Piceol (BioDeep_00000397446)

PANOMIX_OTCML-2023

代谢物信息卡片

4-Hydroxyacetophenone (Acetaminophen Impurity E), Pharmaceutical Secondary Standards; Certified Reference Material

化学式: C8H8O2 (136.0524)
中文名称: 4-羟基苯乙酮, 对羟基苯乙酮
谱图信息: 最多检出来源 Viridiplantae(plant) 8.8%

分子结构信息

SMILES: c1cc(ccc1C(=O)C)O
InChI: InChI=1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3

描述信息

4-hydroxyacetophenone is a monohydroxyacetophenone carrying a hydroxy substituent at position 4. It has a role as a plant metabolite, a fungal metabolite and a mouse metabolite.
4-Hydroxyacetophenone is a natural product found in Ficus erecta var. beecheyana, Artemisia ordosica, and other organisms with data available.
A monohydroxyacetophenone carrying a hydroxy substituent at position 4.
4-Hydroxyacetophenone (P-hydroxyacetophenone) is a key hepatoprotective and choleretic compound in Artemisia capillaris and A. morrisonensis, also has an anti-hepatitis B virus effect and anti-inflammatory effect[1].
4-Hydroxyacetophenone (P-hydroxyacetophenone) is a key hepatoprotective and choleretic compound in Artemisia capillaris and A. morrisonensis, also has an anti-hepatitis B virus effect and anti-inflammatory effect[1].

同义名列表

60 个代谢物同义名

4-Hydroxyacetophenone (Acetaminophen Impurity E), Pharmaceutical Secondary Standards; Certified Reference Material; 1-(4-Hydroxyphenyl)ethanone; Paracetamol Imp. E (EP); 4-Hydroxyacetophenone; Paracetamol Impurity E; 1-(4-Hydroxyphenyl)ethanone (4-Hydroxyacetophenone); InChI=1/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H; 4 inverted exclamation mark -Hydroxyacetophenone; 4-Hydroxyacetophenone, analytical standard; PARACETAMOL IMPURITY E [EP IMPURITY]; 1-(4-hydroxyphenyl)-1-ethanone; Ethanone, 1-(4-hydroxyphenyl)-; 1-(4-Hydroxyphenyl)Ethan-1-One; 4-Hydroksyacetofenol [Polish]; 4-Hydroxyphenyl Methyl Ketone; Methyl-p-hydroxyphenyl ketone; p-Hydroxyphenyl methyl ketone; 1-(4-Hydroxy-phenyl)-ethanone; Methyl p-hydroxyphenyl ketone; 1-(4-hydroxyphenyl)-ethanone; 1-(4-hydroxyphenyl) ethanone; 4-HYDROXYACETOPHENONE [FHFI]; (4-Hydroxyphenyl)ethan-1-one; 4-Hydroxyacetophenone, 99\\%; 1-(4-hydroxyphenyl)ethanone; HYDROXYACETOPHENONE [INCI]; HYDROXYACETOPHENONE, PARA; (4-hydroxyphenyl)ethanone; Acetophenone, 4-hydroxy-; Acetaminophen Impurity E; Acetophenone, p-hydroxy-; para-hydroxyacetophenone; parahydroxyacetophenone; rho-hydroxyacetophenone; p-hydroxy acetophenone; p-hydroxy-acetophenone; 4-hydroxy acetophenone; Paracetamol Impurity E; 4-hydroxyacetophenone; 4-Hydroxyacetophenone; p-hydroxyacetophenone; p-Hydroxacetophenone; 4-Hydroksyacetofenol; 4-hyroxyacetophenone; Phenol, p-acetyl-; p-Oxyacetophenone; UNII-G1L3HT4CMH; 4-Acetylphenol; p-Acetylphenol; 4-Acetophenol; Tox21_303602; Tox21_200228; CAS-99-93-4; WLN: QR DV1; G1L3HT4CMH; USAF KF-15; AI3-12133; piceol; 4-HAP; 2o48; AC6; 4'-Hydroxyacetophenone; 4-Hydroxyacetophenone

数据库引用编号

16 个数据库交叉引用编号

ChEBI: CHEBI:28032
KEGG: C10700
PubChem: 7469
ChEMBL: CHEMBL201083
Wikipedia: Piceol
MeSH: 4-hydroxyacetophenone
ChemIDplus: 0000099934
KNApSAcK: C00002698
CAS: 99-93-4
medchemexpress: HY-Y0073
MetaboLights: MTBLC28032
PubChem: 12883
PDB-CCD: AC6
3DMET: B04072
NIKKAJI: J4.976J
KNApSAcK: 28032

分类词条

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)

92 个相关的物种来源信息

97171 - Abies nephrolepis: 10.1002/CBDV.201000373
342581 - Abies spectabilis: 10.1248/CPB.58.1646
175969 - Aeschynanthus bracteatus: 10.1016/J.PHYTOCHEM.2008.05.012
176617 - Ageratina glechonophylla: 10.1016/S0031-9422(00)81124-3
117798 - Aloe ferox: 10.1271/BBB.60659
13339 - Apocynum cannabinum: 10.1055/S-0028-1101540
377125 - Apocynum venetum L.: -
1227617 - Artemisia assoana: 10.1016/S0031-9422(00)83891-1
72335 - Artemisia barrelieri: 10.1016/0031-9422(91)80088-I
72337 - Artemisia campestris: 10.1016/S0031-9422(00)83971-0
265783 - Artemisia capillaris: 10.1016/J.BMCL.2015.02.024
72339 - Artemisia chamaemelifolia:
401898 - Artemisia gmelinii: 10.1055/S-2007-969446
72329 - Artemisia herba-alba:
1238151 - Artemisia igniaria: 10.1055/S-2000-8632
223868 - Artemisia japonica: 10.1007/BF02978255
72345 - Artemisia lucentica: 10.1016/0031-9422(88)80018-9
86312 - Artemisia ludoviciana: 10.1016/0031-9422(86)80021-8
205371 - Artemisia marschalliana: 10.1016/S0031-9422(00)88402-2
1027791 - Artemisia ordosica: 10.1007/S11418-009-0385-X
401925 - Artemisia palustris: 10.1016/0031-9422(86)80021-8
72350 - Artemisia reptans: 10.1016/0031-9422(88)80018-9
205374 - Artemisia rutifolia: 10.1016/0031-9422(86)80021-8
205376 - Artemisia santolinifolia: 10.1055/S-2007-969446
72351 - Artemisia scoparia: 10.1002/PTR.2650050410
401941 - Artemisia xanthochroa: 10.1016/0031-9422(90)85307-2
41487 - Baccharis: 10.1021/JF011108G
1654447 - Baccharis patagonica: 10.1016/S0031-9422(00)83754-1
1423 - Bacillus subtilis: 10.1007/S10600-009-9270-9
72904 - Boltonia asteroides: 10.1016/S0031-9422(00)89801-5
41511 - Centaurea calcitrapa: 10.1007/S10600-007-0232-9
2565749 - Centaurea regia: 10.1016/0031-9422(88)83055-3
72914 - Chrysothamnus viscidiflorus: 10.1016/0031-9422(80)83015-9
171766 - Chuquiraga spinosa:
13443 - Coffea arabica: 10.1021/JF60160A010
228707 - Cynanchum boudieri: 10.1021/NP960256B
698326 - Cynanchum bungei: 10.1248/CPB.40.3133
228709 - Cynanchum wilfordii: 10.1016/S0031-9422(97)00403-2
1548336 - Cyrtocymura scorpioides: 10.1016/0031-9422(90)85300-5
1928361 - Cytospora ceratosperma: 10.1271/BBB1961.46.2101
18795 - Delairea odorata: 10.1021/NP049831Z
2708818 - Drypetes gossweileri: 10.1016/J.PHYTOL.2010.10.007
53751 - Echinacea purpurea: 10.1055/S-2005-873201
317934 - Fabiana imbricata:
1008913 - Ficus erecta var. beecheyana: 10.1002/JCCS.200400067
2604040 - Flourensia riparia: 10.1016/J.PHYTOCHEM.2004.05.009
462437 - Gynoxys buxifolia: 10.1016/0031-9422(95)00543-G
2304422 - Haplopappus arbutoides: 10.1016/0031-9422(91)80089-J
71052 - Haplopappus glutinosus:
147776 - Haplopappus paucidentatus: 10.1016/S0031-9422(00)81166-8
261805 - Helichrysum stoechas: 10.1023/B:CONC.0000033925.00693.7B
34205 - Iris germanica: 10.1248/YAKUSHI1947.101.12_1118
2039844 - Lagochilus leiacanthus: 10.1248/CPB.59.1535
72228 - Ophiocordyceps sinensis: 10.1021/NP100902F
223102 - Orobanche crenata: 10.1055/S-2006-958118
36748 - Orobanche minor: 10.1055/S-2006-958118
45171 - Paeonia suffruticosa: 10.1002/JCCS.200000051
44586 - Panax Notoginseng (Burk.) F. H. Chen Ex C. Chow: -
69765 - Penicillium bilaiae: 10.1007/BF01104007
3329 - Picea abies:
3330 - Picea glauca: 10.1016/S0031-9422(96)00388-3
33090 - Plants: -
62097 - Plumeria rubra: 10.1016/0378-8741(91)90091-Q
3694 - Populus trichocarpa: 10.1515/ZNC-1987-9-1004
55489 - Posidonia oceanica: 10.1016/S0031-9422(97)01118-7
36596 - Prunus armeniaca: 10.1021/JF00004A032
3758 - Prunus domestica: 10.1021/JF00004A032
3760 - Prunus persica: 10.1021/JF00004A032
642531 - Pyrola incarnata: 10.1248/CPB.40.2083
642532 - Pyrola japonica: 10.1248/CPB.40.2083
13651 - Pyrola rotundifolia: 10.1248/CPB.40.2083
98718 - Robinsonecio gerberifolius: 10.1021/NP0203739
4463 - Sauromatum venosum: 10.1016/S0031-9422(00)94756-3
378341 - Saussurea simpsoniana: 10.1007/S10600-010-9659-5
182070 - Saxifraga Stolonifera: -
462527 - Senecio filaginoides: 10.1002/BSCB.19860950903
189247 - Senecio scandens: 10.1021/NP049831Z
403019 - Sideritis discolor: 10.1016/J.PHYTOCHEM.2009.05.011
155263 - Sideritis soluta: 10.1016/J.PHYTOCHEM.2009.05.011
128215 - Sphagnum magellanicum: 10.1016/0031-9422(94)00650-I
112400 - Syncarpha gnaphaloides: 10.1016/0031-9422(89)80045-7
189254 - Synotis nagensium: 10.1021/NP049831Z
457738 - Tanacetopsis mucronata: 10.1007/BF00575207
2072400 - Tanacetum sinaicum:
1547788 - Tarenna attenuata: 10.1055/S-2007-967165
479928 - Tephroseris flammea: 10.1002/CHIN.199848194
78479 - Trollius Chinensis: -
157443 - Vincetoxicum atratum:
29760 - Vitis vinifera: 10.3389/FMICB.2017.00457
462589 - Werneria nubigena: 10.1016/S0031-9422(97)00341-5
224084 - Wikstroemia canescens: 10.1248/CPB.60.554
751879 - Ziziphora clinopodioides: 10.1016/J.FITOTE.2011.11.023

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	12	CYP1A1, CYP3A4, FLNA, FLNB, GSTA2, MYH10, MYH14, MYH9, MYLK, PFDN5, PTGS2, XDH
Peripheral membrane protein	2	CYP1A1, PTGS2
Endoplasmic reticulum membrane	3	CYP1A1, CYP3A4, PTGS2
Nucleus	6	ADK, APCS, FLNA, MYH10, MYH9, PFDN5
cytosol	11	ADK, FLNA, FLNB, GSR, GSTA2, MYH10, MYH14, MYH9, MYLK, PFDN5, XDH
dendrite	1	CHRNA4
nuclear body	1	MYH9
phagocytic vesicle	1	FLNB
trans-Golgi network	1	FLNA
nucleoplasm	1	ADK
Cell membrane	4	CHRNA4, MYH10, MYH9, SLC26A5
Lipid-anchor	1	CHRNA4
Cleavage furrow	3	MYH10, MYH9, MYLK
lamellipodium	2	MYH10, MYLK
Cell projection, growth cone	1	FLNA
Multi-pass membrane protein	2	CHRNA4, SLC26A5
Synapse	2	CHRNA4, MYLK
cell cortex	2	FLNB, MYH10
dendritic shaft	1	FLNA
glutamatergic synapse	1	FLNA
growth cone	1	MYH14
mitochondrial inner membrane	1	CYP1A1
neuromuscular junction	1	MYH9
neuronal cell body	1	CHRNA4
postsynapse	2	CHRNA4, FLNA
plasma membrane	8	ADK, BCHE, CHRNA4, FLNA, FLNB, MYH9, MYLK, SLC26A5
Membrane	7	CHRNA4, CYP3A4, FLNA, FLNB, MYH14, MYH9, SLC26A5
basolateral plasma membrane	1	SLC26A5
brush border	4	FLNA, FLNB, MYH14, MYH9
caveola	1	PTGS2
extracellular exosome	8	APCS, FLNA, FLNB, GSR, GSTA2, MYH10, MYH14, MYH9
endoplasmic reticulum	1	PTGS2
extracellular space	4	APCS, BCHE, IL6, XDH
perinuclear region of cytoplasm	1	FLNA
adherens junction	1	MYH9
mitochondrion	2	CYP1A1, GSR
protein-containing complex	2	MYH9, PTGS2
intracellular membrane-bounded organelle	2	CYP1A1, CYP3A4
Microsome membrane	3	CYP1A1, CYP3A4, PTGS2
Secreted	3	APCS, BCHE, IL6
extracellular region	4	APCS, BCHE, FLNA, IL6
cytoplasmic side of plasma membrane	1	MYH9
mitochondrial matrix	1	GSR
external side of plasma membrane	2	CHRNA4, GSR
actin cytoskeleton	4	FLNA, FLNB, MYH9, MYLK
perikaryon	1	FLNA
Z disc	2	FLNA, FLNB
nucleolus	1	FLNA
midbody	1	MYH10
cell-cell junction	1	FLNA
postsynaptic membrane	1	CHRNA4
Cell projection, lamellipodium	2	MYH10, MYLK
Mitochondrion inner membrane	1	CYP1A1
Cytoplasm, cytoskeleton	2	FLNA, MYH9
focal adhesion	3	FLNA, FLNB, MYH9
spindle	1	MYH9
Peroxisome	1	XDH
sarcoplasmic reticulum	1	XDH
collagen-containing extracellular matrix	1	APCS
lateral plasma membrane	1	SLC26A5
actomyosin	3	MYH10, MYH14, MYH9
Nucleus inner membrane	1	PTGS2
Nucleus outer membrane	1	PTGS2
nuclear inner membrane	1	PTGS2
nuclear outer membrane	1	PTGS2
Postsynaptic cell membrane	1	CHRNA4
ruffle	1	MYH9
neuron projection	2	CHRNA4, PTGS2
axonal growth cone	1	FLNA
cell leading edge	1	MYH9
supramolecular fiber	3	MYH10, MYH14, MYH9
Cell projection, podosome	1	FLNA
podosome	1	FLNA
Cytoplasm, cell cortex	2	FLNA, MYH9
actin filament	1	FLNA
blood microparticle	2	APCS, BCHE
myosin filament	3	MYH10, MYH14, MYH9
myosin II complex	3	MYH10, MYH14, MYH9
myosin complex	3	MYH10, MYH14, MYH9
intermediate filament cytoskeleton	1	PFDN5
stress fiber	5	FLNB, MYH10, MYH14, MYH9, MYLK
endoplasmic reticulum lumen	3	BCHE, IL6, PTGS2
immunological synapse	1	MYH9
nuclear envelope lumen	1	BCHE
[Isoform 2]: Cytoplasm	1	ADK
Cytoplasm, cytoskeleton, stress fiber	1	MYLK
uropod	1	MYH9
[Isoform 1]: Nucleus	1	ADK
prefoldin complex	1	PFDN5
Lateral cell membrane	1	SLC26A5
apical dendrite	1	FLNA
intracellular non-membrane-bounded organelle	2	FLNA, FLNB
postsynaptic actin cytoskeleton	1	MYH10
actin filament bundle	1	FLNA
acetylcholine-gated channel complex	1	CHRNA4
cortical cytoskeleton	1	FLNA
interleukin-6 receptor complex	1	IL6
glycoprotein Ib-IX-V complex	1	FLNA
Cytoplasmic vesicle, secretory vesicle, Cortical granule	1	MYH9
cortical granule	1	MYH9
Myb complex	1	FLNA
actomyosin contractile ring	1	MYH9
myosin II filament	3	MYH10, MYH14, MYH9
lateral wall of outer hair cell	1	SLC26A5
organelle	1	FLNB

文献列表

Huiqing Piao, Wanchen Xie, Shiqi Li, Jiaqi Wang, Chao Liu, Peng Quan, Liang Fang. Ternary Deep Eutectic Solvents System of Colchicine, 4-Hydroxyacetophenone, and Protocatechuic Acid and Characterization of Transdermal Enhancement Mechanism. AAPS PharmSciTech. 2023 Nov; 24(8):229. doi: 10.1208/s12249-023-02681-x. [PMID: 37964102]
Gari V Ccana-Ccapatinta, Guillermo F Padilla-Gonzalez, Paola L Ferreira, Marcelo Monge, Joao Semir, Milton Groppo, Fernando B Da Costa. High-Resolution Liquid Chromatography-Mass Spectrometry-Based Metabolomics for the Classification of Chuquiraga (Barnadesioideae, Asteraceae): New Phenylpropanoid Derivatives as Chemical Markers for Chuquiraga spinosa. Journal of natural products. 2023 Mar; ?(?):. doi: 10.1021/acs.jnatprod.2c00603. [PMID: 36913505]
Liangyu Lu, Xiaolei Wang, Lei Zhou, Qiyuan Liu, Guanghao Zhang, Bingqing Xue, Chenyu Hu, Xiaolin Shen, Xinxiao Sun, Yajun Yan, Jia Wang, Qipeng Yuan. Establishing biosynthetic pathway for the production of p-hydroxyacetophenone and its glucoside in Escherichia coli. Metabolic engineering. 2023 Feb; 76(?):110-119. doi: 10.1016/j.ymben.2023.02.001. [PMID: 36746296]
Juan Zou, Yuanyuan Li, Jingyi Cai, Xiaotian Peng, Lincong Zhang, Tian Tian, Tianming Wang, Rong Shi, Jiasheng Wu, Yueming Ma. Identification of Yinchenwuling fang's active components and hepatoprotective effects against cholestatic liver damage induced by alpha-naphthyl isothiocyanate in mice. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2023 Jan; 1215(?):123570. doi: 10.1016/j.jchromb.2022.123570. [PMID: 36542898]
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]
Nur Hanis Abd Latif, Afidah Abdul Rahim, Nicolas Brosse, M Hazwan Hussin. The structural characterization and antioxidant properties of oil palm fronds lignin incorporated with p-hydroxyacetophenone. International journal of biological macromolecules. 2019 Jun; 130(?):947-957. doi: 10.1016/j.ijbiomac.2019.03.032. [PMID: 30851323]
Yuan Xu, Long Chen, Yi-Xin Jiang, Yue Yang, Dan-Dan Zhang. [Regulatory effect and relevant mechanisms of fraction from heat-clearing and detoxifying herb couplet on macrophage M1/M2 phenotypes]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2018 Sep; 43(18):3722-3728. doi: 10.19540/j.cnki.cjcmm.20180522.003. [PMID: 30384539]
Takashi Uchikura, Hiroaki Tanaka, Hidemi Sugiwaki, Morio Yoshimura, Naoko Sato-Masumoto, Takashi Tsujimoto, Nahoko Uchiyama, Takashi Hakamatsuka, Yoshiaki Amakura. Preliminary Quality Evaluation and Characterization of Phenolic Constituents in Cynanchi Wilfordii Radix. Molecules (Basel, Switzerland). 2018 Mar; 23(3):. doi: 10.3390/molecules23030656. [PMID: 29538318]
Geneviève J Parent, Isabelle Giguère, Melissa Mageroy, Joerg Bohlmann, John J MacKay. Evolution of the biosynthesis of two hydroxyacetophenones in plants. Plant, cell & environment. 2018 03; 41(3):620-629. doi: 10.1111/pce.13134. [PMID: 29314043]
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]
Di Wu, Xuan Chen, Shuang Hu, Xiaohong Bai. Study on major antitumor components in Yinchenhao decoction in vitro and in vivo based on hollow fiber cell fishing coupled with high performance liquid chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Aug; 1060(?):118-125. doi: 10.1016/j.jchromb.2017.06.003. [PMID: 28609699]
Chang Ching-Wen, Chen Yun-Chieh, Lin Yu-Chin, Peng Wen-Huang. p-Hydroxyacetophenone suppresses nuclear factor-κB-related inflammation in nociceptive and inflammatory animal models. Journal of natural medicines. 2017 Apr; 71(2):422-432. doi: 10.1007/s11418-017-1074-9. [PMID: 28150144]
Di Zhou, Hongyan Wei, Zhe Jiang, Xuezheng Li, Kun Jiao, Xiaoguang Jia, Yue Hou, Ning Li. Natural potential neuroinflammatory inhibitors from Alhagi sparsifolia Shap. Bioorganic & medicinal chemistry letters. 2017 02; 27(4):973-978. doi: 10.1016/j.bmcl.2016.12.075. [PMID: 28073678]
Jinlong Yang, Yichao Cheng, Yuanyuan Zhu, Junjun Zhu, Tingting Chen, Yong Xu, Qiang Yong, Shiyuan Yu. [Effect of phenolic ketones on ethanol fermentation and cellular lipid composition of Pichia stipitis]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2016 Feb; 32(2):185-94. doi: . [PMID: 27382768]
Yong Zhao, Chang-An Geng, Hao Chen, Yun-Bao Ma, Xiao-Yan Huang, Tuan-Wu Cao, Kang He, Hao Wang, Xue-Mei Zhang, Ji-Jun Chen. Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris. Bioorganic & medicinal chemistry letters. 2015 Apr; 25(7):1509-14. doi: 10.1016/j.bmcl.2015.02.024. [PMID: 25737008]
Peng Liu, Xing Xu, Lili Chen, Lei Ma, Xu Shen, Lihong Hu. Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists. Bioorganic & medicinal chemistry. 2014 Mar; 22(5):1596-607. doi: 10.1016/j.bmc.2014.01.032. [PMID: 24513188]
Tsurng-Juhn Huang, Shu-Heng Liu, Yu-Cheng Kuo, Chia-Wen Chen, Shen-Chieh Chou. Antiviral activity of chemical compound isolated from Artemisia morrisonensis against hepatitis B virus in vitro. Antiviral research. 2014 Jan; 101(?):97-104. doi: 10.1016/j.antiviral.2013.11.007. [PMID: 24269476]
María Elena Sánchez-Mendoza, Juan Rodríguez-Silverio, José Fausto Rivero-Cruz, Héctor Isaac Rocha-González, Jorge Baruch Pineda-Farías, Jesús Arrieta. Antinociceptive effect and gastroprotective mechanisms of 3,5-diprenyl-4-hydroxyacetophenone from Ageratina pichinchensis. Fitoterapia. 2013 Jun; 87(?):11-9. doi: 10.1016/j.fitote.2013.03.015. [PMID: 23529015]
Oscar Enrique Piro, Gustavo Alberto Echeverría, Emilio Lizarraga, Elida Romano, César Atilio Nazareno Catalán, Silvia Antonia Brandán. Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2013 Jan; 101(?):196-203. doi: 10.1016/j.saa.2012.09.086. [PMID: 23103461]
Yinshi Sun, Zhengbo Liu, Jianhua Wang, Saifei Yang, Baiqing Li, Ning Xu. Aqueous ionic liquid based ultrasonic assisted extraction of four acetophenones from the Chinese medicinal plant Cynanchum bungei Decne. Ultrasonics sonochemistry. 2013 Jan; 20(1):180-6. doi: 10.1016/j.ultsonch.2012.07.002. [PMID: 22858158]
Xiao-Feng Li, Xiao-Ru Hu, Zhong Dai, Yan Zhang, Hong Liang, Rui-Chao Lin. [Study on chemical constituents of Carthamus tinctorius]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2012 Oct; 35(10):1616-9. doi: . [PMID: 23627128]
Cristina Quispe, Ezequiel Viveros-Valdez, Guillermo Schmeda-Hirschmann. Phenolic constituents of the Chilean herbal tea Fabiana imbricata R. et P. Plant foods for human nutrition (Dordrecht, Netherlands). 2012 Sep; 67(3):242-6. doi: 10.1007/s11130-012-0302-4. [PMID: 22850976]
Jin Bae Weon, Chul Young Kim, Hye Jin Yang, Choong Je Ma. Neuroprotective compounds isolated from Cynanchum paniculatum. Archives of pharmacal research. 2012 Mar; 35(4):617-21. doi: 10.1007/s12272-012-0404-4. [PMID: 22553053]
François Senejoux, Céline Demougeot, Parhat Kerram, Haji Akber Aisa, Alain Berthelot, Françoise Bévalot, Corine Girard-Thernier. Bioassay-guided isolation of vasorelaxant compounds from Ziziphora clinopodioides Lam. (Lamiaceae). Fitoterapia. 2012 Mar; 83(2):377-82. doi: 10.1016/j.fitote.2011.11.023. [PMID: 22155596]
Naheed Riaz, Muhammad Akram Naveed, Muhammad Saleem, Bushra Jabeen, Muhammad Ashraf, Syeda Abida Ejaz, Abdul Jabbar, Ishtiaq Ahmed. Cholinesterase inhibitory constituents from Ficus bengalensis. Journal of Asian natural products research. 2012; 14(12):1149-55. doi: 10.1080/10286020.2012.733702. [PMID: 23106601]
Hari Prasad Devkota, Masato Watanabe, Takashi Watanabe, Shoji Yahara. Phenolic compounds from the aerial parts of Diplomorpha canescens. Chemical & pharmaceutical bulletin. 2012; 60(4):554-6. doi: 10.1248/cpb.60.554. [PMID: 22466741]
YanFu Jiang, Hyun Gyu Choi, Ying Li, Yu Mi Park, Jong Hwa Lee, Do Hoon Kim, Je-Hyun Lee, Jong Keun Son, MinKyun Na, Seung Ho Lee. Chemical constituents of Cynanchum wilfordii and the chemotaxonomy of two species of the family Asclepiadacease, C. wilfordii and C. auriculatum. Archives of pharmacal research. 2011 Dec; 34(12):2021-7. doi: 10.1007/s12272-011-1203-z. [PMID: 22210026]
Yun-Jan Wang, Jinhui Dou, Kevin P Cross, Luis G Valerio. Computational analysis for hepatic safety signals of constituents present in botanical extracts widely used by women in the United States for treatment of menopausal symptoms. Regulatory toxicology and pharmacology : RTP. 2011 Feb; 59(1):111-24. doi: 10.1016/j.yrtph.2010.09.012. [PMID: 20920542]
Elsa Youngsteadt, Patricia Guerra Bustios, Coby Schal. Divergent chemical cues elicit seed collecting by ants in an obligate multi-species mutualism in lowland Amazonia. PloS one. 2010 Dec; 5(12):e15822. doi: 10.1371/journal.pone.0015822. [PMID: 21209898]
Yan Yang, Wei-lin Li, Ting Gong, Hong-qing Wang, Ruo-yun Chen. Studies on the chemical constituents of Anabasis aphylla L. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 Dec; 45(12):1523-6. doi: . [PMID: 21348421]
Wei-Sheng Feng, Zhen Li, Xiao-Ke Zheng, Yuan-Jing Li, Fang-Yi Su, Yan-Li Zhang. Chemical constituents of Saxifraga stolonifera (L.) Meeb. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 Jun; 45(6):742-6. doi: ". [PMID: 20939183]
Hong-Jhang Chen, Chun-Kuang Shih, Hsin-Yi Hsu, Wenchang Chiang. Mast cell-dependent allergic responses are inhibited by ethanolic extract of adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) testa. Journal of agricultural and food chemistry. 2010 Feb; 58(4):2596-601. doi: 10.1021/jf904356q. [PMID: 20102206]
Juan Yang, Xiaomei Cai, Shuzhen Mu, Xiaosheng Yang. [Phenolic compounds from Galium aparine var. tenerum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Jul; 34(14):1802-4. doi: ". [PMID: 19894511]
Yinshi Sun, Zhengbo Liu, Jianhua Wang, Ying Wang, Hongying Zhou, Wenli Zhang, Jun Wang, Gui Qiao. [Determination of four acetophenones in Radix Cynanchi bungei by high performance liquid chromatography-photodiode array detection]. Se pu = Chinese journal of chromatography. 2009 Jan; 27(1):114-6. doi: . [PMID: 19449554]
Xiao-Ming Tian, Shi-Zhong Chen, Peng-Fei Tu, Lian-Di Lei. [Studies on chemical constituents of aerial parts of Ammopiptanthus mongolicus]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Oct; 33(19):2204-6. doi: . [PMID: 19166007]
Xiao-jie Tan, Qing Li, Xiao-hui Chen, Zhi-wei Wang, Zheng-yuan Shi, Kai-shun Bi, Ying Jia. Simultaneous determination of 13 bioactive compounds in Herba Artemisiae Scopariae (Yin Chen) from different harvest seasons by HPLC-DAD. Journal of pharmaceutical and biomedical analysis. 2008 Aug; 47(4-5):847-53. doi: 10.1016/j.jpba.2008.04.010. [PMID: 18502075]
Seong Ho Jeon, Wanjoo Chun, Yong Joon Choi, Yong Soo Kwon. Cytotoxic constituents from the bark of Salix hulteni. Archives of pharmacal research. 2008 Aug; 31(8):978-82. doi: 10.1007/s12272-001-1255-9. [PMID: 18787784]
Zhuo-Ma Dawa, Yan Zhou, Yang Bai, Suo-Lang Gesang, Ping Xie, Li-Sheng Ding. [Studies on chemical constituents of Saussurea laniceps]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 May; 33(9):1032-5. doi: . [PMID: 18652351]
C Jacyn Baker, Norton M Mock, Daniel P Roberts, Kenneth L Deahl, Cathleen J Hapeman, Walter F Schmidt, Jan Kochansky. Interference by Mes [2-(4-morpholino)ethanesulfonic acid] and related buffers with phenolic oxidation by peroxidase. Free radical biology & medicine. 2007 Nov; 43(9):1322-7. doi: 10.1016/j.freeradbiomed.2007.07.020. [PMID: 17893045]
Jana Kalinova, Nadezda Vrchotova, Jan Triska. Exudation of allelopathic substances in buckwheat (Fagopyrum esculentum Moench). Journal of agricultural and food chemistry. 2007 Aug; 55(16):6453-9. doi: 10.1021/jf070795u. [PMID: 17630762]
Saeda Kametani, Akiko Kojima-Yuasa, Hiroe Kikuzaki, David Opare Kennedy, Mayumi Honzawa, Isao Matsui-Yuasa. Chemical constituents of cape aloe and their synergistic growth-inhibiting effect on Ehrlich ascites tumor cells. Bioscience, biotechnology, and biochemistry. 2007 May; 71(5):1220-9. doi: 10.1271/bbb.60659. [PMID: 17485848]
Xiao Yao, Gang Chen. Simultaneous determination of p-hydroxyacetophenone, chlorogenic acid, and caffeic acid in Herba Artemisiae Scopariae by capillary electrophoresis with electrochemical detection. Analytical and bioanalytical chemistry. 2007 May; 388(2):475-81. doi: 10.1007/s00216-007-1198-y. [PMID: 17333139]
Muhammad Iqbal Choudhary, Saima Jalil, Muddasir Israr. Inhibition of respiratory burst in human neutrophils and lipoxygenase enzyme by compounds from Haloxylon griffithii. Phytotherapy research : PTR. 2006 Oct; 20(10):840-3. doi: 10.1002/ptr.1914. [PMID: 16835879]
Henrik T Simonsen, Anne Adsersen, Louise Berthelsen, Søren B Christensen, Alfonso Guzmán, Per Mølgaard. Ethnopharmacological evaluation of radal (leaves of Lomatia hirsuta) and isolation of 2-methoxyjuglone. BMC complementary and alternative medicine. 2006 Aug; 6(?):29. doi: 10.1186/1472-6882-6-29. [PMID: 16945129]
Roumen Christov, Boryana Trusheva, Milena Popova, Vassya Bankova, Michel Bertrand. Chemical composition of propolis from Canada, its antiradical activity and plant origin. Natural product research. 2006 May; 20(6):531-6. doi: 10.1080/14786410500056918. [PMID: 16835083]
Roumen Christov, Boryana Trusheva, Milena Popova, Vassya Bankova, Michel Bertrand. Chemical composition of propolis from Canada, its antiradical activity and plant origin. Natural product research. 2005 Oct; 19(7):673-8. doi: 10.1080/14786410512331328159. [PMID: 16076637]
Magda Vosmanská, David Sýkora, Jan Fähnrich, Marcela Kovárová, Karel Volka. Extraction of p-hydroxyacetophenone and catechin from Norway spruce needles. Comparison of different extraction solvents. Analytical and bioanalytical chemistry. 2005 Jun; 382(4):1135-40. doi: 10.1007/s00216-005-3229-x. [PMID: 15906011]
Lilla Margl, Christian Ettenhuber, István Gyurján, Meinhart H Zenk, Adelbert Bacher, Wolfgang Eisenreich. Biosynthesis of benzofuran derivatives in root cultures of Tagetes patula via phenylalanine and 1-deoxy-D-xylulose 5-phosphate. Phytochemistry. 2005 Apr; 66(8):887-99. doi: 10.1016/j.phytochem.2005.02.022. [PMID: 15845407]
N Vrchotová, J Tríska, O Urban, L Peknic. Variability of catechin and 4-hydroxyacetophenone distribution in Norway spruce needles in relation to their position, age, and growing conditions. Environmental pollution (Barking, Essex : 1987). 2004 Sep; 131(1):55-9. doi: 10.1016/j.envpol.2004.02.004. [PMID: 15210275]
Jian-Qiao Gu, Yuehong Wang, Scott G Franzblau, Gloria Montenegro, Barbara N Timmermann. Constituents of Senecio chionophilus with potential antitubercular activity. Journal of natural products. 2004 Sep; 67(9):1483-7. doi: 10.1021/np049831z. [PMID: 15387646]
Hasan Kirmizibekmez, Ihsan Calis, Remo Perozzo, Reto Brun, Ali A Dönmez, Anthony Linden, Peter Rüedi, Deniz Tasdemir. Inhibiting activities of the secondary metabolites of Phlomis brunneogaleata against parasitic protozoa and plasmodial enoyl-ACP Reductase, a crucial enzyme in fatty acid biosynthesis. Planta medica. 2004 Aug; 70(8):711-7. doi: 10.1055/s-2004-827200. [PMID: 15326547]
María L Uriburu, Juana R de la Fuente, Jorge Palermo, Roberto R Gil, Virginia E Sosa. Constituents of two Flourensia species. Phytochemistry. 2004 Jul; 65(14):2039-43. doi: 10.1016/j.phytochem.2004.05.009. [PMID: 15279969]
Guillermo Schmeda-Hirschmann, Alejandro Tapia, Cristina Theoduloz, Jaime Rodríguez, Susana López, Gabriela Egly Feresin. Free radical scavengers and antioxidants from Tagetes mendocina. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2004 May; 59(5-6):345-53. doi: 10.1515/znc-2004-5-610. [PMID: 18998399]
Andréa Mendes do Nascimento, Marcos José Salvador, Regina Celia Candido, Sérgio de Albuquerque, Dionéia C R de Oliveira. Trypanocidal and antifungal activities of p-hydroxyacetophenone derivatives from Calea uniflora (Heliantheae, Asteraceae). The Journal of pharmacy and pharmacology. 2004 May; 56(5):663-9. doi: 10.1211/0022357023231. [PMID: 15142345]
H B Klinke, L Olsson, A B Thomsen, B K Ahring. Potential inhibitors from wet oxidation of wheat straw and their effect on ethanol production of Saccharomyces cerevisiae: wet oxidation and fermentation by yeast. Biotechnology and bioengineering. 2003 Mar; 81(6):738-47. doi: 10.1002/bit.10523. [PMID: 12529889]
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]
Y S Li, S D Luo, M Zhang, J J Chen, Z T Wang. [Constituents of Liguliria vellerea (Franch.) Hand-Mazz]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2001 Dec; 26(12):835-7. doi: ". [PMID: 12776330]
H C Kwon, K R Lee. Phytochemical constituents of Artemisia japonica ssp. littoricola. Archives of pharmacal research. 2001 Jun; 24(3):194-7. doi: 10.1007/bf02978255. [PMID: 11440075]
M E Savard, J D Miller, L A Blais, K A Seifert, R A Samson. Secondary metabolites of Penicillium bilaii strain PB-50. Mycopathologia. 1994 Jul; 127(1):19-27. doi: 10.1007/bf01104007. [PMID: 7523950]
H Løkke. Picein and piceol concentrations in Norway spruce. Ecotoxicology and environmental safety. 1990 Jun; 19(3):301-9. doi: 10.1016/0147-6513(90)90032-z. [PMID: 2364913]
Q W Zhang, Y Z Zhang. [Determination of choleretic constituents in Artemisia scoparia Waldst. et Kit. by TLC densitometry]. Yao xue xue bao = Acta pharmaceutica Sinica. 1989 Jan; 24(1):43-7. doi: ". [PMID: 2801123]
A J Aladesanmi, O R Ilesanmi. Phytochemical and pharmacological investigation of the cardioactive constituents of the leaf of Dysoxylum lenticellare. Journal of natural products. 1987 Nov; 50(6):1041-4. doi: 10.1021/np50054a004. [PMID: 3443856]
W F Osswald, E F Elstner. Investigations on spruce decline in the Bavarian forest. Free radical research communications. 1987; 3(1-5):185-92. doi: 10.3109/10715768709069783. [PMID: 3508429]
Q W Zhang, Y Z Zhang. [Separation and determination of the cholagogic components in bin hao (Artemisia scoparia) by HPLC]. Yao xue xue bao = Acta pharmaceutica Sinica. 1986 Dec; 21(12):922-7. doi: ". [PMID: 3591333]
S X Wu, W L Huang, W Q Jin. Study of increased griseofulvin bioavailability with p-hydroxy acetophenone. Chinese medical journal. 1981 Apr; 94(4):237-40. doi: ". [PMID: 6790239]