Six new phenylpropanoid derivatives from chemically converted extract of alpinia galanga (L.) and their antiparasitic activities

Melanny Ika Sulistyowaty, Nguyen Hoang Uyen, Keisuke Suganuma, Ben Yeddy Abel Chitama, Kazuhide Yahata, Osamu Kaneko, Sachiko Sugimoto, Yoshi Yamano, Susumu Kawakami, Hideaki Otsuka, Katsuyoshi Matsunami

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Chemical conversion of the extract of natural resources is a very attractive way to ex-pand 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 substan-tial 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.

Original languageEnglish
Article number1756
JournalMolecules
Volume26
Issue number6
DOIs
Publication statusPublished - 2 Mar 2021

Keywords

  • Alpinia galanga
  • Chemically converted extract
  • Leishmania
  • Malaria
  • NTDs (neglected tropical diseases)
  • Phenylpropanoid
  • Plasmodium
  • Trypanosoma
  • Unnatural natural product

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