Targeted Isolation of Antiviral Labdane Diterpenes from the Bark of Neo-uvaria foetida (Annonaceae) using LC-MS/MS-Based Molecular Networking

Sukumaran, S. Yaallini and Herrscher, Charline and Rasol, Nurulfazlina Edayah and Othman, Muhamad Aqmal and Liew, Sook Yee and Ismail, Nor Hadiani and Seron, Karin and Litaudon, Marc and Awang, Khalijah and El Kalamouni, Chaker and Apel, Cecile and Zahari, Azeana (2024) Targeted Isolation of Antiviral Labdane Diterpenes from the Bark of Neo-uvaria foetida (Annonaceae) using LC-MS/MS-Based Molecular Networking. Journal of Natural Products, 87 (8). pp. 1941-1951. ISSN 0163-3864, DOI https://doi.org/10.1021/acs.jnatprod.4c00342.

Full text not available from this repository.
Official URL: https://doi.org/10.1021/acs.jnatprod.4c00342

Abstract

In the search of new inhibitors for human coronavirus (HCoV), we screened extracts of endemic Annonaceae plants on an assay using a cellular model of Huh-7 cells infected with the human alphacoronavirus HCoV-229E. The EtOAc bark extract of the rare Southeast Asian plant Neo-uvaria foetida exhibited inhibition of HCoV-229E and SARS-CoV-2 viruses with IC50 values of 3.8 and 7.8 mu g/mL, respectively. Using LC-MS/MS and molecular networking analysis guided isolation, we discovered two new labdane-type diterpenoids, 8-epi-acuminolide (1) and foetidalabdane A (4), and three known labdane diterpenoids, acuminolide (2), 17-O-acetylacuminolide (3), and spiroacuminolide (5). A new norlabdane diterpene, 16-foetinorlabdoic acid (6), was also isolated and identified. Excluding compounds 5 and 6, all other metabolites were active against the virus HCoV-229E. Terpenoids 1 and 4 presented antiviral activity against SARS-CoV-2 with IC50 values of 63.3 and 93.5 mu M, respectively, indicating lower potency. Additionally, virological assays demonstrated that compounds 1, 2, and 3 exert antiviral effects against Zika virus by specifically interfering with the late stage of its infectious cycle with IC50 values of 76.0, 31.9, and 14.9 mu M, respectively.

Item Type: Article
Funders: Ministry of Education, Malaysia (FRGS/1/2021/STG04/UM/02/12), Conseil Regional de La Reunion (20201437-0027601), France 2030 program, ANRS I MIE (ANRS-23-PEPR-MIE004), OHSEA project under the Institute de Recherche Pour Le Development, France (IF029-2022), Universite Paris-Saclay, Agence Nationale de la Recherche (ANR) (ANR-11-IDEX-0003-02 (10-LABX-0033))
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 05 Feb 2025 07:42
Last Modified: 05 Feb 2025 07:42
URI: http://eprints.um.edu.my/id/eprint/47561

Actions (login required)

View Item View Item