Acetophenone (BioDeep_00000000092)

 

Secondary id: BioDeep_00000860684

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


Acetophenone, TraceCERT(R), certified reference material

化学式: C8H8O (120.0575)
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) 26.14%

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Acetophenone is a methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.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A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.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。

亚细胞结构定位 关联基因列表
Cytoplasm 4 CAT, MAPK14, RPS6, TYR
Peripheral membrane protein 2 ACHE, GBA1
Endoplasmic reticulum membrane 1 CYP1A2
Nucleus 5 ACHE, GCAT, MAPK14, MN1, RPS6
cytosol 3 CAT, MAPK14, RPS6
dendrite 3 CHRNA4, EPHA7, RPS6
trans-Golgi network 1 GBA1
nucleoplasm 4 GCAT, MAPK14, PNN, RPS6
Cell membrane 6 ACHE, ADRB3, CD244, CHRNA4, EPHA7, TRPV1
Lipid-anchor 1 CHRNA4
Multi-pass membrane protein 3 ADRB3, CHRNA4, TRPV1
Synapse 2 ACHE, CHRNA4
cell surface 1 ACHE
glutamatergic synapse 2 EPHA7, MAPK14
Golgi apparatus 3 ACHE, ATRN, GBA1
Golgi membrane 1 INS
lysosomal membrane 2 GAA, GBA1
mitochondrial inner membrane 1 GCAT
neuromuscular junction 1 ACHE
neuronal cell body 2 CHRNA4, TRPV1
postsynapse 1 CHRNA4
Lysosome 3 GAA, GBA1, TYR
plasma membrane 10 ACHE, ADRB3, ATRN, BCHE, CD244, CHRNA4, EPHA7, GAA, PNN, TRPV1
Membrane 9 ACHE, CAT, CD244, CHRNA4, EPHA7, GAA, PNN, RPS6, TRPV1
extracellular exosome 4 ATRN, CAT, GAA, GBA1
Lysosome membrane 2 GAA, GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 2 GBA1, RPS6
extracellular space 5 ACHE, ATRN, BCHE, INS, OBP2A
lysosomal lumen 2 GAA, GBA1
perinuclear region of cytoplasm 3 ACHE, RPS6, TYR
mitochondrion 3 CAT, GCAT, MAPK14
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 4 CAT, CYP1A2, GAA, TYR
Microsome membrane 1 CYP1A2
Single-pass type I membrane protein 4 ATRN, CD244, EPHA7, TYR
Secreted 5 ACHE, BCHE, GAA, INS, OBP2A
extracellular region 7 ACHE, BCHE, CAT, GAA, INS, MAPK14, OBP2A
[Isoform 2]: Secreted 1 ATRN
mitochondrial matrix 1 CAT
Extracellular side 1 ACHE
external side of plasma membrane 3 CD244, CHRNA4, TRPV1
nucleolus 1 RPS6
Melanosome membrane 1 TYR
cell-cell junction 1 PNN
Golgi-associated vesicle 1 TYR
postsynaptic membrane 2 CHRNA4, TRPV1
Membrane raft 1 CD244
focal adhesion 1 CAT
GABA-ergic synapse 1 TRPV1
Peroxisome 1 CAT
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
intermediate filament 1 PNN
nuclear speck 3 GCAT, MAPK14, PNN
Postsynaptic cell membrane 2 CHRNA4, TRPV1
receptor complex 1 ADRB3
Cell projection, neuron projection 1 TRPV1
neuron projection 1 CHRNA4
cytoplasmic ribonucleoprotein granule 1 RPS6
Nucleus, nucleolus 1 RPS6
spindle pole 1 MAPK14
blood microparticle 1 BCHE
Lipid-anchor, GPI-anchor 1 ACHE
[Isoform 3]: Secreted 1 ATRN
endosome lumen 1 INS
tertiary granule membrane 1 GAA
Melanosome 1 TYR
cell body 1 RPS6
side of membrane 1 ACHE
ficolin-1-rich granule lumen 2 CAT, MAPK14
secretory granule lumen 3 CAT, INS, MAPK14
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 BCHE, INS
transport vesicle 1 INS
azurophil granule membrane 1 GAA
small-subunit processome 1 RPS6
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
nuclear envelope lumen 1 BCHE
ribonucleoprotein complex 1 RPS6
synaptic cleft 1 ACHE
ficolin-1-rich granule membrane 1 GAA
[Isoform 1]: Cell membrane 1 ATRN
catalytic step 2 spliceosome 1 PNN
desmosome 1 PNN
cytosolic ribosome 1 RPS6
Cell projection, dendritic spine membrane 1 TRPV1
dendritic spine membrane 1 TRPV1
ribosome 1 RPS6
acetylcholine-gated channel complex 1 CHRNA4
catalase complex 1 CAT
cytosolic small ribosomal subunit 1 RPS6
autolysosome lumen 1 GAA
[Isoform H]: Cell membrane 1 ACHE
small ribosomal subunit 1 RPS6


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]
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  • 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]
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