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Li, Liu, Kim, Wang, Li, Kim, Yook, and Liu: Chemical Constituents from Leaves of Pileostegia viburnoides Hook.f.et Thoms
Original Article

Natural Product Sciences 2016;22(3):154-161.

Published online: 17 January 2016

DOI: https://doi.org/10.20307/nps.2016.22.3.154

Chemical Constituents from Leaves of Pileostegia viburnoides Hook.f.et Thoms

Xiao Jun Li1, 2, Zu Zhen Liu3, Kwan-Woo Kim2, Xiang Wang1, Zhi Li1, Youn-Chul Kim2, Chang Soo Yook4, Xiang Qian Liu1, 5, ∗

1School of Pharmacy, Hunan University of Chinese Medicine, Changsha, Hunan 410208, China

2College of Pharmacy, Wonkwang University, Iksan 570-749, Korea

3Hunan Society of Chinese Medicine, Changsha, Hunan 410008, China

4School of Pharmacy, KyungHee University, Seoul 130-701, Korea

5Broad-Ocean Bio-Science and Technique Co., Ltd of Changsha, Hunan Changsha 410205, China

∗Author for correspondence Xiang Qian Liu, School of Pharmacy, Hunan University of Chinese Medicine, Hunan Changsha 410208, China. Tel: +86-731-88458240; E-mail: lxq0001cn@163.com

Received 26 October 2015       Revised 12 February 2016       Accepted 22 February 2016

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

Phytochemical investigation on the leaves of Pileostegia viburnoides Hook.f.et Thoms led to the isolation of twenty-five compounds, and their structures were identified as n-dotriacontane (1), taraxeryl acetate (2), friedelin (3), epifriedelinol (4), canophyllal (5), stigmast-4-en-3-one (6), stigmasterol (7), (24R)-5A-stigmastane-3,6-dione (8), ursolic acid (9), pomolic acid (10), umbelliferone (11), 4-epifriedelin (12), n-octatriacontanol (13),β-amyrin (14), α-amyrin (15), taraxerol (16), nonadecanol (17), friedelane (18), arachic acid (19), protocatechuic acid (20), n-pentatriacontanol (21), hexadecanoic acid (22), vincosamide (23), daucosterol (24), and skimming (25), respectively. To our best knowledge, compounds 1, 2, 12, 13, 17–19 and 21-23 were new within Saxifragaceae family. Compounds 15, 16, and 20 were produced from this genus for the first time. Compounds 4,14 and 25 were first obtained from species P. viburnoides and compounds 3, 5–11, and 24 were achieved from the leaves of P. viburnoides for the first time. Furthermore, the anti-neuroinflammatory activity of these isolates was evaluated.

Keywords: Pileostegia viburnoides Hook.f.et Thoms, Triterpenes, 4-epifriedelin, Coumarins, Vincosamide, Chemical constituents, Anti-neuroinflammatory

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Fig. 1.
Chemical structures of the isolated compounds 1–25.
nps-22-154f1.tif
Fig. 2.
Effects of selected compounds 2-5, 11, 12, 16, 18, 23, and 25 on productions of NO in LPS-stimulated BV2 microglias. Cells were pretreated for 30 min with the indicated concentrations of selected compounds, then stimulated for 24 h with LPS (1 µg/mL). The concentrations of nitrite were determined as described in the Experimental Section. Data represent the mean values of three experiments ± SD.
nps-22-154f2.tif
Table 1.
13 C-NMR data of triterpenoids 2-5, 9, 10, 12, 14–16, 18
Position 2 3 4 5 9 10 12 14 15 16 18
1 37.9 22.4 16.0 22.4 40.0 39.4 21.9 38.7 38.7 37.9 22.9
2 23.7 41.7 32.5 41.6 28.0 28.1 37.3 27.4 27.2 27.1 41.7
3 81.2 213.5 72.9 213.3 79.8 78.6 216.7 79.0 79.0 79.2 29.9
4 38.1 58.4 49.3 58.3 40.0 39.5 58.9 38.7 38.7 38.8 58.4
5 55.8 42.3 37.8 42.1 56.9 56.2 40.0 55.1 55.1 55.7 42.4
6 18.9 41.4 41.4 41.2 19.6 19.3 37.5 18.3 18.3 18.8 41.5
7 33.3 18.4 17.5 18.2 34.5 33.9 17.9 32.6 32.9 41.5 18.2
8 39.2 53.2 53.4 53.0 40.7 40.7 53.6 38.5 39.9 39.0 53.1
9 49.4 37.6 37.6 37.2 47.4 48.3 37.2 47.6 47.6 49.5 37.7
10 37.7 59.6 61.5 59.4 38.2 37.8 49.6 37.1 36.9 38.0 59.9
11 17.7 35.8 35.8 35.6 24.2 24.3 35.9 23.7 23.3 17.5 35.8
12 36.9 30.6 30.6 30.7 127.0 128.8 30.7 121.7 124.4 33.7 30.7
13 38.1 39.8 39.8 37.8 139.8 139.6 39.9 145.2 139.5 37.6 39.9
14 158.1 38.4 38.4 38.7 42.9 42.2 38.5 41.7 42.0 158.3 38.5
15 117.1 32.5 32.5 28.2 29.3 29.3 32.6 26.1 28.7 117.1 33.0
16 33.9 36.1 36.1 33.5 25.4 26.4 36.2 27.2 26.6 37.7 36.2
17 36.0 30.1 30.1 47.9 47.8 48.1 30.1 32.9 33.7 35.8 30.2
18 48.9 42.9 42.9 36.6 54.5 54.5 42.9 47.2 59.0 48.7 43.0
19 41.4 35.5 35.5 35.1 40.1 73.1 35.5 46.8 39.6 36.7 35.6
20 29.0 28.3 28.3 28.5 40.5 42.6 28.3 31.2 39.6 28.8 28.4
21 35.3 32.9 32.9 30.6 31.8 27.0 32.9 34.7 31.1 33.1 32.6
22 37.6 39.4 39.4 32.4 38.3 38.5 39.4 37.1 41.5 35.1 39.5
23 28.2 6.9 11.8 6.9 29.0 28.7 13.6 28.1 28.1 28.2 7.7
24 16.7 14.8 16.6 14.8 16.0 15.8 23.3 15.6 15.6 15.6 14.3
25 15.6 18.1 18.4 17.3 16.2 16.3 18.2 15.5 15.5 15.6 18.1
26 26.1 20.4 20.3 18.9 17.8 17.4 20.5 16.8 16.8 26.1 20.3
27 21.4 18.8 18.8 20.2 24.1 24.6 18.9 26.1 23.3 21.5 18.9
28 29.9 32.2 32.3 209.3 181.8 179.3 32.2 28.4 28.1 30.0 32.3
29 33.3 35.2 35.2 34.6 17.9 27.2 35.2 33.3 27.4 33.5 35.3
30 30.0 31.9 31.9 29.5 21.7 16.6 31.9 23.5 21.4 30.1 32.0
31 171.1                    
32 21.4                    
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