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Nam, Teruhisa, Hirofumi, Hiroshi, Khoi, Dung, Ha, and Hiroshi: Chemical Composition of Clausena lansium (Lour.) Skeels Leaves and Antifungal Activity
Original Article

Natural Product Sciences 2016;22(1):35-40.

Published online: 17 December 2016

DOI: https://doi.org/10.20307/nps.2016.22.1.35

Chemical Composition of Clausena lansium (Lour.) Skeels Leaves and Antifungal Activity

Vu Duc Nam1, Fujimatsu Teruhisa2, Takigawa Hirofumi2, Kusuoku Hiroshi2, Nguyen Minh Khoi1, ∗, Le Viet Dung1, Do Thi Ha1, Hashimoto Hiroshi3

1National Institute of Medicinal Materials, Hanoi 100000, Vietnam

2R&D Biological Science Research, KAO Corporation, Tochigi 321-3497, Japan

3KAO Consumer Products (Southeast Asia) Co., Ltd. Bangkok 10330, Thailand

∗Author for correspondence Minh Khoi, National Institute of Medicinal Materials, Hanoi 100000, Vietnam Tel: +84-0903277782; E-mail: khoi_nguyenminh@yahoo.co.uk

Received 2 July 2015       Revised 5 August 2015       Accepted 7 August 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

The first study on chemical constituents and biological activities of Clausena lansium (Lour.) Skeels (Rutaceae) growing in Vietnam has been done. Phytochemical investigation of n-hexane extract led to the isolation of five compounds: dihydroindicolactone (1), 8-geranyloxy psoralen (2), imperatorin (3), heraclenol (4) and indicolactone (5), in which this is the first report on the presence of dihydroindicolactone (1). Their structures were elucidated based on LC/MS/NMR hyphenated techniques as well as comparison with those of literature data. The n-hexane extract and its subfractions, ethanol 95% extract and several isolated compounds were evaluated for antifungal activity.

Keywords: Antifungal, Clausena lansium, Dihydroindicolactone, Furanocoumarin

REFERENCES

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Fig. 1.
Structures of compounds 1–5.
nps-22-35f1.tif
Fig. 2.
COSY and HMBC correlation of dihydroindicolactone (1).
nps-22-35f2.tif
Fig. 3.
The relative stereochemistry of dihydroindicolactone (1).
nps-22-35f3.tif
Fig. 4.
The geometry of double bond at C-2″ and C-3″ of dihydroindicolactone (1).
nps-22-35f4.tif
Fig. 5.
Antifungal activity of pure compounds and initial extracts.
nps-22-35f5.tif
Table 1.
1 H (600 MHz) and13 C (150 MHz) NMR spectral data of compound 1–5 in CDCl3
Position Compound 2 Compound 3 Compound 4 Compound 5 Compound 1
δH (ppm); (J Hz) δC (ppm) δH (ppm); (J Hz) δC (ppm) δH (ppm); (J Hz) δC (ppm) δH (ppm); (J Hz) δC (ppm) δH (ppm); (J Hz) δC (ppm)
2   160.5   160.6   160.2   160.5   160.4
3 6.34, d, 9.6 114.7 6.30, d, 9.5 114.7 6.31; d, 9.76 114.8 6.31, d, 9.4 114.8 6.35, d, 9.4 114.7
4 7.74, d, 9.5 144.3 7.70, d, 9.5 144.4 7.71; d, 9.76 144.3 7.69, d, 9.4 146.8 7.75, d, 9.4 144.4
4a   116.4   116.5   116.4   116.50   116.5
5 7.34, s 113.2 7.29, s 113.2 7.33; s 113.8 7.32, s 113.6 7.36, s 113.5
6   125.8   125.9   126.4   125.9   125.9
7   148.7   148.6   147.9   148.6   148.6
8   131.5   131.7   131.5   130.1   131.3
8a   143.9   143.8   143.3   143.9   143.9
2' 7.66, d, 2.2 146.6 7.62, d, 2.2 146.7 7.63; d 2.3 146.8 7.63, d, 2.3 144.4 7.68,d, 2.3 146.7
3' 6.79, d, 2.3 106.7 6.75, d,2.2 106.7 6.76; d 2.3 106.9 6.76, d, 2.3 106.8 6.80, d, 2.3 106.8
          4.68, dd       5.00; dd,  
1″ 5.01, d, 7.2 70.1 4.94, d, 7.2 70.2 10.4, 2.64.35, dd 72.4 4.98, m 69.6 11.6, 6.85.03; dd, 69.6
          10.4, 7.8       11.6, 6.8  
2″ 5.57, t, 7.1 119.4 5.54, m 119.8 3.80, dd 7.8, 2.6 75.7 5.65, m 123.9 5.67; br t, 6.8 123.5
3″   143.2   139.8   71.5   137.1   137.7
4″ 1.98, s 39.5 1.65, s 18.2 1.22, s 26.7 2.24; dd,13.9, 6.42.34; dd,13.9, 6.4 43.3 2.23;dd, 13.7, 6.7 2.41; dd, 13.7, 6.7 44.8
5″ 1.99, s 26.3 1.67, s 25.9 1.26, s 25.1 4.84, m 148.4 4.56; dt, 7.6, 6.7, 4.5, 1.84; dt, 13.0, 7.6 76.4
6″ 4.98, m 123.7         6.85, s 79.6 2.02; ddd, 13.0, 8.9,4.5 34.7
7″   131.7           131.4 2.61; ddq, 8.9, 7.6, 7.4 33.7
8″ 1.61, s 25.6           174.0   179.7
9″ 1.67, s 16.5         1.71, s 10.7 1.73; s 17
10″ 1.54, s 17.6         1.80, s 17.3 1.23; d, 7.4 15.8
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