Iso-seco-tanapartholides: isolation, synthesis and biological evaluation

Edward F. Makiyi; Raquel F. M. Frade; Tomas Lebl; Ellis G. Jaffray; Susan E. Cobb; Alan L. Harvey; Alexandra M. Z. Slawin; Ronald T. Hay; Nicholas J. Westwood

doi:10.1002/ejoc.200901016

Iso-seco-tanapartholides: isolation, synthesis and biological evaluation

Edward F. Makiyi
, Raquel F. M. Frade
, Tomas Lebl
, Ellis G. Jaffray
, Susan E. Cobb
, Alan L. Harvey
, Alexandra M. Z. Slawin
, Ronald T. Hay
, Nicholas J. Westwood

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

Abstract

The isolation, identification and total synthesis of two plant-derived inhibitors of the NF-kappa B signaling pathway from the iso-seco-tanapartholide family of natural products is described. A key step in the efficient reaction sequence is a late-stage oxidative cleavage reaction that was carried out in the absence of protecting groups to give the natural products directly. A detailed comparison of the synthetic material with samples of the natural products proved informative. Biological studies on synthetic material confirmed that these compounds act late in the NF-kappa B signaling pathway. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Original language	English
Pages (from-to)	5711-5715
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2009
Issue number	33
Early online date	7 Oct 2009
DOIs	https://doi.org/10.1002/ejoc.200901016
Publication status	Published - Nov 2009

Keywords

Natural products
Total synthesis
Terpenoids
Cleavage reaction
Inflammation
NF-KAPPA-B
Sesquiterpene lactones
Natural-products
Drug Discovery
Constituents
Inhibition

Access to Document

10.1002/ejoc.200901016

Westwood backup
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim This is an open access article. Re-use of this article is permitted in accordance with the Terms and Conditions set out at http://wileyonlinelibrary.com/onlineopen#OnlineOpen_Terms
Final published version, 229 KB

Handle.net

Persistent link

ROYAL SOCIETY RESEARCH FELLOWSHIP: Chemical Genetic Approach
Westwood, N. (PI)
The Royal Society
1/10/01 → 30/09/09
Project: Fellowship

Cite this

@article{b3be03a0b12d46d484b5a11bb3af7303,

title = "Iso-seco-tanapartholides: isolation, synthesis and biological evaluation",

abstract = "The isolation, identification and total synthesis of two plant-derived inhibitors of the NF-kappa B signaling pathway from the iso-seco-tanapartholide family of natural products is described. A key step in the efficient reaction sequence is a late-stage oxidative cleavage reaction that was carried out in the absence of protecting groups to give the natural products directly. A detailed comparison of the synthetic material with samples of the natural products proved informative. Biological studies on synthetic material confirmed that these compounds act late in the NF-kappa B signaling pathway. ((C) Wiley-VCH Verlag GmbH \& Co. KGaA, 69451 Weinheim, Germany, 2009)",

keywords = "Natural products, Total synthesis, Terpenoids, Cleavage reaction, Inflammation, NF-KAPPA-B, Sesquiterpene lactones, Natural-products, Drug Discovery, Constituents, Inhibition",

author = "Makiyi, \{Edward F.\} and Frade, \{Raquel F. M.\} and Tomas Lebl and Jaffray, \{Ellis G.\} and Cobb, \{Susan E.\} and Harvey, \{Alan L.\} and Slawin, \{Alexandra M. Z.\} and Hay, \{Ronald T.\} and Westwood, \{Nicholas J.\}",

year = "2009",

month = nov,

doi = "10.1002/ejoc.200901016",

language = "English",

volume = "2009",

pages = "5711--5715",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

number = "33",

}

TY - JOUR

T1 - Iso-seco-tanapartholides

T2 - isolation, synthesis and biological evaluation

AU - Makiyi, Edward F.

AU - Frade, Raquel F. M.

AU - Lebl, Tomas

AU - Jaffray, Ellis G.

AU - Cobb, Susan E.

AU - Harvey, Alan L.

AU - Slawin, Alexandra M. Z.

AU - Hay, Ronald T.

AU - Westwood, Nicholas J.

PY - 2009/11

Y1 - 2009/11

N2 - The isolation, identification and total synthesis of two plant-derived inhibitors of the NF-kappa B signaling pathway from the iso-seco-tanapartholide family of natural products is described. A key step in the efficient reaction sequence is a late-stage oxidative cleavage reaction that was carried out in the absence of protecting groups to give the natural products directly. A detailed comparison of the synthetic material with samples of the natural products proved informative. Biological studies on synthetic material confirmed that these compounds act late in the NF-kappa B signaling pathway. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

AB - The isolation, identification and total synthesis of two plant-derived inhibitors of the NF-kappa B signaling pathway from the iso-seco-tanapartholide family of natural products is described. A key step in the efficient reaction sequence is a late-stage oxidative cleavage reaction that was carried out in the absence of protecting groups to give the natural products directly. A detailed comparison of the synthetic material with samples of the natural products proved informative. Biological studies on synthetic material confirmed that these compounds act late in the NF-kappa B signaling pathway. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

KW - Natural products

KW - Total synthesis

KW - Terpenoids

KW - Cleavage reaction

KW - Inflammation

KW - NF-KAPPA-B

KW - Sesquiterpene lactones

KW - Natural-products

KW - Drug Discovery

KW - Constituents

KW - Inhibition

U2 - 10.1002/ejoc.200901016

DO - 10.1002/ejoc.200901016

M3 - Article

SN - 1434-193X

VL - 2009

SP - 5711

EP - 5715

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 33

ER -

Iso-seco-tanapartholides: isolation, synthesis and biological evaluation

Abstract

Keywords

Access to Document

Handle.net

Fingerprint

Projects

ROYAL SOCIETY RESEARCH FELLOWSHIP: Chemical Genetic Approach

Cite this