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Year of first isolation: |
1986 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Silene nutans [Caryophyllaceae] »  ![Wikipedia: Silene nutans [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
Pycnogonum litorale [pantopod] »
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(CCCC(C)(CO)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(CCCC(CO)(C)O)O)O)C)C » 
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1C2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(CCC[C@@](CO)(C)O)O)O)C)C »
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1C2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(CCC[C@](CO)(C)O)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,10R,13R,14S,17R)-2,3,14-trihydroxy-10,13-dimethyl-17-(2,6,7-trihydroxy-6-methylheptan-2-yl)-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 129674882 | InChiKey
[ ChemIDPlus: search ] | ZFLUUBHIYYRUJA-ASBKUYEXSA-N | | InChI | InChI=1S/C27H44O7/c1-23(32,15-28)8-5-9-26(4,33)22-7-11-27(34)17-12-19(29)18-13-20(30)21(31)14-24(18,2)16(17)6-10-25(22,27)3/h12,16,18,20-22,28,30-34H,5-11,13-15H2,1-4H3/t16?,18-,20+,21-,22+,23?,24+,25+,26?,27+/m0/s1 |
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| CI-MS (NH3) m/z | 498 (M+H+NH3)+, (481) MH)+, 463, 445, 427, 409, 320, 303 ... | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | | | 28 | | | 29 | |
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| D2O | | 01-Ha | | | 01-Hb | | | 02-Ha | 3.94 (m, w1/2=21) | | 03-He | 3.97 (m, w1/2=8) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.97 (d, 2.5) | | 09-Ha | 3.09 (m ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.30 | | 18-Me | 0.82 (s ) | | 19-Me | 1.00 (s ) | | 21-Me | 1.30 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-CH2OH | 3.45 (s ) | | 27-Me | 1.14, 1.15 (2 isomers) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | NP-TLC silica, Rf 0.49 (EtOAC-EtOH-H2O 8:2:1); Rf 0.30 (CHCl3-MeOH-Me2CO 6:2:1). | | GLC | | | HPLC | NP-HPLC (Merk Lichrosorb Si 60) Ret 39.4 ml (solvent CH2Cl22-iPrOH-H2O 125:30:2) (20-hydroxyecdysone 27.6 ml). RP-HPLC, (Supersphere RP18); Ret. 10.8 min (solvent ACN-1? TFA/H2O 16:84 (v/v), isocratic for 10 min then linear gradient to 40:60 in 25 min) (20-hydroxyecdysone 7.3 min). |
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Drosophila melanogaster BII cell assay: EC50 = 5.3 x 10-6M |
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| First isolation | BÜCKMANN, D. et al. (1986) J. Comp. Physiol., B 156, 759-765 |
 | | General | GIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 |
| | Bioactivities | DINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 |
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Permanent link to this datasheet: 22-DEOXY-20,26-DIHYDROXYECDYSONE
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