Petasin

  • CAT Number: M016872
  • CAS Number: 26577-85-5
  • Molecular Formula: C20H28O3
  • Molecular Weight: 316.441
  • Purity: ≥95%
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Petasin is a natural chemical compound found in plants of the genus Petasites. Chemically, it is classified as a sesquiterpene and is the ester of petasol and angelic acid.

Petasin is believed to be responsible, at least in part, for the anti-inflammatory effects of Common Butterbur (Petasites hybridus) extracts.

Catalog Number M016872
CAS Number 26577-85-5
Synonyms

(Z)-2-Methyl-2-butenoic acid (1R)-1,2,3,4,6,7,8,8a-octahydro-1β,8aβ-dimethyl-7α-(1-methylethenyl)-6-oxonaphthalen-2α-yl ester;(Z)-2-Methyl-2-butenoic acid [(3S)-3α-isopropenyl-4aβ,5β-dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-oxonaphthalene]-6α-yl ester;(

Molecular Formula

C20H28O3

Purity 95%
IUPAC Name [(1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-prop-1-en-2-yl-1,2,3,4,7,8-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate
InChI InChI=1S/C20H28O3/c1-7-13(4)19(22)23-18-9-8-15-10-17(21)16(12(2)3)11-20(15,6)14(18)5/h7,10,14,16,18H,2,8-9,11H2,1,3-6H3/b13-7-/t14-,16-,18+,20+/m0/s1
InChIKey ISTBXSFGFOYLTM-NZEDGPFZSA-N
SMILES CC=C(C)C(=O)OC1CCC2=CC(=O)C(CC2(C1C)C)C(=C)C
Reference

1: Steiert SA, Zissler UM, Chaker AM, Esser-von-Bieren J, Dittlein D, Guerth F,
Jakwerth CA, Piontek G, Zahner C, Drewe J, Traidl-Hoffmann C, Schmidt-Weber CB,
Gilles S. Anti-inflammatory effects of the petasin phyto drug Ze339 are mediated
by inhibition of the STAT pathway. Biofactors. 2017 May 6;43(3):388-399. doi:
10.1002/biof.1349. Epub 2017 Jan 31. PubMed PMID: 28139053.
<br>

2: Lee KP, Kang S, Noh MS, Park SJ, Kim JM, Chung HY, Je NK, Lee YG, Choi YW, Im
DS. Therapeutic effects of s-petasin on disease models of asthma and peritonitis.
Biomol Ther (Seoul). 2015 Jan;23(1):45-52. doi: 10.4062/biomolther.2014.069. Epub
2015 Jan 1. PubMed PMID: 25593643; PubMed Central PMCID: PMC4286749.
<br>

3: Wang ZH, Hsu HW, Chou JC, Yu CH, Bau DT, Wang GJ, Huang CY, Wang PS, Wang SW.
Cytotoxic effect of s-petasin and iso-s-petasin on the proliferation of human
prostate cancer cells. Anticancer Res. 2015 Jan;35(1):191-9. PubMed PMID:
25550551.
<br>

4: Adachi Y, Kanbayashi Y, Harata I, Ubagai R, Takimoto T, Suzuki K, Miwa T,
Noguchi Y. Petasin activates AMP-activated protein kinase and modulates glucose
metabolism. J Nat Prod. 2014 Jun 27;77(6):1262-9. doi: 10.1021/np400867m. Epub
2014 May 28. PubMed PMID: 24871354.
<br>

5: Wang GJ, Lin YL, Chen CH, Wu XC, Liao JF, Ren J. Cellular calcium regulatory
machinery of vasorelaxation elicited by petasin. Clin Exp Pharmacol Physiol. 2010
Mar;37(3):309-15. doi: 10.1111/j.1440-1681.2009.05283.x. Epub 2009 Aug 28. PubMed
PMID: 19719750.
<br>

6: Shih CH, Huang TJ, Chen CM, Lin YL, Ko WC. S-Petasin, the Main Sesquiterpene
of Petasites formosanus, Inhibits Phosphodiesterase Activity and Suppresses
Ovalbumin-Induced Airway Hyperresponsiveness. Evid Based Complement Alternat Med.
2011;2011:132374. doi: 10.1093/ecam/nep088. Epub 2011 Feb 10. PubMed PMID:
19641087; PubMed Central PMCID: PMC3094704.
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7: Sheykhzade M, Smajilovic S, Issa A, Haunso S, Christensen SB, Tfelt-Hansen J.
S-petasin and butterbur lactones dilate vessels through blockage of voltage gated
calcium channels and block DNA synthesis. Eur J Pharmacol. 2008 Sep
28;593(1-3):79-86. doi: 10.1016/j.ejphar.2008.07.004. Epub 2008 Jul 10. PubMed
PMID: 18655785.

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