|
|
|
|
Year of first isolation: |
1983 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Abuta velutina [Menispermaceae] »  ![Wikipedia: Abuta velutina [Menispermaceae]](/images/wikipedia.png)
Vitex strickeri [Lamiaceae (alt. Labiatae)] »
Polypodium vulgare [Polypodiaceae] »
|
| Occurence in animals: |
|
|
|
| |
| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CC(C(C)(C)O)O)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](C[C@@H](C(C)(C)O)O)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,5,6-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 88669-02-7 | | PubChem CID | 11016518 | InChiKey
[ ChemIDPlus: search ] | NXKBQUXBPMOHPK-MLXSIWSOSA-N | | InChI | InChI=1S/C27H44O8/c1-23(2,33)21(31)12-22(32)26(5,34)20-7-9-27(35)15-10-17(28)16-11-18(29)19(30)13-24(16,3)14(15)6-8-25(20,27)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 |
| |
| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 460 (M-2H2O)+(1), 442 (1), 424 (2), 363 (3), 345 (10), 327 (6), 319 (1), 301 (4), 283 (4), 177 (4), 159 (15), 141 (15), 133 (8), 123 (12), 115 (34), 103 (3),97 (28), 89 (4), 85 (17), 71 (100), 67 (13), 59 (80), 53 (10), 41 (15) | | HR-MS | | | FAB-MS m/z | 497 (M+1)+ |
|
|
| C5D5N | | 01 | 38.1 | | 02 | 68.2 * | | 03 | 68.1 * | | 04 | 32.6 | | 05 | 51.5 | | 06 | 203.5 | | 07 | 121.7 | | 08 | 166.2 | | 09 | 34.6 | | 10 | 38.8 | | 11 | 21.2 | | 12 | 31.8 | | 13 | 48.2 | | 14 | 84.2 | | 15 | 32.1 | | 16 | 21.9 | | 17 | 50.1 | | 18 | 18.0 | | 19 | 24.6 | | 20 | 76.9 | | 21 | 21.6 | | 22 | 78.3 | | 23 | 33.1 | | 24 | 80.4 | | 25 | 72.3 | | 26 | 27.0 | | 27 | 25.4 |
|
| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | 3.85 (dt, 11, 3) | | 03-He | 3.97 (br s ) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.83 (d, 2) | | 09-Ha | 3.17 (dt, 8, 2) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.89 (s ) | | 19-Me | 0.96 (s ) | | 21-Me | 1.14 (s ) | | 22-Hb | 3.68 (dd, 9, 2) | | 23-Ha | | | 23-Hb | | | 24-Ha | 3.54 (dd, 9, 2) | | 26-Me | 1.18 (s ) | | 27-Me | 1.22 (s ) |
| C5D5N | | 01-Ha | 1.83-1.58 | | 01-He | 2.07-2.19 | | 02-Ha | 4.24 | | 03-He | 4.22 | | 04-Ha | 1.70-1.81 | | 04-He | 1.98-2.05 | | 05-H | 2.97-3.03 | | 07-H | 6.23 (d, 3) | | 09-Ha | 3.58 (m, w1/2 = 24) | | 11-Ha | 1.70-1.81 | | 11-He | 1.83-1.95 | | 12-Ha | 2.56 (ddd, 13, 13, 5) | | 12-He | 1.83-1.95 | | 15-Ha | 1.83-1.95 | | 15-Hb | 2.07-2.19 | | 16-Ha | 2.41-2.50 | | 16-Hb | 1.98-2.05 | | 17-H | 2.97-3.03 | | 18-Me | 1.20 (s ) | | 19-Me | 1.08 (s ) | | 21-Me | 1.58 (s ) | | 22-Hb | 4.07 (dd, 9, 1) | | 23-Ha | 2.07-2.19 | | 23-Hb | 2.41-2.50 | | 24-Ha | 4.19 (dd, 2, 12) | | 26-Me | 1.45 (s ) | | 27-Me | 1.50 (s ) |
|
| |
| M.P. | 257-259 °C (270-272°C, needles from Vitex ) | | [α]D20 | 32 ° (c 2.0; MeOH) | | IR (KBr) ν max (cm-1) | 3380, 1660, 1640 | | UV (MeOH) λ max (log ε) | 242 (4.14) |
| |
| TLC | | | RLCC | solvent system H2O-EtOAc-n-PrOH (6:6:1) | | GLC | | | HPLC | NP-HPLC, silica (Zorbax-SIL) solvent CH2Cl2-iPrOH-H2O (100:40:3), flow-rate 1 ml. min-1, Rt 6.7 min (20E = 4.9 min); Recycle RP-HPLC : column asahipack GS-320 (50 x 2 cm i.d.) solvent MeOH, flow-rate 3.5 ml.min-1. |
| |
Drosophila melanogaster BII cell bioassay: EC50 = 1.4 x 10-7M |
| |
| First isolation | PINHEIRO, M.L.B. et al. (1983) Phytochemistry 22, 2320-2321 |
 | | General | LAFONT, R. et al. (1990) In: Bioanalysis of Drugs and Metabolites (Eds. E. Reid, J. D. Robinson, I. D. Wilson), Plenum, pp. 79-94 |
| | General | HONDA, T. et al. (1991) Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 33, 212-219 |
| | General | ZHANG, M. et al. (1992) Phytochemistry 31, 247-250 |
| | Bioactivities | CLEMENT, C.Y. et al. (1993) Insect Biochem. Molec. Biol. 23, 187-193 |
| | Identification | COLL, J. et al. (1994) Tetrahedron 50, 7247-7252 |
|
| |
Permanent link to this datasheet: ABUTASTERONE
|
|
