|
|
|
|
Year of first isolation: |
1967 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Podocarpus elatus [Podocarpaceae] »  ![Wikipedia: Podocarpus elatus [Podocarpaceae]](/images/wikipedia.png)
Lychnis flos-culculi [Caryophyllaceae] »
Silene nutans [Caryophyllaceae] »
Silene otites [Caryophyllaceae] »
Palisota schweinfurthii [Commelinaceae] »
|
| Occurence in animals: |
Manduca sexta [Lepidoptera] »
Hymenolepis diminuta [Platyhelminthes] »
|
|
![20,26-DIHYDROXYECDYSONE [= PODECDYSONE C]](images/ecdy/64.gif)
| |
| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(CO)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(CO)O)O)O)O » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 19458-46-9 | | PubChem CID | 21123946 | InChiKey
[ ChemIDPlus: search ] | RRCGNPRHZQPOOT-FFBSXHGNSA-N | | InChI | 1S/C27H44O8/c1-23(33,14-28)8-7-22(32)26(4,34)21-6-10-27(35)16-11-18(29)17-12-19(30)20(31)13-24(17,2)15(16)5-9-25(21,27)3/h11,15,17,19-22,28,30-35H,5-10,12-14H2,1-4H3/t15-,17-,19+,20-,21-,22+,23?,24+,25+,26+,27+/m0/s1 |
| |
| CI-MS (NH3) m/z | 514, 497 (MH)+, 479, 461, 443, 380, 363 (MH - C22-C27)+, 347, 345, 329. | | EI-MS m/z | 460 (M - 2x18)+, 442 (M - 3x18)+, 427, 409, 391, 363 (MH - C22-C27)+, 345, 133 (C22-C27)+, 115. | | HR-MS | |
|
|
| C5D5N (2 epimers) | | 01 | 37.95 a | | 02 | 68.05 b | | 03 | 68.12 b | | 04 | 31.68 c | | 05 | 51.37 | | 06 | 203.48 | | 07 | 121.62 | | 08 | 166.10 | | 09 | 34.40 | | 10 | 38.62 | | 11 | 21.40 | | 12 | 32.41 c | | 13 | 48.08 | | 14 | 84.18 | | 15 | 31.96 c | | 16 | 21.66 | | 17 | 50.07 | | 18 | 17.35 | | 19 | 24.52 d | | 20 | 76.87 | | 21 | 21.09 | | 22 | 77.65 | | 23 | 26.76 | | 24 | 37.55 a | | 25 | 72.66 | | 26 | 70.79 | | 27 | 24.41 |
| C5D5N (2 epimers) | | 01 | 37.95 e | | 02 | 68.05 f | | 03 | 68.14 f | | 04 | 31.70 g | | 05 | 51.39 | | 06 | 203.50 | | 07 | 121.62 | | 08 | 166.12 | | 09 | 34.45 | | 10 | 38.64 | | 11 | 21.45 | | 12 | 32.44 g | | 13 | 48.08 | | 14 | 84.18 | | 15 | 31.98 g | | 16 | 21.70 | | 17 | 50.09 | | 18 | 17.86 | | 19 | 24.76 h | | 20 | 76.87 | | 21 | 21.09 | | 22 | 77.68 | | 23 | 26.70 | | 24 | 37.52 e | | 25 | 72.60 | | 26 | 70.62 | | 27 | 24.43 h |
|
| C5D5N (2 epimers) | | 01-He | | | 02-Ha | 4.19 (m) | | 03-He | 4.23 (br s) | | 04-Ha | | | 04-He | | | 05-H | 3.01 a | | 07-H | 6.25 (d, 2.4) | | 09-Ha | 3.58 (m) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.03 a | | 18-Me | 1.204 (s) | | 19-Me | 1.06 (s) | | 20-H | | | 21-Me | 1.58 (s) | | 22-H | 3.92 (br d, 10.3) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 3.87 b + 3.88 c | | 27-Me | 1.47(s) | | OH | 6.29 (s) |
| C5D5N (2 epimers) | | 01-He | | | 02-Ha | 4.19 (m) | | 03-He | 4.23 (br s) | | 04-Ha | | | 04-He | | | 05-H | 3.01 a | | 07-H | 6.25 (d, 2.4) | | 09-Ha | 3.58 (m) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.03 a | | 18-Me | 1.204 (s) | | 19-Me | 1.06 (s) | | 20-H | | | 21-Me | 1.58 (s) | | 22-H | 3.92 (br d, 10.3) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 3.87 b + 3.88 c | | 27-Me | 1.47(s) | | OH | 6.29 (s) |
|
| |
| M.P. | 149-153 °C ; | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3486 (OH), 1652 (cyclohexenone). | | UV (EtOH) λ max (log ε) | 242 (4.041) ; |
| |
| TLC | Rf 0.44 (EtOAc-EtOH-H2O, 8:2:1) (20E 0.61); Rf 0.25 (CHCl3-MeOH-Me2CO, 6:2:1) (20E 0.47); Rf 0.17 (CHCl3-96% EtOH, 7:3) (20E 0.35). | | GLC | Retention time 18.25 min, 25 m x 0.22 mm fused silica column, 0.1 ?m film of BP-1 oven temperature 50°C at injection raised immediatelly to 200°C than programmed at 8°C.min-1 to 320°C than isothermal; carrier gas He at 100 ml.min-1 (20E: retention time 12 min). | | HPLC | 1- Retention time 43.9 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min) 2- Retention time 4.1 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN-1? TFA in H2O, 23:77 v/v, flow-rate 1 ml.min-1] (20E 5.5 min) |
| |
Drosophila melanogaster BII cell assay: EC50 = 7.3 x 10-6M | Calliphora assay: 10% (20-hydroxyecdysone = 100%) | Musca assay: 7-10% (20-hydroxyecdysone = 100%) |
| |
| First isolation | THOMPSON, M.J. et al. (1967) Chem. Commun., 650-653 |
 | | First isolation | THOMPSON, M.J. et al. (1973) Experientia 29, 782 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | MENDIS, A.H.W. et al. (1983) Mol. Biochem. Parasitol. 9, 209-226 |
| | General | EVERSHED, R.P. et al. (1987) J. Chromatogr. 390, 357-369 |
| | General | GIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 293-302 |
| | General | KUSAMBA, C. et al. (1995) Fitoterapia LXVI, 175-178 |
| | General | SUKSAMRARN, A. et al. (1998) Tetrahedron 54, 14565-14572 |
| | Bioactivities | DINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 |
|
| |
Permanent link to this datasheet: 20,26-DIHYDROXYECDYSONE [= PODECDYSONE C]
|
|
