The isolation and characterization of agardhilactone, a novel oxylipin from the marine red alga Agardhiella subulata

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4635-4638

  Graber, Melodie A ^a   Gerwick, William H ^a   Cheney, Donald P ^b  

^a OREGON STATE UNIVERSITY   (United States)

^b NORTHEASTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; LACTONE DERIVATIVE;

ALGA; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE;

AGARDHIELLA SUBULATA; ALGAE; RHODOPHYTA;

EID: 0030200003     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00921-5     Document Type: Article

References (18)

1. 1. Gerwick, W. H. Chem. Rev. 1993, 93, 1807-1823.
2. 2. Nagle, D. G.; Gerwick, W. H. J. Org. Chem. 1994, 59, 7227-7237.
3. 3. Krupina, M. V.; Dathe, W. Z. Naturforsch. 1991, 46C, 1127-1129.
4. 4. Gregson, R. P.; Marwood, J. F.; Quinn, R. J. Tetrahedron Lett. 1979, 20, 4505-4506.
5. 5. Proteau, P. J.; Gerwick, W. H. Tetrahedron Lett. 1992, 33, 4393-4396.
6. 6. Miralles, J.; Aknin, M.; Micouin L.; Gaydoou, E.-M.; Kornprobst, J.-M. Phytochemistry 1990, 29, 2161-2163.
7. 7. Higgs, M. D.; Mulheirn, L. J. Tetrahedron 1981, 24, 4259-4262.
8. 8. Kurata, K.; Taniguchi, K.; Shiraishi, K.; Hayama, N.; Tanaka, I.; Suzuki, M. Chemistry Lett. 1989, 267-270.
9. 9. Kurata, K.; Taniguchi, K.; Shiraishi, K.; Suzuki, M. Phytochemistry 1993, 33, 155-159.
10. 10. Although not completely characterized, the minor component was structurally similar from C1 to C10 but differed in the location of oxidation between C11 to C20.
11. 11. Lack of nOe correlations between protons of the cyclopentane and lactone rings precluded stereochemical assignment at C5.
12. 12. Proteau, P. J. Oxylipins from Temperate Marine Algae and a Photoprotective Sheath Pigment from Blue-Green Algae, Oregon State University, 1993.
13. 13. Hamburg, M. Anal. Biochem. 1971, 43, 515-526.
14. 14. MC derivatives were detected by GC-MS (11.5 m of HP Ultra-1, 100-210°C at 3.0° C per min., then isothermal for 15 min.), and eluted at 17.03 min. (S) and 17.27 min. (R).
15. 15. Although the scalemic nature of C18 could be due to extraction or derivatization procedures, it should be noted that plant lipoxygenases are known to produce S/R mixtures exceeding the 80:20 ratio observed herein. [Gardner, H. W. Biochim. Biophys. Acta 1991, 1084, 221-239.]
16. 16. Bernart, M.; Gerwick, W. H. Tetrahedron Lett. 1988, 29, 2015-2018.
17. 17. Khotimchenkco, S. V.; Vaskovsky, V. E. Botanica Marina 1990, 33, 525-528.
18. 18. Bernart, M. W.; Whatley, G. G.; Gerwick, W. H. J. Nat. Prod. 1993, 56, 245-259.