Minor cytotoxic and antibacterial compounds from the rhizomes of Amomum aculeatum.
A new cytotoxic 1,7-dioxa-dispiro[5.1.5.2]pentadeca-9,12-dien-11-one derivative, aculeatin D, and a new alkenone, 5-hydroxy-hexacos-1-en-3-one, have been isolated as minor compounds from the rhizomes of Amomum aculeatum. Their structures have been determined mainly by NMR spectroscopy and mass spectrometry. Aculeatin D showed high cytotoxicity against the KB and the L-6 cell line with IC(50) of 0.38 microg/ml and 1 microg/ml, respectively. Additionally, it revealed remarkable activity against two Plasmodium falciparum strains, as well as against Trypanosoma brucei rhodesiense and Trypanosoma cruzi. 5-Hydroxy-hexacos-1-en-3-one exhibited neither cytotoxic nor antiprotozoal activity, whereas antibacterial testing against Bacillus cereus, Escherichia coli and Staphylococcus epidermidis showed moderate to strong activity for both compounds.
Heilmann
J
J
Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH), Zurich, CH-8057 Zurich, Switzerland. heilmann@pharma.ethz.ch
Brun
R
R
Mayr
S
S
Rali
T
T
Sticher
O
O
D000475:Alkenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002460:Cell Line; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D007659:Ketones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D009512:New Guinea; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D051381:Rats; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
C436886:1,7-dioxa-dispiro(5.1.5.2)pentadeca-9,12-dien-11-one; C436885:5-hydroxy-hexacos-1-en-3-one; D000475:Alkenes; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000972:Antineoplastic Agents, Phytogenic; D000981:Antiprotozoal Agents; D007659:Ketones; D013141:Spiro Compounds