Chemistry:Paeonol

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Paeonol
Chemical structure of paeonol
Names
Preferred IUPAC name
1-(2-Hydroxy-4-methoxyphenyl)ethan-1-one
Other names
2'-Hydroxy-4'-methoxyacetophenone
Identifiers
3D model (JSmol)
ChemSpider
UNII
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).
Infobox references
Tracking categories (test):

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]

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". http://www.chemblink.com/products/552-41-0.htm. 
  2. ↑ Zhang, L., Li, D. C., & Liu, L. F. (2019). Paeonol: pharmacological effects and mechanisms of action. International immunopharmacology, 72, 413-421. PMID 31030097 doi:10.1016/j.intimp.2019.04.033
  3. ↑ 3.0 3.1 "Paeonol: a bio-antimutagen isolated from a crude drug, moutan cortex". Agricultural and Biological Chemistry 51 (5): 1441–1442. 1987. 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. ↑ "Isolation of paeonol from Arisaema erubescens". Planta Medica 61 (6): 586–587. 1995. doi:10.1055/s-2006-959390. INIST:2920867. PMID 8824957. 
  6. ↑ 6.0 6.1 Miyazawa, Mitsuo; Shimamura, Hideo; Nakamura, Sei-Ichi; Kameoka, Hiromu (1996). "Antimutagenic Activity of (+)-β-Eudesmol and Paeonol fromDioscorea japonica". Journal of Agricultural and Food Chemistry 44 (7): 1647–1650. 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". Brain Research 1388: 141–7. doi:10.1016/j.brainres.2011.02.064. PMID 21377451. https://cloudfront.escholarship.org/dist/prd/content/qt1qs126j6/qt1qs126j6.pdf. 
  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 et al. (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. 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 et al. (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. doi:10.1016/j.molstruc.2019.06.050. Bibcode: 2019JMoSt1196..119P. 



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