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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
ChemSpider
UNII
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
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
C 24 H 28 O 4
Molar mass
−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Riligustilide is a nonsteroidal phytoprogestogen that is found in Ligusticum chuanxiong [ 1] [ 2] agonist of the progesterone receptor (EC50 ≈ 81 μM).[ 1] 3,8-dihydrodiligustilide , is also a phytoprogestogen, but is almost 1,000-fold more potent in comparison (EC50 = 90 nM).[ 1]
See also
References
^ a b c 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 . ^ 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 .
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone 6,6-Difluoronorethisterone acetate 17α-Allyl-19-nortestosterone Allylestrenol Altrenogest Chloroethynylnorgestrel Cingestol Danazol Desogestrel Dienogest Ethinylandrostenediol
Ethisterone Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel esters (e.g., levonorgestrel butanoate )Lynestrenol Lynestrenol phenylpropionate Metynodiol Metynodiol diacetate Norelgestromin Norethisterone (norethindrone) Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tibolone Tigestol Tosagestin ; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione 19-Nordehydroepiandrosterone Bolandiol Bolandiol dipropionate Bolandione Dimethisterone Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethyldienolone Dimethyltrienolone Ethyldienolone Ethylestrenol (ethylnandrol) Methyldienolone Metribolone (R-1881) Methoxydienone (methoxygonadiene) Mibolerone Nandrolone Nandrolone esters (e.g., nandrolone decanoate , nandrolone phenylpropionate )Norethandrolone Normethandrone (methylestrenolone, normethandrolone, normethisterone) RU-2309 Tetrahydrogestrinone Trenbolone (trienolone) Trenbolone esters (e.g., trenbolone acetate , trenbolone enanthate )Trendione Trestolone Trestolone acetate MixedSPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor PAQR Tooltip Progestin and adipoQ receptor )
