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Jia, Guan, Ma, Wang, and Shao: Pestalotiolide A, a New Antiviral Phthalide Derivative from a Soft Coral-derived Fungus Pestalotiopsis sp.
Original Article

Natural Product Sciences 2015;21(4):227-230.

Published online: 17 January 2015

DOI: https://doi.org/10.20307/nps.2015.21.4.227

Pestalotiolide A, a New Antiviral Phthalide Derivative from a Soft Coral-derived Fungus Pestalotiopsis sp.

Yan-Lai Jia, Fei-Fei Guan, Jie Ma, Chang-Yun Wang, Chang-Lun Shao∗

Key Laboratory of Marine Drugs, The ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China

∗ Author for correspondence Chang-Lun Shao, Key Laboratory of Marine Drugs, The ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China Tel: +82-; E-mail: shaochanglun@163.com

      Revised 30 April 20154 June 2015       Accepted 5 June 2015

Copyright © 2015 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

Chemical investigation of the fermentation broth of a Soft Coral-Derived fungus Pestalotiopsis sp., led to the isolation of a new phthalide derivative, pestalotiolide A (1), three known analogues (2, 3 and 4), along with 5'-O-acetyl uridine (5) first isolated as a natural product. The structure of the new compound (1) was established by comprehensive spectroscopic analysis and chemical methods. Compounds 1 - 4 possessed varying degrees of antiviral activities, which was reported for the first time. Compared to the positive control ribavirin (IC50 = 418.0 µM), pestalotiolide A (1) exhibited significant anti-EV71 activity in vitro, with an IC50 value of 27.7µ M. Furthermore, the preliminary structure-activity relationship of antiviral activities was also discussed.

Keywords: Marine Fungus, Pestalotiopsis sp., Structure-Activity Relationship, Antiviral Activity

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Fig. 1.
The structures of 1 - 5 isolated from Pestalotiopsis sp.
nps-21-227f1.tif
Fig. 2.
Key HMBC () correlations of 1.
nps-21-227f2.tif
Table 1.
1H and13C NMR data of 1 in CD3 OD. (δ in ppm, J in Hz, 500 MHz for 1H and 125 MHz for 13C)
No. δC (J in Hz) δH (J in Hz)
1 172.1 −
2 70.2 5.27 (2H, s)
3 148.1 −
4 122.8 −
5 164.5 −
6 128.5 −
7 153.9 −
8 113.4 −
1' 105.9 5.12 (1H, d,7.8)
2' 75.7 3.54 (1H, t, 8.5)
3' 78.1 3.45 (1H, t, 8.4)
4' 71.5 3.37 (1H, m)
5' 75.6 3.37 (1H,m)
6' 64.2 4.33 (1H, d, 11.8)
4.19 (H, dd, 11.8,5.5)
1″ 172.4
2″ 20.6 1.94 (3H, s)
5-OMe 60.8 3.79 (3H, s)
4-Me 11.4 2.22 (3H, s)
6-Me 11.0 2.26 (3H, s)
Table 2.
Antiviral activities of the tested compounds 1 - 5a
virus TC50/IC50 (µ M)
1 2 3 4 5 Ribavirin
EV71 254.9/27.7 104.6/51.6 316.4/111.0 − 262.2/110.0 A/418.0
RSV 303.4/80.9 337.8/25.6 − 360.1/21.0 − A/78.0
HSV-1 − 337.8/63.9 − − − A/313.0
H1N1 − − − − − 625/156.0
Cox-B3 − − 353.1/95.9 360.6/19.6 297.2/127.5 A/39.0

a the symbol “−” means no antiviral activities, A > 4000. Cytotoxicity (TC50) and antiviral activity (IC50) are located in the left and right side of the symbol “/”, respectively.

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