NMR Characterization of Rearranged Staurosporine Aglycone Analogues from the Marine Sponge Damiria sp.

Trong D Tran; Laura K Cartner; Heidi R Bokesch; Curtis J Henrich; Xin W Wang; Chulabhorn Mahidol; Somsak Ruchirawat; Prasat Kittakoop; Barry R O'Keefe; Kirk R Gustafson

doi:10.1002/mrc.4932

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NMR Characterization of Rearranged Staurosporine Aglycone Analogues from the Marine Sponge Damiria sp.

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NMR Characterization of Rearranged Staurosporine Aglycone Analogues from the Marine Sponge Damiria sp.

Trong D Tran, Laura K Cartner, Heidi R Bokesch, Curtis J Henrich, Xin W Wang, Chulabhorn Mahidol, Somsak Ruchirawat, Prasat Kittakoop, Barry R O'Keefe and Kirk R Gustafson

Magnetic Resonance in Chemistry, Vol.59(5), pp.534-539

2021

DOI: https://doi.org/10.1002/mrc.4932

PMID: 31379005

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Abstract

Medicinal and Biomolecular Chemistry

Physical Chemistry (incl. Structural)

Indolocarbazole

LR-HSQMBC

Damiria

damirine

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.

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Title: NMR Characterization of Rearranged Staurosporine Aglycone Analogues from the Marine Sponge Damiria sp.
Authors: Trong D Tran (Author) - University of the Sunshine Coast
Laura K Cartner (Author) - Centre of Cancer Research, United States
Heidi R Bokesch (Author) - Centre of Cancer Research, United States
Curtis J Henrich (Author) - Centre of Cancer Research, United States
Xin W Wang (Author) - Centre of Cancer Research, United States
Chulabhorn Mahidol (Author) - Chulabhorn Research Institute, Thailand
Somsak Ruchirawat (Author) - Chulabhorn Research Institute, Thailand
Prasat Kittakoop (Author) - Chulabhorn Research Institute, Thailand
Barry R O'Keefe (Author) - Centre of Cancer Research, United States
Kirk 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
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

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