Ajugasterone C-20,22-Acetonide

doi:10.1007/978-1-4614-0543-6_67

37 Accesses

Access provided by Autonomous University of Puebla. Download reference work entry PDF

CAS Registry Number: 142735-64-6

Taxonomy: Physicochemical and Biological Properties of Phytoecdysteroids – Phytoecdysteroids and Their Conjugates

Biological sources: Rhaponticum uniflorum [1], Serratula coronata [2], S. wolffi [3], Vitex polygama [4], V. strickeri [5]

C₃₀H₄₈O₇: 520.3400

Mp: 248–250°C [1], 287–288°C [3], 246–249°C [5]

IR (KBr) ν_max cm⁻¹: 3400–3440, 1675 [3]

IR (Nujol) ν_max cm⁻¹: 3200, 1650 [5]

UV λ ^MeOH_max nm: 237 [5]

EI-MS m/z: 520 [M]⁺ (0.3), 505 [M-CH₃]⁺ (0.7), 502 [M-H₂O]⁺ (0.3), 487 [M-CH₃–H₂O]⁺ (0.7), 469 [M-CH₃–2H₂O]⁺ (0.4), 462 (5.6), 444 (3.0), 427 (3.9), 379 (3.5), 344 (3.2), 317 (8.0), 266 (10.3), 185 (68.4), 127 (88.7), 109 (44.4), 59 (100) [1], 520 [M]⁺ (10), 505 (20), 502 (5), 487 (10), 469 (4), 462 (98), 445 (20), 444 (28), 427 (33), 426 (32), 420 (33), 411 10), 409 (20), 402 (13), 379 (20), 361 (17), 299 (12), 281 (7), 266 (33), 185 (100), 142 (58), 127 (83), 114 (33), 109 (33), 84 (60) [2], 379, 361, 325, 317, 299, 185 [5]

CI-MS m/z: 538 [M + H + NH₃]⁺, 521 [M + H]⁺, 503 [M + H–H₂O]⁺, 490, 480, 464, 447, 429, 413, 394, 391, 380, 364, 279, 230, 212, 178, 136, 124 [2]

FAB-MS m/z: 543 [M + Na]⁺, 527 [M + Li]⁺ [1]

¹ H NMR (500 MHz, J/Hz, C₅D₅N): 2.00 (d, J = 12.0, Ha-1), 3.42 (dd, J = 12.0, 5.0, He-1), 4.52 (Ha-2), 4.21 (d, J = 4.0, He-3), 1.78 (ddd, J = 14.0, 14.0, 4.0, Ha-4), 2.03 (dt, J = 14.0, 4.0, 4.0, 4.0, He-4), 3.04 (dd, J = 14.0, 4.0, H-5), 6.29 (d, J = 5.0, H-7), 3.82 (Ha-9), 4.57 (Ha-11), 2.95 (dd, J = 12.0, 12.0, Ha-12), 2.57 (dd, J = 12.0, 7.0, He-12), 1.95 (Ha-15), 2.19 (Hb-15), 2.13 (Ha-16), 2.23 (Hb-16), 2.79 (dd, J = 8.0, 8.0, H-17), 1.31 (s, CH₃-18), 1.32 (s, CH₃-19), 1.08 (s, CH₃-21), 3.86 (H-22), 1.55 (Ha-23), 1.39 (Hb-23), 1.55 (Ha-24), 1.50 (Hb-24), 1.46 (H-25), 0.81 (d, J = 8.0, CH₃-26), 0.81 (d, J = 8.0, CH₃-27), Other: 1.52 and 1.46 (20,22-iPr) [5]

¹³ C NMR (C₅D₅N) [3]:

Table 1

C-1	39.45	C-11	68.83	C-21	22.24
2	68.37	12	43.83	22	81.94
3	68.09	13	47.82	23	27.10
4	32.86	14	84.13	24	36.86
5	52.43	15	31.75	25	28.24
6	203.88	16	22.13	26	22.81
7	122.37	17	49.72	27	22.43
8	163.68	18	18.23	20,22-iPr	29.37
9	42.69	19	24.81		29.37
10	39.81	20	84.81		106.93

Pharm./Biol.: Drosophila melanogaster B_II bioassay: EC₅₀ = 6.0 × 10⁻⁷M [2].

References

J.K. Cheng, Y.H. Zhang, Z.Y. Zhang, D.L. Cheng, G.L. Zhang, Chem. J. Chinese Univ. 23, 2084 (2002)
CAS Google Scholar
V.N. Odinokov, S. Kumpun, I.V. Galyautdinov, N. Edvard-Todeschi, N.A. Veskina, L.M. Khalilov, J.P. Girault, L. Dinan, R. Lafont, Coll. Czech. Chem. Comm. 70, 2038 (2005)
Article CAS Google Scholar
K. Miladera, Z. Saatov, J.D. Kholodova, M.B. Gorovits, A.S. Shashkov, N.K. Abubakirov, Chem. Nat. Comp. 28, 59 (1992)
Article Google Scholar
T.C. Dos Santos, F. Delle Monache, S.G. Leitao, Fitoterapia 72, 215 (2001)
Article Google Scholar
M. Zhang, M.J. Stout, I. Kubo, Phytochemistry 31, 247 (1992)
Article CAS Google Scholar

Download references

Editor information

Editors and Affiliations

S.Yu. Yunusov Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Republic of Uzbekistan, Tashkent, Republic of Uzbekistan
Shakhnoza S. Azimova

Rights and permissions

Reprints and permissions

Copyright information

About this entry

Cite this entry

(2013). Ajugasterone C-20,22-Acetonide. In: Azimova, S.S. (eds) Natural Compounds. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-0543-6_67

Download citation

DOI: https://doi.org/10.1007/978-1-4614-0543-6_67
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4614-0542-9
Online ISBN: 978-1-4614-0543-6
eBook Packages: Chemistry and Materials ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics

Publish with us

Policies and ethics