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CAS Registry Number: 190519-40-5
Taxonomy: Physicochemical and Biological Properties of Phytoecdysteroids – Phytoecdysteroids and Their Conjugates
C28H44O7: 492.3087
IR (KBr) νmax cm−1: 3406, 1657, 1061 [2]
EI-MS m/z: 456 [M-2H2O]+ (1), 438 (2), 423 (1), 409 (1), 395 (1), 367 (2), 343 (7), 325 (8), 309 (5), 300 (25), 285 (25), 267 (21), 185 (13), 171 (17), 157 (15), 139 (13), 129 (17), 118 (33), 83 (45), 71 (43), 55 (53), 43 (100) [2]
FAB-MS m/z: 515 [M + Na]+ (8), 493 [M + H]+ (10), 475 (35), 457 (7), 439 (3), 316 (10), 299 (8), 283 (8), 281 (8), 250 (58), 231 (11), 213 (13), 133 (55), 115 (35), 105 (33), 91 (60), 83 (87), 71 (55), 55 (100) [2]
HR-MS m/z: for C28H45O7 [M + H]+ calcd. 493.3165, found 493.3261 [2]
1 H NMR (500 MHz, J/Hz, CD3OD):1.38 (dd, J = 12.8, 12.0, Ha-1), 2.59 (dd, J = 12.8, 4.2, He-1), 4.01 (ddd, J = 11.7, 4.0, 3.3, Ha-2), 3.96 (q, J = 2.9, He-3), 1.78 (dt, J = 13.5, 13.5, 2.4, Ha-4), 1.69 (dt, J = 14.0, 3.6, 3.6, He-4), 2.34 (dd, J = 13.0, 4.0, H-5), 5.81 (dd, J = 2.7, 1.0, H-7), 3.16 (dd, J = 9.0, 2.7, H-9), 4.10 (ddd, J = 10.7, 8.7, 6.0, Ha-11), 2.25 (dd, J = 12.0, 11.0, Ha-12), 2.14 (dd, J = 12.2, 5.8, He-12), 1.96 (m, Ha-15), 1.62 (m, Hb-15), 1.96 (m, Ha-16), 1.96 (m, Hb-16), 2.49 (dd, J = 9.5, 8.5, H-17), 0.843 (s, CH3-18), 1.055 (s, CH3-19), 1.306 (s, CH3-21), 2.85 (d, J = 2.4, H-22), 2.72 (dd, J = 7.8, 2.4, H-23), 1.12 (m, H-24), 1.68 (m, H-25), 0.987 (d, J = 6.8, CH3-26), 0.962 (d, J = 6.8, CH3-27), 0.987 (d, J = 6.8, CH3-28) [2]
13 C NMR (125.7 MHz, CD3OD) [2]:
Table 1
C-1 | 39.09 | C-11 | 69.47 | C-21 | 24.01 |
2 | 68.95 | 12 | 43.52 | 22 | 66.75 |
3 | 68.58 | 13 | 23 | 59.93 | |
4 | 33.30 | 14 | 84.69 | 24 | 43.11 |
5 | 52.78 | 15 | 31.84 | 25 | 34.42 |
6 | 206.71 | 16 | 21.88 | 26 | 20.85 |
7 | 122.71 | 17 | 54.26 | 27 | 19.90 |
8 | 165.70 | 18 | 18.75 | 28 | 13.94 |
9 | 42.96 | 19 | 24.60 | ||
10 | 39.89 | 20 | 72.80 |
Pharm./Biol.: Drosophila melanogaster BII bioassay: EC50 = 6.5 × 10−6M [3].
References
K. Vokas, M. Budesinsky, J. Harmatha, in Abstracts of the 16th Conference on Isoprenoids, Prague, 1995, p. 77
K. Vokas, M. Budesinsky, J. Harmatha, J. Pis, Tetrahedron 54, 1657 (1998)
J. Harmatha, L. Dinan, Arch. Insect Biochem. Physiol. 35, 219 (1997)
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(2013). Atrotosterone B. In: Azimova, S.S. (eds) Natural Compounds. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-0543-6_74
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