Riligustilide

Riligustilide is a nonsteroidal phytoprogestogen that is found in Ligusticum chuanxiong.[1][2] It is a very weak agonist of the progesterone receptor (EC50 ≈ 81 μM).[1] Another compound in the plant, 3,8-dihydrodiligustilide, is also a phytoprogestogen, but is almost 1,000-fold more potent in comparison (EC50 = 90 nM).[1]

Riligustilide
Names
IUPAC name
(3S,3′Z,5′aR,6′S,7′aS)-3′-Butylidene-6′-propylspiro[4,5-dihydro-2-benzofuran-3,7′-5,5a,6,7a-tetrahydro-4H-cyclobuta[g][2]benzofuran]-1,1′-dione
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C24H28O4/c1-3-5-11-19-16-13-12-14-17(8-4-2)24(21(14)20(16)23(26)27-19)18-10-7-6-9-15(18)22(25)28-24/h6,9,11,14,17,21H,3-5,7-8,10,12-13H2,1-2H3/b19-11-/t14-,17+,21+,24-/m1/s1
    Key: TYSOMZQRYGBSKN-DRQJQJQISA-N
SMILES
  • CCC/C=C\1/C2=C([C@@H]3[C@H](CC2)[C@@H]([C@@]34C5=C(C=CCC5)C(=O)O4)CCC)C(=O)O1
Properties
Chemical formula
 C24H28O4
Molar mass 380.484 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

See also

References
  1. Lim LS, Shen P, Gong YH, Yong EL (2006). "Dimeric progestins from rhizomes of Ligusticum chuanxiong". Phytochemistry. 67 (7): 728–34. doi:10.1016/j.phytochem.2006.01.024. PMID 16516938.
  2. Ahmed, H.M.M.; Yeh, J.Y.; Lin, W.J.; Forsberg, N.E.; Cheng, W.T.K.; Ou, B.R (2014). "Validation of a luciferase bioassay to detect the progestative activity in gilts whose estrus was induced by an uterotonic herb (Ligusticum chuanxiong)". Livestock Science. 163: 159–164. doi:10.1016/j.livsci.2014.02.012. ISSN 1871-1413.
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