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• Sangnoi, Y
• Sakulkeo, O
• Yuenyongsawad, S
• Kanjana-opas, A
• Ingkaninan, K
• Plubrukarn, A
• Suwanborirux, K
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• Sangnoi, Y
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Mar. Drugs 2008, 6(4), 578-586; doi:10.3390/md6040578

Article

Acetylcholinesterase-Inhibiting Activity of Pyrrole Derivatives from a Novel Marine Gliding Bacterium, Rapidithrix thailandica

Yutthapong Sangnoi ¹ , Oraphan Sakulkeo ² , Supreeya Yuenyongsawad ² , Akkharawit Kanjana-opas ^1,4 , Kornkanok Ingkaninan ^3,4 , Anuchit Plubrukarn ^2,4,*  and Khanit Suwanborirux ⁴

¹ Department of Industrial Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, Hat-Yai, Songkla 90112, Thailand ² Marine Natural Products Research Unit, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand ³ Department of Pharmaceutical Chemistry and Pharmacognosy, Faculty of Pharmaceutical Sciences, Naresuan University, Phitsanulok 65000, Thailand ⁴ Center for Bioactive Natural Products from Marine Organisms and Endophytic Fungi (BNPME), Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Patumwan, Bangkok 10330, Thailand

* Author to whom correspondence should be addressed.

Received: 2 September 2008; in revised form: 3 October 2008 / Accepted: 8 October 2008 / Published: 13 October 2008

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Abstract: Acetylcholinesterase-inhibiting activity of marinoquinoline A (1), a new pyrroloquinoline from a novel species of a marine gliding bacterium Rapidithrix thailandica, was assessed (IC₅₀ 4.9 μM). Two related pyrrole derivatives, 3-(2'-aminophenyl)-pyrrole (3) and 2,2-dimethyl-pyrrolo-1,2-dihydroquinoline (4), were also isolated from two other strains of R. thailandica. The isolation of 3 from a natural source is reported here for the first time. Compound 4 was proposed to be an isolation artifact derived from 3. The two isolated compounds were virtually inactive in the acetylcholinesterase-inhibitory assay (enzyme inhibition < 30% at 0.1 g L^-1).

Keywords: pyrroloquinolines; phenylpyrroles; gliding bacteria; Rapidithrix thailandica; acetylcholinesterase inhibitors

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