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Year of first isolation: |
1988 |
| Formula: | C29H42O8 |
| Molecular weight: | 518 |
| 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 | CC1(C(=CC(=O)O1)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)O)C | 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@](O)(C)[C@@H](CC1=CC(=O)OC1(C)C)O)O)C)C » 
| | IUPAC Name | 4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl]-5,5-dimethylfuran-2-one | | CAS-RN | 114805-00-4 | | PubChem CID | 101926945 | InChiKey
[ ChemIDPlus: search ] | CCCCNNJVLKLLKV-UYQGPDJCSA-N | | InChI | InChI=1S/C29H42O8/c1-25(2)15(11-24(34)37-25)10-23(33)28(5,35)22-7-9-29(36)17-12-19(30)18-13-20(31)21(32)14-26(18,3)16(17)6-8-27(22,29)4/h11-12,16,18,20-23,31-33,35-36H,6-10,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | 519 [MH]+, 501, 483, 393, 375, 363, 345 | | EI-MS m/z | 363, 345 | | HR-MS | |
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| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | | | 28 | | | 29 | |
| CD3OD | | 01 | 37.33 | | 02 | 38.70 | | 03 | 68.44 | | 04 | 32.82 | | 05 | 51.75 | | 06 | 206.35 | | 07 | 122.29 | | 08 | 167.56 | | 09 | 35.06 | | 10 | 39.26 | | 11 | 21.52 | | 12 | 32.46 | | 13 | (49.0) | | 14 | 85.28 | | 15 | 31.83 | | 16 | 21.63 | | 17 | 50.43 | | 18 | 18.02 | | 19 | 24.41 | | 20 | 77.41 | | 21 | 21.08 | | 22 | 75.49 | | 23 | 30.65 | | 24 | 174.91 | | 25 | 89.74 | | 26 | 25.02 | | 27 | 24.87 | | 28 | 115.46 | | 29 | 178.79 |
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| CD3OD | | 01-Ha | 1.43 | | 01-Hb | 1.78 | | 02-Ha | 3.82 (m, w1/2=22) | | 03-He | 3.94 (m, w1/2=8) | | 04-Ha | 1.65 | | 04-He | 1.75 | | 05-H | 2.40 (dd, 12, 5) | | 07-H | 5.81 (d, 2.5) | | 09-Ha | 3.15 (m, w1/2=22) | | 11-Ha | 1.67 | | 11-He | 1.80 | | 12-Ha | 2.13 (ddd ) | | 12-He | 1.85 | | 15-Ha | | | 15-Hb | | | 16-Ha | 2.05 | | 16-Hb | 1.75 | | 17-H | 2.38 | | 18-Me | 0.91 (s ) | | 19-Me | 0.97 (s ) | | 21-Me | 1.27 (s ) | | 22-H | 3.70 (dd, 10.5, 2) | | 23-Ha | 2.57 (ddd, 17.5, 2, 2) | | 23-Hb | 2.28 | | 26-Me | 1.48 (s ) | | 27-Me | 1.48 (s ) | | 28-C=CH | 5.92 (s ) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 1745 (alpha,beta-ethylenic gama-lactone) | | UV (MeOH) λ max (log ε) | 210 (?), 242 (?) |
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| HPTLC | | | TLC | Rf 0.39 (EtOAC-MeOH-NH4OH 85:10:5); Rf 0.47 (CH2Cl2-EtOH 85:15) | | GLC | | | HPLC | NP-HPLC, (Zorbax-Sil) Ret. 20.4 min (CH2Cl2-iPrOH-H2O, 125:25:2); flow-rate 1 ml. min-1 (20E = 53.2 min). |
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Drosophila melanogaster BII cell assay: EC50 = 4.4 x 10-7M |
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| First isolation | GIRAULT, J.-P. et al. (1988) Phytochemistry 27, 737-741 |
 | | Identification | VOKÁČ, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 |
| | Bioactivities | DINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 |
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Permanent link to this datasheet: CARTHAMOSTERONE
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