Antineoplastic diterpene-benzoate macrolides from the fijian red alga Callophycus serratus

Julia Kubanek; Anne C. Prusak; Terry W. Snell; Rachel A. Giese; Kenneth I. Hardcastle; Craig R. Fairchild; William Aalbersberg; Carmen Raventos-Suarez; Mark E. Hay

doi:10.1021/ol052121f

Antineoplastic diterpene-benzoate macrolides from the fijian red alga Callophycus serratus

Julia Kubanek, Anne C. Prusak, Terry W. Snell, Rachel A. Giese, Kenneth I. Hardcastle, Craig R. Fairchild, William Aalbersberg, Carmen Raventos-Suarez, Mark E. Hay

Research output: Contribution to journal › Article › peer-review

Abstract

(Chemical Equation Presented) 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.

Original language	English (US)
Pages (from-to)	5261-5264
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	23
DOIs	https://doi.org/10.1021/ol052121f
State	Published - Nov 10 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol052121f

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title = "Antineoplastic diterpene-benzoate macrolides from the fijian red alga Callophycus serratus",

abstract = "(Chemical Equation Presented) 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.",

author = "Julia Kubanek and Prusak, {Anne C.} and Snell, {Terry W.} and Giese, {Rachel A.} and Hardcastle, {Kenneth I.} and Fairchild, {Craig R.} and William Aalbersberg and Carmen Raventos-Suarez and Hay, {Mark E.}",

year = "2005",

month = nov,

day = "10",

doi = "10.1021/ol052121f",

language = "English (US)",

volume = "7",

pages = "5261--5264",

journal = "Organic Letters",

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T1 - Antineoplastic diterpene-benzoate macrolides from the fijian red alga Callophycus serratus

AU - Kubanek, Julia

AU - Prusak, Anne C.

AU - Snell, Terry W.

AU - Giese, Rachel A.

AU - Hardcastle, Kenneth I.

AU - Fairchild, Craig R.

AU - Aalbersberg, William

AU - Raventos-Suarez, Carmen

AU - Hay, Mark E.

PY - 2005/11/10

Y1 - 2005/11/10

N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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.

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Antineoplastic diterpene-benzoate macrolides from the fijian red alga Callophycus serratus

Abstract

ASJC Scopus subject areas

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