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Antiprotozoal Activity and Cytotoxicity of Novel 1,7‐Dioxadispiro[5.1.5.2]pentadeca‐9,12‐dien‐11‐one Derivatives from Amomum aculeatum
Author(s) -
Heilmann Jörg,
Mayr Stefan,
Brun Reto,
Rali Topul,
Sticher Otto
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20001108)83:11<2939::aid-hlca2939>3.0.co;2-n
Subject(s) - chemistry , antiprotozoal , cytotoxicity , trypanosoma cruzi , trypanosoma brucei rhodesiense , ic50 , plasmodium falciparum , stereochemistry , petroleum ether , rhizome , fractionation , cancer cell lines , trypanosoma brucei , in vitro , biochemistry , traditional medicine , chromatography , cancer cell , cancer , parasite hosting , medicine , biology , world wide web , computer science , malaria , immunology , extraction (chemistry) , gene
Cytotoxicity against the KB cancer cell line as a lead bioactivity‐guided fractionation of the petroleum ether extract of rhizomes of Amomum aculeatum Roxb. led to the isolation of three novel dioxadispiro[5.1.5.2]pentadeca‐9,12‐dien‐11‐one derivatives. The structures of aculeatin A ( 1 ), aculeatin B ( 2 ), and aculeatin C ( 3 ) were established as rel ‐(2 R ,4 R ,6 S )‐ and rel ‐(2 R ,4 R ,6 R )‐4‐hydroxy‐2‐tridecyl‐1,7‐dioxadispiro[5.1.5.2]pentadeca‐9,12‐dien‐11‐one ( 1 and 2 , resp.) and rel ‐(2 R ,4 R ,6 R )‐2‐[4‐(3‐dodecyl‐2‐heptyl‐3‐hydroxy‐6‐oxocylohexa‐1,4‐dienyl)‐2‐oxobutyl]‐4‐hydroxy‐1,7‐dioxadispiro[5.1.5.2]pentadeca‐9,12‐dien‐11‐one ( 3 ) by extensive spectroscopic analyses, particularly 13 C‐NMR, inverse‐gated 13 C, HMQC, HMBC, NOESY, and INADEQUATE NMR experiments as well as mass spectrometry. The aculeatins represent a novel type of natural products. All compounds showed high cytotoxicity against the KB cell line: 1 , IC 50 =1.7 μ M ; 2 , IC 50 =2.0 μ M ; 3 , IC 50 =1.6 μ M . Additional 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 ( 1 , IC 50 =0.18 μ M ; 2 , IC 50 =0.43 μ M ; 3 , IC 50 =0.37 μ M ).