Anti-Inflammatory Activity of a Novel Acetylene Isolated from the Roots of Angelica tenuissima Nakai

Hyun Gyu Choi; Hyukjae Choi; Jeong Hyung Lee; Byung Sun Min; Jeong Ah Kim

doi:10.1002/hlca.201500507

Anti-Inflammatory Activity of a Novel Acetylene Isolated from the Roots of Angelica tenuissima Nakai

Hyun Gyu Choi, Hyukjae Choi, Jeong Hyung Lee, Byung Sun Min, Jeong Ah Kim

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

5 Scopus citations

Abstract

Three polyacetylenes, one novel and two known, were isolated from the root of Angelica tenuissima. Using¹H- and¹³C-NMR, COSY, HMBC, and HMQC, their structures were found to be (3R,8S)-heptadeca-1-en-4,6-diyne-3,8-diol (1), falcarindiol (2), and oplopandiol (3). Absolute configurations of compound 1 were established using Mosher's esterification. In addition, the polyacetylenes (1 – 3) were evaluated for their anti-inflammatory activity. Compounds 1 and 3 showed potent inhibitory activity against lipopolysaccharide-induced nitric oxide (NO) production in RAW267.7 macrophage cells with IC₅₀values of 4.31 and 5.06 μm, respectively. Compound 1 strongly inhibited inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 in a concentration-dependent manner.

Original language	English
Pages (from-to)	447-451
Number of pages	5
Journal	Helvetica Chimica Acta
Volume	99
Issue number	6
DOIs	https://doi.org/10.1002/hlca.201500507
State	Published - Jun 2016

Keywords

Angelica tenuissima
COX-2
iNOS
NO
Polyacetylenes

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title = "Anti-Inflammatory Activity of a Novel Acetylene Isolated from the Roots of Angelica tenuissima Nakai",

abstract = "Three polyacetylenes, one novel and two known, were isolated from the root of Angelica tenuissima. Using1H- and13C-NMR, COSY, HMBC, and HMQC, their structures were found to be (3R,8S)-heptadeca-1-en-4,6-diyne-3,8-diol (1), falcarindiol (2), and oplopandiol (3). Absolute configurations of compound 1 were established using Mosher's esterification. In addition, the polyacetylenes (1 – 3) were evaluated for their anti-inflammatory activity. Compounds 1 and 3 showed potent inhibitory activity against lipopolysaccharide-induced nitric oxide (NO) production in RAW267.7 macrophage cells with IC50values of 4.31 and 5.06 μm, respectively. Compound 1 strongly inhibited inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 in a concentration-dependent manner.",

keywords = "Angelica tenuissima, COX-2, iNOS, NO, Polyacetylenes",

author = "Choi, {Hyun Gyu} and Hyukjae Choi and Lee, {Jeong Hyung} and Min, {Byung Sun} and Kim, {Jeong Ah}",

note = "Publisher Copyright: {\textcopyright} 2016 Verlag Helvetica Chimica Acta AG, Z{\"u}rich",

year = "2016",

month = jun,

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AU - Choi, Hyun Gyu

AU - Choi, Hyukjae

AU - Lee, Jeong Hyung

AU - Min, Byung Sun

AU - Kim, Jeong Ah

PY - 2016/6

Y1 - 2016/6

N2 - Three polyacetylenes, one novel and two known, were isolated from the root of Angelica tenuissima. Using1H- and13C-NMR, COSY, HMBC, and HMQC, their structures were found to be (3R,8S)-heptadeca-1-en-4,6-diyne-3,8-diol (1), falcarindiol (2), and oplopandiol (3). Absolute configurations of compound 1 were established using Mosher's esterification. In addition, the polyacetylenes (1 – 3) were evaluated for their anti-inflammatory activity. Compounds 1 and 3 showed potent inhibitory activity against lipopolysaccharide-induced nitric oxide (NO) production in RAW267.7 macrophage cells with IC50values of 4.31 and 5.06 μm, respectively. Compound 1 strongly inhibited inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 in a concentration-dependent manner.

AB - Three polyacetylenes, one novel and two known, were isolated from the root of Angelica tenuissima. Using1H- and13C-NMR, COSY, HMBC, and HMQC, their structures were found to be (3R,8S)-heptadeca-1-en-4,6-diyne-3,8-diol (1), falcarindiol (2), and oplopandiol (3). Absolute configurations of compound 1 were established using Mosher's esterification. In addition, the polyacetylenes (1 – 3) were evaluated for their anti-inflammatory activity. Compounds 1 and 3 showed potent inhibitory activity against lipopolysaccharide-induced nitric oxide (NO) production in RAW267.7 macrophage cells with IC50values of 4.31 and 5.06 μm, respectively. Compound 1 strongly inhibited inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 in a concentration-dependent manner.

KW - Angelica tenuissima

KW - COX-2

KW - iNOS

KW - NO

KW - Polyacetylenes

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JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 6

ER -

Anti-Inflammatory Activity of a Novel Acetylene Isolated from the Roots of Angelica tenuissima Nakai

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