01-2016 | Note

ent-Atisane diterpenoids from Euphorbia fischeriana inhibit mammosphere formation in MCF-7 cells

Authors: Xinzhu Kuang, Wei Li, Yuichiro Kanno, Naoya Yamashita, Kiyomitsu Nemoto, Yoshihisa Asada, Kazuo Koike

Published in: Journal of Natural Medicines | Issue 1/2016

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Abstract

The discovery of new drugs that target cancer stem cells (CSCs) is a critical approach to overcome the major difficulties of the metastasis, chemotherapeutic resistance and recurrence for successful cancer therapy. Chemical investigation of the roots of Euphorbia fischeriana resulted in the isolation of eight ent-atisane diterpenoids (18), including two new compounds: 19-O-β-D-glucopyranosyl-ent-atis-16-ene-3,14-dione (7) and 19-O-(6-galloyl)-β-D-glucopyranosyl-ent-atis-16-ene-3,14-dione (8). The structures were elucidated on extensive spectroscopic analyses, as well as chemical transformations. ent-3β-Hydroxyatis-16-ene-2,14-dione (5), 7 and its aglycon, ent-19-hydroxy-atis-16-ene-3,14-dione (7a), showed significant inhibitory activity on mammosphere formation in human breast cancer MCF-7 cells at a final concentration of 10 μM.
Literature
1.
go back to reference Sun YX, Liu JC (2011) Chemical constituents and biological activities of Euphorbia fischeriana Steud. Chem Biodivers 8:1205–1214CrossRefPubMed Sun YX, Liu JC (2011) Chemical constituents and biological activities of Euphorbia fischeriana Steud. Chem Biodivers 8:1205–1214CrossRefPubMed
2.
go back to reference Wang YB, Huang R, Wang HB, Jin HZ, Lou LG, Qin GW (2006) Diterpenoids from the roots of Euphorbia fischeriana. J Nat Prod 69:967–970CrossRefPubMed Wang YB, Huang R, Wang HB, Jin HZ, Lou LG, Qin GW (2006) Diterpenoids from the roots of Euphorbia fischeriana. J Nat Prod 69:967–970CrossRefPubMed
3.
go back to reference Xu HY, Chen ZW, Hou JC, Du FX, Liu JC (2013) Jolkinolide B induces apoptosis in MCF-7 cells through inhibition of the PI3K/Akt/mTOR signaling pathway. Oncol Rep 29:212–218PubMed Xu HY, Chen ZW, Hou JC, Du FX, Liu JC (2013) Jolkinolide B induces apoptosis in MCF-7 cells through inhibition of the PI3K/Akt/mTOR signaling pathway. Oncol Rep 29:212–218PubMed
4.
go back to reference Wang JH, Zhou YJ, Bai X, He P (2011) Jolkinolide B from Euphorbia fischeriana Steud induces apoptosis in human leukemic U937 cells through PI3K/Akt and XIAP pathways. Mol Cells 32:451–457PubMedCentralCrossRefPubMed Wang JH, Zhou YJ, Bai X, He P (2011) Jolkinolide B from Euphorbia fischeriana Steud induces apoptosis in human leukemic U937 cells through PI3K/Akt and XIAP pathways. Mol Cells 32:451–457PubMedCentralCrossRefPubMed
5.
go back to reference Liu WK, Ho JCK, Qin G, Che CT (2002) Jolkinolide B induces neuroendocrine differentiation of human prostate LNCaP cancer cell line. Biochem Pharmacol 63:951–957CrossRefPubMed Liu WK, Ho JCK, Qin G, Che CT (2002) Jolkinolide B induces neuroendocrine differentiation of human prostate LNCaP cancer cell line. Biochem Pharmacol 63:951–957CrossRefPubMed
6.
go back to reference Kuang X, Li W, Kanno Y, Mochizuki M, Inouye Y, Koike K (2014) Cycloartane-type triterpenes from Euphorbia fischeriana stimulate human CYP3A4 promoter activity. Bioorg Med Chem Lett 24:5423–5427CrossRefPubMed Kuang X, Li W, Kanno Y, Mochizuki M, Inouye Y, Koike K (2014) Cycloartane-type triterpenes from Euphorbia fischeriana stimulate human CYP3A4 promoter activity. Bioorg Med Chem Lett 24:5423–5427CrossRefPubMed
7.
9.
go back to reference O’Connor ML, Xiang D, Shigdar S, Macdonald J, Li Y, Wang T, Pu C, Wang Z, Qiao L, Duan W (2014) Cancer stem cells: a contentious hypothesis now moving forward. Cancer Lett 344:180–187CrossRefPubMed O’Connor ML, Xiang D, Shigdar S, Macdonald J, Li Y, Wang T, Pu C, Wang Z, Qiao L, Duan W (2014) Cancer stem cells: a contentious hypothesis now moving forward. Cancer Lett 344:180–187CrossRefPubMed
10.
go back to reference Sotiropoulou PA, Christodoulou MS, Silvani A, Herold-Mende C, Passarella D (2014) Chemical approaches to targeting drug resistance in cancer stem cells. Drug Discov Today 19:1547–1562CrossRefPubMed Sotiropoulou PA, Christodoulou MS, Silvani A, Herold-Mende C, Passarella D (2014) Chemical approaches to targeting drug resistance in cancer stem cells. Drug Discov Today 19:1547–1562CrossRefPubMed
12.
go back to reference Zhao S, Kanno Y, Nakayama M, Makimura M, Ohara S, Inouye Y (2012) Activation of the aryl hydrocarbon receptor represses mammosphere formation in MCF-7 cells. Cancer Lett 317:192–198CrossRefPubMed Zhao S, Kanno Y, Nakayama M, Makimura M, Ohara S, Inouye Y (2012) Activation of the aryl hydrocarbon receptor represses mammosphere formation in MCF-7 cells. Cancer Lett 317:192–198CrossRefPubMed
13.
go back to reference Lal AR, Cambie RC, Rutledge PS, Woodgate PD, Rickard CEF, Clark GR (1989) New oxidised ent-atisene diterpenes from Euphorbia fidjiana. Tetrahedron Lett 30:3205–3208CrossRef Lal AR, Cambie RC, Rutledge PS, Woodgate PD, Rickard CEF, Clark GR (1989) New oxidised ent-atisene diterpenes from Euphorbia fidjiana. Tetrahedron Lett 30:3205–3208CrossRef
14.
go back to reference Lal AR, Cambie RC, Rutledge PS, Woodgate PD (1990) Chemistry of Fijian plants. Part 4. ent-Atisane diterpenes from Euphorbia fidjiana. Phytochemistry 29:1925–1935CrossRef Lal AR, Cambie RC, Rutledge PS, Woodgate PD (1990) Chemistry of Fijian plants. Part 4. ent-Atisane diterpenes from Euphorbia fidjiana. Phytochemistry 29:1925–1935CrossRef
15.
go back to reference He F, Pu JX, Huang SX, Xiao WL, Yang LB, Li XN, Zhao Y, Ding J, Xu CH, Sun HD (2008) Eight new diterpenoids from the roots of Euphorbia nematocypha. Helv Chim Acta 91:2139–2147CrossRef He F, Pu JX, Huang SX, Xiao WL, Yang LB, Li XN, Zhao Y, Ding J, Xu CH, Sun HD (2008) Eight new diterpenoids from the roots of Euphorbia nematocypha. Helv Chim Acta 91:2139–2147CrossRef
16.
go back to reference Gustafson KR, Munro MHG, Blunt JW, Cardellina JH, McMahon JB, Gulakowski RJ, Cragg GM, Cox PA, Brinen LS, Clardy J, Boyd MR (1991) HIV inhibitory natural products. 3. Diterpenes from Homalanthus acuminatus and Chrysobalanus icaco. Tetrahedron 47:4547–4554CrossRef Gustafson KR, Munro MHG, Blunt JW, Cardellina JH, McMahon JB, Gulakowski RJ, Cragg GM, Cox PA, Brinen LS, Clardy J, Boyd MR (1991) HIV inhibitory natural products. 3. Diterpenes from Homalanthus acuminatus and Chrysobalanus icaco. Tetrahedron 47:4547–4554CrossRef
17.
go back to reference Zhang BY, Wang H, Luo XD, Du ZZ, Shen JW, Wu HF, Zhang XF (2012) Bisyinshanic acids A and B, two novel diterpene dimers from the roots of Euphorbia yinshanica. Helv Chim Acta 95:1672–1679CrossRef Zhang BY, Wang H, Luo XD, Du ZZ, Shen JW, Wu HF, Zhang XF (2012) Bisyinshanic acids A and B, two novel diterpene dimers from the roots of Euphorbia yinshanica. Helv Chim Acta 95:1672–1679CrossRef
18.
go back to reference Shi HM, Williams ID, Sung HH, Zhu HX, Ip NY, Min ZD (2005) Cytotoxic diterpenoids from the roots of Euphorbia ebracteolata. Planta Med 71:349–354CrossRefPubMed Shi HM, Williams ID, Sung HH, Zhu HX, Ip NY, Min ZD (2005) Cytotoxic diterpenoids from the roots of Euphorbia ebracteolata. Planta Med 71:349–354CrossRefPubMed
19.
go back to reference Abad A, Agulló C, Cuñat AC, de Alfonso Marzal I, Gris A, Navarro I, de Arellano CR (2007) Diastereoselective synthesis of antiquorin and related polyoxygenated atisene-type diterpenes. Tetrahedron 63:1664–1679CrossRef Abad A, Agulló C, Cuñat AC, de Alfonso Marzal I, Gris A, Navarro I, de Arellano CR (2007) Diastereoselective synthesis of antiquorin and related polyoxygenated atisene-type diterpenes. Tetrahedron 63:1664–1679CrossRef
20.
go back to reference Li W, Asada Y, Koike K, Nikaido T, Furuya T, Yoshikawa T (2005) Bellisosides A–F, six novel acylated triterpenoid saponins from Bellis perennis (compositae). Tetrahedron 61:2921–2929CrossRef Li W, Asada Y, Koike K, Nikaido T, Furuya T, Yoshikawa T (2005) Bellisosides A–F, six novel acylated triterpenoid saponins from Bellis perennis (compositae). Tetrahedron 61:2921–2929CrossRef
Metadata
Title
ent-Atisane diterpenoids from Euphorbia fischeriana inhibit mammosphere formation in MCF-7 cells
Authors
Xinzhu Kuang
Wei Li
Yuichiro Kanno
Naoya Yamashita
Kiyomitsu Nemoto
Yoshihisa Asada
Kazuo Koike
Publication date
01-01-2016
Publisher
Springer Japan
Published in
Journal of Natural Medicines / Issue 1/2016
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-015-0940-6

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