Bastadin 20 and Bastadin O-Sulfate Esters from Ianthella basta: Novel Modulators of the Ry1R FKBP12 Receptor Complex

New compounds bastadin 20 (9), 15,34-O-disulfatobastadin 7 (10), and 10-O-sulfatobastadin 3 (11) were isolated from Ianthella basta collected in Exmouth Gulf, Western Australia. Compounds 10 and 11 exhibited moderate differential activity as SR Ca2+ channel agonists (EC50 13.6 and 100 μM, respective...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 1996-12, Vol.59 (12), p.1121-1127
Hauptverfasser:	Franklin, Melanie A, Penn, Sharron G, Lebrilla, Carlito B, Lam, Tien H, Pessah, Isaac N, Molinski, Tadeusz F
Format:	Artikel
Sprache:	eng
Schlagworte:	ANIMAL PRODUCTS Animals AUSTRALIA OCCIDENTAL AUSTRALIE OCCIDENTALE Biological and medical sciences Calcium Channel Agonists - chemistry Calcium Channel Agonists - pharmacology Calcium Channels - drug effects Calcium Channels - metabolism Cell Line CHEMICAL COMPOSITION CHEMICAL STRUCTURE COMPOSICION QUIMICA COMPOSITION CHIMIQUE ESPECTROMETRIA ESTER ESTERES ESTERS ESTRUCTURA QUIMICA General pharmacology Halogenated Diphenyl Ethers Magnetic Resonance Spectroscopy Medical sciences MEDICINAL PROPERTIES Muscle Proteins - drug effects Muscle Proteins - metabolism PARAZOA PEPTIDE PEPTIDES Peptides, Cyclic - chemistry Peptides, Cyclic - pharmacology PEPTIDOS Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Phenyl Ethers - chemistry Phenyl Ethers - pharmacology Porifera - chemistry PRODUCTOS DE ORIGEN ANIMAL PRODUIT ANIMAL PROPIEDADES MEDICINALES PROPRIETE PHARMACOLOGIQUE Ryanodine Receptor Calcium Release Channel SPECTRAL ANALYSIS SPECTROMETRIE SPECTROMETRY Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization STRUCTURE CHIMIQUE WESTERN AUSTRALIA
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Zusammenfassung:	New compounds bastadin 20 (9), 15,34-O-disulfatobastadin 7 (10), and 10-O-sulfatobastadin 3 (11) were isolated from Ianthella basta collected in Exmouth Gulf, Western Australia. Compounds 10 and 11 exhibited moderate differential activity as SR Ca2+ channel agonists (EC50 13.6 and 100 μM, respectively) of the Ry1R FKBP12 complex, while the potency of 9 was almost half that of 10 (EC50 20.6 μM). The problem of dereplication of bastadins was addressed using 1H-NMR “fingerprinting” of MeO signals in the corresponding permethyl bastadin derivatives.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np960507g