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Year of first isolation: |
1968 |
| Formula: | C29H48O7 |
| Molecular weight: | 508 |
| Occurence in plants: |
Cyathula capitata [Amaranthaceae] »  ![Wikipedia: Cyathula capitata [Amaranthaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CCC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)C(C)CO | 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)([C@@H](C[C@H](C(CO)C)CC)O)O)O)C)C » 
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)([C@@H](C[C@H](C(CO)C)CC)O)O)O)C)C »
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)([C@@H](C[C@H](C(CO)C)CC)O)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R,5R)-5-ethyl-2,3,7-trihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 20853-88-7 | | PubChem CID | 101297611 | InChiKey
[ ChemIDPlus: search ] | GTRXMTZSWNWUAX-YAUYKCKZSA-N | | InChI | InChI=1S/C29H48O7/c1-6-17(16(2)15-30)11-25(34)28(5,35)24-8-10-29(36)19-12-21(31)20-13-22(32)23(33)14-26(20,3)18(19)7-9-27(24,29)4/h12,16-18,20,22-25,30,32-36H,6-11,13-15H2,1-5H3/t16?,17-,18+,20+,22-,23+,24+,25-,26-,27-,28-,29-/m1/s1 |
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| CI-MS (NH3) m/z | 363 (M - C22-C29)+, 345, 327, 145 (C22-C29)+, 127, 109. | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| D2O | | 01 | 38.3; 38.6 | | 02 | 70.2; 70.2 | | 03 | 70.1; 70.1 | | 04 | 34.1; 34.0 | | 05 | 53.3; 53.1 | | 06 | 211.4; n.d. | | 07 | 124.1; 123.7 | | 08 | n.d.; n.d. | | 09 | 36.7; 36.4 | | 10 | 41.0; 40.8 | | 11 | 23.0; 22.8 | | 12 | 33.9; 33.8 | | 13 | 50.3; 50.0 | | 14 | 88.1; 87.4 | | 15 | 33.4; 33.0 | | 16 | 22.4; 22.4 | | 17 | 52.1; 52.0 | | 18 | 19.9; 19.8 | | 19 | 25.9; 25.8 | | 20 | 81.0; 80.6 | | 21 | 22.4; 22.3 | | 22 | 78.8; 76.8 | | 23 | 35.4; 33.2 | | 24 | 41.4; 39.0 | | 25 | 40.0; 38.3 | | 26 | 68.0; 68.4 | | 27 | 18.8; 13.7 | | 28 | 25.1; 25.5 | | 29 | 14.2; 14.0 |
| CD3OD | | 01 | 37.36 | | 02 | 68.70 | | 03 | 68.52 | | 04 | 32.86 | | 05 | 51.79 | | 06 | 206.44 | | 07 | 122.14 | | 08 | 167.94 | | 09 | 35.10 | | 10 | 39.26 | | 11 | 21.53 | | 12 | 32.52 | | 13 | 49.0* | | 14 | 85.21 | | 15 | 31.79 | | 16 | 21.47 | | 17 | 50.34 | | 18 | 18.06 | | 19 | 24.41 | | 20 | 77.96 | | 21 | 20.90 | | 22 | 75.71 | | 23 | 32.02 | | 24 | 37.85 | | 25 | 37.60 | | 26 | 66.75 | | 27 | 11.51 | | 28 | 25.40 | | 29 | 12.29 |
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| CD3OD | | 01-Ha | 1.43 (dd, 13.4, 12.0) | | 01-He | 1.79 (dd, 13.4, 4.2) | | 02-Ha | 3.83 (ddd, 12.0, 4.2, 3.0) | | 03-He | 3.95 (q, 3, 3, 3) | | 04-Ha | 1.70-1.75 | | 04-He | 1.70-1.75 | | 05-H | 3.38 (dd, 12.6, 4.5) | | 07-H | 5.81 (d, 2.6) | | 09-Ha | 3.15 (ddd, 11.5, 7, 2.6) | | 11-Ha | 1.70 | | 11-He | 1.81 | | 12-Ha | 2.11 (td, 13, 13, 5) | | 12-He | 1.88 | | 15-Ha | 1.96 | | 15-Hb | 1.61 | | 16-Ha | 1.75 | | 16-Hb | 2.00 | | 17-H | 2.34 (dd, 9.8, 8.4) | | 18-Me | 0.894 (s) | | 19-Me | 0.968 (s) | | 21-Me | 1.179 (s) | | 22-H | 3.45 (dd, 10.4, 2.3) | | 23-Ha | 1.21 | | 23-Hb | 1.21 | | 24-Hb | 1.68 | | 25-H | 1.85 | | 26-H | 3.50 (dd, 11.0, 7.3) | | 27-Me | 0.786 (d, 7.0) | | 28-Ha,b | 1.51, 1.28 | | 29-Me | 0.935 (t, 6.4, 6.4) |
| D2O | | 01-Ha | 1.38; 1.38 | | 01-He | 1.88; 1.88 | | 02-Ha | 3.99 (w1/2=22); 3.99 (w1/2=22) | | 03-He | 4.07 (w1/2=8); 4.07 (w1/2=8) | | 04-Ha | 1.75; 1.75 | | 04-He | 1.75; 1.75 | | 05-H | 2.34 (t); 2.34 (t) | | 07-H | 5.97 (d, 2); 5.97 (d, 2) | | 09-Ha | 3.11 (w1/2=22); 3.11 (w1/2=22) | | 11-Ha | 1.73; 1.73 | | 11-He | 1.86; 1.86 | | 12-Ha | 1.99*; 1.99* | | 12-He | 1.96*, 1.96* | | 15-Ha | 1.65; 1.64 | | 15-Hb | 2.05; 2.05 | | 16-Ha | 1.89**; 1.89** | | 16-Hb | 1.80**; 1.80 | | 17-H | 2.32 (m); 2.30 (m) | | 18-Me | 0.867 (s); 0.867 (s) | | 19-Me | 1.000 (s); 1.000 (s) | | 21-Me | 1.230 (s); 1.222 (s) | | 22-H | 3.54 (d, 10); 3.56 (d, 10) | | 23-Ha | 1.36; 1.29 | | 23-Hb | 1.42; 1.24 | | 24-Ha | 1.50; 1.56 | | 25-H | 1.82; 1.88 | | 26-Ha | 3.39 (dd, 10.8, 8.3); 3.46 (dd, 10.8, 7.2) | | 26-Hb | 3.65 (dd, 10.8, 5); 3.55 (m) | | 27-Me | 0.932 (d, 6.8); 0.809 (d, 6.8) | | 28-Ha | 1.40; 1.30 | | 28-Hb | 1.40; 1.52 | | 29-Me | 0.913 (t, 7.1); 0.896 (t, 7.4) |
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| M.P. | 210-211 °C | | [α]D20 | | | IR (KBr) ν max (cm-1) | -- (OH), 1650 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 244 ; |
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| HPTLC | | | TLC | | | GLC | | | HPLC | | | NP-HPLC | Kromasil column (250 x 4.6 mm i.d.), solvent dichloromethane-isopropanol-water (125:30:1.5), flow rate 1 ml/min, ret. 15.6 and 12.0 min (20E: 27.8 min) | | RP-HPLC | Spherisorb 5ODS2 column (250 x 4.6 mm i.d.), solvent methanol-water (45:55), flow rate 0.7 ml/min, ret. 24.9 and 31,0 min (20E: 10,9 min) |
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Drosophila melanogaster BII cell assay: EC50 = 5.6 x 10-7M | Sarcophaga assay: highly active |
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| First isolation | TAKEMOTO, T. et al. (1968) Tetrahedron Lett. 4953-4956 |
 | | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | Bioactivities | DINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 |
| | General | SNOGAN, E. et al. (2007) Phytochemical Analysis 18, 441-450 |
| | Identification | BUDĚŠÍNSKÝ, M. et al. (2008) Steroids 73, 502-514 |
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Permanent link to this datasheet: AMARASTERONE A
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