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| Year of first report: | 1967 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Lastrea thelypteris [fern] »  ![Wikipedia: <br />
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Onoclea sensibilis [fern] »
Pfaffia iresinoides [Amaranthaceae] »
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 480, 462, 444, 426, 408, 363 (M-117), 345, 328, 117, 99, 81 | | HR-MS | |
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| C5D5N | | 01 | 37.7 | | 02 | 68.1 | | 03 | 68.0 | | 04 | 32.4 | | 05 | 51.3 | | 06 | 203.8 | | 07 | 121.6 | | 08 | 166.3 | | 09 | 34.3 | | 10 | 38.6 | | 11 | 21.0 | | 12 | 31.9 | | 13 | 48.0 | | 14 | 84.1 | | 15 | 31.6 | | 16 | 21.4 | | 17 | 49.9 | | 18 | 17.9 | | 19 | 24.4 | | 20 | 76.8 | | 21 | 21.6 | | 22 | 77.4 | | 23 | 35.7 | | 24 | 76.7 | | 25 | 33.8 | | 26 | 17.0 | | 27 | 19.5 |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.16 (br dt, 11.8, 3.4) | | 03-He | 4.22 (br s ) | | 04-Ha | | | 04-He | | | 05-H | 3.02 (dd, 13.0, 4.3) | | 07-H | 6.25 (d, 2.2) | | 09-Ha | 3.58 (br t, 9.2) | | 11-Ha | | | 11-He | | | 12-Ha | 2.60 (dt, 13.0, 5.0) | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | 2.47 (q, 10.4) | | 16-Hb | | | 17-H | 2.94 (t, 9.2) | | 18-Me | 1.21 (s ) 1.18* | | 19-Me | 1.06 (s ) 1.05* | | 21-Me | 1.59 (s ) 1.54* | | 22-H | 4.12 (br d, 10.6) | | 23-Ha | | | 23-Hb | | | 24-H | 3.94 (dt, 9.0, 4.0) | | 26-Me | 1.003 (d, 6.6) 1.00* | | 27-Me | 1.006 (d, 6.6) 1.00* |
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| M.P. | 229-230 °C | | [α]D20 | + 7.4° (c ; MeOH) | | IR (KBr) ν max (cm-1) | 3420 (OH), 1650 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 243 (?) |
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| HPTLC | | | TLC | silicagel plates, Rf 0.54 (CHCl3-MeOH-H2O, 13:7:2) | | GLC | | | HPLC | |
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Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-9M | Sarcophaga assay: highly active |
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| First isolation | TAKEMOTO, T. et al. (1967) Chem. Pharm. Bull. 15, 1816 |
 | | General | TAKEMOTO, T. et al. (1968) Tetrahedron Lett., 375-378 |
| | General | BLUNT, J.W. et al. (1979) Aust. J. Chem. 32, 779-782 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | NISHIMOTO, N. et al. (1988) Phytochemistry 27, 1665-1668 |
| | General | NISHIMOTO, N. et al. (1988) Phytochemistry 26, 2505-2507 |
| | 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: PTEROSTERONE
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