Compendio degli studi più significativi con riferimento a proprietà, assunzione, effetti.

Brito RG, Guimarães AG, Quintans JS, Santos MR, De Sousa DP, Badaue-Passos D Jr, de Lucca W Jr, Brito FA, Barreto EO, Oliveira AP, Quintans LJ Jr. Citronellol, a monoterpene alcohol, reduces nociceptive and inflammatory activities in rodents. J Nat Med. 2012 Oct;66(4):637-44. doi: 10.1007/s11418-012-0632-4. 

Abstract. We describe the antinociceptive and anti-inflammatory properties of citronellol (CT) in rodents. CT, a monoterpene alcohol, is a naturally occurring monoterpene compound prevalent in essential oils of various aromatic plant species, such as Cymbopogon citratus. In mice, when evaluated against acetic-acid-induced abdominal writhing, CT (25, 50 and 100 mg/kg, i.p.) reduced (P < 0.001) the amount of writhing compared to the control group. In the formalin test, CT also significantly inhibited both the early (neurogenic pain) and the late (inflammatory pain) phases of formalin-induced licking (P < 0.001). When assessed in a thermal model of pain, CT (100 mg/kg, i.p.) caused a significant increase (P < 0.05) in the latency response on the hot-plate test. Such results were unlikely to be caused by motor abnormality. The anti-inflammatory activity of CT was investigated through carrageenan-induced pleurisy in mice. Pretreatment with CT was able to inhibit both neutrophil infiltration and the increase in TNF-α level in the exudates from carrageenan-induced pleurisy. In in vitro experiments, CT (1 and 100 μg/ml) also decreased nitric oxide production by LPS-stimulated macrophage. Together, these results indicate that CT is effective as an analgesic compound in various pain models, with its action probably mediated by the inhibition of peripheral mediators as well as central inhibitory mechanisms that could be related to its strong antioxidant effect observed in vitro.

Lapczynski A, Letizia CS, Api AM. Fragrance material review on (+)-(R)-citronellol. Food Chem Toxicol. 2008 Nov;46 Suppl 11:S114-6. doi: 10.1016/j.fct.2008.06.018. 

Abstract. A toxicologic and dermatologic review of (+)-(R)-citronellol when used as a fragrance ingredient is presented.

Staudt A, Duarte PF, Amaral BPD, Peixoto Andrade BCO, Simas NK, Correa Ramos Leal I, Sangenito LS, Santos ALSD, de Oliveira D, Junges A, Cansian RL, Paroul N. Biological properties of functional flavoring produced by enzymatic esterification of citronellol and geraniol present in Cymbopogon winterianus essential oil. Nat Prod Res. 2021 Dec;35(24):5981-5987. doi: 10.1080/14786419.2020.1810032.

Abstract. The chemical composition and biological properties of citronella essential oil were modified by enzymatic esterification reaction of the major monoterpenic alcohols with cinnamic acid. The almost complete conversion of geraniol and citronellol present in the citronella (Cymbopogon winterianus) essential oil, into geranyl (99%) and citronellyl (98%) cinnamates was obtained after 48 hours of reaction using a molar ratio of 3:1 (cinnamic acid/alcohol), lipase concentration (Novozym 435) of 15% (w/w) and 70 °C. The esterified oil showed higher antimicrobial activity against Staphylococcus aureus bacteria resistant to oxacillin and penicillin and also greater larvicidal activity against Aedes aegypti larvae compared to unesterified oil. The results concerning the evaluation of toxicity against Artemia salina and cytotoxicity against monkey kidney epithelial cells also showed the superiority of the esterified oil.

Pino-Otín MR, Langa E, Val J, Mainar AM, Ballestero D. Impact of citronellol on river and soil environments using non-target model organisms and natural populations. J Environ Manage. 2021 Jun 1;287:112303. doi: 10.1016/j.jenvman.2021.112303.

Abstract. ...Our results show that citronellol has a negative impact on the environment. Although acute effects cannot be expected, it is necessary to quantify the environmental levels as well as the long-term and persistent effects of this monoterpene. Copyright © 2021 The Author(s). 

Rajendran J, Pachaiappan P, Thangarasu R. Citronellol, an Acyclic Monoterpene Induces Mitochondrial-Mediated Apoptosis through Activation of Proapoptotic Factors in MCF-7 and MDA-MB-231 Human Mammary Tumor Cells. Nutr Cancer. 2021;73(8):1448-1458. doi: 10.1080/01635581.2020.1800766. 

Abstract. The present study investigated the anticancer activity of citronellol (CT) by analyzing the mitochondrial-mediated activation of apoptosis in MCF-7 and MDA-MB-231 human mammary tumor cell lines. Cytotoxicity, cell growth, and apoptosis were determined by measuring reactive oxygen species (ROS), the level of mitochondrial membrane potential (ΔΨm), DNA damage, and changes in morphology and expression of proteins involved in apoptosis in MCF-7 and MDA-MB-231 cells. Our results indicate that CT induces apoptosis as evidenced by the loss of cell viability, increase ROS generation, altered ΔΨm, and enhanced DNA damage. Further, CT inhibits Bcl-2 expression with the up-regulation of Bax, caspase-9, and -7 in both cancer cells. CT induces apoptosis in MCF-7 human mammary tumor cells by inducing oxidative damage and modulating the expression of various pro and anti-apoptotic proteins. Hence, CT might be a potential therapeutic agent for the treatment of breast cancer.

Kayishaer A, Fadlallah S, Mouterde LMM, Peru AAM, Werghi Y, Brunois F, Carboué Q, Lopez M, Allais F. Unprecedented Biodegradable Cellulose-Derived Polyesters with Pendant Citronellol Moieties: From Monomer Synthesis to Enzymatic Degradation. Molecules. 2021 Dec 18;26(24):7672. doi: 10.3390/molecules26247672.

Abstract. Levoglucosenone (LGO) is a cellulose-derived molecule that is present commercially on a multi-ton/year scale. Taking advantage of the α,β-conjugated ketone of LGO, a new citronellol-containing 5-membered lactone (HBO-citro) was synthesized through a one-pot two-step pathway involving oxa-Michael addition and Baeyer-Villiger oxidation. The solvent-free treatment of HBO-citro with NaBH4 at room temperature led to the full reduction of the lactone moiety which gave a novel fully renewable triol monomer having a citronellol side chain (Triol-citro). Noticeably, by simply changing the reducing agent, temperature and reaction duration, the partial reduction of HBO-citro can be achieved to yield a mixture of 5- and 6-membered Lactol-citro molecules. Triol-citro was chosen to prepare functional renewable polyesters having citronellol pendant chains via polycondensation reactions with diacyl chlorides having different chain lengths. Good thermal stability (Td5% up to 170 °C) and low glass transition temperatures (as low as -42 °C) were registered for the polyesters obtained. The polymers were then hydrolyzed using a commercial lipase from Thermomyces lanuginosus (Lipopan® 50 BG) to assess their biodegradability. A higher degradation profile was found for the polyesters prepared using co-monomers (acyl chlorides) having longer chain lengths. This is likely due to the decreased steric hindrance around the ester bonds which allowed enhanced accessibility of the enzyme.

Katsukawa M, Nakata R, Koeji S, Hori K, Takahashi S, Inoue H. Citronellol and geraniol, components of rose oil, activate peroxisome proliferator-activated receptor α and γ and suppress cyclooxygenase-2 expression. Biosci Biotechnol Biochem. 2011;75(5):1010-2. doi: 10.1271/bbb.110039. 

Abstract. We evaluated the effects of rose oil on the peroxisome proliferator-activated receptor (PPAR) and cyclooxygenase-2 (COX-2). Citronellol and geraniol, the major components of rose oil, activated PPARα and γ, and suppressed LPS-induced COX-2 expression in cell culture assays, although the PPARγ-dependent suppression of COX-2 promoter activity was evident only with citronellol, indicating that citronellol and geraniol were the active components of rose oil.