3,8-Dihydrodiligustilide

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

3,8-Dihydrodiligustilide
Clinical data
Other names(3Z')-(3a'R,6'R,3R,6R,7R)-3,8-Dihydro-6.6',7.3a'-diligustilide[1]
Identifiers
IUPAC name
  • (1S,2S,6Z,10S,11S)-16-Butyl-6-butylidene-5,15-dioxapentacyclo[9.5.2.01,13.02,10.03,7]octadeca-3(7),12-diene-4,14-dione
PubChem CID
Chemical and physical data
FormulaC24H30O4
Molar mass382.500 g·mol−1
3D model (JSmol)
SMILES
  • CCCCC1[C@]23CC[C@H](C=C2C(=O)O1)[C@H]4[C@@H]3C5=C(CC4)/C(=C/CCC)/OC5=O
InChI
  • InChI=1S/C24H30O4/c1-3-5-7-18-16-10-9-15-14-11-12-24(21(15)20(16)23(26)27-18)17(13-14)22(25)28-19(24)8-6-4-2/h7,13-15,19,21H,3-6,8-12H2,1-2H3/b18-7-/t14-,15+,19?,21-,24+/m1/s1
  • Key:YTEUTQUNVHWZOR-LGNHLWLRSA-N

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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