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]

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<i>N</i>-Arachidonylglycine Chemical compound

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Lunamarine Chemical compound

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Superoxide dismutase mimetics Synthetic compounds

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Forsythoside B

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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. PMID   31030097 doi : 10.1016/j.intimp.2019.04.033
  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 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" (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.