Citronellol (BioDeep_00000397389)

Main id: BioDeep_00000000679

 

PANOMIX_OTCML-2023


代谢物信息卡片


(+/-)-beta-Citronellol, primary pharmaceutical reference standard

化学式: C10H20O (156.1514)
中文名称: 香茅醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=CCC[C@@H](C)CCO)C
InChI: InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3

描述信息

Citronellol is a monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7. It has a role as a plant metabolite.
Citronellol is a natural product found in Xylopia aromatica, Eupatorium cannabinum, and other organisms with data available.
3,7-Dimethyl-6-octen-1-ol is a metabolite found in or produced by Saccharomyces cerevisiae.
See also: Java citronella oil (part of).
A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.
Citronellol ((±)-Citronellol) is a monoterpene Pelargonium graveolens. Citronellol ((±)-Citronellol) induces necroptosis of cancer cell via up-regulating TNF-α, RIP1/RIP3 activities, down-regulating caspase-3/caspase-8 activities and increasing ROS (reactive oxygen species) accumulation[1].
Citronellol ((±)-Citronellol) is a monoterpene Pelargonium graveolens. Citronellol ((±)-Citronellol) induces necroptosis of cancer cell via up-regulating TNF-α, RIP1/RIP3 activities, down-regulating caspase-3/caspase-8 activities and increasing ROS (reactive oxygen species) accumulation[1].

同义名列表

62 个代谢物同义名

(+/-)-beta-Citronellol, primary pharmaceutical reference standard; 4-01-00-02188 (Beilstein Handbook Reference); ( inverted exclamation markA)-b-Citronellol; (+/-)-beta-Citronellol, analytical standard; (+/-)-beta-Citronellol analytical standard; (+/-)-Citronellol;(+/-)-beta-Citronellol; D-Citronellol;(R)-(+)-beta-Citronellol; 6-Octen-1-ol, 3,7-dimethyl-, (+/-)-; (+/-)-3,7-dimethyl-6-octen-1-ol; (+/-)-3,7-dimethyloct-6-en-1-ol; citronellol, titanium (+4) salt; ()-Citronellol;()--Citronellol; Citronellol, >=95\\%, FCC, FG; 6-Octen-1-ol, 3,7-dimethyl-; (R)-(+)-.beta.-Citronellol; .BETA.-CITRONELLOL, (+/-)-; 3,7-dimethyl-oct-6-en-1-ol; 3,7-Dimethyloct-6-en-1-ol; 3,7-dimethyl-oct-6-en1-ol; 2,6-Dimethyl-2-octen-8-ol; 3,7-DIMETHYL-6-OCTEN-1-OL; 6-Octen-1-ol,7-dimethyl-; beta-CITRONELLOL, (+/-)-; (+/-)-.BETA.-CITRONELLOL; citronellol, (+-)-isomer; citronellol, (R)-isomer; .BETA.-CITRONELLOL [MI]; citronellol, (S)-isomer; (+-)-beta;-Citronellol; (+/-)-beta-Citronellol; beta-Citronellol, 95\\%; (S)-(-)-|A-Citronellol; (+-)-beta-citronellol; Citronellol (natural); pelargonium geraniums; acyclic monoterpenoid; Citronellol Natural; CITRONELLOL, (+/-)-; 2,3-Dihydrogeraniol; .beta.-Citronellol; Citronellol, dl-; Levo-citronellol; (+-)-CITRONELLOL; WLN: Q2Y1&3UY1&1; beta-citronellol; Insect Repellent; Dihydrogeraniol; mite attractant; DL-Citronellol; Tox21_202119; Tox21_300003; citronellol; AI3-25080; Cephrol; Rodinol; C10H20O; nardus; Elenol; (±)-Citronellol; (±)-β-Citronellol; beta-Citronellol; Citronellol



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

135 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 7 BCL2, CASP3, CAT, FDPS, HPGDS, PTGS2, SNCA
Peripheral membrane protein 4 ACHE, CYP1B1, GORASP1, PTGS2
Endoplasmic reticulum membrane 3 BCL2, CYP1B1, PTGS2
Nucleus 7 ACHE, ATF1, BCL2, CASP3, GABPA, PPARA, SNCA
cytosol 7 BCL2, CASP3, CAT, FDPS, HPGDS, LIPE, SNCA
nucleoplasm 6 ATF1, CASP3, FDPS, GABPA, HPGDS, PPARA
RNA polymerase II transcription regulator complex 1 ATF1
Cell membrane 4 ACHE, LIPE, TNF, TRPA1
Cytoplasmic side 1 GORASP1
Cell projection, axon 1 SNCA
Multi-pass membrane protein 1 TRPA1
Golgi apparatus membrane 1 GORASP1
Synapse 2 ACHE, SNCA
cell cortex 1 SNCA
cell surface 2 ACHE, TNF
glutamatergic synapse 1 CASP3
Golgi apparatus 3 ACHE, ATRN, GORASP1
Golgi membrane 1 GORASP1
growth cone 1 SNCA
neuromuscular junction 1 ACHE
neuronal cell body 3 CASP3, SNCA, TNF
postsynapse 1 SNCA
Cytoplasm, cytosol 1 LIPE
Lysosome 1 SNCA
plasma membrane 5 ACHE, ATRN, SNCA, TNF, TRPA1
synaptic vesicle membrane 1 SNCA
Membrane 8 ACHE, BCL2, CAT, CYP1B1, FDPS, LIPE, SNCA, TRPA1
axon 1 SNCA
caveola 2 LIPE, PTGS2
extracellular exosome 2 ATRN, CAT
endoplasmic reticulum 2 BCL2, PTGS2
extracellular space 7 ACHE, ATRN, IL10, IL4, IL6, SNCA, TNF
perinuclear region of cytoplasm 2 ACHE, SNCA
mitochondrion 4 BCL2, CAT, CYP1B1, SNCA
protein-containing complex 4 BCL2, CAT, PTGS2, SNCA
intracellular membrane-bounded organelle 3 CAT, CYP1B1, HPGDS
Microsome membrane 2 CYP1B1, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 ATRN
Secreted 5 ACHE, IL10, IL4, IL6, SNCA
extracellular region 7 ACHE, CAT, IL10, IL4, IL6, SNCA, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
[Isoform 2]: Secreted 1 ATRN
mitochondrial matrix 2 CAT, FDPS
Extracellular side 1 ACHE
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
actin cytoskeleton 1 SNCA
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 CAT
cis-Golgi network 1 GORASP1
Peroxisome 2 CAT, FDPS
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
chromatin 3 ATF1, GABPA, PPARA
stereocilium bundle 1 TRPA1
phagocytic cup 1 TNF
supramolecular fiber 1 SNCA
Lipid-anchor, GPI-anchor 1 ACHE
[Isoform 3]: Secreted 1 ATRN
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
side of membrane 1 ACHE
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 2 IL6, PTGS2
axon terminus 1 SNCA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
synaptic cleft 1 ACHE
death-inducing signaling complex 1 CASP3
[Isoform 1]: Cell membrane 1 ATRN
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
inclusion body 1 SNCA
interleukin-6 receptor complex 1 IL6
BAD-BCL-2 complex 1 BCL2
ATF4-CREB1 transcription factor complex 1 ATF1
ATF1-ATF4 transcription factor complex 1 ATF1
[Isoform H]: Cell membrane 1 ACHE
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Stoja Milovanovic, Darka Markovic, Ivona Jankovic-Castvan, Ivana Lukic. Cornstarch aerogels with thymol, citronellol, carvacrol, and eugenol prepared by supercritical CO2- assisted techniques for potential biomedical applications. Carbohydrate polymers. 2024 May; 331(?):121874. doi: 10.1016/j.carbpol.2024.121874. [PMID: 38388060]
  • Yimeng Li, Runyang Sun, Yajing Kong, Xiaolin Cai, Tongyu Jiang, Shuai Cheng, Hui Yang, Luyi Song, Xin Lü, Xin Wang, Chao Shi. Antibacterial effect of ultrasound and β-citronellol against Listeria monocytogenes and its application in carrot preservation. Ultrasonics sonochemistry. 2024 Jan; 102(?):106752. doi: 10.1016/j.ultsonch.2023.106752. [PMID: 38211495]
  • Maryam Jadidi, Hasan Mumivand, Abdollah Ehtesham Nia, Alireza Shayganfar, Filippo Maggi. UV-A and UV-B combined with photosynthetically active radiation change plant growth, antioxidant capacity and essential oil composition of Pelargonium graveolens. BMC plant biology. 2023 Nov; 23(1):555. doi: 10.1186/s12870-023-04556-6. [PMID: 37946108]
  • Laure Martinelli, Camille Bihanic, Aurélie Bony, Florence Gros, Corentin Conart, Sébastien Fiorucci, Hervé Casabianca, Frédéric Schiets, Giorgiana Chietera, Benoît Boachon, Bernard Blerot, Sylvie Baudino, Frédéric Jullien, Denis Saint-Marcoux. Citronellol biosynthesis in pelargonium is a multi-step pathway involving PRISE enzymes. Plant physiology. 2023 Oct; ?(?):. doi: 10.1093/plphys/kiad550. [PMID: 37831417]
  • Praveen Thangaraj, Krishnamoorthy Akkanna Subbiah, Nakkeeran Sevugapperumal, Sivakumar Uthandi, Amirtham Damodarasamy, Haripriya Shanmugam. Activity of volatiles induced by microbes and natural plants stifled the growth of Pythium aphanidermatum - the damping off in Tomato. BMC plant biology. 2023 Aug; 23(1):384. doi: 10.1186/s12870-023-04351-3. [PMID: 37563742]
  • Taotao Li, Wenfei Wang, Qiuting Guo, Jia Li, Tiantian Tang, Yujiao Wang, Ding Liu, Kai Yang, Jiayi Li, Kaixue Deng, Fang Wang, Huiting Li, Zhenfeng Wu, Jianbo Guo, Dongyan Guo, Yajun Shi, Junbo Zou, Jing Sun, Xiaofei Zhang, Ming Yang. Rosemary (Rosmarinus officinalis L.) hydrosol based on serotonergic synapse for insomnia. Journal of ethnopharmacology. 2023 Jul; ?(?):116984. doi: 10.1016/j.jep.2023.116984. [PMID: 37532071]
  • Yasameen Shakir Mahmood, Sarmed Hashim Kathem. Protective effect of citronellol in rhabdomyolysis-induced acute kidney injury in mice. Journal of medicine and life. 2023 Jul; 16(7):1057-1061. doi: 10.25122/jml-2023-0102. [PMID: 37900084]
  • Ajay Kumar, Rahul Dev Gautam, Satbeer Singh, Ramesh Chauhan, Manish Kumar, Dinesh Kumar, Ashok Kumar, Sanatsujat Singh. Phenotyping floral traits and essential oil profiling revealed considerable variations in clonal selections of damask rose (Rosa damascena Mill.). Scientific reports. 2023 May; 13(1):8101. doi: 10.1038/s41598-023-34972-5. [PMID: 37208367]
  • Xiao Liu, Chunji Zhu, Yong Yin. Anti-ischemic effect of monoterpene citronellol on experimental stroke models mediated by proinflammatroy cytokines. Combinatorial chemistry & high throughput screening. 2022 Nov; ?(?):. doi: 10.2174/1386207326666221110092715. [PMID: 36372917]
  • Valtcho D Zheljazkov, Giuseppe Micalizzi, Solomon Yilma, Charles L Cantrell, Amber Reichley, Luigi Mondello, Ivanka Semerdjieva, Tzenka Radoukova. Melissa officinalis L. as a Sprout Suppressor in Solanum tuberosum L. and an Alternative to Synthetic Pesticides. Journal of agricultural and food chemistry. 2022 Nov; 70(44):14205-14219. doi: 10.1021/acs.jafc.2c05942. [PMID: 36306427]
  • Amanda Staudt, Patrícia Fonseca Duarte, Bruna Paes do Amaral, Bárbara Carolina de Oliveira Peixoto Andrade, Naomi Kato Simas, Ivana Correa Ramos Leal, Leandro Stefano Sangenito, André Luis Souza Dos Santos, Débora de Oliveira, Alexander Junges, Rogério Luis Cansian, Natalia Paroul. Biological properties of functional flavoring produced by enzymatic esterification of citronellol and geraniol present in Cymbopogon winterianus essential oil. Natural product research. 2021 Dec; 35(24):5981-5987. doi: 10.1080/14786419.2020.1810032. [PMID: 32840398]
  • Zhenghui Jiang, Chen Xu, Limin Wang, Kai Hong, Changwei Ma, Chenyan Lv. Potential enzymes involved in beer monoterpenoids transformation: structures, functions and challenges. Critical reviews in food science and nutrition. 2021 Aug; ?(?):1-11. doi: 10.1080/10408398.2021.1970510. [PMID: 34459289]
  • Matthew E Bergman, Mridula Bhardwaj, Michael A Phillips. Cytosolic geraniol and citronellol biosynthesis require a Nudix hydrolase in rose-scented geranium (Pelargonium graveolens). The Plant journal : for cell and molecular biology. 2021 07; 107(2):493-510. doi: 10.1111/tpj.15304. [PMID: 33949016]
  • María Rosa Pino-Otín, Elisa Langa, Jonatan Val, Ana M Mainar, Diego Ballestero. Impact of citronellol on river and soil environments using non-target model organisms and natural populations. Journal of environmental management. 2021 Jun; 287(?):112303. doi: 10.1016/j.jenvman.2021.112303. [PMID: 33714735]
  • Guodong Zheng, Yingxin Chao, Mengshi Liu, Yuhua Yang, Dedong Zhang, Kanghui Wang, Yiwen Tao, Jianye Zhang, Yongmei Li, Minyan Wei. Evaluation of dynamic changes in the bioactive components in Citri Reticulatae Pericarpium (Citrus reticulata 'Chachi') under different harvesting and drying conditions. Journal of the science of food and agriculture. 2021 Jun; 101(8):3280-3289. doi: 10.1002/jsfa.10957. [PMID: 33222189]
  • Edenilson Dos Santos Niculau, Péricles Barreto Alves, Paulo Cesar de Lima Nogueira, Luciane Pimenta Cruz Romão, Graziele da Costa Cunha, Arie Fitzgerald Blank, Anderson de Carvalho Silva. Chemical Profile and Use of the Peat as an Adsorbent for Extraction of Volatile Compounds from Leaves of Geranium (Pelargonium graveolens L' Herit). Molecules (Basel, Switzerland). 2020 Oct; 25(21):. doi: 10.3390/molecules25214923. [PMID: 33114417]
  • Lina Hagvall, Katarzyna Prystupa-Chalkidis. Contact allergy to oxidized terpenes and occupational contact dermatitis in massage therapists - A case series. Contact dermatitis. 2020 Jun; 82(6):390-392. doi: 10.1111/cod.13494. [PMID: 32060913]
  • Laura Giamperi, Anahi Elena Ada Bucchini, Donata Ricci, Bruno Tirillini, Marcello Nicoletti, Rianasoambolanoro Rakotosaona, Filippo Maggi. Vepris macrophylla (Baker) I. Verd Essential Oil: An Antifungal Agent against Phytopathogenic Fungi. International journal of molecular sciences. 2020 Apr; 21(8):. doi: 10.3390/ijms21082776. [PMID: 32316699]
  • Yamini Sharma, Sumit Kumar Rastogi, Ahmad Perwez, Moshahid Alam Rizvi, Nikhat Manzoor. β-citronellol alters cell surface properties of Candida albicans to influence pathogenicity related traits. Medical mycology. 2020 Jan; 58(1):93-106. doi: 10.1093/mmy/myz009. [PMID: 30843057]
  • Abeer A Mohamed, Said I Behiry, Hosny A Younes, Nader A Ashmawy, Mohamed Z M Salem, Ofelia Márquez-Molina, Alberto Barbabosa-Pilego. Antibacterial activity of three essential oils and some monoterpenes against Ralstonia solanacearum phylotype II isolated from potato. Microbial pathogenesis. 2019 Oct; 135(?):103604. doi: 10.1016/j.micpath.2019.103604. [PMID: 31247257]
  • Jayaganesh Rajendran, Pugalendhi Pachaiappan, Suganthi Subramaniyan. Dose-dependent chemopreventive effects of citronellol in DMBA-induced breast cancer among rats. Drug development research. 2019 09; 80(6):867-876. doi: 10.1002/ddr.21570. [PMID: 31313341]
  • Laurence Lins, Simon Dal Maso, Berenice Foncoux, Anouar Kamili, Yoann Laurin, Manon Genva, M Haissam Jijakli, Caroline De Clerck, Marie Laure Fauconnier, Magali Deleu. Insights into the Relationships Between Herbicide Activities, Molecular Structure and Membrane Interaction of Cinnamon and Citronella Essential Oils Components. International journal of molecular sciences. 2019 Aug; 20(16):. doi: 10.3390/ijms20164007. [PMID: 31426453]
  • Yuan Yuan, Ye Sun, Yanchun Zhao, Chungui Liu, Xiulan Chen, Fengtong Li, Jianzhong Bao. Identification of Floral Scent Profiles in Bearded Irises. Molecules (Basel, Switzerland). 2019 May; 24(9):. doi: 10.3390/molecules24091773. [PMID: 31067789]
  • Lijun Zhou, Zhilin Zhang, Mi Wei, Yongjian Xie, Shan He, Hongan Shi, Zhufeng Lin. Evaluation of the antifungal activity of individual and combined monoterpenes against Rhizopus stolonifer and Absidia coerulea. Environmental science and pollution research international. 2019 Mar; 26(8):7804-7809. doi: 10.1007/s11356-019-04278-z. [PMID: 30675711]
  • Mohaddeseh Abouhosseini Tabari, Mohammad Reza Youssefi, Mojtaba Nasiri, Mojtaba Hamidi, Komeil Kiani, Shohre Alian Samakkhah, Filippo Maggi. Towards green drugs against cestodes: Effectiveness of Pelargonium roseum and Ferula gummosa essential oils and their main component on Echinococcus granulosus protoscoleces. Veterinary parasitology. 2019 Feb; 266(?):84-87. doi: 10.1016/j.vetpar.2018.12.019. [PMID: 30736953]
  • Priscila L Santos, João Pedro S C F Matos, Laurent Picot, Jackson R G S Almeida, Jullyana S S Quintans, Lucindo J Quintans-Júnior. Citronellol, a monoterpene alcohol with promising pharmacological activities - A systematic review. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 Jan; 123(?):459-469. doi: 10.1016/j.fct.2018.11.030. [PMID: 30453001]
  • Gaoming Lei, Jie Li, Tao Zheng, Junqiao Yao, Jingjing Chen, Lengxin Duan. Comparative Chemical Profiles of Essential Oils and Hydrolate Extracts from Fresh Flowers of Eight Paeonia suffruticosa Andr. Cultivars from Central China. Molecules (Basel, Switzerland). 2018 Dec; 23(12):. doi: 10.3390/molecules23123268. [PMID: 30544771]
  • Bing Mu, Yin Zhu, Hai-Peng Lv, Han Yan, Qun-Hua Peng, Zhi Lin. The enantiomeric distributions of volatile constituents in different tea cultivars. Food chemistry. 2018 Nov; 265(?):329-336. doi: 10.1016/j.foodchem.2018.05.094. [PMID: 29884390]
  • Raiane S Lemes, Cassia C F Alves, Elisângela B B Estevam, Mariana B Santiago, Carlos H G Martins, Tainá C L Dos Santos, Antônio E M Crotti, Mayker L D Miranda. Chemical composition and antibacterial activity of essential oils from Citrus aurantifolia leaves and fruit peel against oral pathogenic bacteria. Anais da Academia Brasileira de Ciencias. 2018 Apr; 90(2):1285-1292. doi: 10.1590/0001-3765201820170847. [PMID: 29898096]
  • Mei-Lin Tsai, Cai-Di Lin, Keh Ai Khoo, Mei-Ying Wang, Tsang-Kuei Kuan, Wei-Chao Lin, Ya-Nan Zhang, Ya-Ying Wang. Composition and Bioactivity of Essential Oil from Citrus grandis (L.) Osbeck 'Mato Peiyu' Leaf. Molecules (Basel, Switzerland). 2017 Dec; 22(12):. doi: 10.3390/molecules22122154. [PMID: 29206180]
  • Mohaddeseh Abouhosseini Tabari, Mohammad Reza Youssefi, Aryan Esfandiari, Giovanni Benelli. Toxicity of β-citronellol, geraniol and linalool from Pelargonium roseum essential oil against the West Nile and filariasis vector Culex pipiens (Diptera: Culicidae). Research in veterinary science. 2017 Oct; 114(?):36-40. doi: 10.1016/j.rvsc.2017.03.001. [PMID: 28297637]
  • Miyeon Jang, Junheon Kim, Kyungjae Andrew Yoon, Si Hyeock Lee, Chung Gyoo Park. Biological activity of Myrtaceae plant essential oils and their major components against Drosophila suzukii (Diptera: Drosophilidae). Pest management science. 2017 Feb; 73(2):404-409. doi: 10.1002/ps.4430. [PMID: 27607409]
  • Miu Iijima, Hiromichi Kenmoku, Hironobu Takahashi, Jung-Bum Lee, Masao Toyota, Yoshinori Asakawa, Fumiya Kurosaki, Futoshi Taura. Characterization of 12-Oxophytodienoic Acid Reductases from Rose-scented Geranium (Pelargonium graveolens). Natural product communications. 2016 Dec; 11(12):1775-1782. doi: ". [PMID: 30508331]
  • Leopoldina de Fátima Dantas de Almeida, Jacqueline Felipe de Paula, Rossana Vanessa Dantas de Almeida, David Wynne Williams, Josimeri Hebling, Yuri Wanderley Cavalcanti. Efficacy of citronella and cinnamon essential oils on Candida albicans biofilms. Acta odontologica Scandinavica. 2016 Jul; 74(5):393-8. doi: 10.3109/00016357.2016.1166261. [PMID: 27098375]
  • Yuko Kobayashi, Harumi Sato, Mika Yorita, Hiroto Nakayama, Hironari Miyazato, Keiichiro Sugimoto, Tomoko Jippo. Inhibitory effects of geranium essential oil and its major component, citronellol, on degranulation and cytokine production by mast cells. Bioscience, biotechnology, and biochemistry. 2016 Jun; 80(6):1172-8. doi: 10.1080/09168451.2016.1148573. [PMID: 26927807]
  • Alex Campbell, Philippe Bauchart, Nicholas D Gold, Yun Zhu, Vincenzo De Luca, Vincent J J Martin. Engineering of a Nepetalactol-Producing Platform Strain of Saccharomyces cerevisiae for the Production of Plant Seco-Iridoids. ACS synthetic biology. 2016 05; 5(5):405-14. doi: 10.1021/acssynbio.5b00289. [PMID: 26981892]
  • Subramani Srinivasan, Udaiyar Muruganathan. Antidiabetic efficacy of citronellol, a citrus monoterpene by ameliorating the hepatic key enzymes of carbohydrate metabolism in streptozotocin-induced diabetic rats. Chemico-biological interactions. 2016 Apr; 250(?):38-46. doi: 10.1016/j.cbi.2016.02.020. [PMID: 26944432]
  • T B Vasconcelos, H V Ribeiro-Filho, L T Lucetti, P J C Magalhães. β-Citronellol, an alcoholic monoterpene with inhibitory properties on the contractility of rat trachea. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2016 Feb; 49(2):e4800. doi: 10.1590/1414-431x20154800. [PMID: 26648088]
  • Song Cao, Yang Liu, Mengbo Guo, Guirong Wang. A Conserved Odorant Receptor Tuned to Floral Volatiles in Three Heliothinae Species. PloS one. 2016; 11(5):e0155029. doi: 10.1371/journal.pone.0155029. [PMID: 27163122]
  • H Tolba, H Moghrani, A Benelmouffok, D Kellou, R Maachi. Essential oil of Algerian Eucalyptus citriodora: Chemical composition, antifungal activity. Journal de mycologie medicale. 2015 Dec; 25(4):e128-33. doi: 10.1016/j.mycmed.2015.10.009. [PMID: 26597375]
  • D Zamora, S A Klotz, E A Meister, J O Schmidt. Repellency of the Components of the Essential Oil, Citronella, to Triatoma rubida, Triatoma protracta, and Triatoma recurva (Hemiptera: Reduviidae: Triatominae). Journal of medical entomology. 2015 Jul; 52(4):719-21. doi: 10.1093/jme/tjv039. [PMID: 26335480]
  • Irmanida Batubara, Irma H Suparto, Siti Sa'diah, Ryunosuke Matsuoka, Tohru Mitsunaga. Effects of inhaled citronella oil and related compounds on rat body weight and brown adipose tissue sympathetic nerve. Nutrients. 2015 Mar; 7(3):1859-70. doi: 10.3390/nu7031859. [PMID: 25774603]
  • Martin F Strube-Bloss, Austin Brown, Johannes Spaethe, Thomas Schmitt, Wolfgang Rössler. Extracting the Behaviorally Relevant Stimulus: Unique Neural Representation of Farnesol, a Component of the Recruitment Pheromone of Bombus terrestris. PloS one. 2015; 10(9):e0137413. doi: 10.1371/journal.pone.0137413. [PMID: 26340263]
  • Pankaj Sharma, G C Shah. Composition and antioxidant activity of Senecio nudicaulis Wall. ex DC. (Asteraceae): a medicinal plant growing wild in Himachal Pradesh, India. Natural product research. 2015; 29(9):883-6. doi: 10.1080/14786419.2014.990904. [PMID: 25515495]
  • J C Ribeiro, W L C Ribeiro, A L F Camurça-Vasconcelos, I T F Macedo, J M L Santos, H C B Paula, J V Araújo Filho, R D Magalhães, C M L Bevilaqua. Efficacy of free and nanoencapsulated Eucalyptus citriodora essential oils on sheep gastrointestinal nematodes and toxicity for mice. Veterinary parasitology. 2014 Aug; 204(3-4):243-8. doi: 10.1016/j.vetpar.2014.05.026. [PMID: 24929446]
  • Abdolhossein Rezaei Nejad, Ahmad Ismaili. Changes in growth, essential oil yield and composition of geranium (Pelargonium graveolens L.) as affected by growing media. Journal of the science of food and agriculture. 2014 Mar; 94(5):905-10. doi: 10.1002/jsfa.6334. [PMID: 23913545]
  • René F Ramos Alvarenga, Baojie Wan, Taichi Inui, Scott G Franzblau, Guido F Pauli, Birgit U Jaki. Airborne antituberculosis activity of Eucalyptus citriodora essential oil. Journal of natural products. 2014 Mar; 77(3):603-10. doi: 10.1021/np400872m. [PMID: 24641242]
  • Kanji Kubo, Kazuki Tsuji, Akira Mori, Seiji Ujiie. Synthesis and properties of cholesteryl 4-(Alkanoylamino)benzoates: liquid crystals and organogelators. Journal of oleo science. 2014; 63(4):401-6. doi: 10.5650/jos.ess13160. [PMID: 24599108]
  • Sandeep B Rajput, S Mohan Karuppayil. Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans. SpringerPlus. 2013 Dec; 2(1):26. doi: 10.1186/2193-1801-2-26. [PMID: 23449869]
  • Mohamed Nadjib Boukhatem, Abdelkrim Kameli, Mohamed Amine Ferhat, Fairouz Saidi, Maamar Mekarnia. Rose geranium essential oil as a source of new and safe anti-inflammatory drugs. The Libyan journal of medicine. 2013 10; 8(1):22520. doi: 10.3402/ljm.v8i0.22520. [PMID: 24103319]
  • Federica Pellati, Giulia Orlandini, Katryna A van Leeuwen, Giulia Anesin, Davide Bertelli, Mauro Paolini, Stefania Benvenuti, Federica Camin. Gas chromatography combined with mass spectrometry, flame ionization detection and elemental analyzer/isotope ratio mass spectrometry for characterizing and detecting the authenticity of commercial essential oils of Rosa damascena Mill. Rapid communications in mass spectrometry : RCM. 2013 Mar; 27(5):591-602. doi: 10.1002/rcm.6489. [PMID: 23413218]
  • Hafsia Bouzenna, Lamia Krichen. Pelargonium graveolens L'Her. and Artemisia arborescens L. essential oils: chemical composition, antifungal activity against Rhizoctonia solani and insecticidal activity against Rhysopertha dominica. Natural product research. 2013; 27(9):841-6. doi: 10.1080/14786419.2012.711325. [PMID: 22840199]
  • Anis Ben Hsouna, Naceur Hamdi. Phytochemical composition and antimicrobial activities of the essential oils and organic extracts from Pelargonium graveolens growing in Tunisia. Lipids in health and disease. 2012 Dec; 11(?):167. doi: 10.1186/1476-511x-11-167. [PMID: 23216669]
  • Renan G Brito, Adriana G Guimarães, Jullyana S S Quintans, Marcio R V Santos, Damião P De Sousa, Daniel Badaue-Passos, Waldecy de Lucca, Fabíola A Brito, Emiliano O Barreto, Aldeídia P Oliveira, Lucindo J Quintans. Citronellol, a monoterpene alcohol, reduces nociceptive and inflammatory activities in rodents. Journal of natural medicines. 2012 Oct; 66(4):637-44. doi: 10.1007/s11418-012-0632-4. [PMID: 22350215]
  • Eunae Kim, Il-Kwon Park. Fumigant antifungal activity of Myrtaceae essential oils and constituents from Leptospermum petersonii against three Aspergillus species. Molecules (Basel, Switzerland). 2012 Sep; 17(9):10459-69. doi: 10.3390/molecules170910459. [PMID: 22945026]
  • Wantida Chaiyana, Siriporn Okonogi. Inhibition of cholinesterase by essential oil from food plant. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2012 Jun; 19(8-9):836-9. doi: 10.1016/j.phymed.2012.03.010. [PMID: 22510493]
  • Jun Han, Soon-Il Kim, Byeoung-Ryeol Choi, Sang-Guei Lee, Young-Joon Ahn. Fumigant toxicity of lemon eucalyptus oil constituents to acaricide-susceptible and acaricide-resistant Tetranychus urticae. Pest management science. 2011 Dec; 67(12):1583-8. doi: 10.1002/ps.2216. [PMID: 21674753]
  • Ram Swaroop Verma, Rajendra Chandra Padalia, Amit Chauhan, Anand Singh, Ajai Kumar Yadav. Volatile constituents of essential oil and rose water of damask rose (Rosa damascena Mill.) cultivars from North Indian hills. Natural product research. 2011 Oct; 25(17):1577-84. doi: 10.1080/14786419.2010.520162. [PMID: 21711177]
  • Gajanan B Zore, Archana D Thakre, V Rathod, S Mohan Karuppayil. Evaluation of anti-Candida potential of geranium oil constituents against clinical isolates of Candida albicans differentially sensitive to fluconazole: inhibition of growth, dimorphism and sensitization. Mycoses. 2011 Jul; 54(4):e99-109. doi: 10.1111/j.1439-0507.2009.01852.x. [PMID: 20337938]
  • Paola Gonzalez-Audino, María Inés Picollo, Anabella Gallardo, Ariel Toloza, Claudia Vassena, Gastón Mougabure-Cueto. Comparative toxicity of oxygenated monoterpenoids in experimental hydroalcoholic lotions to permethrin-resistant adult head lice. Archives of dermatological research. 2011 Jul; 303(5):361-6. doi: 10.1007/s00403-010-1110-z. [PMID: 21174108]
  • Shalinder Kaur, Shivani Rana, Harminder Pal Singh, Daizy Rani Batish, Ravinder Kumar Kohli. Citronellol disrupts membrane integrity by inducing free radical generation. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2011 May; 66(5-6):260-6. doi: 10.1515/znc-2011-5-609. [PMID: 21812343]
  • Karina Caballero-Gallardo, Jesús Olivero-Verbel, Elena E Stashenko. Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst. Journal of agricultural and food chemistry. 2011 Mar; 59(5):1690-6. doi: 10.1021/jf103937p. [PMID: 21291237]
  • Michiko Katsukawa, Rieko Nakata, Satomi Koeji, Kazuyuki Hori, Saori Takahashi, Hiroyasu Inoue. Citronellol and geraniol, components of rose oil, activate peroxisome proliferator-activated receptor α and γ and suppress cyclooxygenase-2 expression. Bioscience, biotechnology, and biochemistry. 2011; 75(5):1010-2. doi: 10.1271/bbb.110039. [PMID: 21597168]
  • Hyland Cronin, Zoe Diana Draelos. Top 10 botanical ingredients in 2010 anti-aging creams. Journal of cosmetic dermatology. 2010 Sep; 9(3):218-25. doi: 10.1111/j.1473-2165.2010.00516.x. [PMID: 20883295]
  • M Spiller, R G Berger, Thomas Debener. Genetic dissection of scent metabolic profiles in diploid rose populations. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 2010 May; 120(7):1461-71. doi: 10.1007/s00122-010-1268-y. [PMID: 20084491]
  • Joana F A Bastos, Italo J A Moreira, Thaís P Ribeiro, Isac A Medeiros, Angelo R Antoniolli, Damião P De Sousa, Márcio R V Santos. Hypotensive and vasorelaxant effects of citronellol, a monoterpene alcohol, in rats. Basic & clinical pharmacology & toxicology. 2010 Apr; 106(4):331-7. doi: 10.1111/j.1742-7843.2009.00492.x. [PMID: 20002067]
  • Harminder P Singh, Sunil Mittal, Shalinder Kaur, Daizy R Batish, Ravinder K Kohli. Characterization and antioxidant activity of essential oils from fresh and decaying leaves of Eucalyptus tereticornis. Journal of agricultural and food chemistry. 2009 Aug; 57(15):6962-6. doi: 10.1021/jf9012407. [PMID: 19722579]
  • J H Jeon, C H Lee, H S Lee. Food protective effect of geraniol and its congeners against stored food mites. Journal of food protection. 2009 Jul; 72(7):1468-71. doi: 10.4315/0362-028x-72.7.1468. [PMID: 19681271]
  • Junheon Kim, Sang-Gil Lee, Sang-Chul Shin, Young-Dae Kwon, Il-Kwon Park. Male-produced aggregation pheromone blend in Platypus koryoensis. Journal of agricultural and food chemistry. 2009 Feb; 57(4):1406-12. doi: 10.1021/jf8032717. [PMID: 19170509]
  • Ju-Hyun Jeon, Hyung-Wook Kim, Min-Gi Kim, Hoi-Seon Lee. Mite-control activities of active constituents isolated from Pelargonium graveolens against house dust mites. Journal of microbiology and biotechnology. 2008 Oct; 18(10):1666-71. doi: ". [PMID: 18955817]
  • L J Quintans-Júnior, T T Souza, B S Leite, N M N Lessa, L R Bonjardim, M R V Santos, P B Alves, A F Blank, A R Antoniolli. Phythochemical screening and anticonvulsant activity of Cymbopogon winterianus Jowitt (Poaceae) leaf essential oil in rodents. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2008 Aug; 15(8):619-24. doi: 10.1016/j.phymed.2007.09.018. [PMID: 17976969]
  • Yamin Wang, Lunzhao Yi, Yizeng Liang, Hongdong Li, Dalin Yuan, Haiyan Gao, Maomao Zeng. Comparative analysis of essential oil components in Pericarpium Citri Reticulatae Viride and Pericarpium Citri Reticulatae by GC-MS combined with chemometric resolution method. Journal of pharmaceutical and biomedical analysis. 2008 Jan; 46(1):66-74. doi: 10.1016/j.jpba.2007.08.030. [PMID: 17942260]
  • Narendra Singh, Vijay K Kaul, Nima W Megeji, Virendra Singh, Paramvir S Ahuja. Essential oil composition of three accessions of Dracocephalum heterophyllum Benth. cultivated at Palampur, India. Natural product research. 2008; 22(11):927-36. doi: 10.1080/14786410701642847. [PMID: 18629706]
  • Ahmed El-Ghorab, Khaled F El-Massry, Takayuki Shibamoto. Chemical composition of the volatile extract and antioxidant activities of the volatile and nonvolatile extracts of Egyptian corn silk (Zea mays L.). Journal of agricultural and food chemistry. 2007 Oct; 55(22):9124-7. doi: 10.1021/jf071646e. [PMID: 17914872]
  • Om Prakash, Kirti Kumari, Rup Lal. Pseudomonas delhiensis sp. nov., from a fly ash dumping site of a thermal power plant. International journal of systematic and evolutionary microbiology. 2007 Mar; 57(Pt 3):527-531. doi: 10.1099/ijs.0.64456-0. [PMID: 17329778]
  • Naoko Yoshida, Mariya Koizumi, Isao Adachi, Junichi Kawakami. Inhibition of P-glycoprotein-mediated transport by terpenoids contained in herbal medicines and natural products. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2006 Dec; 44(12):2033-9. doi: 10.1016/j.fct.2006.07.003. [PMID: 16904803]
  • Damião Pergentino de Sousa, Juan Carlos Ramos Gonçalves, Lucindo Quintans-Júnior, Jader Santos Cruz, Demétrius Antonio Machado Araújo, Reinaldo Nóbrega de Almeida. Study of anticonvulsant effect of citronellol, a monoterpene alcohol, in rodents. Neuroscience letters. 2006 Jul; 401(3):231-5. doi: 10.1016/j.neulet.2006.03.030. [PMID: 16650577]
  • I Hierro, A Valero, M C Navarro. In vivo larvicidal activity of monoterpenic derivatives from aromatic plants against L3 larvae of Anisakis simplex s.l. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2006 Jul; 13(7):527-31. doi: 10.1016/j.phymed.2005.05.001. [PMID: 16785045]
  • Krzysztof Cal. Skin penetration of terpenes from essential oils and topical vehicles. Planta medica. 2006 Mar; 72(4):311-6. doi: 10.1055/s-2005-916230. [PMID: 16557471]
  • Naoko Yoshida, Akiyoshi Takagi, Hidenori Kitazawa, Junichi Kawakami, Isao Adachi. Inhibition of P-glycoprotein-mediated transport by extracts of and monoterpenoids contained in Zanthoxyli fructus. Toxicology and applied pharmacology. 2005 Dec; 209(2):167-73. doi: 10.1016/j.taap.2005.04.001. [PMID: 15890377]
  • Yuhong Tian, Xiongmin Liu, Yonghong Zhou, Zhanjing Guo. [Extraction and determination of volatile constituents in leaves of Eucalyptus citriodora]. Se pu = Chinese journal of chromatography. 2005 Nov; 23(6):651-4. doi: . [PMID: 16498999]
  • Christian Jung, Karl-Heinz Funken, Jürgen Ortner. PROPHIS: parabolic trough-facility for organic photochemical syntheses in sunlight. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. 2005 May; 4(5):409-11. doi: 10.1039/b500294j. [PMID: 15875073]
  • S Shin, S Lim. Antifungal effects of herbal essential oils alone and in combination with ketoconazole against Trichophyton spp. Journal of applied microbiology. 2004; 97(6):1289-96. doi: 10.1111/j.1365-2672.2004.02417.x. [PMID: 15546420]
  • Moshe Shalit, Inna Guterman, Hanne Volpin, Einat Bar, Tal Tamari, Naama Menda, Zach Adam, Dani Zamir, Alexander Vainstein, David Weiss, Eran Pichersky, Efraim Lewinsohn. Volatile ester formation in roses. Identification of an acetyl-coenzyme A. Geraniol/Citronellol acetyltransferase in developing rose petals. Plant physiology. 2003 Apr; 131(4):1868-76. doi: 10.1104/pp.102.018572. [PMID: 12692346]
  • Sushil K Kothari, Chandra P Singh, Kamla Singh. Weed control in rose-scented geranium (Pelargonium spp). Pest management science. 2002 Dec; 58(12):1254-8. doi: 10.1002/ps.592. [PMID: 12477000]
  • U Huss, T Ringbom, P Perera, L Bohlin, M Vasänge. Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay. Journal of natural products. 2002 Nov; 65(11):1517-21. doi: 10.1021/np020023m. [PMID: 12444669]
  • C L Cantrell, S G Franzblau, N H Fischer. Antimycobacterial plant terpenoids. Planta medica. 2001 Nov; 67(8):685-94. doi: 10.1055/s-2001-18365. [PMID: 11731906]
  • B M Botha, C M McCrindle. An appropriate method for extracting the insect repellent citronellol from an indigenous plant (Pelargonium graveolens L'Her) for potential use by resource-limited animal owners. Journal of the South African Veterinary Association. 2000 Jun; 71(2):103-5. doi: 10.4102/jsava.v71i2.688. [PMID: 11030360]
  • A King, J Richard Dickinson. Biotransformation of monoterpene alcohols by Saccharomyces cerevisiae, Torulaspora delbrueckii and Kluyveromyces lactis. Yeast (Chichester, England). 2000 Apr; 16(6):499-506. doi: 10.1002/(sici)1097-0061(200004)16:6<499::aid-yea548>3.0.co;2-e. [PMID: 10790686]
  • M D Green, D J Clarke, E M Oturu, P B Styczynski, M R Jackson, B Burchell, T R Tephly. Cloning and expression of a rat liver phenobarbital-inducible UDP-glucuronosyltransferase (2B12) with specificity for monoterpenoid alcohols. Archives of biochemistry and biophysics. 1995 Oct; 322(2):460-8. doi: 10.1006/abbi.1995.1489. [PMID: 7574722]
  • C Viollon, J P Chaumont. Antifungal properties of essential oils and their main components upon Cryptococcus neoformans. Mycopathologia. 1994 Dec; 128(3):151-3. doi: 10.1007/bf01138476. [PMID: 7739729]
  • J P Chaumont, D Léger. [Campaign against allergenic moulds in dwellings. Inhibitor properties of essential oil of Geranium 'Bourbon', citronellol, geraniol and citral]. Annales pharmaceutiques francaises. 1992; 50(3):156-66. doi: ". [PMID: 1290385]
  • J Vilaplana, C Romaguera, F Grimalt. Contact dermatitis from geraniol in Bulgarian rose oil. Contact dermatitis. 1991 Apr; 24(4):301. doi: 10.1111/j.1600-0536.1991.tb01726.x. [PMID: 1868720]
  • G Popják, C Hadley. Inhibition of liver prenyltransferase by citronellyl and geranyl phosphonate and phosphonylphosphate. Journal of lipid research. 1985 Sep; 26(9):1151-9. doi: ". [PMID: 4067435]
  • F van OS, E T ELEMA. [Determination of geraniol and citronellol in geranium- and citronella oil]. Pharmaceutisch weekblad. 1960 Nov; 95(?):761-9. doi: ". [PMID: 13731360]