Bioactive sesquiterpenes from the essential oil of Thuja orientalis

Ki Hyun Kim; Eunjung Moon; Sun Yeou Kim; Sang Un Choi; Mi Won Son; Sang Zin Choi; Kang Ro Lee

doi:10.1055/s-0033-1350952

Bioactive sesquiterpenes from the essential oil of Thuja orientalis

Ki Hyun Kim, Eunjung Moon, Sun Yeou Kim, Sang Un Choi, Mi Won Son, Sang Zin Choi, Kang Ro Lee

Department of Pharmacy

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

14 Scopus citations

Abstract

A phytochemical investigation on the essential oil of Thuja orientalis resulted in the isolation and identification of three new sesquiterpenes, 3α-methoxy-4α-epoxythujopsane (1), Δ^3,15-4β- epoxythujopsene (2), and Δ^3,4-thujopsen-2,15-diol (3), together with eight known sesquiterpenoids (4-11). The structures of these new compounds were elucidated based on spectroscopic data analyses including extensive 2D-NMR data and HR-ESIMS. The full assignments of ¹H and ¹³C NMR chemical shifts for thujopsadiene (4) were obtained by 2D-NMR for the first time. All compounds (1-11) showed antiproliferative activities against the SK-OV-3 and SK-MEL-2 cell lines with IC₅₀ values of 5.85-28.64 μM. In addition, compounds 1, 3, 4, 7, 8, and 9 significantly inhibited nitric oxide production in lipopolysaccharide-activated BV-2 cells with IC₅₀ values of 3.93-17.85 μM without cell toxicity.

Original language	English
Pages (from-to)	1680-1684
Number of pages	5
Journal	Planta Medica
Volume	79
Issue number	17
DOIs	https://doi.org/10.1055/s-0033-1350952
State	Published - 17 Oct 2013

Keywords

anti-inflammation
Cupressaceae
cytotoxicity
sesquiterpene
Thuja orientalis

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title = "Bioactive sesquiterpenes from the essential oil of Thuja orientalis",

abstract = "A phytochemical investigation on the essential oil of Thuja orientalis resulted in the isolation and identification of three new sesquiterpenes, 3α-methoxy-4α-epoxythujopsane (1), Δ3,15-4β- epoxythujopsene (2), and Δ3,4-thujopsen-2,15-diol (3), together with eight known sesquiterpenoids (4-11). The structures of these new compounds were elucidated based on spectroscopic data analyses including extensive 2D-NMR data and HR-ESIMS. The full assignments of 1H and 13C NMR chemical shifts for thujopsadiene (4) were obtained by 2D-NMR for the first time. All compounds (1-11) showed antiproliferative activities against the SK-OV-3 and SK-MEL-2 cell lines with IC50 values of 5.85-28.64 μM. In addition, compounds 1, 3, 4, 7, 8, and 9 significantly inhibited nitric oxide production in lipopolysaccharide-activated BV-2 cells with IC50 values of 3.93-17.85 μM without cell toxicity.",

keywords = "anti-inflammation, Cupressaceae, cytotoxicity, sesquiterpene, Thuja orientalis",

author = "Kim, \{Ki Hyun\} and Eunjung Moon and Kim, \{Sun Yeou\} and Choi, \{Sang Un\} and Son, \{Mi Won\} and Choi, \{Sang Zin\} and Lee, \{Kang Ro\}",

year = "2013",

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doi = "10.1055/s-0033-1350952",

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AU - Kim, Ki Hyun

AU - Moon, Eunjung

AU - Kim, Sun Yeou

AU - Choi, Sang Un

AU - Son, Mi Won

AU - Choi, Sang Zin

AU - Lee, Kang Ro

PY - 2013/10/17

Y1 - 2013/10/17

N2 - A phytochemical investigation on the essential oil of Thuja orientalis resulted in the isolation and identification of three new sesquiterpenes, 3α-methoxy-4α-epoxythujopsane (1), Δ3,15-4β- epoxythujopsene (2), and Δ3,4-thujopsen-2,15-diol (3), together with eight known sesquiterpenoids (4-11). The structures of these new compounds were elucidated based on spectroscopic data analyses including extensive 2D-NMR data and HR-ESIMS. The full assignments of 1H and 13C NMR chemical shifts for thujopsadiene (4) were obtained by 2D-NMR for the first time. All compounds (1-11) showed antiproliferative activities against the SK-OV-3 and SK-MEL-2 cell lines with IC50 values of 5.85-28.64 μM. In addition, compounds 1, 3, 4, 7, 8, and 9 significantly inhibited nitric oxide production in lipopolysaccharide-activated BV-2 cells with IC50 values of 3.93-17.85 μM without cell toxicity.

AB - A phytochemical investigation on the essential oil of Thuja orientalis resulted in the isolation and identification of three new sesquiterpenes, 3α-methoxy-4α-epoxythujopsane (1), Δ3,15-4β- epoxythujopsene (2), and Δ3,4-thujopsen-2,15-diol (3), together with eight known sesquiterpenoids (4-11). The structures of these new compounds were elucidated based on spectroscopic data analyses including extensive 2D-NMR data and HR-ESIMS. The full assignments of 1H and 13C NMR chemical shifts for thujopsadiene (4) were obtained by 2D-NMR for the first time. All compounds (1-11) showed antiproliferative activities against the SK-OV-3 and SK-MEL-2 cell lines with IC50 values of 5.85-28.64 μM. In addition, compounds 1, 3, 4, 7, 8, and 9 significantly inhibited nitric oxide production in lipopolysaccharide-activated BV-2 cells with IC50 values of 3.93-17.85 μM without cell toxicity.

KW - anti-inflammation

KW - Cupressaceae

KW - cytotoxicity

KW - sesquiterpene

KW - Thuja orientalis

UR - https://www.scopus.com/pages/publications/84889601536

U2 - 10.1055/s-0033-1350952

DO - 10.1055/s-0033-1350952

M3 - Article

C2 - 24135886

AN - SCOPUS:84889601536

SN - 0032-0943

VL - 79

SP - 1680

EP - 1684

JO - Planta Medica

JF - Planta Medica

IS - 17

ER -

Bioactive sesquiterpenes from the essential oil of Thuja orientalis

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Keywords

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