The monoterpenoids citral and geraniol are moderate inhibitors of CYP2B6 hydroxylase activity

Seo, Kyung-Ah; Kim, Hyun-Mi; Ku, Hei-Young; Ahn, Hee-Jeong; Park, Soo‐Jin; Bae, Soo Kyung; Shin, Jae‐Gook; Liu, Kwang-Hyeon

doi:10.1016/j.cbi.2008.06.003

Cited by 34 publications

(35 citation statements)

References 22 publications

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“…Further experimental evidence lent supported that citral has an ability to suppress oxidative stress, possibly through the induction of endogenous antioxidant proteins, such as phase II xenobiotic metabolizing enzymes, as well as glutatione S-transferase (Nakamura et al , 2003). In addition, it has been recently demonstrated that citral strongly inhibited the CYP2B60 hydroxylase activity (Seo et al , 2008) involved, not only in xenobiotic activation of a wide variety of pro-mutagens, but also in the synthesis of Aflatoxin B 1 mycotoxin (Shukla et al , 2009), involved in gastric carcinogenesis. The present work provides new insights into citral and carvone chemoprevention.…”

Section: Discussionmentioning

confidence: 99%

“…Although the chemopreventive properties of L. alba terpenoids, such as carvone, geraniol, limonene, and perillyl alcohol have been well-documented (He et al , 1997; Crowell, 1999; Uedo et al , 1999; de Carvalho and da Fonseca, 2006; Paduch et al , 2007; Patil et al , 2009; Rabi and Bishayee, 2009), little is known about the chemopreventive potential of other L. alba EO constituents, for example, citral (Connor, 1991; Nakamura et al , 2003; Seo et al , 2008). …”

Section: Introductionmentioning

confidence: 99%

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Chemical composition and antigenotoxic properties of Lippia alba essential oils

2011

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The present work evaluated the chemical composition and the DNA protective effect of the essential oils (EOs) from Lippia alba against bleomycin-induced genotoxicity. EO constituents were determined by Gas Chromatography/Mass Spectrometric (GC-MS) analysis. The major compounds encountered being citral (33% geranial and 25% neral), geraniol (7%) and trans-β-caryophyllene (7%) for L. alba specimen COL512077, and carvone (38%), limonene (33%) and bicyclosesquiphellandrene (8%) for the other, COL512078. The genotoxicity and antigenotoxicity of EO and the compounds citral, carvone and limonene, were assayed using the SOS Chromotest in Escherichia coli. The EOs were not genotoxic in the SOS chromotest, but one of the major compound (limonene) showed genotoxicity at doses between 97 and 1549 mM. Both EOs protected bacterial cells against bleomycin-induced genotoxicity. Antigenotoxicity in the two L. alba chemotypes was related to the major compounds, citral and carvone, respectively. The results were discussed in relation to the chemopreventive potential of L. alba EOs and its major compounds.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemical composition and antigenotoxic properties of Lippia alba essential oils

2011

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“…However, high levels of α-tocopherol acetate in the H 2 O 2 group as well as geraniol + H 2 O 2 group also indicate that, apart from its antioxidants role, geraniol can interact with cytochrome p450 enzymes. It is known that there is a relationship between cytochrome p450 activity and geraniol metabolism in the cells (34,35). In a recent study reported that geraniol treatment in rats with non-alcoholic steatohepatitis models reduce oxidative stress and regulate cytochrome p450 activity (36).…”

Section: Discussionmentioning

confidence: 99%

Effect of Geraniol on Brain Cholesterol, Vitamin A and E Levels in The Hydrogen Peroxide-Treated Rats

Şahin

2018

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ÖzetAmaç: Bir monoterpen olan geraniol, bazı bitkilerde yer alan doğal bir antioksidandır. Hidrojen peroksit (H 2 O 2 ) ise reaktif oksijen türlerinin (ROS) bir üyesidir. Bu çalışmada, H 2 O 2 uygulanan sıçanlarda geraniolün beyin kolesterolü ve yağda çözünen A (retinol) ve E (alfa (α)-tokoferol ve α-tokoferol asetat) vitaminlerine etkisinin belirlenmesi amaçlanmıştır. Gereçler ve Yöntem: Çalışmada yetişkin erkek Wistar sıçanlar rastgele dört gruba ayrılarak (n=7), geraniol (50mg/kg) ve H 2 O 2 (16mg/kg), intraperitoneal olarak, 30 gün süresince gün aşırı uygulandı. Beyin numuneleri homojenize edildikten sonra kolesterol, α-tokoferol, α-tokoferol asetat ve retinol düzeyleri yağ ekstraktlarından HPLC ile analiz edildi. Bulgular: Beyin kolesterol düzeyinin H 2 O 2 grubunda kontrol grubuna kıyasla daha fazla olduğu belirlendi. H 2 O 2 ve geraniol+ H 2 O 2 gruplarında, beyin α-tokoferol asetat düzeylerinin kontrole kıyasla daha yüksek olduğu bulundu. Beyin retinol seviyesi bakımından grupların hiçbirisinde istatistiksel olarak anlamlı bir değişiklik mevcut değildi. Sonuç: Elde ettiğimiz veriler, beyinde kolesterol ve α-tokoferol asetat düzeylerinin H 2 O 2 ile oluşturulan oksidatif stresten etkilendiğini göstermektedir. Geraniolün erkek sıçanlarda H 2 O 2 'nin etkilerini azaltma potansiyeli olduğu söylenebilir.Anahtar kelimeler: Geraniol, hidrojen peroksit, beyin, kolesterol, α-tokoferol Aim: Geraniol, a monoterpene, is a plant-derived natural antioxidant. Hydrogen peroxide (H 2 O 2 ) is a member of reactive oxygen species (ROS). The objective of this study is to de-termine the effect of geraniol on brain cholesterol and lipophilic vitamins such as vitamin A (retinol) and vitamin E (alpha (α)-tocopherol and α-tocopherol acetate) in H 2 O 2 -administrated male rats. Materials and Methods: Adult male Wistar rats were randomly divided into four groups (n=7). Geraniol (50 mg/kg) and H 2 O 2 (16 mg/kg) were administered by an intraperitoneal injection for 30 days with a 1-day interval. Brain samples were homogenized and cholesterol, α-tocopherol, α-tocopherol acetate, and retinol levels analyzed from lipid extracts by HPLC. Results: Brain cholesterol level was found to be significantly higher in the H 2 O 2 group than the control group. Brain α-tocopherol acetate levels were found to be significantly higher in the H 2 O 2 and the geraniol+H 2 O 2 groups than the control group. There was no difference in retinol levels between any groups. Conclusion: In conclusion, our results indicate that brain cholesterol and α-tocopherol acetate levels are affected by H 2 O 2 -induced oxidative stress. Moreover, we suggest that geraniol has the potential to reduce the effect of H 2 O 2 in male rats. Keywords

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“…The major network affected involved 7 known molecules for cancer and its biological functions, and two P450 enzymes (CYP3A4 and CYP2B6, Figure 2). Menthol was reported to be an inhibitor of CYP3A4 (62) and CYP2B6 (63), and both were associated with altering the nicotine CYP2A6 metabolism (64). Nicotine metabolism is impaired among menthol smokers (15), and detoxification of the potent lung carcinogen NNAL was found lower in menthol smokers (16).…”

Section: Discussionmentioning

confidence: 99%

Menthol Smokers: Metabolomic Profiling and Smoking Behavior

Hsu

Lan

Brasky

et al. 2017

Cancer Epidemiology, Biomarkers &Amp; Prevention

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Background The use of menthol in cigarettes and marketing is under consideration for regulation by the FDA. However, the effects of menthol on smoking behavior and carcinogen exposure have been inconclusive. We previously reported metabolomic profiling for cigarette smokers, and novelly identified a menthol-glucuronide (MG) as the most significant metabolite directly related to smoking. Here, MG is studied in relation to smoking behavior and metabolomic profiles. Methods A cross-sectional study of 105 smokers who smoked two cigarettes in the laboratory one hour apart. Blood nicotine, MG and exhaled carbon monoxide (CO) boosts were determined (the difference before and after smoking). Spearman's correlation, Chi-Square and ANCOVA adjusted for gender, race and cotinine levels for menthol smokers assessed the relationship of MG boost, smoking behavior, and metabolic profiles. Multivariate metabolite characterization using supervised Partial Least Squares-Discriminant Analysis (PLS-DA) was carried out for the classification of metabolomics profiles. Results MG boost was positively correlated with CO boost, nicotine boost, average puff volume, puff duration, and total smoke exposure. Classification using PLS-DA, MG was the top metabolite discriminating metabolome of menthol vs. non-menthol smokers. Among menthol smokers, forty-two metabolites were significantly correlated with MG boost, which linked to cellular functions such as of cell death, survival, and movement. Conclusion Plasma MG boost is a new smoking behavior biomarker that may provides novel information over self-reported use of menthol cigarettes by integrating different smoking measures for understanding smoking behavior and harm of menthol cigarettes. Impacts These results provide insight into the biological effect of menthol smoking.

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The monoterpenoids citral and geraniol are moderate inhibitors of CYP2B6 hydroxylase activity

Cited by 34 publications

References 22 publications

Chemical composition and antigenotoxic properties of Lippia alba essential oils

Chemical composition and antigenotoxic properties of Lippia alba essential oils

Effect of Geraniol on Brain Cholesterol, Vitamin A and E Levels in The Hydrogen Peroxide-Treated Rats

Menthol Smokers: Metabolomic Profiling and Smoking Behavior

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