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Year of first isolation: |
1994 |
| Formula: | C33H54O12 |
| Molecular weight: | 642 |
| Occurence in plants: |
Silene otites [Caryophyllaceae] »  ![Wikipedia: Silene otites [Caryophyllaceae]](/images/wikipedia.png)
Rhaponticum uniflorum [Asteraceae] »
Limnanthes douglasii [Limnanthaceae] »
Trisetum flavescens [Poaceae] »
Diploclisia glaucescens [Menispermaceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R)-2,3,6-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 | 66869428 | InChiKey
[ ChemIDPlus: search ] | APFXLSITBUTSAO-PGIMLHNSSA-N | | InChI | InChI=1S/C33H54O12/c1-29(2,41)9-8-24(37)32(5,42)23-7-11-33(43)17-12-19(35)18-13-21(44-28-27(40)26(39)25(38)22(15-34)45-28)20(36)14-30(18,3)16(17)6-10-31(23,33)4/h12,16,18,20-28,34,36-43H,6-11,13-15H2,1-5H3/t16-,18-,20-,21+,22+,23-,24?,25+,26-,27+,28+,30+,31+,32+,33+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 665 [M+Na]+, 647 [M+Na-H2O]+, 643 [M+H]+, 625 [M+H-H2O]+ | | HR-FAB-MS | [M+H] found 643.3658, calc. 643.3694 |
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| C5D5N | | 01 | 38.99 | | 02 | 68.34 | | 03 | 77.39 | | 04 | 30.80 | | 05 | 51.41 | | 06 | 203.56 | | 07 | 121.69 | | 08 | 166.75 | | 09 | 34.35 | | 10 | 38.73 | | 11 | 21.15 | | 12 | 32.03 | | 13 | 48.15 | | 14 | 84.30 | | 15 | 31.80 | | 16 | 21.57 | | 17 | 50.20 | | 18 | 17.99 | | 19 | 24.12 | | 20 | 77.03 | | 21 | 21.80 | | 22 | 77.73 | | 23 | 27.56 | | 24 | 42.73 | | 25 | 69.79 | | 26 | 30.12 | | 27 | 30.04 | | glu-01´ | 103.98 | | glu-02´ | 75.03 | | glu-03´ | 78.74 | | glu-04´ | 71.73 | | glu-05´ | 78.54 | | glu-06´ | 62.70 |
| CD3OD | | 01 | 36.1 | | 02 | 66.0 | | 03 | 76.4 | | 04 | 32.5 | | 05 | 51.9 | | 06 | 206.2 | | 07 | 122.1 | | 08 | 168.1 | | 09 | 35.0 | | 10 | 39.5 | | 11 | 21.5 | | 12 | 32.1 | | 13 | 48.4 | | 14 | 85.3 | | 15 | 31.7 | | 16 | 21.4 | | 17 | 50.5 | | 18 | 18.1 | | 19 | 24.2 | | 20 | 77.9 | | 21 | 21.1 | | 22 | 78.4 | | 23 | 27.4 | | 24 | 42.4 | | 25 | 71.7 | | 26 | 29.0 | | 27 | 29.7 | | glu-01´ | 102.7 | | glu-02´ | 75.2 | | glu-03´ | 77.9 | | glu-04´ | 71.3 | | glu-05´ | 78.0 | | glu-06´ | 62.7 |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.11 (dt, 12.3, 3.0, 3.0) | | 03-He | 4.31 (brq, 3.0) | | 04-Ha | | | 04-He | | | 05-H | 2.93 (dd, 13.3, 3.5) | | 07-H | 6.21 (d, 2.3) | | 09-Ha | 3.53 (m ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.98 (t, 9.0) | | 18-Me | 1.170 (s ) | | 19-Me | 0.858 (s ) | | 21-Me | 1.576 (s ) | | 22-H | 3.87 (dd, 9.6, 1.0) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.374 (s ) | | 27-Me | 1.374 (s ) | | H-1´ | 4.90 (d, 7.8) | | H-2´ | 4.03 (dd, 7.8, 9.0) | | H-3´ | 4.22 (t, 9.0, 9.0) | | H-4´ | 4.18 (t, 9.0, 9.0) | | H-5´ | 3.92 (ddd, 9.0, 2.2, 5.8) | | H-6a´ | 4.53 (dd, 11.7, 2.2) | | H-6b´ | 4.30 (dd, 11.7, 5.8) |
| CD3OD | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.02 (dt, 11.5, 5.0) | | 03-He | 4.13 (brq, 2.0) | | 04-Ha | | | 04-He | | | 05-H | 2.38 (m) | | 07-H | 5.80 (d, 2.5) | | 09-Ha | 3.15 (m) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.38 (m) | | 18-Me | 0.88 (s) | | 19-Me | 0.96 (s) | | 21-Me | 1.18 (s) | | 22-H | 3.30 (m) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.19 (s) | | 27-Me | 1.19 (s) | | H-1´ | 4.48 (d, 8.0) | | H-2´ | 3.20 (t, 8.5) | | H-3´ | 3.36 (t, 9.0) | | H-4´ | 3.33 (t, 9.8) | | H-5´ | 3.30 (m) | | H-6a´ | 3.69 (dd, 11.8, 5.2) | | H-6b´ | 3.87 (d, 10.0) |
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| M.P. | 297-300 °C | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3419 (-OH), 1660 (C=O), 1051 (C-O) ; | | UV (EtOH) λ max (log ε) | |
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| TLC | | | GLC | | | HPLC | RP-HPLC, column Spherisorb 5ODS2 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with 18% ACN-iPrOH (5:2) in 0.1% TFA in H2O, Ret 10.5 min (20E 13.9 min); column Separon SGX-C18 25 cm long, 8 mm i.d., flow-rate 4 ml.min-1, eluted with 40% MeOH in water, Ret 13.5 min. NP-HPLC, column Zorbax-ODS 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with cyclohexane-iPrOH-H2O (80:40:3), Ret 47.0 min (20E 10.1 min). LC on SEPHADEX LH20, solvent CHCl3-MeOH (1:1) |
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Drosophila melanogaster BII cell assay: EC50 = 1.3 x 10-5M |
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| Synthesis | PIS, J. et al. (1994) Tetrahedron 50, 9679-9690 |
 | | First isolation | PIS, J. et al. (1995) Eur. J. Entomol. 92, 41-50 |
| | Bioactivities | HARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 |
| | General | SARKER, S.D. et al. (1997) Phytochemistry 44, 513-521 |
| | General | SARKER, S.D. et al. (1998) Biochem. Syst. Ecol. 26, 135-137 |
| | First isolation | BÁTHORI, M. et al. (2000) Biomed. Chromatogr. 14, 464-467 |
| | First isolation | LI, X. et al. (2000) Shenyang Yaoke Daxue Xuebao 17, 260-262 |
| | Identification | JAYASINGHE, U.L.B et al. (2003) Tetrahedron Lett. 44, 8769-8771 |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 3-β-D-GLUCOSIDE
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