2-Undecanone (BioDeep_00000001093)

 

Secondary id: BioDeep_00000860079

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


2-Undecanone, analytical standard

化学式: C11H22O (170.1671)
中文名称: 甲基壬基甲酮, 2-十一烷
谱图信息: 最多检出来源 Homo sapiens(lipidsearch) 18.99%

分子结构信息

SMILES: CC(=O)CCCCCCCCC
InChI: InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3

描述信息

2-Undecanone is found in cloves. 2-Undecanone is found in palm kernel oil and soya bean oil. 2-Undecanone is an important constituent of rue oil (Ruta graveolens) and found in many other essential oils. Also found in black currant buds, raspberry, black berry peach and other fruits. 2-Undecanone is used in flavourings 2-Undecanone is a ketone, also known as methyl nonyl ketone (MNK). It is soluble in ethanol, benzene, chloroform, and acetone, but its large carbon chain renders it insoluble in water. Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a base. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide. 2-Undecanone, also known as methyl nonyl ketone and IBI-246, is an oily organic liquid manufactured synthetically, but which can also be extracted from oil of rue. It is found naturally in bananas, cloves, ginger, guava, strawberries, and wild-grown tomatoes. 2-Undecanone is used in the perfumery and flavoring industries, but because of its strong odor it is primarily used as an insect repellent or animal repellent. Typically, 1 2\\\\% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, aerosol spray, or gel.
Undecan-2-one is a dialkyl ketone with methyl and nonyl as the two alkyl groups. It has a role as a rodenticide and a plant metabolite. It is a dialkyl ketone and a methyl ketone.
2-Undecanone is a natural product found in Zanthoxylum myriacanthum, Eupatorium capillifolium, and other organisms with data available.
2-Undecanone is a metabolite found in or produced by Saccharomyces cerevisiae.
Found in palm kernel oil and soya bean oil. Important constituent of rue oil (Ruta graveolens) and found in many other essential oils. Also found in black currant buds, raspberry, black berry peach and other fruits. It is used in flavourings
A dialkyl ketone with methyl and nonyl as the two alkyl groups.
2-Undecanone is a volatile organic compound, which inhibits the DnaKJE-ClpB bichaperone dependent refolding of heat-inactivated bacterial luciferases. 2-Undecanone inhibits lung tumorigenesis[1][2].
2-Undecanone is a volatile organic compound, which inhibits the DnaKJE-ClpB bichaperone dependent refolding of heat-inactivated bacterial luciferases. 2-Undecanone inhibits lung tumorigenesis[1][2].

同义名列表

39 个代谢物同义名

2-Undecanone, analytical standard; 2-Undecanone, natural, FCC, FG; 2-Undecanone, >=98\\%, FCC, FG; MGK Dog and Cat Repellent; METHYL NONYL KETONE [MI]; Mgk dog & cat repellent; 2-Methylundecanone,(S); 2-Undecanone (natural); METHYL N-NONYL KETONE; Methyl-n-nonylketone; Ketone, methyl nonyl; methyl n-nonylketone; 2-UNDECANONE [HSDB]; 2-UNDECANONE [FHFI]; Nonyl methyl ketone; methyl nonyl ketone; 2-Undecanone, 99\\%; 2-UNDECANONE [FCC]; Methylnonylketone; UNII-YV5DSO8CY9; MGK dog AMP MNK; UNDECANONE, 2-; Undecanone-(2); 2-Oxoundecane; undecan-2-one; 2-Hendecanone; Tox21_301385; 2-Undecanone; Rue ketone; UNDECANONE; YV5DSO8CY9; FEMA 3093; AI3-03081; WLN: 9V1; Luparone; Enodyl; BioUD; 2-Undecanone; 2-Undecanone



数据库引用编号

29 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)

63 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 8 AKT1, CLPB, HPGDS, IL13, MTOR, PRPF19, TLR4, TMEM216
Peripheral membrane protein 3 ACHE, CYP1B1, MTOR
Endosome membrane 1 TLR4
Endoplasmic reticulum membrane 4 CYP1B1, HMOX1, ITPR1, MTOR
Nucleus 8 ACHE, AKT1, GABPA, HMOX1, KDR, MTOR, PLCZ1, PRPF19
cytosol 6 AKT1, HMOX1, HPGDS, MTOR, PLCZ1, TMEM216
dendrite 1 MTOR
phagocytic vesicle 1 MTOR
nucleoplasm 7 AKT1, GABPA, HMOX1, HPGDS, MTOR, PLCZ1, PRPF19
Cell membrane 4 ACHE, AKT1, KDR, TLR4
Cytoplasmic side 2 HMOX1, MTOR
lamellipodium 1 AKT1
Multi-pass membrane protein 2 ITPR1, TMEM216
Golgi apparatus membrane 1 MTOR
Synapse 1 ACHE
cell cortex 1 AKT1
cell junction 1 KDR
cell surface 2 ACHE, TLR4
glutamatergic synapse 1 AKT1
Golgi apparatus 3 ACHE, ATRN, KDR
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
neuromuscular junction 1 ACHE
postsynapse 1 AKT1
Lysosome 1 MTOR
endosome 1 KDR
plasma membrane 7 ACHE, AKT1, ATRN, IGHE, ITPR1, KDR, TLR4
Membrane 9 ACHE, AKT1, CYP1B1, HMOX1, ITPR1, MTOR, PRPF19, TLR4, TMEM216
extracellular exosome 1 ATRN
Lysosome membrane 1 MTOR
endoplasmic reticulum 3 HMOX1, ITPR1, KDR
extracellular space 8 ACHE, ATRN, HMOX1, IGHE, IL10, IL13, IL4, IL5
perinuclear region of cytoplasm 5 ACHE, HMOX1, ITPR1, PLCZ1, TLR4
Schaffer collateral - CA1 synapse 1 ITPR1
mitochondrion 2 CLPB, CYP1B1
protein-containing complex 1 AKT1
intracellular membrane-bounded organelle 2 CYP1B1, HPGDS
Microsome membrane 2 CYP1B1, MTOR
postsynaptic density 1 ITPR1
pronucleus 1 PLCZ1
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 3 ATRN, IGHE, TLR4
Secreted 5 ACHE, IL10, IL13, IL4, IL5
extracellular region 7 ACHE, IGHE, IL10, IL13, IL4, IL5, KDR
Mitochondrion outer membrane 1 MTOR
mitochondrial outer membrane 2 HMOX1, MTOR
[Isoform 2]: Secreted 2 ATRN, KDR
Extracellular side 1 ACHE
anchoring junction 1 KDR
external side of plasma membrane 3 IL13, KDR, TLR4
calcineurin complex 1 ITPR1
microtubule cytoskeleton 1 AKT1
nucleolus 2 ITPR1, PLCZ1
Early endosome 2 KDR, TLR4
cell-cell junction 1 AKT1
vesicle 1 AKT1
Cytoplasm, perinuclear region 2 ITPR1, PLCZ1
Membrane raft 1 KDR
Cytoplasm, cytoskeleton, spindle 1 PRPF19
spindle 2 AKT1, PRPF19
basement membrane 1 ACHE
sarcoplasmic reticulum 1 ITPR1
Nucleus, PML body 1 MTOR
PML body 1 MTOR
Mitochondrion intermembrane space 2 AKT1, CLPB
mitochondrial intermembrane space 2 AKT1, CLPB
nuclear speck 1 PRPF19
nuclear inner membrane 1 ITPR1
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 2 KDR, TLR4
ciliary basal body 1 AKT1
cilium 1 TMEM216
chromatin 1 GABPA
IgE immunoglobulin complex 1 IGHE
cell projection 1 TMEM216
phagocytic cup 1 TLR4
cytoskeleton 1 TMEM216
Cytoplasm, cytoskeleton, cilium basal body 1 TMEM216
ciliary transition zone 1 TMEM216
Lipid-anchor, GPI-anchor 1 ACHE
spliceosomal complex 1 PRPF19
[Isoform 2]: Cell membrane 1 IGHE
site of double-strand break 1 PRPF19
[Isoform 3]: Secreted 1 ATRN
nuclear envelope 1 MTOR
Endomembrane system 2 ITPR1, MTOR
sorting endosome 1 KDR
Lipid droplet 1 PRPF19
Nucleus, nucleoplasm 1 PRPF19
side of membrane 1 ACHE
platelet dense granule membrane 1 ITPR1
lipopolysaccharide receptor complex 1 TLR4
secretory granule membrane 1 ITPR1
Single-pass type IV membrane protein 1 HMOX1
platelet dense tubular network membrane 1 ITPR1
MKS complex 1 TMEM216
synaptic cleft 1 ACHE
U2-type catalytic step 1 spliceosome 1 PRPF19
[Isoform 1]: Cell membrane 1 ATRN
catalytic step 2 spliceosome 1 PRPF19
Cytoplasmic vesicle, secretory vesicle membrane 1 ITPR1
Prp19 complex 1 PRPF19
U2-type catalytic step 2 spliceosome 1 PRPF19
Cytoplasmic vesicle, phagosome 1 MTOR
[Isoform 3]: Cell membrane 1 IGHE
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
transport vesicle membrane 1 ITPR1
sperm head 1 PLCZ1
platelet dense tubular network 1 ITPR1
[Isoform H]: Cell membrane 1 ACHE


文献列表

  • Aigerim Kurmanbayeva, Meirambek Ospanov, Prabin Tamang, Farhan Mahmood Shah, Abbas Ali, Zeyad M A Ibrahim, Charles L Cantrell, Satmbekova Dinara, Ubaidilla Datkhayev, Ikhlas A Khan, Mohamed A Ibrahim. Regioselective Claisen-Schmidt Adduct of 2-Undecanone from Houttuynia cordata Thunb as Insecticide/Repellent against Solenopsis invicta and Repositioning Plant Fungicides against Colletotrichum fragariae. Molecules (Basel, Switzerland). 2023 Aug; 28(16):. doi: 10.3390/molecules28166100. [PMID: 37630353]
  • K Walkowiak-Nowicka, J Mirek, Sz Chowański, R Sobkowiak, M Słocińska. Plant secondary metabolites as potential bioinsecticides? Study of the effects of plant-derived volatile organic compounds on the reproduction and behaviour of the pest beetle Tenebrio molitor. Ecotoxicology and environmental safety. 2023 Jun; 257(?):114951. doi: 10.1016/j.ecoenv.2023.114951. [PMID: 37116454]
  • 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]
  • Chen-Hsiang Lin, Louis Kuoping Chao, Li-Yun Lin, Chin-Sheng Wu, Lee-Ping Chu, Chien-Hsueh Huang, Hsin-Chun Chen. Analysis of Volatile Compounds from Different Parts of Houttuynia cordata Thunb. Molecules (Basel, Switzerland). 2022 Dec; 27(24):. doi: 10.3390/molecules27248893. [PMID: 36558024]
  • Xueyan Wu, Jing Li, Shaopeng Wang, Liping Jiang, Xiance Sun, Xiaofang Liu, Xiaofeng Yao, Cong Zhang, Ningning Wang, Guang Yang. 2-Undecanone Protects against Fine Particle-Induced Kidney Inflammation via Inducing Mitophagy. Journal of agricultural and food chemistry. 2021 May; 69(17):5206-5215. doi: 10.1021/acs.jafc.1c01305. [PMID: 33877841]
  • Yanmei Lou, Zhenzhen Guo, Yuanfeng Zhu, Muyan Kong, Rongrong Zhang, Linlin Lu, Feichi Wu, Zhongqiu Liu, Jinjun Wu. Houttuynia cordata Thunb. and its bioactive compound 2-undecanone significantly suppress benzo(a)pyrene-induced lung tumorigenesis by activating the Nrf2-HO-1/NQO-1 signaling pathway. Journal of experimental & clinical cancer research : CR. 2019 Jun; 38(1):242. doi: 10.1186/s13046-019-1255-3. [PMID: 31174565]
  • Nemesio Villa-Ruano, Yesenia Pacheco-Hernández, José Alejo Zárate-Reyes, Ramiro Cruz-Durán, Edmundo Lozoya-Gloria. Volatile Composition and Biological Activities of the Leaf Essential Oil from Zanthoxylum limoncello Grown in Oaxaca, México. Chemistry & biodiversity. 2019 Feb; 16(2):e1800498. doi: 10.1002/cbdv.201800498. [PMID: 30512233]
  • Robert Sobkowiak, Natalia Bojarska, Emilia Krzyżaniak, Karolina Wągiel, Nikoletta Ntalli. Chemoreception of botanical nematicides by Meloidogyne incognita and Caenorhabditis elegans. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2018 Aug; 53(8):493-502. doi: 10.1080/03601234.2018.1462936. [PMID: 29708833]
  • Jiwei Zhu, Anirudh Dhammi, Jaap B van Kretschmar, Edward L Vargo, Charles S Apperson, R Michael Roe. Novel use of aliphatic n-methyl ketones as a fumigant and alternative to methyl bromide for insect control. Pest management science. 2018 Mar; 74(3):648-657. doi: 10.1002/ps.4749. [PMID: 28967211]
  • Zineb Bennaoum, Hachemi Benhassaini, Danilo Falconieri, Alessandra Piras, Silvia Porcedda. Chemical variability in essential oils from Ruta species among seasons, and its taxonomic and ecological significance. Natural product research. 2017 Oct; 31(19):2329-2334. doi: 10.1080/14786419.2017.1303692. [PMID: 28338346]
  • Paola Fincheira, Leonardo Parra, Ana Mutis, Maribel Parada, Andrés Quiroz. Volatiles emitted by Bacillus sp. BCT9 act as growth modulating agents on Lactuca sativa seedlings. Microbiological research. 2017 Oct; 203(?):47-56. doi: 10.1016/j.micres.2017.06.007. [PMID: 28754207]
  • Olga E Melkina, Inessa A Khmel, Vladimir A Plyuta, Olga A Koksharova, Gennadii B Zavilgelsky. Ketones 2-heptanone, 2-nonanone, and 2-undecanone inhibit DnaK-dependent refolding of heat-inactivated bacterial luciferases in Escherichia coli cells lacking small chaperon IbpB. Applied microbiology and biotechnology. 2017 Jul; 101(14):5765-5771. doi: 10.1007/s00253-017-8350-1. [PMID: 28577028]
  • Vishal Kumar, S G Eswara Reddy, Urvashi Chauhan, Neeraj Kumar, Bikram Singh. Chemical composition and larvicidal activity of Zanthoxylum armatum against diamondback moth, Plutella xylostella. Natural product research. 2016; 30(6):689-92. doi: 10.1080/14786419.2015.1036270. [PMID: 25920469]
  • Se Yeon Oh. An Effective Quality Control of Pharmacologically Active Volatiles of Houttuynia cordata Thunb by Fast Gas Chromatography-Surface Acoustic Wave Sensor. Molecules (Basel, Switzerland). 2015 Jun; 20(6):10298-312. doi: 10.3390/molecules200610298. [PMID: 26046325]
  • George F Antonious, John C Snyder. Repellency and oviposition deterrence of wild tomato leaf extracts to spider mites, Tetranychus urticae Koch. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2015; 50(9):667-73. doi: 10.1080/03601234.2015.1038960. [PMID: 26079341]
  • Wafa Bouabidi, Mohsen Hanana, Samia Gargouri, Ismail Amri, Tarek Fezzani, Mustapha Ksontini, Bassem Jamoussi, Lamia Hamrouni. Chemical composition, phytotoxic and antifungal properties of Ruta chalepensis L. essential oils. Natural product research. 2015; 29(9):864-8. doi: 10.1080/14786419.2014.980246. [PMID: 25553803]
  • Sana Bouajaj, Abderrahmane Romane, Abdennaji Benyamna, Ismail Amri, Mohsen Hanana, Lamia Hamrouni, Mehrez Romdhane. Essential oil composition, phytotoxic and antifungal activities of Ruta chalepensis L. leaves from High Atlas Mountains (Morocco). Natural product research. 2014; 28(21):1910-4. doi: 10.1080/14786419.2014.945085. [PMID: 25109925]
  • Daniela Fischer, Christian Imholt, Hans-Joachim Pelz, Michael Wink, Andreas Prokop, Jens Jacob. The repelling effect of plant secondary metabolites on water voles, Arvicola amphibius. Pest management science. 2013 Mar; 69(3):437-43. doi: 10.1002/ps.3438. [PMID: 23225271]
  • Daniela Fischer, Christian Imholt, Andreas Prokop, Jens Jacob. Efficacy of methyl nonyl ketone as an in-soil repellent for common voles (Microtus arvalis). Pest management science. 2013 Mar; 69(3):431-6. doi: 10.1002/ps.3426. [PMID: 23292923]
  • Teresa Weise, Marco Kai, Anja Gummesson, Armin Troeger, Stephan von Reuß, Silvia Piepenborn, Francine Kosterka, Martin Sklorz, Ralf Zimmermann, Wittko Francke, Birgit Piechulla. Volatile organic compounds produced by the phytopathogenic bacterium Xanthomonas campestris pv. vesicatoria 85-10. Beilstein journal of organic chemistry. 2012; 8(?):579-96. doi: 10.3762/bjoc.8.65. [PMID: 22563356]
  • Martin Pareja, Erika Qvarfordt, Ben Webster, Patrick Mayon, John Pickett, Michael Birkett, Robert Glinwood. Herbivory by a Phloem-feeding insect inhibits floral volatile production. PloS one. 2012; 7(2):e31971. doi: 10.1371/journal.pone.0031971. [PMID: 22384116]
  • Mayanka Walia, Tavleen S Mann, Dharmesh Kumar, Vijai K Agnihotri, Bikram Singh. Chemical Composition and In Vitro Cytotoxic Activity of Essential Oil of Leaves of Malus domestica Growing in Western Himalaya (India). Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):649727. doi: 10.1155/2012/649727. [PMID: 22619691]
  • Ashok Kumar, Mahendra Lal Tamta, Nisha Negi, K Chandrasekhar, Devendra Singh Negi. Phytochemical investigation and antifeedant activity of Premna latifolia leaves. Natural product research. 2011 Oct; 25(18):1680-6. doi: 10.1080/14786419.2010.511620. [PMID: 21756197]
  • Kaiwen Deng, Fuyuan He, Jilian Shi, Wenlong Liu, Huan Zou, Yun Qiu, Feng Chen. [Study on network compatibility of metabolisms in vivo rat for volatile oil in houttuyniae herba and 2-undecanone]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Aug; 36(15):2076-83. doi: . [PMID: 22066443]
  • Nikoletta G Ntalli, Francesca Manconi, Marco Leonti, Andrea Maxia, Pierluigi Caboni. Aliphatic ketones from Ruta chalepensis (Rutaceae) induce paralysis on root knot nematodes. Journal of agricultural and food chemistry. 2011 Jul; 59(13):7098-103. doi: 10.1021/jf2013474. [PMID: 21631118]
  • N W Kimps, B W Bissinger, C S Apperson, D E Sonenshine, R M Roe. First report of the repellency of 2-tridecanone against ticks. Medical and veterinary entomology. 2011 Jun; 25(2):202-8. doi: 10.1111/j.1365-2915.2010.00918.x. [PMID: 21073492]
  • Prisca S Pierre, Jeroen J Jansen, Cornelis A Hordijk, Nicole M van Dam, Anne-Marie Cortesero, Sébastien Dugravot. Differences in volatile profiles of turnip plants subjected to single and dual herbivory above- and belowground. Journal of chemical ecology. 2011 Apr; 37(4):368-77. doi: 10.1007/s10886-011-9934-3. [PMID: 21448706]
  • Alan J Grant, Joseph C Dickens. Functional characterization of the octenol receptor neuron on the maxillary palps of the yellow fever mosquito, Aedes aegypti. PloS one. 2011; 6(6):e21785. doi: 10.1371/journal.pone.0021785. [PMID: 21738794]
  • Wan Mohd Nuzul Hakimi Wan Salleh, Farediah Ahmad, Khong Heng Yen, Hasnah Mohd Sirat. Chemical compositions, antioxidant and antimicrobial activities of essential oils of Piper caninum Blume. International journal of molecular sciences. 2011; 12(11):7720-31. doi: 10.3390/ijms12117720. [PMID: 22174627]
  • Deepa Bisht, Chandan S Chanotiya. 2-undecanone rich leaf essential oil from Zanthoxylum armatum. Natural product communications. 2011 Jan; 6(1):111-4. doi: . [PMID: 21366058]
  • Geng Yu, Thuong T H Nguyen, Yongxia Guo, Ines Schauvinhold, Michele E Auldridge, Nazmul Bhuiyan, Imri Ben-Israel, Yoko Iijima, Eyal Fridman, Joseph P Noel, Eran Pichersky. Enzymatic functions of wild tomato methylketone synthases 1 and 2. Plant physiology. 2010 Sep; 154(1):67-77. doi: 10.1104/pp.110.157073. [PMID: 20605911]
  • Jonathan D Bohbot, Joseph C Dickens. Insect repellents: modulators of mosquito odorant receptor activity. PloS one. 2010 Aug; 5(8):e12138. doi: 10.1371/journal.pone.0012138. [PMID: 20725637]
  • Lixin Yang, Yongxin Zhang, Hong Yi, Hua Yang, Qiwei Zhang. [Determination of methyl nonyl ketone in volatile oil from herbs of Houttuynia cordata by GC-MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Aug; 35(15):1987-9. doi: 10.4268/cjcmm20101516. [PMID: 20931852]
  • K P Siju, Sharon R Hill, Bill S Hansson, Rickard Ignell. Influence of blood meal on the responsiveness of olfactory receptor neurons in antennal sensilla trichodea of the yellow fever mosquito, Aedes aegypti. Journal of insect physiology. 2010 Jun; 56(6):659-65. doi: 10.1016/j.jinsphys.2010.02.002. [PMID: 20153749]
  • Imri Ben-Israel, Geng Yu, Michael B Austin, Nazmul Bhuiyan, Michele Auldridge, Thuong Nguyen, Ines Schauvinhold, Joseph P Noel, Eran Pichersky, Eyal Fridman. Multiple biochemical and morphological factors underlie the production of methylketones in tomato trichomes. Plant physiology. 2009 Dec; 151(4):1952-64. doi: 10.1104/pp.109.146415. [PMID: 19801397]
  • N Kambouche, B Merah, S Bellahouel, J Bouayed, A Dicko, A Derdour, C Younos, R Soulimani. Chemical composition and antioxidant potential of Ruta montana L. essential oil from Algeria. Journal of medicinal food. 2008 Sep; 11(3):593-5. doi: 10.1089/jmf.2007.0515. [PMID: 18800912]
  • Bin Yang, Yong-Qing Xiao, Ri-Xin Liang, Ruo-Jing Wang, Wen Li, Cun Zhang, Ying Cao, Qian-Peng Wang, Lan Wang, Yong-Yan Wang. [Studies on expectorant compounds in volatile oil from root and rhizome of Aster tataricus]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Feb; 33(3):281-3. doi: ". [PMID: 18536466]
  • Amelia K Boehme, Joseph A Noletto, William A Haber, William N Setzer. Bioactivity and chemical composition of the leaf essential oils of Zanthoxylum rhoifolium and Zanthoxylum setulosum from Monteverde, Costa Rica. Natural product research. 2008 Jan; 22(1):31-6. doi: 10.1080/14786410601130224. [PMID: 17999336]
  • Xue-feng Xiao, Lan Gao, Yu Sun, Jun-ping Zhang, Xiao-li Qiao, Ya-peng Han. [Tissue distribution on methyl nonyl ketone of the volatile oil from Houttyunia cordata in mice]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Dec; 30(12):1558-60. doi: NULL. [PMID: 18422191]
  • Rui-yu Lin, Hao-sen Lin, Xiao-xia Sun, Zhong-yi Zhang, Chun-hua Peng, Zhen-fang Li, Hui Chen, Wen-xiong Lin. [Effects of fertilizer application on contents of 2-undecanone and soluble carbonhydrate in Houttuynia cordata with different fertilizers]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Nov; 32(22):2352-6. doi: ". [PMID: 18257256]
  • Jiang Meng, Xiao-ping Dong, Yi-sheng Zhou, Zhi-hong Jiang, Kelvin Sze-Yin Leung, Zhong-zhen Zhao. [Orthogonal experiment using SFE-CO2 in extraction of essential oil from fresh Houttuynia cordata and analysis of essential oil by GC-MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Feb; 32(3):215-7. doi: ". [PMID: 17432141]
  • Muhammad Ishtiaq Ch, Yang F Wen, YiYu Cheng. Gas chromatographic/mass spectrometric analysis of the essential oil of Houttuynia cordata Thunb by using on-column methylation with tetramethylammonium acetate. Journal of AOAC International. 2007 Jan; 90(1):60-7. doi: . [PMID: 17373437]
  • George F Antonious, John C Snyder. Natural products: repellency and toxicity of wild tomato leaf extracts to the two-spotted spider mite, Tetranychus urticae Koch. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2006; 41(1):43-55. doi: 10.1080/03601230500234893. [PMID: 16393894]
  • George F Antonious, Tejinder S Kochhar, Alvin M Simmons. Natural products: seasonal variation in trichome counts and contents in Lycopersicum hirsutum f. glabratum. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2005; 40(4):619-31. doi: 10.1081/pfc-200061567. [PMID: 16047884]
  • María Rosario Ramírez, Mario Estévez, David Morcuende, Ramón Cava. Effect of the type of frying culinary fat on volatile compounds isolated in fried pork loin chops by using SPME-GC-MS. Journal of agricultural and food chemistry. 2004 Dec; 52(25):7637-43. doi: 10.1021/jf049207s. [PMID: 15675815]
  • Santanu Bhattacharya, Padinjarae Vangasseri Dileep. Cationic oxyethylene lipids. Synthesis, aggregation, and transfection properties. Bioconjugate chemistry. 2004 May; 15(3):508-19. doi: 10.1021/bc0340215. [PMID: 15149178]
  • Wei Wu, You-liang Zheng, Yong Ma, Rui-wu Yang, Jin-xi Zhong, Fang-wei Ren, Tian-cheng Liu. [Analysis on yield and quality of different Houttuynia cordata]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2003 Aug; 28(8):718-20, 771. doi: ". [PMID: 15015349]
  • Vincenzo De Feo, Francesco De Simone, Felice Senatore. Potential allelochemicals from the essential oil of Ruta graveolens. Phytochemistry. 2002 Nov; 61(5):573-8. doi: 10.1016/s0031-9422(02)00284-4. [PMID: 12409025]
  • G F Antonious. Production and quantification of methyl ketones in wild tomato accessions. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2001 Nov; 36(6):835-48. doi: 10.1081/pfc-100107416. [PMID: 11757742]
  • K Hayashi, M Kamiya, T Hayashi. Virucidal effects of the steam distillate from Houttuynia cordata and its components on HSV-1, influenza virus, and HIV. Planta medica. 1995 Jun; 61(3):237-41. doi: 10.1055/s-2006-958063. [PMID: 7617766]