Spiralisones A-D: acylphloroglucinol hemiketals from an Australian marine brown alga, Zonaria spiralis

Zhang, Hua, Xiao, Xue, Conte, Melissa M., Khalil, Zeinab and Capon, Robert J. (2012) Spiralisones A-D: acylphloroglucinol hemiketals from an Australian marine brown alga, Zonaria spiralis. Organic and Biomolecular Chemistry, 10 48: 9671-9676. doi:10.1039/c2ob26988k


Author Zhang, Hua
Xiao, Xue
Conte, Melissa M.
Khalil, Zeinab
Capon, Robert J.
Title Spiralisones A-D: acylphloroglucinol hemiketals from an Australian marine brown alga, Zonaria spiralis
Formatted title
Spiralisones A-D: acylphloroglucinol hemiketals from an Australian marine brown alga, Zonaria spiralis
Journal name Organic and Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
1477-0539
Publication date 2012-01
Sub-type Article (original research)
DOI 10.1039/c2ob26988k
Open Access Status Not Open Access
Volume 10
Issue 48
Start page 9671
End page 9676
Total pages 6
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Collection year 2013
Language eng
Formatted abstract
An intertidal sample of the Australian marine brown alga, Zonaria spiralis, exhibited promising kinase inhibitory and antibacterial activity. Chemical analysis returned six phloroglucinol-derived lipids, the new hemiketal spiralisones A–D (1–4) and the known chromones 5–6, and the known norsesquiterpenoid apo-9′-fucoxanthinone (7). Structures 1–7 were assigned on the basis of detailed spectroscopic analysis, biosynthetic considerations and total synthesis. Spiralisones undergo facile acid-mediated dehydration to yield the corresponding chromones, revealing for the first time that brown algal chromones may be handling artifacts rather than natural products. Hemiketals 1 and 2, and chromone 6, displayed inhibitory activity against the neurodegenerative disease kinase targets CDK5/p25, CK1δ and GSK3β, while hemiketals 1, 3 and 4, and chromone 6, displayed growth inhibitory activity against the Gram-positive bacteria Bacillus subtilis (ATCC 6051 and 6633). The promising kinase inhibitory and antibacterial properties of the Z. spiralis extract were attributed to the cumulative effect of many moderately potent phloroglucinol-derived lipid co-metabolites.
Keyword Bace inhibitors
Ianthella Sp
Tournefortii
Sponge
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
Institute for Molecular Bioscience - Publications
 
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