Sagitol, a pyridoacridine alkaloid from the sponge Oceanapia sagittaria

Christine E. Salomon, D. John Faulkner

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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 languageEnglish (US)
Pages (from-to)9147-9148
Number of pages2
JournalTetrahedron Letters
Volume37
Issue number51
DOIs
StatePublished - Dec 16 1996
Externally publishedYes

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).

Copyright:
Copyright 2005 Elsevier B.V., All rights reserved.

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