title: Studies on the Red Sea Sponge Haliclona sp. for its Chemical and Cytotoxic Properties.
abstract: 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.
  
  
  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.
  
  
  CONCLUSIONS
  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.
  
  
  CONCLUSIONS
  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.
authors.affiliation: Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
authors.forename: Shaza Mohamed
authors.initials: SM
authors.lastname: Al-Massarani
authors.affiliation: Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia; Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, El-Mansoura 35516, Egypt.
authors.forename: Ali Ali
authors.initials: AA
authors.lastname: El-Gamal
authors.affiliation: Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
authors.forename: Mansour Sulaiman
authors.initials: MS
authors.lastname: Al-Said
authors.affiliation: Department of Pharmacognosy, College of Pharmacy, Sattam Bin Abdulaziz University, Al-kharj 11942, Saudi Arabia; Department of Pharmacognosy, College of Pharmacy, Alexandria University, Alexandria 21215, Egypt.
authors.forename: Maged S
authors.initials: MS
authors.lastname: Abdel-Kader
authors.affiliation: Department of Pharmacology and Toxicology, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
authors.forename: Abdelkader E
authors.initials: AE
authors.lastname: Ashour
authors.affiliation: Vitiligo Research Chair, College of Medicine, King Saud University, Riyadh, Saudi Arabia.
authors.forename: Ashok
authors.initials: A
authors.lastname: Kumar
authors.affiliation: Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia; Department of Pharmacognosy, Faculty of Pharmacy, Assiut University 71526, Assiut, Egypt.
authors.forename: Wael M
authors.initials: WM
authors.lastname: Abdel-Mageed
authors.affiliation: Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
authors.forename: Adnan Jathlan
authors.initials: AJ
authors.lastname: Al-Rehaily
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
authors.forename: Hazem A
authors.initials: HA
authors.lastname: Ghabbour
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
authors.forename: Hoong-Kun
authors.initials: HK
authors.lastname: Fun
keywords: 5-(hydroxymethyl) dihydrofuran-2 (3H)-one; Haliclona sp.; indole alkaloid; maleimide-5-oxime; pyrrolidine alkaloid