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PMID: 16268553 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't

Antineoplastic diterpene-benzoate macrolides from the Fijian red alga Callophycus serratus.

Organic letters ·Vol. 7 ·No. 23 ·2005-11-10 ·Pages 5261-4

Kubanek J, Prusak AC, Snell TW, Giese RA, Hardcastle KI, Fairchild CR, Aalbersberg W, Raventos-Suarez C, Hay ME

Abstract

[structures: see text] Three diterpene-benzoate natural products, with novel carbon skeletons and an unusual proposed biosynthesis, were isolated from extracts of the Fijian red alga Callophycus serratus and identified by a combination of X-ray crystallographic, NMR, and mass spectral analyses. Bromophycolide A (1) displayed cytotoxicity against several human tumor cell lines via specific apoptotic cell death. This represents the first discovery of natural products incorporating a diterpene and benzoate skeleton into a macrolide system.

MeSH Terms
Anti-Bacterial Agents/chemistry,isolation & purification,pharmacology Anti-HIV Agents/chemistry,isolation & purification,pharmacology Antineoplastic Agents/chemistry,isolation & purification,pharmacology Benzoates/chemistry,isolation & purification,pharmacology Diterpenes/chemistry,isolation & purification,pharmacology Drug Resistance, Bacterial Drug Screening Assays, Antitumor Fiji Humans Macrolides/chemistry,isolation & purification,pharmacology Microbial Sensitivity Tests Molecular Structure Nuclear Magnetic Resonance, Biomolecular Rhodophyta/chemistry Tumor Cells, Cultured
Chemicals
Anti-Bacterial Agents Anti-HIV Agents Antineoplastic Agents Benzoates Diterpenes Macrolides bromophycolide A
Authors & Affiliations
9 authors, click to expand affiliations / ORCID
Kubanek Julia
School of Biology and School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, USA. julia.kubanek@biology.gatech.edu
Prusak Anne C
Snell Terry W
Giese Rachel A
Hardcastle Kenneth I
Fairchild Craig R
Aalbersberg William
Raventos-Suarez Carmen
Hay Mark E
References (5)
5 references, click to expand
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  4. Tolypodiol, an antiinflammatory diterpenoid from the cyanobacterium Tolypothrix nodosa.
    J Nat Prod. 1996 Aug;59(8):786-8 PMID: 8792625
  5. Distribution of bromophenols in species of marine algae from eastern Australia.
    J Agric Food Chem. 1999 Jun;47(6):2367-73 PMID: 10794638
Article Info
Journal
Organic letters
Abbr.
Org Lett
ISSN
1523-7060
Published
2005-11-10
Pages
5261-4
Language
English
Region
United States
NLM ID
100890393
PMCID
PMC3374863
Subset
IM
Grants
FIC NIH HHS · U01 TW007401 · United States
FIC NIH HHS · U19 TW007401 · United States
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