Anti-inflammatory canthin-6-one alkaloids from the roots of Thailand Eurycoma longifolia Jack
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Anti‑inflammatory canthin‑6‑one alkaloids from the roots of Thailand Eurycoma longifolia Jack Ying Zhang1 · Wei Zhao1 · Jingya Ruan2 · Nuttapong Wichai3 · Zheng Li2 · Lifeng Han2 · Yi Zhang1,2 · Tao Wang1,2 Received: 7 May 2020 / Accepted: 1 July 2020 © The Japanese Society of Pharmacognosy 2020
Abstract Two new canthin-6-one alkaloids, 4,9-dimethoxy-5-hydroxycanthin-6-one (1) and 9-methoxy-(R/S)-5-(1-hydroxyethyl)canthin-6-one (2), together with fifteen known ones were isolated from the roots of Thailand Eurycoma longifolia Jack. Among the known canthin-6-one alkaloids, compounds 9 and 16 were isolated from the Eurycoma genus for the first time. Meanwhile, the nitric oxide (NO) inhibitory activities of all isolates were examined in lipopolysaccharide (LPS)-stimulated RAW264.7 cells at 50 µM. Moreover, a dose-dependent experiment was conducted for active compounds 1, 2, 4, 6, 7, 10, 12–17 at the concentration of 10, 25, and 50 µM, respectively. Consequently, compounds 1, 4, 6, 7, 12, 14, 15, as well as 17 were found to inhibit NO release from RAW264.7 cells in a dose-dependent manner.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11418-020-01433-6) contains supplementary material, which is available to authorized users. * Yi Zhang [email protected] * Tao Wang [email protected] 1
Tianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, China
2
Institute of TCM, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, China
3
Faculty of Pharmacy, Mahasarakham University, Mahasarakham 44150, Thailand
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Vol.:(0123456789)
Journal of Natural Medicines
Graphic abstract
Two new canthin-6-one alkaloids, 4,9-dimethoxy-5-hydroxycanthin-6-one (1) and 9-methoxy-(R/S)-5-(1-hydroxyethyl)canthin-6-one (2), together with fifteen known ones were isolated from the roots of Thailand Eurycoma longifolia Jack. Among them, 1, 4, 6, 7, 12, 14, 15, as well as 17 were found to inhibit NO release from RAW264.7 cells in a dose-dependent manner at the concentration of 10, 25, and 50 µM. Keywords Thailand Eurycoma longifolia jack · Canthin-6-one alkaloids · Anti-inflammatory · RAW264.7 cell · NO production
Introduction Eurycoma longifolia Jack (Simaroubaceae) is one of the most popular tropical herbal plants, indigenous to south-east Asian countries like Malaysia, Indonesia, and Thailand. The roots of E. longifolia exhibited various biological activities, such as anti-malarial, anti-fatigue, hypertension, anti-pyretic and male testosterone level increasement [1–3]. The plant is rich in various bioactive constituents, among them, quassinoids and β-carboline alkaloids play the important roles [4, 5]. However, the
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present studies have focused more on its quassinoids, and so far, 190 quassinoids have been isolated and reported [6]. While the β-carboli
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