Heilmann, Jörg and Mayr, Stefan and Brun, Reto and Rali, Topul and Sticher, Otto (2000) Antiprotozoal activity and cytotoxicity of novel 1,7-dioxadispiro[126.96.36.199]pentadeca-9,12-dien-11-one derivatives from Amomum aculeatum. Helvetica Chimica Acta 83 (11), pp. 2939-2945.
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Cytotoxicity against the KB cancer cell line as a lead bioactivity-guided fractionation of the petroleum ether ext. of rhizomes of Amomum aculeatum RoxB. led to the isolation of three novel dioxadispiro[188.8.131.52]-pentadeca-9,12-dien-11-one derivs. The structures of aculeatin A, aculeatin B, and aculeatin C were established as rel-(2R,4R,6S)- and rel-(2R,4R,6R)-4-hydroxy-2-tridecyl-1,7-dioxadispiro[184.108.40.206]pentadeca-9,12-dien-11-one and rel-(2R,4R,6R)-2-[4-(3-dodecyl-2-heptyl-3-hydroxy-6-oxocyclohexa-1,4-dienyl)-2-oxobutyl]-4-hydroxy-1,7-dioxadispiro[220.127.116.11]pentadeca-9,12-dien-11-one resp. by extensive spectroscopic analyses, particularly 13C-NMR, inverse-gated 13C, HMQC, HMBC, NOESY, and INADEQUATE NMR expts. as well as mass spectrometry. The aculeatins represent a novel type of natural products. All compds. showed high cytotoxicity against the KB cell line: IC50=1.7 micro M; IC50=2.0 micro M; IC50 = 1.6 micro M resp. Addnl. testing against two Plasmodium falciparum strains as well as against trypomastigote forms of Trypanosoma brucei rhodesiense and Trypanosoma cruzi showed strong activities, particularly against P. falciparum strain K1 (IC50=0.18micro M; IC50=0.43micro M; IC50=0.37 micro M).
|Additional information (public):||CAN 134:172732 1-5 Pharmacology 326794-05-2P (Aculeatin A); 326794-06-3P (Aculeatin B); 326794-07-4P (Aculeatin C) Role: BAC (Biological activity or effector, except adverse), BOC (Biological occurrence), BSU (Biological study, unclassified), PRP (Properties), PUR (Purification or recovery), THU (Therapeutic use), BIOL (Biological study), OCCU (Occurrence), PREP (Preparation), USES (Uses) (antiprotozoal activity and cytotoxicity of novel dioxadispiro pentadeca dienone derivs. from Amomum aculeatum)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann)|
|Keywords:||Molecular structure (Aculeatin A (dioxa dispiropentadecadienone) Molecular structure (Aculeatin B (dioxa dispiropentadecadienone) Molecular structure (Aculeatin C (dioxa dispiropentadecadienone) Amomum aculeatum Antitumor agents New natural products Protozoacides (antiprotozoal activity and cytotoxicity of novel dioxadispiro pentadeca dienone derivs. from Amomum aculeatum) antiprotozoal cytotoxicity dioxadispiropentadecadien deriv isolation Amomum structure activity antiprotozoal cytotoxicity aculeatin|
|Subjects:||500 Science > 570 Life sciences|
500 Science > 540 Chemistry & allied sciences
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||No|
|Owner:||Prof. Dr. Joerg Heilmann|
|Deposited On:||15 Oct 2010 10:30|
|Last Modified:||15 Oct 2010 10:30|