Natural Compounds

2013 Edition
| Editors: Shakhnoza S. Azimova, Ashraf I. Saidkhodzhaev

10α-Angeloyloxy-6α-isobutyroyloxy-4β,8α-dihydroxy-5α(H)-dauc-9-one (6-O-Desangeloyl-6-O-isobutanoyl-laserpitine)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_961

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Daucanes (Carotanes) – Diesters

Biological sources: Laserpitium latifolium L. [1]

C24H38O7: 438.2616

Mp: amorphous [1]

[α]D 85° (c 0.064, EtOH) [1]

IR: 3500, 2975, 2940, 2880, 1715, 1650, 1455, 1390, 1230, 1155 [1]

MS: 439 [M + 1]+ (61), 421 (16), 391 (16), 351 (3), 333 (100), 315 (30), 233 (25) [1]

1H NMR (200 MHz, CDCl3): 0.79 and 0.90 (6H, d, J = 6.8, H-12, H-13), 1.40 and 1.41 (6H, s, H-14, H-15), 1.65 (5H, d, H-2, H-3, H-11), 2.07 (1H, d, J = 11.1, H-5), 2.27 (1H, d, J = 15.9, H-7a), 2.27 (1H, dd, J = 4; 15.9, H-7b), 5.26 (1H, s, H-10), 5.36 (1H, dd, J = 4.9; 11.1, H-6); OAng: 1.94 (3H, m, J < 1, H-5′), 2.00 (3H, dq, J = 7.3, H-4′), 6.14 (1H, qm, J = 7.0, H-3′); OiBu: 1.18 and 1.20 (6H, d, J = 6.8, H-3″, H-4″), 2.53 (1H, m, H-2″) [1]

13 C NMR (67.9 MHz, CDCl 3, TMS) [ 1]:

Table 1

C-1

45.7

C-9

209.6

C-2′

127.0

2

34.3

10

80.7

3′

139.1

3

31.2

11

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References

  1. 1.
    P. Moldt, U.W. Smitt, S.B. Christensen, J. Nat. Prod. 50, 974 (1987)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013