Biotransformation of ingenol-3-angelate in four plant cell suspension cultures

References

• Adolf W, Chanai S, Hecker E. 3-O-Angeloylingenol, the toxic and skin irritant factor from latex of Euphorbia anitiquorum L. (Euphorbiaceae) and from a derived Thai pugative and anthelimintic (vermifuge) drug. J Sci Soc Thai 1983; 9: 81–88
   Google Scholar
• Appendino, G, Tron, GC, Cravotto, G, Palmisano, G, Annunziata, R, Baj, G, Surico, N. 1999. Synthesis of modified ingenol esters. Eur J Org Chem. 3413–3420.
   Web of Science ®Google Scholar
• Bicchi C, Appendino G, Cordero C, Rubiolo P, Ortelli D, Veuthey JL. HPLC–UV and HPLC–positive-ESI-MS analysis of the diterpenoid fraction from caper spurge (Euphorbia lathyris) seed oil. Phytochem Anal 2001; 12: 255–262
   Google Scholar
• Broomhead AJ, Dewick PM. Biotransformation of podophyllum lignans in cell-suspension cultures of Forsythia intermedia. Phytochemistry 1991; 30: 1511–1517
   Web of Science ®Google Scholar
• Challacombe JM, Suhrbier A, Parsons PG, Jones B, Hampson P, Kavanagh D, Rainger GE, Morris M, Lord JM, Le TT, Hoang-Le D, Ogbourne SM. Neutrophils are a key component of the antitumor efficacy of topical chemotherapy with ingenol-3-angelate. J Immunol 2006; 177: 8123–8132
   PubMed Web of Science ®Google Scholar
• Connolly JD, Fakunle CO, Rycroft DS. 5 Ingol esters and a 17-hydroxyingenol ester from the latex of Euphorbia kamerunica – assignment of esters using C-13 NMR methods. Tetrahedron Lett 1984; 25: 3773–3776
   Web of Science ®Google Scholar
• Fujiwara M, Ijichi K, Tokuhisa K, Katsuura K, Wang GYS, Uemura D, Shigeta S, Konno K, Yokota T, Baba M. Ingenol derivatives are highly potent and selective inhibitors of HIV replication in vitro. Antivir Chem Chemother 1996; 7: 230–236
   Web of Science ®Google Scholar
• Hampson P, Chahal H, Khanim F, Hayden R, Mulder A, Assi LK, Bunce CM, Lord JM. PEP005, a selective small-molecule activator of protein kinase C, has potent antileukemic activity mediated via the delta isoform of PKC. Blood 2005a; 106: 1362–1368
   PubMed Web of Science ®Google Scholar
• Hampson P, Wang K, Lord JM. PEP-005 – treatment of actinic keratoses acute myeloid leukemia therapy treatment of basal cell carcinoma protein kinase C activator. Drug Future 2005b; 30: 1003–1005
   Web of Science ®Google Scholar
• Hohmann J, Gunther G, Vasas A, Kalman A, Argay G. Isolation and structure revision of pepluane diterpenoids from Euphorbia peplus. J Nat Prod 1999a; 62: 107–109
   PubMed Web of Science ®Google Scholar
• Hohmann J, Vasas A, Gunther G, Dombi G, Blazso G, Falkay G, Mathe I, Jerkovich G. Jatrophane diterpenoids from Euphorbia peplus. Phytochemistry 1999b; 51: 673–677
   PubMed Web of Science ®Google Scholar
• Ishihara K, Hamada H, Hirata T, Nakajima N. Biotransformation using plant cultured cells. J Mol Catal B Enzym 2003; 23: 145–170
   Web of Science ®Google Scholar
• Jakupovic J, Jeske F, Morgenstern T, Tsichritzis F, Marco JA, Berendsohn W. Diterpenes from Euphorbia segetalis. Phytochemistry 1998a; 47: 1583–1600
   Web of Science ®Google Scholar
• Jakupovic J, Morgenstern T, Marco JA, Berendsohn W. Diterpenes from Euphorbia paralias. Phytochemistry 1998b; 47: 1611–1619
   Web of Science ®Google Scholar
• Kedei N, Lundberg DJ, Toth A, Welburn P, Garfield SH, Blumberg PM. Characterization of the interaction of ingenol 3-angelate with protein kinase C. Cancer Res 2004; 64: 3243–3255
   PubMed Web of Science ®Google Scholar
• Marco JA, SanzCervera JF, Yuste A. Ingenane and lathyrane diterpenes from the latex of Euphorbia canariensis. Phytochemistry 1997; 45: 563–570
   Web of Science ®Google Scholar
• Mbwambo ZH, Lee SK, Mshiu EN, Pezzuto JM, Kinghorn AD. Constituents from the stem wood of Euphorbia quinquecostata with phorbol dibutyrate receptor-binding inhibitory activity. J Nat Prod 1996; 59: 1051–1055
   PubMed Web of Science ®Google Scholar
• Ogbourne SM, Suhrbier A, Jones B, Cozzi SJ, Boyle GM, Morris M, McAlpine D, Johns J, Scott TM, Sutherland KP, Gardner JM, Le TT, Lenarczyk A, Aylward JH, Parsons PG. Antitumor activity of 3-ingenyl angelate: plasma membrane and mitochondrial disruption and necrotic cell death. Cancer Res 2004; 64: 2833–2839
   PubMed Web of Science ®Google Scholar
• Ogbourne SM, Hampson P, Lord JM, Parsons P, De Witte PA, Suhrbier A. Proceedings of the First International Conference on PEP005. Anticancer Drug 2007; 18: 357–362
   Google Scholar
• Pras N. Bioconversion of naturally-occurring precursors and related synthetic compounds using plant-cell cultures. J Biotechnol 1992; 26: 29–62
   PubMed Web of Science ®Google Scholar
• Rizk AM, Hammouda FM, Elmissiry MM, Radwan HM, Evans FJ. Constitutents Egyptian Euphorbiaceae. 13. Biologically-active diterpene esters from Euphorbia peplus. Phytochemistry 1985; 24: 1605–1606
   Web of Science ®Google Scholar
• Rubinstein LV, Shoemaker RH, Paull KD, Simon RM, Tosini S, Skehan P, Scudiero DA, Monks A, Boyd MR. Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines. J Natl Cancer Inst 1990; 82: 1113–1118
   PubMed Web of Science ®Google Scholar
• Seip EH, Hecker E. Skin irritant ingenol esters from Euphorbia esula. Planta Med 1982; 46: 215–218
   PubMed Web of Science ®Google Scholar
• Sims IM, Middleton K, Lane AG, Cairns AJ, Bacic A. Characterisation of extracellular polysaccharides from suspension cultures of members of the Poaceae. Planta 2000; 210: 261–268
   PubMed Web of Science ®Google Scholar
• Suga T, Hirata T. Biotransformation of exogenous substrates by plant-cell cultures. Phytochemistry 1990; 29: 2393–2406
   Web of Science ®Google Scholar
• Teng RW, McManus D, Mau SL, Bacic A. Biotransformation of podophyllotoxin by Hordeum vulgare cell suspension cultures. Biocatal Biotransform 2007; 25: 1–8
   Web of Science ®Google Scholar
• Weedon D, Chick J. Home treatment of basal-cell carcinoma. Med J Aust 1976; 1: 928–928
   PubMed Web of Science ®Google Scholar