Petasin

Last updated
Petasin
Petasin structure.svg
Names
IUPAC name
8-Oxo-7α-eremophila-9,11-dien-3α-yl (2Z)-2-methylbut-2-enoate
Systematic IUPAC name
(1R,2R,7S,8aR)-1,8a-Dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate
Other names
Petasol butenoate; O-Angeloylsencathenone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • 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
    Key: ISTBXSFGFOYLTM-NZEDGPFZSA-N
  • InChI=1/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
    Key: ISTBXSFGFOYLTM-NZEDGPFZBZ
  • O=C2/C=C1/CC[C@@H](OC(=O)\C(=C/C)C)[C@@H]([C@]1(C[C@H]2\C(=C)C)C)C
Properties
C20H28O3
Molar mass 316.441 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. [1]

A 2021 study reported that petasin can inhibit tumor growth and metastasis in an animal model of cancer. [2]

References

  1. ↑ Thomet, O; Wiesmann, UN; Schapowal, A; Bizer, C; Simon, HU (2001). "Role of petasin in the potential anti-inflammatory activity of a plant extract of petasites hybridus". Biochemical Pharmacology . 61 (8): 1041–7. doi:10.1016/S0006-2952(01)00552-4. PMID   11286996.
  2. ↑ Heishima, Kazuki; Sugito, Nobuhiko; Soga, Tomoyoshi; Nishikawa, Masashi; Ito, Yuko (2021). "Petasin potently inhibits mitochondrial complex I–based metabolism that supports tumor growth and metastasis". The Journal of Clinical Investigation . 131 (17) e139933. doi: 10.1172/JCI139933 . PMC   8409585 .


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