nach oben

Erschienen in:

21.03.2016 | Original Paper

Euphorins A–H: bioactive diterpenoids from Euphorbia fischeriana

verfasst von: Xinzhu Kuang, Wei Li, Yuichiro Kanno, Naoya Yamashita, Shoko Kikkawa, Isao Azumaya, Kiyomitsu Nemoto, Yoshihisa Asada, Kazuo Koike

Erschienen in: Journal of Natural Medicines | Ausgabe 3/2016

Einloggen, um Zugang zu erhalten

Abstract

Phytochemical investigation of the roots of Euphorbia fischeriana resulted in the isolation of 23 diterpenoids (1–23), which were classified into five subtypes, namely, ent-rosane (1–9), ent-abietane (10–16), ent-kaurane (17), ingenane (18–22), and lathyrane (23). The chemical structures of eight new compounds, namely, euphorin A (4), B (5), C (7), D (9), E (13), F (14), G (15), and H (16), were elucidated on the basis of extensive 1D and 2D NMR spectroscopic analyses, as well as single crystal X-ray structure analysis. A number of compounds (2, 6, 7, 10, 11, 13, 16, 19, 20, 22, and 23) showed inhibitory activity on the formation of mammospheres in human breast cancer MCF-7 cells at a final concentration of 10 μM, suggesting the potential of these bioactive diterpenoids for further investigation of the action targeting cancer stem cells.

Asada Y, Sukemori A, Watanabe T, Malla KJ, Yoshikawa T, Li W, Koike K, Chen CH, Akiyama T, Qian K, Nakagawa-Goto K, Morris-Natschke SL, Lee KH (2011) Stelleralides A–C, novel potent anti-HIV daphnane-type diterpenoids from Stellera chamaejasme L. Org Lett 13:2904–2907CrossRefPubMedPubMedCentral

Sasaki T, Li W, Zaike S, Asada Y, Li Q, Ma F, Zhang Q, Koike K (2013) Antioxidant lignoids from leaves of Ribes nigrum. Phytochemistry 95:333–340CrossRefPubMed

Li D, Li W, Higai K, Koike K (2014) Protein tyrosine phosphatase 1B inhibitory activities of ursane- and lupane-type triterpenes from Sorbus pohuashanensis. J Nat Med 68:427–431CrossRefPubMed

Sasaki T, Li W, Higai K, Koike K (2015) Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors. Bioorg Med Chem Lett 25:1979–1981CrossRefPubMed

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, Yamashita N, Nemoto K, Asada Y, Koike K (2016) ent-Atisane diterpenoids from Euphorbia fischeriana inhibit mammosphere formation in MCF-7 cells. J Nat Med 70:120–126CrossRefPubMed

Traditional Chinese Medicine Dictionary; Pergamon: Shanghai Scientific and Technical Publishers, (1985) 4:5651–5653

Shi QW, Su XH, Kiyota H (2008) Chemical and pharmacological research of the plants in genus Euphorbia. Chem Rev 108:4295–4327CrossRefPubMed

Vasas A, Hohmann J (2014) Euphorbia diterpenes: isolation, structure, biological activity, and synthesis (2008–2012). Chem Rev 114:8579–8612CrossRefPubMed

10.

Wang HB, Wang XY, Liu LP, Qin GW, Kang TG (2015) Tigliane diterpenoids from the Euphorbiaceae and Thymelaeaceae families. Chem Rev 115:2975–3011CrossRefPubMed

11.

Butler MS, Robertson AA, Cooper MA (2014) Natural product and natural product derived drugs in clinical trials. Nat Prod Rep 31:1612–1661CrossRefPubMed

12.

Sun YX, Liu JC (2011) Chemical constituents and biological activities of Euphorbia fischeriana Steud. Chem Biodivers 8:1205–1214CrossRefPubMed

13.

Nagashima F, Sekiguchi T, Takaoka S, Asakawa Y (2004) Terpenoids and aromatic compounds from the New Zealand liverworts Plagiochila, Schistochila, and Heteroscyphus species. Chem Pharm Bull (Tokyo) 52:556–560CrossRef

14.

Liu ZG, Li ZL, Bai J, Meng DL, Li N, Pei YH, Zhao F, Hua HM (2014) Anti-inflammatory diterpenoids from the roots of Euphorbia ebracteolata. J Nat Prod 77:792–799CrossRefPubMed

15.

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

16.

Pei Y, Koike K, Han B, Jia Z, Nikaido T (1999) Fischeria A, a novel norditerpene lactone from Euphorbia fischeriana. Tetrahedron Lett 40:951–952CrossRef

17.

Uemura D, Hirata Y (1972) Two new diterpenoids, jolkinolides A and B, obtained from Euphorbia jolkini Boiss (Euphorbiaceae). Tetrahedron Lett 13:1387–1390CrossRef

18.

Lal AR, Cambie RC, Rutledge PS, Woodgate PD (1990) Chemistry of Fijian plants. Part 6. ent-Pimarane and ent-abietane diterpenes from Euphorbia fidjiana. Phytochemistry 29:2239–2246CrossRef

19.

Liu G, Müller R, Rüedi P (2003) Chemical transformations of phyllocladane (=13β-kaurane) diterpenoids. Helv Chim Acta 86:420–438CrossRef

20.

Ding Y, Jia Z (1991) Tetracyclic diterpenols from Euphorbia sieboldiana. Phytochemistry 30:2413–2415CrossRef

21.

Jia Z, Ding Y (1991) New Diterpenoids from Euphorbia sieboldiana. Planta Med 57:569–571CrossRefPubMed

22.

Sorg B, Hecker E (1982) On the chemistry of ingenol. II. Esters of ingenol and Δ7,8-isoingenol. Z Naturforsch B Chem Sci 37B:748–756

23.

Uemura D, Nobuhara K, Nakayama Y, Shizuri Y, Hirata Y (1976) The structure of new lathyrane diterpenes, jolkinols A, B, C, and D, from Euphorbia jolkini Boiss. Tetrahedron Lett 17:4593–4596CrossRef

24.

Clevers H (2011) The cancer stem cell: premises, promises and challenges. Nat Med 17:313–319CrossRefPubMed

25.

Greaves M (2011) Cancer stem cells renew their impact. Nat Med 17:1046–1048CrossRefPubMed

26.

Pattabiraman DR, Weinberg RA (2014) Tackling the cancer stem cells—what challenges do they pose? Nat Rev Drug Discov 13:497–512CrossRefPubMedPubMedCentral

27.

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

28.

Altmomare A, Burla MC, Camalli M, Cascarano M, Giacovazzo C, Guagliardi A, Polidori G (1994) SIR92—a program for automatic solution of crystal structure by direct method. J Appl Crystallogr 27:435

29.

Sheldrick GM (2008) A short history of SHELX. Acta Crystallogr A 64:112–122CrossRefPubMed

Titel: Euphorins A–H: bioactive diterpenoids from Euphorbia fischeriana
verfasst von: Xinzhu Kuang
Wei Li
Yuichiro Kanno
Naoya Yamashita
Shoko Kikkawa
Isao Azumaya
Kiyomitsu Nemoto
Yoshihisa Asada
Kazuo Koike
Publikationsdatum: 21.03.2016
Verlag: Springer Japan
Erschienen in: Journal of Natural Medicines / Ausgabe 3/2016
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-016-0987-z

Springer Medizin

Abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Weitere Artikel der Ausgabe 3/2016

Efficient expression of single chain variable fragment antibody against paclitaxel using the Bombyx mori nucleopolyhedrovirus bacmid DNA system and its characterizations

Protective effects of Weilikang decoction on gastric ulcers and possible mechanisms

Characterization of α-humulene synthases responsible for the production of sesquiterpenes induced by methyl jasmonate in Aquilaria cell culture

Development of crossbreeding high-yield-potential strains for commercial cultivation in the medicinal mushroom Wolfiporia cocos (Higher Basidiomycetes)

Lucidumol C, a new cytotoxic lanostanoid triterpene from Ganoderma lingzhi against human cancer cells

Epigallocatechin gallate inhibits hepatitis B virus via farnesoid X receptor alpha