New norditerpenoids and a diterpenoid from a sponge that inhibit the lyase activity of DNA polymerase β

V. S.Prakash Chaturvedula; Zhijie Gao; Shannon H. Thomas; Sidney M. Hecht; David G.I. Kingston

doi:10.1016/j.tet.2004.08.017

New norditerpenoids and a diterpenoid from a sponge that inhibit the lyase activity of DNA polymerase β

V. S.Prakash Chaturvedula, Zhijie Gao, Shannon H. Thomas, Sidney M. Hecht, David G.I. Kingston

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

14 Scopus citations

Abstract

Using an assay to detect inhibitors of the lyase activity of DNA polymerase β, bioassay-directed fractionation of a CHCl ₃ extract of an unidentified sponge of the family Demospongiae resulted in the isolation of the new diterpenoid 1, the new bis-norditerpenoids 2-3, and the two known compounds spongia-13(16),14-dien-19-oic acid (4), and methylspongia-13(16),14-dien-19-oate (5). The structures of the new compounds were established on the basis of extensive 1D and 2D NMR spectroscopic interpretation. All five compounds inhibited the lyase activity of DNA polymerase β. Bioassay-directed fractionation of a CHCl ₃ extract of an unidentified sponge of the family Demospongiae resulted in the isolation of the new diterpenoid 1, the new bis-norditerpenoids 2-3, and two known compounds. All the isolated compounds were weak inhibitors of the lyase activity of DNA polymerase β.

Original language	English (US)
Pages (from-to)	9991-9995
Number of pages	5
Journal	Tetrahedron
Volume	60
Issue number	44
DOIs	https://doi.org/10.1016/j.tet.2004.08.017
State	Published - Oct 25 2004
Externally published	Yes

Keywords

Bioactivity
DNA polymerase β
Diterpenoid
Marine
Sponge

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2004.08.017

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title = "New norditerpenoids and a diterpenoid from a sponge that inhibit the lyase activity of DNA polymerase β",

abstract = "Using an assay to detect inhibitors of the lyase activity of DNA polymerase β, bioassay-directed fractionation of a CHCl 3 extract of an unidentified sponge of the family Demospongiae resulted in the isolation of the new diterpenoid 1, the new bis-norditerpenoids 2-3, and the two known compounds spongia-13(16),14-dien-19-oic acid (4), and methylspongia-13(16),14-dien-19-oate (5). The structures of the new compounds were established on the basis of extensive 1D and 2D NMR spectroscopic interpretation. All five compounds inhibited the lyase activity of DNA polymerase β. Bioassay-directed fractionation of a CHCl 3 extract of an unidentified sponge of the family Demospongiae resulted in the isolation of the new diterpenoid 1, the new bis-norditerpenoids 2-3, and two known compounds. All the isolated compounds were weak inhibitors of the lyase activity of DNA polymerase β.",

keywords = "Bioactivity, DNA polymerase β, Diterpenoid, Marine, Sponge",

author = "Chaturvedula, {V. S.Prakash} and Zhijie Gao and Thomas, {Shannon H.} and Hecht, {Sidney M.} and Kingston, {David G.I.}",

note = "Funding Information: This work was supported by a National Cooperative Drug Discovery Group grant awarded to the University of Virginia by the National Cancer Institute (U19 CA 50771), and this support is gratefully acknowledged. The extract of the unidentified sponge species was provided by the NCI under a collaborative agreement. We thank Drs. David Newman and Gordon Cragg for arranging this collaboration, and Dr. Chris Battershill, Australian Institute of Marine Science, for the sponge photographs. We also thank Mr. William Bebout, Virginia Polytechnic Institute and State University, for the mass spectrometry data. Copyright: Copyright 2012 Elsevier B.V., All rights reserved.",

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doi = "10.1016/j.tet.2004.08.017",

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AU - Chaturvedula, V. S.Prakash

AU - Gao, Zhijie

AU - Thomas, Shannon H.

AU - Hecht, Sidney M.

AU - Kingston, David G.I.

N1 - Funding Information: This work was supported by a National Cooperative Drug Discovery Group grant awarded to the University of Virginia by the National Cancer Institute (U19 CA 50771), and this support is gratefully acknowledged. The extract of the unidentified sponge species was provided by the NCI under a collaborative agreement. We thank Drs. David Newman and Gordon Cragg for arranging this collaboration, and Dr. Chris Battershill, Australian Institute of Marine Science, for the sponge photographs. We also thank Mr. William Bebout, Virginia Polytechnic Institute and State University, for the mass spectrometry data. Copyright: Copyright 2012 Elsevier B.V., All rights reserved.

PY - 2004/10/25

Y1 - 2004/10/25

N2 - Using an assay to detect inhibitors of the lyase activity of DNA polymerase β, bioassay-directed fractionation of a CHCl 3 extract of an unidentified sponge of the family Demospongiae resulted in the isolation of the new diterpenoid 1, the new bis-norditerpenoids 2-3, and the two known compounds spongia-13(16),14-dien-19-oic acid (4), and methylspongia-13(16),14-dien-19-oate (5). The structures of the new compounds were established on the basis of extensive 1D and 2D NMR spectroscopic interpretation. All five compounds inhibited the lyase activity of DNA polymerase β. Bioassay-directed fractionation of a CHCl 3 extract of an unidentified sponge of the family Demospongiae resulted in the isolation of the new diterpenoid 1, the new bis-norditerpenoids 2-3, and two known compounds. All the isolated compounds were weak inhibitors of the lyase activity of DNA polymerase β.

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KW - Bioactivity

KW - DNA polymerase β

KW - Diterpenoid

KW - Marine

KW - Sponge

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New norditerpenoids and a diterpenoid from a sponge that inhibit the lyase activity of DNA polymerase β

Abstract

Keywords

ASJC Scopus subject areas

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