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

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29 Citations (Scopus)

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
Issue number	33
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

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10.1002/ejoc.200901016

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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",

pages = "5711--5715",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley",

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

C2 - 23606807

SN - 1434-193X

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

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