Isolation and Structure Elucidation of 34-Sulfatobastadin 13, an Inhibitor of the Endothelin A Receptor, from a Marine Sponge of the Genus Ianthella

Abstract

34-Sulfatobastadin 13 [1] was isolated from the sponge Ianthella sp. Its structure was elucidated by nmr techniques and chemical transformation to bastadin 13 [2]. Compound 1 weakly inhibited binding to the endothelin A receptor (ETA), while compound 2 inhibited growth of Bacillus subtilis.

1-O-Sulfatobastadins-1 and -2 from Ianthella basta (Pallas).Antagonists of the yR1-FKBP12 Ca2+ Channel

“…Pooled extracts that eluted with 3:1 CH 2 Cl 2 -MeOH were further purified by HPLC (reversed phase, C 18 , MeOH-H 2 O followed by C 18 , 70:30:0.05 H 2 O-CH 3 CN-TFA) to provide two new sulfated hemibastadins, 2 and 3 , the known 4 [11] and the novel 34- O -sulfatobastadin-9 ( 5 ). All compounds were readily soluble in MeOH and appreciably soluble in water, but insoluble in CHCl 3 .…”

The Marine Bromotyrosine Derivatives

“…Since the significant antimicrobial activity of psammaplin A (152) was disclosed, the antibacterial activities against 40 drug- Bastadins-1 to-7 (204)(205)(206)(207)(208)(209)(210)(211) were isolated because of the potent activity against Grampositive and Gram-negative bacteria, but data were not provided (129). Bastadin-13 showed a minimum inhibitory concentration of 6 μg/mL against Bacillus subtilis, while 34-sulfatobastadin-13 showed no activity at 50 μg/mL, suggesting the free phenolic group at C-34 is required for the antimicrobial activity (141 …”

Macrocyclic Inhibitors of GPCR's, Integrins and Protein–Protein Interactions

“…The bromotyrosine-derived macrolactam 34-sulfatobastadin 13 (33, Figure 8.13), isolated from the sponge Ianthella sp., weakly inhibits the binding of [ 125 I]-ET-1 to the ET A receptor with an IC 50 of 39 mM. 95 The polyketide (À)-kendomycin (34, TAN-2162, Figure 8.13) is a moderately potent inhibitor of both endothelin receptors (ET A : IC 50 ¼ 11.5 mM; ET B : IC 50 ¼ 2.9 mM), isolated from Streptomyces sp AL-71389. 96 The class II lasso peptide RES-701-1 (35, Figure 8 (16)) passing through the ring region.…”