Paeonol

Last updated
Paeonol
Paeonol.svg
Names
Preferred IUPAC name
1-(2-Hydroxy-4-methoxyphenyl)ethan-1-one
Other names
2'-Hydroxy-4'-methoxyacetophenone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.194 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H10O3/c1-6(10)8-4-3-7(12-2)5-9(8)11/h3-5,11H,1-2H3
    Key: UILPJVPSNHJFIK-UHFFFAOYSA-N
  • InChI=1/C9H10O3/c1-6(10)8-4-3-7(12-2)5-9(8)11/h3-5,11H,1-2H3
    Key: UILPJVPSNHJFIK-UHFFFAOYAG
  • CC(=O)C1=C(C=C(C=C1)OC)O
Properties
C9H10O3
Molar mass 166.176 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Paeonol is a phenolic compound found in peonies [2] such as Paeonia suffruticosa (moutan cortex), [3] [4] in Arisaema erubescens , [5] and in Dioscorea japonica . [6] It is a chemical compound found in some traditional Chinese medicines. [7]

Contents

Biological effects

A number of biological effects of paeonol in vitro or in animal models have been observed. Paeonol increases levels of cortical cytochrome oxidase and vascular actin and improves behavior in a rat model of Alzheimer's disease. [8] Paeonol also reduced cerebral infarction involving the superoxide anion and microglia activation in ischemia-reperfusion injured rats. [9]

Paeonol shows antimutagenic activities. [3] [6] It also has anti-inflammatory and analgesic effects in carrageenan-evoked thermal hyperalgesia. [10] Paeonol inhibits anaphylactic reaction by regulating histamine and TNF-α. [11]

Paeonol has weak MAO-A and MAO-B inhibiting effects with IC50 values of 54.6 μM and 42.5 μM respectively. [12]

Metal complex

Metal complexes of paeonol shows tetrahedral and octahedral coordination geometry in the absence and presence of solvent pyridine respectively. [13]

References

  1. ↑ "CAS # 552-41-0, Paeonol, 2'-Hydroxy-4'-methoxyacetophenone, 1-(2-hydroxy-4-methoxyphenyl)ethan-1-one".
  2. ↑ Zhang, L.; Li, D. C.; Liu, L. F. (2019). "Paeonol: pharmacological effects and mechanisms of action". International immunopharmacology. 72: 413–421. doi:10.1016/j.intimp.2019.04.033. PMID   31030097.
  3. 1 2 Fukuhara Y, Yoshida D (1987). "Paeonol: a bio-antimutagen isolated from a crude drug, moutan cortex". Agricultural and Biological Chemistry. 51 (5): 1441–1442. doi: 10.1271/bbb1961.51.1441 . INIST   7609719.
  4. ↑ Wu, Xinan; Chen, Hongli; Chen, Xingguo; Hu, Zhide (2003). "Determination of paeonol in rat plasma by high-performance liquid chromatography and its application to pharmacokinetic studies following oral administration of Moutan cortex decoction". Biomedical Chromatography. 17 (8): 504–8. doi:10.1002/bmc.259. PMID   14648606.
  5. ↑ Ducki S, Hadfield JA, Lawrence NJ, Zhang X, McGown AT (1995). "Isolation of paeonol from Arisaema erubescens". Planta Medica. 61 (6): 586–587. doi:10.1055/s-2006-959390. PMID   8824957. INIST   2920867.
  6. 1 2 Miyazawa, Mitsuo; Shimamura, Hideo; Nakamura, Sei-Ichi; Kameoka, Hiromu (1996). "Antimutagenic Activity of (+)-β-Eudesmol and Paeonol from Dioscorea japonica". Journal of Agricultural and Food Chemistry. 44 (7): 1647–1650. Bibcode:1996JAFC...44.1647M. doi:10.1021/jf950792u.
  7. ↑ Deng, Chunhui; Yao, Ning; Wang, Ben; Zhang, Xiangmin (2006). "Development of microwave-assisted extraction followed by headspace single-drop microextraction for fast determination of paeonol in traditional Chinese medicines". Journal of Chromatography A. 1103 (1): 15–21. doi:10.1016/j.chroma.2005.11.023. PMID   16309693.
  8. ↑ Zhou, Jun; Zhou, Li; Hou, Deren; Tang, Jiaochun; Sun, Juanjuan; Bondy, Stephen C. (2011). "Paeonol increases levels of cortical cytochrome oxidase and vascular actin and improves behavior in a rat model of Alzheimer's disease" (PDF). Brain Research. 1388: 141–7. doi:10.1016/j.brainres.2011.02.064. PMID   21377451. S2CID   12668336.
  9. ↑ Hsieh, Ching-Liang; Cheng, Chin-Yi; Tsai, Tung-Hu; Lin, I-Hsin; Liu, Chung-Hsiang; Chiang, Su-Yin; Lin, Jaung-Geng; Lao, Chih-Jui; Tang, Nou-Ying (2006). "Paeonol reduced cerebral infarction involving the superoxide anion and microglia activation in ischemia-reperfusion injured rats". Journal of Ethnopharmacology. 106 (2): 208–15. doi:10.1016/j.jep.2005.12.027. PMID   16458462.
  10. ↑ Chou, Tz-Chong (2003). "Anti-inflammatory and analgesic effects of paeonol in carrageenan-evoked thermal hyperalgesia". British Journal of Pharmacology. 139 (6): 1146–52. doi:10.1038/sj.bjp.0705360. PMC   1573952 . PMID   12871833.
  11. ↑ Kim, Sung Hoon; Kim, Seung-Ae; Park, Mi-Kyung; Kim, Seung-Hyung; Park, Young-Doo; Na, Ho-Jeong; Kim, Hyung-Min; Shin, Min-Kyu; Ahn, Kyoo-Seok (2004). "Paeonol inhibits anaphylactic reaction by regulating histamine and TNF-α". International Immunopharmacology. 4 (2): 279–87. doi:10.1016/j.intimp.2003.12.013. PMID   14996419.
  12. ↑ Kong, L.D.; Cheng, Christopher H.K.; Tan, R.X. (2004). "Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones". Journal of Ethnopharmacology. 91 (2–3): 351–355. doi:10.1016/j.jep.2004.01.013. PMID   15120460.
  13. ↑ Patel, Mahesh kumar (2019). "Solvent effect on neutral Co (II) complexes of paeonol derivative equalitative and quantitative studies from energy frame work and Hirshfeld surface analysis". Journal of Molecular Structure. 1196: 119–131. Bibcode:2019JMoSt1196..119P. doi:10.1016/j.molstruc.2019.06.050. S2CID   197231895.
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