Journal article
NMR Characterization of Rearranged Staurosporine Aglycone Analogues from the Marine Sponge Damiria sp.
Magnetic Resonance in Chemistry, Vol.59(5), pp.534-539
2021
PMID: 31379005
Abstract
The indolocarbazole family of bisindole alkaloids is best known for the natural product staurosporine, a protein kinase C inhibitor that belongs to the indolo[2,3-a]carbazole structural class. A large number of other indolo[2,3-a]carbazoles have subsequently been isolated and identified, but other isomeric forms of indolocarbazole natural products have rarely been reported. An extract of the marine sponge Damiria sp., which represents an understudied genus, provided two novel alkaloids named damirines A (1) and B (2). Their structures were assigned by comprehensive NMR spectroscopic analyses, and for compound 2 this included application of the LR-HSQMBC pulse sequence, a long-range heteronuclear correlation experiment that has particular utility for defining proton-deficient scaffolds. The damirines represent a new hexacyclic carbon-nitrogen framework comprised of an indolo[3,2-a]carbazole fused with either an aminoimidazole or a imidazolone ring. Compound 1 showed selective cytotoxic properties toward six different cell lines in the NCI-60 cancer screen.
Details
- Title
- NMR Characterization of Rearranged Staurosporine Aglycone Analogues from the Marine Sponge Damiria sp.
- Authors
- Trong D Tran (Author) - University of the Sunshine CoastLaura K Cartner (Author) - Centre of Cancer Research, United StatesHeidi R Bokesch (Author) - Centre of Cancer Research, United StatesCurtis J Henrich (Author) - Centre of Cancer Research, United StatesXin W Wang (Author) - Centre of Cancer Research, United StatesChulabhorn Mahidol (Author) - Chulabhorn Research Institute, ThailandSomsak Ruchirawat (Author) - Chulabhorn Research Institute, ThailandPrasat Kittakoop (Author) - Chulabhorn Research Institute, ThailandBarry R O'Keefe (Author) - Centre of Cancer Research, United StatesKirk R Gustafson (Corresponding Author) - Centre of Cancer Research, United States
- Publication details
- Magnetic Resonance in Chemistry, Vol.59(5), pp.534-539
- Publisher
- John Wiley & Sons Ltd.
- Date published
- 2021
- DOI
- 10.1002/mrc.4932
- ISSN
- 0749-1581; 1097-458X; 0749-1581
- PMID
- 31379005
- Copyright note
- Copyright (c) 2019. This is the peer reviewed version of the following article: Tran, TD, Cartner, LK, Bokesch, HR, et al. NMR characterization of rearranged staurosporine aglycone analogues from the marine sponge Damiria sp. Magn Reson Chem. 2021; 59:5, 534-539. https://doi.org/10.1002/mrc.4932, which has been published in final form at https://doi.org/10.1002/mrc.4932. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
- Organisation Unit
- School of Science and Engineering - Legacy; University of the Sunshine Coast, Queensland; School of Science, Technology and Engineering; Centre for Bioinnovation
- Language
- English
- Record Identifier
- 99451229702621
- Output Type
- Journal article
- Research Statement
- false
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