Abstract
The sponge Oceanapia sagittaria from Palau contained the known sponge metabolite dercitamide (1) and a new pyridoacridine alkaloid sagitol (2). The structure of sagitol (2) was determined by interpretation of spectral data and confirmed by oxidation of dercitamide (1). CD measurements suggest that sagitol (2) is not an artifact.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 9147-9148 |
| Number of pages | 2 |
| Journal | Tetrahedron Letters |
| Volume | 37 |
| Issue number | 51 |
| DOIs | |
| State | Published - Dec 16 1996 |
| Externally published | Yes |
Bibliographical note
Funding Information:1. Gunawardana, G.P.; Khomoto, S.; Burres, N.S. Tetrahedron Lett. 1989, 30, 4359. 2. Gunawardana, G.P.; Koehn, F.E.; Lee, A.Y.; Clardy, J.; He, H.; Faulkner, D.J. J. Org. Chem. 1992, 57, 1523. 3. Carroll, A.R.; Scheuer, P.J. J. Org. Chem. 1990, 55, 4426. 4. Molinski, T.F. Chem. Rev. 1993, 93, 1825. 5. Faulkner, D.J.; He, H.; Unson, M.D.; Bewley, C.A.; Garson, M.J. Razz. Chim. Ital. 1993, 123, 301. 6. A specimen of Oceanapia sagittaria (95-061) has been deposited in the SIO Benthic Invertebrate Collection (P-l 163). 7. Sagitol(2): yellow glass; IR (film) 3280, 2930, 1645, 1600, 1560, 1450 cm’; UV (MeOH) 396 run (E l470), 351 nm(~ 3430),335 nm(~ 3920), 318 nm(e 3430),26Onm(e 22810); ‘H NMR (4OOMHz, CDCl,) 6 0.94 (t, 3 H, J = 7.5 Hz), 1.92 (q, 2 H. J = 7.5 Hz), 2.38 (m, 1 H), 2.47 (m, 1 H), 3.11 (m, 2 H), 4.60 (brs, -OH), 5.57 (br s, 1 H), 7.81 (t, 1 H, J = 8.5 Hz), 7.93 (t, 1 H, J = 8 Hz), 8.27 (d, 1 H, J = 8 Hz), 8.29 (d, 1 H, J = 8 Hz), 8.59 (d, 1 H, J = 8.5 Hz), 9.04 (s, 1 H), 9.05 (d, 1 H, J = 8.5 Hz); 13CN MR (100 MHz, CDCl,) 6 9.5 (t), 29.4 (d), 35.2 (d), 47.4 (d), 74.1 (s), 114.0 (s), 114.7 (d), 122.1 (s), 123.0 (d), 128.3 (d), 130.1 (d), 131.5 (d), 138.2 (s), 142.0 (s), 144.9 (s), 148.3 (s), 149.5 (s), 149.9 (d), 154.6 (d), 161.5 (s), 173.6 (s); EIMS m/z (int.) 390 (1, M), 290 (100); HRCIMS, Obsd. m/z = 391.1241, G,H,,N,O,S [M+H]+ requires m/z = 391.1229. 8. The sponge was collected by Larry Sharon and Mary Kay Harper, who also did the identification. We thank the Marine Resources Division, Republic of Palau, for a collecting permit. The research was supported by a grant from the National Science Foundation (CHE 95-27064).