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Kim, Yang, Kim, Chun, and Kwon: A New Stereoisomeric Monoterpene Glycoside from Clematis heracleifolia leaves
Original Article

Natural Product Sciences 2016;22(2):107-110.

Published online: 17 December 2016

DOI: https://doi.org/10.20307/nps.2016.22.2.107

A New Stereoisomeric Monoterpene Glycoside from Clematis heracleifolia leaves

Mi Ae Kim1, Heejung Yang1, Myong Jo Kim2, Wanjoo Chun3, Yongsoo Kwon1, ∗

1College of Pharmacy, Kangwon National University 200-701, Chuncheon, Korea

2College of Agriculture and Life Science 200-701, Chuncheon, Korea

3College of Medicine, Kangwon National University 200-701, Chuncheon, Korea

∗Author for correspondence Yongsoo Kwon, College of Pharmacy, Kangwon National University 200-701, Chuncheon, Korea Tel: +82-33-250-6921; E-mail: yskwon@kangwon.ac.kr

Received 17 November 2015       Revised 30 December 2015       Accepted 31 December 2015

Copyright © 2016 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 stereoisomeric monoterpene glycoside and five already-known compounds were isolated from the n-BuOH soluble fraction of Clematis heracleifolia leaves. On the basis of spectral data, the structures of the isolated compounds were identified as protocatechuic acid (1), ferulic acid (2), caffeic acid (3), aesculin (4), (6Z)-9-hydroxylinaloyl glucoside (5), and 9-hydroxylinaloyl glucoside (6) and these were isolated for the first time from this plant. Among these compounds, (6Z)-9-hydroxylinaloyl glucoside (5) is a newly isolated from plant source.

Keywords: Clematis heracleifolia, Monoterpene glycoside, (6 Z)-9-hydroxylinaloyl glucoside

REFERENCES

(1). Lee W. T.Standard illustrations of Korean plants; Academy Pub. Co: Seoul. 1996; 110.
(2). Bae K.The medicinal plants of Korea. Kyo-Hak Pub. Co;Seoul: 2012. p. 136.
(3). Kim M. A., Kim M. J., Chun W., Kwon Y.Kor. J. Pharmacogn. 2015; 46:6–11.
(4). Prachayasittikul S., Suphapong S., Worachartcheewan A., Lawung R., Ruchirawat S., Prachayasittikul V.Molecules. 2009; 14:850–867.
(5). Zhang H. L., Nagatsu A., Okuyama H., Mizukami H., Sakakibara J.Phytochemistry. 1998; 48:665–668.
(6). Lin Z., Fang Y., Huang A., Chen L., Cuo S., Chen J.Pharm. Biol. 2014; 52:1429–1434.
(7). Bayoumi S. A., Rowan M. G., Beeching J. R., Blagbrough I. S.Phytochemistry. 2010; 71:598–604.
(8). Manns D.Phytochemistry. 1995; 39:1115–1118.
(9). Uchiyama T., Miyase T., Ueno A., Usmanghani K.Phytochemistry. 1989; 28:3369–3372.

Fig. 1.
Structures of the compounds isolated from C. heracleifolia.
nps-22-107f1.tif
Fig. 2.
Important HMBC (H → C) and NOESY (H ↔ H) correlations of compounds 5 and 6.
nps-22-107f2.tif
Table 1.
13C NMR data of compounds 5, 5a and 6
  51) 5a2) 61)
1 113.56 111.87 113.58
2 143.18 144.93 143.09
3 79.83 73.47 79.91
4 40.11 42.05 39.84
5 21.70 22.38 21.84
6 127.62 128.49 125.58
7 134.19 134.56 134.42
8 20.08 21.43 12.33
9 60.00 61.61 67.58
10 22.40 28.14 22.14
Sugar moiety
Glc 1 97.91   97.87
2 73.70   73.68
3 76.86   76.86
4 70.32   70.33
5 76.23   76.21
6 61.35   61.43

1) dissolved in CD3 OD

2) issolved in CDCl

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