nerolidol

ChEBI · EMBL-EBI ↗ · Källdatum saknas · Källans villkor

A farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent.

ChanWeng-Keong; TanLoh Teng-Hern; ChanKok-Gan; LeeLearn-Han; GohBey-Hing; FortiLuca ↗ · Apr 28, 2016 · Källans villkor

Given the fact that chemical compounds belonging to the sesquiterpene group are well known for their antioxidant properties [113,114], perhaps antioxidant activity may be expected from nerolidol. Furthermore, EOs containing nerolidol derived from medicinal plants were found to exhibit antioxidant activity, suggesting its plausible utilization as an antioxidant agent. Indeed, it has been demonstrated that nerolidol exhibits potent antioxidant properties in counterbalancing the effect of ROS by protecting the cells against oxidative damage to lipids, proteins and DNA [73,74,75]. According to a study conducted by Vinholes et al., the antioxidant activity of cis-nerolidol was evaluated using 1,1-diphenyl-2-picrylhydrazine (DPPH) radical scavenging assay. The study revealed that cis-nerolidol exhibited DPPH scavenging activity [73]. In another study, cis-nerolidol was found to possess higher scavenging activity towards hydroxyl radicals with IC50 measured at 1.48 mM [73]. Due to the ability in scavenging several types of free radicals, cis-nerolidol was evidenced to protect Caco-2 cells against oxidative stress induced by tert-butyl hydroperoxide (tert-BuOOH), suggesting that nerolidol is a good antioxidant that exerts protection against oxidative damage [73]. Another study conducted by Vinholes et al. reported that cis-nerolidol mediated its strong antioxidant activity in protecting the hepatocytes through the inhibition of lipid peroxidation induced by tert-BuOOH, thereby 1mM of cis-nerolidol resulted in 36.50% ± 4.47% of malonaldehyde (MDA) reduction [74].

ChanWeng-Keong; TanLoh Teng-Hern; ChanKok-Gan; LeeLearn-Han; GohBey-Hing; FortiLuca ↗ · Apr 28, 2016 · Källans villkor

Due to nerolidol being used as a potent skin permeation enhancer with low toxicity, a number of studies were conducted on the toxicological properties of nerolidol. Mendanha et al. compared the hemolytic and toxic effects of nerolidol and various monoterpenes on fibroblast cells as well as their effect on erythrocyte membrane fluidity [155]. By using the 3T3 NRU assay to evaluate the cytotoxicity of nerolidol and various monoterpenes (α-terpineol, l-(−)-carvone, (+)-limonene, l-menthone, d,l-menthol, pulegone and 1,8-cineole) on fibroblast cells, nerolidol was found to be the most cytotoxic with its IC50 value of 0.06 ± 0.01 mM. Besides, nerolidol caused 50% hemolysis at 2.3 ± 0.8 mM and induced a significant increase in the fluidity of erythrocyte membrane at 2.5 × 109 molecules/cell, indicating that the nerolidol possessed the highest hemolytic effect on erythrocyte membrane fluidity when compared to terpenes. In addition, electron paramagnetic resonance (EPR) spectroscopy of the spin label 5-doxyl stearic acid (5-DSA) was used to investigate the effect of terpenes on membrane fluidity in erythrocyte and fibroblast cells. Nerolidol was found to be more potent than terpenes that caused an increase in the membrane fluidity. The results implied that nerolidol was able to increase membrane fluidity but also had increased ability to disrupt the membrane and had higher cytotoxic potential.

ChanWeng-Keong; TanLoh Teng-Hern; ChanKok-Gan; LeeLearn-Han; GohBey-Hing; FortiLuca ↗ · Apr 28, 2016 · Källans villkor

Ferreira et al. further examined the toxicity of nerolidol (a racemic mixture of cis- and trans-isomers) (1:1) on mitochondrial and cellular energetics in in vivo model using Wister rat liver mitochondria and in vitro model using HepG2 (human hepatocellular liver carcinoma) cells [12]. In the in vitro study, nerolidol exertes hepatic cell cytotoxicity due to a decrease in ATP/ADP levels by negatively interfering with hepatic mitochondrial bioenergetics in concentrations lower than 2.4 μM. Consequently, nerolidol induced cell arrest and cell death which is possibly due to the inhibition of F0F1-ATP synthase in a concentration-dependent manner. In the in vivo study, nerolidol (low doses up to 2.4 μM) induced a decrease in transmembrane electric potential in the mitochondrial membrane isolated from rat liver in a concentration-dependent manner [12]. By decreasing transmembrane electric potential, nerolidol could negatively affect the hepatic mitochondrial bioenergetics as it would cause mitochondrial dysfunction, thus leading to hepatic cell cytotoxicity and eventually cell death [164].

ChanWeng-Keong; TanLoh Teng-Hern; ChanKok-Gan; LeeLearn-Han; GohBey-Hing; FortiLuca ↗ · Apr 28, 2016 · Källans villkor

Pículo et al. had investigated the genotoxicity and clastogenicity (ability to cause DNA damage by inducing chromosomal aberrations) effects of trans-nerolidol in blood and liver cells of 12-week-old male Swiss albino mice (Mus musculus) using comet and micronucleus assays respectively [169]. The experiment was based on the cytotoxicity effect analysis by scoring 200 consecutive total polychromatic (PCE) and normochromatic (NCE) erythrocytes (PCE:NCE ratio) in bone marrow cells and no significant decrease in PCEs:NCEs ratios at the three doses tested (250, 500 and 2000 mg kg−1) was observed, indicating the absence of cytotoxic effects of trans-nerolidol at these doses. Nevertheless, weak genotoxic effects of trans-nerolidol in the blood and liver cells were observed and a slight increase in the DNA damage at higher doses. Based on the available studies, it can be deduced that the non-toxic dose of trans-nerolidol for animal is up to 2000 mg/kg. Moreover, no DNA damage was observed in the peripheral blood cells and liver of the animals. In order to determine the safety of nerolidol consumption in humans, more clinical trials should be conducted to assess and validate the toxicity and side effects of nerolidol in humans.