Aromatic Secondary Metabolites from the Sponge Tedania ignis

Dillman, Rhonda L.; Cardellina, H I I John

doi:10.1021/np50076a021

Cited by 53 publications

(46 citation statements)

References 21 publications

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“…The presence of the two groups was also indicated by signals at δ 174.0 and 201.5 in the 13 C-NMR spectrum. The signals in the 1 H-and 13 C-NMR spectra arising from β-carboline nucleus (see Experimental section) were almost same to those of 1-acetyl-β-carboline (Dillman and Cardellina 1991). The 1 H-NMR spectrum indicated signals of two sets of triplets at δ 2.68 (2H, t, J = 6.5 Hz) and 3.56 (2H, t, J = 6.5 Hz), due to protons H-2' and H-3'.…”

Section: Resultsmentioning

confidence: 63%

Chemical Constituents of the Roots of Anemone altaica Fisch. ex C. A. Mey.

Zou

Dong

Yang

2005

J Integrative Plant Biology

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The roots of Anemone altaica Fisch. ex C. A. Mey. have been used in the treatment of epilepsia, neurasthenia, and arthritis in Chinese folk medicine for a long time. In order to find new and bioactive compounds, the chemical constituents of the roots of A. altaica were investigated and nine compounds were isolated from the EtOH extract of this plant. On the basis of spectroscopic methods, the structures of these compounds were elucidated as 4-(9H-β-carbolin-1-yl)-4-oxo-butyric acid (1), carboxymethyl isoferulate (2), isoferulic acid (3), cirsiumaldehyde (4), 5-hydroxy-4-oxo-pentanoic acid (5), triacontane (6), palmic acid (7), β-sitosterol (8), and daucosterol (9). Among them, 1 and 2 were new compounds, and 3 and 4 were obtained from this genus for the first time.

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Section: Resultsmentioning

confidence: 63%

Chemical Constituents of the Roots of Anemone altaica Fisch. ex C. A. Mey.

Zou

Dong

Yang

2005

J Integrative Plant Biology

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“…The 1-Acetyl-3-carboxy-β-carboline has previously only been found in plants [ 15 , 17 ], and this is the first report on the production of this compound by a bacterium. Conversely, 1-acetyl-β-carboline has previously been isolated from several types of organisms, including plants [ 14 , 18 ], a fungus [ 19 ], a sponge [ 20 ], and several bacteria e.g., [ 21 ].…”

Section: Resultsmentioning

confidence: 99%

Labradorins with Antibacterial Activity Produced by Pseudomonas sp.

et al. 2017

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The urgent need for new antibacterial drugs has led to renewed interest in microorganisms, which historically have been the main source of previously discovered antibiotics. The present study describes the discovery of two new antibacterial oxazolylindole type alkaloids, labradorins 5 (1) and 6 (2), which were isolated and characterized from two isolates of Pseudomonas sp., along with four previously known tryptophane derived alkaloids. The structures of 1 and 2 were determined by NMR spectroscopy and MS, and confirmed by synthesis. During bioassay-guided isolation using several human bacterial pathogens, 1 and 2 displayed activity towards Staphylococcus aureus and Acinetobacter baumannii. The minimal inhibitory concentrations (MIC) of compounds 1 and 2 against S. aureus were 12 μg·mL−1 and 50 μg·mL−1, respectively, whereas the MICs against A. baumannii were >50 μg·mL−1. The CC50 values of compound 1 towards a liver cell line (HEP-G2) and a T-cell line (MT4) were 30 μg·mL−1 and 20 μg·mL−1, respectively, and for compound 2 were >100 μg·mL−1 and 20 μg·mL−1, respectively. Due to the limited potency of compounds 1 and 2, along with their toxicity, the compounds do not warrant further development towards new antibiotics.

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“…Several indole alkaloid derivatives have been reported from different sponges, including Hyrtios , Sarcotragus, Tedania , and Dragmacidon . [ 20 21 22 23 ] Lately, the indole series of alkaloids have become an attractive research field for the development of new pharmacological lead compounds due to their interesting and diverse biological activities. [ 24 ]…”

Section: Resultsmentioning

confidence: 99%

Studies on the red sea sponge Haliclona sp. for its chemical and cytotoxic properties

et al. 2016

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Background:A great number of novel compounds with rich chemical diversity and significant bioactivity have been reported from Red Sea sponges.Objective:To isolate, identify, and evaluate the cytotoxic activity of the chemical constituents of a sponge belonging to genus Haliclona collected from the Eastern coast of the Red Sea.Materials and Methods:The total ethanolic extract of the titled sponge was subjected to intensive chromatographic fractionation and purification guided by cytotoxic bioassay toward various cancer cell lines. The structures of the isolated compounds were elucidated using spectroscopic techniques including one-dimension and two-dimension nuclear magnetic resonance, mass spectrometry, ultraviolet, and infrared data, as well as comparison with the reported spectral data for the known compounds. X-ray single-crystal structure determination was performed to determine the absolute configuration of compound 4. The screening of antiproliferative activity of the compounds was carried on three tumor cell lines, namely the human cervical cancer (HeLa), human hepatocellular carcinoma (HepG2), and human medulloblastoma (Daoy) cells using MTT assay.Results:This investigation resulted in the isolation of a new indole alkaloid, 1-(1H-indol-3-yloxy) propan-2-ol (1), with the previously synthesized pyrrolidine alkaloid, (2R, 3S, 4R, 5R) pyrrolidine-(1-hydroxyethyl)-3,4-diol hydrochloride (4), isolated here from a natural source for the first time. In addition, six known compounds tetillapyrone (2), nortetillapyrone (3), 2-methyl maleimide-5-oxime (5), maleimide-5-oxime (6), 5-(hydroxymethyl) dihydrofuran-2 (3H)-one (7), and ergosta-5,24 (28)-dien-3-ol (8) were also identified. Most of the isolated compounds exhibited weak cytotoxic activity against HepG-2, Daoy, and HeLa cancer cell lines.Conclusion:This is the first report of the occurrence of the indole and pyrrolidine alkaloids, 1-(1H-indol-2-yloxy) propan-2-ol (1), and the - (1-hydroxyethyl)-3,4-diol hydrochloride (4), in the Red Sea Haliclona sp.SUMMARY From the Red Sea Haliclona sp. two alkaloids with indole and pyrrolidine nuclei, 1-(1H-indol-2-yloxy) propan-2-ol-(1) and pyrrolidine-(1-hydroxyethyl)-3,4-diol hydrochloride (4) were isolated and fully characterized; in addition to six known compounds (2, 3, 5-8)The absolute configuration and the three-dimension stereo-molecular structure of compound 4 were determined by X-ray crystallographyThe different extracts and isolated compounds showed weak cytotoxic activity against HepG-2, Daoy, and HeLa cancer cell lines.

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Aromatic Secondary Metabolites from the Sponge Tedania ignis

Cited by 53 publications

References 21 publications

Chemical Constituents of the Roots of Anemone altaica Fisch. ex C. A. Mey.

Chemical Constituents of the Roots of Anemone altaica Fisch. ex C. A. Mey.

Labradorins with Antibacterial Activity Produced by Pseudomonas sp.

Studies on the red sea sponge Haliclona sp. for its chemical and cytotoxic properties

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