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| Year of first report: | 1983 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Abuta velutina [Menispermaceae] »  ![Wikipedia: <br />
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Vitex strickeri [Lamiaceae] »
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| 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)+ |
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| 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 |
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| 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 ) |
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| 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) |
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| 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. |
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Drosophila melanogaster BII cell bioassay: EC50 = 1.4 x 10-7M |
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| 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 (Ed. E. Reid, J. D. Robinson and 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 |
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Permanent link to this datasheet: ABUTASTERONE
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