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Planta Med 2012; 78(12): 1370-1377
DOI: 10.1055/s-0032-1314975
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Cycloartane Triterpenes and Ingol Diterpenes Isolated from Euphorbia neriifolia in a Screening Program for Death-Receptor Expression-Enhancing Activity

Kazufumi Toume
1   Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan
,
Takafumi Nakazawa
1   Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan
,
Tahmina Hoque
1   Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan
,
Takashi Ohtsuki
1   Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan
,
Midori A. Arai
1   Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan
,
Takashi Koyano
2   Temko Corporation, Tokyo, Japan
,
Thaworn Kowithayakorn
3   Faculty of Agriculture, Khon Kaen University, Chiba, Japan
,
Masami Ishibashi
1   Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan
› Author Affiliations
Further Information

Publication History

received 17 January 2012
revised 14 May 2012

accepted 21 May 2012

Publication Date:
14 June 2012 (online)

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Abstract

In our screening program for natural products that increase death-receptor 5 expression, seven new cycloartane triterpenes, euphonerins A–G (1–7), and 3-O-acetyl-8-O-tigloylingol (8), a new ingol diterpene, were isolated from the MeOH extract of Euphorbia neriifolia leaves, together with 3,12-di-O-acetyl-8-O-tigloylingol (9), (24R)-cycloartane-3β,24,25-triol (10), and three known flavonols (11–13). The structures of 1–8 were elucidated by spectroscopic analysis. Among these compounds, 1–11 showed death-receptor 5 expression enhancing activity.

Key words

Euphorbia neriifolia - Euphorbiaceae - cycloartane triterpene - ingol diterpene - death receptor - TRAIL

Supporting Information

 

  • References

  • 1 Ishibashi M, Ohtsuki T. Studies on search for bioactive natural products targeting TRAIL signaling leading to tumor cell apoptosis. Med Res Rev 2008; 28: 688-714
    CrossrefPubMedSearch in Google Scholar
  • 2 Ishibashi M, Arai MA. Search for bioactive natural products targeting cancer-related signaling pathways. J Synth Org Chem Jpn 2009; 67: 1094-1104
    CrossrefPubMedSearch in Google Scholar
  • 3 Ahmed F, Toume K, Sadhu SK, Ohtsuki T, Arai MA, Ishibashi M. Constituents of Amoora cucullata with TRAIL resistance-overcoming activity. Org Biomol Chem 2010; 8: 3696-3703
    CrossrefPubMedSearch in Google Scholar
  • 4 Toume K, Nakazawa T, Ohtsuki T, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M. Cycloartane triterpenes isolated from Combretum quadrangulare in a screening program for death-receptor expression enhancing activity. J Nat Prod 2011; 74: 249-255
    CrossrefPubMedSearch in Google Scholar
  • 5 Ahmed SA, Nazim S, Siraj S, Siddik PM, Wahid CA. Euphorbia neriifolia Linn: A phytopharmacological review. Int Res J Pharm 2011; 2: 41-48
    PubMedSearch in Google Scholar
  • 6 Ng AS. Diterpenes from Euphorbia neriifolia . Phytochemistry 1990; 29: 662-664
    CrossrefPubMedSearch in Google Scholar
  • 7 Mallavadhani UV, Satyanarayana KVS, Mahapatra A, Sudhakar AVS. A new tetracyclic triterpene from the latex of Euphorbia nerifolia . Nat Prod Res 2004; 18: 33-37
    CrossrefPubMedSearch in Google Scholar
  • 8 Ilyas M, Parveen M, Mohammad K, Amin Y. Neriifolione, a triterpene from Euphorbia neriifolia . Phytochemistry 1998; 48: 561-563
    CrossrefPubMedSearch in Google Scholar
  • 9 Kikuchi H, Ohtsuki T, Koyano T, Kowithayakorn T, Sakai T, Ishibashi M. Brandisianins A–F, isoflavonoids isolated from Millettia brandisiana in a screening program for death-receptor expression enhancement activity. J Nat Prod 2007; 70: 1910-1914
    CrossrefPubMedSearch in Google Scholar
  • 10 Yoshida T, Maeda A, Tani N, Sakai T. Promoter structure and transcription initiation sites of the human death receptor 5/TRAIL-R2 gene. FEBS Lett 2001; 507: 381-385
    CrossrefPubMedSearch in Google Scholar
  • 11 Lindhagen E, Nygren P, Larsson R. The fluorometric microculture cytotoxicity assay. Nat Protoc 2008; 3: 1364-1369
    CrossrefPubMedSearch in Google Scholar
  • 12 Ahmed F, Ohtsuki T, Aida W, Ishibashi M. Tyrosine derivatives isolated from Streptomyces sp. IFM 10937 in a screening program for TRAIL-resistance-overcoming activity. J Nat Prod 2008; 71: 1963-1966
    CrossrefPubMedSearch in Google Scholar
  • 13 Cheng SY, Wen ZH, Wang SK, Chiang MY, El-Gamal AA, Dai CF, Duh CY. Revision of the absolute configuration at C(23) of lanostanoids and isolation of secondary metabolites from formosan soft coral Nephthea erecta . Chem Biodivers 2009; 6: 86-95
    CrossrefPubMedSearch in Google Scholar
  • 14 Mohamad K, Martin MT, Leroy E, Tempete C, Sevenet T, Awang K, Pais M. Argenteanones C–E and argenteanols B–E, cytotoxic cycloartanes from Aglaia argentea . J Nat Prod 1997; 60: 81-85
    CrossrefPubMedSearch in Google Scholar
  • 15 Herz W, Watanabe K, Kulanthaivel P, Blount JF. Cycloartanes from Lindheimera texana . Phytochemistry 1985; 24: 2645-2654
    CrossrefPubMedSearch in Google Scholar
  • 16 Ahmed AA, Couladis M, Mahmoud AA, De Adams A, Mabry TJ. Ingol diterpene ester from the latex of Euphorbia lactea . Fitoterapia 1999; 70: 140-143
    CrossrefPubMedSearch in Google Scholar
  • 17 Della Greca M, Fiorentino A, Monaco P, Previtera L. Cycloartane triterpenes from Juncus effusus . Phytochemistry 1994; 35: 1017-1022
    CrossrefPubMedSearch in Google Scholar
  • 18 Ariyanathan S, Saraswathy A, Rajamanickam GV, Connolly JD. Polyphenols from the roots of Plumbago rosea . Indian J Chem 2010; 49?B: 386-389
    PubMedSearch in Google Scholar
  • 19 Sy L, Brown GD. Three sesquiterpenes from Artemisia annua . Phytochemistry 1998; 48: 1207-1211
    CrossrefPubMedSearch in Google Scholar
  • 20 Dachriyanus Fahmi R, Sargent MV, Skelton BW, White AH. 5-Hydroxy-3, 3′,4′,5′,7-pentamethoxyflavone (combretol). Acta Crystallogr 2004; E60: o86-o88
    PubMedSearch in Google Scholar
  • 21 Horinaka M, Yoshida T, Shiraishi T, Nakata S, Wakada M, Nakanishi R, Nishino H, Matsui H, Sakai T. Luteolin induces apoptosis via death receptor 5 upregulation in human malignant tumor cells. Oncogene 2005; 24: 7180-7189
    CrossrefPubMedSearch in Google Scholar
  • 22 Horinaka M, Yoshida T, Shiraishi T, Nakata S, Wakada M, Nakanishi R, Nishino H, Sakai T. The combination of TRAIL and luteolin enhances apoptosis in human cervical cancer HeLa cells. Biochem Biophys Res Commun 2005; 333: 833-838
    CrossrefPubMedSearch in Google Scholar