Nookatone (BioDeep_00000000408)

 

Secondary id: BioDeep_00001867501

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, [4R-(4.alpha.,4a.alpha.,6.beta.)]-

化学式: C15H22O (218.1670562)
中文名称: (+)-诺卡酮, 努特卡酮, 诺卡酮, 努特卡酮, 诺卡酮
谱图信息: 最多检出来源 Viridiplantae(plant) 8.81%

分子结构信息

SMILES: C1C(=O)C=C2[C@]([C@@H]1C)(C[C@@H](CC2)C(=C)C)C
InChI: InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3

描述信息

Nootkatone is a natural organic compound and is the most important and expensive aromatic of grapefruit. It is a sesquiterpene and a ketone. Nootkatone was previously thought to be one of the main chemical components of the smell and flavour of grapefruits. In its solid form it is usually found as crystals. As a liquid, it is viscous and yellow. Nootkatone is typically extracted from grapefruit, but can also be manufactured with genetically modified organisms, or through the chemical or biochemical oxidation of valencene. It is also found in Alaska yellow cedar trees and vetiver grass.
(+)-nootkatone is a sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R stereoisomer). It has a role as a plant metabolite, a fragrance and an insect repellent. It is a sesquiterpenoid, an enone and a carbobicyclic compound.

Nootkatone is a natural product found in Teucrium asiaticum, Teucrium oxylepis, and other organisms with data available.

Constituent of grapefruit oil and juice. Flavouring ingredient. Nootkatone is found in many foods, some of which are citrus, sweet orange, lime, and lemon.

Nootkatone is an organic compound, a sesquiterpenoid, which means that it is a C15 derivative that also contains an oxygen-containing functional group (a ketone). It is the most valuable aroma compound of grapefruit.[2] Nootkatone was originally isolated from the wood of the Alaskan yellow cedar, Cupressus nootkatensis. The species name, nootkatensis, is derived from the language of the Nuu-Chah-Nulth people of Canada (formerly referred to as the Nootka people).[3]
Nootkatone, a neuroprotective agent from Vitis vinifera, has antioxidant and anti-inflammatory effects[1]. Nootkatone improves cognitive impairment in lipopolysaccharide-induced mouse model of Alzheimer's disease[2].
Nootkatone, a neuroprotective agent from Vitis vinifera, has antioxidant and anti-inflammatory effects[1]. Nootkatone improves cognitive impairment in lipopolysaccharide-induced mouse model of Alzheimer's disease[2].

同义名列表

52 个代谢物同义名

2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, [4R-(4.alpha.,4a.alpha.,6.beta.)]-; 2(3H)-NAPHTHALENONE, 4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLETHENYL)-, (4R-(4.ALPHA.,4A.ALPHA.,6.BETA.))-; 4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, [4R-(4.alpha.,4a.alpha.,6.beta.)]-; 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R-(4alpha,4aalpha,6beta))-; 6-Isopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone-, [4R-(4.alpha.,4a.alpha.,6.beta.)]-; 4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, (4R-(4alpha,4aalpha,6beta))-; (4R-(4alpha,4aalpha,6beta))-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylvinyl)naphthalen-2(3H)-one; (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone; Nootkanone; 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-rel; 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-; (4RS,4Asr,6RS)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone; (4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one; (4R,4aS,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one; 4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLENE-ETHYL)-2(3H)-NAPHTHALENONE; 4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one; 4a,5-Dimethyl-1,2,3,4,4a,5,6,7-octahydro-7-keto-3-isopropenylnaphthalene; 4,4A,5,6,7,8-HEXAHYDRO-6-ISO-PROPENYL-4,4A-DIMETHYL-2(3H)-NAPHTHALENONE; 4,4a,5,6,7,8-Hexahydro-6-isopropenyl-4,4a-dimethyl-2(3H)-naphthalenone; (+)-5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one; 5,6-DIMETHYL-8-ISOPROPENYL-BICYCLO(4,4,0)-DEC-1-EN-3-ONE; 5,6-Dimethyl-8-isopropenylbicyclo(4.4.0)dec-1-en-3-one; 4.beta.H,5.alpha.-Eremorphila-1(10)11-dien-2-one; 4.beta.H,5.alpha.-Eremophila-1(10),11-dien-2-one; nootkatone, (4R-(4alpha,4aalpha,6beta))-isomer; 4betaH,5alpha-Eremorphila-1(10)11-dien-2-one; 4Betah,5alpha-eremophila-1(10),11-dien-2-one; 7.BETA.H-EREMOPHILA-1(10),11-DIEN-2-ONE -; 7betaH-Eremophila-1(10),11-dien-2-one -; (+)-Nootkatone, technical, >=85\\% (GC); (+)-Nootkatone, analytical standard; 1(10),11-Eremophiladien-2-one; (+)-Nootkatone, >=99.0\\% (GC); (+)-Nootkatone, crystalline; Nootkatone (+/-)-form [MI]; Nootkatone, >=98\\%, FG; Nootkatone (natural); Nootkatone, (+/-)-; NOOTKATONE [FHFI]; Nootkatone, (+)-; (+/-)-Nootkatone; UNII-3K3OKV2A5A; NOOTKATONE [MI]; UNII-IZ2Y119N4J; (+)-Nootkatone; Tox21_302385; Nootkatone; 3K3OKV2A5A; Nootkatane; Nootkanone; IZ2Y119N4J; nootkaton; Nookatone



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

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)

47 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。



文献列表

  • Lingling Ma, Tao Wu, Peiling Liu, Dongying Chen, Shengliang Cai, Hefeng Chen, Jingtao Zhou, Chaoyi Zhu, Shuang Li. Green Production of a High-value Mosquito Insecticide of Nootkatone from Seaweed Hydrolysates. Journal of agricultural and food chemistry. 2023 Dec; 71(48):18919-18927. doi: 10.1021/acs.jafc.3c06708. [PMID: 37991146]
  • Xiaomin Deng, Ziling Ye, Jingyu Duan, Fangfang Chen, Yao Zhi, Man Huang, Minjian Huang, Weijia Cheng, Yujie Dou, Zhaolin Kuang, Yanglei Huang, Guangkai Bian, Zixin Deng, Tiangang Liu, Li Lu. Complete pathway elucidation and heterologous reconstitution of (+)-nootkatone biosynthesis from Alpinia oxyphylla. The New phytologist. 2023 Nov; ?(?):. doi: 10.1111/nph.19375. [PMID: 37933426]
  • Tongjie Xiao, Mingyu Pan, Yuanxiao Wang, Yanjiao Huang, Makoto Tsunoda, Yingxia Zhang, Rong Wang, Wenting Hu, Haimei Yang, Lu-Shuang Li, Yanting Song. In vitro bloodbrain barrier permeability study of four main active ingredients from Alpiniae oxyphyllae fructus. Journal of pharmaceutical and biomedical analysis. 2023 Aug; 235(?):115637. doi: 10.1016/j.jpba.2023.115637. [PMID: 37634356]
  • Ola A Habotta, Ahmed Abdeen, Aya A El-Hanafy, Neimet Yassin, Dina Elgameel, Samah F Ibrahim, Doaa Abdelrahaman, Tabinda Hasan, Florin Imbrea, Heba I Ghamry, Liana Fericean, Ali Behairy, Ahmed M Atwa, Afaf Abdelkader, Mohamed R Mahdi, Shaaban A El-Mosallamy. Sesquiterpene nootkatone counteracted the melamine-induced neurotoxicity via repressing of oxidative stress, inflammatory, and apoptotic trajectories. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Jul; 165(?):115133. doi: 10.1016/j.biopha.2023.115133. [PMID: 37454594]
  • Fapetu Kemi Busayo, Jin-Ling Yang, Xu-Po Ding, Ya-Li Wang, Cui-Juan Gai, Fei Wu, Hao-Fu Dai, Wen-Li Mei, Hui-Qin Chen. Identification of volatile compounds and their bioactivities from unpolar fraction of Alpinia oxyphylla Miq. and mining key genes of nootkatone biosynthesis. Natural product research. 2023 Jun; ?(?):1-6. doi: 10.1080/14786419.2023.2220063. [PMID: 37278024]
  • Adela S Oliva Chávez, Stephanie Guzman Valencia, Geoffrey E Lynn, Charluz Arocho Rosario, Donald B Thomas, Tammi L Johnson. Evaluation of the in vitro acaricidal effect of five organic compounds on the cattle fever tick Rhipicephalus (Boophilus) microplus (Acari: Ixodidae). Experimental & applied acarology. 2023 Apr; 89(3-4):447-460. doi: 10.1007/s10493-023-00780-9. [PMID: 37052726]
  • Xin-Hua Zhao, Na An, Meng-Huan Xia, Wen-Ping Liu, Qing-Qi Wang, Ji-Zhang Bao. Nootkatone Improves Chronic Unpredictable Mild Stress-Induced Depressive-Like Behaviors by Repressing NF-κB/NLRP3-Mediated Neuroinflammation. Chinese journal of integrative medicine. 2023 Jan; 29(1):37-43. doi: 10.1007/s11655-022-3725-2. [PMID: 36401752]
  • Ankush Kumar Jha, Shobhit Gairola, Sourav Kundu, Pakpi Doye, Abu Mohammad Syed, Chetan Ram, Uttam Kulhari, Naresh Kumar, Upadhyayula Suryanarayana Murty, Bidya Dhar Sahu. Biological Activities, Pharmacokinetics and Toxicity of Nootkatone: A Review. Mini reviews in medicinal chemistry. 2022; 22(17):2244-2259. doi: 10.2174/1389557522666220214092005. [PMID: 35156582]
  • Zhen-Miao Qin, Yong-Hui Li, Yin-Feng Tan, Hai-Long Li. Determination of nootkatone in rat plasma by LC-tandem mass spectrometry and its application in a pharmacokinetic study. Biomedical chromatography : BMC. 2021 Dec; 35(12):e5197. doi: 10.1002/bmc.5197. [PMID: 34162012]
  • Shobhit Gairola, Chetan Ram, Abu Mohammad Syed, Pakpi Doye, Uttam Kulhari, Madhav Nilakanth Mugale, Upadhyayula Suryanarayana Murty, Bidya Dhar Sahu. Nootkatone confers antifibrotic effect by regulating the TGF-β/Smad signaling pathway in mouse model of unilateral ureteral obstruction. European journal of pharmacology. 2021 Nov; 910(?):174479. doi: 10.1016/j.ejphar.2021.174479. [PMID: 34480883]
  • Chang-Mu Chen, Chen-Yu Lin, Yao-Pang Chung, Chia-Hung Liu, Kuo-Tong Huang, Siao-Syun Guan, Cheng-Tien Wu, Shing-Hwa Liu. Protective Effects of Nootkatone on Renal Inflammation, Apoptosis, and Fibrosis in a Unilateral Ureteral Obstructive Mouse Model. Nutrients. 2021 Nov; 13(11):. doi: 10.3390/nu13113921. [PMID: 34836176]
  • Xiao Li, Jing-Nan Ren, Gang Fan, Lu-Lu Zhang, Si-Yi Pan. Advances on (+)-nootkatone microbial biosynthesis and its related enzymes. Journal of industrial microbiology & biotechnology. 2021 Aug; 48(7-8):. doi: 10.1093/jimb/kuab046. [PMID: 34279658]
  • Yuqin Gou, Fangyuan Zhang, Yueli Tang, Chunxue Jiang, Ge Bai, He Xie, Min Chen, Zhihua Liao. Engineering Nootkatone Biosynthesis in Artemisia annua. ACS synthetic biology. 2021 05; 10(5):957-963. doi: 10.1021/acssynbio.1c00016. [PMID: 33973783]
  • Tingxu Yan, Fuyuan Li, Weilin Xiong, Bo Wu, Feng Xiao, Bosai He, Ying Jia. Nootkatone improves anxiety- and depression-like behavior by targeting hyperammonemia-induced oxidative stress in D-galactosamine model of liver injury. Environmental toxicology. 2021 Apr; 36(4):694-706. doi: 10.1002/tox.23073. [PMID: 33270352]
  • M F Nagoor Meeran, Sheikh Azimullah, Ernest Adeghate, Shreesh Ojha. Nootkatone attenuates myocardial oxidative damage, inflammation, and apoptosis in isoproterenol-induced myocardial infarction in rats. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Apr; 84(?):153405. doi: 10.1016/j.phymed.2020.153405. [PMID: 33636578]
  • Jung-Eun Park, Jin-Sun Park, Yea-Hyun Leem, Do-Yeon Kim, Hee-Sun Kim. NQO1 mediates the anti-inflammatory effects of nootkatone in lipopolysaccharide-induced neuroinflammation by modulating the AMPK signaling pathway. Free radical biology & medicine. 2021 02; 164(?):354-368. doi: 10.1016/j.freeradbiomed.2021.01.015. [PMID: 33460769]
  • Megan C Dyer, Matthew D Requintina, Kathryn A Berger, Gavino Puggioni, Thomas N Mather. Evaluating the Effects of Minimal Risk Natural Products for Control of the Tick, Ixodes scapularis (Acari: Ixodidae). Journal of medical entomology. 2021 01; 58(1):390-397. doi: 10.1093/jme/tjaa188. [PMID: 33044507]
  • Samer S Habash, Philipp P Könen, Anita Loeschcke, Matthias Wüst, Karl-Erich Jaeger, Thomas Drepper, Florian M W Grundler, A Sylvia S Schleker. The Plant Sesquiterpene Nootkatone Efficiently Reduces Heterodera schachtii Parasitism by Activating Plant Defense. International journal of molecular sciences. 2020 Dec; 21(24):. doi: 10.3390/ijms21249627. [PMID: 33348829]
  • M F Nagoor Meeran, Sheikh Azimullah, M Marzouq Al Ahbabi, Niraj Kumar Jha, Vinoth-Kumar Lakshmanan, Sameer N Goyal, Shreesh Ojha. Nootkatone, a Dietary Fragrant Bioactive Compound, Attenuates Dyslipidemia and Intramyocardial Lipid Accumulation and Favorably Alters Lipid Metabolism in a Rat Model of Myocardial Injury: An In Vivo and In Vitro Study. Molecules (Basel, Switzerland). 2020 Nov; 25(23):. doi: 10.3390/molecules25235656. [PMID: 33266249]
  • Eunsu Yoo, Jaehak Lee, Pattawika Lertpatipanpong, Junsun Ryu, Chong-Tai Kim, Eul-Yong Park, Seung Joon Baek. Anti-proliferative activity of A. Oxyphylla and its bioactive constituent nootkatone in colorectal cancer cells. BMC cancer. 2020 Sep; 20(1):881. doi: 10.1186/s12885-020-07379-y. [PMID: 32928152]
  • Raena Morley, Mirjana Minceva. Trapping multiple dual mode liquid-liquid chromatography: Preparative separation of nootkatone from a natural product extract. Journal of chromatography. A. 2020 Aug; 1625(?):461272. doi: 10.1016/j.chroma.2020.461272. [PMID: 32709324]
  • Yu Qi, Xinhui Cheng, Guowei Gong, Tingxu Yan, Yiyang Du, Bo Wu, Kaishun Bi, Ying Jia. Synergistic neuroprotective effect of schisandrin and nootkatone on regulating inflammation, apoptosis and autophagy via the PI3K/AKT pathway. Food & function. 2020 Mar; 11(3):2427-2438. doi: 10.1039/c9fo02927c. [PMID: 32129354]
  • Xiangfeng Meng, Hui Liu, Wenqiang Xu, Weixin Zhang, Zheng Wang, Weifeng Liu. Metabolic engineering Saccharomyces cerevisiae for de novo production of the sesquiterpenoid (+)-nootkatone. Microbial cell factories. 2020 Feb; 19(1):21. doi: 10.1186/s12934-020-1295-6. [PMID: 32013959]
  • Xiangxiang Zhu, Xiangyun Li, Zhen Chen. Inhibition of anticancer growth in Retinoblastoma cells by naturally occurring sesquiterpene nootkatone is mediated via autophagy, endogenous ROS production, cell cycle arrest and inhibition of NF-κB signalling pathway. Journal of B.U.ON. : official journal of the Balkan Union of Oncology. 2020 Jan; 25(1):427-431. doi: . [PMID: 32277665]
  • Haipeng Zhang, Huan Wen, Jiajing Chen, Zhaoxin Peng, Meiyan Shi, Mengjun Chen, Ziyu Yuan, Yuan Liu, Hongyan Zhang, Juan Xu. Volatile Compounds in Fruit Peels as Novel Biomarkers for the Identification of Four Citrus Species. Molecules (Basel, Switzerland). 2019 Dec; 24(24):. doi: 10.3390/molecules24244550. [PMID: 31842378]
  • Yu Qi, Xinhui Cheng, Huiting Jing, Tingxu Yan, Feng Xiao, Bo Wu, Kaishun Bi, Ying Jia. Combination of schisandrin and nootkatone exerts neuroprotective effect in Alzheimer's disease mice model. Metabolic brain disease. 2019 12; 34(6):1689-1703. doi: 10.1007/s11011-019-00475-4. [PMID: 31422511]
  • Badreldin H Ali, Suhail Al-Salam, Sirin A Adham, Khalid Al Balushi, Mohammed Al Za'abi, Sumaya Beegam, Priya Yuvaraju, Priyadarsini Manoj, Abderrahim Nemmar. Testicular Toxicity of Water Pipe Smoke Exposure in Mice and the Effect of Treatment with Nootkatone Thereon. Oxidative medicine and cellular longevity. 2019; 2019(?):2416935. doi: 10.1155/2019/2416935. [PMID: 31341528]
  • Abderrahim Nemmar, Suhail Al-Salam, Sumaya Beegam, Priya Yuvaraju, Badreldin H Ali. Thrombosis and systemic and cardiac oxidative stress and DNA damage induced by pulmonary exposure to diesel exhaust particles and the effect of nootkatone thereon. American journal of physiology. Heart and circulatory physiology. 2018 05; 314(5):H917-H927. doi: 10.1152/ajpheart.00313.2017. [PMID: 29351455]
  • Ansgar Rühlmann, Georg Groth, Vlada B Urlacher. Characterization of CYP154F1 from Thermobifida fusca YX and Extension of Its Substrate Spectrum by Site-Directed Mutagenesis. Chembiochem : a European journal of chemical biology. 2018 03; 19(5):478-485. doi: 10.1002/cbic.201700565. [PMID: 29266604]
  • Alexander Schifrin, Martin Litzenburger, Michael Ringle, Thuy T B Ly, Rita Bernhardt. New Sesquiterpene Oxidations with CYP260A1 and CYP264B1 from Sorangium cellulosum So ce56. Chembiochem : a European journal of chemical biology. 2015 Dec; 16(18):2624-32. doi: 10.1002/cbic.201500417. [PMID: 26449371]
  • Robin-Hagen Leonhardt, Ralf G Berger. Nootkatone. Advances in biochemical engineering/biotechnology. 2015; 148(?):391-404. doi: 10.1007/10_2014_279. [PMID: 25326849]
  • Yogini Jaiswal, Zhitao Liang, Ping Guo, Hing-Man Ho, Hubiao Chen, Zhongzhen Zhao. Tissue-specific metabolite profiling of Cyperus rotundus L. rhizomes and (+)-nootkatone quantitation by laser microdissection, ultra-high-performance liquid chromatography-quadrupole time-of-flight mass spectrometry, and gas chromatography-mass spectrometry techniques. Journal of agricultural and food chemistry. 2014 Jul; 62(29):7302-16. doi: 10.1021/jf502494z. [PMID: 24938835]
  • Tamara Wriessnegger, Peter Augustin, Matthias Engleder, Erich Leitner, Monika Müller, Iwona Kaluzna, Martin Schürmann, Daniel Mink, Günther Zellnig, Helmut Schwab, Harald Pichler. Production of the sesquiterpenoid (+)-nootkatone by metabolic engineering of Pichia pastoris. Metabolic engineering. 2014 Jul; 24(?):18-29. doi: 10.1016/j.ymben.2014.04.001. [PMID: 24747046]
  • Katarina Cankar, Adèle van Houwelingen, Miriam Goedbloed, Rokus Renirie, René M de Jong, Harro Bouwmeester, Dirk Bosch, Theo Sonke, Jules Beekwilder. Valencene oxidase CYP706M1 from Alaska cedar (Callitropsis nootkatensis). FEBS letters. 2014 Mar; 588(6):1001-7. doi: 10.1016/j.febslet.2014.01.061. [PMID: 24530525]
  • Jules Beekwilder, Adèle van Houwelingen, Katarina Cankar, Aalt D J van Dijk, René M de Jong, Geert Stoopen, Harro Bouwmeester, Jihane Achkar, Theo Sonke, Dirk Bosch. Valencene synthase from the heartwood of Nootka cypress (Callitropsis nootkatensis) for biotechnological production of valencene. Plant biotechnology journal. 2014 Feb; 12(2):174-82. doi: 10.1111/pbi.12124. [PMID: 24112147]
  • Junqing Zhang, Sheng Wang, Yonghui Li, Peng Xu, Feng Chen, Yinfeng Tan, Jinao Duan. Anti-diarrheal constituents of Alpinia oxyphylla. Fitoterapia. 2013 Sep; 89(?):149-56. doi: 10.1016/j.fitote.2013.04.001. [PMID: 23583435]
  • Carole Gavira, René Höfer, Agnès Lesot, Fanny Lambert, Joseph Zucca, Danièle Werck-Reichhart. Challenges and pitfalls of P450-dependent (+)-valencene bioconversion by Saccharomyces cerevisiae. Metabolic engineering. 2013 Jul; 18(?):25-35. doi: 10.1016/j.ymben.2013.02.003. [PMID: 23518241]
  • Anuja Bharadwaj, Kirby C Stafford, Robert W Behle. Efficacy and environmental persistence of nootkatone for the control of the blacklegged tick (Acari: Ixodidae) in residential landscapes. Journal of medical entomology. 2012 Sep; 49(5):1035-44. doi: 10.1603/me11251. [PMID: 23025184]
  • Robert A Jordan, Terry L Schulze, Marc C Dolan. Efficacy of plant-derived and synthetic compounds on clothing as repellents against Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae). Journal of medical entomology. 2012 Jan; 49(1):101-6. doi: 10.1603/me10241. [PMID: 22308777]
  • Terry L Schulze, Robert A Jordan, Marc C Dolan. Experimental use of two standard tick collection methods to evaluate the relative effectiveness of several plant-derived and synthetic repellents against Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae). Journal of economic entomology. 2011 Dec; 104(6):2062-7. doi: 10.1603/ec10421. [PMID: 22299371]
  • Robert W Behle, Lina B Flor-Weiler, Anuja Bharadwaj, Kirby C Stafford. A formulation to encapsulate nootkatone for tick control. Journal of medical entomology. 2011 Nov; 48(6):1120-7. doi: 10.1603/me10282. [PMID: 22238870]
  • Konstantin Tsoyi, Hwa Jin Jang, Young Soo Lee, Young Min Kim, Hye Jung Kim, Han Geuk Seo, Jae Heun Lee, Jong Hwan Kwak, Dong-Ung Lee, Ki Churl Chang. (+)-Nootkatone and (+)-valencene from rhizomes of Cyperus rotundus increase survival rates in septic mice due to heme oxygenase-1 induction. Journal of ethnopharmacology. 2011 Oct; 137(3):1311-7. doi: 10.1016/j.jep.2011.07.062. [PMID: 21843620]
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