20-HYDROXYECDYSONE
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Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 5459840
Name
20-HYDROXYECDYSONE
Also reported as
BETA-ECDYSONE
IUPAC name
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
SMILES
O=C1\C=C3/[C@@H]([C@]2(C[C@H](O)[C@H](O)C[C@@H]12)C)CC[C@]4([C@@]3(O)CC[C@@H]4[C@](O)(C)[C@H](O)CCC(O)(C)C)C
Molecular formula
C27H44O7
Molecular weight
480.64 g/mol
Monoisotopic mass
480.3087 Da
Chemical classification: NPClassifier (Kim et al., 2021)
| Plant | Plant part | Amount | Reference |
|---|---|---|---|
| Ajuga chamaepitys (L.) Schreb. | - | 38 ppm |
Jim Duke's personal files.
|
| Ajuga reptans L. | - | - |
J.S. Glasby Dict.Pls Containing 2ndary Metabolite. 1991.
|
| Helleborus foetidus L. subsp. foetidus | - | - |
Hardman, R., Benjamin, T.V. (1976). The co-occurrence of ecdysones with bufadienolides and steroidal saponins in the genus Helleborus. Phytochemistry, 15, 1515-1516 doi:10.1016/s0031-9422(00)88927-x
|
| Pteridium aquilinum (L.) Kuhn subsp. aquilinum | leaf | - |
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
|
| Serratula tinctoria L. subsp. monticola (Boreau) Berher | - | - |
Maria, B., Huba, K., Szolnoki, C., Imre, M. (1999). Components of Serratula species; screening for ecdysteroid and inorganic constituents of some Serratula plants. Acta Pharm Hung, 69(2), 72-76
|
| Serratula tinctoria L. subsp. monticola (Boreau) Berher | aerial parts | - |
Bathori, M., Mathe, I., Girault, J.P., Kalasz, H., Lafont, R. (1998). Isolation and structural elucidation of two plant ecdysteroids, gerardiasterone and 22-epi-20-hydroxyecdysone. J Nat Prod, 61(3), 415-417 doi:10.1021/np970124y
|
| Serratula tinctoria L. subsp. monticola (Boreau) Berher | aerial parts | - |
Corio-costet, M.F., Chapuis, L., Mouillet, J.F., Delbecque, J.P. (1993). Sterol and ecdysteroid profiles of Serratula tinctoria (L.): plant and cell cultures producing steroids. Insect Biochem Mol Biol, 23(1), 175-180 doi:10.1016/0965-1748(93)90098-d
|
| Serratula tinctoria L. subsp. monticola (Boreau) Berher | cell culture | - |
Corio-costet, M.F., Chapuis, L., Mouillet, J.F., Delbecque, J.P. (1993). Sterol and ecdysteroid profiles of Serratula tinctoria (L.): plant and cell cultures producing steroids. Insect Biochem Mol Biol, 23(1), 175-180 doi:10.1016/0965-1748(93)90098-d
|
| Serratula tinctoria L. subsp. monticola (Boreau) Berher | leaf | - |
Bathori, M., Mathe, I., Guttman, A. (1998). Determination of 20-hydroxyecdysone content by thin layer chromatography and micellar electrokinetic chromatography. Chromatographia, 48(1/2), 145-148 doi:10.1007/bf02467531
|
| Serratula tinctoria L. subsp. monticola (Boreau) Berher | root | - |
Corio-costet, M.F., Chapuis, L., Mouillet, J.F., Delbecque, J.P. (1993). Sterol and ecdysteroid profiles of Serratula tinctoria (L.): plant and cell cultures producing steroids. Insect Biochem Mol Biol, 23(1), 175-180 doi:10.1016/0965-1748(93)90098-d
|
| Serratula tinctoria L. subsp. monticola (Boreau) Berher | root | - |
Rudel, D., Bathori, M., Gharbi, J., Girault, J.P., Racz, I., Melis, K., Szendrei, K., Lafont, R. (1992). New ecdysteroids from Serratula tinctoria. Planta Med, 58(4), 358-364 doi:10.1055/s-2006-961485
|
| Silene italica (L.) Pers. subsp. italica | aerial parts | - |
Meng, Y.H., Whiting, P., Zibareva, L., Bertho, G., Girault, J.P., Lafont, R., Dinan, L. (2001). Identification and quantitative analysis of the phytoecdysteroids in Silene species (Caryophyllaceae) by high-performance liquid chromatography. novel ecdysteroids from S.pseudotites. J Chromatogr A, 935(1/2), 309-319 doi:10.1016/s0021-9673(01)00893-7
|
| Silene nutans L. subsp. nutans | - | - |
Girault, J.P., Bathori, M., Varga, E., Szendrei, K., Lafont, R. (1990). Isolation and identification of new ecdysteroids from the Caryophyllaceae. J Nat Prod, 53(2), 279-293 doi:10.1021/np50068a002
|
| Silene nutans L. subsp. nutans | aerial parts | - |
Baltaev, U., Rashkes, Y.V., Darmograi, V.N., Belov, Y.P., Abubakirov, N.K. (1985). Phytoecdysteroids of Silene nutans. ii. 22-deoxyecdysterone and features of its mass spectrum. Chem Nat Comp, 21(1), 59-62 doi:10.1007/bf00574250
|
| Silene nutans L. subsp. nutans | aerial parts | - |
Ramazanov, N.S., Sultanov, S.A., Saatov, Z., Nigmatullaev, A.M. (1997). Phytoecdysteroids of plants of the Silene genus and the dynamics of their accumulation. Chem Nat Comp, 33(5), 558-562 doi:10.1007/bf02254804
|