Synthesis and Absolute Configuration of Acanthodendrilline, a New Cytotoxic Bromotyrosine Alkaloid from the Thai Marine Sponge Acanthodendrilla sp.

Nachanun Sirimangkalakitti; Masashi Yokoya; Supakarn Chamni; Pithi Chanvorachote; Anuchit Plubrukrn; Naoki Saito; Khanit Suwanborirux

doi:10.1248/cpb.c15-00901

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Synthesis and Absolute Configuration of Acanthodendrilline, a New Cytotoxic Bromotyrosine Alkaloid from the Thai Marine Sponge Acanthodendrilla sp.

Nachanun Sirimangkalakitti, Masashi Yokoya, Supakarn Chamni, Pithi Chanvorachote, Anuchit Plubrukrn, Naoki Saito , Khanit Suwanborirux

Author information

Nachanun Sirimangkalakitti
Center for Bioactive Natural Products from Marine Organisms and Endophytic Fungi (BNPME), Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University
Masashi Yokoya
Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University
Supakarn Chamni
Center for Bioactive Natural Products from Marine Organisms and Endophytic Fungi (BNPME), Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University
Pithi Chanvorachote
Cell-Based Drug and Health Product Development Research Unit and Department of Pharmacology and Physiology, Faculty of Pharmaceutical Sciences, Chulalongkorn University
Anuchit Plubrukrn
Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University
Naoki Saito Corresponding author
Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University
Khanit Suwanborirux
Center for Bioactive Natural Products from Marine Organisms and Endophytic Fungi (BNPME), Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University

Keywords: bromotyrosine alkaloid, absolute configuration, asymmetric synthesis, cytotoxicity, Acanthodendrilla sp.

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Supplementary material

2016 Volume 64 Issue 3 Pages 258-262

DOI https://doi.org/10.1248/cpb.c15-00901

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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.

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