Isolation and stereostructure of aurilide, a novel cyclodepsipeptide from the Japanese sea hare Dolabella auricularia

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6771-6774

  Suenaga, Kiyotake ^a   Mutou, Tsuyoshi ^a   Shibata, Takunobu ^a   Itoh, Takashi ^a   Kigoshi, Hideo ^a   Yamada, Kiyoyuki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AURILIDE; CYCLOPEPTIDE; DEPSIPEPTIDE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INVERTEBRATE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

ANASPIDEA; ANIMALIA; AURICULARIA; DOLABELLA AURICULARIA; INVERTEBRATA; LEPUS;

EID: 0030576999     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01464-5     Document Type: Article

References (22)

1. 1. Pettit, G. R.; Kamano, Y.; Herald, C. L.; Fujii, Y.; Kizu, H.; Boyd, M. R.; Boettner, F. E.; Doubek, D. L.; Schmidt, J. M.; Chapuis, J.-C.; Michel, C. Tetrahedron 1993, 49, 9151-9170.
2. 2. (a) Sone, H.; Nemoto, T.; Ojika, M.; Yamada, K. Tetrahedron Lett. 1993, 34, 8445-8448.
3. (b) Sone, H.; Nemoto, T.; Ishiwata, H.; Ojika, M.; Yamada, K. Tetrahedron Lett. 1993, 34, 8449-8452.
4. (c) Ishiwata, H.; Nemoto, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1994, 59, 4710-4711.
5. (d) Ojika, M.; Nemoto, T.; Nakamura, M.; Yamada, K. Tetrahedron Lett. 1995, 36, 5057-5058.
6. (e) Nakamura, M.; Shibata, T.; Nakane, K.; Nemoto, T.; Ojika, M.; Yamada, K. Tetrahedron Lett. 1995, 36, 5059-5062.
7. (f) Sone, H.; Shibata, T.; Fujita, T.; Ojika, M.; Yamada, K. J. Am. Chem. Soc. 1996, 118, 1874-1880.
8. 3. (a) Ojika, M.; Nemoto, T.; Yamada, K. Tetrahedron Lett. 1993, 34, 3461-3462.
9. (b) Sone, H.; Kondo, T.; Kiryu, M.; Ishiwata, H.; Ojika, M.; Yamada, K. J. Org. Chem. 1995, 60, 4774-4781.
10. (c) Ojika, M.; Nagoya, T.; Yamada, K. Tetrahedron Lett. 1995 36, 7491-7494.
11. (d) Suenaga, K.; Kigoshi, H.; Yamada, K. Tetrahedron Lett. 1996, in press.
12. 4. Cytotoxicity of aurilide (1) could not be evaluated owing to the scarcity of the sample.
13. c 13.8-17.1 and 21.0-24.4, respectively: Carey, L.; Clough, J. M.; Pattenden, G. J. Chem. Soc. Perkin Trans I 1983, 3005-3009.
14. 3COOH 1:99:0.05 (20 min), 1:99:0.05 to 10:90:0.05 (20 min, linear gradient), and then 10:90:0.05 (20 min); flow rate, 1.0 mL/min; detection at 205 nm. The retention times (min) of components: MeAla (3), Val (5), MeLeu (21), isoleucic acid (55).
15. 4/MeCN 9:1 for isoleucic acid; flow rate, 1.0 mL/min; detection at 254 nm. The retention times (min) of the authentic samples: L-Val (8.0), D-Val (4.0), L-MeLeu (9.0), D-MeLeu (6.7), L-isoleucic acid (64), D-isoleucic acid (39), allo-L-isoleucic acid (52), and allo-D-isoleucic acid (32).
16. 8. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591-596.
17. 9. Conditions for the HPLC analysis: column, Develosil ODS-HG-5 (4.6 × 250 mm); solvent, MeOH/0.02 M AcONa (pH 4.0) 1:1; flow rate 1.0 mL/min; detection at 340 nm. The retention times (min) of the authentic Marfey derivatives of MeAla: L-MeAla (5.3) and D-MeAla (6.3).
18. 6) δ 7.90 (d, J = 8.4 Hz, 2 H), 7.78 (d, J = 8.4 Hz, 2 H), 7.61 (d, J = 8.4 Hz, 2 H), 5.63-5.58 (m, 2 H), 5.57 (d, J = 9.9 Hz, 1 H), 5.49 (br t, J = 7.3 Hz, 1 H), 4.48 (d, J = 12.5 Hz, 1 H), 4.42 (d, J = 12.5 Hz, 1 H), 2.58 (ddq, J =9.9, 4.4, 7.3 Hz, 1 H), 2.44-2.40 (m, 2 H), 1.54 (s, 3 H), 1.50 (s, 3 H), 0.86 (d, J = 7.3 Hz, 3 H), 0.83 (t, J = 7.3 Hz, 3 H). The signals due to six protons in 3 were not observed due to the overlap with the solvent signals.
19. 11. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945-948.
20. (b) Evans, D. A.; Rieger, D. L.; Tetrahedron Lett. 1990, 31, 7099-7100.
21. (c) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515.
22. 12. Pettit, G. R.; Kamano, Y.; Herald, C. L.; Dufresne, C.; Bates, R. B.; Schmidt, J. M.; Cemy, R. L.; Kizu, H. J. Org. Chem. 1990, 55, 2989-2990.