Anti-HIV-1 activities of constituents from the rhizomes of Boesenbergia thorelii

Wisuwat Thongphichai; Patoomratana Tuchinda; Manat Pohmakotr; Vichai Reutrakul; Radeekorn Akkarawongsapat; Chanita Napaswad; Jitra Limthongkul; Thaya Jenjittikul; Saowanit Saithong

doi:10.1016/j.fitote.2019.104388

Anti-HIV-1 activities of constituents from the rhizomes of Boesenbergia thorelii

Fitoterapia. 2019 Nov:139:104388. doi: 10.1016/j.fitote.2019.104388. Epub 2019 Oct 23.

Authors

Wisuwat Thongphichai¹, Patoomratana Tuchinda², Manat Pohmakotr¹, Vichai Reutrakul¹, Radeekorn Akkarawongsapat³, Chanita Napaswad³, Jitra Limthongkul³, Thaya Jenjittikul⁴, Saowanit Saithong⁵

Affiliations

¹ Department of Chemistry, Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
² Department of Chemistry, Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand. Electronic address: patoomratana.tuc@mahidol.ac.th.
³ Department of Microbiology, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
⁴ Department of Plant Science, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
⁵ Department of Chemistry, Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand; Medical Science Research and Innovation Institute, Prince of Songkla University, Songkhla 90112, Thailand.

PMID: 31655087
DOI: 10.1016/j.fitote.2019.104388

Abstract

A new lignan, thoreliin A (1), and a new bisnorlignan, thoreliin B (2), were isolated from a MeOH extract of the rhizomes of Boesenbergia thorelii. In addition, the known bisnorlignans 3 and 4, neolignan 5, phenylpropanoids 6-15, as well as benzenoids 18-21 were also obtained from the same source. The structures were elucidated based on their spectroscopic data. By single crystal X-ray analysis, the relative stereochemistry of 1 was confirmed. All isolated compounds were evaluated for anti-HIV-1 activities. Among them, thoreliin A (1) exhibited anti-HIV-1 activities on both HIV-1 reverse transcriptase (41.43% inhibition at 200 μg/mL) and syncytium reduction assays (EC₅₀ 20.6 μM, SI 3.7), while compounds 3-6, 9 and 11-21 showed anti-HIV-1 activity only in the anti-syncytium assay (EC₅₀ 6.6-454.1 μM, SI >1.32-7.75).

Keywords: Anti-HIV-1 activities; Benzenoids; Bisnorlignans; Boesenbergia thorelii; Lignan; Neolignans; Phenylpropanoids.

MeSH terms

Anti-HIV Agents / isolation & purification
Anti-HIV Agents / pharmacology*
HIV-1 / drug effects*
Lignans / isolation & purification
Lignans / pharmacology*
Molecular Structure
Phytochemicals / isolation & purification
Phytochemicals / pharmacology
Rhizome / chemistry*
Thailand
Zingiberaceae / chemistry*

Substances

Anti-HIV Agents
Lignans
Phytochemicals