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

Gachon University
Korea Research Institute of Chemical Technology
Dong-A Pharm Institute
Sungkyunkwan University

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

16 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",

language = "English",

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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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