Uvarmicranones A and B, two new benzoquinones and cytotoxic constituents from the stems of Uvaria micrantha (A. DC.) Hook. f. & Thomson

Abstract

Two novel benzoquinones, uvarmicranones A (1) and B (2), along with 15 known compounds (3 − 17) were isolated from the stems of Uvaria micrantha (Annonaceae). Their structures were elucidated by analyses of NMR and high-resolution mass data. A plausible biosynthetic pathway of uvarmicranone A (1) via Diels-Alder cycloaddition reaction was also proposed. Some isolated compounds were evaluated for their cytotoxic activities. Compounds 1, 14, and 15 showed moderate cytotoxic effects against T-cell acute lymphoblastic cells (MOLT-3), with IC₅₀ values of 7.83 ± 0.83, 6.53 ± 1.01, and 4.20 ± 0.29 μM, respectively. Additionally, compound 15 exhibited moderate cytotoxicity against cervical carcinoma cells (HeLa) with an IC₅₀ value of 7.00 ± 3.15 μM.

Keywords:

• Uvaria micrantha
• Annonaceae
• benzoquinone
• cytotoxicity
• uvarmicranone

Acknowledgments

The research was financed by the Chulabhorn Research Institute (CRI) and the Center of Excellence on Environment Health and Toxicology, Science & Technology Postgraduate Education and Research Development Office (PERDO, Ministry of Education. We acknowledge the help of Assist. Prof. Dr. Wichan Eiadthong from Kasetsart University in confirming the identity of the plant. We thank the CRI staff members, Ms. Pakamas Intachote, Ms. Suchada Sengsai, and Ms. Busakorn Saimanee for the determination of cytotoxic activities, Ms. Kittiporn Trisuppakant, Mr. Somchai Pisutcharoenpong, and Mr. Nitirat Chimnoi for the collection of spectral data and Ms. Sawangjitt Wittayalai for her assistance in chromatographic isolation.

Disclosure statement

The authors reported no potential conflict of interest.

Correction Statement

This article has been republished with minor changes. These changes do not impact the academic content of the article.