Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs

Su Lin Lee; Wei Jan Huang; Wan Wan Lin; Shoei Sheng Lee; Chung Hsiung Chen

doi:10.1016/j.bmc.2005.06.058

Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs

Su Lin Lee, Wei Jan Huang, Wan Wan Lin, Shoei Sheng Lee, Chung Hsiung Chen

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

78 Citations (Scopus)

Abstract

Seven diarylheptylamine (12a-g) and four diarylheptanoid analogs (3-5, 9), structurally related to the natural anti-inflammatory agent oregonin (1), have been prepared from curcumin (2) for evaluation of their activity against the expression of iNOS and COX-2. Diarylheptylamine 12b and diarylheptanoid analogs can inhibit iNOS and COX-2 responses of LPS, although less potently than 1. These compounds, however, possess stronger potency than 1 against COX-2-derived PGE₂ formation, of which hexahydrocurcumin (4) is the most potent one with an IC₅₀ value of 0.7 μM.

Original language	English
Pages (from-to)	6175-6181
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	13
Issue number	22
DOIs	https://doi.org/10.1016/j.bmc.2005.06.058
Publication status	Published - Nov 15 2005

Keywords

Anti-inflammatory activity
Curcumin
Diarylheptanoid
Diarylheptylamine
Preparation

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2005.06.058

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title = "Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs",

abstract = "Seven diarylheptylamine (12a-g) and four diarylheptanoid analogs (3-5, 9), structurally related to the natural anti-inflammatory agent oregonin (1), have been prepared from curcumin (2) for evaluation of their activity against the expression of iNOS and COX-2. Diarylheptylamine 12b and diarylheptanoid analogs can inhibit iNOS and COX-2 responses of LPS, although less potently than 1. These compounds, however, possess stronger potency than 1 against COX-2-derived PGE2 formation, of which hexahydrocurcumin (4) is the most potent one with an IC50 value of 0.7 μM.",

keywords = "Anti-inflammatory activity, Curcumin, Diarylheptanoid, Diarylheptylamine, Preparation",

author = "Lee, {Su Lin} and Huang, {Wei Jan} and Lin, {Wan Wan} and Lee, {Shoei Sheng} and Chen, {Chung Hsiung}",

note = "Funding Information: This work was supported by the National Science Council, Taiwan, ROC, under Grant NSC 92-2320-B-002-082. ",

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AU - Lee, Su Lin

AU - Huang, Wei Jan

AU - Lin, Wan Wan

AU - Lee, Shoei Sheng

AU - Chen, Chung Hsiung

N1 - Funding Information: This work was supported by the National Science Council, Taiwan, ROC, under Grant NSC 92-2320-B-002-082.

PY - 2005/11/15

Y1 - 2005/11/15

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AB - Seven diarylheptylamine (12a-g) and four diarylheptanoid analogs (3-5, 9), structurally related to the natural anti-inflammatory agent oregonin (1), have been prepared from curcumin (2) for evaluation of their activity against the expression of iNOS and COX-2. Diarylheptylamine 12b and diarylheptanoid analogs can inhibit iNOS and COX-2 responses of LPS, although less potently than 1. These compounds, however, possess stronger potency than 1 against COX-2-derived PGE2 formation, of which hexahydrocurcumin (4) is the most potent one with an IC50 value of 0.7 μM.

KW - Anti-inflammatory activity

KW - Curcumin

KW - Diarylheptanoid

KW - Diarylheptylamine

KW - Preparation

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Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs

Abstract

Keywords

ASJC Scopus subject areas

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