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Year of first isolation: |
2008 |
| Formula: | C33H54O11 |
| Molecular weight: | 626 |
| Occurence in plants: |
Leuzea carthamoides [Asteraceae] »  ![Wikipedia: Leuzea carthamoides [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)OC5C(C(C(C(O5)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)([C@@H](CCC(C)C)O[C@@H]1OC([C@H](C(C1O)O)O)CO)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14R,17S)-2,3,14-trihydroxy-17-[(2R,3R)-2-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101851583 | InChiKey
[ ChemIDPlus: search ] | UPMZPXAMHPZSQX-WIKHOFDESA-N | | InChI | InChI=1S/C33H54O11/c1-16(2)6-7-25(44-29-28(40)27(39)26(38)23(15-34)43-29)32(5,41)24-9-11-33(42)18-12-20(35)19-13-21(36)22(37)14-30(19,3)17(18)8-10-31(24,33)4/h12,16-17,19,21-29,34,36-42H,6-11,13-15H2,1-5H3/t17-,19-,21+,22-,23+,24-,25+,26+,27-,28+,29-,30+,31+,32+,33-/m0/s1 |
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| ESI-MS/MS m/z | 627 [M+H]+, 609 [M+H-H2O]+, 591 [M+H-2H2O]+, 573 [M+H-3H2O]+, 465 [M+H-C6H10O5]+, 447 [M+H-H2O-C6H10O5]+, 429 [M+H-2H2O-C6H10O5]+, 411 [M+H-3H2O-C6H10O5]+, 347, 329, 303, 145 | | HR-ESI-MS m/z | 627.3758 [M+H]+ (calculated for C33H55O11: 627.3758) |
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| CD3OD | | 01 | 37.22 | | 02 | 68.67 | | 03 | 68.39 | | 04 | 32.90 | | 05 | 50.98 | | 06 | 206.22 | | 07 | 123.14 | | 08 | 167.38 | | 09 | 37.25 | | 10 | 39.21 | | 11 | 22.20 | | 12 | 41.90 | | 13 | 52.77 | | 14 | 85.47 | | 15 | 41.14 | | 16 | 24.43 | | 17 | 57.30 | | 18 | 19.37 | | 19 | 24.67 | | 20 | 77.07 | | 21 | 21.83 | | 22 | 90.44 | | 23 | 31.00 | | 24 | 36.44 | | 25 | 29.36 | | 26 | 22.84 | | 27 | 23.25 | | [Glu] 1´ | 105.95 | | [Glu] 2´ | 75.27 | | [Glu] 3´ | 77.94 | | [Glu] 4´ | 77.90 | | [Glu] 5´ | 71.41 | | [Glu] 6´ | 62.31 |
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| CD3OD | | 01-Ha | 1.43 (dd, 13.2, 12.0) | | 01-He | 1.80 (dd, 13.3, 4.2) | | 02-Ha | 3.86 (ddd, 12.0, 4.2, 3.0) | | 03-He | 3.94 (q, 3, 3, 3) | | 04-Ha | 1.73 | | 04-He | 1.60 | | 05-H | 2.36 (dd, 13.2, 4.0) | | 07-H | 6.32 (dd, 2.4, 0.8) | | 09-Ha | 2.85 (m) | | 11-Ha | 1.66 | | 11-He | 1.79 | | 12-Ha | 1.75 | | 12-He | 1.69 | | 15-Ha | 2.28 | | 15-Hb | 1.43 | | 16-Ha | 1.86 | | 16-Hb | 2.08 | | 17-H | 1.91 | | 18-Me | 1.26 (s) | | 19-Me | 0.94 (s) | | 21-Me | 1.32 (s) | | 22-H | 3.58 (dd, 10.0, 1.5) | | 23-Ha | 1.57 | | 23-Hb | 1.48 | | 24-Ha | 1.74 | | 24-Hb | 1.24 | | 25-H | 1.56 | | 26-Me | 0.93 (d, 6.8) | | 27-Me | 0.93 (d, 6.8) | | [Glu] 1' | 4.34 (d, 7.8) | | [Glu] 2' | 3.26 (dd, 7.8, 8.8) | | [Glu] 3' | ~3.36 (m) | | [Glu] 4' | ~3.36 (m) | | [Glu] 5' | ~3.36 (m) | | [Glu] 6'a | 3.69 (dd, 11.8, 5.5) | | [Glu] 6'b | 3.87 (dd, 11.8, 1.8) |
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| M.P. | °C ; | | [α]D20 | + 59.2 ° (c 0.03; EtOH) | | IR (KBr) ν max (cm-1) | 3413 (OH), 1652 (C=O), 1099, 1071, 1056, 1030 (C-O) | | UV (MeOH) λ max (log ε) | |
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| HPLC | | | NP-HPLC | column Silasorb 600 (5 micro m, 250 x 4 mm) solvent dichloromethane-isopropanol-water (84:15:1), flow-rate 0.8 ml/min . Retention time 88.8 min (20E 90.9 min); and two other solvent systems. | | RP-HPLC | column Separon SGX C-18 (5 micro m, 250 x 4 mm), solvent methanol-water (linear grad of 10-70%), flow-rate 0,6 ml/min. Retention time 47.3 min (20E 34.2 min); | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 14-EPI-PONASTERONE A 22-GLUCOSIDE
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