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Planta Med
DOI: 10.1055/a-2589-5900
Original Papers

Fused Tricyclic Naphthalene Lactones and a Xanthone from Ventilago maingayi and their Anti-HIV-1 Activity

Ponsiri Liangsakul
1   Department of Chemistry, and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok, Thailand
2   Department of Agronomy, Faculty of Agriculture at Kamphaeng Saen, Kasetsart University, Kamphaeng Saen Campus, Nakhon Pathom, Thailand
,
Chutima Kuhakarn
1   Department of Chemistry, and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok, Thailand
,
Siriporn Jungsuttiwong
3   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani, Thailand
,
Ratchadaree Intayot
3   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani, Thailand
,
Sariyarach Thanasansurapong
1   Department of Chemistry, and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok, Thailand
,
Radeekorn Akkarawongsapat
4   Department of Microbiology, Faculty of Science, Mahidol University, Bangkok, Thailand
,
Arthit Chairoungdua
5   Department of Physiology, Faculty of Science, Mahidol University, Bangkok, Thailand
,
Narong Nuntasaen
6   The Forest Herbarium National Park, Wildlife and Plant Conservation Department, Ministry of Natural Resources and Environment, Bangkok, Thailand
,
Sakchai Hongthong
7   Division of Chemistry, Faculty of Science and Technology, Rajabhat Rajanagarindra University, Chachoengsao, Thailand
,
Vichai Reutrakul 
1   Department of Chemistry, and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok, Thailand
› Author Affiliations
This research has received financial support from NSRF via the Program Management Unit for Human Resources & Institutional Development, Research, and Innovation [Grant No. B16F640099]. The authors are grateful to the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Ministry of Higher Education, Science, Research and Innovation, and Mahidol University for instrumental support. S. H. acknowledged the Faculty of Science and Technology, Rajabhat Rajanagarindra University. Special thanks go to Mr. Chanchai Sukkum (Rajabhat Rajanagarindra University) for constructive comments, Dr. Samran Prabpai (Faculty of Science, Mahidol University) for X-ray diffraction analysis, Dr. Rattanawalee Rattanawan (Faculty of Science, Ubon Ratchathani University) for ECD calculations, Dr. Phongthon Kanjanasirirat (Department of Pathobiology, Faculty of Science, Mahidol University) for biological calculations, and Ms. Chanita Napaswad and Ms. Jitra Limthongkul (Department of Microbiology Faculty of Science, Mahidol University) for anti-HIV assays.
› Further Information
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Abstract

Three previously undescribed compounds, including two fused tricyclic naphthalene lactones (ventilaganones A and B, 1 and 2) and a xanthone (ventilagoxanthone, 3), along with eight known compounds (4–11), were isolated from the bark of Ventilago maingayi. Their structures were elucidated by extensive analysis of their spectroscopic data and by comparison with those of related compounds reported in the literature. The absolute configuration of ventilaganone A (1) was established by single-crystal X-ray analysis. Anti-HIV-1 activity of the isolated compounds was evaluated with a reverse transcriptase (RT) assay and a syncytium reduction assay using the ΔTat/RevMC99 virus in the 1A2 cell line. Compounds 1, 2, 4, 5, and 8–11 showed inhibitory activity against syncytium formation, while most compounds were found to be inactive in the reverse transcriptase assay.

Keywords

Ventilago maingayi - Rhamnaceae - Naphthalenes - Xanthones - Emodin - anti-HIV-1 activity

Supporting Information

    Details of the extraction and isolation procedures, preliminary biological screening data along with 1H, 13C, 2D NMR, and HR-ESI-MS spectra of compounds 1–3 are available in Supporting Information.

  • Supporting Information


Publication History

Received: 28 October 2024

Accepted after revision: 16 April 2025

Accepted Manuscript online:
16 April 2025

Article published online:
08 May 2025

© 2025. Thieme. All rights reserved.

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