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Planta Med 2016; 82(09/10): 910-918
DOI: 10.1055/s-0042-108204
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Marine Bacteria, XLVII[*] – Psychrotolerant Bacteria from Extreme Antarctic Habitats as Producers of Rare Bis- and Trisindole Alkaloids

Vimal Nair
1   Institute of Organic and Biomolecular Chemistry, University of Göttingen, Göttingen, Germany
,
Imelda Schuhmann
1   Institute of Organic and Biomolecular Chemistry, University of Göttingen, Göttingen, Germany
,
Heidrun Anke
2   Institute of Biotechnology and Drug Research, Kaiserslautern, Germany
,
Gerhard Kelter
3   Oncotest GmbH, Freiburg, Germany
,
Heinz-Herbert Fiebig
3   Oncotest GmbH, Freiburg, Germany
,
Elisabeth Helmke
4   Alfred Wegener Institute for Polar and Marine Research, Bremerhaven, Germany
,
Hartmut Laatsch
1   Institute of Organic and Biomolecular Chemistry, University of Göttingen, Göttingen, Germany
› Institutsangaben
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Publikationsverlauf

received 14. Januar 2016
revised 13. April 2016

accepted 21. April 2016

Publikationsdatum:
10. Juni 2016 (online)

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Abstract

From the gastrointestinal tract of a fish dredged near the South Orkney Islands in Antarctica, we isolated the psychrotolerant bacterial strain T262, which belongs to the species Vibrio splendidus. Investigation of this strain led to the isolation of a series of 15 bis- and trisindole derivatives. Among them, six new indole alkaloids, namely, turbomycin C [4′-n-butoxyphenyl-bis(1H-indol-3-yl)methane, 1a], turbomycin D [4′-n-propoxyphenyl-bis(1H-indol-3-yl)methane, 1b], turbomycin E [4′-ethoxyphenyl-bis(1H-indol-3-yl)methane, 1c], turbomycin F [4′-methoxy-3′,5′-dinitrophenyl-bis(1H-indol-3-yl)methane, 2], trisindolal (3a), and 4-(1H-indol-3-yl-sulfanyl)phenol (4). Another new bisindole derivative elucidated as 2-(indol-3-ylmethyl)-indol-3-ylethanol (7a) was obtained together with six known compounds from the psychrotolerant Arthrobacter psychrochitiniphilus strain T406, isolated from the excrement of penguins. Some of the isolated compounds showed activity against both gram-positive and gram-negative bacteria at 10 µg/paper disk. Trisindolal (3a) was active against the peronosporomycetes Botrytis cinerea and Phytophthora infestans, and some of the indole derivatives indicated promising cytotoxicity towards human tumor cell lines. By exhibiting a mean IC50 of 0.45 µg/mL (1.17 µM), trisindolal (3a) showed pronounced potency and selectivity in a panel of 11 human tumor cell lines derived from 10 different tumor histotypes.

Key words

Vibrio splendidus - Vibrionaceae - Arthrobacter psychrochitiniphilus - Micrococcaceae - trisindoles - bisindoles - Antarctic bacteria - psychrotolerant bacteria

* Marine Bacteria, XLVI: Xie Z, Liu B, Wang H, Yang S, Zhang H, Wang Y, Ji N, Qin S, Laatsch H. Kiamycin, a unique cytotoxic angucyclinone derivative from a marine Streptomyces sp. Marine Drugs 2012; 10: 551–558


Supporting Information

 

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