Bioassay-Guided Isolation and Identification of Antiplasmodial Compounds from the Stem Bark of Clausena excavata

Prapairat Seephonkai; Chatthai Kaewtong; Phurpa Wangchuk; Kedchin Jearawuttanakul; Phongthon Kanjanasirirat; Suparerk Borwornpinyo; Tachin Khulmanee; Rapatbhorn Patrapuvich

doi:10.1055/a-2112-6631

Planta Medica, Table of Contents

Planta Med 2023; 89(12): 1165-1169
DOI: 10.1055/a-2112-6631

Biological and Pharmacological Activity

Original Papers

Bioassay-Guided Isolation and Identification of Antiplasmodial Compounds from the Stem Bark of Clausena excavata

Authors

Prapairat Seephonkai

¹Multidisciplinary Research Unit of Pure and Applied Chemistry, Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahasarakham University, Khamriang, Kantarawichai, Maha Sarakham, Thailand
Chatthai Kaewtong

¹Multidisciplinary Research Unit of Pure and Applied Chemistry, Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahasarakham University, Khamriang, Kantarawichai, Maha Sarakham, Thailand
Phurpa Wangchuk

²Centre for Molecular Therapeutics, Australian Institute of Tropical Health and Medicine, James Cook University, Cairns Campus, Smithfield, Queenland, Australia
Kedchin Jearawuttanakul

³Excellent Center for Drug Discovery, Faculty of Science, Mahidol University, Bangkok, Thailand
Phongthon Kanjanasirirat

³Excellent Center for Drug Discovery, Faculty of Science, Mahidol University, Bangkok, Thailand
Suparerk Borwornpinyo

³Excellent Center for Drug Discovery, Faculty of Science, Mahidol University, Bangkok, Thailand
Tachin Khulmanee

⁴Drug Research Unit for Malaria, Faculty of Tropical Medicine, Mahidol University, Bangkok, Thailand
Rapatbhorn Patrapuvich

⁴Drug Research Unit for Malaria, Faculty of Tropical Medicine, Mahidol University, Bangkok, Thailand

Abstract

Clausena excavata is a medicinal plant widely distributed in Southeast Asia. It is used for a variety of indications, including to treat malaria. In our present study, a phytochemical study of the methanol extract from the stem bark of C. excavata led to the isolation of five pyranocoumarins, nordentatin (1), dentatin (2), kinocoumarin (3), clausarin (4), and clausenidin (5), and a coumarin, 8-hydroxy-3″,4″-dihydrocapnolactone-2′,3′-diol (6). The isolation of compound 6 from C. excavata and the antiplasmodial activities against a multidrug-resistant K1 strain of Plasmodium falciparum of 1, 3, and 5 were reported for the first time. Compounds 3 and 4 exhibited potent antiplasmodial activities with EC₅₀ values of 1.10 and 0.58 µM, respectively, while 1 and 5 had EC₅₀ values of 5.62 and 7.15 µM, respectively. A prenyl group attached to the C-3 or C-12 position on the pyranocoumarin ring probably plays an important role on the activity. A hydroxyl group at the C-10 position is also likely to enhance the activity.

Key words

Clausena excavata - Rutaceae - clausarin - kinocoumarin - nordentatin - pyranocoumarins - antiplasmodial compound

Full Text

References

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Supplementary Material

Supporting Information (PDF)