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

Planta Medica, Table of Contents

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

¹Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Jangan-ku, Suwon, Gyeonggi-do, Republic of Korea

,

Eunjung Moon

²College of Pharmacy, Gachon University, Yeonsu-gu, Incheon, Republic of Korea

,

Sun Yeou Kim

²College of Pharmacy, Gachon University, Yeonsu-gu, Incheon, Republic of Korea

³Gachon Institute of Pharmaceutical Sciences, Gachon University, Yeonsu-gu, Incheon, Republic of Korea

,

Sang Un Choi

⁴Korea Research Institute of Chemical Technology, Teajeon, Republic of Korea

,

Mi Won Son

⁵Dong-A Pharm Institute, Kiheung, Youngin, Republic of Korea

,

Sang Zin Choi

⁵Dong-A Pharm Institute, Kiheung, Youngin, Republic of Korea

,

Kang Ro Lee

¹Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Jangan-ku, Suwon, Gyeonggi-do, Republic of Korea

› Author Affiliations

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.

Key words

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

Full Text

References

References
1 Liang T, Qin Y, Liang N. Study on anti-inflammatory effect of Biota orientalis . J Chin Pharm Univ 2001; 32: 224-226
2 Lu Y, Liu Z, Wang Z, Wei D. Quality evaluation of Platycladus orientalis (L.) Franco through simultaneous determination of four bioactive flavonoids by high-performance liquid chromatography. J Pharm Biomed Anal 2006; 41: 1186-1190
3 Sung SH, Koo KA, Lim HK, Lee HS, Cho JH, Kim HS, Kim YC. Diterpenes of Biota orientalis leaves. Kor J Pharmacogn 1998; 29: 347-352
4 Srivastava P, Kumar P, Singh DK, Singh VK. Biological properties of Thuja orientalis Linn. Adv Life Sci 2012; 2: 17-20
5 Asili J, Asghari G, Sadat Ebrahimi SE, Jaroszewski JW. Influence of extraction methods on the yield and chemical composition of essential oil of Platycladus orientalis (L.) Franco. Jundishapur J Nat Pharm Prod 2007; 2: 25-33
6 Guleria S, Kumar A, Tiku AK. Chemical composition and fungitoxic activity of essential oil of Thuja orientalis L. grown in the north-western Himalaya. Z Naturforsch C 2008; 63: 211-214
7 Nickavar B, Amin G, Parhami S. Volatile constituents of the fruit and leaf oils of Thuja orientalis L. grown in Iran. Z Naturforsch C 2003; 58: 171-172
8 Chen Y, Li S, Yang L, Jiang Z. Comparative study on chemical constituents of essential oils from several parts of Platycladus orientalis (L.) Franco. Linchan Huaxue Yu Gongye 1984; 4: 1-11
9 Li Z, Liu S. Chemical constituents of essential oil from the fruit of Biota orientalis . Zhongguo Yaoxue Zazhi 1997; 32: 138-139
10 Kim CS, Choi SU, Lee KR. Three new diterpenoids from the leaves of Thuja orientalis . Planta Med 2012; 78: 485-487
11 Cool LG, Jiang K. Thujopsene- and cis-muurolane-related sesquiterpenoids from Cupressus bakeri . Phytochemistry 1995; 40: 177-181
12 Sakamaki H, Kitanaka S, Chai W, Hayashida Y, Takagi Y, Horiuchi CA. Biotransformation of thujopsene by Caragana chamlagu . J Nat Prod 2001; 64: 630-631
13 Nagahama S, Fuchinoue T, Tazaki M. Terpenoids. XI. Mayurone oxide. Bull Chem Soc Jpn 1988; 61: 4147-4148
14 Fang JM, Chen YC, Wang BW, Cheng YS. Terpenes from heartwood of Juniperus chinensis . Phytochemistry 1996; 41: 1361-1365
15 Abreu PM, Noronha RG. Volatile constituents of the rhizomes of Aframomum alboviolaceum (Ridley) K. Schum. from Guinea-Bissau. Flavour Fragr J 1997; 12: 79-83
16 Nagahama S, Tazaki M, Kobayashi H, Sumimoto M. Sesquiterpene alcohols from Cryptomeria japonica and C. fortunei leaf oil. Phytochemistry 1993; 33: 879-882
17 Zhang CX, Fang LJ, Bi FQ, Li YL. An enantioselective formal synthesis of (−)-thujopsene. Chin Chem Lett 2008; 19: 256-258
18 Skehan P, Storeng R, Scudiero D, Monks A, Mcmahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990; 82: 1107-1112
19 Jung HW, Kang SY, Park KH, Oh TW, Jung JK, Kim SH, Choi DJ, Park YK. Effect of the semen extract of Thuja orientalis on inflammatory responses in transient focal cerebral ischemia rat model and LPS-stimulated BV-2 microglia. Am J Chin Med 2013; 41: 99-117
20 Kim JY, Kim HJ, Kim SM, Park KR, Jang HJ, Lee EH, Jung SH, Ahn KS. Methylene chloride fraction of the leaves of Thuja orientalis inhibits in vitro inflammatory biomarkers by blocking NF-κB and p 38 MAPK signaling and protects mice from lethal endotoxemia. J Ethnopharmacol 2011; 133: 687-695

Supplementary Material

Supporting Information