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Jung, Min, Jung, and Choi: Sesquiterpenoids from the heartwood of Juniperu s chinensis
Original Article

Natural Product Sciences 2017;23(3):208-212.

Published online: 20 January 2017

DOI: https://doi.org/10.20307/nps.2017.23.3.208

Sesquiterpenoids from the heartwood of Juniperu s chinensis

Hee Jin Jung1, Byung-Sun Min2, Hyun Ah Jung3, ∗, Jae Sue Choi1, ∗

1Department of Food and Life Science, Pukyong National University, Busan 608–737, Republic of Korea

2College of Pharmacy, Catholic University of Daegu, Gyeongbuk 712–702, Republic of Korea

3Department of Food Science and Human Nutrition, Chonbuk National University, Jeonju 561–756, Republic of Korea

∗Author for correspondence Jae Sue Choi, Department of Food and Life Science, Pukyong National University, Busan 608-737, Republic of Korea. Tel: +82-51-629-5845; E-mail: choijs@pknu.ac.kr

Received 5 April 2017       Revised 9 June 2017       Accepted 10 June 2017

Copyright © 2017 The Korean Society of Pharmacognosy

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

A new sesquiterpenoid, 11-hydroxy-valenc-1(10),3(4)-dien-2-one (3), two chemically synthesized but first isolate from nature, 3-oxocedran-8β-ol (1) and valenc-1(10),3(4),11(12)-trien-2-one (2) along with four known compounds, sugiol (4), (+)-nootkatone (5), 11-hydroxy-valenc-1(10)-en-2-one (6), and clovandiol (7), were isolated from the heartwood of Juniperus chinensis. All chemical structures were elucidated using extensive spectroscopic analysis including 1D and 2D NMR spectroscopy. Valenc-1(10),3(4),11(12)-trien-2-one (2) exhibited significant inhibitory activity against butyrylcholinesterase with an IC50 value of 68.45 µM.

Keywords: Juniperus chinensis, 3-Oxocedran-8;2-ol, Valenc-1(10), 3(4), 11(12)-trien-2-one, 11-Hydroxy-valenc-1(10), 3(4)-dien-2-one, Acetylcholinesterase, Butyrylcholinesterase

References

(1). Corner E. J. H.Wayside Trees of Malaya; Malayan Nature Society: Malaysia,. 1988. 396–446.
(2). But P. P. H.., Kimura T.., Gue J. X.., Sung C. K.International Collation of Traditional and Folk Medicine; World Scientific Publishing Co., Ltd.: Singapore,. 1997. 16–17.
(3). Jung H. J.., Jung H. A.., Min B. S.., Choi J. S.Chem. Pharm. Bull. 2015. 63:955–960.
(4). Ellman G. L.., Courtney K. D.., Andres V. Jr.., Feather-stone R. M.Biochem. Pharmacol. 1961. 7:88–95.
(5). Hanson J. R.., Nasir H.Phytochemistry. 1993. 33:835–837.
(6). Gand E.., Hanson J. R.., Nasir H.Phytochemistry. 1995. 39:1081–1084.
(7). Collins D. O.., Reese P. B.Phytochemistry. 2001. 56:417–421.
(8). Caine D.., Chu C. Y.Tetrahedron Lett. 1974. 15:703–706.
(9). Caine D.., Chu C. Y.., Graham S. L. J.Org. Chem. 1980. 45:3790–3797.
(10). Pesaro M.., Bozzato G.., Schudel P.Chem. Commun (London). 1968. 19:1152–1154.
(11). Kuo Y. H.., Wu T. R.., Cheng M. C.., Wang Y.Chem. Pharm. Bull. 1990. 38:3195–3201.
(12). Chang C. I.., Chen W. C.., Shao Y. Y.., Yeh C. R.., Yang N. S.., Chiang W.., Kuo Y. H.Nat. Prod. Res. 2008. 22:1158–1162.
(13). Savona G.., Piozzi F.., De La Torre M. C.., Servettaz, O. Rodríguez B.Phytochemistry. 1987. 26:571–572.
(14). Xu J.., Su J.., Li Y.., Tan N.Chem. Nat. Compd. 2013. 49:457–461.
(15). Zhang C.., Zhou A.., Zhang M.China Journal of Chinese Materia Medica. 2009. 34:994–998.
(16). Furusawa M.., Hashimoto T.., Noma Y.., Asakawa Y.Chem. Pharm. Bull. 2005. 53:1513–1514.
(17). Naf F.., Decorzant R.., Thommen W.Helv. Chim. Acta. 1982. 65:2212–2223.
(18). Wittayalai S.., Mahidol C.., Prachyawarakorn V.., Prawat H.., Ruchirawat S.Phytochemistry. 2014. 99:121–126.

Fig. 1.
Chemical structures of isolated compounds 1 – 7.
nps-23-208f1.tif
Fig. 2.
Key HMBC correlations of compounds 1 and 2.
nps-23-208f2.tif
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