7β,8α-Diangeloyloxy-9α-hydroxy-5α,11α(H)-longipin-2-en-1-one (2-Dehydrorastevione; Longipin-2-ene-7β,8α,9α-triol-1-one 7,8-Diangelate)
Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Tricyclic Sesquiterpene Esters – Longipinanes – Diesters
Biological sources: Stevia triflora DC. [1]; S. serrata Cav. [2]; S. connata Lag. [3]
C25H34O6: 430.2355
Mp: colorless oil [1]
UV (MeOH): 252, 217 [1]
IR (film): 3450, 1750, 1680, 865 [1]
1H NMR (80 MHz, CDCl3, TMS): 0.85* (3H, s, H-12), 1.10 (3H, s, H-14), 1.18* (3H, s, H-13), 2.00 (3H, d, J = 1.5, H-15), 2.25 (1H, s, H-5), 2.62 (1H, d, J = 6, H-4), 3.18 (1H, d, J = 6, H-11), 3.78 (1H, d, J = 1.5, H-9), 5.46 (2H, br s, H-7, H-8), 5.74 (1H, m, J = 1.5, H-2), 2 × OAng: 1.73 (6H, m, J = 1.5, H-5′, H-5″), 1.80 (6H, dq, J = 6.5; 1.5, H-4′, H-4″), 6.02 (2H, dq, J = 6.5; 1.5, H-3′, H-3″); * – assignments may be interchanged [1]
Table 1
C-1 |
201.3 s |
C-8 |
70.2 da |
CH3 |
20.2 qb |
2 |
122.9 d |
9 |
75.2 d |
2 × OAng |
166.2 s and 166.0 s |
3 |
169.5 s |
10 |
55.4 s |
1′, 1″ |
139.4 d and 139.1 d |
4 |
48.3 d |
11 |
52.4 d |
2′, 2″ |
127... |
References
- 1.J.M. Amaro, M. Adrian, C.M. Cerda, P. Joseph-Nathan, Phytochemistry 27(5), 1409 (1988)Google Scholar
- 2.E. Sanchez-Arreola, C.M. Cerda-Garcia-Rojas, P. Joseph-Nathan, L.U. Roman, J.D. Hernandez, Phytochemistry 39(4), 853 (1995)Google Scholar
- 3.E. Sanchez-Arreola, C.M. Cerda-Garcia-Rojas, L.U. Roman, J.D. Hernandez, P. Joseph-Nathan, J. Nat. Prod. 63, 12 (2000)Google Scholar