1-O-Sulfatobastadins-1 and -2 from Ianthella basta (Pallas). Antagonists of the RyR1-FKBP12 Ca2+ channel

Marine Drugs

Volumn 2, Issue 4, 2004, Pages 176-184

  Masuno, Makoto N ^a   Hoepker, Alexander C ^a   Pessah, Isaac N ^a   Molinski, Tadeusz F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Bromotyrosine; Calcium channel; Porifera; Ryanodine receptor

Indexed keywords

EID: 33645834056     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md204176     Document Type: Article

References (19)

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2. Mack, M. M.; Molinski, T. F.; Buck, E. D.; Pessah, I. N. Novel Modulators of Skeletal Muscle FKBP12/Calcium Channel Complex from Ianthella basta: Role of FKBP in Channel Gating. J. Biol. Chem. 1994, 269, 23236-23249.
3. Clardy, J. The Chemistry of Signal Transduction. Proc. Nat. Acad. Sci. U.S.A. 1995, 92, 56-61.
4. Pordesimo, E. O.; Schmitz, F. J. New Bastadins from the Sponge Ianthella basta. J. Org. Chem. 1990, 55, 4704-4709.
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7. Pettit, G. R.; Butler, M. S.; William, M. D.; Filiatrault, M. J.; Pettit, R. K. Isolation and Structure of Hemibastadinols 1-3 from the Papua New Guinea Marine Sponge Ianthella basta. J. Nat. Prod. 1996, 59, 927-934. (Pubitemid 26365483)
8. + is the most likely counter ion from extraction of marine invertebrates. The numbering scheme used here for 2 and 3 is adopted from Pettit (reference 6b) and differs from the numbering of the macrocyclic bastadins (eg. 1, reference [1]).
9. Franklin, M. A.; Penn, S. G.; Lebrilla, C. B.; Lam, T. H.; Pessah, I. N.; Molinski, T. F. Bastadin 20 and Bastadin O-Sulfate Esters from Ianthella basta: Novel Modulators of the Ry(1)R FKBP12 Receptor Complex. J. Nat. Prod. 1996, 59, 1121-1127 (Pubitemid 27026570)
10. Franklin, M. A. M.Sc. Thesis, University of California, Davis, 1995.
11. Unlike simple acyclic oximes which exhibit facile E-Z isomerism, the configuration of the C=N double bond in every cyclic bastadin is strictly E. A strong intramolecular H-bond between the amide NH and the N=C groups forms a rigid, planar 5-membered ring and places the OH group anti to the H-bonded donor electron pair on the imine nitrogen (viz. X-ray structures of bastadin-4 [1] and bastadin-10, Molinski, T. F.; Olmstead, M. M., unpublished results). Both E/Z oxime isomers have been detected in related α-ketoximines from marine sponges and the E geometry has been correlated with an upfield 13C-NMR signal for the benzylic CH2 group (δ ~28 ppm, c.f. Z-δ ~35 ppm. Arabshahi, L.; Schmitz, F. J. Brominated Tyrosine Metabolites from an Unidentified Sponge. J. Org. Chem. 1987, 52, 3584). Compounds 2, 3 and 5 have E oximes.
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14. 13C-NMR assignment (δ 154.0, s) of the parent alcohol, hemibastadin-1 [6b].
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