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Planta Med 2013; 79(17): 1680-1684
DOI: 10.1055/s-0033-1350952
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

Bioactive Sesquiterpenes from the Essential Oil of Thuja orientalis

Ki Hyun Kim
1   Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Jangan-ku, Suwon, Gyeonggi-do, Republic of Korea
,
Eunjung Moon
2   College of Pharmacy, Gachon University, Yeonsu-gu, Incheon, Republic of Korea
,
Sun Yeou Kim
2   College of Pharmacy, Gachon University, Yeonsu-gu, Incheon, Republic of Korea
3   Gachon Institute of Pharmaceutical Sciences, Gachon University, Yeonsu-gu, Incheon, Republic of Korea
,
Sang Un Choi
4   Korea Research Institute of Chemical Technology, Teajeon, Republic of Korea
,
Mi Won Son
5   Dong-A Pharm Institute, Kiheung, Youngin, Republic of Korea
,
Sang Zin Choi
5   Dong-A Pharm Institute, Kiheung, Youngin, Republic of Korea
,
Kang Ro Lee
1   Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Jangan-ku, Suwon, Gyeonggi-do, Republic of Korea
› Author Affiliations
Further Information

Publication History

received 01 July 2013
revised 03 September 2013

accepted 17 September 2013

Publication Date:
17 October 2013 (online)

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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.

Key words

Thuja orientalis - Cupressaceae - sesquiterpene - cytotoxicity - anti-inflammation

Supporting Information

 

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