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

Masuno, Makoto N.; Hoepker, Alexander C.; Pessah, Isaac N.; Molinski, Tadeusz F.

doi:10.3390/md204176

Cited by 14 publications

(25 citation statements)

References 13 publications

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“…This formula provided a match to four previously reported bastadins: 5 ( 6 ), 9, 14, 15, 22, 24, 26, 27 15, 16, 28 16 29 and 19 ( 1a ), 24, 26 while also ruling out the presence of benzene rings coded as 3 and 6 in Table 1. The constitutions of the four aryl rings, containing nine protons as three distinct two-spin systems and one ABX pattern, were established using the Table 1 database plus g COSY NMR data.…”

Section: Resultssupporting

confidence: 78%

Additional Insights on the Bastadins: Isolation of Analogues from the Sponge Ianthella cf. reticulata and Exploration of the Oxime Configurations

et al. 2010

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The focus of this study was on the bastadin class of bromotyrosine derivatives, commonly isolated from Ianthella marine sponges, and is the first report on the secondary metabolites from Ianthella cf. reticulata. Two new bastadins were isolated, (E,Z)-bastadin 19 (1b), a diastereoisomer of the known (E,E)-bastadin 19 (1a), and dioxepine bastadin 3 (2), an unusual dibenzo-1,3-dioxepine. A bastadin NMR database was created and assisted in the structure determination of 1b, 2 and the rapid dereplication of ten other known compounds including bastadins 2–9 (3-10), 13 (11) and 19 (1a). The geometry of the 2-(hydroxyimino)-N-alkylamide chains, a chemical feature present in all bastadins, was further probed and new insights regarding the natural oxime configuration are discussed. Bastadins possessing (E,Z), (Z,E) or (E,E)-dioxime configurations could be artifacts of isolation or storage in solution. Therefore, this point was explored by photochemical and thermal isomerization studies, as well as molecular mechanics calculations. Bastadins 13 (11) and 19 (1a) exhibited moderate inhibition against Trypanosoma brucei and bastadin 4 (5) was cytotoxic to HCT-116 colon cancer cells.

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Section: Resultssupporting

confidence: 78%

Additional Insights on the Bastadins: Isolation of Analogues from the Sponge Ianthella cf. reticulata and Exploration of the Oxime Configurations

et al. 2010

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“…Recent examples of these activities include cytotoxicity, 3 selective binding to δ-opioid receptors, 4 inhibition of endothelial cell proliferation, 10, 11 angiogenesis 12 and inhibition of Ca 2+ release from the sarcoplasmic reticulum. 13 …”

mentioning

confidence: 99%

Lithothamnin A, the First Bastadin-like Metabolite from the Red Alga Lithothamnion fragilissimum

2011

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Lithothamnin A (1) is a new bastadin-like metabolite and represents the first report of this class of molecules from the red alga Lithothamnion fragilissimum. Lithothamnin A contains several novel structural features that distinguish it from other bastadins. These unique structural features include novel aromatic substitution patterns and the presence of a meta-meta linkage between aromatic rings, in addition to the meta-para linkage seen in the bastadins. Lithothamnin A is modestly cytotoxic in a panel of six human tumor cell lines.

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“…[9,13] In order to ascertain the position of the O -sulfate in 8 , the 13 C NMR chemical shifts of the latter were compared with those of 6 . [1,] As noted earlier by Ragan [14], Wright and co-workers[13] and others,[9] sulfation of a phenoxyl group leads to an upfield shift of the ipso 13 C signal by approximately Δδ 5 ppm and downfield shifts of ortho and para 13 C signals. The 13C NMR chemical shifts of bastadin-6 ( 6 ) were assigned by HMBC and HSQC and compared with those of 8 (Table 1 and Figure 5), and subjected to differential analysis.…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2018

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Bastadin-6-34-O-sulfate ester (8) was isolated from methanol extracts of Ianthella basta. The structure of 8 was characterized by analysis of MS and NMR data, and conversion through acid hydrolysis, to the parent compound, bastadin-6, which was identical by HPLC, MS and NMR with an authentic sample. An improved procedure for procurement of pure samples of bastadins-4 (4), -5 (5) and -6 (6) is described.

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

Cited by 14 publications

References 13 publications

Additional Insights on the Bastadins: Isolation of Analogues from the Sponge Ianthella cf. reticulata and Exploration of the Oxime Configurations

Additional Insights on the Bastadins: Isolation of Analogues from the Sponge Ianthella cf. reticulata and Exploration of the Oxime Configurations

Lithothamnin A, the First Bastadin-like Metabolite from the Red Alga Lithothamnion fragilissimum

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

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