ChemInform Abstract: Chemoenzymatic Synthesis of (+)-Docosa-4,15-dien-1-yn-3-ol, a Component of the Marine Sponge Cribrochalina vasculum, and Confirmation of the Structure and Absolute Configuration of the Acetylenic Alcohol, by Lipase-Catalyzed Biotransf

Seven compounds (1-7) were isolated from the marine sponge Aaptos aaptos living in the Vietnamese sea. Their structures were determined as 2 hours, 5 H,7 H,9 H-9 S-hydroxy-imidazo[1,5- α]pyridine-1,3-dione (1), 3-([9-methylhexadecyl]oxy)propane-1,2-diol 2, 2,3-dihydro-2,3-dioxoaaptamine (3), indol-3-aldehyde (4), methyl indole-3-carboxylate (5) 4-hydroxy-5-(indole-3-yl)−5-oxo-pentan-2-one (6), and thymidine (7) by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of the spectral data with those reported in the literature. In addition, the absolute configuration of 1 was determined from the experimental ECD spectrum and comparison of this with the theoretical ECD calculations using the TDDFT method. Compounds 1 and 2 were isolated from nature for the first time. Compound 3 induced cytotoxic activity against SK-LU-1, MCF-7, HepG2, and SK-Mel-2 cell lines with IC50 values of 41.27 ± 2.63, 40.70 ± 2.65, 34.31 ± 3.43, and 36.63 ± 1.40 µM, respectively.

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Asymmetric Total Synthesis of 16-Methyleicos-(4E )-en-1-yn-3-ol from the Marine Sponge Cribrochalina vasculum : Establishment of Absolute Configuration of Chiral Centers

ChemistrySelect ◽

10.1002/slct.201803646 ◽

2019 ◽

Vol 4 (1) ◽

pp. 399-402 ◽

Cited By ~ 1

Author(s):

Narayana Rao Gundoju ◽

Ramesh Bokam ◽

Nageswara Rao Yalavarthi ◽

Karimulla Shaik ◽

Mangala Gowri Ponnapalli

Keyword(s):

Total Synthesis ◽

Absolute Configuration ◽

Marine Sponge ◽

Asymmetric Total Synthesis ◽

Chiral Centers

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Sponge-Derived 24-Homoscalaranes as Potent Anti-Inflammatory Agents

Marine Drugs ◽

10.3390/md18090434 ◽

2020 ◽

Vol 18 (9) ◽

pp. 434

Author(s):

Bo-Rong Peng ◽

Kuei-Hung Lai ◽

Yu-Chia Chang ◽

You-Ying Chen ◽

Jui-Hsin Su ◽

...

Keyword(s):

Absolute Configuration ◽

Marine Sponge ◽

Therapeutic Potential ◽

Current Work ◽

Superoxide Anions ◽

Cancer Treatments ◽

Electronic Circular Dichroism ◽

Spectroscopic Analyses ◽

Anti Inflammatory ◽

New Metabolites

Scalarane-type sesterterpenoids are known for their therapeutic potential in cancer treatments. However, the anti-inflammatory properties of this class of metabolites remain elusive. Our current work aimed to investigate the anti-inflammatory scalaranes from marine sponge Lendenfeldia sp., resulting in the isolation of six new 24-homoscalaranes, lendenfeldaranes E–J (1–6). The structures of the new metabolites were determined by extensive spectroscopic analyses, and the absolute configuration of 1 was established by electronic circular dichroism (ECD) calculations. Compounds 2 and 3 were discovered to individually reduce the generation of superoxide anions, and compound 1 displayed an inhibitor effect on the release of elastase. These three compounds were proven to be the first anti-neutrophilic scalaranes.

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