槲皮素
化学
苯丙素
根茎
抗寄生虫的
IC50型
立体化学
布氏锥虫
乙酸乙酯
姜科
杀虫药
异香豆素
传统医学
有机化学
生物化学
体外
生物合成
酶
芦丁
病理
基因
医学
抗氧化剂
作者
Melanny Ika Sulistyowaty,Nguyen Hoang Uyen,Keisuke Suganuma,Ben-Yeddy Abel Chitama,Kazuhide Yahata,O. Kaneko,Sachiko Sugimoto,Yasushi Yamano,Susumu Kawakami,Hideaki Otsuka,Katsuyoshi Matsunami
出处
期刊:Molecules
[MDPI AG]
日期:2021-03-21
卷期号:26 (6): 1756-1756
被引量:10
标识
DOI:10.3390/molecules26061756
摘要
Chemical conversion of the extract of natural resources is a very attractive way to expand the chemical space to discover bioactive compounds. In order to search for new medicines to treat parasitic diseases that cause high morbidity and mortality in affected countries in the world, the ethyl acetate extract from the rhizome of Alpinia galanga (L.) has been chemically converted by epoxidation using dioxirane generated in situ. The biological activity of chemically converted extract (CCE) of A. galanga (L.) significantly increased the activity against Leishmania major up to 82.6 ± 6.2 % at 25 μg/mL (whereas 2.7 ± 0.8% for the original extract). By bioassay-guided fractionation, new phenylpropanoids (1–6) and four known compounds, hydroquinone (7), 4-hydroxy(4-hydroxyphenyl)methoxy)benzaldehyde (8), isocoumarin cis 4-hydroxymelein (9), and (2S,3S,6R,7R,9S,10S)-humulene triepoxide (10) were isolated from CCE. The structures of isolated compounds were determined by spectroscopic analyses of 1D and 2D NMR, IR, and MS spectra. The most active compound was hydroquinone (7) with IC50 = 0.37 ± 1.37 μg/mL as a substantial active principle of CCE. In addition, the new phenylpropanoid 2 (IC50 = 27.8 ± 0.34 μg/mL) also showed significant activity against L. major compared to the positive control miltefosine (IC50 = 7.47 ± 0.3 μg/mL). The activities of the isolated compounds were also evaluated against Plasmodium falciparum, Trypanosoma brucei gambisense and Trypanosoma brucei rhodeisense. Interestingly, compound 2 was selectively active against trypanosomes with potent activity. To the best of our knowledge, this is the first report on the bioactive “unnatural” natural products from the crude extract of A. galanga (L.) by chemical conversion and on its activities against causal pathogens of leishmaniasis, trypanosomiasis, and malaria.
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