Two More Bastadins, 16 and 17, from an Indonesian Sponge Ianthella basta

Abstract

New bastadins 16 [1] and 17 [2] and the previously reported bastadins 3 13], 5 [4], 6 [5], 8 [6], 9 [7], and 12 [8] were isolated from the sponge lanthella hasta collected in Indonesia.The bastadins are a series of predominantly macrocyclic sponge metabolites, which are biogenetically derivable from four tyrosines by oxidative phenolic coupling of two tyramine-tyrosine units (1-8). A recent collection of marine invertebrates in Indonesia provided a specimen of lanthella basta Pallas from which were isolated several known and two new bastadins.

The Marine Bromotyrosine Derivatives

“…Bastadin-15 was identified from an undescribed marine sponge of the genus Ianthella collected from Australia (134). and −17 (221) were isolated from an Indonesian collection of I. basta (135)(136)(137). Bastadin-18, along with bastadins-1, −2, −5, −6, −8, and −10, were isolated from the marine sponge I. basta collected in Papua New Guinea (138).…”

Isolation of bastadin-6-O-sulfate and expedient purifications of bastadins-4, -5 and -6 from extracts of Ianthella basta

“…Pure bastadin-5 ( 5 , 5.2 mg) eluted as a peak at 15.6 min, while pure bastadin-6 ( 6 , 4.0 mg) eluted at 17.2 min. The peak eluting at 14.2 min, ‘ X ’, contained a mixture of bastadins-16[15] and −19[9] that could be separated under alternative HPLC conditions (RP C 18 ). Bastadin-4 ( 4 , 11.0 mg) was the major component of fraction 6.…”

“…RP HPLC chromatogram of Sephadex LH-20 Fraction 4 from Ianthella basta (UV detection, λ 250 nm) ; See Experimental and Section 2.4 for conditions.). Retention times: X – a mixture of bastadins-16[15], and −19[9] ( t R = 14.2 min), bastadin-5 ( 5 , t R = 15.6 min), bastadin-6 ( 6 , t R = 17.2 min).…”

Search for Anti-angiogenic Substances from Natural Sources

“…[9][10][11][12][13][14][15][16][17][18][19][20][21] More than twenty bastadins have been identified so far from marine sponges of Ianthella sp., Psammaplysilla sp. and Dendrilla sp., and they have been known to exhibit some interesting biological activities, such as antibacterial 9) and cytotoxic [10][11][12][13] activities, enzyme inhibitory activities against inositol-5′-phosphate dehydrogenase, 14) topoisomerase II and dihydrofolate reductase, 12) selective inhibitory activity toward δ-opioid receptors, 13) and interaction with the intracellular ryanodine receptor-1 (RyR-1) calcium channel complex.…”