Acetophenone (BioDeep_00000000092)

 

Secondary id: BioDeep_00000860684

human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


Acetophenone, TraceCERT(R), certified reference material

化学式: C8H8O (120.0575118)
中文名称: 苯乙酮, 乙酰苯, 甲基苯基酮
谱图信息: 最多检出来源 Homo sapiens(feces) 0.03%

分子结构信息

SMILES: c1ccccc1C(=O)C
InChI: InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3

描述信息

Acetophenone appears as a colorless liquid with a sweet pungent taste and odor resembling the odor of oranges. Freezes under cool conditions. Slightly soluble in water and denser than water. Hence sinks in water. Vapor heavier than air. A mild irritant to skin and eyes. Vapors can be narcotic in high concentrations. Used as a flavoring, solvent, and polymerization catalyst.
Acetophenone is a methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group. It has a role as a photosensitizing agent, an animal metabolite and a xenobiotic.
Acetophenone is used for fragrance in soaps and perfumes, as a flavoring agent in foods, and as a solvent for plastics and resins. Acute (short-term) exposure to acetophenone vapor may produce skin irritation and transient corneal injury in humans. No information is available on the chronic (long-term), reproductive, developmental, or carcinogenic effects of acetophenone in humans. EPA has classified acetophenone as a Group D, not classifiable as to human carcinogenicity.
Acetophenone is a natural product found in Nepeta nepetella, Hypericum hyssopifolium, and other organisms with data available.
Acetophenone is a metabolite found in or produced by Saccharomyces cerevisiae.
Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances. Acetophenone is found in chicory. Acetophenone is a flavouring ingredient used in fruit flavours. Acetophenone is a raw material for the synthesis of some pharmaceuticals and is also listed as an approved excipient by the U.S. FDA. In a 1994 report released by five top cigarette companies in the U.S., acetophenone was listed as one of the 599 additives to cigarettes.
A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.
D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents
Flavouring ingredient used in fruit flavours; leavening agent
D003879 - Dermatologic Agents
Acetophenone is an organic compound with simple structure[1].
Acetophenone is an organic compound with simple structure[1].

同义名列表

67 个代谢物同义名

Acetophenone, TraceCERT(R), certified reference material; InChI=1/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H; Acetophenone, puriss. p.a., >=99.0\\% (GC); Acetophenone, ReagentPlus(R), 99\\%; Acetophenone, analytical standard; Ethanone-2,2,2-d3, 1-(phenyl-d5)-; Acetophenone, natural, 98\\%, FG; 1-Phenylethanone (acetophenone); Acetophenone, >=98.0\\% (GC); Acetophenone, >=98\\%, FG; (2,2,2,-2H3)ACETOPHENONE; Acetophenone-methyl-13C; Benzoyl methide hypnone; Acetophenone-alpha-13C; Ketone, methyl phenyl-; 1-Phenylethanone, 9CI; Acetophenone-1,2-13C2; Ketone, methyl phenyl; Phenyl methyl ketone; Methyl phenyl ketone; Methyl phenyl-Ketone; methyl-phenyl ketone; ACETOPHENONE [INCI]; 1-phenylethan-1-one; Ethanone, 1-phenyl-; ACETOPHENONE [FHFI]; ACETOPHENONE [HSDB]; 1-Phenyl-1-ethanone; methylphenylketone; ACETOPHENONE [FCC]; alpha-Acetophenone; phenylmethylketone; Acetofenon [Czech]; ACETOPHENONE [II]; ACETOPHENONE (II); ACETOPHENONE [MI]; 1-phenyl-ethanone; Ethanone,1-phenyl; Benzene, acetyl-; 1-Phenylethanone; Nchem.180-comp5; Benzoyl methide; Benzoylmethide; Phenylethanone; Acetyl-Benzene; acetyl-benzen; aceto-phenone; Acetylbenzene; aceto phenone; Tox21_300343; Acetylbenzol; Tox21_202422; Acetophenone; Acetophenon; Acetofenona; CAS-98-86-2; Acetofenon; FEMA 2009; AI3-00575; WLN: 1VR; Hypnone; Hypnon; Phenyl; Dymex; AC0; Acetophenone; Acetophenone



数据库引用编号

25 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

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

175 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

  • Suphasit Nathabumroong, Awat Wisetsai, Ratsami Lekphrom, Thanapat Suebrasri, Florian T Schevenels. A new polyphenolic isoprenylated acetophenone dimer from the stem bark of Acronychia pedunculata (L.) Miq. Natural product research. 2023 Apr; 37(7):1098-1105. doi: 10.1080/14786419.2021.1989680. [PMID: 34632889]
  • Kaicheng Du, Zhiqi Zhang, Di Jing, Yumeng Wang, Xingyao Li, Dali Meng. Diterpene glycosides, acetophenone glycosides and tannins from polar extracts of the root of Euphorbia fischeriana with cytotoxicity and antibacterial activities. Phytochemistry. 2022 Nov; 203(?):113382. doi: 10.1016/j.phytochem.2022.113382. [PMID: 36007663]
  • Gara N Dexter, Laura E Navas, Jason C Grigg, Harbir Bajwa, David J Levy-Booth, Jie Liu, Nathan A Louie, Seyed A Nasseri, Soo-Kyeong Jang, Scott Renneckar, Lindsay D Eltis, William W Mohn. Bacterial catabolism of acetovanillone, a lignin-derived compound. Proceedings of the National Academy of Sciences of the United States of America. 2022 10; 119(43):e2213450119. doi: 10.1073/pnas.2213450119. [PMID: 36256818]
  • Saki Oya, Satoshi Tonegawa, Hirari Nakagawa, Hiroshi Habe, Toshiki Furuya. Isolation and characterization of microorganisms capable of cleaving the ether bond of 2-phenoxyacetophenone. Scientific reports. 2022 02; 12(1):2874. doi: 10.1038/s41598-022-06816-1. [PMID: 35190591]
  • Chun-Hao Chang, Semon Wu, Kai-Cheng Hsu, Wei-Jan Huang, Jih-Jung Chen. Dibenzofuran, 4-Chromanone, Acetophenone, and Dithiecine Derivatives: Cytotoxic Constituents from Eupatorium fortunei. International journal of molecular sciences. 2021 Jul; 22(14):. doi: 10.3390/ijms22147448. [PMID: 34299072]
  • Ratih Dewi Saputri, Tjitjik Srie Tjahjandarie, Mulyadi Tanjung. Two novel coumarins bearing an acetophenone derivative from the leaves of Melicope Quercifolia. Natural product research. 2021 Apr; 35(8):1256-1261. doi: 10.1080/14786419.2019.1644634. [PMID: 31328970]
  • Fernanda Severo Sabedra Sousa, Paloma Taborda Birmann, Renata Balaguez, Diego Alves, César Augusto Brüning, Lucielli Savegnago. α-(phenylselanyl) acetophenone abolishes acute restraint stress induced-comorbid pain, depression and anxiety-related behaviors in mice. Neurochemistry international. 2018 11; 120(?):112-120. doi: 10.1016/j.neuint.2018.08.006. [PMID: 30114472]
  • Mebarek Lamara, Geneviève J Parent, Isabelle Giguère, Jean Beaulieu, Jean Bousquet, John J MacKay. Association genetics of acetophenone defence against spruce budworm in mature white spruce. BMC plant biology. 2018 Oct; 18(1):231. doi: 10.1186/s12870-018-1434-y. [PMID: 30309315]
  • Wen-Jia Dan, Thi-Mai-Luong Tuong, Da-Cheng Wang, Ding Li, An-Ling Zhang, Jin-Ming Gao. Natural products as sources of new fungicides (V): Design and synthesis of acetophenone derivatives against phytopathogenic fungi in vitro and in vivo. Bioorganic & medicinal chemistry letters. 2018 09; 28(17):2861-2864. doi: 10.1016/j.bmcl.2018.07.031. [PMID: 30037493]
  • Anhua Wang, Xiaoxv Gao, Xiaokui Huo, Shanshan Huang, Lei Feng, Chengpeng Sun, Baojing Zhang, Xiaochi Ma, Jingming Jia, Chao Wang. Antioxidant acetophenone glycosides from the roots of Euphorbia ebracteolata Hayata. Natural product research. 2018 Sep; 32(18):2187-2192. doi: 10.1080/14786419.2017.1371160. [PMID: 28856938]
  • José Tiago Moreira, Tiago M Moreira, João B Cunha, Manuel Azenha, Fernanda Fidalgo, Jorge Teixeira. Differential effects of acetophenone on shoots' and roots' metabolism of Solanum nigrum L. plants and implications in its phytoremediation. Plant physiology and biochemistry : PPB. 2018 Sep; 130(?):391-398. doi: 10.1016/j.plaphy.2018.07.027. [PMID: 30064095]
  • Ying Zhou, Qiyuan Peng, Lanting Zeng, Jinchi Tang, Jianlong Li, Fang Dong, Ziyin Yang. Study of the biochemical formation pathway of aroma compound 1-phenylethanol in tea (Camellia sinensis (L.) O. Kuntze) flowers and other plants. Food chemistry. 2018 Aug; 258(?):352-358. doi: 10.1016/j.foodchem.2018.03.095. [PMID: 29655745]
  • Neng-Hua Chen, Wen Li, Yuan-Lin Zhong, Qian-Wen Niu, Ying-Ying Li, Yu-Bo Zhang, Man-Mei Li, Yao-Lan Li, Guo-Cai Wang. New Acetophenone Derivatives from Acronychia oligophlebia and Their Anti-inflammatory and Antioxidant Activities. Chemistry & biodiversity. 2018 May; 15(5):e18000080. doi: 10.1002/cbdv.201800080. [PMID: 29624846]
  • Melissa H Mageroy, Sharon Jancsik, Macaire Man Saint Yuen, Michael Fischer, Stephen G Withers, Christian Paetz, Bernd Schneider, John Mackay, Joerg Bohlmann. A Conifer UDP-Sugar Dependent Glycosyltransferase Contributes to Acetophenone Metabolism and Defense against Insects. Plant physiology. 2017 Oct; 175(2):641-651. doi: 10.1104/pp.17.00611. [PMID: 28794260]
  • Courtney Marneweck, Andreas Jürgens, Adrian M Shrader. Temporal Variation of White Rhino Dung Odours. Journal of chemical ecology. 2017 Oct; 43(10):955-965. doi: 10.1007/s10886-017-0890-4. [PMID: 28983753]
  • Serena Fraraccio, Michal Strejcek, Iva Dolinova, Tomas Macek, Ondrej Uhlik. Secondary compound hypothesis revisited: Selected plant secondary metabolites promote bacterial degradation of cis-1,2-dichloroethylene (cDCE). Scientific reports. 2017 08; 7(1):8406. doi: 10.1038/s41598-017-07760-1. [PMID: 28814712]
  • Faheem Uddin Rajer, Huijun Wu, Yongli Xie, Shanshan Xie, Waseem Raza, Hafiz Abdul Samad Tahir, Xuewen Gao. Volatile organic compounds produced by a soil-isolate, Bacillus subtilis FA26 induce adverse ultra-structural changes to the cells of Clavibacter michiganensis ssp. sepedonicus, the causal agent of bacterial ring rot of potato. Microbiology (Reading, England). 2017 04; 163(4):523-530. doi: 10.1099/mic.0.000451. [PMID: 28418289]
  • Fang Dong, Ying Zhou, Lanting Zeng, Naoharu Watanabe, Xinguo Su, Ziyin Yang. Optimization of the Production of 1-Phenylethanol Using Enzymes from Flowers of Tea (Camellia sinensis) Plants. Molecules (Basel, Switzerland). 2017 Jan; 22(1):. doi: 10.3390/molecules22010131. [PMID: 28098803]
  • Ken-Ichi Nakashima, Naohito Abe, Fang-Rong Chang, Makoto Inoue, Masayoshi Oyama. Pteleifolols A-E, acetophenone di-C-glycosides and a benzopyran dimer from the leaves of Melicope pteleifolia. Journal of natural medicines. 2017 Jan; 71(1):299-304. doi: 10.1007/s11418-016-1035-8. [PMID: 27600933]
  • Sang Mi Lee, Jieun Oh, Byung-Serk Hurh, Gwi-Hwa Jeong, Young-Keum Shin, Young-Suk Kim. Volatile Compounds Produced by Lactobacillus paracasei During Oat Fermentation. Journal of food science. 2016 Dec; 81(12):C2915-C2922. doi: 10.1111/1750-3841.13547. [PMID: 27925257]
  • Eduarda M P Silva, Tânia Melo, Bebiana C Sousa, Diana I S P Resende, Luís M Magalhães, Marcela A Segundo, Artur M S Silva, M Rosário M Domingues. Do cinnamylideneacetophenones have antioxidant properties and a protective effect toward the oxidation of phosphatidylcholines?. European journal of medicinal chemistry. 2016 Oct; 121(?):331-337. doi: 10.1016/j.ejmech.2016.05.040. [PMID: 27267003]
  • Ngoc Hieu Nguyen, Thi Kim Quy Ha, Sangho Choi, Sangmi Eum, Chul Ho Lee, Tran The Bach, Vu Tien Chinh, Won Keun Oh. Chemical constituents from Melicope pteleifolia leaves. Phytochemistry. 2016 Oct; 130(?):291-300. doi: 10.1016/j.phytochem.2016.06.011. [PMID: 27374481]
  • Guo-Ru Shi, Xin Wang, Yan-Fei Liu, Chun-Lei Zhang, Yan Wang, Li Li, Gang Ni, Ruo-Yun Chen, De-Quan Yu. Aromatic glycosides from the whole plants of Iris japonica. Journal of Asian natural products research. 2016 Oct; 18(10):921-7. doi: 10.1080/10286020.2016.1188807. [PMID: 27310650]
  • Fang Dong, Ying Zhou, Lanting Zeng, Qiyuan Peng, Yiyong Chen, Ling Zhang, Xinguo Su, Naoharu Watanabe, Ziyin Yang. Elucidation of Differential Accumulation of 1-Phenylethanol in Flowers and Leaves of Tea (Camellia sinensis) Plants. Molecules (Basel, Switzerland). 2016 Aug; 21(9):. doi: 10.3390/molecules21091106. [PMID: 27563859]
  • Minoru Koura, Yuki Yamaguchi, Sayaka Kurobuchi, Hisashi Sumida, Yuichiro Watanabe, Takashi Enomoto, Takayuki Matsuda, Ayumu Okuda, Tomoaki Koshizawa, Yuki Matsumoto, Kimiyuki Shibuya. Discovery of a 2-hydroxyacetophenone derivative as an outstanding linker to enhance potency and β-selectivity of liver X receptor agonist. Bioorganic & medicinal chemistry. 2016 08; 24(16):3436-46. doi: 10.1016/j.bmc.2016.05.048. [PMID: 27283790]
  • Xian Yang, Yu-Bo Zhang, Zhong-Nan Wu, Xiang-Qiang Zhang, Jian-Wei Jiang, Yao-Lan Li, Guo-Cai Wang. Six new prenylated acetophenone derivatives from the leaves of Acronychia oligophlebia. Fitoterapia. 2015 Sep; 105(?):156-9. doi: 10.1016/j.fitote.2015.07.002. [PMID: 26160157]
  • M Azmatunnisa, K Rahul, K V N S Lakshmi, Ch Sasikala, Ch V Ramana. Lysinibacillus acetophenoni sp. nov., a solvent-tolerant bacterium isolated from acetophenone. International journal of systematic and evolutionary microbiology. 2015 Jun; 65(Pt 6):1741-1748. doi: 10.1099/ijs.0.000170. [PMID: 25740932]
  • Eirini Kouloura, Alexios-Leandros Skaltsounis, Sylvie Michel, Maria Halabalaki. Ion tree-based structure elucidation of acetophenone dimers (AtA) from Acronychia pedunculata and their identification in extracts by liquid chromatography electrospray ionization LTQ-Orbitrap mass spectrometry. Journal of mass spectrometry : JMS. 2015 Mar; 50(3):495-512. doi: 10.1002/jms.3556. [PMID: 25800186]
  • Melissa H Mageroy, Geneviève Parent, Gaby Germanos, Isabelle Giguère, Nathalie Delvas, Halim Maaroufi, Éric Bauce, Joerg Bohlmann, John J Mackay. Expression of the β-glucosidase gene Pgβglu-1 underpins natural resistance of white spruce against spruce budworm. The Plant journal : for cell and molecular biology. 2015 Jan; 81(1):68-80. doi: 10.1111/tpj.12699. [PMID: 25302566]
  • Hirozumi Toyama, Masaharu Nakamura, Masahiko Nakamura, Yotaro Matsumoto, Madoka Nakagomi, Yuichi Hashimoto. Development of novel silicon-containing inverse agonists of retinoic acid receptor-related orphan receptors. Bioorganic & medicinal chemistry. 2014 Mar; 22(6):1948-59. doi: 10.1016/j.bmc.2014.01.023. [PMID: 24559867]
  • Yuka Inatomi, Hiroko Murata, Akira Inada, Tsutomu Nakanishi, Frank A Lang, Jin Murata, Munekazu Iinuma. New glycosides of acetophenone derivatives and phenylpropanoids from Juniperus occidentalis. Journal of natural medicines. 2013 Apr; 67(2):359-68. doi: 10.1007/s11418-012-0694-3. [PMID: 22847379]
  • Wei Li, Li-Chun Zhao, Yin-Shi Sun, Feng-Jie Lei, Zi Wang, Xiong-Bin Gui, Hui Wang. Optimization of pressurized liquid extraction of three major acetophenones from Cynanchum bungei using a box-behnken design. International journal of molecular sciences. 2012 Nov; 13(11):14533-44. doi: 10.3390/ijms131114533. [PMID: 23203079]
  • Hee-Kwon Kim, Jeroen Van den Bossche, Seok-Hee Hyun, David H Thompson. Acid-triggered release via dePEGylation of fusogenic liposomes mediated by heterobifunctional phenyl-substituted vinyl ethers with tunable pH-sensitivity. Bioconjugate chemistry. 2012 Oct; 23(10):2071-7. doi: 10.1021/bc300266y. [PMID: 22988941]
  • Elizabeth S Chipps, Renuka Jayini, Shoko Ando, April D Protzman, M Zubayed Muhi, M Abdul Mottaleb, Ahmed Malkawi, M Rafiq Islam. Cytotoxicity analysis of active components in bitter melon (Momordica charantia) seed extracts using human embryonic kidney and colon tumor cells. Natural product communications. 2012 Sep; 7(9):1203-8. doi: NULL. [PMID: 23074909]
  • John J Beck, Bradley S Higbee, Douglas M Light, Wai S Gee, Glory B Merrill, Jennifer M Hayashi. Hull split and damaged almond volatiles attract male and female navel orangeworm moths. Journal of agricultural and food chemistry. 2012 Aug; 60(33):8090-6. doi: 10.1021/jf302658v. [PMID: 22849631]
  • Eirini Kouloura, Maria Halabalaki, Marie-Christine Lallemand, Sangkil Nam, Richard Jove, Marc Litaudon, Khalijah Awang, Hamid A Hadi, Alexios-Leandros Skaltsounis. Cytotoxic prenylated acetophenone dimers from Acronychia pedunculata. Journal of natural products. 2012 Jul; 75(7):1270-6. doi: 10.1021/np201007a. [PMID: 22708987]
  • Saowanee Chaipech, Toshio Morikawa, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka. New flav-3-en-3-ol glycosides, kaempferiaosides C and D, and acetophenone glycosides, kaempferiaosides E and F, from the rhizomes of Kaempferia parviflora. Journal of natural medicines. 2012 Jul; 66(3):486-92. doi: 10.1007/s11418-011-0611-1. [PMID: 22101441]
  • Ahmed M Saveer, Sophie H Kromann, Göran Birgersson, Marie Bengtsson, Tobias Lindblom, Anna Balkenius, Bill S Hansson, Peter Witzgall, Paul G Becher, Rickard Ignell. Floral to green: mating switches moth olfactory coding and preference. Proceedings. Biological sciences. 2012 Jun; 279(1737):2314-22. doi: 10.1098/rspb.2011.2710. [PMID: 22319127]
  • Zhong-Hua Yang, Li Luo, Xu Chang, Wei Zhou, Geng-Hua Chen, Yan Zhao, Ya-Jun Wang. Production of chiral alcohols from prochiral ketones by microalgal photo-biocatalytic asymmetric reduction reaction. Journal of industrial microbiology & biotechnology. 2012 Jun; 39(6):835-41. doi: 10.1007/s10295-012-1088-y. [PMID: 22322691]
  • John J Beck, Douglas M Light, Wai S Gee. Electroantennographic bioassay as a screening tool for host plant volatiles. Journal of visualized experiments : JoVE. 2012 May; ?(63):e3931. doi: 10.3791/3931. [PMID: 22588282]
  • Rongcai Yue, Xing Yuan, Xiaojun Liu, Jigang Zhang, Peng Jiang, Cheng He, Lei Shan, Yizhi Yu, Weidong Zhang. Cynandione A mitigates ischemic injuries in rats with cerebral ischemia. Journal of neurochemistry. 2012 May; 121(3):451-64. doi: 10.1111/j.1471-4159.2012.07682.x. [PMID: 22309483]
  • Liang Zhu, Si-ming Zhu, Ying-juan Tian. Antioxidant and antimicrobial activities of essential oil and extracts of Saurauia lantsangensis hu root. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2012 May; 67(5-6):282-90. doi: 10.1515/znc-2012-5-607. [PMID: 22888533]
  • Min Seok Oh, Ji-Yeon Yang, Hoi Seon Lee. Acaricidal toxicity of 2'-hydroxy-4'-methylacetophenone isolated from Angelicae koreana roots and structure-activity relationships of its derivatives. Journal of agricultural and food chemistry. 2012 Apr; 60(14):3606-11. doi: 10.1021/jf205379u. [PMID: 22429095]
  • Vikas Srivastava, Arvind Singh Negi, P V Ajayakumar, Shamshad A Khan, Suchitra Banerjee. Atropa belladonna hairy roots: orchestration of concurrent oxidation and reduction reactions for biotransformation of carbonyl compounds. Applied biochemistry and biotechnology. 2012 Mar; 166(6):1401-8. doi: 10.1007/s12010-011-9533-3. [PMID: 22246731]
  • Yosuke Hanai, Ken Shimono, Hiroaki Oka, Yoshinobu Baba, Kunio Yamazaki, Gary K Beauchamp. Analysis of volatile organic compounds released from human lung cancer cells and from the urine of tumor-bearing mice. Cancer cell international. 2012 Feb; 12(1):7. doi: 10.1186/1475-2867-12-7. [PMID: 22364569]
  • Fang Dong, Ziyin Yang, Susanne Baldermann, Yutaka Kajitani, Shogo Ota, Hisae Kasuga, Yumi Imazeki, Toshiyuki Ohnishi, Naoharu Watanabe. Characterization of L-phenylalanine metabolism to acetophenone and 1-phenylethanol in the flowers of Camellia sinensis using stable isotope labeling. Journal of plant physiology. 2012 Feb; 169(3):217-25. doi: 10.1016/j.jplph.2011.12.003. [PMID: 22209218]
  • Michaela Kolb, Volker Sieber, Manfred Amann, Martin Faulstich, Doris Schieder. Removal of monomer delignification products by laccase from Trametes versicolor. Bioresource technology. 2012 Jan; 104(?):298-304. doi: 10.1016/j.biortech.2011.11.080. [PMID: 22176974]
  • Semih Otles, Buket Yalcin. Phenolic compounds analysis of root, stalk, and leaves of nettle. TheScientificWorldJournal. 2012; 2012(?):564367. doi: 10.1100/2012/564367. [PMID: 22593694]
  • Maria Graça Miguel, Maria Dulce Antunes. Is propolis safe as an alternative medicine?. Journal of pharmacy & bioallied sciences. 2011 Oct; 3(4):479-95. doi: 10.4103/0975-7406.90101. [PMID: 22219581]
  • Purabi Roy, Sarika Amdekar, Avnish Kumar, Vinod Singh. Preliminary study of the antioxidant properties of flowers and roots of Pyrostegia venusta (Ker Gawl) Miers. BMC complementary and alternative medicine. 2011 Aug; 11(?):69. doi: 10.1186/1472-6882-11-69. [PMID: 21861910]
  • Hae Jin Kim, Sung Han Ok, Sung Chul Bahn, Juno Jang, Sung Aeong Oh, Soon Ki Park, David Twell, Stephen Beungtae Ryu, Jeong Sheop Shin. Endoplasmic reticulum- and Golgi-localized phospholipase A2 plays critical roles in Arabidopsis pollen development and germination. The Plant cell. 2011 Jan; 23(1):94-110. doi: 10.1105/tpc.110.074799. [PMID: 21278126]
  • Le-Le Hu, Chen Chen, Tao Huang, Yu-Dong Cai, Kuo-Chen Chou. Predicting biological functions of compounds based on chemical-chemical interactions. PloS one. 2011; 6(12):e29491. doi: 10.1371/journal.pone.0029491. [PMID: 22220213]
  • Zachary L Fowler, Karan Shah, John C Panepinto, Amy Jacobs, Mattheos A G Koffas. Development of non-natural flavanones as antimicrobial agents. PloS one. 2011; 6(10):e25681. doi: 10.1371/journal.pone.0025681. [PMID: 22039419]
  • Peng He, Jin Zhang, Nai-Yong Liu, Ya-Nan Zhang, Ke Yang, Shuang-Lin Dong. Distinct expression profiles and different functions of odorant binding proteins in Nilaparvata lugens Stål. PloS one. 2011; 6(12):e28921. doi: 10.1371/journal.pone.0028921. [PMID: 22174925]
  • Christy E Manyi-Loh, Roland N Ndip, Anna M Clarke. Volatile compounds in honey: a review on their involvement in aroma, botanical origin determination and potential biomedical activities. International journal of molecular sciences. 2011; 12(12):9514-32. doi: 10.3390/ijms12129514. [PMID: 22272147]
  • Ying Wang, Guoping Wang, Liwei Wang, Xuhui Xu, Jing Xia, Xuefang Huang, Yougui Wu, Chulong Zhang. [Isolation and identification of an endophytic fungus of Polygonatum cyrtonema and its antifungal metabolites]. Wei sheng wu xue bao = Acta microbiologica Sinica. 2010 Aug; 50(8):1036-43. doi: ". [PMID: 20931871]
  • Braulio Insuasty, Alexis Tigreros, Fabián Orozco, Jairo Quiroga, Rodrigo Abonía, Manuel Nogueras, Adolfo Sanchez, Justo Cobo. Synthesis of novel pyrazolic analogues of chalcones and their 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents. Bioorganic & medicinal chemistry. 2010 Jul; 18(14):4965-74. doi: 10.1016/j.bmc.2010.06.013. [PMID: 20594863]
  • Wafaa Benalla, Saïd Bellahcen, Mohamed Bnouham. Antidiabetic medicinal plants as a source of alpha glucosidase inhibitors. Current diabetes reviews. 2010 Jul; 6(4):247-54. doi: 10.2174/157339910791658826. [PMID: 20522017]
  • Ning Zhang, Hao Cai, BaoChang Cai, HaiJun Yang, JunSong Li, GuangMing Yang. Two new cytotoxic acetophenone derivatives from Euphorbia ebracteolata Hayata. Fitoterapia. 2010 Jul; 81(5):385-8. doi: 10.1016/j.fitote.2009.11.007. [PMID: 19958822]
  • Eduardo Antonio Ferreira, Eliana Fortes Gris, Karina Bettega Felipe, João Francisco Gomes Correia, Eduardo Cargnin-Ferreira, Danilo Wilhelm Filho, Rozangela Curi Pedrosa. Potent hepatoprotective effect in CCl(4)-induced hepatic injury in mice of phloroacetophenone from Myrcia multiflora. The Libyan journal of medicine. 2010 Jun; 5(?):. doi: 10.3402/ljm.v5i0.4891. [PMID: 21483585]
  • Hai-Li Liu, Xiao-Yin Huang, Mei-Ling Dong, Guo-Rong Xin, Yue-Wei Guo. Piperidine alkaloids from Chinese mangrove Sonneratia hainanensis. Planta medica. 2010 Jun; 76(9):920-2. doi: 10.1055/s-0029-1240811. [PMID: 20108179]
  • Harikishore Pingali, Mukul Jain, Shailesh Shah, Pandurang Zaware, Pankaj Makadia, Suresh Pola, Baban Thube, Darshit Patel, Pravin Patil, Priyanka Priyadarshini, Dinesh Suthar, Maanan Shah, Suresh Giri, Pankaj Patel. Design and synthesis of novel bis-oximinoalkanoic acids as potent PPAR alpha agonists. Bioorganic & medicinal chemistry letters. 2010 Feb; 20(3):1156-61. doi: 10.1016/j.bmcl.2009.12.022. [PMID: 20022492]
  • Koichi Matsumura, Maryanne Opiekun, Hiroaki Oka, Anil Vachani, Steven M Albelda, Kunio Yamazaki, Gary K Beauchamp. Urinary volatile compounds as biomarkers for lung cancer: a proof of principle study using odor signatures in mouse models of lung cancer. PloS one. 2010 Jan; 5(1):e8819. doi: 10.1371/journal.pone.0008819. [PMID: 20111698]
  • Takashi Yoshida, Yoshiaki Amakura, Morio Yoshimura. Structural features and biological properties of ellagitannins in some plant families of the order Myrtales. International journal of molecular sciences. 2010 Jan; 11(1):79-106. doi: 10.3390/ijms11010079. [PMID: 20162003]
  • Jun-ya Ueda, Motoki Takagi, Kazuo Shin-ya. Aminocaprophenone- and pyrrolidine-type alkaloids from the leaves of Ficus septica. Journal of natural products. 2009 Dec; 72(12):2181-3. doi: 10.1021/np900580f. [PMID: 19938815]
  • M Shahar Yar, M Mustaqeem Abdullah, A Husain, M Afroz Bhakht, Erik De Clercq. Synthesis and evaluation of in vitro antiviral activity of 2-[3-(substituted phenyl)-4,5-dihydro-1H-5-pyrazolyl]benzofuran-3-yl chloride derivatives. Journal of enzyme inhibition and medicinal chemistry. 2009 Aug; 24(4):949-56. doi: 10.1080/14756360802560677. [PMID: 19555169]
  • Christian Abel, Maria Clauss, Andrea Schaub, Jonathan Gershenzon, Dorothea Tholl. Floral and insect-induced volatile formation in Arabidopsis lyrata ssp. petraea, a perennial, outcrossing relative of A. thaliana. Planta. 2009 Jun; 230(1):1-11. doi: 10.1007/s00425-009-0921-7. [PMID: 19322583]
  • Zhong-Hua Yang, Rong Zeng, Gai Yang, Yu Wang, Li-Zhen Li, Zao-Sheng Lv, Man Yao, Bin Lai. Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue. Journal of industrial microbiology & biotechnology. 2008 Sep; 35(9):1047-51. doi: 10.1007/s10295-008-0381-2. [PMID: 18548304]
  • Junheon Kim, Sun-Mi Seo, Sang-Gil Lee, Sang-Chul Shin, Il-Kwon Park. Nematicidal activity of plant essential oils and components from coriander (Coriandrum sativum), Oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii) essential oils against pine wood nematode (Bursaphelenchus xylophilus). Journal of agricultural and food chemistry. 2008 Aug; 56(16):7316-20. doi: 10.1021/jf800780f. [PMID: 18605734]
  • Jan Rezek, Tomas Macek, Martina Mackova, Jan Triska, Kamila Ruzickova. Hydroxy-PCBs, methoxy-PCBs and hydroxy-methoxy-PCBs: metabolites of polychlorinated biphenyls formed in vitro by tobacco cells. Environmental science & technology. 2008 Aug; 42(15):5746-51. doi: 10.1021/es800445h. [PMID: 18754503]
  • Omar Gustafsson, Klaus B Mogensen, Jörg P Kutter. Underivatized cyclic olefin copolymer as substrate material and stationary phase for capillary and microchip electrochromatography. Electrophoresis. 2008 Aug; 29(15):3145-52. doi: 10.1002/elps.200800131. [PMID: 18618461]
  • M Arvand, S A Asadollahzadeh. Ion-selective electrode for aluminum determination in pharmaceutical substances, tea leaves and water samples. Talanta. 2008 May; 75(4):1046-54. doi: 10.1016/j.talanta.2008.01.001. [PMID: 18585182]
  • Cameron C Murphy, Eric J Murphy, Mikhail Y Golovko. Erucic acid is differentially taken up and metabolized in rat liver and heart. Lipids. 2008 May; 43(5):391-400. doi: 10.1007/s11745-008-3168-3. [PMID: 18350328]
  • Ken-ichi Itoh, Kaoru Nakamura, Takamitsu Utsukihara, Hiroshi Sakamaki, C Akira Horiuchi. Stereoselective oxidation of racemic 1-arylethanols by basil cultured cells of Ocimum basilicum cv. Purpurascens. Biotechnology letters. 2008 May; 30(5):951-4. doi: 10.1007/s10529-007-9615-z. [PMID: 18060603]
  • J Stefanska, R Pawliczak. Apocynin: molecular aptitudes. Mediators of inflammation. 2008; 2008(?):106507. doi: 10.1155/2008/106507. [PMID: 19096513]
  • M A Zanjanchi, M Arvand, A Islamnezhad, N O Mahmoodi. Novel potentiometric membrane sensor based on 6-(4-nitrophenyl)-2-phenyl-4,4-dipropyl-3,5-diaza-bicyclo[3,1,0] hex-2-ene for detection of strontium (II) ions at trace levels. Talanta. 2007 Nov; 74(1):125-31. doi: 10.1016/j.talanta.2007.05.034. [PMID: 18371621]
  • W A Jonfia-Essien, P G Alderson, G Tucker, R Linforth, G West. Behavioural responses of Tribolium castaneum (Herbst) to volatiles identified from dry cocoa beans. Pakistan journal of biological sciences : PJBS. 2007 Oct; 10(20):3549-56. doi: 10.3923/pjbs.2007.3549.3556. [PMID: 19093461]
  • Eleftherios Alissandrakis, Petros A Tarantilis, Paschalis C Harizanis, Moschos Polissiou. Comparison of the volatile composition in thyme honeys from several origins in Greece. Journal of agricultural and food chemistry. 2007 Oct; 55(20):8152-7. doi: 10.1021/jf071442y. [PMID: 17824662]
  • Cristina F Bush, Seth V Jones, Alicia N Lyle, Kenneth P Minneman, Kerry J Ressler, Randy A Hall. Specificity of olfactory receptor interactions with other G protein-coupled receptors. The Journal of biological chemistry. 2007 Jun; 282(26):19042-51. doi: 10.1074/jbc.m610781200. [PMID: 17472961]
  • Hui-Lin Yu, Yong-Jun Zhang, Wen-Liang Pan, Yu-Yuan Guo, Xi-Wu Gao. [Identification of volatiles from field cotton plant under different induction treatments]. Ying yong sheng tai xue bao = The journal of applied ecology. 2007 Apr; 18(4):859-64. doi: ". [PMID: 17615885]
  • John M Keith, Leslie A Gomez, Michael A Letavic, Kiev S Ly, Jill A Jablonowski, Mark Seierstad, Ann J Barbier, Sandy J Wilson, Jamin D Boggs, Ian C Fraser, Curt Mazur, Timothy W Lovenberg, Nicholas I Carruthers. Dual serotonin transporter/histamine H3 ligands: Optimization of the H3 pharmacophore. Bioorganic & medicinal chemistry letters. 2007 Feb; 17(3):702-6. doi: 10.1016/j.bmcl.2006.10.089. [PMID: 17107798]
  • M A Birkett, K Chamberlain, Z R Khan, J A Pickett, T Toshova, L J Wadhams, C M Woodcock. Electrophysiological responses of the lepidopterous stemborers Chilo partellus and Busseola fusca to volatiles from wild and cultivated host plants. Journal of chemical ecology. 2006 Nov; 32(11):2475-87. doi: 10.1007/s10886-006-9165-1. [PMID: 17080306]
  • Khozirah Shaari, Suryati Safri, Faridah Abas, Nordin Hj Lajis, D A Israf. A geranylacetophenone from the leaves of Melicope ptelefolia. Natural product research. 2006 May; 20(5):415-9. doi: 10.1080/14786410500045655. [PMID: 16644538]
  • Hsueh-Chun Chou, Jih-Jung Chen, Chang-Yih Duh, Tur-Fu Huang, Ih-Sheng Chen. Cytotoxic and anti-platelet aggregation constituents from the root wood of Melicope semecarpifolia. Planta medica. 2005 Nov; 71(11):1078-81. doi: 10.1055/s-2005-871295. [PMID: 16320216]
  • Angelika Lendl, Ingrid Werner, Sabine Glasl, Christa Kletter, Pavel Mucaji, Armin Presser, Gottfried Reznicek, Johann Jurenitsch, David W Taylor. Phenolic and terpenoid compounds from Chione venosa (sw.) urban var. venosa (Bois Bandé). Phytochemistry. 2005 Oct; 66(19):2381-7. doi: 10.1016/j.phytochem.2005.07.002. [PMID: 16140348]
  • Zhi-Qi Yin, Chun-Lin Fan, Wen-Cai Ye, Ren-Wang Jiang, Chun-Tao Che, Thomas C Mak, Shou-Xun Zhao, Xin-Sheng Yao. Acetophenone derivatives and sesquiterpene from Euphorbia ebracteolata. Planta medica. 2005 Oct; 71(10):979-82. doi: 10.1055/s-2005-871301. [PMID: 16254837]
  • David T Moore, Jos Oomens, John R Eyler, Gert von Helden, Gerard Meijer, Robert C Dunbar. Infrared spectroscopy of gas-phase Cr+ coordination complexes: determination of binding sites and electronic states. Journal of the American Chemical Society. 2005 May; 127(19):7243-54. doi: 10.1021/ja042431d. [PMID: 15884966]
  • Dave Caron, Andrew P Coughlan, Mathieu Simard, Jonathan Bernier, Yves Piché, Robert Chênevert. Stereoselective reduction of ketones by Daucus carota hairy root cultures. Biotechnology letters. 2005 May; 27(10):713-6. doi: 10.1007/s10529-005-5187-y. [PMID: 16049739]
  • R Ranau, K K Kleeberg, M Schlegelmilch, J Streese, R Stegmann, H Steinhart. Analytical determination of the suitability of different processes for the treatment of odorous waste gas. Waste management (New York, N.Y.). 2005; 25(9):908-16. doi: 10.1016/j.wasman.2005.07.004. [PMID: 16140002]
  • Taha Rababah, Navam Hettiarachchy, Ronny Horax, Satchithanandam Eswaranandam, Andronikos Mauromoustakos, James Dickson, Steven Niebuhr. Effect of electron beam irradiation and storage at 5 degrees C on thiobarbituric acid reactive substances and carbonyl contents in chicken breast meat infused with antioxidants and selected plant extracts. Journal of agricultural and food chemistry. 2004 Dec; 52(26):8236-41. doi: 10.1021/jf049147q. [PMID: 15612823]
  • Henrik Toft Simonsen, Anne Adsersen, Paul Bremner, Michael Heinrich, Ulla Wagner Smitt, Jerzy W Jaroszewski. Antifungal constituents of Melicope borbonica. Phytotherapy research : PTR. 2004 Jul; 18(7):542-5. doi: 10.1002/ptr.1482. [PMID: 15305313]
  • Zulfiqar Ali, Tetsuro Ito, Toshiyuki Tanaka, Ken-ichi Nakaya, Jin Murata, Dedy Darnaedi, Munekazu Iinuma. Acetophenone C-glucosides and stilbene O-glucosides in Upuna borneensis. Phytochemistry. 2004 Jul; 65(14):2141-6. doi: 10.1016/j.phytochem.2004.06.013. [PMID: 15279986]
  • César A N Catalán, Carola S de Heluani, Claudia Kotowicz, Thomas E Gedris, Werner Herz. A linear sesterterpene, two squalene derivatives and two peptide derivatives from Croton hieronymi. Phytochemistry. 2003 Sep; 64(2):625-9. doi: 10.1016/s0031-9422(03)00202-4. [PMID: 12943786]
  • Chung-Ren Su, Ping-Chung Kuo, Meei-Ling Wang, Meei-Jen Liou, Amooru G Damu, Tian-Shung Wu. Acetophenone derivatives from Acronychia pedunculata. Journal of natural products. 2003 Jul; 66(7):990-3. doi: 10.1021/np030054x. [PMID: 12880321]
  • Iván Bélai, Gábor Fekete. Effects of anti-ecdysteroid quaternary derivatives of azole analogues of metyrapone on the post-embryonic development of the red cotton bug (Dysdercus cingulatus F). Pest management science. 2003 Apr; 59(4):401-9. doi: 10.1002/ps.646. [PMID: 12701700]
  • Araceli Sala, M Carmen Recio, Guillermo R Schinella, Salvador Máñez, Rosa M Giner, José-Luis Ríos. A new dual inhibitor of arachidonate metabolism isolated from Helichrysum italicum. European journal of pharmacology. 2003 Jan; 460(2-3):219-26. doi: 10.1016/s0014-2999(02)02954-0. [PMID: 12559384]
  • Carlos L Céspedes, Adjaci Uchoa, Juan R Salazar, Fernando Perich, Fernando Pardo. Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study. Journal of agricultural and food chemistry. 2002 Apr; 50(8):2283-92. doi: 10.1021/jf011108g. [PMID: 11929285]
  • M Gul, H I Gul, O Hänninen. Effects of Mannich bases on cellular glutathione and related enzymes of Jurkat cells in culture conditions. Toxicology in vitro : an international journal published in association with BIBRA. 2002 Apr; 16(2):107-12. doi: 10.1016/s0887-2333(01)00115-1. [PMID: 11869872]
  • Luis Góngora, Salvador Máñez, Rosa M Giner, M Carmen Recio, Alexander I Gray, José Luis Ríos. Phenolic glycosides from Phagnalon rupestre. Phytochemistry. 2002 Apr; 59(8):857-60. doi: 10.1016/s0031-9422(02)00011-0. [PMID: 11937166]