Four new cytotoxic cyclic hexa- and heptapeptides from the marine ascidian Didemnum molle

Tetrahedron

Volumn 54, Issue 43, 1998, Pages 13203-13210

  Rudi, Amira ^a   Aknin, Maurice ^b   Gaydou, Emile M ^c   Kashman, Yoel ^a  

^a TEL AVIV UNIVERSITY   (Israel)

^b INSTITUT UNIVERSITAIRE EUROPÉEN DE LA MER   (France)

^c NONE

Author keywords

Marine metabolites; NMR; Peptides

Indexed keywords

COMORAMIDE A; COMORAMIDE B; CYCLOPEPTIDE; HEPTAPEPTIDE; HEXAPEPTIDE; MAYOTAMIDE A; MAYOTAMIDE B; UNCLASSIFIED DRUG;

ALGA; ANIMAL CELL; ARTICLE; ASCIDIACEA; CELL STRAIN HT29; COMOROS; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; LAGOON; MARINE ENVIRONMENT; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE ANALYSIS; PRIORITY JOURNAL; PROKARYOTE; SYMBIOSIS; TUMOR CELL LINE;

EID: 0032558652     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00801-1     Document Type: Article

References (9)

1. [1] Faulkner D.J. Nat. Prod. Rep. 1997, 14, 259-302 and earlier reports in this series.
2. [2] Chill, L.; Kashman, Y.; Schleyer, M. Tetrahedron 1997, 53, 16147-16152.
3. [3] Carroll, A.R.; Bowden, B.F.; Coll, J.C.; Hockless, D.C.R.; Skelton, B.W.; White A.H. Aust.J.Chem. 1994, 47, 61-69.
4. [4] Toske, S.G.; Fenical, W. Tetrahedron Lett. 1995, 36, 8355-8358.
5. [5] Prinsep, M.R.; Moore, R.E.; Levine, I.A.; Patterson, M.L. J. Nat. Prod. 1992, 55, 140-142.
6. [6] Gunasekera, S.P.; Pomponi, S.A.; McCarthy, P.J. J. Nat. Prod. 1994, 57, 79-83.
7. [7] Comparison of the proton NMR spectra of the chromatography fractions during the isolation of 3 and 4 showed clearly their transformation to more stable derivatives. Secondly, obtaining two sulfoxides is consistent with the air oxidation of 3 and 4 during their isolation.
8. [8] When these signals were first observed during the isolation process, they were suspected to belong to N-Me groups.
9. [9] Interesting to note is the great easiness under which compound 3 (and 4) undergoes air-oxidation, to a mixture of sulfoxides, in contrast to other methionine containing cyclic peptides. For example, dendroamide B[5] first isolated from a blue-green alga and also by us from an ascidian is stable to air and thus dendroamide C[5], the corresponding natural sulfoxide is a single diastereomer.