title: Synthesis and Absolute Configuration of Acanthodendrilline, a New Cytotoxic Bromotyrosine Alkaloid from the Thai Marine Sponge Acanthodendrilla sp.
abstract: Acanthodendrilline (1), a new bromotyrosine alkaloid, was isolated from the Thai marine sponge Acanthodendrilla sp. The structure of 1 was fully characterized by spectroscopic analysis, in agreement with the synthesized compound used to resolve the single chiral center at C-11. Total synthesis of the enantiomers of 1 allowed for the comparison of specific rotation values and hence the determination of the absolute configuration as 11-S. Cytotoxicity evaluation revealed that (S)-1 exhibited approximately three-fold more potent cytotoxicity against the human non-small cell lung cancer H292 cell line than (R)-1.
authors.affiliation: Center for Bioactive Natural Products from Marine Organisms and Endophytic Fungi (BNPME), Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University.
authors.forename: Nachanun
authors.initials: N
authors.lastname: Sirimangkalakitti
authors.forename: Masashi
authors.initials: M
authors.lastname: Yokoya
authors.forename: Supakarn
authors.initials: S
authors.lastname: Chamni
authors.forename: Pithi
authors.initials: P
authors.lastname: Chanvorachote
authors.forename: Anuchit
authors.initials: A
authors.lastname: Plubrukrn
authors.forename: Naoki
authors.initials: N
authors.lastname: Saito
authors.forename: Khanit
authors.initials: K
authors.lastname: Suwanborirux
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002219:Carbamates / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D023303:Oxazolidinones / Q000494:pharmacology*; D011161:Porifera / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D002219:Carbamates; D023303:Oxazolidinones; C000611966:acanthodendrilline