Studies on the Red Sea Sponge Haliclona sp. for its Chemical and Cytotoxic Properties.

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.

Phytochemical and biological evaluation of Buddleja polystachya growing in Saudi Arabia.

Several Buddleja species were the target of phytochemical and biological studies; however, nothing was reported concerning the chemistry of Buddleja polystachya Fresen. growing in Saudi Arabia. Sixteen constituents were isolated from the aerial parts of B. polystachya using various chromatographic techniques and were identified by the help of different spectral techniques including 1D, 2D NMR and mass spectrometry. Moreover, the different fractions were evaluated for their anti-inflammatory and hypoglycemic activities. The isobenzofuranone derivative (4-hydroxy-7-methylisobenzofuranone) (4), has been isolated for the first time from this natural source, B. polystachya, along with fifteen known compounds namely; phenolic fatty acid ester, 1'(4-hydroxyphenyl) ethanol ester of docosanoic (1), uvaol (2), sakuranetin (3), kumatakenin (5), cirsimaritin (6), 5-hydroxy-3,7,4'-trimethoxyflavone (7), oleanolic acid (8), herbacetin 3,7,8-trimethyl ether (9), ursolic acid (10), verbascoside (11), linarin (12), luteolin 7-O-ß-D-glucoside (13), luteolin 7-(6"-caffeoyl)-O-ß-D-glucopyranoside (14), luteolin (15), and 6-O-α-L-(4''-O-trans-cinnamoyl) rhamnopyranosylcatalpol (16). Regarding the biological activities investigated, the ethyl acetate fraction showed the most significant anti-inflammatory activity, followed by the n-butanol and the aqueous fractions. As for the petroleum ether and dichloromethane fractions, their anti-inflammatory effects were moderate. The highest hypoglycemic activity was possessed by the ethyl acetate fraction, followed by the dichloromethane fraction and the n-butanol fraction showed the weakest activity.

A novel ß-lactam derivative, albactam from the flowers of Albizia lebbeck with platelets anti-aggregatory activity in vitro.

A novel ß-lactam derivative, albactam, was isolated from the alcoholic extract of the flowers of Albizia lebbeck. It showed a significant anti-aggregatory activity against adenosine diphosphate and arachidonic acid induced guinea-pigs' platelets aggregation in vitro. Six more known compounds were also isolated and fully characterized by measuring 1D and 2D NMR, two of them are the triterpenes ß-amyrin and 11α, 12α-oxidotaraxerol, two ceramide derivatives and two flavonoids, kampferol 3-O-rutinoside and rutin.

Prenylbicyclogermacrane diterpenoids from the formosan soft coral Nephthea elongata.

Seven new prenylbicyclogermacrane diterpenoids, pacificins K--Q (1--7), were isolated from the methylene chloride solubles of the Formosan soft coral Nephthea elongata. Their structures were elucidated by extensive spectroscopic analysis and their cytotoxicity against selected cancer cells was measured in vitro.

New cadinene sesquiterpenoids from the Formosan soft coral Xenia puerto-galerae.

Six new cadinene sesquiterpenoids, xenitorins A-F (1-6), were isolated from the methylene chloride solubles of the Formosan soft coral Xenia puerto-galerae. The structures were elucidated by 1D and 2D NMR spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.

New cytotoxic xenia diterpenoids from the Formosan soft coral Xenia umbellata.

Seven new cytotoxic xenicane-type diterpenoids, 9-deoxyxeniloide-E (1), 9-deoxy-7,8-epoxyxeniloide-E (2), xeniolide-G (3), 9-deoxyxenialactol-C (4), xenibecin (5), xeniolide-H (6), and xenitacin (7), were isolated from the methylene chloride solubles of the Formosan soft coral Xenia umbellata. The structures were elucidated by 1D and 2D NMR spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.

New cytotoxic constituents from the Formosan soft corals Clavularia viridis and Clavularia violacea.

Three new cytotoxic prostanoids, claviridenone E-G (1-3), and three new cytotoxic steroids, stoloniferone E-G (4-6), were isolated from the methylene chloride solubles of the Formosan soft coral Clavulariaviridis. A cytotoxic cembranoid, claviolide (7), was isolated from the methylene chloride solubles of the Formosan soft coral Clavularia violacea. The structures were elucidated by 1D and 2D NMR spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.

Novel terpenoids from the formosan soft coral Cespitularia hypotentaculata.

Four new cytotoxic diterpenes, cespitularins A-D (1-4), having the verticillane skeleton, a new cytotoxic norditerpene, cesputularin E (5), that possesses a novel norverticillane skeleton, and three new diterpenes, cespitularins F-H (6-8), possessing a novel carbon skeleton named cespitularane, were isolated from the methylene chloride solubles of the Formosan soft coral Cespitularia hypotentaculata. The structures of cespitularins A-H (1-8) were elucidated by 1D and 2D NMR spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.