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Park, Lee, Lee, Kim, Chun, Kim, Yang, Lee, and Kwon: A new 3, 4-epoxyfurocoumarin from Heracleum moellendorffii Roots
Original Article

Natural Product Sciences 2017;23(3):213-216.

Published online: 20 January 2017

DOI: https://doi.org/10.20307/nps.2017.23.3.213

A new 3, 4-epoxyfurocoumarin from Heracleum moellendorffii Roots

Sang Yeol Park1, †, Nara Lee1, †, SunKyoung Lee1, †, Myong Jo Kim2, Wanjoo Chun3, Hyun Pyo Kim1, Hee Jung Yang1, Ho Sun Lee4, Yongsoo Kwon1, ∗

1College of Pharmacy, Kangwon National University, Chuncheon 24341, Korea

2College of Agriculture and Life science, Kangwon National University, Chuncheon 24341, Korea

3School of Medicine, Kangwon National University, Chuncheon 24341, Korea

4Yanggu Agricultural Technology Center, Yanggu 24522, Korea

∗Author for correspondence Yongsoo Kwon, College of Pharmacy, Kangwon National University, Chuncheon, 24341, Korea Tel: +82-033-259-5631; E-mail: yskwon@kangwon.ac.kr

a† These authors contributed equally to this work.

Received 11 April 2017       Revised 13 June 2017       Accepted 13 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

Activity-guided isolation of Heracleum moellendorffii roots led to four coumarin derivatives as acetylcholinesterase inhibitors. The structures of these isolates were characterized by spectroscopic method to be angelicin (1), isobergapten (2), pimpinellin (3), and (3S, 4R)-3, 4-epoxypimpinellin (4). All the isolated compounds 1, 2, 3, and 4 showed moderate inhibition activities against acetylcholinesterase with the IC50 values of 10.2, 18.1, 21.5 and 22.9 µM, respectively. (3S, 4R)-3, 4-Epoxypimpinellin (4) was newly isolated from the plant source.

Keywords: Heracleum moellendorffii, Angular furanocoumarins, (3S, 4R)-3, 4-epoxypimpinellin, Acetylcholinesterase inhibition

References

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Fig. 1.
Structures of 1 – 4.
nps-23-213f1.tif
Fig. 2.
Important HMBC correlations of 4.
nps-23-213f2.tif
Table 1.
13C-NMR data of 1 – 4 (150 MHz, CDCl3)
No 1 2 3 4 5,8-dimethoxyetane 3,4-epoxy-furanocoumarin12
2 160.89 161.02 160.84 164.69 164.7
3 114.12 112.21 113.72 39.80 37.5
4 144.55 139.89 139.92 38.25 39.1
4a 113.52 105.81 109.44 106.45 107.5
5 123.83 154,27 144.44 147.55 133.8
6 108.83 90.53 135.12 134.56 112.9
7 157.37 157,98 149.80 148.19 147.2
8 116.94 110.06 114.09 113.81 147.4
8a 148.50 148.79 143.17 139.53 139.1
2' 145.89 144.32 145.39 144.58 145.8
3' 104.11 103.73 104.29 103.97 103.4
OCH3   56.31 62.38 60.77 60.4
OCH3     61.23 60.77 60.4

Chemical shifts are represented parts per million (δ)

Table 2.
Acetylcholinesterase inhibitory activity of compounds 1 – 4.
Tested compounds IC50a) (μg/ml) IC50 (μM)
1 1.9 10.2
2 3.9 18.1
3 5.3 21.5
4 6.0 22.9
Eserineb) 0.007 0.03

a) The inhibitory activity dose that reduced 50% of acetylcholinesterase activity and expressed as mean of two different experiments.

b) A positive control

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