New antimalarial and cytotoxic 4-nerolidylcatechol derivatives

Selected Compounds Structurally Related to Acyclic Sesquiterpenoids and Their Antibacterial and Cytotoxic Activity

“…What is more, the maximum metabolic inhibitory effect observed for the highest compound concentration did not exceed 15% (data not shown). Studies performed by Pohlit et al indicated no toxicity of nerolidol against other human melanoma MDA/MB-435 cell lines and colon carcinoma HCT-8 cells [12]. These data suggest that the obtained compounds could probably be safely used in flavour and fragrance compositions.…”

“…Geranyl acetone has also antimicrobial properties as shown by the examination of its food preservative ability [10]. Moreover, natural sesquiterpenoids in vivo and in vitro have chemopreventive and chemotherapeutic properties against human cancer cell lines (inter alia: human malignant melanoma, promyelocytic leukemia and lung cancer) [11][12][13][14].…”

In Vivo Antimalarial Activity and Mechanisms of Action of 4-Nerolidylcatechol Derivatives

“…Natural product 1 makes up 5% or more of the dry weight of the mature roots of P. peltatum and was obtained by extraction of the dry, ground roots with chloroform and ethanol (1:1), evaporation of the solvents, and column chromatography on the resulting extract as previously described (25). The three semisynthetic derivatives 2 to 4 studied herein were synthesized from freshly purified compound 1 in straightforward synthetic procedures that have been published previously (26,29). Briefly, 1,2-O,O-diacetyl-4-nerolidylcatechol (2) was prepared by diacetylation of compound 1 in acetic anhydride/pyridine.…”

“…After each of these reactions, column chromatography and preparative thin-layer chromatography were used for isolation and purification of the products whose structures were determined based on nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) techniques. The purities of the products were evaluated by thin-layer chromatography and liquid chromatography coupled to mass spectrometry, and they were considered to be Ͼ95% (26). The commercial drug standards chloroquine diphosphate (Sigma-Aldrich, Steinheim, Westphalia, Germany) and quinine sulfate (Sigma-Aldrich, Steinheim, Westphalia, Germany) were used as controls in the biological tests.…”

“…Mono-and di-O-alkyl and di-O-acyl derivatives of this compound have been introduced and exhibit improved chemical stability. These derivatives exhibit a range of in vitro inhibitory activities against the K1 strain of Plasmodium falciparum (IC 50 ϭ 0.67 to 23 M) (26,27), antioxidant activity comparable to food preservatives BHA (butylated hydroxyanisole) and BHT (butylated hydroxytoluene), and low toxicity to normal cells (28).…”