Phenylethylchromones with In Vitro Antitumor Promoting Activity from Aquilaria filaria

Airi Suzuki; Katsunori Miyake; Yohei Saito; Faradiba Abdul Rasyid; Harukuni Tokuda; Misa Takeuchi; Nobutaka Suzuki; Eiichiro Ichiishi; Tetsuo Fujie; Masuo Goto; Yohei Sasaki; Kyoko Nakagawa-Goto

doi:10.1055/s-0042-110858

Planta Medica, Table of Contents

Planta Med 2017; 83(03/04): 300-305
DOI: 10.1055/s-0042-110858

Natural Product Chemistry and Analytical Studies

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Phenylethylchromones with In Vitro Antitumor Promoting Activity from Aquilaria filaria

Authors

Airi Suzuki

¹School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Japan
Katsunori Miyake

¹School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Japan
Yohei Saito

¹School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Japan
Faradiba Abdul Rasyid

¹School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Japan
Harukuni Tokuda

²Organic Chemistry in Life Science, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto Japan
Misa Takeuchi

¹School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Japan
Nobutaka Suzuki

³Department of Complementary and Alternative Medicine, Clinical R&D, Graduate School of Medical Science, Kanazawa University, Kanazawa, Japan
Eiichiro Ichiishi

⁴International Health & Welfare University Hospital, Nasushiobara, Tochigi, Japan
Tetsuo Fujie

¹School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Japan
Masuo Goto

⁵Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina, USA
Yohei Sasaki

¹School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Japan
Kyoko Nakagawa-Goto

¹School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Japan

⁵Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina, USA

Abstract

A new chromone, 2-(2-hydroxy-2-phenylethyl)chromone (1), was isolated together with ten known phenylethyl chromones from MeOH extracts of agarwood (Aquilaria filaria). The selected compounds were evaluated in an antiproliferative assay against five human tumor cell lines, including a multidrug-resistant cell line. They were also tested for antitumor promoting activity, as mediated by 12-O-tetradecanoylphorbol-13-acetate-induced activation of the Epstein-Barr virus early antigen in Raji cells. Among all compounds, 4′,7-dimethyoxy-6-hydroxychromone (2) displayed broad spectrum antiproliferative activity against all tumor cell lines tested with IC₅₀ values of 25–38 µM, while 8 was selectively inhibitory against multidrug-resistant cells. All tested compounds suppressed tumor promotion at noncytotoxic concentrations. 4′,6-Dihydroxyphenylethylchromone (7) exhibited the most potent effect with an IC₅₀ value of 319 mol ratio relative to 12-O-tetradecanoylphorbol-13-acetate. This study is the first to report the antitumor promoting activity of 2-(2-phenylethyl)chromone derivatives, as well as the selective antiproliferative activity of 8 against a multidrug-resistant tumor cell line.

Key words

agarwood - Aquilaria filaria (Oken) Merr. - Thymelaeaceae - 2-(2-phenylethyl)chromone - antitumor promoting activity - antiproliferative activity

Full Text

References

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Supplementary Material

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