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Year of first isolation: |
1986 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Serratula tinctoria [Asteraceae] »  ![Wikipedia: Serratula tinctoria [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
Gerardia savaglia [Zoanthidae] »
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(C(CC(C)(C)O)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]([C@H](CC(C)(C)O)O)O)O)O » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,4S)-2,3,4,6-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 102712-89-0 | | PubChem CID | 11071085 | InChiKey
[ ChemIDPlus: search ] | SLAXZVJCSMNNPH-MLXSIWSOSA-N | | InChI | InChI=1S/C27H44O8/c1-23(2,33)12-20(31)22(32)26(5,34)21-7-9-27(35)15-10-17(28)16-11-18(29)19(30)13-24(16,3)14(15)6-8-25(21,27)4/h10,14,16,18-22,29-35H,6-9,11-13H2,1-5H3/t14-,16-,18+,19-,20-,21-,22+,24+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 496 (M)+, 393 (0.4), 363 (17), 133 (5), 103 (4) | | HR-MS | | | FAB-MS m/z | 497 (M+H)+, 479, 461, 443, 425 |
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| D2O | | 01 | 36.3 | | 02 | | | 03 | | | 04 | | | 05 | 51.4 | | 06 | | | 07 | | | 08 | | | 09 | 35.1 | | 10 | 39.1 | | 11 | | | 12 | 31.8 | | 13 | 47.8 | | 14 | 86.1 | | 15 | | | 16 | | | 17 | 50.5 | | 18 | 18.3 | | 19 | 24.2 | | 20 | 79.8 | | 21 | 22.1 | | 22 | 78.5 | | 23 | | | 24 | 48.3 | | 25 | 72.5 | | 26 | 29.5 | | 27 | 29.6 |
| C5D5N* | | 21 | 23.22 (q ) | | 22 | 78.83 (d ) | | 23 | 68.88 (d ) | | 24 | 48.23 (t ) |
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| C5D5N | | 01-Ha | 1.93 | | 01-He | 2.12 | | 02-Ha | 4.18 (m, w1/2= 22) | | 03-He | 4.24 (br s, w1/2= 8) | | 04-Ha | 1.80 | | 04-He | 2.04 | | 05-H | 3.02 (dd, 13, 4) | | 07-H | 6.27 (d, 2.1) | | 09-Ha | 3.60 (m ) | | 11-Ha | 1.69 | | 11-He | 1.82 | | 12-Ha | 2.68 (ddd, 12, 12, 4.5) | | 12-He | 2.04 | | 15-Ha | 2.18 | | 15-Hb | 2.18 | | 16-Ha | 2.22* | | 16-Hb | 2.45* | | 17-H | 3.33 (dd, 8.5, 8.5) | | 18-Me | 1.14 (s ) | | 19-Me | 1.09 (s ) | | 21-Me | 1.77 (s ) | | 22-H | 3.75 (br s, w1/2= 4) | | 23-H | 4.80 (br d, 9.7) | | 24-Ha | 2.45** | | 24-Hb | 1.82** | | 26-Me | 1.44 (s ) | | 27-Me | 1.47 (s ) |
| D2O | | 01-Ha | 1.4 (t, 13) | | 01-He | 1.85 | | 02-Ha | 3.99 (m, w1/2= 22) | | 03-He | 4.07 (m, w1/2= 8) | | 04-Ha | 1.75 | | 04-He | 1.75 | | 05-H | 2.34 (t ) | | 07-H | 5.98 (d, 2.5) | | 09-Ha | 3.08 (m, w1/2= 22) | | 11-Ha | 1.75 | | 11-He | 1.85 | | 12-Ha | 1.75 | | 12-He | 1.95 | | 15-Ha | 2.05 (m ) | | 15-Hb | 1.65 | | 16-Ha | 1.85 | | 16-Hb | 1.9 | | 17-H | 2.56 (t ) | | 18-Me | 0.83 (s ) | | 19-Me | 1.00 (s ) | | 21-Me | 1.36 (s ) | | 22-H | 3.37 (s, w1/2= 3) | | 23-H | 4.25 (dd, 9.2, 2.5) | | 24-Ha | 1.9 | | 24-Hb | 1.7 | | 26-Me | 1.30 (s ) | | 27-Me | 1.32 (s ) |
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| M.P. | 143-146°C | | [α]D22 | + 52.3° (c 0.35 ; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (MeOH) λ max (log ε) | 243 (4.097) |
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| NP-HPLC | Column Zorbax-SIL9.4x250 mm, flow-rate 4 ml.min-1Solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v, Ret 45.2 min (20E 35.2 min). Solvent Cyclohexane-iPrOH-H2O 80:40:3 v/v/v, Ret 17.0 min (20E 13.4 min) | | HPTLC | | | TLC | | | GLC | | | RP-HPLC | Column Merck Lichrosorb RP-18, 7 ?m, 10x250 mm, flow-rate 5 ml.min-1 eluted with a gradient from MeOH-H2O 1:4 to pure MeOH in 11 min. Rt 10.5 min (20E 11 min) |
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Drosophila melanogaster BII cell assay: EC50 = 4.0 x 10-7M |
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| First isolation | GUERRIERO, A. et al. (1986) J. Chem. Soc., Chem. Commun., 40-41 |
 | | General | HONDA, T. et al. (1993) Tetrahedron Lett. (34), 8275-8278 |
| | General | TSUBUKI, M. et al. (1996) Tetrahedron 52, 14515-14532 |
| | General | BÁTHORI, M. et al. (1998) J. Nat. Prod. 61, 415-417 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
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Permanent link to this datasheet: GERARDIASTERONE
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