TY - JOUR
T1 - Callyspongisines A-D
T2 - Bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp.
AU - Plisson, Fabien
AU - Prasad, Pritesh
AU - Xiao, Xue
AU - Piggott, Andrew M.
AU - Huang, Xiao Cong
AU - Khalil, Zeinab
AU - Capon, Robert J.
PY - 2014/3/14
Y1 - 2014/3/14
N2 - An extract of the Great Australian Bight marine sponge Callyspongia sp. (CMB-01152) displayed inhibitory activity against the neurodegenerative disease kinase targets casein kinase 1 (CK1), cyclin-dependent kinase 5 (CDK5) and glycogen synthase kinase 3 (GSK3β). Chemical investigation, employing HPLC-DAD-MS single ion extraction protocols, facilitated identification of the new bromopyrrole alkaloids, callyspongisines A-D (1-4), and two known co-metabolites, hymenialdisine (5) and 2-bromoaldisine (6). Structure elucidation of 1-6 was supported by detailed spectroscopic analysis and chemical interconversion, as well as biosynthetic and synthetic considerations. Callyspongisine A (1) is only the second reported example of a natural imino-oxazoline, and the first to feature a spiro heterocyclic framework, while callyspongisines B-D (2-4) were speculated to be storage and handling artefacts of 1. The kinase inhibitory activity detected in Callyspongia sp. (CMB-01152) was attributed to 5.
AB - An extract of the Great Australian Bight marine sponge Callyspongia sp. (CMB-01152) displayed inhibitory activity against the neurodegenerative disease kinase targets casein kinase 1 (CK1), cyclin-dependent kinase 5 (CDK5) and glycogen synthase kinase 3 (GSK3β). Chemical investigation, employing HPLC-DAD-MS single ion extraction protocols, facilitated identification of the new bromopyrrole alkaloids, callyspongisines A-D (1-4), and two known co-metabolites, hymenialdisine (5) and 2-bromoaldisine (6). Structure elucidation of 1-6 was supported by detailed spectroscopic analysis and chemical interconversion, as well as biosynthetic and synthetic considerations. Callyspongisine A (1) is only the second reported example of a natural imino-oxazoline, and the first to feature a spiro heterocyclic framework, while callyspongisines B-D (2-4) were speculated to be storage and handling artefacts of 1. The kinase inhibitory activity detected in Callyspongia sp. (CMB-01152) was attributed to 5.
UR - http://www.scopus.com/inward/record.url?scp=84893942876&partnerID=8YFLogxK
U2 - 10.1039/c4ob00091a
DO - 10.1039/c4ob00091a
M3 - Article
C2 - 24458130
AN - SCOPUS:84893942876
SN - 1477-0520
VL - 12
SP - 1579
EP - 1584
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 10
ER -