nps Natural Product Sciences Natural Product Sciences 1226-3907 2288-9027 The Korean Society of Pharmacognosy 10.20307/nps.2016.22.2.107 nps-22-107 Original Article A New Stereoisomeric Monoterpene Glycoside from Clematis heracleifolia leaves Kim Mi Ae 1 Yang Heejung 1 Kim Myong Jo 2 Chun Wanjoo 3 Kwon Yongsoo 1 ∗ College of Pharmacy, Kangwon National University 200-701, Chuncheon, Korea College of Agriculture and Life Science 200-701, Chuncheon, Korea College 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 122016 17122016 222 107110 17112015 30122015 31122015 Copyright © 2016 The Korean Society of Pharmacognosy 2016 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.

 Clematis heracleifolia Monoterpene glycoside (6 Z)-9-hydroxylinaloyl glucoside REFERENCES Lee W. T. Standard illustrations of Korean plants; Academy Pub. Co: Seoul 1996 110 Bae K. The medicinal plants of Korea Kyo-Hak Pub. Co Seoul 2012 136 Kim M. A. Kim M. J. Chun W. Kwon Y. Kor. J. Pharmacogn. 2015 46 611 Prachayasittikul S. Suphapong S. Worachartcheewan A. Lawung R. Ruchirawat S. Prachayasittikul V. Molecules 2009 14 850867 Zhang H. L. Nagatsu A. Okuyama H. Mizukami H. Sakakibara J. Phytochemistry 1998 48 665668 Lin Z. Fang Y. Huang A. Chen L. Cuo S. Chen J. Pharm. Biol. 2014 52 14291434 Bayoumi S. A. Rowan M. G. Beeching J. R. Blagbrough I. S. Phytochemistry 2010 71 598604 Manns D. Phytochemistry 1995 39 11151118 Uchiyama T. Miyase T. Ueno A. Usmanghani K. Phytochemistry 1989 28 33693372 Figures and Tables

Structures of the compounds isolated from C. heracleifolia.

Important HMBC (H → C) and NOESY (H ↔ H) correlations of compounds 5 and 6.

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

dissolved in CD3 OD

issolved in CDCl